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A COLLECTION OF TRANSGENDER
EROTIC ROMANCE STORIES
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This book is a work of fiction. All the characters in this book are fictitious
and any similarity to any person, living or dead, is purely coincidence.
Published By Honey Wagon Books
Copyright © 2015 by Nikki Crescent
Model License Holder: Ollyy Sanderson (Shutterstock Inc.)
Background Image License Yoko-Onos-Balls (Shutterstock Inc.)
Cover by Fleet Lebowski
All rights reserved. No part of this publication may be reproduced,
distributed, or transmitted in any form or by any means, including
photocopying, recording, or other electronic or mechanical methods, without
the prior written permission of the publisher, except in the case of brief
quotations embodied in critical reviews and certain other non-commercial
uses permitted by copyright law.
THE BOOKS INCLUDED IN THIS MEGA
TRANS FOR HIRE
HIS NEW GIRLFRIEND
TRANS CAM WHORE
CHEER FOR THE TEAM
THE GIRLFRIEND DARE
HIS NEW ROOMMATE
HE KNOWS MY SECRET
HIS FOR THE WEEK
GETTING THE PART
BECOMING A WOMAN
TRYING IT OUT
RAISING THE STAKES
HIS BIKINI BODY
DRESSING HIM UP
ONLY GIRLS GET A RIDE
HIS BIGGEST FAN
GIRLFRIEND FOR A DAY
GETTING THE JOB
THE SISSY CAMPAIGN
TRANS CHECK UP
MY BEST FRIEND’S SECRET
Table of Contents
About the Author
To all of my readers
You have made everything possible
TRANS FOR HIRE
Tanner made a bad deal with the wrong people. Now, he’s in a lot of debt.
$90,000 of debt, to be specific. And he doesn’t have long to make it up. He’s
But there’s a glimmer of hope. After a chance conversation with a
prostitute in a bar, Tanner learns there is one way to make big money in a
short period of time. Apparently, certain people will pay a lot of money to
sleep with a tranny prostitute.
And Tanner is desperate, willing to try anything. Even if it means getting
a bit of work done and taking a few in the backdoor.
I was in some serious debt. And I’m not talking about student loans or
mortgage debt or overdue car payments. I owed some mean people a lot of
money. It was my own fault; I knew the risk I was taking when I borrowed the
$90,000. I knew I was making a deal with the mafia. I knew I would end up at
the bottom of the river with cement blocks tied to my feet if I didn’t pay them
back. But I’d never been so confident about anything in my whole life. I had
an insider—he told me the stock would double overnight. He said it was a
It wasn’t a sure thing. In four days, I lost $80,000. I took the last of my
money out before it was a total loss. I had one week to pay it all back. I
thought about taking it to the casino, putting it all on black. I just needed it to
land on black three times in a row and I’d basically be back even. I could sell
my car and empty my life savings for the last ten grand.
I even walked into the casino with the last of my cash in a bag. But I
stopped myself. There is about a 12% chance of landing black three times in a
row. That’s an 88% chance of having some goomba curb stomp my face into
the pavement. I’d never been a lucky person, and I’d taken enough risks over
the past week.
I thought about running, leaving town. But where could I go? I knew they
would find me. It was 2016, after all. They had connections with the internet
companies, the IRS, even the FBI. I wouldn’t last ten minutes.
I had one week.
Seven days. Five business days—as if that made any difference.
From my apartment window, I could see three things: the corner where the
prostitutes stood waiting for work, the bar where the prostitutes hung out
between jobs, and the casino where the drunks hung out, trying to make
enough money to pay for the prostitutes. I didn’t exactly live in a high end
part of town.
I didn’t have cable, so watching the whores was my only source of free
entertainment. There was one girl who only stood out about once a week—a
real bombshell. I always wondered why did it—with a body and a face like
that, she could have been a model, or a movie star. Her legs—my God, her
legs. I’d never paid for sex before, but if I was going to, she would be the one.
There was no chance in hell I could afford her. Men constantly pulled up
to her and then drove away empty-handed. She only ever hopped into the
nicest cars—the Lamborghinis, the Ferraris, the Rolls Royces. Basically, if the
car wasn’t worth at least a quarter-million, she wasn’t getting in. She probably
made some alright coin.
Hell, even the less-attractive ladies got picked up by wealthy-enough
Whenever I watched the ladies stand out on that corner, I would always
see at least a couple of men stopped at red lights, shaking their heads as if
they were above the sex trade. Pricks. If I had a pair of tits on my chest and a
pussy between my legs, I would be down there, too.
I went down to get a drink at the bar. One of the girls sat down next to me.
“What’s your name?” she asked.
“Tanner,” I told her.
“Looking for a date, Tanner?” she asked.
I smiled and apologized. “You’re very beautiful, but I’m still trying to
figure out how I’m going to pay for this drink.” She wasn’t exactly beautiful,
but she was a nice enough lady. “How’s about a rain check?”
“Don’t sweat it, darling,” she said, and then she paid for my drink. She
looked around to make sure no one was looking, then she reached down my
pants, grabbed my cock and gave it a quick massage. Hell, she knew how to
work those fingers. It wasn’t even a ten second ordeal and I nearly came in
the palm of her hand. “Five hundred and you can stick it anywhere you’d
like,” she said as she stood up.
Jesus Christ, I thought. Five hundred bucks? If she cost five hundred,
what did the beauty on the street corner go for? “If you don’t mind my asking,
how much do you make in a night?” I asked.
“I don’t mind, sweetie. If I’m busy? Maybe three or four grand, plus tips.
One night I went home with twelve stuffed in my purse.”
“Twelve thousand?” I didn’t know whether or not to believe her. On a
scale from one to ten, she wasn’t even a solid five. Maybe a three. She was
kind of chubby, her eyes were kind of sunken, and her legs were kind of short.
She also had a smell that reminded me of my late-grandmother’s retirement
“Yeah, but I had two guys share the same backdoor that night. As far as
I’m concerned, it was money well earned.”
“You can fit two back there?”
“Let’s just say their wallets were bigger than their cocks.”
“Twelve thousand is a lot of money.” I couldn’t even imagine making that
kind of money in a single night. I hardly made that money in a whole year.
“Some girls make that every night—I’m not even kidding. I’m a low
earner. A few of the girls make that every job. Hell, even the trannies make
more than me—but to be fair, that’s a niche market.”
“A niche market?”
“A few clients paying a lot of money. And I mean, a lot of money. They’re
into some weird stuff though. I did a job with a tranny friend of them once.
The guy wanted to watch my friend fuck me in the ass. Money was good, but
I don’t think I would do that again.”
“Why not?” I asked.
“I don’t know. I got a weird vibe from it. After I was done, the client kept
the tranny around for himself. She finally came out a few hours later with a
hell of a lot more money than I made. I can only image what he had her
I was strangely fascinated. “What did he have her doing, do you think?”
“I don’t know, but my tranny friend took a few days off after that night.
She wouldn’t talk to me about it.”
I loved how open the whore was about her career choice. The bartender
came around and asked if I wanted another drink. I dug into my pockets and
started to count my change. I only needed two dollars, but I was about fifty
cents short. My new whore friends slapped down a five. “It’s on me,” she
said, and then she gave me a smile that was full of pity. Then she asked me to
follow her to the bathroom and she gave me a pity blowjob.
She was a pro. She pumped my dick with a ferocious elegance, and she
sucked it like she wanted it. She managed to get my cock halfway down her
throat without even the slightest gag. “Where do you want to come, baby?”
she asked me.
“Where can I come?”
“Anywhere but the face. Are my tits okay?” She didn’t stop beating me
off while she talked to me. There was something extremely arousing about
that. “Or you can come on my ass. Your choice.”
“I’ll take the tits.”
Then, she did a little flicking motion with her tongue along the underside
of my cock, and five seconds later I was blasting hot, sticky cum onto her big,
fake tits. She made some orgasm sound effects which were convincing, but I
knew they were fake.
“I would give you a tip, but…” I felt like a cheap pile of shit. I couldn’t
even look her in the eyes.
“I wouldn’t be mad if you ate me out,” she said.
So I did. It seemed like the least I could do. She sat down on the toilet
seat, slipped off her black thong, and spread her legs. Her pussy had a natural
gape to it, probably from years of constant penetration. Once my face was
nestled between her plump thighs, and my nose was pressed into her pubic
hair, she pulled me in with her hands and held me in place. She wasn’t letting
go until I got her off. It really was the least I could do. It took about fifteen
minutes, and my tongue was limp and sore by the end of it, but I got her off.
I didn’t sleep that night. Instead, I just stared up at my ceiling and
wondered how I was going to turn $10,000 into $90,000 in one week. The
casino was my last resort, I knew I had that in my back pocket if nothing else
worked out. Even if I could just make $10,000 into $45,000, I would only
need to hit black once—that would increase my chance of surviving the mafia
from 12% to 50%. I could play those odds.
But the question was still the same. Where could I make that kind of
money in what was now six days? I had no ideas, aside from various ways to
gamble it. Bet what I had on a hockey game, bet it all on a horse down at the
track, try to count cards down at the casino. I was awful with math—I would
never make it a single round trying to count cards.
I laughed—I could become a tranny prostitute. I laughed at the thought for
a while and then I stopped laughing. Maybe it wasn’t the dumbest idea. I only
needed to make about $9,000 each night. According to my new prostitute
friend, that was doable in what she called “a niche market.”
I slapped myself across the face. Don’t be an idiot, Tanner. You aren’t
seriously considering getting a sex change to pay off your debts, are you? I
continued to think about it. It wasn’t like I needed a full sex change—I could
probably get by with a half-decent set of fake tits. I could shave my legs, wax
my eyebrows, spend a couple hundred bucks on some clothes and a decent
wig. I’d seen some of those tranny prostitutes my whore friend was talking
about. Some of them were surprisingly beautiful, but most of them looked
like dudes in drag. Even they got picked up. And hell, I’d had people tell me I
made a pretty man before. I bet I could pull it off.
And worse case scenario, I get the implants taken out, right?
I slapped myself again, and got a drink of water. The entire notion was
There was a knock at my door. There was a bluntness to the knock. A
shiver ran up my spine and through the roof of my apartment. I opened the
door anyway. It was an Italian-looking man in a black suit. It didn’t take me
long to realize he was with the mafia. “Can I help you?” I asked.
“Yeah, I’m here for the money,” he said with a bluntness to compliment
“I still have six days.” I tried to close the door but he stopped it with his
“Well, do you have it?” he asked.
“I’ll have it in six days.”
“So you don’t have it.”
“Maybe I do, maybe I don’t. But I’ve got six days to pay it back.” The
man gave me a sour look. Then I noticed the bulge in his coat. There was a
gun there and something told me the guy knew how to use it.
“I’ll have the money, man, I swear.”
He stared at me in a silence for a moment before turning back towards the
staircase and disappearing. I didn’t have any more time to think. Every day I
spent thinking was a day wasted, potential money wasted. If I was going to
survive more than the next six days, I needed money, and there was only one
way I could think to make it.
I called a few clinics. They all had waiting lists at least three months long.
So I went online to see what I could find. I was determined. When your life is
on the line, you can make anything happen. You can turn shit into solid gold
if you needed to—and I needed to. I found a clinic in Venezuela. Round trip
flight was $1,600. The operation was $8,000 and change. I could be there and
back in two days. That would leave four days to make the money—four days
to make $45,000, and a hell of a lot of luck. I left for the airport.
The doctor didn’t speak a word of English, but it didn’t matter, he knew
what I wanted. There were a dozen other men in the waiting room who were
there for the same exact thing. I wondered how many of them were just in it
for the cash, like me. They all wanted massive tits and extreme facial surgery
—nose jobs, face lifts, Botox injections, and so on. They wanted to be
women. I didn’t. I wanted to be a tranny, a ladyboy, a shemale. That’s where
the money was—and I needed the money.
I was almost a little disappointed waking up from my anaesthetic-induced
slumber when I saw that the doctor did a goddamned incredible job. My tits
looked like… tits. “You don’t think they look too real?” I asked the doctor. A
nurse translated for me.
He looked at me as if I was mentally retarded, and then gave me a shot in
the arm. It was a thick needle and hurt like hell.
“Ouch. What was the hell was that?” I asked.
“It’s for your voice and your face hairs,” the nurse said in her thick
Venezuelan accent. “New drug. Not legal in America. Should start to notice
the effects in a day or two.”
It was even quicker than that. As I stepped off of the plane, back on
American soil, I waved at the hot little flight attendant. “See you around,” I
said. I didn’t even recognize my own voice. I thought maybe I didn’t say
anything, and it was someone behind me who actually spoke—but it was me,
it was my voice, my new voice. Panic finally started to sink in. I was halfway
to becoming a woman. I wasn’t Tanner anymore.
When I stepped out from the airport, the sun was lingering on the horizon.
I had four days to make that money, including today. I was tired, but I had
work to do. I had money to make, and I still wasn’t ready to hit the streets. I
still needed to hit up the mall. I’d never bought women’s clothes or makeup
before. I needed to think like a woman. First I bought a wig. I figured,
everything I’m going to buy needs to go with my hair. That’s how women
think, right? The wig I got was long and strawberry blonde.
Next, I needed a dress that I could wear out on the street. I went through
three stores before I found the right one, a short, tight little black number that
maybe looked more like lingerie than a dress. It seemed fitting. Most of the
prostitutes who stood out on the street wore nothing but lingerie, even when it
was freezing out. Still, I bought a little sheer white number for the bedroom. It
was the sluttiest thing in the whole mall, and it made my new tits look great,
though it didn’t leave much to the imagination.
At the makeup store, I bought one of everything. I had no idea what any
of it did, but I would figure that out later. I also got a perfume that made me
hard. I figured if it could make me hard, it would make whatever John picked
me up hard.
Then I went home, and put it all together. I laid the mascara on thick, and
same with the eye shadow. The lipstick took a few tries, and so did the
eyeliner, but eventually, with the help of a few YouTube tutorials, I got it
looking right. I took a step back and then froze.
I wasn’t staring at Tanner. I was staring at a woman. A hot woman. A
woman with a pretty face, a decent body, and a nice set of tits. I adjusted my
tits and straightened out my dress. I looked too good. I was way hotter than
the whore who gave me a freebie a few days earlier. Hell, I was maybe even
on par with the luxury car whore.
“Shit,” I muttered out loud.
If it wasn’t for the cock stiffening between my legs, pushing tightly
against the thin fabric of my tight dress, I would have passed for a woman.
Even flaccid, my bulge was hard not to notice. Good. I needed something to
let people know I was still packing heat.
The sun was starting to set. It was time for me to hit the streets, to start
earning some coin. I had to walk down the street a few blocks from my
apartment, to the neighbourhood where the homos and trannies hung out. I
needed to make sure I was targeting the right clientele. Also, I didn’t want any
of my neighbours to look out and recognize me—though it was hard to care
about that when my life was on the line. I stood about fifty feet down the
block from another tranny whore. She kept throwing dagger-stares in my
direction, as if I was killing her business—and I probably was. Seeing me
next to her, no one in the right mind would have taken her. Maybe if they
were on a budget.
My heart was pounding relentlessly against my ribcage.
Nearly an hour passed by. I asked one of the other girls for the time. “It’s
ten after seven.” A few cars slowed down, and I got a handful of catcalls, but
no one stopped. There was something about the catcalls that I liked, that made
me feel warm inside. It was nice to know I made a hot woman, and I wasn’t
just another ‘dude in drag.’
Finally, a car pulled up next to me. My heart skipped a few beats and then
started racing again. Despite the fact it was dark out, the driver was wearing
sunglasses. I walked up and leaned into his window, like I’d seen other
prostitutes doing. Then, I was silent. I didn’t know what to do next. I didn’t
know the protocol. “Well?” he said.
“You a cop?”
“No way. You looking for a date?” My voice was shaken. My hands
trembled. But I kept my composure.
“Maybe. What are your rates?”
The man took a deep breath in. “Jesus, a thousand? For the whole night,
“For an hour,” I said.
He was completely silent for a good ten seconds. Then, he sighed. “Okay,
fine. What does that get me?”
I took a moment to respond. Anxiety was overtaking my body, making me
tense. I’d never been with another man before. I didn’t even know whether I
could get a cock up my asshole. I had a girlfriend who would stick her finger
up my ass—even that was a challenge, never mind a whole cock. “Whatever
you want,” I said.
“How much to just let me suck you off?” he asked. “Until you come… On
I thought about it. That’s all he wanted? To suck me off? He didn’t want
to stick it in my ass? He didn’t want to get off himself? “Eight hundred,” I
said. Would I even be able to get off? What if he couldn’t get me off? Would
he want his money back?
“Alright, deal,” he said. “I know a good motel on the other end of town.”
The other end of town was too far. It would be half an hour there, half an hour
back. I didn’t have that kind of time to kill.
“Just pull into the alley,” I said. “You can blow me in the back of your
He pulled into the alley, and I hopped into the backseat. Away from the
safe glow of the streetlights, I became increasingly nervous. As far as I knew,
this guy was a serial killer. He could have stabbed me to death and no one
would have heard a thing. I was totally alone. I didn’t even have a cell phone
on me. Clumsily, he crawled over me and started to kiss my neck. He was
already rock hard, I could feel his cock rubbing up against my leg. “Hey
man,” I said. “If you want foreplay, that’s another hundred.”
He stared at me for a moment with hollow eyes, looking slightly
disappointed and slightly perplexed. Then he shrugged his shoulders and said,
“Okay, fine by me.” And without warning, he pulled up my dress and tugged
my panties down to my knees. His eyes lit up. “Damn, darling,” he said.
“Nice package.” I had an impulse to cover myself up with my hand, but I
fought the impulse back. I tried to remain confident, in control.
I’d never even had a woman look at my cock like that before, never mind
a man. He was a horny fucker, obsessed with my body, obsessed with my
dick. It was slightly disturbing, but also kind of nice. It was nice to feel
appreciated, to feel sexy. He grabbed my flaccid dick and started to massage it
between his fingers. He let out a long, deep groan, as if he’d been waiting a
lifetime for that moment. My body tensed up. It was an awkward feeling,
having my cock massaged by a strange man. He wasn’t exactly gentle,
sometimes squeezing too hard, eliciting an “ouch” out of me.
“Sorry,” he said, and he would be gentle for about five seconds before his
testosterone regained control. I wasn’t getting hard. I was too nervous, too
uncomfortable. He sunk down and slid my cock into his mouth. His mouth
was warm and wet, and he was surprisingly agile with his tongue. But still, I
remained limp. “C’mon, baby. I’m not paying eight hundred bucks to suck on
a limp dick.”
I closed my eyes and took a deep breath. I tried to imagine a woman
between my legs, sucking my dick. It was working for a moment, until he
reached up and grabbed my tit. His hands were big and strong, not at all like a
woman’s hands—making it increasingly difficult to image a woman. Then, I
opened my eyes and looked past the man, at my own reflection in the
window. The man had my dress down over my tits. All I could see in the
reflection was my smoking hot body and the man’s hand fondling my tit. The
sight was strangely arousing. My cock started to harden in the stranger’s
He moaned a satisfying moan. It wasn’t the first dick he’d ever sucked.
He was good at it. Better than most of the women I’d ever been with. As long
as I kept my eyes off of his balding head, I was able to stay hard—and the
man managed to get me rock solid. He finally let go of my tit and then
grabbed my balls. With his other hand, he grabbed my dick, keeping his lips
locked around the tip of my member. He was working me from three angles.
Shit, I thought. I should be paying him for this kind of service. I could
learn a thing or two from his handiwork. Less than a minute later, I gave him
the warning. “I’m going to cum,” I said.
The biggest grin I’d ever seen swept across his face, and he leaned back,
still beating off my dick like some Mennonite butter churn. He pointed his
chin upwards and lined his face up with the tip of my cock. He was ready for
it. And he got it. “Holy fuck,” I muttered as cum began to blast out from my
manhood, onto his face. He moaned and groaned as if he was the one having
the orgasm. He even opened his mouth and let a few shots straight in. Then,
his body relaxed and he sunk back into his seat, that smirk still plastered on
I stared at him for a moment. He wasn’t moving. “Everything okay?” I
He nodded slowly. “Everything’s great.” He reached into his wallet and
dug out a handful of cash.
“Thanks,” I said, getting out of the car before even counting the money. I
didn’t want to count it in front of him. I don’t know why, but it seemed
wrong, insulting. I wanted him to enjoy his moment. I was halfway down the
alley when I finally counted the money. It was more than I was expecting:
$1,200. It was the most money I’d ever made in a night—and the night was
only just starting.
I asked one of the other whores for the time. “It’s ten to eight,” she said.
$1,200 in half an hour, and I got a blowjob. Not a bad gig, I thought. But
$1,200 was nowhere near $90,000. At the pace I was going, I would need to
work about 75 more gigs to break even.
If I was going to make up my debt in just four nights, I needed to up my
game. I needed to go for the bigger clients.
My second client came only thirty minutes later. I upped my rates, seeing
as my last client didn’t take much convincing. I started at two thousand. He
laughed and said, “Give me a break.” He came back at one thousand. “That’s
more than enough, sweetheart,” he said. I considered his offer but decided to
turn him down. A thousand here and a thousand there wasn’t going to get me
up to ninety grand in a few days. I needed bigger. Even two grand didn’t seem
big enough, but it seemed slightly more feasible.
“Sorry, it’s two thousand or nothing.”
He shook his head, drove away, and then pulled back up ten minutes later.
“Okay fine,” he said. “But I get to come wherever I want and I don’t want to
hear you bitching about it later.” I didn’t mind my first client. He was nice
enough, kind of a pushover. This guy was different. He was mean. He was an
asshole. Unlike my first client, he didn’t seem to get much joy out of the
experience. If anything, he acted as if it was a chore, a setback. I didn’t care—
it was his money. If he wanted to sulk around and grumble under his breath,
that was up to him.
He pulled his car into the exact same spot as my first client. “Okay, what
do you want?” I asked. He thought for a moment with a grumpy look on his
face. I noticed the glimmer of his wedding band as he scratched at the stubble
on his cheek. Lucky lady, I thought.
“I want a blowjob. And…” He thought for another moment. “What kind
of toys do you have?”
I didn’t have any, so I just shook my head and shrugged. He grumbled
some profanities under his breath. “Okay, fine. I want you to stick your
fingers up my ass while you suck my cock. Got it?” His face became a shade
of red as he waited for a reply. I tried my best not to cringe at the idea of
sticking my fingers up the man’s asshole, but I didn’t do a great job. His face
became a shade of crimson and then he looked away sharply. “And maybe I
want to stick my fingers in your ass. I haven’t decided yet. Can I play with
That’s where we started. Him carefully pulling down my panties and
fondling my cock. He still had that grumpy look on his face. “You’ve got a
big cock for a tranny. I like that,” he said. But that permanent frown remained
on his face. “Can I lick it?”
He wasn’t nearly as skilled as my previous date. He was a noisy sucker,
slurping and puckering constantly. He only managed to get me half-hard, and
I had to close my eyes for most of it. “Okay, now suck mine,” he said, wiping
the spit from his face. He whipped down his pants and the biggest fucking
cock I’d ever seen in my life sprang out. The thing looked like it belonged on
the National Geographic Channel. Even the veins were unusually thick,
visibly throbbing. He wasn’t even fully hard yet. “C’mon, bitch. Suck it. I
don’t have all night. My wife’s going to start calling soon. She thinks I’m out
I took the massive beast in my hand. It was heavy—like a third arm. I
tried to curl my fingers around it, but they wouldn’t reach. The thing was just
too big, made of cement or something. “I can’t get this in my mouth.”
“Don’t give me that shit. I’ve had tinier whores than you take in the whole
thing. Now let’s go. Suck me off.”
I brought his meat to my lips and opened wide. It just wasn’t possible, not
without some sort of mouth enlargement surgery. But I needed the money, so I
gave it a shot, started stuffing the thing in. I managed to get the tip in, and
then, with my lips stretched as thin as they would go, I got another inch in.
Beyond that, the thing was too big.
His body relaxed somewhat and he let out a long, deep moan. I was doing
something right. I had to use my hand to satisfy the other nine inches of his
cock. It was the first dick I ever sucked. It was the first dick, my own aside,
that I’d ever touched. I kind of liked it—it made me feel in control. His body
responded to every movement I made. Every swift stroke made him relax
back. Every flick of the tongue made his legs constrict tighter around my
body. When I finally got my hand around him, and a finger up his asshole, I
was completely in control. I was like a puppet master. He was like my pet.
I could feel his veins throbbing against my lips. The throbbing became
faster and faster, and somehow, the massive cock in my mouth started to get
thicker, longer. The man reached down and grabbed my head firmly with both
of his hands. Then, he started to thrust himself into my mouth, sinking his
cock in deep, stretching my mouth wider than Mother Nature intended it to be
stretched. He was about to come. I tried to pull his dick out, but he was
locked. He let out a long, deep groan, and then I felt it—warm cum splashing
against the back of my throat. I couldn’t breathe. His load never ended. Shot
after shot. I was going to drown in cum.
With all of my force, I pushed him back. His dick was still firing off
rounds when he hit the car door, all over his lap and his car seat. Even in all of
the porn I’d seen in my life, I’d never seen a man come that much. I leaned
over and spat out what he’d unloaded in my mouth. It was a lot.
“What the fuck?” the man shouted as he sat up and tried to wipe the cum
off of his shirt.
“You said on my tits, asshole. You never said in my mouth.”
“I changed my mind. I think for two grand, I should get to change my
mind if I want to! This shirt is ruined. What am I going to tell my wife?”
“Why don’t you tell her you were cheating on her? Face-fucking a tranny
whore in an alleyway?” I said.
The colour drained from his face and he became silent. After a moment of
stillness, he reached into his wallet and passed me a handful of cash. He
opened the door for me and said nothing as I left. I counted the money in front
of him. Fuck him. He didn’t leave me a tip anyway. I was up to $3,200 for the
night. Still nowhere close to what I needed.
And I was exhausted.
My third client ended up being the last of the night. Like my first, all he
wanted to do was suck my dick. Apparently everyone just wanted to suck a
tranny’s dick. He insisted on a motel, so we went to one that was just down
the street. I fell asleep before I came. I woke up with the sun blaring in
through the window the next morning. He was gone, but he left me a good
chunk of change—$2,500, $500 more than quoted. He also left a pool of dried
cum between my tits.
I took a long, hot shower and thought about what I was going to do. I’d
made $5,700 in one night. Not bad for one night, but I only had three more
nights to make a hell of a lot more and I hadn’t even broken even on my
$10,000 investment yet.
My second night on the street wasn’t much different than my first. Lots of
guys wanted to suck my dick, lots of guys wanted me to suck their dick. One
guy wanted to fuck my tits, which was the easiest $1,500 I’d ever made. I just
sat there holding my tits together while he slid his cock up and down and
eventually came all over my chin. Whatever—it was his money.
I had my first ass fucking. It hurt like hell at first, but it was easy money.
He leaned me over the bed and stuck it in. He wasn’t huge, so it wasn’t so
bad. But by the end of it, my ass was terribly sore from him slapping it.
Goddamn, did he slap the hell out of my ass—and he was a strong guy, too.
He wore a condom, and he was a nice enough man—pretty hot, too. He
looked like he was maybe in the military or something, like he hit the gym
twice a day. Good hygiene. I couldn’t complain. He opened doors for me,
bought me drinks, always asked before doing anything. And he paid three
grand for what ended up being less than thirty minutes of work. Funny
enough, he came back an hour later, picked me up again, and had me fuck
him in the ass. Another three grand. Where the guy got that kind of money,
I’ll never know—I wanted to ask, but I thought that would be rude. He asked
me to jerk him off while I slammed his asshole, so I did. I hardly thrust
myself into him five times before he came all over his own chest. And it felt
good, pushing my dick between those muscular butt cheeks, holding onto his
toned sides. I ended up coming on his cock, which he seemed to like quite a
bit. He tipped me an extra five hundred and drove me back to my corner.
Thanks to a full night’s sleep, I had more energy that night. I was able to
handle way more clients, but I was still nowhere near making the kind of
money I needed. At the end of the night, I counted everything I had from both
nights. $18,000. Not bad, but not enough.
My first client on my third night was a woman, which I thought was
strange. She was an older woman, maybe in her fifties. She was kind of hot
for an older lady, big tits, fit body. All she wanted was to hold my tits while I
fucked her in the pussy. I was ecstatic when she picked me up—I was going
to be paid to fuck a woman. Great. But it wasn’t so great. It wasn’t bad either.
It was just mediocre. When I was with my other clients, there was an
excitement, an electricity. My male clients all wanted me more than they
wanted air. The woman was just another horny lady who wasn’t getting
enough at home, who maybe had some lesbian tendencies she didn’t want to
fully admit to. I don’t know, I’m not a goddamned psychologist. I came on
her big tits. Another two thousand.
When I found my way back to my street corner, I noticed a familiar
woman across the street. It was the luxury whore—the drop-dead beauty who
only went home with the richest men. She was smoking a cigarette, looking
hot. It was the closest I’d ever been to her, and I could practically smell her
perfume from across the street. It was an expensive smell, an irresistible
smell. And those legs—fuck me—those legs. I was tempted to take my
twenty grand and see if I could just get fifteen minutes with the siren.
I watched her closely, observing her mannerisms carefully. I wanted to see
how she hooked the big clients, what she did that was so special (aside from
being the most beautiful woman in the western hemisphere). A Ferrari pulled
up and picked her up. She did nothing but step into the car. Not a word
exchanged. Maybe he was a regular client, or maybe it was just some
unspoken thing. Maybe she could smell the money, and the money could
smell her. Like animals in the jungle.
I was picked up just minutes later. My client’s car wasn’t as nice as a
Ferrari; it was a Ford Focus. He wanted to jerk me off while I jerked him off.
Sure. His grip was uncomfortably tight, and it got tighter the more I beat his
dick. “I want you to come in my mouth,” he said, so I did. He swallowed,
which I wasn’t expecting. “Can I come in your mouth?”
“For another five hundred.” I was hoping he would go for it. Not just
because I needed the extra money, but because I was curious. I wanted to
know what it felt like, having a man come in my mouth (I didn’t count my
first experience, which I could hardly remember because of the shock). My
heart fluttered at the thought and that familiar electricity buzzed through my
body. He didn’t seem too happy about the price jump. His face told me ‘no,’
but the more I whacked him off, and the closer he came to finishing, the more
conflicted he looked.
“Okay, fine,” he said, pulling his dick out from my hand. He stood up
quickly, grabbed me by the back of the head, and pulled me in close to his
crotch. “Open up,” he said through clenched teeth. Then, he came in my
mouth. It wasn’t bad. It kind of tasted like pancake batter. It was warm. I
swallowed, mostly because I thought it would be rude to spit it out in front of
As he dropped me back off at the street corner, the Ferrari pulled up and
dropped off the vixen. She lit up another cigarette and stood there smoking
like a goddamned supermodel. I pulled out a cigarette of my own and tried to
imitate her. Then the thought occurred to me, my chances of surviving had
gone up drastically. I had $22,500 in my purse. That was just two consecutive
wins at the roulette table. My odds of surviving were now hovering around
Knowing my luck, it was nowhere near good enough.
I had a few more clients that night, but overall, it was a slow night. I took
a few in the ass, fucked a few in the ass, sucked a few, and got sucked by a
few. I gave my last client of the night half of his money back because I felt
bad. I could hardly get myself hard, and I couldn’t come. I was drained. The
tap was dry. I fucked him in the ass for about fifteen minutes straight and then
I gave him a hand job. He wanted cum in his ass. He didn’t get it and he
looked upset about it.
I went home early and slept. I had one more night, and I needed to make
about sixty thousand dollars. Fifteen thousand if I felt like flipping a coin at
the casino (I didn’t, but it was nice to have a last resort). I needed a miracle.
I hit the streets early the next night after a quick visit to the adult toy store.
I got an assortment of dildos, vibrators, strap-ons, lubes—and a bunch of shit
that gave me the shivers, but I wanted to be prepared. Leather harnesses,
masks. I even bought a thick, foot long dildo that looked like it wouldn’t even
fit in a horse. I had no intention of it going inside of me. It was my final night
—I needed to maximize profits. I couldn’t miss out on any potential clients. I
was out before any of the other girls. I was out before the glow of the sun had
left the sky.
But still, my night was off to a slow start.
In my first two hours standing out on that corner, I had one client. He
wanted to fuck my tits and stick a vibrator in my ass. I let him do both. The
vibrator felt good, but the guy was a little too aggressive with it, jamming it in
hard and deep. I had to tell him to take it easy, and to use more lube. Thank
God I bought a ton of lube—the industrial strength stuff. It smelled a bit like
bleach. After I had his money and I’d cleaned the cum off of my tits, I hurried
back to the street corner. There was no time to spare.
My second client wanted to eat out my asshole, which probably just tasted
like strong chemicals at that point. Still, he managed to beat himself to climax
while his tongue was an inch down my hole.
I was back out on the street corner before he even had his fly done up.
But the streets were quiet. It was a weeknight—a cold weeknight. I could
feel my nipples stiffening, poking out, trying to break free from my tight little
dress. My whole body was freezing. The other whores weren’t even out that
night—and I couldn’t blame them. But the Johns weren’t out either. It was
starting to look like I was fucked.
Then a set of headlights started in my direction. They grew brighter and
brighter. I perked up, adjusted my tits and then I adjusted my cock. Then I
saw the car. It was a Bentley—a fucking beautiful Bentley, worth probably
half a million dollars. I looked around to see if the vixen was out. She wasn’t.
The car slowed down as it approached me. I couldn’t tell if my shivers
were from the cold or from anxiety. I needed this job. Ford Focus money
wasn’t cutting it. I needed the Bentley money. The Bentley pulled up to me
and the window rolled down. The driver was wearing an immaculate black
suit, fitted perfectly to his athletic, tanned body. I could smell his cologne. It
smelled like mahogany and money. Lots of money. “Hey beautiful,” he said in
a deep, confident tone.
“Hey there,” I said. Nerves were overtaking my body.
“Hop in,” he said.
“Don’t you want to know my rates?”
He laughed. “Don’t worry about your rates.”
I thought of hopping in, hoping he just wanted a blowjob—hoping,
somehow, he wouldn’t notice my dick. He didn’t look like my clientele. He
looked like he was cruising for a luxury escort, not a tranny whore. “I’ve got a
cock,” I said reluctantly.
He was silent for a moment and his expression dropped. “You’re trans?”
“Yeah. You can still fuck me in the ass though.” I was speaking quickly,
desperately. I didn’t want to lose the job. “I can tuck my cock between my
legs if you want, you won’t even notice it.”
He sat in silence for a moment. He scanned the streets, probably looking
for the beauty. “You look pretty good for a trans.”
I was desperate. “I can suck pretty good, too.” I regretted saying it the
moment the words slipped my tongue. It made me sound like a slut, like some
cheap whore. “I really need the money.” I sounded pathetic. “Please.” I hated
myself. I wanted to run away and hide my face. Instead, I just stared at the
man and waited desperately for a response.
After another long moment of silence, he said, “Okay. Hop in.” I did. He
started to drive. The entire trip, he said nothing, and neither did I. I couldn’t
get a read on him. When we drove past the city limit, I started to panic. Even
in the motels and the alleyways, there was a strange sense of safety. Just being
able to hear nearby traffic, see the glow of street lights—that sense of safety
was gone the moment we were beyond that city limit. Everything was dark,
save for the glow from the Bentley dashboard and the pocket of highway in
the Bentley high beams. “You’re going to earn your pay tonight,” the man
said with a smirk. My heart skipped a beat.
We turned off the highway and then drove down a narrow forest road for
another ten minutes. Then, we arrived at a large mansion. Four stories of
windows were dark. Only one window was lit up, and there were silhouettes
moving around inside. It was the biggest house I’d ever seen—if you could
even call it a house. Castle was maybe a better description. The man left his
car in the roundabout driveway and then led me inside. We walked down a
maze of hallways and staircases and ended up in a large library room.
Waiting in the room were two other men, all dressed in the most
expensive suits money could buy. They were smoking cigars, and didn’t
bother to stand up when they saw us enter.
“We’ve got something a bit different tonight,” said the man who picked
“She looks alright to me,” the older looking of the two men said. He had
grey hair and some grey scruff on his face.
“She’s a he.”
The men were silent.
“She said she needs the money, so I figured we would see what she can
“How badly does she need the money?” the clean-shaven, younger man
asked. All eyes turned to me and waited for my response.
My heart stuttered and sunk into my gut. What was the worst they could
do? What could they do that I hadn’t already experienced over the past few
nights? “Badly,” I said. My voice was quiet, sheepish.
The older man stepped up. He scanned my body. He put his hand on my
side and then ran it down to my hip. “Would have fooled me,” he said.
“She did fool me,” said the man who picked me up.
“Well, you are a fool, Aaron,” the older man replied with a laugh. He
brought his hands to my chest and then squeezed my tits. “Impressive. Very
The younger man stepped up. “Let me feel,” he said, taking my tits and
giving them a firm squeeze. I could tell right away that he was going to be
rough. I could practically feel the testosterone through his grip, the way he
squeezed my tits. He reached down and squeezed my butt. “Nice ass, too.”
The two men continued to feel up my body. They didn’t touch my cock. They
were afraid to. Whenever they got close, they retracted their hands and
pretended like they were actually just reaching for my thighs or for my ass.
But I could tell they were curious—the younger man especially. He was
nervous. Every time he looked me in the eyes, he would look away quickly.
His cheeks became red.
“Okay, let’s bring her into the room,” Aaron said.
We went through another set of doors into a dark room. Aaron flicked on
the lights, and the room became lit by a dim orange glow. In the middle of the
room was a black chair-looking thing. It almost looked like a dentists chair,
but smaller. As we walked closer to it, I noticed the hand cuffs on the arm
rests, and then I noticed the ropes hanging from the ceiling, tied like small
nooses. “Sit down,” the older man said, motioning towards the chair.
I hesitated, then thought of the money. Again—what was the worse they
could do? I placed my bag down and then sat down in the chair. Aaron took
my hands and cuffed them to the arm rests. The older man took my ankles
and brought them up to the nooses. I could swing my legs slightly from side
to side, but I was otherwise immobile, paralyzed. I was theirs to do whatever
they wanted. The greying man returned to my chest again and started to
fondle my tits. He pulled my dress down, letting my tits pop out, and then he
bent over to suck on my nipples.
“I’m not cheap,” I said. My body was trembling in fear. “Don’t you want
to know my rates?”
The men all laughed. “I’m sure we’ll survive.”
I could feel my face becoming warm and turning red. “I’m not cheap,” I
said again, sounding like a broken record.
“Didn’t I tell you not to worry about the rates?” Aaron said. His suit
jacket was hanging over a chair and he was undoing his dress shirt, revealing
his chiselled chest.
I tried to swallow the thick lump in my throat.
“I don’t have to remind anyone here that, what happens in the room, stays
in the room. Right?” the younger man asked. His voice was shaken.
“Of course,” Aaron replied. “But I picked her up, so I get to go first.” He
let his pants drop, along with his boxer shorts. He was hung, and already
semi-erect. He stood tall, completely confident in his body, totally
comfortable being naked in front of his friends. He walked around me and
pressed a button on the chair. I started to recline. He let go of the recline
button once my lips were lined up with his cock. “Open that pretty mouth of
yours,” he said. I did, and he slid his throbber into my mouth. “That’s right.
Suck it like you want it.” I sucked it like I wanted sixty thousand dollars.
I could feel the older man’s lips still locked around my nipple, while one
of his hands fondled my tit. I could feel the younger man’s hands exploring
my body, getting closer and closer to my cock. Eventually, he let his fingers
slip over it, and he started to rub it through my dress. He was biting his lip,
staring at my chest, acting as if he wasn’t rubbing a tranny’s cock.
Aaron sunk his cock deeper into my mouth. Too deep. I had the impulse
to pull it out, but I’d forgotten that my hands were locked in place. He
laughed when he heard the cuffs rattling. Still, he kept his member in deep.
The younger man’s hand slipped under my skirt. His face was dark
crimson now, and he was sweating. He grabbed my dick and started to slowly
stroke it. I could feel his hand trembling. He liked it. He wanted it. I could tell
he wanted to suck it. I’d seen that look a half dozen times in the past few
I closed my eyes. The past few days, I’d liked the excitement of sleeping
with strangers, fucking men. There was a harmless fun to it all. But this was
different. This was uncomfortable and overwhelming. I was out in the middle
of nowhere, in someone’s personal home, tied to a sex chair, with three
strange men having their way with me—three men who didn’t give a fuck
about my comfort, my well-being, or my feelings. These were society’s elite
—men who could make any of their problems disappear with money.
Problems which maybe even included dead hookers.
Aaron’s cock sunk down into my throat. I gagged. I couldn’t breathe. But
he held it in place.
The younger man started to fondle my balls. His breathing was shallow,
sporadic. He wanted to suck my cock so badly, but he was afraid—afraid his
friends would think he was gay. Maybe he was afraid I would think he was
gay. Maybe he didn’t want that getting out. How far would he go to make sure
that didn’t get out?
Aaron slipped his cock out from my mouth and I took a deep breath in. I
coughed and gagged. None of the men cared. “Move,” Aaron said to the
younger man, who obeyed the command. It was obvious Aaron was the leader
of the pack, probably the owner of the car, of the house, of the crazy fucking
sex room. He pulled my dress up and ripped my panties off of my body with a
swift tug. He looked down at my cock and smiled. “Nice dick,” he said.
Before I could respond, the older man grabbed my head and turned it onto
its side. His cock was out, hard, and ready to be inside of my mouth. I opened
up and a second later, I was sucking his dick. Thankfully, he was
insurmountably more gentle than Aaron. But the kid was next, and he was
shaking, hardly able to contain his boiling testosterone. The older man was
the calm before the storm.
I felt Aaron push his cock into my asshole. He let it sink in slowly, waited
a moment for me to relax, for me to un-pucker my hole. I closed my eyes and
took a breath. The sooner he got going, the sooner it would all be over. I felt
my asshole unclench, and he started to slide his slick cock in and out.
“She knows how to take a cock,” Aaron laughed. I could feel everything
—every vein, every ridge, every throb—everything.
I kept my eyes closed. The older man slipped his cock out and I took
another series of deep breaths. Then, my eyes still closed, I felt a thick,
bulbous tip press up against my lips. I opened my eyes. It was the kid. He was
rock-hard, and big, like a lead pipe. I could practically see the blood and
adrenaline surging through the veins of his cock. “Open up,” he said with a
coy voice. I opened my mouth wide and he crammed his throbber in. He
grabbed the back of my head with a tight grip and started to fuck my face like
it was a hole in his parent’s couch. I could feel my mascara running down my
face. I couldn’t breathe. I was starting to become faint.
“Let’s make her earn her rate,” the older man said with a laugh. Then, I
felt the tip of his cock press up against my asshole. But Aaron was still inside.
I looked down my body. He wasn’t waiting for Aaron to finish. He was
It was impossible, I thought. My asshole would never stretch enough for
I was wrong.
Somehow, the older man managed to squeeze the tip of his cock in. Fuck,
it hurt. I screamed out loud.
Slowly, the older man pushed himself in deeper. Aaron continued to thrust
in and out, completely unphased by the fact he was rubbing his dick up
against his friend’s. I had two full cocks in my asshole. I was wincing in pain.
My whole body was tense. I rolled my head from side to side, trying to fight
away the pain, but it was hopeless. “Is she okay?” the older man asked.
“She’s fine. She needs the money.” I could see Aaron smirking out of the
corner of my eye.
The older man hesitated, then started to slide in and out, opposite his
friend. I could feel my asshole stretching out, probably permanently. The kid
grabbed my head, held it firm, and stuck his giant cock back into my mouth.
Three. That was the number of cocks I had in my body. I couldn’t breathe.
The faintness returned. The room started to become white and the pain began
to disappear. I was going numb. Maybe I was dying.
I lost consciousness. For how long, I have no idea. A few seconds? A
minute? A few minutes?
When I came back to, there was no cock in my mouth, but the two men
were still fucking me in the asshole. I could hardly feel a thing. The younger
man was straddling me, his ass planted on my belly. “If you won’t suck me
off, at least jerk me off,” he said. I hadn’t realized until that moment that one
of my hands had been freed. Probably while I was out cold.
I wanted to tear his throat out. Of all the clients I’d had, he was the most
ruthless, the most selfish. The rich, spoiled little shit. He was lucky I didn’t
tear his dick off of his body. I took his cock and started to jerk him off. I
gripped him tight, channelling a lot of my anger into his manhood. “Take it
easy,” he said.
“Suck my dick,” I said.
“What the fuck did you just say?”
“I said, suck my dick. I know you fucking want to. Just suck it.”
He stared at me for a moment, his face a dark shade of red. Then, he
turned around, slid back, and bent over, lining his asshole up with my face. I
could feel him lifting up my dick, and then I could feel it sliding into his
mouth. I was right. He did want it. And judging by the way he was sucking it,
like his goddamned life depended on it, he loved it. After a minute of
ferocious sucking, he resurfaced. “Finger my asshole,” he said, and then his
lips locked with my cock again. I followed the order, and stuck two of my
fingers as far up his ass as I could. He moaned a muffled moan.
The two cocks in my asshole were hitting a sweet spot just perfectly,
sending jolts of euphoria surging through my body. My legs started to tremble
uncontrollably. My whole body felt like it was lifting up into the air,
weightless. The kid had my whole cock in his mouth, half of it in his throat. I
was about to come. I decided not to warn the spoiled little prick.
I came in his throat. I was hoping it would piss him off, but instead he
moaned as if he was the one coming.
“Shit,” Aaron said, and I knew already what was about to happen. I could
feel one of the cocks in my ass swelling up, picking up intensity, slamming
down harder. He was about to come. He didn’t pull out, and I could feel my
asshole filling up with his warm juice. The older man wasn’t too far behind.
Before Aaron even finished, he started coming. There were two massive loads
deep in my asshole, being held in place by two massive cocks.
They pulled out in unison, and the massive load of warm, white, sticky
cum poured out. Aaron stumbled back, the kid remained slumped over my
body. Everyone in the room took a few minutes to catch their breath and
gather their composure before muttering a word. My asshole hurt. My head
hurt from lack of oxygen. My wrists hurt from pulling against the handcuffs.
The men seemed satisfied. Thank God, I thought. It was all over. Once
Aaron was able to stand upright, he unlocked my cuffs and released my
ankles. It took me a minute to stand up. Cum was still pouring down my legs,
still trickling out of my asshole.
“What do we owe you?” Aaron asked, walking over to a desk.
“Sixty thousand,” I said without missing a beat.
“Sixty thousand dollars? Jesus—that’s a lot of dough.”
“I tried to tell you my rates. You told me not to worry about the rates.” I
became quickly defensive. I was done for the night. There was no way I could
handle another client. I probably wouldn’t be able to handle another client for
another week. And my debt was due in the morning. I wasn’t leaving that
mansion until I got my sixty grand.
Aaron laughed. “Okay, fair enough.” He pulled a wad of bills out from his
desk and handed them to me. “I’ll give you a ride home.”
The weight of the money was surprising, like the cash was made out of
cement—or maybe my arms were just tired from subconsciously tugging
against the cuffs. I didn’t count it in front of him. I didn’t even count it when
he dropped me off, back at the street corner. I waited until I got home. Sixty
grand is a lot of money, and I wasn’t exactly in the best part of town. There
was street scum that would have killed for that money. I’m sure there were
regular people out there that would have kill for a wad of cash like that. It was
like I’d made two years worth of pay in a couple of hours. Yet somehow, my
ass still sore, thinking of both of those dicks lodged way up my hole, it
When I got home, I counted it. There was ninety thousand dollars in that
wad of cash. Exactly the amount I needed the pay off my debt. It was as if
Aaron knew. Was it possible? Was Aaron part of the mafia? He didn’t look
like a mobster—but who did these days?
I was still in my work outfit when the goomba came to collect my debt. I
was even still in makeup. I didn’t give a shit what he knew or thought. In a
way, I was proud of what I’d done, what I’d managed to accomplish. So what
if I made the money sucking dick and taking it in the ass?
He didn’t say anything as he took the money. He did check me out though,
and it seemed as if he liked what he saw. He left in silence.
After he left, I got a phone call.
It was my insider friend, the guy who gave me the tip on the bum stock.
He was ecstatic, over the moon. “Tanner—you there, buddy?” he said
speaking quickly, as if he’d just done six lines of cocaine. “You there?”
“I’m here. What is it?” I wanted to tell him what I’d gone through because
of him, how little I’d slept over the past week, how many dicks I’d put into
my body. I decided to keep quiet. It wasn’t his fault as much as it was my
fault. I took the risk. I decided to go to the mob for the money. All he did was
give me a tip—although he did say it was a sure thing, the prick.
“The stock—it exploded overnight. I told you it was good. Did I not tell
you it was good? We’re fucking rich, buddy.”
I was silent. My heart sank into my gut. “How rich?” I managed to ask
through the lump in my throat.
“It was at four dollars when we bought in, yeah?”
“It’s up to eighty now, and still climbing.” It was up twenty-fold. My
$80,000 investment was up to 1.6 million. The thirty thousand dollar tip I’d
made the night before suddenly seemed like nothing.
“Are you fucking with me?”
“No. It’s at Eighty-one now. Still climbing!” Another twenty grand.
“We’re rich!” I’d never even heard that kind of excitement out of a child.
I cashed out my earnings and booked the next available flight to
Venezuela. I could finally go back to my real life, my life as Tanner. Except it
would be better than ever. For once in my life, I had money. I wouldn’t have
to whore myself out. I wouldn’t have to make deals with the mafia. I was free
from everything and everyone. But when I got to the airport, I hesitated. I
kind of liked being a woman. I liked the way men swooned over me,
complimented me, held doors open for me. For once I didn’t feel invisible.
Still, I got on the flight.
And two weeks later, when I returned to America, I was a different
person. I wasn’t a T-girl anymore. I was a full-blown woman. I decided to get
the full operation. The hormones, the vagina, the laser hair removal—
everything. The doctor did a bang up job, too.
It wasn’t even an hour into my flight home and I’d joined the mile-high
club. A handsome man ate me out in the bathroom. I don’t know how that
doctor did it, but that tongue felt incredible. For a moment, I was on another
I was happy. Life was looking bright. Brighter than it ever had before.
Since his high school sweetheart, April, left town, Matt’s love life hasn’t
been great. He just can’t seem to hold down a relationship for more than a few
weeks. Not to mention, he seems to be getting more unwanted attention from
men than women — probably because he was cursed with looking like a
woman. No matter how he dresses, how he does his hair, he’s always been
confused as a woman. It’s why his last girlfriend left him — she said so in a
After one breakup too many, Matt has a crazy idea. Why not just embrace
his curse? Why not try out being a woman for a while? With a bit of makeup
and a short skirt, he’s got men drooling over him, and he likes it.
But how far is too far? Are breast implants too far? What about sexual
Everyone remembers their first time. I remember both of my first times;
my first time as Matt, and my first time as Taylor.
My first time as Matt was special. I was young, shy, nervous—it was fast.
It was with a girl I had been dating for months, April, who I’d had a crush on
for years. It was her first time as well. We were both so young, so nervous, so
stupid. We both laughed a lot, took it slow. She was beautiful. Her body was
perfect—thin, tight, supple breasts. I can still remember squeezing her tits,
watching her eyes close as her head rolled back on her pillow. I can still
remember the way her pussy gripped my cock as I slowly slid inside of her,
how her thighs wrapped around my body, how her nails dug into my sides. It
was all over in a flash, but goddamn, I’ll never forget that moment. She was
the love of my life—the girl I wanted to spend the rest of my life with.
But she moved away with her family to London, England a few months
later and I never saw or heard from her again. Life was never quite the same
My first time as Taylor was different. It was exciting, unexpected, but I
definitely wouldn’t call it special. I can’t even remember the guy’s name.
I was sitting in a bar, waiting for my girlfriend, Kylie, to show up. It was
our one-month anniversary. We had tickets to go to the local university
football team’s season opener. I had a gift all wrapped up for her and
everything. I was still Matt—Taylor didn’t even exist yet, but she was about
Kylie and I had been dating for a month. She was a few years younger
than me; she was blonde and smoking hot. Sure, she was a bit of a ditz, but
she was fun. She liked partying, going to clubs, drinking, music festivals—all
of the things girls in their early twenties like to do. I’d never cared for any of
those things, but I liked that she got me out of my comfort zone, and I liked
the sex. It was good at first—things were moving quickly. She was practically
moved in to my apartment after two weeks. But I had a feeling it wasn’t going
to last. Whenever I asked about meeting her friends or her family, she
changed the subject. It had only been a month and she was already ignoring
my text messages. She stopped sleeping over, and eventually, she stopped
coming over all together. I knew it was just a matter of time before she
showed up at my apartment, took her pile of clothes and all of her makeup
and left for good.
Sitting in that bar, I looked down at my watch and I realized Kylie was
exactly an hour late. As I looked back up, I felt the vibration in my pocket,
and a tingle crept up my spine. Somehow, I knew what the message said
before I even pulled the phone out—and I was right.
It was from Kylie. “Matt, I really like you, but I don’t think we’re going
to work out. I’m so sorry.”
I placed the phone down on the bar and stared at it for a moment. I felt
like an idiot. One-month anniversary? How stupid. I felt even more stupid
with the gift bag that was sitting under my chair, inside of which was a Clone
Your Man kit—a kit to make a replica dildo of your cock.
I considered deleting the message, deleting Kylie from my phone, and
pretending like the relationship never happened. I wasn’t too torn up over it;
good sex aside, it wasn’t much of a relationship. There had never been much
of a connection. But I was frustrated. Kylie wasn’t the first girl to break things
off so suddenly. She wasn’t the first girl who kept me away from her friends
and her family. I didn’t want to keep going through the same thing, over and
over again. I needed to know what I was doing wrong.
So I asked, “Why?”
And I got the typical answer. “It’s not you, Matt, it’s me.” And then after
fifteen minutes of back-and-forth, she finally told me the real reason. “You’re
a nice guy, Matt, but I just need someone who’s more of a man.” That shiver
ran down my spine again.
I started getting PTSD-like flashbacks to grade school. “Has anyone asked
you out to the dance yet, Matilda?” “Hey Matt, if Hailey says no, want to put
on a wig and go to prom with me?” “Hey Matt, get your period yet? When are
your tits coming in?” My life was like a running joke.
I looked like a girl. I’d always looked like a girl.
I didn’t matter what clothes I wore or how I styled my hair, I was
constantly being confused for a woman. My voice was higher than the other
guys, I was shorter, my body was more slender. Unless I was looking straight
up, and the light was hitting my neck at just the right angle, you couldn’t even
see my Adam’s apple. Sitting in that bar, I could still hear the voices of my
classmates ringing in my head. Those voices were responsible for years of
depression and a lifetime of social anxiety.
“Just ignore them, Matt,” my dad always told me. “Just embrace your
differences.” Easier said than done, Dad.
I could feel that familiar depression creeping back inside of me. When the
bartender walked past, I was quick to order a double whiskey, neat. “And
keep the tab running,” I said before the bartender was out of earshot.
Watching the bartender pour my drink, I could only think of April—the
only girl who didn’t care about my higher voice, my height, or my smooth
neck. Why did she have to leave for London? Why did she never come back?
Why did she never reach out? I brought my drink to my lips and let the burn
trickle into my mouth.
“It’s not too often you see a young lady ordering whiskey,” a deep voice
said. A few seats down to my side was a tall, muscular man. His skin was
dark from sun exposure, and his clothes were dirtied and ratty—probably his
work clothes from some labour job building houses or digging ditches. He
had a smile on his face, a genuine smile. A part of me wanted to tell the guy
to go fuck himself, but I kept my cool. I thought about telling him I was a
man, but then I considered the ensuing humiliation for both me and him. So
instead, I just smiled and said, “Thank you.”
It’s strange. On days when you’re feeling exceptionally self-conscious, it’s
as if you can hear your own voice, the way others hear it. It’s an
uncomfortable, unfamiliar thing, like listening to a recording of yourself. It
was true, I did kind of sound like a chick.
The man was looking down at my drink, which was now just an empty
glass. “Rough night?” he asked.
“Something like that.” I could feel the liquor seeping into my veins, into
The man waved down the bartender. “Excuse me—could I get another
beer, and another whiskey for the lady?” He looked back at me. “I hope you
don’t mind—I know what rough days are like.” He smiled again and his eyes
flashed. I wanted to be angry with the man but I couldn’t do it. He wasn’t
doing anything wrong. He wasn’t calling me ‘sugar’ or grabbing my ass (all
experiences I’d endured before). He was just being a nice guy. He told me his
name and then asked, “What’s your name?”
There was a Taylor Swift song playing on the radio. “Taylor,” I said
before I had a proper chance to think. I felt my heart sink into my gut—I was
actually doing this, I was actually pretending to be a woman. A strange rush
charged through my body. Maybe it was the alcohol, or maybe it was some
sort of perverse excitement, knowing I was doing something wrong—
“Are you cold?” he asked.
I looked down and realized my hands were trembling with nerves. I could
feel a warmth in my cheeks. “Yeah,” I said, sinking my hands between my
The man smiled, stood up, and took off his jacket. “Here,” he said,
placing it over my back before taking the seat next to me. “You don’t mind if
I sit here, do you?” Again, I wanted to be angry with the man, but he was
being so polite, so charming. I went to take a sip from my drink but just ended
up lifting an empty glass to my lips. At some point between realizing my
hands were shaking and when the man took the seat next to me, I’d managed
to finish another double whiskey. Though I couldn’t remember drinking it, I
could already feel it leaking into my veins, numbing my senses, dulling my
“I hope you don’t mind my saying, but you’re very beautiful, Taylor.” He
smiled and I blushed. The night became a haze after that. I remember the
bartender placing another drink down in front of me. I remember the man’s
hand finding my shoulder as we did a shot together—and another shot
together. I remember him laughing—and I remember laughing with him.
And the next thing I remember is stumbling into the bathroom, towards
the sink. I stared at myself in the mirror and it was like staring at a stranger. I
wasn’t staring at Matt. I was staring at a woman, I was staring at Taylor.
Then, the door opened and the man stumbled in. I froze, realizing I was in
the men’s bathroom. It took him a moment to realize I was in the room, and
then he froze and looked around. “I’m sorry. Did I walk into the wrong
bathroom?” he asked.
I looked around and faked a laugh. “No, I think I did. I’m sorry.” I started
towards the door, my heart pounding against my chest. The liquor was still
surging through my body, controlling everything.
As I walked past, he grabbed me, spun me around, and kissed me on the
lips. He was powerful, like I was hardly a ragdoll in his arms. By the time I
realized what was happening, I was already kissing him back. There was a
strange comfort in being held like that, in those thick arms. There was a
strange comfort in the way his stubble brushed against my face as his tongue
slipped through my lips. I put my hands on his arms and suddenly felt tiny,
unable to extend my fingers around even half of his rock-hard biceps.
The thought occurred to me: if he found out I was a man, he could have
destroyed me, squashed me like a bug.
He pulled back and shook his head, his face suddenly a shade of crimson,
guilty. “I’m so sorry. I don’t know what came over me,” he said. “You’re just
—you’re just very beautiful.”
I could feel that warmth glowing in my cheeks again—a feeling I hadn’t
felt since high school, since I was with April. It was nice to feel admired and
appreciated, even if it was for the wrong reasons, for being someone I wasn’t.
I thought about leaving—the bathroom was just steps from the backdoor. But
the liquor was in control of my body, not me. I stepped forward, wrapped my
arms around him, and kissed him again. I ran my hands down his sides,
feeling the rigid curves of his muscular body. The moment became a blur.
His hands found my shoulders and then I could feel myself sinking down
to my knees. He was pushing me down. My fingers found his belt buckle and
the next thing I knew, his belt was on the floor, next to my knees, and I was
pulling down his fly.
My heart was tolling like a church bell against my ribcage. What the hell
was I doing? Why was I letting myself do this? His pants dropped down to his
ankles, and then I saw the bulge growing, pulsing against his boxer shorts. It
was huge, becoming massive. I froze again.
“What’s wrong?” he asked between heavy breaths.
I looked up and forced a smile. “Nothing.”
I slowly lifted my hand to the stiff rod and carefully wrapped my fingers
around it. I had never touched another man’s cock before. It was warm, solid,
throbbing. He let out a long sigh of relief the moment my trembling fingers
were around the beast. I froze yet again. “It’s not going to bite,” he said with a
I thought about running, but his back was against the door. “Fuck, you’re
beautiful,” he said. I couldn’t run. For the first time since I could remember, I
was being complimented, not criticized. I began to stroke his cock through his
boxers. Somehow, it became bigger and harder, a warm lead pipe in my hand.
Everything about the moment was crazy—I was drunk, I’d completely
lost my mind. Matt was gone. There was only Taylor there in that bathroom.
He pushed my hand away and, without warning, dropped his boxers to his
ankles. His hard cock sprung up with force. I could feel my own bulge
beginning to harden and press up tightly against my underwear. My heart
skipped a beat—what am I going to do when he wants to get into my pants?
What will I do when he realizes I have a cock between my legs, just like him?
His fingers slipped around the back of my head and he pulled me in close
to his massive manhood. “Go ahead and suck it, baby,” he said. I took the
thing in my hand, head spinning, brought the tip up to my lips, and opened
wide. Before I could hesitate, he pulled me in, slipping his throbbing dick into
my mouth. The intense girth of it stretched my lips thin. I could feel every
ridge and vein of his cock against my tongue, my cheeks, and the roof of my
Some alien instinct took control. I started to suck him off. I sunk his
member as far towards my throat as I could handle, before gagging him out.
What I couldn’t fit into my mouth, I clasped with my hand, and I beat him off
while I sucked his cock. My head was still spinning and my heart was still
rapidly tolling. A strange thought occurred to me—if I get him off in my
mouth, he won’t want to get into my pants, and then he won’t have to see my
cock. He won’t find out I’m a man. For some reason, in my state of
intoxication, the thought was solid and sound. I sucked him harder, and
pumped him faster.
He stumbled back into the door, but I never lost my hold on his member.
“Holy fuck,” he muttered, his legs trembling. I could feel his cock swelling,
his fingers grabbing my hair, which hurt, but in that moment I didn’t care.
“Shit!” he moaned with a deep sigh.
As I leaned back for a quick breath of air, without warning, he came on
my face. His cock unloaded blast after blast of hot cum on my cheeks,
forehead, chin, nose. I shut my eyes tight and winced away from the barrage,
but it was too late. I was covered in his load.
He was panting and I was rendered frozen. The reality of the situation
came rushing in. All he had to do was look down and he would have seen the
massive bulge of my own cock pushing out from my pants. Thankfully, he
was in his own state of drunken euphoria. “I’m sorry,” he said, looking down
at my cum-soaked face. He blushed.
Despite everything, I couldn’t help but smile. The exhilaration was still
like an electricity inside of me. He left me alone to clean up. When I was
done, I slipped out the back door and never saw him again.
“I will never do that again,” I told myself as I walked into my dark
apartment, still shaken with excitement. But as I lay down in my bed, I
couldn’t help but think of Taylor—who she was, and who she could be.
The next morning I packed all of my now ex-girlfriend’s things into a box
and put it by the door for her to come pick up. She never came to pick it up.
It was a few months after the incident at the bar that I realized Taylor was
starting to take over, whether I wanted her to or not. It was like a part of me
was boiling up to the surface, silently—so silently, even I didn’t notice it at
first. My hair started growing longer, but I didn’t stop it. I liked it long. I even
went into the barber to get it cut off, but ended up asking for a dusting—
hardly a trim.
I started taking a different route home from work every day. I thought I
just wanted a change of scenery. But the route I was taking just happened to
pass by a new clinic—one that specialized in female enhancement and sex
reassignment. I would stop and stare at the building and I would remember
that night as Taylor. Maybe I took the route on purpose, subconsciously
wanting to check out the clinic.
I watched people leaving the clinic—people who were once men and were
now women. They never looked like women to me. They looked like men in
drag with fake tits. Hell, I looked more like a woman than any of them. I
looked more like a woman than some of the naturally-born women who
walked out from that clinic with their new, bigger breasts.
One day, as I stood outside the clinic, a car full of teen boys pulled up to a
red light. They looked over at me and then one of them whistled. Another
yelled, “Show us your tits!” I just stared back, feeling angry, humiliated. Even
after hearing the same catcalls my whole lifetime, it still stung. That evening,
I got home and looked myself in the mirror. I wasn’t staring at Matt. I was
staring at Taylor. I could feel a pit in my stomach. I saw men with long hair
all of the time who still looked like men. I didn’t. It didn’t help that I couldn’t
grow any facial hair to save my life.
As I stood there, staring at Taylor in the mirror, I could hear my dad’s
voice echoing in my head. “Embrace your differences.” I don’t think he was
ever saying ‘just be a woman,’ but it was starting to seem like that was the
only answer. The image of that reassignment clinic crossed through my mind.
I didn’t want to undergo sexual reassignment surgery. I didn’t want to lose
myself just because it would make life easier. But something deep inside of
me wanted to be Taylor, wanted to see what life would be like as Taylor, not
Matt. I was sick of Matt.
I found myself looking at the clinic’s website. Reassignment surgery was
out of the question, way too expensive, and the post-result photos weren’t
exactly the most convincing images I’ve ever seen. Breast implants weren’t
too bad—a few grand and they looked pretty good.
I tried to pull myself away from the mirror, to watch some television, to
get my mind off of all the nonsense. I wasn’t actually considering becoming a
woman, was I? As I flipped through the channels, I landed on the E Channel.
Ryan Seacrest was interviewing Taylor Swift. She looked good. I thought her
makeup was nice and her hair was nice. Her hair was about as long as mine.
The box of my ex-girlfriend’s things caught my eye, pulling my attention
away from the television. The next thing I knew, I was digging through the
box, pulling out makeup, clothes, and a hair straightener. I spent the next few
hours in the bathroom, straightening my hair, putting on eye-liner, mascara,
eye-shadow, and so on. I wanted to see what Taylor could be, what she could
look like with a little bit of effort.
The bra Kylie left behind was heavily padded (she didn’t have much of a
chest) so I didn’t have to do much in terms of stuffing. I loved the way the
black lace panties hugged my cock tight against my body, and the way her
white stockings squeezed my legs. When I put on the skirt, I started to get
hard. The panties didn’t do much in keeping my cock down. It sprung out and
pushed the skirt outwards like a stray tent pole. Kylie left a sheer lace top
behind—one I’d always thought made her look like a slut (it didn’t leave
much to the imagination). But the moment I slipped it on, I understood why
she liked it so much. It made me look hot. My dick got harder, bigger, and
taller; the tip of it poked out from the bottom of the short skirt. Was I making
myself horny, or was it just the excitement of being so hot, of knowing what I
could do with this kind of power?
I looked out the window at the club across the street, the club I had only
ever been in once, with Kylie. The line-up was down the street—all twentysomethings,
mostly men. The women all walked up to the bouncer, and only
the hot ones got through. The others were sent to the back of the line. I
wondered, if I went down there now, would I get through?
If I did get through, then what? See if men would buy me drinks? How far
could I go? What if I ended up back in the bathroom with one of them? My
heart began to race. What if they wanted to fuck? Would I do it? Could I
somehow hide my big cock? I bet if I just pushed aside my panties, a man
could get his dick into my asshole without even coming near my cock. Now
my heart was pounding and my forehead was hot.
I shook my head. Was I seriously considering letting a man fuck me in the
ass? I looked in the mirror. I was blushing—Taylor was blushing. And damn,
was she hot—even with the raging-hard boner sticking straight up through her
skirt—my skirt. I’d never had so much as a finger up my ass, never mind a
Why not give it a try?
I lay back on my bed, flipped my skirt up onto my belly, and I grabbed my
member in my hand—not my own member, but the one I’d cloned for Kylie
—the rubber dildo replica of my own manhood that never made it out from
the gift bag until that moment. I slipped my panties down to my knees,
squirted some lube onto the tip of the sex toy, and then brought it down to my
asshole. It didn’t seem possible, the thought of getting the whole thing in
there, through my tight little hole. But women did it all the time, right? How
hard could it be?
I closed my eyes and rolled my head to the side. I pushed it, twisted it,
tried a few different angles, but I couldn’t seem to get past my clenched
asshole. I needed to relax. I tried taking deep breaths. I managed to get the tip
of it in, but that was it. Then, I opened my eyes and found myself face-to-face
with Taylor in my closet mirror. Suddenly, the cock slipped in deep—and I
could feel it the whole way, stuffing me tight. My eyes shot open wide. I froze
for a moment and clenched tight on the toy. “Holy shit,” I heard myself
mutter, slowly sliding the fake cock out of me. I pushed it back in, this time
deeper. It felt incredible. I let my head sink into my pillow and I watched as I
fucked myself in the asshole, my big dick laying hard on my stomach.
Faster, faster, faster. I needed it deeper. I needed it harder. I started to beat
myself off while I fucked myself in the ass. “Oh my God,” I repeated over
and over. I could feel the most intense orgasm coming on, drawing closer and
closer. I could feel my cock swelling up in my grip, my anus tightening
around the sex toy. I looked to the mirror. I wanted to watch Taylor come on
herself, on her face, on her belly, on that skirt. But I wanted the moment to
last, so I held on. I held on as long as I could, pumping my dick faster,
holding tighter, drilling my dildo harder into my asshole.
Then, I burst. Cum sprayed my face, my top, my tummy, my skirt—
everything. I watched myself in the mirror. I was beautiful, sexy, naughty. My
heart was racing, my head was spinning, everything seemed right. This was
who I was meant to be—I was a woman, I was a slut, I was Taylor.
It took a week to finally build up the courage to go down to that club.
Walking up to the bouncer, my mind was flashing with anxieties. What if he
told me to go to the back of the line? What if someone could tell I was a man,
even through the clothes and through all of the makeup? What if I ran into
someone I knew—someone from work? I would never be able to show my
face at the office ever again—or would they even recognize me with my
makeup and my guise?
“Hi,” I said sheepishly to the bouncer.
He looked me up and down and then a grin swept across his face. My
heart fluttered, and then he said, “Go ahead.” He pulled away the little red
rope and I was inside. My heart calmed down some as soon as I was inside. It
was dark, save for the flashing coloured lights at the dance floor. As I scanned
the room, I caught a good share of glares in my direction, glares from men
scouting out their prey. I was alone; I was an easy target. The only question
remaining was, would they go for me? Would I pass the real test? Even that
anxiety fluttered away after I caught a glimpse of myself a nearby mirror. I
was a babe—hotter than most of the girls in the club.
It didn’t take long for the affirmation. A man reached a drink out in front
of my face. “For you,” he said simply. I looked at the man. He was good
looking enough, tall, clean-shaven, drunk. I didn’t know what the drink was,
but I accepted it. As I did, he smiled as if he’d won. “Steve,” he said with an
aura of confidence.
Three drinks later, we were in the bathroom. His hands were all over me,
up my shirt, down my skirt. His fingers weren’t far from my cock. Whenever
they got close, I would lead them away. After a few minutes, I’d gotten pretty
good at it. It helped that he was an ass-man, obsessed with squeezing my ass
and flirting the tip of his finger over my asshole.
Club-goers were walking in and out of the bathroom casually, as if we
weren’t even there, as if it was a regular sight at the club, seeing people
getting busy right in the open in the bathroom. Even once his rock-hard cock
was out, and I was down on my knees with half of it in my mouth, no one
batted an eye.
Steve was more aggressive than my first a few weeks earlier—more
careless. He held my head in place and thrust his cock into my mouth as if I
was some glorified sex toy. I couldn’t help but gag all over his dick, but he
didn’t seem to mind. If anything, it just got him harder, made him want it
more. He held my hair tightly, nearly pulling it out from my scalp. It hurt like
hell, and kind of pissed me off—I’d spent all evening getting my hair right,
making sure every strand was perfect. Now, it was a flustered mess, nothing
more than something for the horny bastard to hold onto.
When I finally had a chance to pull back for air, he pulled me up to my
feet with force. I would have fallen on my ass had the horny fuck not pinned
my chest to the bathroom wall. My trembling legs were much more of an
issue that night. I was in a pair of high heels that were two sizes too small—
and it was the first time I’d ever worn heels.
His fingers found the waistline of my panties. I swatted him away. “No,” I
said. If the panties came down, my dick would spring out. I’d be dead.
Instead, I pushed aside the thin piece of fabric covering my asshole. “In my
ass,” I said. “I want you to fuck me in the asshole.” My voice was shaken—
my whole body was shaken. But I had to sell it, I couldn’t let him think there
was any other option.
“Fuck,” he said with a laugh as he lined up the tip of his slobber-covered
cock with my tight hole. “You’re such a fucking slut.”
Steve had a big cock, much bigger than the clone I’d been practising with
all week—the clone I could hardly squeeze into my asshole to begin with. But
I had no other choice—I didn’t have a pussy after all, not yet.
He pushed himself in and it hurt like a sonofabitch. He didn’t bother to
take it slow, to be gentle, or to mind my comfort. He just pushed it in, all the
way until his abdomen was pressed up against my butt cheeks. I screamed—I
couldn’t help it. I never even got my rubber clone in all the way, never mind
Steve’s rock-hard monster cock. He just laughed, slapped my ass, and then
started to pump his member in and out of my body. I swear I could feel it
pushing against my belly like some kicking fetus.
I didn’t realize I was crying until I looked over at the mirror and saw that
my mascara was running down my cheeks. Shit. I wasn’t prepared for this—I
had no idea what it was actually like to be dominated by a man.
Two men, who had just finished taking a piss, stopped to watch Steve
pound my asshole. One had a cell phone out, taking a video. The other had a
mesmerized look on his face. We were like animals at the zoo, on public
display. “Look at her take that dick,” one of the men said.
“Holy fuck, she’s so hot,” said the other. “Lucky bastard.”
Finally, through the pain, I felt that warm glimmer of satisfaction I’d
come to the club in search of—that confirmation that I was sexy, that I didn’t
just pass as a woman, that I could pass as a beautiful woman, a woman that
men wanted to fuck, that men could get jealous over. And just like that, the
pain seemed to subside. Suddenly, Steve’s monster cock felt incredible,
euphoric. I started to push my ass back into his pelvis along with every thrust.
I could practically feel the tip of his dick up at my throat, and I loved it. I
could feel everything, every throbbing vein, every muscular ridge. I could feel
it bloating thick as his thrusts became harder, swifter. He was about to come.
“Fuck!” he screamed.
Shots of warm, gooey cum filled my asshole. Every heavy shot was its
own confirmation. The night was a success. I knew it was time to let Taylor
out permanently. I knew what I needed to do next.
After my consultation, it was a three week wait to get into the operating
room. After a quick, anaesthesia-induced nap, I was the proud owner of a set
of very convincing B-cups. The doctor said it would take a few days for them
to “relax” and feel more like real breasts. I thought they were already pretty
good, but he was right. After a few days, they were totally convincing.
I went with the B-cups because I knew that I could hide them for work. I
just needed a tight band, and they were invisible, flat against my chest. I was
already looking for a new job. Once I found one, I would only be Taylor, no
more Matt. Matt was quickly fading into obscurity, into a distant memory. It
was incredible how comfortable I was as Taylor, how little I thought about
how I looked, what people thought when they saw me. I never had more fun
in my life shopping for makeup and outfits at the mall. I spent days trying on
different dresses and skirts. From time to time I had to hide in the dressing
rooms because my cock would get so hard against the thin, tight fabrics.
My asshole was also getting more used to being Taylor. Every few nights
I would venture back down to the club and I wouldn’t have to wait long for
the men to swarm me. Then, I picked my favourite and made a trip to the
boys’ room where I got pounded raw. One man even ate out my asshole for a
good fifteen minutes, which felt incredible.
I cleaned up my apartment and took out all the obvious evidence,
replacing it all with girly things like candles and flowers. It was actually quite
nice. I even got a few throw pillows for the couch, which I accidentally ruined
a few days after I bought them. I brought a man home who wanted to fuck me
on the couch. By the end of the night, the pillows were covered in apparent
teeth marks from where I’d been biting them. The cushions were also ruined
that night after my date pulled out to come on my back and missed. I had to
pull the covers off of the cushions and bring them to the drycleaners. I don’t
think the drycleaners believed me when I said I spilled a milkshake.
One night, as I was scanning the options in the club, I saw a familiar face.
My heart sank into my gut. It was April, the girl who owned my virginity, my
first love. My body became stiff, paralyzed. That familiar self-consciousness I
felt every day as Matt came back with a vengeance. I should have made a run
for the exit, but before my mind could process the situation, she saw me. And
as her eyes locked on me, she became still. Did she recognize me through the
makeup, through the clothes, through the implants? I stood still like a
demented deer in the headlights.
Then, a man stepped in front of me, blocking my view of April. “Hey
darling,” he said. “Care to dance?”
“I’m sorry, I can’t right now,” I said, stepping past the man. But April was
gone, lost in the crowd, or maybe she took off. I needed to give myself a
chance to breathe, to get a hold over myself. I headed for the bathroom and
took a long look at myself in the mirror. Could she have recognized me? It
seemed impossible—even I could hardly recognize me, and April hadn’t seen
me in nearly a decade. Maybe it wasn’t even April—just a girl that looked
like her. After all, last I’d heard, April was halfway across the world in
Just as an ease began to fill my body, April stepped out from one of the
bathroom stalls. She walked right up next to me, turned on the sink, and
started to wash her hands. Once again, I was rendered frozen. It was her—it
was definitely her. It may have been a decade since I’d last seen her, but that
was a face I would never forget. She looked up at me and smiled. “Hey,” she
said with a nod, and then she looked back down at her hands.
“Hi.” My voice was timid and quiet.
“I love your shoes. Where did you get them?” she asked.
My mind drew a blank. It took me a good five seconds before I processed
her question. “Um, some place downtown. I can’t remember the name.”
“They’re lovely.” She had a slight British accent to her voice, one she
must have picked up over the years living in London. She looked up at me
and smiled and I felt that constriction overtake my muscles. “God,” she said,
looking me up and down.
I couldn’t move. If she hadn’t recognized me yet, it was only a matter of
time. She was standing less than five feet away, staring directly at me in the
even bathroom lighting. “Huh?” I managed to say through my crippling
“I don’t envy you,” she said. “Men must be all over you, all the time. It
must be exhausting.” She gave me another look, up and down. “You’re
My cheeks became crimson. “Oh please,” I said.
“Seriously. I don’t think I’ve ever seen someone so… so beautiful. I’m
sorry—am I being a weirdo? I’m not trying to make you uncomfortable.” She
could obviously see that my face was as red as a beet.
“No, it’s okay.” She was just as gorgeous as the day we made love. A
compliment from her meant one hundred times as much as a compliment
from one of the many horny men crawling around the club.
“But my God, do you look familiar,” she said, and for a moment my heart
stopped beating. “Have you ever been to London?”
After a moment of complete paralysis, I shook my head.
Then, her eyes became wide and the room became silent. That was it—
she figured it out. I knew it was only a matter of time, and I was right.
“Wow,” she said, eyes still wide, still not having blinked. “You…”
I couldn’t think of anything to say. I wanted to throw up. I wanted to run
out of the bathroom crying. How humiliating, being seen like this by my first
“I’m sorry, you just look exactly like someone I know,” she said. She
didn’t take her eyes off of me. “What did you say your name was?”
I considered fessing up—it seemed pointless to try and hide it at this
point. But I couldn’t bring myself to do it, I couldn’t let go of the hope that
she didn’t know who I actually was. There was still hope. “Taylor,” I said.
I managed to smile through my dizziness.
“Are you okay? You look sick.”
I was sick. And after quick glance in the mirror, I saw what April was
seeing—I was greener than fresh broccoli.
“Is it your stomach? C’mon, I know a place nearby that makes a
peppermint tea. It’s seriously the best cure for nausea.” She took me by the
hand and began to lead me out from the bathroom. Her hand was soft, warm,
and gentle. She led me out from the club, down the street to a little café that
was totally empty, save for the barista who was half-asleep behind the
counter. “Just take a seat,” she said, motioning to a small chair at one of the
small tables. She continued onto the counter to order my tea.
I pinched my arm and whispered, “Wake up.” I didn’t know whether I
wanted the whole night to have been a nightmare, or if I wanted to erase the
entire past two months. I liked being Taylor, but only because being Taylor
filled me with that comfort and satisfaction I got when I was with April. As
Taylor, I couldn’t have April. As Taylor, all I would get were the horny men
looking for a quick fuck in the men’s’ bathroom. I could never have a real,
meaningful relationship—not without going through with the full
reassignment surgery and hoping that I could find a man stupid enough to not
be able to tell the difference between a real pussy and the fake one I would be
April placed a large steaming paper cup down in front of me. “Drink that.
It will make you feel better.” She smiled, and I accepted the drink. She was
right—at least, a little bit. The tea helped the nausea, but it didn’t help that
looming dread—dread that I was never going to be happy. I could never have
April and Taylor. I would have to pick one. And even if I left Taylor behind, I
might still never have April. As far as I knew, she already had a boyfriend—
or maybe even a husband. As far as I knew, she was married with kids, just
visiting for a few days before disappearing again to London or God knows
“I know I keep saying this, but you really are beautiful,” she said. “What I
would do to look half as good as you…”
“Please. I think you’re beautiful.”
She laughed. “Were you just at the club alone?”
I thought for a moment before answering. “Yeah,” I said, and then
immediately looked away. I was practically admitting I was a slut, just out for
an easy fuck. Why else would a girl go out to a club crawling with hot young
men by herself?
She laughed, clearly seeing through my insecurity. “That’s okay. I was
there alone too. I’m actually glad all of this happened. At least now I don’t
feel like such a loser. I’m new to town. I just moved here from England.”
“Moved?” I asked.
“Just two days ago. I’m living nearby in some gross hostel. I’m basically
doing whatever I can to avoid going back there.” She laughed again. Her
laugh was so adorable, just like when we were in high school. “I grew up here
—I moved away during high school.”
“Why did you move back?” I asked.
She pressed her lips thin and then blushed. “It’s a long story.” I stared at
her. What was that? Why was she blushing?
Before I could prod further, the barista walked up to our table. “I’m
terribly sorry—I’m closing shop for the night, ladies.”
We stood up, taking our drinks with us. “I guess it was just a matter of
time before I had to go back to the hostel,” April said.
I offered up the couch in my apartment. “It’s not the most comfortable
thing in the world, but it beats a hostel,” I said.
She smiled and bit her lip. “You really don’t mind?” she asked.
“Of course not.” We headed back to my apartment. As I slipped my key
into the front door, I realized my real name was on the apartment directory.
All she had to do was quickly scan the list and she would see it—then there
was no backpedalling. Thankfully, I was quick with the door, and she didn’t
notice the directory. As soon as we were in the apartment, I quickly grabbed
all of my mail and old paystubs and stuffed them into a drawer. Before she
even had her heels off, I’d done a full loop around the apartment, making sure
there was no evidence of my real identity anywhere.
“Nice place,” she said. “This is exactly what I’m looking for.” She walked
up to the window and looked down at the club.
“It’s got a lot of space, but it can get noisy with that club down there,
especially on weekends.”
“That’s okay. I can sleep through anything.” She grabbed the base of her
shirt and lifted it up over her head, leaving her standing in only her bra. Then,
she reached around her back and unclipped her bra, letting it fall to the floor.
She had a beautiful set on her—bigger than I remembered—still perky and
supple. “Oh, that feels good. I’ve been waiting to get that off all night.” She
stretched out her back and let out the cutest little sigh.
I stood frozen like an idiot. I could feel a tingle running through my body,
all the way down between my legs. My cock began to throb and grow. “I’ll
get you a blanket for the…” Before I could finish my sentence, I noticed the
couch had no cushions. They were still at the drycleaners. Shit.
“I don’t mind just sleeping on the floor,” April said with a laugh.
“No, no. Take my bed. I’ll take the floor. They say it’s good for your back,
She stepped into my bedroom and smiled. “Hey, don’t be silly. Your bed is
huge. We can just share it.” She sat down on the bed and let her body fall
back. Her perfect tits jiggled and then settled on her chest as she sprawled her
arms out. “Your bed is amazing. I forgot what a real bed was supposed to feel
like!” She closed her eyes and took a deep breath. “God, I’m exhausted.”
I had to step back into the living room, out of April’s line of sight, to
adjust my cock in my panties, pressing it up against my thigh. The bulge was
still apparent, so I slipped into the bathroom and gave it a moment to calm
When I slipped back into the bedroom, April was asleep. I crawled into
the bed next to her. I could feel the warmth emanating off of her body. I could
smell her subtle but mouth-watering perfume. I couldn’t sleep. My head was
swirling, still in a state of complete disbelief. Not only was April back in
town, she was in my bed. But what did it mean? What could I do about it?
I couldn’t have her.
She rolled over in her sleep. As she did, the blanket inched down her
body, revealing her perfect tits. I just wanted to reach out and grab them,
squeeze them, feel her nipples between my fingers, between my lips. I wanted
to feel her soft lips between mine, I wanted to kiss her neck.
Carefully, I reached over and rested my hand on her sternum. I waited a
moment in case she woke up. I could play it off as if I was asleep. She didn’t
wake up. So I carefully slid my hand upwards, onto one of her breasts. It was
soft; her nipple was hard. She remained asleep. Gently, I fondled her chest.
Fuck, it was so soft, so supple.
Suddenly, she rolled towards me, her face landing just inches away from
mine. I retracted my hand as fast as humanly possible. Thankfully, with a
precious smile, she was still asleep. I brushed a strand of her hair from her
face. Her skin was perfect, smooth, glowing. She looked like an angel, like
she hadn’t aged a single day in the past ten years. She reached a hand over me
and snuggled in close to my body, her warm skin pressed up against me. She
let out a cute little sigh, still asleep.
Heart beating fast, I ran my hand up her back, into her hair. I knew I
should have stopped—I should have rolled over, closed my eyes, and gone to
sleep. But I didn’t. I couldn’t help myself. I needed to have her. I needed to
touch her, to feel her body.
Goddamnit, Matt, get a grip over yourself, I thought. I pulled my hand
back and took a deep breath. I closed my eyes and started counting to ten.
Suddenly, her lips connected with mine and she kissed me. I froze. She
ended her kiss with a gentle bite, pulling my bottom lip out a bit before letting
go. It took me a moment to open my eyes. Her eyes were open, staring into
mine. Her cheeks were red. She bit her lip. She could probably hear my heart
chiming into my chest. She looked like she was about to apologize, but I
didn’t give her the chance.
I pulled her in close and kissed her, wrapping one hand around her head
and one around her back. She kissed back, wrapping both of her arms around
my body, along with her legs. We were locked together, her breasts pressed
tightly up against mine. Fuck. If this was a dream, I thought, I didn’t want it
to end. I couldn’t let it end.
She rolled over me and planted her hands firmly on my chest. She
squeezed my tits. It felt amazing. She leaned forward and plated her forehead
against mine and I could hear her breathing heavily, euphorically. I reached up
and did the same, fondling her chest, playing with her nipples between my
fingers, feeling them becoming firmer and firmer. If there was a heaven, this
was it. I had everything I’d ever wanted. I had Taylor and I had April. With
my hands on her chest, I could feel her heart racing.
I pulled her panties down swiftly and she began to grind her soft, plump
pussy against my hardening cock. She moaned and let her head fall back. Her
the streetlight outside hit her from behind, framing her into a perfect
silhouette. She continued to moan louder and louder, grinding harder and
harder against my cock. My hands explored her body. I reached down and
squeezed her ass, then I reached back up and fondled her tits. Her body was
perfect, a masterpiece.
Then she stopped. And I stopped. And the room became still and silent.
She looked down, eyes wide. My hard cock had sprung out from my
panties and she was staring right at it. She opened her mouth to speak, but
nothing came out. I did the same. Then, she looked up at me.
“I—I’m sorry,” I managed to say.
She didn’t say anything. She simply remained frozen.
“I can explain,” I said. “I—I mean, I don’t know what to say.” The reality
was, I couldn’t explain.
“You have a cock,” she said.
“I’m a man—I mean, I used to be a man.”
“You’re a T-girl,” she said, eyes still wide. Silence overtook the room.
“You—You’re actually Matt, aren’t you?”
I couldn’t respond. There was a fist-sized lump stuck in my throat.
“You—you’re a woman now?”
“Sort of,” was all I was able to say.
“You knew who I was, didn’t you?”
I shrugged my shoulders. “Yes.”
“Why didn’t you tell me?”
I wanted to throw up. I was ready to wake up from the nightmare. I was
ready for all of this to be over. I could move across the country, to a new city,
one I’d never been before, one where no one knew who I was, where no one
would ever find me.
“I couldn’t,” I said. “ I didn’t want you to think I was a freak.”
“A freak? Why would I think that?” Her look of horror turned into a look
of pity. I couldn’t decide which was worse. “Of course I don’t think you’re a
“No. I loved you, Matt.” She smiled. “I’m just glad to see that you’re
happy. You’re happy like this, right?”
I thought for a moment, feeling the burn sink into my heart. “I don’t
know. I loved you. I still love you. I was happy with you.”
“Then why do you look so sad?” she asked, looking down at me.
She was perfect, still framed angelically in that orange street light. It was
heartbreaking, how perfect she was, knowing that no matter who I eventually
found to be my soul mate would never be as perfect as April. “Because I
don’t have you anymore.”
“Yes you do,” she said. She leaned forward and kissed me. This time she
kissed softly, gently. The kiss was long, filling my heart with a warm glow.
She leaned back and bit her lip. “I’m a lesbian, Matt.”
My heart skipped a beat and I had to bite my lip to contain my smile.
“Call me Taylor,” I said.
We both laughed and then locked our lips together. The rest of the world
began to vanish and disappear around us. Nothing else mattered in that
moment. Nothing else would ever matter.
Lips still locked, she reached and grabbed my cock in her hand. Her hand
was warm and soft, fragile but confident. She began to stroke my dick. “I
wouldn’t be upset if you kept this,” she said softly into my ear.
I rolled on top of her. “Consider it kept,” I said, lining the tip of it up with
her tight, wet pussy.
“Fuck me, Taylor.”
I pushed my cock inside of her and she let out a loud, uncontrollable
moan. She loved it—I loved it. The walls of her tight pussy felt incredible
against my boner as I slid in deeper and deeper.
“Fuck me,” she said again.
I started to thrust into her, and I watched her breasts bounce up and down.
She reached up and grabbed my tits. Ripples of ecstasy pulsed through my
body as she fondled my nipples.
“Fuck me, Taylor. Fuck me harder!” she moaned. “I want your cum inside
I thrust into her as hard and fast as my small body was capable. I could
hear the sound of my pelvis slapping against her ass. Slap! Slap! Slap! Warm
juice began to ooze out from her pussy, around my cock. Her head was rolling
from side to side, eyes closed, lips parted. She was coming.
I couldn’t hold on any longer. I thrust inside of her one final time and
began to come. Her arms wrapped around me and she pulled her body in
tightly against mine. “I fucking love you,” she said. “I missed you so much.”
“I fucking love you, too.”
Dr. Anders is on the brink of a scientific breakthrough that will
revolutionize the modern world: Teleportation. His machine has worked with
small animals and inanimate objects, but it will be years before he gets the goahead
to test his system on humans. That is, unless he wants to test it on
himself. He knows it works, so how can he resist?
The night he decides to give his machine a try, something goes wrong and
Dr. Anders is surprised when he comes out the other end in the body of June,
his pretty, young assistant. Her DNA must have gotten into the system
He’s got a couple of weeks before June is back from vacation to adjust his
machine and get his body back.
But a female body comes with female urges. And you know what they say
—When in Rome.
I should have been focussed on the biggest accomplishment of my life,
humankind’s biggest accomplishment of the past one hundred years. But my
mind was elsewhere that day. Maybe it was the excitement of it all, the fact I
got less than an hour of sleep the night before. Or maybe it was my assistant,
June, who showed up to work that morning in a short skirt with nothing
underneath. I was on the ground, under my machine, making sure all of the
security bolts were tight when she walked past and I could see her perfect
little pussy, plump between her legs.
I thought it was rather strange that she was wearing heels that morning. I
just assumed she thought the press conference would be that afternoon (hard
to believe as I told her it wouldn’t be until the next week at the very soonest).
As the day went on, I swear the buttons of her top were coming undone. She
was wearing a red bra and she had a nice set of tits on her. I had never noticed
them before under the long white lab coat she always wore.
It was starting to become plainly obvious that she wanted to fuck me.
I thought that was strange, as she’d never shown any romantic interest in
me before—at least, not that I’d ever noticed. Maybe it was the fact I was
about to be the most famous scientist on the planet, the man who invented
teleportation. Or maybe I’d just never noticed.
My machines had been in the works for six years. And after hundreds of
thousands of hours of labour and countless failed trials, my machines finally
worked. A week before, I successfully teleported a mouse from one end of my
lab to the other. Since then, I’d successfully teleported dozens of mice, among
other things. Never a human, though.
It was a completely wireless system. The two machines could be
anywhere in the world, anywhere in the universe, and the teleportation would
take the same amount of time: 0.00026 seconds. 0.00026 seconds was the
amount of time the accelerator took to speed up the vibration of the particles
to the point they could be teleported. It was all based on the theory of
quantum entanglement and DNA analysis, but I won’t bore you with the
details. The point is, the things worked.
Before I could take my invention to the press, I still needed to test the
machines on humans. To avoid a mountain of legal ramifications and
insurance liability, I was going to be my own first subject. I had, after all,
designed the machines to be operable from both inside and outside, so the test
could be done solo. Within the year, I knew that my machines would
completely replace cars, planes, trains, and every other form of transportation,
save for the purely recreation forms of transportation. The world would be
cleaner and exponentially more efficient. I would, without doubt, be the next
recipient of the Nobel Prize in physics. Just saying.
So I couldn’t exactly blame June for wanting to fuck me so badly, so
obviously. Besides, after over half of a decade working together, it’s bound to
happen. Humans are, after all, animals, beings of lust and desire. She
probably couldn’t help herself.
I was filling out my daily diagnostics reports when June came into my
office, cleavage out, legs long, smooth, and perfect. She lingered in the
doorway, waiting for me to start the conversation. “What is it, June?” I asked.
“The lab mice are all fed and I cleaned all of their cages, Dr. Anders,” she
said. She continued to linger. Her perfectly smooth legs were surprisingly
“Thank you, June.” I returned to my notes, but she remained in the
“Is there anything I can do?” she asked. “Anything at all?” When I looked
back up, she was biting her lip slightly.
“I don’t think there is. All of the review reports are sorted into folders?” I
tried to look back to my notes but all I could see was the color of flesh in my
“All sorted and labelled, with copies in the fire-safe room.” The fire-safe
room was a room in the basement, completely encased in iron, like a bank
vault—indestructible. A nuclear bomb could have landed on the building and
everything in the fire-safe room would be totally fine.
“Well, I guess you can call it an early day and head home. Go and get
ready for that big vacation you’ve been talking about. Thanks for the work,
She lingered. “So when are you going to test the machine on a human?”
she asked. “I mean, do you need to find volunteers. I bet there’s a lot of red
tape and paperwork for that, huh?” June was completely oblivious to the fact I
was going to test the machine on myself that night, after she left for home. It
was better that she was oblivious, so she wouldn’t try to stop me. It was an
inherently dangerous venture. Throughout earlier trials, a number of brave
mice didn’t survive the blink from one machine to the other. It wasn’t until
very recently that the devices successfully moved organic matter from one to
the other without killing it, turning it inside out, or leaving half of it behind.
June and I had cleaned some very gnarly messes out from those machines
over the years.
As soon as June was gone, I would be setting up my cameras and
warming up the machines (they took about thirty minutes to warm up and
connect to the various servers and whatnot). If it worked—and I was about
99% certain it would work—I would do it again the next morning, in front of
every major news outlet in the country. Within twenty-four hours, I would be
the most renown scientist on the planet.
“Okay. Maybe I’ll just give the place one last do-over,” she said with a
smile, and then she turned away and started back towards the lab.
It was twenty minutes later when I went to check on things that I found
her inside of the departure-machine, on her back, legs spread wide, pussy out.
She’d been waiting for me. She smiled nervously but said nothing. Her
cheeks were red, adorable. She was putting a lot on the line: her career, her
reputation. Just for a chance to fuck. She must have really wanted it.
“June, this is highly unprofessional,” I said. I heard my voice crack and I
could feel a warmth rise up to my cheeks. It was hard to look away from her
perfect lips and her incredible, perky tits.
“Is it so bad to be unprofessional every once in a while?” It was hard to
deny that face—and that pussy, those plump, pink little lips. I couldn’t
remember the last time I’d had sex—years. Maybe not since before I started
this crazy project.
She said nothing else. I entered the departure-terminal and sunk down to
my knees. My first instinct was to feel her slit, to run my fingers up the length
of her snatch. It was warm and damp. She sighed softly as my fingertips
caressed her clit. My heart jumped. “I don’t know if this is such a great idea,
June,” I said. I liked June. She’d been nothing but great to me over the years
we’d been working together. I didn’t want to risk everything over a fuck, over
a moment of lust and desire.
She said nothing. Instead, she reached down, grabbed my hand, pushing it
firmly against her pussy. I slipped my middle finger inside of her and she
moaned. I could feel my cock hardening against my pants. She was beautiful.
I’d always known she was a good-looking girl, but I’d never realized she was
I crawled over top of her and our lips locked together. My hand stayed
down between her legs, under her skirt. I continued to finger her pussy. Her
tongue moved around my mouth expertly, sensually. I was completely
hypnotized. My body became relaxed. When was the last time I’d been this
relaxed? I wondered. For once in six years, I wasn’t thinking about my work,
about revolutionizing science, revolutionizing the world as we knew it. I was
only thinking about her, about her soft lips, her perky tits, and her wet slit.
Her hips rose off of the ground and I found myself slinking down her
body, passing her chest, her abdomen, her pelvis. My lips pressed between her
legs and I started to eat her out. It was as if someone else was in control of my
body, pulling on the strings of my marionette. Lust is a powerful overlord,
capable of reducing any man to his primal instincts. I was like a witness,
trapped inside of my body, yet somehow I was making every decision myself.
I slipped my tongue into her hole, eliciting another long, soft moan. Her
fingers nestled into my hair and she pulled me in tight. She was moist, wet,
ready. I grabbed her butt cheeks in both hands and squeezed. My God, she
was soft. So smooth, so perfect. How had I gone six years without touching
her, without throwing myself at her. How had I not made her mine?
Moments later, my pants were on the ground and I had her arms pinned at
her sides. The tip of my bare, erect cock pressed up against her warm, damp
hole. Her eyes lit up. She bit her lip. She wanted it so badly so how could I
deprive her? I pushed in and she gasped. It felt incredible. The warm walls of
her pussy hugging my member tightly, securely. I could feel it breathing, it’s
own entity, squeezing my cock one moment, releasing the next, then repeating
the process. I slid in deep. Her knees rose up to my sides. She squirmed but I
held her tight, in place.
Then we fucked. I pumped my manhood into her over and over, harder
and harder, faster and faster. Her head rocked from side to side, but her eyes
remained open, locked on mine. Our foreheads touched. Her pussy clenched
my cock tighter as she came closer to her climax. My cock bulged against her
tight walls as I came close to mine. Fuck, was she ever beautiful, her tits
bouncing up and down, nipples erect. She screamed out loud and I could feel
a rush of warmth against my cock. She was squirting.
I couldn’t hold it in any longer. I pulled out, letting her squirt spray
everywhere. Then, my cock began to unload on her belly, on her tits, on her
chin, blast after blast. Through heavy breaths I caught her smiling, biting her
lip, as if after six years she’d finally gotten exactly what she wanted. And I
have to say, it felt fucking incredible.
But after six years, I still needed to get what I wanted, and I was so close
to having it. As soon as she was dressed and on her way out the doors, I
booted up the system, flicked on the servers, and turned on the cameras. The
countdown had begun. I was going to be the first human to teleport from one
point in space to another.
My system was carefully designed to recognize human DNA. I spent
nearly a year training the computer to recognize and distinguish different
DNA patterns so to avoid any catastrophic failings. For example, if I was
teleporting a mouse, and the system was contaminated with a foreign DNA
strand (such as a human hair or even something as small as a human skin
cell), and the system was not be able to distinguish the two DNA samples,
then it would output some human/mouse monstrosity, which would almost
certainly die within seconds for more reasons than I feel I need to list. So with
my system, if it recognizes the DNA of a human, a mouse, a fly, and an
octopus, it will analyse each separately and output a human, a mouse, a fly,
and an octopus—separately. Simple, right?
Well, I made one big mistake. I trained my system to distinguish human
DNA from the DNA of other organisms, but I never trained my system to
distinguish human DNA from other human DNA—such a thing would be
nearly impossible without hundreds of millions of lines of coding. The
thought never even occurred to me.
So it wasn’t until after I stripped down, stepped into the machine, locked
the door, pressed the initiate-button, saw the flash of light, stumbled out the
other end, and then looked into the mirror to make sure I was still intact, that I
realized I’d made that very big mistake. Staring back at me in the mirror was
not me. I was staring at June, completely naked. I stood frozen for a moment,
and then I looked down and noticed the breasts, the pussy, the long, smooth
The teleportation was a success, sort of, aside from the fact my body was
completely transformed along the way. How could such a thing happen? What
had I done wrong? I didn’t have to think long before I figured it out.
June’s DNA was in the departure-terminal with me. The system analysed
both of our DNAs, recognized them as human, and outputted a single person.
Why had it chosen June’s physical DNA over mine? That, I couldn’t be so
sure of, though I had a theory: my system, like the human body during fetal
development, understood a human should have a single set of X and Y
chromosomes. Given the presence of multiple X chromosomes, it made the
simple decision to discard my physical DNA. Perhaps it was a totally random
decision, or perhaps it just found her DNA a fraction of a second before it
found mine—an order of operations—who knows.
As the initial shock wore off, I couldn’t help but smile. Despite the very
obvious blip, the machines worked. I was the first human to successfully
teleport from one point in space to another without physically moving. It was
a ground-breaking achievement for humanity. It would possibly take an entire
year (or more) of coding to fix the cross-contaminating issue, but I knew I
could fix it. I’d already spent six years on the machines. What was another
year? It was a small issue.
But the issue at hand was the obvious one. How would I get my body
back? I could go back to the departure-terminal with a sample of my own
DNA—my original DNA—and hope that it outputs me as me again, as Dr.
Anders and not as my assistant, June. I looked around the lab. Where would I
get a sample of my own DNA? The clothes I’d shed next to the departureterminal
likely had my skin cells on them, but I couldn’t put my clothes into
the terminal—not without risking being spliced with my clothes (it hadn’t
happened in any recent trials, but I wasn’t willing to take the risk). I could try
to extract my cells from my clothes and place them in the terminal with me,
but then the system would just be forced with the same decision it had before
—and seeing as computers are built for predictability, I could only imagine
the result would be the same. If I was going to get my body back, I needed to
address the issue in the system’s programming, which, at best, would take a
couple of weeks.
My phone buzzed. It was June. “At the airport now. See you in a few
weeks!” Thank God, the stars were aligning for me.
I couldn’t imagine the catastrophe of June coming into the lab and finding
herself staring face to face with herself. I had essentially become a perfect
clone of June. The philosophical implications were incredible—a whole other
topic for another time.
I looked into the mirror again at myself, at June. My heart skipped a beat.
Can you imagine, looking in the mirror every morning at that face? That
beauty? I grabbed my breasts in my hands and squeezed and a warm jolt
buzzed through my body. I reached down and touched my clit—my God, was
it sensitive! I nearly jumped into the air. So surreal, I thought. So incredible.
This was a scientific breakthrough of its own. Imagine the medical
implications! You could give a sick man a completely healthy body. Women
would no longer need plastic surgery. They could simply choose a model
from a catalogue and transform. Sexual reassignment would be
revolutionized. Men could become the most beautiful woman with nothing
but a skin cell or a hair. A woman could become any man she wanted.
Scientists would be marvelling over these machines for centuries.
But for now, I was tired, ready to pack it in for the night. There was a
couch in my office that pulled out—that would be my bed for the next little
while, until I solved my little body-swap conundrum. Before turning off the
lights and retiring to my office, I collected a DNA sample from my shed
clothes. I was going to need it once I finally located the glitch in my system,
if I was going to be turned back into Dr. Anders again.
The strangest thing happened after I lay down on my couch-bed.
I looked over at my wall where my degrees and accomplishments hung in
frames. Under my masters’ degree was a framed photo of me with one of my
old co-workers, back when I worked at a major tech firm. His name was Riley
Sanderson, a slightly younger man than I, just a few years younger than me.
Riley and I were the head researchers in a quantum processor research
project. We created a computer processor that could run at five-thousand
times the speed of an analogue processor, and it could be made to be less than
half the size. Those same processors were inside of my teleportation machines
—a vital component when scanning millions of cells at once. Since I left the
firm, Riley had worked his way up to CEO and had made himself a very rich
man. We still kept in touch. He was the key investor in the teleportation
But when I looked up at his picture, I felt a warm glow flow through my
body. I found myself mesmerized by his blue eyes, his broad shoulders, his
scruffy hair. He was handsome, beautiful even. It was hard to look away. I
tried to shake the alien urges I was feeling, but they were only growing
stronger. These urges were different than anything I’d ever experienced as a
man, as Dr. Anders. These urges were stronger, empowering my whole body.
I had no idea how to fight them, how to control them.
My fingers found their way to my bare breasts. They squeezed and that
warm glow grew stronger. I let my head fall back and I closed my eyes. My
mind was spinning in this new euphoria, this foreign sensation. It was overstimulating,
like a new drug rushing through my veins. I could practically feel
Riley over top of me, naked, his hard, veiny erection towering over my
abdomen. I could practically feel his big hands grasping my thighs, spreading
my legs wide. The tip of his cock presses up against my pussy and it’s huge
and intimidating but still I want it so badly. I’m practically pushing myself
down onto it. I can feel a dribble of moisture making its way out from my slit,
down my butthole. I’m so wet, so ready for him.
He’s strong—incredibly strong, or maybe I’m just weak. He pushes
himself inside of me and my body surrenders. I’m his to do as he pleases. I
can practically feel him sliding in and out of me, the thick veins and ridges of
his cock massaging my clit, massaging the walls of my pussy. It isn’t long
before I’m a complete mess, practically a limp doll on the floor that he’s
fucking. It feels so good, so fucking good. My wrists hurt from his grip, my
back hurts from being slammed against the ground, but I could care less. I’m
swirling in a state of uncontrolled euphoria as his long, slick member slides in
and out of my body.
Then I feel it, him coming inside of me. It’s enough to make me scream in
uncondensed pleasure. I squirm, my head rolls from side to side. And when I
opened my eyes, I realized I’d had my hand between my legs, fingers deep in
my slit. My other hand was on my breast, squeezing, fondling my nipple.
If that was what a female orgasm felt like, I wasn’t sure I wanted to go
back to being a man. Hell, that was just an orgasm with a couple of fingers
and a little bit of imagination. What about an orgasm with a man? A real,
tangible man, not just an imaginary vision, a sleep-deprived hallucination.
I shook my head. I needed to keep my focus straight, on task. I couldn’t
lose sight of my objective, to complete my machines, to release my invention
to the world, to revolutionize science. The sexual experimentation could wait.
Hell, with my invention, people could change from male to female and then
back again on a complete whim, and still be home in time for dinner. All you
needed was a tiny DNA sample and you could experience life as anyone you
wanted to—at least down to a physical level. You couldn’t just become Brad
Pitt and be acting on a multi-million dollar set tomorrow, of course.
There would have to be limitations set into the machines, regulations to
stop imposters and imposers. There would have to be permissions and
releases and a whole myriad of waivers and paperwork. Without regulation,
any pervert could easily change into his target lady’s husband and the lady
would be none the wiser. It was a terrifying thought, to say the least.
The next morning I was awoken by a loud knocking at the lab door. It
took me a moment to piece together the previous night, to remember why
there was a beautiful pair of tits on my chest. But as soon as everything came
together, I sprung to my feet, heart racing. Whoever was at the door was no
stranger. I knew everyone with a key into the building. If it was June, she had
a key into the lab. It would be impossible to hide.
Butt-naked, I ran with light feet to the door and gazed out the peep-hole.
Standing on the other side of the door was Riley Sanderson. My heart sank
into my gut. What was he doing here? I hadn’t seen Riley in over a year, since
he wrote his last investment cheque. Riley was a major investor in my
teleportation machines. It was through him that I got all of my hardware, my
processors, and so on. He had more money than he knew what to do with, and
he wanted to be a part of history as much as any scientist.
I ran to the backroom and grabbed one of June’s lab coats. I didn’t have
any other clothes to put on. My own clothes—the clothes of Dr. Anders—
were far too big for my small, female body. Hopefully, Riley wouldn’t
question why my legs were bare under my lab coat. Hopefully he wouldn’t
even notice—though that would be difficult seeing as June had impeccable
legs that no man could go without noticing. He knocked again.
“I’m coming, hold on,” I called out. I was surprised by the sound of my
own voice, of June’s voice coming out from my body. I hesitated and then
said a few lines to myself. “Whoa. I sound like her. I sound exactly like her.”
Until that moment, I hadn’t taken my voice for a test run. I hadn’t even
I opened the door and Riley was standing there with a confused look on
his face. “June?” he said.
“Hi Mr. Sanderson.” My voice was rattled, my hands were shaking. I tried
to collect myself, but couldn’t quite manage it. I had this crippling fear that he
could see right through me, see that I was actually Dr. Anders inside of June’s
body. It was a preposterous thought, of course—no sane human would assume
such a thing. But still, that fear lingered.
“I thought you said you were on your way to the airport,” he said and then
he stared at me in silence, with that confused look still on his face.
“When you called earlier, to let me know the machines were done, you
said you were headed out on a vacation.” He stepped past me into the lab and
started to remove his gloves and coat. I wanted to stop him, but as June, I
couldn’t. Even as Dr. Anders, I wouldn’t have been able to stop him. He was
the money behind the project. The money gets to do whatever it wants. That’s
the way it goes. Had I tried to stop him, he would have made sure June was
out of a job by the end of the day.
“Oh right, I realized I had to get a few things done here before I left,” I
said. I knew it sounded stupid but I had nothing else. I had no idea what June
had already told Riley, no idea what kind of knowledge base I was working
with. “I rescheduled for tomorrow,” I said.
“Last second re-schedule. Must be very important. In Anders here?” He
tossed his coat onto a hook and then looked around.
“Not yet. I think he’ll be in later this afternoon. He was here late last
“Yeah, you told me on the phone. But I didn’t think Anders slept.” He
laughed. “I was hoping to see these machines in action. You know, before the
big press release.”
“I don’t think there is any planned press release. And it’s not quite ready
to be shown yet.” I caught myself talking as Dr. Anders and not as June.
He looked at me with that increasingly familiar look of confusion. “Wait.
You said on the phone it was done and it worked.”
I could feel my cheeks turning crimson. “Well, yeah it works. Just not
with humans—I mean, it’s not tested with humans. We’ve had successful tests
on mice and dogs.”
“I’d like to see that.” He wandered around the lab, inspecting all of the
machinery. He nodded at some things, as if he agreed with my methods, and
then he questioned other things, as if he would have done them differently. Of
course, knowing Riley, he was sure he could have done everything slightly
better than I had. If I wasn’t careful, he would start tinkering with things,
setting me back days, weeks, even months.
“Please don’t touch that,” I said as he reached for the data-intake housing
unit, where the machines stored and transmitted DNA information. It was a
sensitive unit—the exact unit I needed to work on if I was going to get my
real, male body back. All he had to do was sever a single of the thousand
wires looping out of the system and I had another month of work on my plate.
He looked at me with surprise and then he laughed.
“I’d really like to see these things in operation. Maybe you can show
me?” He looked me up and down, spending an extra moment down at my
legs. I realized in that moment that I was barefoot. He didn’t question it, but
I’m sure it took him by surprise. It was highly unusual, after all, to be
barefoot in a laboratory—especially one where contamination could be a
“Um,” I said. If I said no, I knew he would probably end up waiting
around for Dr. Anders to show up, poking at things, tinkering with control
boards. If I just demonstrated the machine using a lab mouse, I had a feeling
he would be content and on his merry way. Then I could get to work, locating
the glitch in my DNA storage and transmission system. “Okay, sure. I’ll grab
“No, no. Let me pick the mouse. So I know it’s not some kind of rouse,”
he said, walking over to the row of cages. He picked a black mouse with a
distinct white spot on its side. “This one. Where do I put it?” He looked
around the room. Thank God, I thought, something like this never happened
when June was here alone. June would have let Riley walk all over the place,
sticking mice in whatever the hell he wanted.
“Give it to me,” I said, taking the mouse from him and walking over to the
departure-terminal. I explained the system to him in dumbed-down terms. He
could have understood the highly-technical terms, but I didn’t want to give
away my guise. I had to show him just enough to make him trust me, but not
enough that he suspected anything. If a lab assistant started to explain
quantum entanglement, Riley would have known something was up—though
I’m sure he wouldn’t have believed I was actually stuck in a clone of June’s
body. I could have straight up told him I was trapped in a clone of June’s body
and he probably wouldn’t have believed it.
I booted up the systems and he wandered around while things warmed up.
He kept an eye on me, making sure I wasn’t slipping an identical mouse into
the output terminal. Even when I was sitting stationary, he kept his eye on me.
Maybe he wasn’t trying to catch me in the act. Maybe he was just admiring
my body—June’s body. Maybe he could tell I didn’t have a shirt—or even a
bra or panties—on underneath my lab coat. Maybe he could tell that all there
was between him and my pussy was that white lab coat. Or maybe he could
tell, subconsciously, that I’d fantasized about him, just the night before. That
I’d imagined him holding me down and fucking me senseless. Maybe he
wanted to fuck me senseless.
We were alone, after all, in that lab. There was no one else in the building,
as far as I knew and as far as he knew. The other labs were generally empty
on weekends. He could do whatever he wanted to me and no one would have
heard a thing. He could have pounded my pussy out in the building’s lobby
area, and I could have had an orgasm at the top of my lungs and no one would
have any clue.
The machine beeped, letting me know it was ready for the demonstration.
“It’s ready, Mr. Sanderson.” He walked up behind me, close enough that I
could feel his presence, feel his much larger body, his broad shoulders
towering over me. “I’ve placed the mouse in the terminal. Now I’ll close the
hatch.” I closed it.
“What does this button do?” he asked, reaching past me and pointing at a
button on the system dashboard. His chest was pressed against my back and
his chin was almost touching my cheekbone.
“That’s to test the object’s density. It’s obsolete with the new firmware,
but I—I mean, Dr. Anders hasn’t updated the dashboard. A few of these
buttons are obsolete.”
“You smell nice, June. I thought scientists weren’t supposed to wear
perfume. Can’t that mess with the experiments?”
“I’m not wearing any perfume,” I said. I could feel his presence becoming
I hesitated, then continued with the demonstration. I could feel a warm
surge coming on, a similar euphoria to what I felt the night before, before my
new instincts or my new hormones or my new whatever it was took over. But
I had to keep myself in check. I had to be professional for June’s sake, for my
own sake. I couldn’t have my assistant throwing herself at my biggest
investor. Even if it was actually me and not my assistant, Riley Sanderson
didn’t know that. “It’s very simple. Once the specimen is enclosed in the unit,
you press this button and that’s it.” I motioned towards a large, red button.
“Can I press the button?” he asked, reaching further past me for the
button, pressing his body against mine.
I swear I could feel the bulge of his cock against my butt. It was hard, or
maybe that was my imagination. Maybe that was my swirling emotions
fooling me. “Sure,” I said, and he slowly pressed the button.
After a flash, the mouse disappeared. I pulled myself away from his
presence and started towards the output terminal. He followed. “And just like
that, the mouse has been teleported?” he asked.
“Just like that.” I had the urge to explain it to him, but I held back. The
explanation could wait until I was back in my own body.
I picked the mouse up and showed it to him. He shook his head and
smiled, but didn’t seem too impressed. At least, he didn’t seem to be too
interested in the mouse. He was looking at me, smiling, with that look in his
eye that suggested there was more on his mind. “It’s a shame your vacation
plans had to change,” he said.
“Hey, it happens. If there’s nothing else that you need—”
“—You know, you’re really very beautiful, June. I can see why Anders
likes to keep you around here. I mean, don’t get me wrong, I’m sure you’re
incredible useful to him.”
I blushed. I may have held onto my own mind, my own consciousness,
but my brain was almost certainly a DNA-exact clone of June’s brain. All of
her urges, her hormones, her instincts—everything controlled by the brain—I
was now feeling. And it was frighteningly overwhelming. I couldn’t
understand how women could control the overwhelming attraction that was
now pulling me towards Riley. He was so handsome, so irresistible. There
was an aura about him—a dominating aura, a powerful aura. He was a
powerful man, and there was something incredibly irresistible about that,
something I’d never even noticed as a man, as Dr. Anders.
He reached out and placed his hand on my arm. Then, he laughed. “You
wouldn’t be naked under that lab coat, would you?”
My face was now a dark red. “Naked?” I said, looking down, trying to see
what evidence he had. My nipples were hard, pushing against the thin white
fabric of the lab coat. That, with my bare legs and bare feet, made it
somewhat obvious. After a moment of trying to string together a sentence out
of stuttered fragments, I laughed. “It’s a long story. I—”
Before I could finish my inevitably rambling sentence, he stepped forward
and kissed me. A swirl of conflicted emotions rendered me frozen. I may have
been in a woman’s body, but I was a man—a straight man. Straight men don’t
kiss other men. But at the same time, I was in a woman’s body, being driven
by a woman’s impulses. And what made those impulses any different than the
impulses I felt in my own body? The lines were faded, black and white turned
to grey and I was lost somewhere in the middle.
The female impulses won the battle. I melted into him, letting him wrap
his arms around me. He was strong. I could have let my body go limp and I
would have stayed in the same exact place. He wouldn’t have even noticed a
thing. He let my tongue explore his mouth, and then his tongue explored
mine. The next five minutes all seemed to buzz by in a flash: his hands
exploring my body, my lab coat falling to the floor, me falling to my knees,
his cock springing out as I pulled his pants down. I hesitated with his cock in
my hand. I’d never had a cock in my hand—not that wasn’t my own, anyway.
His was big, bigger than mine, and way thicker. Or maybe it just seemed that
way because my feminine hands were smaller, more delicate.
“Go ahead, baby,” he said, slipping his hand behind my head, pulling it
towards his throbbing member.
Gently, I parted my lips and let the cock slip in. It was warm. I could feel
his veins pumping blood into his cock, making it harder, somehow longer. I
gagged at first before getting my rhythm. “Just like that,” he said. Honestly,
he was doing most of the work, my head in his hand. He pulled me in and
pushed me off, eventually getting both of his hands into the mix, one on each
side of my head.
He slowly started to thrust himself forward, sinking his cock further
towards my throat. “Just like that,” he said again. His head fell back and he let
out a long, deep sigh. I was doing something right. He was apparently in a
state of bliss. I worked his shaft with my hand as I sucked him off.
“Finger your pussy, baby,” he said. I looked up and he was looking down
at me with a expectant expression. His gaze was commanding, hard to deny. I
didn’t deny it. I reached down and started to stroke my pussy with the tips of
my fingers. He watched while I continued to suck him off. “Stick them in,” he
commanded, so I did. Two of my fingers slipped into my body. “Rub your clit
with the other hand.”
Riley Sanderson had gotten much bossier since I’d last spoken with him,
or maybe this was his way with women. Likely the latter. As a man, I would
have punched him right in the face, had he commanded me like that. But as a
woman, it was different. There was something so tantalizing about being told
what to do and how to do it. I wanted to be his. I wanted to please him.
Pleasing him got me off, got my blood flowing, got that warm energy rushing
through my body.
I started to moan, gagged by his cock, which was still sinking deeper and
deeper into my throat. “Don’t stop,” he said, and I didn’t. I was jerking him
off quickly, sucking ferociously. His legs quivered. I could feel his member
bloating in my mouth. He was going to come.
“C’mon, baby,” I said, surrendering to every impulse inside of me. “Come
on my face.” I was completely out of control of myself. My hormones were in
the driver’s seat. That warm energy all started to rush down to my pussy. The
sensation was powerful, consuming. I came, pulling my head back and
screaming out loud.
That was enough for him, too. His cock began to blast my face with hot,
sticky cum. He held my head in place, making sure I didn’t miss a single shot,
and I didn’t. I was covered, soaked, dripping. I could taste his sweet cum on
As soon as he caught his breath he said, “I should be going.” He had a
smile on his face that didn’t disappear as he pulled up his pants and headed
for the door. “We should do that again sometime. Maybe when you’re back
from your vacation.”
I smiled. “Maybe.”
Then he was gone. I cleaned up in the bathroom and then came out again.
I noticed my DNA sample sitting on a desk. I wondered if I wanted to go back
to my old self, my Dr. Anders self. Or maybe I liked being a woman. I smiled
—I could get used to those intense orgasms.
It was ten tediously long days before I got anywhere in my coding. I was
trying to find a single line of code within millions of lines. But it wasn’t as
simple as a quick search of the code, I had to go through it all, line by line,
because I wasn’t looking for a keyword, I was looking for a blip in the order
of operations. My theory was that the order of operations was what had
caused the error in the system, to choose June’s DNA over mine when making
the switch. Long story short, I found the line of code that I thought was
responsible. My program was set to make a series of millisecond-fast
decisions in an order, rather than every decision at once after analysing all of
the data. A single character was all I needed to delete from my code to
address the issue. Once the change was made, I had to install the update into
my machines and reboot everything. It was a procedure which took about
twelve hours of processing. I went to sleep and woke up with less than an
hour left on the reboot.
While I was waiting, a noise caught my attention. It was a faint jingle and
then a metallic cranking. I looked to the door. It was someone unlocking the
door. Shit. I jumped to my feet in a panic. The door started to open and I
started towards my office. But I was too late. “Hello?” the familiar female
voice said. I was in my office but I’d already been caught. June saw a woman
sprinting across the room. Maybe she hadn’t recognized that woman to be a
spitting image of herself, but there was no way I could get out of the situation
without her seeing me. There was also no way of lying my way out.
So with a large pit deep in my stomach, I stepped out from the office and
her expression dropped. “What the hell? Who are you? Why—Why do you
look like me?” She took a step back towards the door.
“I can explain everything. Please, just listen.” And so I explained what
had happened and how I’d been working towards fixing the issue. It took a
few minutes for the explanation to permeate her shock, but ultimately the
explanation seemed to give her some peace of mind. “So you retained your
own consciousness but your body changed completely? That’s so…
fascinating.” She walked up to me and then felt my skin, making sure I was
real and not some figment of her imagination. “Incredible.” I’d forgotten how
delicate her touch was. Strange, as we technically had the same touch. Yet,
somehow, coming from her, it was different. I couldn’t help but think there
was some metaphysical difference between our bodies. Sure, our physical
bodies were identical—clones. But we were different people still, with
different energies. She smiled.
“The system is almost back online. Everything will be back to normal
soon,” I said.
She stared at me in a way she’d never stared at me before—and not just in
fascination. I couldn’t put my finger on that look, but there was something
heavy on her mind.
Once the machines were back online, I went straight for the terminal. I
hesitated at the door. A part of me wanted to turn around, to abandon going
back to my male self. I’d enjoyed my time as a woman, experiencing life as a
woman. There was so much more I hadn’t been able to see—life outside of
the laboratory walls. But I couldn’t remain a woman, not in June’s body.
Perhaps one day, when all was said and done, and my technology was
mainstream—maybe then I could give it a shot.
I stepped into the machine with the DNA sample I took a few weeks
earlier from my clothes. I left half of the sample in another vial, in case the
experiment failed and I needed a piece of my old self for future attempts.
“Wish me luck,” I said.
“Good luck,” the real June said back to me.
I closed the hatch and pressed the button. Everything flashed and then the
door opened. I was on the other side of the room. The teleportation was a
success. But was the body-swap? I walked out of the terminal. June was
looking at me but I couldn’t gauge her expression. I walked to the mirror. I
was still a woman. I was still June. My fix didn’t work. The system still
prioritized June’s DNA pattern over mine. “Damn,” I said.
“We’ll figure it out,” June said, walking up behind me.
“It will take years to figure this out. Like finding a grain of sand in a
forest.” I sighed. “If we could just narrow down the issue… Is it prioritizing
female DNA? Your DNA? Or is it just acting randomly? Did I flip tails twice
in a row?” I looked to the machine and wondered. Was it maybe something in
my DNA? A recessive flaw? Something in my own DNA telling the machine
to prioritize June’s DNA?
“We’ll figure it out,” June said. She planted a kiss on my cheek.
I returned to my office and sat down. I stared at the wall and thought,
running through various scenarios and possible remedies in my mind. I was in
a serious bind. In an experiment such as this, you would never run the same
test over and over on the same mouse. You would run the test on a variety of
mice. The varying results would help in narrowing down the possible
solutions. I didn’t have multiple human subjects to test my theories on. I only
had myself. And every time I went into the machine, I would get the same
result, over and over, and I would be no closer to a solution.
There was a flash of light in the laboratory. I leapt up from my seat and
ran over. The machines were whirling from recent use. The output-terminal
door swung open. Then, a man stepped out. I had to rub my eyes and take a
closer look, in utter disbelief of what I was seeing. It was me—Dr. Anders—
stepping out of the unit. I opened my mouth to speak but I was speechless.
He walked over to the mirror and looked at himself. “Whoa,” he said. I
knew immediately it was June, though I couldn’t tell you how I knew it.
“June? What did you do?”
“I went into the terminal with your sample,” she (who was now a he) said.
“Why?” I couldn’t believe what I was seeing. There is something
incredibly surreal about staring at yourself through someone else’s eyes. It
was like staring at a stranger, but recognizing them entirely. I wasn’t staring at
myself. I was staring at a surprisingly handsome man (I’d never considered
myself to be a handsome man). He was strangely attractive, which I didn’t
know how to feel about. I felt almost guilty about it, as if I was having
incestual feelings for what was essentially my own self. But it wasn’t my own
self, it was June.
“To see what would happen. To narrow down the possibilities.” She
smiled. “Besides, I’ve always wanted to see what it was like to be you.” A
part of me was angry with June, but at the same time I was ecstatic. She’d
answered so many of my questions—questions which would have taken
months, if not years, to answer with my limited resources. Had she answered
every question? No. But we were closer. She did it for science.
Or maybe she did it for me.
She looked me up and down and laughed. “Hey, I’m pretty hot.”
“I’m not too bad, myself,” I said.
She looked at my chest and her face lit up. “Want to come to my office for
a moment?” she said, motioning towards my office. “I have a few personal
experiments I need to run.”
“Of course, Doctor,” I said, following her. The decision was mutual and
unspoken. There was no rush to get to the bottom of the DNA-analysis issue.
No rush at all.
John loves excitement, any way he can get it, and crime is an easy way to
get it. He was once involved in drug trafficking, even though he’s never done
a drug in his life. Drug trafficking led to gun trafficking, which led to human
trafficking, and now his illegal thrill obsession has brought him all the way to
So naturally, when John stumbles upon a secret underground network, a
niche sex-trade filled with gorgeous transgender beauties, he can’t help
himself. He never knew he had a thing for trannies, but no sane man could
turn these stunning ladyboys down. Not to mention, the business potential is
The only question is, will John get carried away with his new exotic
In too deep was the understatement of the year. I was in so goddamned
deep I couldn’t figure out which direction the surface was. I’d uncovered a
whole world I never knew existed, an elaborate underground network of
crime and dealings you wouldn’t believe. It all started out as a simple drug
operation, running cocaine into Thailand. Next I found myself moving
firearms, supplying shady characters with guns that I highly doubt would be
used to hunt deer. One thing led to another, and I ended up in the sex trade.
I was a higher-up, coordinating business between Thailand and Laos. It
was a welcomed change from the hard drugs and the guns. Hard drugs and
guns can fuck people up, prostitutes are a different story. They’re just there so
you can have a good time. I guess you could say I was like the pimp to the
pimps. They would all go and collect their bit, and then I would go to them
and collect mine. Actually, more often than not, they would come to me. It
was an easy gig.
Strange to think that I worked in a New York City bank just a few years
before, with a clean white house in the suburbs. I had all the money I could
ever want. But that got boring fast. There’s nothing exciting about having
money. Chasing money, now that’s a different story entirely. Don’t get me
wrong, if anyone loves money, I love money. I could bathe in the stuff, sleep
in the stuff, dress myself in the stuff—if such a thing was socially acceptable.
But the first time I ever felt alive was the day I got an insider tip about a stock
that was going to blow up. I’d never felt anything like it, putting my entire life
savings into a single stock, watching it closely as it started to take off, heart
accelerating every time a siren zipped past my little office. I knew I needed
more—more of that excitement, that chase, that wonderful, wonderful chase.
I’d never considered myself a criminal, though I was starting to think
otherwise. I never wanted to hurt anyone. Sometimes chasing the money
clouded my judgement somewhat, but I tried to keep my sanity. Prostitution
was a good place for me. It was a safe trade down in Thailand. Everyone was
having a good time, no one was getting hurt. And it was only kind of illegal,
so I knew I probably wouldn’t end up in a Thai prison. Even the ladies
seemed like they were enjoying themselves. None of the girls I ever talked to
said that they were forced into it. Most of them were just happy to be feeding
their families. Good on them, I say.
But the inevitable finally happened, and the boredom began to seep in. We
had our system worked out so well, so refined. We found loopholes in the law
that made it impossible for police to touch us. We’d narrowed down all of the
areas in the city where we could maximize profits. And we’d fallen into a
perfect schedule, so perfect you could set your watch to it. Every Friday I
would make my collections, Monday I would deliver to my bosses, and the
girls took Tuesdays and Wednesdays off. I bought a nice little mansion on a
hill, just outside of Bangkok. Things started to seem awfully similar to my life
in New York City. Just a bit more grand and I had a bit more downtime. My
bank account was growing far faster than I could empty it and the excitement
was fading fast.
Okay, so before I go on to tell you how I fell so far down the rabbit hole,
how I found myself in—quite possibly—the most serious danger I’d ever
been in, I need to make a confession, and you might not agree with my morals
and of course I understand that. I suppose you could say that I have an
addiction, though it’s not a chemical addiction. It’s a sex addiction. More
accurately, it’s a prostitute addiction, and it ties into what I was telling you
I crave excitement. And there’s nothing more exciting than breaking the
law. Sleeping with a prostitute is just the first step. Sleeping with a prostitute
in a public place, that’s two charges. Now we’re talking. I’m not saying I’m
fucking these girls in the middle of some little kid’s park—give me some
credit, here. But sometimes I’ll take them into the bathroom, door unlocked,
outside of the stall, and I’ll bend them over the sink and fuck them, taking my
chances. Anyone could walk through that door—or no one. Maybe I am
addicted to gambling after all.
Now usually I slept with my own prostitutes, girls who worked with the
ring I managed, who knew me, who I knew. But every now and then I’d see a
girl standing on the street corner that I didn’t recognize. And occasionally, I
couldn’t resist. I’m only human, after all. One afternoon I saw the most
beautiful, jaw-dropping specimen you’ve ever seen. She had these irresistibly
long legs, long black hair, down to her butt, and she was wearing a black
number that made my cock desperately attempt to break free from my pants.
She was a bombshell, drop-dead gorgeous. How had I never seen her before?
Was she new? She paced the street corner with a confidence I couldn’t
imagine. Across the street, men were eyeing her. No wonder I hadn’t seen her
before—she probably didn’t last more than five seconds on that corner before
being picked up, and if I were to pick her up, I don’t know that I would let her
go again. She had that look you just had to have, had to own.
I thought of approaching her, recruiting her to my own circle. I knew she
would go for it. We paid our girls more than anyone else in the city. Unsigned
prostitutes practically begged to be part of our ring, but we only took the best.
This girl was the best. But before I recruited her, I felt as though I needed to
take her for a test drive, make sure the performance matched the look. I mean,
you wouldn’t buy a car without taking it for a test drive first, right?
She was shy. When I introduced myself, she didn’t respond. She just
nodded her head and smiled. It wasn’t until I asked her for her price that she
spoke. Her voice was soft, quiet, harmless, but it packed a punch, clenched at
your loins, ate away at your soul like the song of a siren out at sea. “Fifty
dollars, American,” she said. Most girls upped their rates for white guys like
me. Plus, my New Yorker accent was unmistakable.
Can you imagine? Fifty dollars for a night with an angel, a total vixen.
The girl had no idea what she was worth. There were men back in America
who would pay thousands for a girl like her. “What’s you name?” I asked.
“Phan,” she said and then she looked around and stepped closer to me. I
could smell her perfume. It was beyond tantalizing, making my legs weak. I
wanted to grab her, flip her around, and fuck her right there, against that brick
wall. What was a public indecency charge anyway? It’s not like I was
planning on applying for a job at McDonalds any time soon. But I kept my
composure. “I come with extra,” she whispered into my ear.
I didn’t know what that meant but I didn’t care. “Deal,” I said, and I
showed her towards my car. My heart was racing. I couldn’t remember the
last time I’d been so excited. I could hardly wait to throw her down in the
backseat, rip that little number off of her body, and watch her tits bounce up
and down while I pumped my cock in and out of her pussy. My hands were
shaking when I opened the door for her. “You want to do it here?” she asked. I
was parked on the edge of the alley, just thirty feet from the main drag. My
windows were tinted, it was a fairly safe ordeal. Someone would have to walk
up pretty close to the car to realize people were fucking inside of it. But what
was the fun without the gamble, right?
She fell down onto her back and smiled. She knew how to smile, how to
melt a man, reduce him to nothing but his primal instincts. But she looked
nervous. Her cheeks were red and she bit her lip. I considered asking what
was wrong, but I didn’t pay her to hold a therapy session. I paid her to fuck,
so that’s what I intended to do: fuck. I kissed her neck, getting another strong
whiff of her perfume. My cock became as stiff as a post. I pulled the straps
down from her shoulders, working my way down to her breasts. They were
soft, supple, her nipples were hard. I explored them with my hands, my lips,
my tongue. She seemed stiff, still nervous. She must have been new to the
game. Not for long, though. With her looks and the business I could get her,
she would be one of the richest girls in Thailand by the end of the month.
I pulled her little black number down further, down past her flat abdomen,
past her shaved pubic area. Then I froze at the sight of it. Between her legs
was a flaccid cock, curled down towards her butthole. Considering how long
it was, it was impressive she kept it tucked so discreetly. She obviously saw
the shock on my face because she quickly said, “I told you, you get extra.”
Now I knew what extra meant.
I’d heard of Thai ladyboys, but I’d never seen one before. Or maybe I had
and I just hadn’t realized. If this ladyboy could look this convincing, what
was stopping the other thousand girls out on the street? “You—You’re a
man?” I said.
She gasped and closed her impressively feminine legs. “Excuse me? I’m
not a man.” I’d offended her. “Just fuck me, white boy. I promise it will be
worth every dollar.”
I have to say, I was conflicted. I’m not gay. I’m not interested in men or
their cocks. But she was right, she wasn’t a man. At least, no sane human
would look at her and call her a man. She was absolutely gorgeous. Her tits
were more perfect that any prostitute in my ring, her ass was to die for. The
only issue was… the cock between her legs.
“You fuck my asshole. It feels better than a pussy. I promise,” she said.
She grabbed her ankles and hoisted up her legs, presenting her asshole. I was
still frozen, undecided, not sure whether I should have been offended or if I
should be sticking my still-rock-solid cock into her asshole.
A familiar buzz filled my body. It was excitement, the excitement I’d
always craved so badly. Anyone could have walked up to that window and
looked in, seen me there railing a ladyboy in the asshole.
No risk, no reward.
My heart rate soared. I couldn’t believe it, I was actually going to do it. I
reached forward and ran my fingers down her leg. God, was her skin soft,
smooth, just like a woman’s. My fingers found themselves down at her
asshole and she smiled. I couldn’t resist. I slipped the tip of my index finger
in and her butthole clenched it like she wanted it. She bit her lip again. She
did want it. I could have told her I wasn’t paying her the fifty bucks and she
would probably still want my cock in her ass.
So I pulled down my pants and shimmied forward. “Fuck my asshole,
white boy,” she said. She took charge, reaching down and grabbing my cock
firmly in her grip, leading it towards her asshole. I watched in a state of halfexcitement,
half-amazement. She was a tiny ladyboy, probably no more than
ninety pounds. I weighed twice her weight. My cock was practically the size
of her forearm. And then there was her tiny little asshole. There was no way
she was going to take it so easily, so voluntarily. But there she was, cramming
my cock inside of her, not even flinching as I sunk in deeper. She let her head
fall back and she sighed. “Feels so good,” she said, and she was right. It felt
incredible, her asshole breathing, clenching my cock, sucking it deeper and
deeper. Hell, she could probably feel the big cock down near her throat.
I started to thrust, gently at first, still not sure her tiny stature could take it.
But she seemed to be in a state of total euphoria, complete ecstasy. She loved
it, every inch of it. She was pushing herself down on it hard, fast, practically
doing all of the work. I reached down and grabbed her tits, my body finally
I could feel the presence of the tinted windows all around us. They
weren’t blacked out, like a limousine. Just tinted, just enough that you
couldn’t see in from afar, not nearly enough that you couldn’t see in from up
close. Anyone could have walked up and seen me thrusting my cock into the
ladyboy, her own cock slapping repeatedly against her abdomen.
She was getting hard, her cock growing longer and thicker. I was
impressed with just how long it got. Then I started to wonder—if someone
did look in the window, they would have seen my back, clearly fucking a
whore. But my body would have blocked the lady out. You wouldn’t have
been able to see her hardening dick on her stomach. So I pulled out. “Get up,”
She looked at me with confusion in her eyes.
“Get up,” I said again, so she did. I took her spot, with my back along the
backseat. “Okay, get on,” I said. She went to straddle me with her ball sack on
my abdomen. “No, the other way,” I said, and she turned around, back facing
me. Once again, she did the work, grabbing my cock in her fragile grasp and
leading it into her butthole. Once I was in, I reached around and pulled her
down, her back on my chest. Now if anyone looked in, they would have seen
it all—her beautiful face, her perfect tits, and her big, hard cock. Now the
stakes were really high. Now this was a real gamble.
I kissed her neck and I continued to fuck her asshole. “Oh God,” she said
before breaking off into some Thai that I couldn’t understand. I still couldn’t
get over how feminine her voice was, never mind her body. “Oh fuck, fuck
my asshole, fuck my asshole,” she said.
I had the sudden urge to reach around and grab her cock. I can’t explain
the urge. I’d never in my life had any similar urges. I’d actually hoped I
would go my whole life without touching a cock that wasn’t mine. But
something compelled me to grab onto hers. Maybe it was because it wasn’t a
man’s cock, but a woman’s. Or maybe I was just discovering I had a thing for
ladyboys. I started to pump her dick. “Oh yeah, you dirty fucking white boy,”
she said. “Beat my dick.” Then she said some more things in Thai that I
Her dick felt nice, warm, perfectly conforming to my grip. I could feel it
pulsing, getting somehow harder, bigger.
She was in the middle of some sort of hybrid orgasm, moaning
uncontrollably, head rolling from side to side, eyes closed, dick throbbing.
With every thrust, my entire cock went deep inside of her asshole. I couldn’t
believe she could take the whole thing so effortlessly. Watching her squirm as
she tried to control the unrelenting pleasure surging through her body, I
couldn’t help but wonder what that felt like. Not just getting beat off with a
cock deep in your ass, but the excitement of it, of being with a stranger, of
being with a man, of being in the body of the other gender on top of it all. Can
you imagine? This was sex on a whole different level, a whole different
“Fuck!” she screamed out and then massive blasts of cum started to shoot
out from her cock. The first shot caught my chin, the next few got her tits, her
neck, and her belly. I could feel the warm, sticky cum dribbling down my
hand. As she came, her asshole clenched, her hole tightened. I couldn’t hold
back any longer myself. With a loud grunt, I filled her asshole up. She
reached down and massaged my balls as I came. Fuck, I’d never had anyone
do that before, but if felt incredible. Then, she gently put her fingers on my
chin and tilted my head towards hers. “Worth every dollar, right?” she said
into my ear before licking her own cum off of my face.
“Shit yeah.” My head was swirling, my heart was pounding. That was
worth more than every dollar I paid for it. I would have drained my whole
bank account to relive that moment, to relive every second of that moment.
I offered Phan a job with my ring—I even offered her a ninety per cent
royalty on her earnings (most girls only got 75%). But she declined.
Apparently she already worked for someone, someone I’d never heard of. A
guy named Yun Chan. I asked Phan for Yun Chan’s number, so I could call
and negotiate some sort of offer, maybe a trade. I’d give ten of my women for
Phan. But Phan wouldn’t give me his number, or his address, or anything. She
just kissed me on the cheek and said, “Come back for more, okay?” and she
left. I watched her strut back out to the street, turning every head in the
immediate distance. Even I had a hard time peeling my eyes off of her,
wondering if I had it in me for a second fifty-dollar round.
Instead I went back to my home on the hill and started to do some
investigative work. Yun Chan. The name was completely unfamiliar, may as
well have been an alien. An internet search turned up no results. I made a few
calls to my street team, my pimps who were out keeping tolls on my ladies.
None of them had ever heard the name before. It was getting very late, the sun
would soon be up, and I thought of calling it quits for the night. But the
thought of Phan’s perfect body wouldn’t allow me to rest. I needed to have
her. I needed to taste that excitement once more.
I hopped in my car and went back down to her street corner, but she was
gone. I wondered if she was done for the night. There were a few other girls
still out. A few of them made eye contact with me, smiling. One girl gave me
a sampler, flashing her tits before covering up for a passing cop. She had nice
tits, but I was on a mission to find Phan, or Phan’s mystery boss. I continued
down the strip. As I walked past one girl, she reached down and grabbed my
cock. “You want to fuck, honey?” she asked. She squeezed, curling her
fingers around my member expertly. But again, I had a mission.
“Sorry, darling. Another time.” She didn’t like that, releasing me
immediately and turning away.
I turned the corner, passing another whore. “Hey white boy,” the girl said.
I continued walking, then stopped when she spoke again. “You looking for
something extra?” Something extra—that’s what Phan called it, too. I turned
to the girl.
“Extra?” I said. I needed to make sure I was on the right page, that I
wasn’t mistaken. She motioned down towards a bulge in her skirt that just
caught the edge of the streetlight. “It’s extra long, too. Can you handle it,
white boy?” I remembered my time in the car with Phan and my heart skipped
“Who do you work for?”
“You want to fuck or not?” She grabbed her tits and squeezed them. My
God, they looked real, just like Phan’s. Were surgeons in Thailand on another
level or what? How were they producing these perfect female bodies? Or was
there just something in Thai blood that leant itself to feminine features?
Whatever was going on, I was starting to see the appeal.
“Do you work for Yun Chan?” I asked.
“You a cop, white boy?”
“No. Just wondering.”
“Why don’t we just fuck? Wouldn’t that be nice? You want my big dick
your ass? Thirty American dollars.” She reached down and grabbed my cock
and massaged it in her fingers. I melted, surrendered. That was all I could
“Sure. Okay, let’s fuck.” I was a few blocks from my car now and I didn’t
have the patience to make it all the way back, so I took her by the hand and
led her into the alleyway. I hadn’t completely lost touch with my objective. I
still suspected she worked for this Yun Chan character. I knew she wasn’t
going to talk until there was money in her hands. Plus, I was going to get a bit
of action out of it. It was a win-win situation as far as I was concerned.
We were hidden by nothing but the shadows of the buildings around us,
away from the orange glow of the Thai streetlights.
“What’s your name?” I asked her.
Ming was a wildcat, a jungle jaguar, moving expertly and efficiently down
my body. I have no idea how she got my belt undone as fast as she did. I have
no idea what she did with her fingertips to get my cock rock hard in the span
of a few seconds, and I have no idea what she was doing with her tongue to
make my knees tremble and my legs weak. At first I wondered if she was just
employing some learned techniques she picked up from some Thai hooker
school, that maybe she was acting robotically, automatically. But then I
noticed the bulge pushing her skirt out as her cock became hard, rising up tall.
She was into it. She wanted my cock just as badly as she wanted the money.
She looked up at me with hypnotising eyes. She was looking inside of me,
reading my mind, letting me know that she could do anything she wanted and
that I was just along for the ride. Anything she wanted, I was as good as at her
command. She smiled and my head spun. “You like it?” she asked, pressing
the tip of my erection against her chin.
“Yeah, I like it,” I said, my voice shaken, lost in some swirling euphoric
energy. My eyes caught her bulge, now standing tall, the tip of it extending
out from her skirt. Her cock was a shade darker than the rest of her body,
surrounded by a bush of dark trimmed hair. There was something
mesmerizing about it, the way it pulsed in time with her heartbeat.
“You want to suck my dick, white boy?” she asked with a grin.
I didn’t respond. Apparently, I didn’t have to. The next thing I knew, I was
on my knees, her cock in my hand, lips a mere inch away from her tip. Her
delicate fingers ran through my hair. Then, her slick cock slipped into my
mouth, past my lips, along my tongue. It’s warmth throbbed. I sucked, my
body relaxing, mind slipping away. My hands explored her legs and her ass.
One of my fingers pushed up into her asshole, which she seemed to like based
on the soft moan that slipped through her lips. “You suck good, white boy,”
she said, stroking my head.
I lost myself. Time slipped away, irrelevant. I pumped her dick, sucking it
with intensity. I revelled in every pulse, every bulge, every twitch. My finger
slipped further up her asshole. I didn’t even realize I’d been beating myself
off with my free hand until I was moments away from coming. I didn’t even
realize she was about to come until she grabbed a handful of my hair and
pulled my nose tight against her pubic bone. We came at the same time, her
warm cum unloading in my mouth. I gagged at first, then I took it, its sweet
taste on my tongue. It wasn’t until I stumbled back that I realized we never
even fucked, that I’d been too consumed sucking her cock that I forgot about
fucking entirely. “I guess we can fuck another time, white boy,” she said with
an adorable giggle. She pulled her panties up over her dripping cock. I was
about to leave when she said, “Yun Chan is my boss, by the way.” I looked at
her, my mission coming back to me hard. “You asked earlier.”
“Yun Chan? Really? Can you give me his phone number? I need to ask
him a question.”
“Yun Chan has no phone number. Too dangerous.”
“Where is he?”
“I shouldn’t say.”
I grabbed her and pulled her tight to me. “Tell me,” I demanded. She
smiled, looking down at my grip. She liked the rough play.
“I need to know.”
“Slap my ass.”
I stared at her for a moment with puzzled eyes. That smirk didn’t leave
her face. She turned around and bent over. “Slap my ass and maybe I’ll tell
you,” she said.
I slapped her ass, watching her soft cheeks jiggle and turn red. “Harder,”
she demanded, so I slapped her harder. She looked so hot, bent over in that
skirt, those long black fishnet leggings, the tall black heels she’d mastered.
Once her ass was a shade of crimson, she caved. She wrote down an address
on my arm and we parted ways.
I don’t know what I was expecting when I went to meet Yun Chan. The
address Ming gave me was for a Thai soup restaurant. She wrote ‘downstairs’
beneath the address, so I figured the restaurant was a cover, and I was right.
Beneath the restaurant was an impressive space, massive, long corridors,
dozens of basements connected. It was the heart of the Bangkok
Underground. A man who said absolutely nothing when I said “I’m here to
meet with Yun Chan,” led me through a labyrinth of hallways and rooms,
some filled with money, some filled with guns, some filled with women, some
filled with all of those things, some filled with things I didn’t know and
couldn’t name. At the end of one long hallway was a red door. The second I
saw it, I knew it was our destination.
But the room was surprisingly unimpressive: a small, grey boardroom.
Yun, a tall, built Thai man, was sitting in an office chair, leaning back,
laughing as he watched an American soap opera on a corner television. He
didn’t acknowledge my presence until the commercial break. Then, he turned
to me and became very serious, deadpan. “You the guy looking for me? Why?
What do you want?”
“Two girls: Ming and Phan. They work for you, yeah?”
He sat in an intimidating stillness. This man was the real deal, a crime
lord that made me and my associates look like children at the park. I don’t
think I saw him blink once during our meeting. The only movement I noticed
in his body was his throbbing veins, which were visible throughout his bald
head, his thick neck, and his ripped arms. “I don’t know, maybe.” He stared at
me, waiting for me to go on. He probably had people below him who dealt
with his women, kind of like me but on a larger scale, I’m sure. “Why?” he
finally asked. The room was silent. Not even the buzz of a light of the distant
hum of an air conditioner. It was deadening, a vacuum.
“I’m looking to get into the business.”
“Whores?” he asked bluntly.
“Well, I’m already in that business,” I said, and then I thought of the best
way to word my next sentence.
“Ladyboys?” he said for me.
I nodded and shrugged my shoulders. “Yeah, ladyboys,” I said. “I think
it’s an understated business. I mean, I know American tourists would pay far
more than those girls are charging—”
Before I could finish, he said, “You been fucking them?”
I took a moment to respond. “No,” I said. My palms were sweaty. “I
mean, yeah, that’s kind of how I got into this—”
Again, he cut me off. “You can’t have my girls,” he said, and then he
turned back to his program, which was now back from commercial break.
As I went to speak again, one of his men placed a hand on my shoulder, as
if to say, Not during Days of our Lives. So I waited awkwardly for ten
minutes until the next commercial break. It gave me time to try to come up
with a game plan, an offer that would spike his interest. All my thinking was
for nothing, because as soon as his program went back to commercial, he
turned to me and said, “You’re an American, yeah?”
“You know, people pay a lot of money to watch ladyboys fuck
Americans.” His henchmen all chuckled at the question.
“No, no, you see, I’m looking to buy your girls, not for myself, but for—”
Again, I was cut off. “Ten thousand dollars for a show,” he said. “And if
they like you, maybe a bonus on top of that.”
I was silent, instantly considering his proposal. What kind of show was he
talking about? A sex show? Where people watch me fuck a ladyboy? My
brain was screaming at me, Get out of here, you idiot! But I couldn’t deny the
excitement. And the money—ten thousand dollars is a hell of a lot of money,
for a few minutes of fucking. Hell, a lot of people would pay money to do
something like what Yun Chan was proposing. Granted, those were some
“Tonight,” Yun Chan said, turning back to his television. “You can stay
here until the show.”
“I’m sorry, Mr. Chan, but I don’t think I’m interested,” I said.
But he wasn’t giving me the choice. He looked over at me and his eyes
were serious. Behind me, I could feel the presence of a machine gun. I didn’t
need to look back to know it was aimed at the back of my head. And in that
moment, I realized I’d made a huge mistake. I’d chased excitement too far
down the rabbit hole. I’d gotten mixed in with the wrong crowd and now I
was going to pay the price. I envy the people in the world who are happy
being complacent, lazy, unmotivated. People who can reach a modest goal
and then coast for the rest of their lives. All they need is a decent salary and a
little house in the suburbs and they’re good. I wish that was me. But it wasn’t
me. I had to have everything and then some.
I was taken to a room with a cot and a toilet. The only difference between
that room and a prison cell was that prison cells generally had windows in
them. I sat on the cot and waited. How bad could it be? I fuck a ladyboy,
some people watch, and then hopefully that’s enough for them. Besides, ten
grand is a lot of money.
A few hours later, a couple of armed men came to get me. They led me
down a long corridor that must have stretched a number of blocks. Then, we
reached a staircase and I knew it was the place.
They took me up to an auditorium-style room, filled with men in suits and
cigar smoke. There was a man on the floor with a microphone speaking to the
crowd in Thai, and a couple of topless waitresses walking around, serving
drinks. The waitresses had nice tits. I couldn’t help but wonder if they might
be ladyboys too—if every beautiful woman in this country was actually a
Of the foreign words spoken by the announcer, I recognized one:
American. He said it about fifteen times between some other gibberish before
motioning towards me. I took that as my queue to step onto centre stage. No
one clapped or cheered. It was silent, save for the occasional clinking of
glasses and the occasional clearing of a throat. Ceiling mounted lights were
turned my way, making it impossible to see any faces in the crowd. I
wondered if I knew anyone in attendance. It was unlikely, but I knew a lot of
people involved in the crime business, so it certainly wasn’t impossible.
I stood there waiting for something to happen, for some sort of instruction
of what to do next. But there was just an uncomfortable silence. I looked
around, wondering what I was missing, what everyone was expecting. I knew
I was going to be fucking a ladyboy at some point on the stage. Just thinking
about it made my heart rate explode into a frenzy. But I kept my composure
Then I heard a squeaking. At first it was faint and then it grew louder and
louder. A man was pushing an uncomfortable-looking bed on wheels towards
me. He parked it in the centre of the stage and then walked off. Then the
silence returned for a moment. I wondered if I was supposed to get on the
bed, remove my clothes, or just stand there stupidly. I chose to stand there
stupidly, and there was no protest from the crowd, nor was there any sign of
Then came the clicking of heels. It was my date, my fuck, my ten
thousand dollars. I could practically hear my heart tolling against my ribcage.
You wanted excitement, you got it, I told myself. I turned towards the sound
and then I saw her and a wave of relief washed over me. God, she was
beautiful. Everything about her was perfect: her long, smooth legs wrapped
nicely in white stockings, her short skirt, her plump tits squished tightly into
her white blouse—and that face, my God, that face. She could have been a
supermodel, an international celebrity. Instead, she was doing fuck-shows in a
Thai basement. I wondered if that was by choice or if she was being forced.
Hell, if they were offering her the money I was getting, how could she say
Her entrance got a rise out of the audience of one hundred or so—finally.
Some clapping, some whistling, and a lot of chatter. The chatter eventually
reduced to whispers and then, as the beauty approached me, the room became
silent. She stopped right in front of me and looked me in the eyes. I wanted to
say something to her, but my internal systems all seemed to shut down at
once. I was at a complete loss for words as the smell of perfection wafted into
my nostrils. She was a total vixen with her red lips and her long, dark hair.
She leaned forward and gently grabbed my bottom lip with her teeth. A jolt
ran up my spine. She was an ungodly perfection, a masterwork. Her beauty
didn’t belong in that basement, on this planet. My heart stuttered as she
released my lip and I nearly fell over.
She ran her fingertips down from my chest, slowly, sinking her body
down, her knees towards the ground. Her fingertips found the bulge of my
cock. Until that moment, I was worried I wouldn’t be able to get a hard-on for
the crowd. As soon as those magic fingers caressed my length, my cock was
throbbing, hardening faster than it ever had before. She pulled down my fly,
slowly, meticulously. Then she pulled down my pants and my underwear.
Every instinct in my body screamed to stop her, stop her from exposing your
erection to the crowd, but more than anything, I wanted her to fondle me, to
wrap her perfect hands around my cock, to sink my cock through her plump,
Another flurry of whispers broke out in the audience as my cock sprang
free. They came to a silence again as the bombshell slipped my member into
her mouth and began to suck. She knew how to suck a dick, I’ll say that
much. No second was wasted. Her tongue wrapped around my girth and her
lips suctioned me tightly. I could feel the tip of my cock against the back of
her throat, and she didn’t gag one little bit. She worked her fingertip magic on
my ball sack. I swear, I nearly blacked out, between my accelerating heart rate
and the haze of euphoria that was clouding my brain. I sunk my fingers into
her soft hair, pulling her in tightly until her nose pressed against my pubic
bone. Still, she didn’t gag.
She stood up and removed her shirt, eliciting another excited oohing from
the crowd. Who could blame them? The ladyboy’s tits were perfect, two
plump, supple masterpieces. I stared at them in a state of near-hypnosis. I’d
almost forgotten that there was an audience of one hundred staring down at
my erect cock. She pushed me gently back until my legs hit the cot and I sat
down. Then, she climbed over me, planting her knees at my sides, my face
lined perfectly up with her abdomen. I looked up and she was smiling at me, a
smile which I somehow translated into: “Your turn. Lift up my skirt,” so I did.
And then my body became rigid and I stopped. Suddenly I could see what
all the hype was about, why these rich men paid so much for this show. My
date wasn’t any ordinary ladyboy, and not just because she was an absolute
bombshell. She was hung, and I mean hung. Her cock, even flaccid, was
enormous—long, thick, heavy. These people didn’t come to watch me fuck a
ladyboy. They came to watch a ladyboy fuck me—and fuck me stupid. I’d
never had a cock in my ass before, never mind a cock the size of my date’s. It
was going to hurt, no question about that. I was starting to wonder if she was
real or some robot designed by some mad, horny scientist. She was designed
to fuck, designed to draw crowds of wealthy spectators.
My hand trembled as I brought it up to the beast of a cock. I could hardly
wrap my fingers around its impressive girth. And it’s weight… The thing
made my hand look tiny. I gave it a long stroke and watched as the skin pulled
back, revealing her thick, bulbous tip. She took my head and brought it in, but
I wasn’t able to fit it in my mouth. The tip pressed against my lips but
wouldn’t press through. And last I checked, my mouth was wider than my
A pit grew in my stomach. Was this even safe? Had anyone ever been
fucked to death before? Or was I about to be the first, fucked to shreds by my
ladyboy date and her horse-sized cock. She pulled my head in towards her
body and somehow the cock slipped into my mouth. I could hardly breathe as
the warm, throbbing member sunk in deep. I closed my eyes and I
reconsidered everything—my foolish obsession, my need for excitement, love
for money. How had I gone from accidentally picking up a ladyboy prostitute
to being fucked by a world-record-sized cock in front of one hundred
onlookers in the span of a day?
She did the work, thrusting her long dick into my mouth. Unlike her, I
gagged, but it made no difference to her. She wasn’t interested in sparing me,
and neither was the crowd. They were here to see an American being fucked
senseless by their superstar Thai ladyboy, and that’s what they were getting. I
could feel my saliva running down the sides of my face.
A moment later, she pulled her cock out and pushed me down on the bed.
She was hard and her massive cock now stood tall, far past her bellybutton,
nearly touching her supple tits. As she flipped me over onto my stomach with
impressive strength, I wondered if ten thousand dollars was enough for
asshole-reconstruction surgery. She made sure I was facing the crowd before
she climbed on top of me, mounting me, getting ready for entry. I couldn’t see
any of their faces but I knew they were staring at me, excited to see my ass
pulverized by the monster-cock. I felt her saliva covered cock slap down
between my butt cheeks.
Then, I felt it push in, taking my anal virginity from me in a swift push. I
didn’t think it was possible, but the bombshell made it happen. She only
pushed the tip in before stopping for a moment, but it was enough to make me
clench, to make my whole body seize up and for me to groan aloud. I could
hear a unanimous creaking as everyone leaned forward in their seats, not that
they needed to be any closer to see that huge appendage between my
She started to fuck me with just an inch of her cock. Maybe she was just
getting me ready, getting me stretched out before plunging in deep. Or maybe
she was teasing the crowd. Either way, I knew she wasn’t going to stop there.
I knew I was going to get the whole package eventually, if such a thing was
even possible. But I have to admit, the tip of her cock, sliding in and out of
my asshole, felt pretty good. Not just good, but great. After a few pumps, I
felt myself relaxing, the pleasure beginning to build up and pulse through my
veins. I took a deep breath and felt my asshole unclenching, letting her slide
in just a bit deeper.
You know when you have a little, tiny piece of food stuck between your
teeth, like the skin of an apple, and it feels like someone has their whole fist
jammed between your teeth? Well, the asshole, as it turns out, isn’t much
different. My date only had a couple of inches inside of my butt, but it felt
like she had her whole forearm in there, filling me up, stuffed. I became tense
again, clenching, trying to stop her from sinking any deeper. But again, she
didn’t care for me or my feelings. She just cared about getting herself off and
getting the audience off. She pushed past my clenching, deeper, deeper,
deeper, deeper. Hell, I didn’t think she had anything left, but still, it kept
sinking deeper. I swear to God, I could feel her tip pressing up against my
sternum, and at one point, I thought it was in my goddamned throat. Now I
know what a Thanksgiving turkey must feel like.
She started to pump her cock in and out of me. I managed to look back.
Before her hips slapped my ass, they would rise up tall, repeating the process
again and again. At first, I thought it was the end of me. No human could
possibly survive such a pounding. That whole part of the body wasn’t
designed to have anything going in—never mind a foot-long monster cock.
Yet, there I was, taking the whole thing up my asshole.
But after a few pumps, the pleasure came rushing in. My whole body was
consumed by it, a mind-numbing euphoria. I squirmed, bit the pillow, tried to
hold back. I couldn’t bare to scream in front of all of those people. But I
couldn’t hold back. I let go of the pillow and let out a loud bellow. My asshole
had gone completely numb but all over my body was pinging with ecstasy.
Time became a blur. The world around me became a blur. My date pulled out
for a brief moment, flipped me over, and then squished her cock back into my
body and carried on. Now, I could see everything: her tits bouncing up and
down with every thrust, her long cock sliding in and out of my body, her
beautiful face drifting closer and closer to orgasm.
She reached down and grabbed my erection and started to beat me off
while she pumped my ass. Hell, I don’t think it was even necessary. I
probably would have came without it—is that even possible? It sure as hell
felt like it. She only beat my cock a few times before I unloaded all over my
own chest—a massive load of white, sticky cum. Who would have thought
heaven was a grungy basement bellow a Thai soup restaurant?
I could feel her cock swelling, bloating up. She was close to cumming.
Would she do it deep in my ass or would she pull out and drench me in what I
could only imagine was a monster load to compliment her monster cock. She
chose the latter, pulling her appendage out and aiming it at the centre of my
chest, where my own load was already pooled. And I was right, her load was
massive. Cannon fire—load after load—maybe she was a robot, a small
computer up in her brain and the rest of her just an empty shell, filled with
cum that was now unloading on me.
My impulses took control and I reached forward, taking her cock in both
of my hands, getting the final few pumps in. I had to feel it for myself, her
giant member as it unloaded, as it pulsed with every blast. God, it felt
amazing, warm, rigid, powerful. I still couldn’t believe the entire thing had
just been inside of my body, which now felt empty, depleted, like it was
missing something very big. I went limp, my muscles exhausted from being
She crawled over me and gave me a gentle kiss on the lips, her tits pressed
up against my chest, rubbing in our collective cum. I was getting paid ten
grand for this? Fuck, I would have paid ten grand for this! Like a little kid
getting off of a rollercoaster, I wanted back on—I wanted to run right back
into the line and do it again, and again, and again.
Two men came out and led me off of the stage. They brought me to a
shower room and said something in Thai, which I assumed was, “Please wash
all of that cum off of your body.” I did, and then I was taken to the exit and
handed an envelope with ten thousand U.S. dollars. My head was still
swirling, spinning, clouded. I was still riding high, my thoughts unable to
It wasn’t until the next morning, when I woke up in my mansion on the
hill, that I knew what I was going to do next—what the next logical step was
in my hunt for excitement, my craving for adrenaline.
I was going to go and find Yun Chan again. This time, I was going to find
out what I needed to do to become one of his girls—
One of his ladyboys.
HIS NEW GIRLFRIEND
Kyle just lost a bet to his best-friend and now he has to be James’s slave
for the week. How bad could it be? After all, James goes to a different school
where spring break hasn’t started yet.
But there’s a dance coming up at James’s school and James needs a date.
And it just so happens that, with some help from his sister’s closet, Kyle
makes a convincing girl.
It was a stupid bet, a bet I never should have made. Of course the Leafs
were going to lose against the Penguins—why did I think otherwise? Because
the odds were good, that’s why—too good to turn down. But Goddamnit, I
should have turned them down.
Had I won, James would have given me his brand new bike. His grandma
got it for him for his birthday, and it was probably worth close to a thousand
dollars. I needed a new bike, and the one I was in the market for wasn’t nearly
as nice as James’s. I know, I know—I know what you’re thinking. You did all
of this for a bike, Kyle? Yes, I was an idiot. I really thought I was going to
The Leafs were on a winning streak. Auston Matthews scored four goals
in his debut for crying out loud, and Crosby was out with a concussion.
Besides, I really didn’t think being James’s slave for a week would be so bad.
My school was on spring break and his wasn’t until the next week. I figured,
even if I lose, I’ll really only have to be his slave evenings and the weekend.
Had I known he would drag me to school with him, maybe I wouldn’t have
taken the bet. But I did, and I lost. Now, I was bikeless and a slave.
How bad could it be, right? James and I had been friends for years, since
the first grade, back when we were still in the same school. He wasn’t out to
torture me… Or so I thought.
The moment that horn sounded and the Leafs formed a line towards their
locker room, heads down in defeat, my heart sank into my gut. James had a
smirk on his face that suggested he already had the whole week planned out
in great detail. And I was about to find out with certainty that he did indeed.
“You officially belong to James Fischer,” he said to me, that smirk still
resonating on his face.
How bad could it be? How bad could it be? The question was pinging
around my skull. How bad could it be?
“Look,” I said. “We need to set some ground rules. I’m not eating dog shit
off of the ground or anything like that.”
“Nothing harmful,” he said. “That’s fair.”
“And I’m not giving you my money or buying you anything. I’ll go to the
store for you—fine, whatever—but it’s with your cash. Got it?”
“Sure. But you will go to the store for me when I want you to,” he said.
That smirk got bigger. What had I gotten myself into? Goddamnit. He had
something on his mind, something bad. I took a breath. I was psyching myself
I learned a lesson from all of this, I really did. That lesson was: there’s no
shame in backing out of a bet, breaking a promise. I know that sounds bad,
but believe me, sometimes it’s better that way. Don’t be stubborn like I was. I
learned another lesson, too: don’t make bets with James Fischer.
“Why don’t we start with that?” he said. “Go to the store and get me a bag
of chips. Right now. I like Dill Pickle, Lays.” He handed me a five dollar bill.
“Alright, fine.” I stood up and started towards the door.
Then, he said, “Wait!” and I stopped. That smirk—that godforsaken
smirk. There was more. And in that instant, I regretted my idiotic bet. I even
started to regret our whole friendship. “I want you to go in one of your sister’s
dresses.” He was biting his lip, containing his laughter.
My legs trembled. “Are you crazy? No way.”
Then his smirk vanished and he became very serious, brow lowered, eyes
dark. “Don’t back out on this bet! You lost fair and square, and you agreed to
“I’m not going to the store in my sister’s dress.”
“Why not,” he said, that smile returning. “You have that long, beautiful
hair. Why not compliment it with a nice dress.” He laughed. Now I was
regretting growing my hair out. And for the record, some of the coolest men
in history had long hair. Vikings had long hair. Every member of Led
Zeppelin had long hair. Scott Hartnell had long hair, too. There’s nothing
wrong with long hair—but I digress.
“I’m not doing it. But I’ll go get your damned chips.” I turned back
towards the door.
“Don’t do what I say and I’ll show everyone that clip,” he said.
I froze. I’d forgotten about the clip—that fucking clip. A few years back,
James came over to my house, unannounced, and burst into my bedroom with
a video camera. He caught me with my dick in my hand and some bouncing
jugs on my computer screen. So what? Every teenager masturbates—it’s not
like I was doing it out on the street, or watching kiddie porn or anything like
that. I was alone, in my room. And at least once a week since then, James
used that video for his own bidding—blackmailing me over the smallest
things. I was already practically his slave, even without the damned bet.
Thank God we didn’t go to the same school. That would have been a real
What choice did I have? At least at the store, chances were no one would
recognize me. If James put that video out, all of my friends would see it. All
of the girls in my school would probably catch wind of it. I would be
ridiculed and outcast. “Let’s go pick out a dress, shall we?” he said.
“Fine,” I said. “But after this week, that tape is destroyed.”
“Deal,” he said.
My older sister was in college, and for Spring Break she’d gone off to
Cancun with some friends. Meanwhile, my parents were in Cabo. I had the
house to myself for the week, and thank goodness for that. The last thing I
needed was to have my sister or parents walk in on me trying on a dress.
“This one,” James said, picking out a black, skin-tight number. “You’ll
need a pair of shoes, too. Lets hope your sister has big feet.” My stomach
turned. Unfortunately, my sister’s feet were probably around the same size as
mine—maybe a size smaller, but not small enough that I couldn’t cram them
into her shoes. He pulled a pair of black wedges. “I think we have your outfit
for the ball, darling,” he said and then he laughed. Looking at the outfit, I
started to wonder just how bad it would be if my whole school saw that tape. I
mean, it’s not like you could see my cock in the footage, just my back and a
flash of porn on the screen before I clicked away. Maybe no one would care—
maybe they would all understand. Yeah right, and maybe I’m a Chinese jet
pilot. “I’ll give you a minute to change,” he said, and he left the room.
I stared at the outfit. My whole being was rejecting the thought of putting
it on. But Goddamnit, I had no choice. I wanted that tape destroyed once and
for all. I slipped out of my clothes, even taking off my boxers (knowing they
would just bunch up in the tight outfit, which would draw more unwanted
attention to me). Then, I stepped into the dress and slipped it on. After I’d
pulled the straps over my shoulders and awkwardly reached around back to
zip it up, I looked into my sister’s full-length mirror. The damned thing fit
perfectly. Damn my small stature, I thought. If only it wouldn’t have fit, then
maybe James would have found some other punishment for me—something
less humiliating (though, knowing James, that was unlikely). The only issue
with the dress was the bulge of my cock. It was so tight that you could see the
entire contour of my manhood, pressed firmly against my leg. I tried to tuck
it, but it was just too obvious. Also, I clearly had no tits—I was as flat chested
as a teenaged boy, unsurprisingly because that is exactly what I was.
My heart continued to burn inside of my turning gut. I couldn’t believe I
was actually going through with this nonsense. But I had an idea that would
make it somewhat tolerable: if I actually looked like a girl, no one would
recognize me. At worst, they’ll think I’m my sister. We looked somewhat
alike, some similar features (we were made from the same parents, after all).
Or they would think I’m some chick that looked like my sister. But if I could
pull off an authentic female look… First I needed to address the bulge.
I slipped a pair of my sisters panties on. They were tight, but they did they
job, firmly tucking my cock and balls away. Creating tits was even easier.
Apparently (and I had no idea until that very moment), my sister’s bras were
all heavily padded. I didn’t even need toilet paper to look like I had a solid
pair of B-cups. Luckily, the dress didn’t show any cleavage, so no one would
suspect a thing. I looked back into the mirror. Damn. I was actually pretty
convincing. I couldn’t grow facial hair to save my life (thank God for
Swedish parents!). I thought about putting on some makeup, to really sell the
effect, but I didn’t think it was necessary. I already looked terrifyingly like a
chick. Without makeup, I was a solid six—totally mediocre, no risk of turning
any heads. I wasn’t looking for attention after all, I was looking to blend in to
the crowd. To get the job done as quickly as possible, with as little attention
“You done in there or what?” James called out. “I’m coming in.”
He stepped into the room and his eyes lit up. “Holy shit, Kyle!” he said.
His jaw dropped. “You—you actually look like a chick! Damn, son. What’s
the fun in that?” He laughed.
“Laugh all you want. Once you’ve got your chips, this is coming off.” I
walked past him, straight for the front door. I didn’t wait around for him to
add any more ridiculous conditions onto the bet.
It was a few blocks to the store, which gave me some time to figure out
the wedges. They were only a couple of inches tall, but I felt like I was
walking on drywall stilts. It was a long way to the ground, and I was far from
stable. I must have looked drunk to all of the cars that zipped past. But by the
time I reached the store, I had a good stride down.
My sister always watched that show, America’s Next Top Model. I’d been
in the room a few times while she was watching it. On one episode, the host
said something about walking as if you were on a tightrope when you’re in
heels. I tried it out, stepping one foot in front of the next. I caught my
reflection in a large window, and it looked pretty good. I think I was selling it.
Once in the store, I went straight for the chips, wasting no time. With his
stupid Dill Pickle chips in hand, I made my move for the checkout. There was
only one line open, and there were about five other people in the line. Damn. I
was going to have to wait. I thought about stealing the chips, just walking out
with them. I mean, I wasn’t exactly identifiable in my outfit. But what if I was
caught? They would have realized pretty quickly that I was actually a man. It
wasn’t worth the risk. So I stood in the godforsaken line.
A couple of minutes passed by. There were still a few people before me in
the line. Another man had came up behind me and was waiting with his single
microwave dinner on the belt. I made a point of not making eye-contact with
him or anyone. Avoid attention at all costs—that was my new mantra.
Then, he grabbed my ass. It was a gentle grab, discreet, with his full hand.
He got a good handful before pulling away. I leapt up and nearly screamed,
but I contained myself. My voice would have been a major giveaway, and
then everyone around me would have been staring at me. Hell, I think the guy
in front of me lived just two doors down from me, his daughter went to my
school. I had no intentions to go down that road. No way.
I looked back at the man and he winked at me. He was older than me by a
good fifteen years—a full stubble beard and dark hair. He was maybe
handsome by a woman’s standards, but who am I to say? I probably should
have been disgusted but I was in too much shock. His grope was a
confirmation that I was successfully disguised as a woman. Not only that, but
apparently I was a gropeable woman. I bet a lot of ladies go their whole lives
without being groped by strangers in grocery stores, and maybe that’s a good
thing, but after just fifteen minutes, I wasn’t one of those ladies.
I bought James’s chips and left. I could feel the man’s gaze locked on my
ass as I left.
Some energy inside of me erupted. I’d just gotten more attention in fifteen
minutes as a woman than I had in my whole life as a man. Talk about feeling
conflicted. I mean sure, it was negative attention. No woman wants to be
sexually assaulted like a piece of meat. But damn, it felt good to feel
attractive, to know that people noticed you, and not just noticed but admired.
I wasn’t even across the parking lot when I noticed James standing there,
laughing. He’d followed me. He’d been watching from the window the whole
time. “Hey there, Kylie! That guy slapped your ass! Holy shit!” He held his
sides and nearly fell over in hysteria.
“Take your damned chips,” I said, thrusting the bag into his chest. I hated
his satisfaction. Hell, I bet if he put the dress on and did the same thing, no
one would have considered slapping his ass. Deep inside of me, it was almost
a point of pride, a silver lining. But at the same time, I couldn’t wait to get out
of the dress. So I continued on towards the house and the moment I was
inside, the dress came off and my jeans and t-shirt came back on. I was just
happy it was all over. At least I thought it was. But oh, how naïve I was.
It was Monday afternoon, a whole twenty-four hours after the incident at
the grocery store when James knocked on my door and a tingle ran up my
spine. I considered not answering, pretending like I was out. It had been
twenty-four hours of peace, a seventh of my sentence easily served. But I
knew if I didn’t answer, James would let himself in. Was the door locked? I
couldn’t remember. It didn’t matter. If it was locked, he would have found a
window to crawl in through. It wouldn’t have been the first time. So I
answered the door. “What’s up?” I said. There was a small glimmer of hope
inside of me that James had forgotten about our arrangement. It was a
laughable glimmer of hope, but a glimmer none-the-less.
He thrust a piece of paper towards my chest. I took it from him. It was a
poster for the Spring Fling, an upcoming dance at his school. “Friday night,
baby, you and me,” he said.
That tingle in my spine spread through my whole body. “Huh?” I said.
“You’re going to be my date. I was going to ask Kirstin out, but Brett beat
me to it, so fuck her. I don’t need her anyway, seeing as I’ve got you.”
I stared at him for a moment, trying to call his bluff, waiting for a slip—
any slip at all. There was no slip. He was dead serious. He actually wanted me
to be his date. “You want me to go to the dance with you?”
“Not you as in Kyle, of course. I was thinking you, as in Kylie.” He
smirked and that tingle turned into a full-blown tremor. I argued with him and
then he reminded me about the tape and that familiar pit in my gut returned.
Once again, I didn’t have the option. “But we can worry about that on
I thought about it. I knew a lot of people at James’s school, not just James.
A few hours in a packed gymnasium was far more risky than a trip to the
grocery store on a Sunday night. I couldn’t go a whole night without uttering
a word. I would need to work on my voice. I would need to work on my walk,
my mannerisms, everything. But like James said, I could worry all of that
But the more I thought about it, the more outrageous the idea became.
There was no way I could do it, no way I could pull it off. I mean, I didn’t
have the most masculine voice to begin with but people would have caught
on. There would be, after all, a lot of people I knew there—people who knew
me, knew I was friends with James. And if they found me out, it would be
insurmountably worse than that tape reaching the internet. Hell, maybe people
wouldn’t even watch the tape. “No way. Not doing it,” I said. It had been
decided. By a close margin, I would sooner take my chances with the stupid
tape than go to the dance with James, dressed up in my sister’s clothing.
“But the tape…”
“Don’t care. Release it. I’m not going to be your slave all week and then
go to the dance with you and then do God knows what else on the weekend.
This whole bet’s gone too far. Release your stupid tape. See if I care.” I went
to close the door but his foot stopped it.
“Okay, fine. Let’s make a deal, okay? You can have the weekend off. Just
go to the dance with me.”
I considered it. Maybe I could go the whole dance without speaking.
Maybe I could have James tell everyone I was a mute. I nearly laughed at my
own thought—no one would buy that in a hundred million years. But there
would be loud music there, as long as I stayed near the speakers, no one
would be able to analyse my voice. I could show up late and leave early, not
give anyone a chance to dig too deep. Besides, I already knew I made a
convincing woman from an aesthetic standpoint. Maybe it wouldn’t be so
bad. “Just the dance, right?”
“Well,” he said and then he bit his lip. “The dance, yeah, and you would
have to come to school with me this week. Just for a bit, though. You know,
so that people actually believe me when I say you’re my girlfriend.”
“Your girlfriend?” I snapped. That pit in my stomach turned to nausea.
“Okay, so I told everyone I was bringing my girlfriend from another
school. Kyle, you have to admit, you make a hot girl. With a little bit of
makeup, everyone in the school will be so jealous of me. C’mon—help a
buddy out here.”
I could feel my skin turn from pale to green. I had the urge to slap the
bastard but I kept myself under control. “So what are you saying? The dance
and what else?”
“Just make an appearance at school with me some day this week. Come
and give me a kiss on the cheek. Maybe bring me my lunch—say I forgot it at
home. Tell everyone you spent the night—that kind of thing, you know?
Make people know you aren’t just my cousin or something lame like that.”
Oh, the irony, I thought. This was worse than bringing your cousin to the
dance. He was bringing his best friend in drag.
“Not doing it.” Again, I would sooner take my chances with the tape and
be done with this whole slave fiasco.
“Do it and I will destroy the tape and I’ll give you my bike. Promise.”
And once again, that damned bike was the difference maker, the buzzerbeater,
my Achilles’ Heel. I needed a new bike, and it would have been nice
to avoid the release of that tape. So I accepted the deal reluctantly and I
became James’s girlfriend for the week.
I cringed at the thought. I’d become James Fischer’s girlfriend.
If I was going to survive the ordeal, I was going to need to practise, I was
going to have to really become convincing. After James left, I found myself in
my sister’s bedroom, digging through her closet, picking out outfits. My sister
had some startlingly sexy outfits that I’d never seen before and I’m sure she
wished to keep it that way. For instance, what was she doing with white lace
lingerie? What was she doing with a Playboy Bunny outfit? I don’t remember
her ever going as a Playboy Bunny for Halloween.
I tried on a mini-skirt that extended down to about my mid-thighs. It was
white and black striped, like it belonged in a Parisian café. With it, I matched
a pair of black knee-high socks, and a tight black top, once again using one of
my sister’s padded bras to create some tits. She had a cute pair of white shoes
that completed the outfit. I caught myself posing in the mirror, checking out
my ass, my curves. I took a step back and shook my head. Don’t get so into
this, I told myself. Don’t fall any further down this hole than you already
It was frightening. I could suddenly see why some men liked to put on
women’s clothing. It was comfortable. It was sexy. It made me feel great
about myself, about my body. For once, my small stature was being put to
good use. I may not have been able to play football (like James) or basketball,
or any ball for that matter, but I could look like a fox in girls’ clothing.
I shook my head again—again, Kyle, you’re falling too far down, getting
too far lost. Get a grip on yourself. In one week, you will be done with this
Next I was in the bathroom with a box full of makeup and hair products
and accessories. I didn’t know what half of it was, but if I was going to pull
this off, I needed to figure it out. Concealer, that was an easy one. Eye shadow
—pretty self-explanatory. The mascara was a bit tricky but I figured it out.
The deep red lipstick took a few attempts to figure out, too, but I got it
The hair—now that was the real challenge. I’d seen my sister using the
curly wand before, but I had no idea how to use it myself. I turned it on and
tried to imitate what I had watched her do, to no avail. So I unplugged it and
went for the flatiron instead. That was more straightforward. You clamp it
closed and run it down your hair. Then your hair is straight—easy. I even
discovered that, by twisting the iron as you run it through your hair, you can
make big loose curls which looked fantastic as far as I was concerned.
James was right. I was hot. I was a fox. Just staring at myself in the
mirror, I got an erection. It popped out from my panties and pushed my skirt
out. I tried to adjust it back into the thin, lacy undies, but it just popped back
out again. That was something I was going to need to get a handle on. If my
erection popped free during the dance, then I was in real shit—far worse than
a million masturbation tapes.
But for now I was alone. So I reached beneath my skirt and started to beat
myself off. My theory was simple: control it by getting it out of your system.
Besides, how could you not jerk off standing face to face with a vixen like
me? It was like watching a complete stranger, a gorgeous woman who
happened to have a rock-hard erection. She was beating herself off so why
shouldn’t I? I came all over the mirror, a giant, white, sticky load all over my
beautiful reflection. Watching her cock cum like that made my legs tremble.
A few minutes later, my dick was once again flaccid, and I could continue
working on perfecting my female persona. I hit up Google for some tips on
how to sound like a woman. It was surprisingly easy. Maybe it was the years
of choir-training I had, or maybe it was just that my voice was naturally high,
but within an hour, I could do a girl’s voice so well, I could have had my own
I taped myself walking around my garage, practising the voice, and then I
watched the tape. And holy shit, I was a woman. I was watching a woman. No
one would have ever thought otherwise. The only way I was going to be
caught was if my erection sprung out in public—and I was sure that was
something I could avoid.
So I went back up to my sister’s room and started to undress. Then, I
caught myself in the mirror and hesitated. Maybe, I thought, I needed to really
be sure about this, about my persona, before I tried it out in front of people I
knew. Maybe I needed to try it out somewhere safe, where if I was caught, no
one would know who I was and I could get away without too much
I’d never been in a club before. I wasn’t old enough yet. But I’d heard
they rarely checked the girls’ IDs. The bouncer would be my first test. The
question was, could I trick a whole club full of men?
I picked out a clutch from my sister’s closet—white to match my outfit—
and I headed out for a place on the other end of town called Roadhouse.
My heart was racing as I stood in the line-up to get into the club. I could
hear the thud of the bass inside, the hollering, cheering, excited voices of the
crowd, the chattering people waiting among me in the line-up. And over all of
that, I could hear the thudding of my heart against my chest wall. With every
passing moment, I became a little bit more confident. For every second that
no one called me out on being a man, I became more sure that I really did
pass as a woman. A whistling across the street caught my attention, and the
attention of every other woman in that line-up, and the whistler was looking
at me. “Lookin’ good, baby!” he called out as he passed.
I was starting to realize there were lots of men looking my way. As I
looked around, scanning my surroundings, I noticed their faces turning away
quickly, abruptly. Some of them didn’t look away. Some of them kept their
eyes on me. Some smiled. One man winked. They would be searching me out
in the club, I was sure of that. So far the operation was a success.
Then I noticed the bouncer, waving me towards him. I had to check
behind me to make sure it truly was directed at me, and it was. I walked past a
good dozen people towards him. “Yes?” I said, speaking aloud for the first
time in public as a woman.
He said nothing. Instead, he lifted the velvet rope, letting me into the club.
My heart soared. I skipped the line. I couldn’t remember any other time in my
whole life I’d had a similar privilege. And there I was, walking away from
dozens of others, picked out of a crowd, crowned the champion of the line.
It was dark and loud inside, which provided yet another wave of relief. I
could have spoken in my deepest voice and no one would have noticed a
difference. I could probably have walked around with my cock out and people
might not have even noticed. But I wasn’t there to test my limits, I was there
to practice my act, practise my Kylie.
I went to the bar, but before I could pay for my drink, a man stepped up
with a ten dollar bill. “It’s on me,” he said. He has a handsome enough man,
white dress shirt, thick arms, nice stubble beard. He had a charming smile.
“What’s your name?” he asked.
“Kylie,” I told him. I could feel the warmth rising to my cheeks. No one,
my parents aside, had ever bought me anything before. No one had ever made
an effort to woo me, to charm me. And here was Mr. Handsome, just
moments after I stepped out into the public world, buying me a drink, acting
like a gentleman.
“I’m Steven,” he said. “I hope you don’t mind me saying, you look
absolutely stunning tonight.”
I bit my lip to contain my smile. “Thanks.”
He asked where I was from, and I made some bullshit up about being
from out of town. He stared into my eyes as I spoke, though after a while I
was beginning to wonder if he was really listening or if he just was on
autopilot, waiting to get into my pants.
The more and more I spoke, the more comfortable I got. I was in a
rhythm. I was starting to worry I wouldn’t be able to get out of my female
voice, it was becoming so natural so fast. He bought me another drink. And
then another. I’d never drank before—not more than a sip of my dad’s beer
out of curiosity, or a glass of Champaign at a wedding. Now here I was, four
drinks deep. And it was hitting me hard. When the shots came around, I was
lost completely. I tried to cling onto my sense of control, but I was slipping in
and out of conscious presence. The night seemed to jump from moment to
moment, with nothing in between.
One moment we were taking a shot. The next we were laughing. Then we
were dancing. Then we were doing more shots. Then I was in the girls’
bathroom, a beautiful place (relatively speaking), and then I was dancing
again. Then the night became a blur. My senses started to come back to me
when I was in the back of a parked car, I couldn’t tell you where or what kind
of car. I was overtop of Steven, knees planted firmly at his sides. We were
kissing. His face was covered in my smeared lipstick. He kissed my neck and
he grabbed my tits. I must have forgotten that I wasn’t a woman, because I let
him squeeze my non-existent tits, and he must have been too drunk to notice
he was just squeezing a padded bra. But somehow, it felt good—can you
believe that? I could still feel ripples of euphoria from his strong hands
clenching at my chest.
My hand, with a mind of its own, had undone his belt and his fly, and was
now beneath his underwear, fingers wrapped around his cock. He was hard.
He was warm. He was big. I fondled him until he couldn’t get any harder,
warmer, or bigger. I had him moaning and groaning like a puppet, like I was
in total control. Then I realized I was jerking off another man and I stopped,
pulling my hand away. It must have shown on my face because he said,
“What is it? What’s wrong?”
I remained silent, trying to think of something to say, some sort of out.
What was I doing? Was I crazy? All he had to do was reach up my skirt and
he would have realized my truth. And how did I know he wouldn’t get
enraged, beat me to death, run me over with his car and leave me for dead?
“Just relax, baby,” he said, and then he put his hands on my shoulders and
started to push me down, down, down. He was strong, much stronger than
me. Pushing my head down to his cock was no problem for him, though my
drunken body didn’t put up much in the way of resistance.
And there, staring me in the face, was a big, erect cock. And I had the
strange impulse to grab it, to suck it, suck it until it came all over my face. I’d
never even slept with a woman before and here I was about to get it on with a
man. At least he was handsome, I told myself, as if it was any consolation.
Somehow it was. I took the cock and slipped it into my mouth. “Oh fuck
yeah,” he said and his fingers began to explore the hair on my head that I’d
spent so long perfecting.
It wasn’t so bad once I’d gotten started. His cock actually felt pretty good
inside of my mouth, pushing against my lips, sliding along my tongue. And
he was in a whole other state of ecstasy, which made me feel pretty good
about myself. It’s nice to be responsible for another’s pleasure. With long
strokes, I massaged the length of his manhood. With every pump, my body
relaxed. I ran the tip of my tongue along the base of his shaft—that drove him
crazy. Where I learned that move, I have no idea. Maybe from some porno?
Maybe it was just a natural instinct—one of the many feminine instincts that
were now flowing out of me by the dozen.
I had him hypnotised, lost on another plane of reality. Hell, I could
probably get him off without him catching a single glimpse up my skirt, at the
package I was hiding between my legs. So that’s what I did. I closed my grip
on his cock tighter, pumped harder, faster. I worked the tip of my tongue
around the tip of his meat and I watched as he sunk his fingernails into the car
seat. I had him right where I wanted him. There was no way he would cut this
moment of pleasure off for a second, even if it was just for a moment to
quickly transition into my non-existent pussy. I looked up at him.
“You like that, baby—”
Before I could finish my sentence he came, with no warning. His cock
blasted my face, a huge load. He released what I can only describe as a
groaning battle-cry as an ungodly amount of semen launched out of his dick
on my face, onto my top, onto his chest, onto the car seat—everywhere. He
must have been five pounds lighter by the end of his orgasm.
I bit my lip, not realizing there was cum there too. It was sweet and warm.
He caught his breath. Then I remembered again, I needed to get out of there.
This was the definition of being in too deep. “Where are you going?” he
asked, prying himself up into a sitting position. I didn’t answer. I needed to
get home and fast, before the wave of drunkenness kicked back in and I did
something else I would regret—something that wouldn’t end as well as my
romp with Steven had ended.
I found myself back in my sister’s bedroom, staring myself in the mirror,
cum now dried into my top. Holy shit, I thought to myself, I enjoyed that far
too much for my own good. Then, I got into my sister’s bed and I fell asleep.
I showed up at James’s school without warning James. I figured I would
go in, get his stupid little act over with, and then start preparing for the dance.
I didn’t want him wasting my time with planning, telling me what to wear,
how to do my hair, my makeup, telling me what to say. In his original offer,
he just asked that I make an appearance to sell his stupid little lie, so that’s
what I did.
It was lunch when I showed up with a sandwich and a banana in a brown
paper bag. He was at his locker, back towards me. I was dressed to kill, to
turn heads. That morning I’d shaved my legs (even though my blonde body
hair was practically invisible), plucked my eyebrows, waxed my downstairs.
I’d absorbed a few YouTube makeup tutorials and I’d taken my look to
another level. I took my sister’s old school uniform and made a few
adjustments, shortening the skirt, tying the top up in a knot to expose my
belly. I picked up a box of hair dye from the drugstore and I’d given myself
some highlights. I was pretty impressed with myself, to be honest.
More heads than I cared to co