PRETTY CLOTHES
A TRANSGENDER EROTIC ROMANCE
STORY
BY
NIKKI CRESCENT
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COPYRIGHT INFORMATION
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 Inc.
Copyright © 2019 by Nikki Crescent
Model License Holder: Honey Hunter (Shutterstock Inc.)
Background Image License: Whiskey Boone (Shutterstock Inc.)
Cover by Fleetwood Lebowski (Honey Hut Designs Inc.)
All rights reserved. No part of this publication may be reproduced,
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photocopying, recording, or other electronic or mechanical methods, without
the prior written permission of the publisher, except in the case of brief
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uses permitted by copyright law.
NAVIGATOR
Begin Reading
Table of Contents
Newsletter
Copyright
About the Author
TABLE OF CONTENTS
NAVIGATOR
-
PRETTY CLOTHES
CHAPTER ONE
CHAPTER TWO
CHAPTER THREE
CHAPTER FOUR
CHAPTER FIVE
CHAPTER SIX
CHAPTER SEVEN
CHAPTER EIGHT
CHAPTER NINE
CHAPTER TEN
CHAPTER ELEVEN
-
ABOUT THE AUTHOR
DEDICATION
To all of my readers
You have made everything possible
Thank you.
PRETTY CLOTHES
Terry runs a small downtown dry-cleaners. He gets a lot of work from rich
women and working street girls alike. But the rich girls and the working girls
all have one thing in common: they’re always bringing in pretty clothes.
After the busiest night in the history of his small business, Terry decides
to celebrate with a bottle of champagne. During his celebration, he discovers
a bag of pretty clothes that he missed. And with his buzz, he can’t help
himself. Though he doesn’t expect a night of drunken shenanigans to evolve
into a full-blown addiction.
CHAPTER I
Terry hated Mondays because Mondays were always the busiest where he
worked, at the cleaners, in the heart of downtown Vancouver.
Downtown Vancouver was where everyone under the age of thirty went to
party on the weekends—a city with a population of nearly three million, all
condensing into a tight area to drink and do drugs and have sex. And of
course no one wanted to waste their weekend at the cleaners, so they
generally saved that chore for Monday, to ensure their party clothes would be
ready for them again by Friday.
In his five years in the business, Terry had cleaned every bodily fluid
imaginable off of every possible garment. There was one particularly long
week after the Furry Convention, scrubbing dried cum off of large fluffy
costumes—they may have been weird people, but at least they paid well.
A Monday hadn’t gone by in which Terry found himself scrubbing cum
off of some rich woman’s lingerie. It was a thankless job for the most part, but
someone had to do it.
But Mondays did have some perks. The lower class party girls would
come into the cleaners to use the laundry machines, to clean their lower class
party clothes and usually the rest of their wardrobe. It wasn’t unusual for girls
to strip down to their undies and wander around the shop while their clothes
ran through their cycles. One time a girl got completely naked and sat in the
corner with her tits and her pussy out in the open. Terry didn’t complain—she
had a nice set on her—though he was fairly certain that she was a prostitute,
so he made sure to disinfect the machines once she was finished and gone.
Occasionally Mondays were so busy, Terry would end up taking his work
home with him: hauling large sacs of laundry up into his apartment so he
could meticulously scrub the stains from every little piece. He knew that he
should probably turn down the work once the workload was too great, but he
had a hard time turning down the money. The cost of living in Vancouver was
terribly unrealistic after all, and every extra dollar helped considerably.
It was a Monday morning in early January when Terry realized he was
about to face one of those long nights. When he arrived for work, there were
already four people standing at the door, looking exhausted and desperate.
Before he could take their clothes away from them, another four people had
filtered in. One guy had five large sacs of clothes and he wanted every last
piece dry-cleaned. He was willing to pay nearly two grand for the work.
And then it was around noon when the prostitutes started sauntering in.
Mondays were apparently slow for prostitutes, so they generally opted to have
their outfits cleaned on Mondays. The prostitutes always put in rush orders.
“You know the drill,” said the bubbly blonde who came in every week at the
same time. “I need everything before tomorrow at lunch.” One time she
offered to pay Terry with blowjobs, but he declined the offer—he’d never
fooled around with a prostitute and he was proud of that (and his medical
records were also proud of that).
And shortly after the prostitutes came Vancouver’s female gymnastics
team—another five sacs of stretchy outfits that needed hand washed one at a
time. And after the gymnasts came the barrage of tourists from a recent
arrived cruise ship. And after the cruise ship came all of the young girls who
had arrived a day early for the Justin Bieber concert. The day just wouldn’t
end.
Terry was quickly overwhelmed—too overwhelmed to realize he was
becoming hopelessly overwhelmed. When his alarm buzzed to let him know
it was 8:00PM—closing time—he had eighteen sacs of clothes behind him
that needed cleaned in the next ten hours. It was clear that Terry wasn’t going
to be getting any sleep. It was almost 10:00PM when Terry finally settled into
his home, after making three trips back and forth, hauling heavy sacs of
clothes. Before starting on his first sac, he fired up the coffee maker, filling it
to the brim with strong coffee—so strong that the grinds would get stuck
between his teeth.
And then he got started, one piece at a time. He prioritized his usual
clients. The Justin Bieber fans weren’t a high priority—they were only in
town for a couple of nights—same with the cruise ship tourists. Though he
didn’t want any negative Yelp reviews, so he planned on finishing the whole
haul that night.
It took a whole hour to get through that first bag. His eyes were already
heavy and he caught himself nearly nodding off a couple of times. So he put
on some aggressive music—music he didn’t even like but he knew would
keep him awake. He found himself in a sort of exhausted trance, going
through the motions, trying his hardest not to look at the giant piles of clothes
that awaited him, or at the small piles of clothes that were finished. He
reached out for his coffee, which he was drinking straight from the pot, and
found that it was empty. So he quickly brewed another pot and kept going.
The sun was up when he finished scrubbing that final little stain out from
that final signed Justin Bieber t-shirt. He took a deep breath and fell onto his
couch, dozing off for just ten minutes before his alarm began to chirp. It was
time for work; time to do it all over again.
CHAPTER II
Tuesday was quieter than Monday. Clients came to pick up their orders,
and few came to drop new orders off. Terry found himself wandering over to
the café next door nearly half a dozen times before noon, and then he finally
stopped when he realized his hands were physically trembling. He started to
wonder if a person can die from consuming too much caffeine.
He was shocked when there were no complaints—not a single dissatisfied
customer. Apparently he’d done a good job in his state of overwhelmed
exhaustion. One woman even gave him a fifty dollar tip after saying she’d
gone to ten different cleaners and no one was able to get the stain out from her
four-thousand dollar dress. Terry couldn’t even remember cleaning a fourthousand
dollar dress, and he couldn’t remember any difficult stains, but then
again, he couldn’t remember much except for the taste of burnt coffee
grounds.
It was around 5PM on that Tuesday when a pretty, young woman came
into the shop. She walked up to the counter with a precious smile on her face
and said, “I’m here to pick up my order.” Terry didn’t recognize the girl, but
she had a tag, so Terry went into the back to retrieve her clothes. But there
was no order with her tag number on it.
“When did you drop the clothes off?” Terry asked, assuming he’d
mislabelled one of the orders in the tired chaos the night before.
“Just last night.”
Terry strained to remember the girl’s face, but his mind was silent. She
didn’t look at all familiar. “What exactly did you drop off? I’m sure it’s back
there—I must have just mixed up my tags.”
Her cheeks became a shade of pink. “Well,” she said with a suddenly coy
voice. “There was a couple dresses, a couple of skirts, a bodysuit, and…” Her
cheeks turned even pinker. “Some intimate items.”
Now Terry felt his cheeks becoming warm. He cleared his throat, but that
didn’t stop his voice from cracking when he said, “I’ll go look.” But there
wasn’t much in the back—just a few sacs from his usual clients. He looked
through them anyway.
And then it dawned on him that the girl was possibly one of the
prostitutes, now out of makeup. It’s amazing what those girls can do with
makeup—they can completely transform themselves, and make themselves
completely unrecognizable. But it was hard to believe the little blonde
standing in the waiting area was a prostitute. She seemed too harmless and
too gentle.
Terry grabbed an item from each of the bags he had in the back, and he
brought them out. He held them up for the girl, and then he watched as she bit
her bottom lip and shook her head. “Those aren’t mine,” she said. And now
Terry felt embarrassed, holding up slutty hooker outfits for a harmless little
blonde.
“I’m so sorry—I’m sure I have them somewhere. Do you need them now?
Can you come back tomorrow for them?”
She smiled and nodded her head. “I’ll be back tomorrow,” she said, and
then she skirted out of the store.
Terry took a two-hour nap as soon as he got home. Then he woke up and
ate the first food he’d eaten in almost thirty hours (and he didn’t even realize
he hadn’t eaten anything until he shoved that first forkful into his mouth).
After a few bites, his brain started turning on again. He remembered a bit
more from that chaotic night and the day that preceded it. But he still couldn’t
remember that girl.
He cleaned up his dinner dishes and then he went looking through his
house for the missing bag of clothes. He fished that order tag out from his
pocket and examined the number. The girl couldn’t have been lying—the tag
had yesterday’s date on it, written in Terry’s handwriting. But where could the
bag have ended up? Did he drop it on the street during one of his many backand-
forth trips to the shop? His gut turned at the thought. It had been years
since he’d ruined a client’s clothes, and he’d never lost a client’s clothes
before. What would he say to her? Would he pay her to cover her losses? She
apparently had a whole sac of clothes, probably worth well over a thousand
dollars—much more than Terry made from his long, exhausting night… One
little mistake and all of that work was for nothing.
Terry bit down on his tongue. Maybe he could find the bag. Maybe he’d
dropped it in the stairwell of his apartment building. The elevator was broken
and had been for weeks, so Terry had been hauling sacs of clothes up and
down the fire exit stairwell. So he went to look, but it wasn’t there. He ran
back down to his shop, checking every alleyway for a stray brown sac, but
there was none. If he dropped it on the street, someone had surely grabbed it,
probably hoping to make a few bucks at a local pawnshop.
“Shit, shit, shit,” Terry muttered under his breath as he made his way back
to his home.
He was running low on energy as he climbed back up to his apartment. He
threw open his apartment door, ready to collapse on his couch and accept
defeat, and then he noticed the glimmer of brown squashed behind his sofa
chair. He ran over and pulled it out, and his face lit up as he could feel the
clothes inside of the bag. There it was—the missing bag!
He hugged it tightly and thanked a god he didn’t even believe in. Then he
opened the bag up and pulled out the clothes. They still needed cleaned, but
that was no issue—nothing he couldn’t do in the next hour. He pulled out two
soft satin dresses and then he pulled out a cute lace skirt, and then he pulled
out the tight black bodysuit. All of the clothes smelled nice, like expensive
perfume, and there were no stains that Terry could spot.
Before he got started with cleaning the blonde’s clothes, he went over to
his fridge. He had a small bottle of champagne in the fridge that had been
there for two years. He meant to drink it when he opened his shop, but he
hadn’t gotten around to it. Now he was ready to drink it, after his most
profitable (and longest) day in business. He felt he had a good reason to
celebrate.
So he took a long swig from the bottle. And then he took another. The
buzz felt so good, he decided to finish off the whole bottle with a big grin on
his face.
CHAPTER III
When Terry returned to that final job of the night—that sac of pretty
clothes sitting in the middle of his living room—he was drunk. He stumbled
slightly, unable to wipe the grin from his face. Usually, a single small bottle of
champagne wouldn’t have been enough to even give him a buzz, but that
night was different. That night, he was running off of almost no sleep and
he’d hardly eaten in two days. If he’d had just another shot of booze, he
wouldn’t probably end up blacked out.
He picked up that first dress: a knee-length red bodycon dress with a cut
slit up the left side. He scanned it carefully for stains and found none. Then he
danced it over to his steam cleaner as if there was a beautiful woman wearing
it. Before placing it down on the rack, he looked down into his imaginary
girl’s imaginary eyes and said, “You look stunning tonight.” And then he
laughed and fired up his steamer.
He made sure to run the steam evenly over the whole garment. You have
to be careful with red satin—a steamer can easily discolour a spot if held for
too long or too close. Once he was done steaming the little number, he flipped
it inside out and inspected the seams. There were a few loose threads, so he
pulled them in and knotted them off, making sure the cute dress would last
another few years at least. It was a little service he included for all of his
clients.
Then he hung the dress on a hanger and went to get the next little number:
a black dress that was even shorter than the red one. He found himself looking
at it, wondering what purpose it served. It was far too short to wear to work,
or even out on the street. Was it a bedroom dress? Did the girl wear it with her
husband? Terry tried to remember if the pretty blonde had rings on her finger.
He couldn’t recall any.
He held the dress up to his own body. “How do girls even fit into these
things?” he asked aloud to no one. And then he got a silly, drunken idea in his
head. He let a giggle slip before getting himself undressed. He now had a
curiosity stuck in his head that wouldn’t go away until he indulged, and he
wasn’t in a straight enough state to stop himself from indulging. He got
himself completely naked and then he started to wriggle his body into the soft
satin dress. It was tight, and he was careful not to rip it (as careful as a drunk
man can be). He pulled it up slowly, awkwardly fighting his arms through the
armholes.
He let another giggle slip once he had the dress on his body, though this
was more of a giggle of surprise than an acknowledgement of how ridiculous
he was being. The dress actually fit. The satin was actually stretchy enough to
snap over his body—though maybe he shouldn’t have been too surprised. He
wasn’t a big guy by any stretch of the imagination—only a few inches taller
than the blonde who owned the dress, and probably only twenty pounds
heavier. And it helped that he hadn’t eaten much at all in a couple of days.
He laughed all the way to his bedroom, where he had a full-length mirror.
And then he stopped laughing when he saw himself. Aside from his body hair
and his stubble beard, he didn’t look half-bad in the little dress. It just hardly
covered his cock, but the bulge wasn’t too noticeable. He found himself
standing there for a few minutes, trying to convince himself that he didn’t
look good. But he just couldn’t help but notice his curves and his surprisingly
supple ass.
And now he had another strange and silly curiosity in his head: how
would he look with a full-body shave? It was another curiosity that he knew
wouldn’t go away until he indulged, and he was still too buzzed to stop
himself from indulging. So he ended up in the bathroom with his face razor
and plenty of shaving cream. He giggled while shaving the hair off of his
legs. His crotch suddenly looked silly, all hairy above his bare legs, so he
shaved his crotch too. And then he shaved his chest and his armpits and then
his neck and his face. He went over everything twice, making sure he got the
closest shave possible, to make sure the look was as convincing as possible,
even though he was hoping to look in the mirror and see a ridiculous sight,
just for a good laugh.
But that’s not what he saw. When he looked in the mirror again, his heart
fizzled down into his stomach. Now he really looked good in that dress. When
he blocked out the sight of his face, he was looking at a woman (with a slight
bulge). He was suddenly regretting indulging in his sudden curiosity—and it
didn’t help that his buzz was wearing off. Now he was a sober man with
shaved legs and a shaved crotch, standing in a woman’s dress. But even sober,
he thought he looked pretty good.
He took the dress off quickly and brought it over to the steamer. He
wasn’t giggling anymore. Now he just wanted to be finished so he could go to
bed and forget all about his silly shenanigans. But he still had a fair amount of
work left: two skirts, the bodysuit, and a few lacy bedroom pieces. And it
wasn’t long before those urges came back. Terry was walking that tight black
bodysuit over to his steamer when he started to wonder how it would look on
him, paired with one of the skirts. He tried to fight the urge to try the little
outfit on. He knew that once he had the items cleaned, the urges would be
gone—he wouldn’t waste his hard work by wearing cleaned clothes. But right
now they weren’t clean—they still needed cleaned, so in a way, Terry could
do whatever he wanted. He knew it wasn’t a proper justification, but it was
enough to make him a little bit crazy.
So he got naked and he slipped into the bodysuit. He used a couple of
socks to create the illusion of a bust, and then he slipped a pink skirt up his
legs. The skirt extended almost to his knees, and the combination was actually
quite cute. It made him look more petite and strangely firm. He found himself
bouncing up and down with his butt facing the mirror, watching his bum
bounce the way a curvy model’s might. He covered his face and made a few
little poses. He even took out his phone and took a few mirror selfies, making
sure not to get his face in any shots. Looking at the pictures, he was sure that
anyone would have thought they were looking at an actual chick and not a
twenty-nine year old man. And that thought brought a strange smile to Terry’s
face.
He took the outfit off and got it steamed and sprayed and hung up. Then
there was just one skirt and some lingerie left to clean. And Terry knew,
before he even got to the sac of clothes, that he wasn’t going to be able to
resist the urge to try on the lingerie.
CHAPTER IV
The lingerie fit surprisingly well—even better than the dress and the skirt
and the bodysuit. The first piece of lingerie was a whitish pink one-piece with
lace arms. Every bit of that lacy number hugged Terry’s skin, and even though
it was tight, it felt amazingly comfortable. Once again, for the third time that
night, Terry found himself in front of the mirror, ogling his own ass, trying to
figure out how he’d never noticed his own rear-end before.
Then he had another wacky idea. In his kitchen he had a set of washable
children’s markers that his little nephew had left there a few weeks before. He
grabbed the black one and slipped into the bathroom. He carefully drew the
marker on like eyeliner, and the effect wasn’t bad. He went to wipe a small
mistake and ended up smudging the whole thing, so his faux-eyeliner turned
into faux-eye-shadow. He rubbed it all around until it actually looked like
eye-shadow, and then he went and tried again for the eyeliner, and this time
the result wasn’t half-bad.
He rubbed a bit of red onto his cheeks, which looked too clown-like, so he
went and tried to wash it off. The mostly-washed-off version actually looked
like blush, so he kept it.
Next he dug an old Halloween wig out from his closet. It was a blonde
Viking wig, which looked a bit silly until he got a trucker cap on top of it—
then it was passable. And he actually looked pretty cute with a long blonde
braid.
He was having fun, and he’d completely lost track of time. He got the one
piece steamed and sprayed and hung up, and then he pulled out the final
outfit: a black lacy two-piece, with a matching black lacy pair of cat ears. The
outfit seemed silly at first, and then he got it on and realized it was actually
hot. There was even a choker at the bottom of the bag, which he figured went
with the ensemble, so he put it on. He took some more photos, this time
getting his face in the shots. And then he admired the photos and after ten
minutes of admiring the photos, he realized his cock was rock solid. He went
to his bedroom and looked in his full-length mirror. He had a good laugh at
his erection, which ruined the feminine illusion.
And then he had another strange urge: to jerk himself off while staring at
his own reflection. He bit his bottom lip as his fingers curled around his hard,
throbbing meat. He let a grin slip as he pulled his foreskin back. He couldn’t
remember the last time his cock was this hard. It was already drooling a warm
drop of pre-cum. He took a deep breath—he knew he wasn’t going to last
long. And he was right. After just a single minute of slow rubbing, he came
all over his mirror. He squirmed and groaned and then he realized he’d just
jerked off while wearing a female client’s lingerie.
His eyes were wide and his lips were parted. Reality suddenly slapped
him in the face. He got out of that little outfit as quickly as possible. He got it
cleaned and hung up and then he threw himself into his bed and buried his
face into his pillow. Before falling asleep he managed to convince himself
that he was just acting crazy because he hadn’t slept in nearly forty hours. It
was just an exhaustion-induced psychosis—nothing to worry about. Right?
The little blonde came in around noon that Wednesday to pick up her
clothes. She didn’t bother inspecting her haul before leaving—it was rare that
girls did inspect their clothes before leaving when they had lingerie. But while
she was paying for the order (which Terry discounted), Terry couldn’t help
but imagine her wearing that black lacy two-piece with the cat ears. It was
hard to imagine her in anything but a sweater and a pair of jeans. She seemed
way too innocent to be wearing anything lacy or tight or even a little bit sheer.
His cheeks were warm as he handed her the receipt. Once she was gone,
he went to the bathroom and splashed some cold water on his face. He had
thoughts in his mind that weren’t welcomed, and they refused to go away.
Though he managed to make them go away for a couple of hours—until a
beautiful woman walked into the shop with a wardrobe bag full of skimpy
dresses. “I need them all cleaned by Friday,” she said with her big sunglasses
still on. “And be gentle with the panties—they’re all for a photo shoot I’m
doing this weekend.” As she walked out the door, Terry found himself sizing
the woman up, trying to figure out if her clothes would fit him.
And once the store was empty, he found himself perusing through her
wardrobe bag, feeling the soft satin of her dresses, admiring the curves and
tapering of each item. At the bottom of the bag were the panties: a pair of
white crochet panties, a pair of black lace panties, and a pair of red satin
panties. There was a white lace bra and a black lace bra, and a note that read,
“If any of these come back faded, I’ll be expecting a full refund.” She even
left the original receipts in the bag.
Terry squirmed. He was jittery with excitement—he couldn’t wait to get
home and try the outfits on. But he didn’t want to try them on. He didn’t want
to be excited about putting on women’s clothing. It was weird—not just
because the clothes didn’t belong to him, but also because they were for
women. Terry wasn’t a woman. He wasn’t gay and he wasn’t a cross-dresser.
He liked girls and he liked being normal. And now, after a full night’s sleep,
he was still having these strange, unwelcomed urges. Why wouldn’t they go
away? What did he have to do to make the urges stop?
He had the time to process the woman’s clothes at the shop that day, but
he chose not to. He chose to take the haul home and run it through his home
system, just so that he would have the option to fool around a little bit if he
wanted to. But he wasn’t giving himself the option by taking the clothes home
—he had already made up his mind, no matter how hard he tried to convince
himself otherwise. He didn’t even have the steamer fired up before he started
getting undressed, with the blinds closed and the front door locked.
He told himself that it would be a waste not to get dolled up in the
woman’s clothes. It was his chance to try on some expensive designer dresses
while his body hair was still non-existent. He’d already told himself that he
wasn’t going to shave again. He would let his beard and his body hair grow
back out, so in a week or two, any piece of women’s clothing he tried on
would look silly. But until then, why not have a bit of fun? He did go through
the trouble of shaving his whole body, after all.
So he started with a black cocktail dress. It was soft on his skin and the
straps were incredibly thin and dainty. It looked a bit weird without a bust, so
he put on one of the woman’s bras, stuffing it with socks to create the right
illusion. Then he did a few poses in the mirror, but was distracted by his
bulge. The dress was so thin and light that it showed off every little bump and
curve, including the bump of a mosquito bite on his thigh. He solved the issue
of his cock’s bulge by slipping on the pair of red satin panties that were at the
bottom of the bag. They were tight and snug, but incredibly comfortable. It
was only a minute before he started feeling them tighten, stretching around
his growing cock. He was becoming erect once again at the sight of himself.
He tried biting his tongue and pinching his arm to make the erection go away,
but he was aroused and there was nothing he could do about it—nothing
except for deal with it.
He remembered the night before, how sanity returned to him as soon as he
came. So he just needed to come again. He hiked up his dress and slipped his
cock out from the red panties. Then he started stroking, watching himself in
the mirror.
And that’s when he got a new idea—another unwelcomed idea that
pushed his newfound fetish to a new extreme. There was a black handle
sitting on the dresser next to his bed—the old handle from his steamer, which
he’d recently replaced. The handle just happened to be about eight inches
long and almost an inch thick—not too much different from the dimensions of
his own cock. And it was smooth and rounded at the end. Terry picked it up
reached it down slowly, rubbing it between his legs, teasing the tip against his
butthole.
He’d never been penetrated before and he was proud of that fact. But that
didn’t make the sight of him rubbing the phallic object along his anus any less
arousing. He pushed it up and down and up and down and then he slipped it
under his panties and rubbed it directly against his now-puckering hole. His
jaw and hands were trembling and his cock was throbbing harder than ever
before, oozing warm pre-cum onto the red satin panties, which were probably
worth four hundred bucks.
He knew he had a little bottle of spermicidal lube in his nightstand. With
enough lube, he knew it wouldn’t hurt. It would probably feel weird and
uncomfortable, but it would look hot in the mirror—and that’s exactly what
he wanted. So he grabbed the lube and squirted a healthy dab onto the tip of
the steamer handle. And then he pushed the handle back under his panties and
started twisting it against his puckering asshole. His heart stuttered and leapt.
He took a deep breath.
“What are you doing?” he whispered to himself. His cheeks were dark
red. He couldn’t stop himself. An intense sexual energy had taken over his
body and now he was stuck watching like a prisoner trapped in his own skin.
He closed his eyes and continued to mash that dildo-shaped object into his
hole. It only took a little push to make it penetrate. He gasped and then bit
down on his tongue. It felt weird inside of his butt, but it didn’t hurt. After
letting a slow breath out, he opened his eyes and stared at himself in the
mirror. He was sitting on his bed with his knees up. His erection was
throbbing on his stomach and that handle was pushed one inch into his butt.
He wanted to see it go further, so he pushed a little bit more and watched it
slowly disappear.
And that’s when he noticed the grin on his face. He was enjoying himself,
enjoying watching as he became emasculated, enjoying his own humiliating
feminization. Where did this fetish come from? Was it always there, lying
dormant, waiting for the right moment to come out? He had to let go of his
cock, worried another stroke would make him come. He didn’t want to come
yet. He wanted to enjoy the moment a little bit longer.
He pushed the handle in deep and then he pulled it out. He liked the sight
of his asshole hugging the handle, pulling up with suction. And he loved
watching that handle disappear again, back down that hole. Why did it look so
hot?
And why was it starting to feel so good? Terry let a little groan slip. He
pulled his knees up further and bit down hard on his bottom lip. “Oh God,” he
moaned. And he couldn’t look away from his body. He didn’t want the
moment to end and he didn’t even want to blink to miss a millisecond of the
action. “Take it, baby. C’mon—just like that. Take it.” It took a moment
before he realized he was talking in a feminine voice—one that he’d never
practised before in his life. His cheeks were suddenly a shade of red, without
the help of any washable children’s markers.
He reached up and cupped one of his fake tits. He squeezed it hard as he
rammed his DIY dildo into his ass. He was squirming, in a state of pure bliss.
And then suddenly, his cock erupted and sprayed his body with warm goo. He
hadn’t even touched it in minutes, but apparently some anal stimulation was
enough.
And it wouldn’t stop. He just kept coming, coating that expensive dress in
white cum. He groaned and squirmed and tilted his head back and pushed that
dildo in just a little bit harder so that it was pressing perfectly against that
sweet spot. Then that reality he was looking for finally found him.
He looked down and saw the cum stain on that nice dress, not to mention
the oily lube stain on the red panties, or the little snag on the right breast cup
when he’d been squeezing and digging in his nails.
He took it all off quickly and rushed it to his cleaning station. It was going
to be a lot of work, but he could fix it. He could make it look as good as new,
as if he’d never put it on and jerked off on it. His face was dark red as he
carefully scrubbed away the jizz. He was beginning to lose himself to his new
fetish, and he had a feeling it was only going to get worse.
CHAPTER V
Terry struggled to smile as the woman came to pick up her clothes. She
placed the wardrobe bag down on the counter and took each item out
individually. She looked at Terry for a moment with an unimpressed look and
then she looked back down at the very dress Terry wore and came on. Terry’s
heart stuttered. “Is everything okay?” he asked.
It took him over an hour to get that stain out, and miraculously he
managed to do it without discolouring anything, at least as far as he could tell
in his dimly lit apartment.
The woman kept staring at the dress. “It looks fine,” she said. And then
she left the store, finally allowing Terry’s heart to beat again. He took a deep
breath, and then one of his usual clients walked into the store: Sheila, a
prostitute who worked around the block at a ‘massage parlour’, which was
actually just a brothel.
Sheila went straight to her usual machine and shoved her whole sac of
lingerie inside. Then she went across the street to grab a coffee while the
cycle ran out. And Terry sat mesmerized by the spinning red and pink and
purple lingerie inside of the machine. Every time the machine stopped for a
brief moment, he could see a glimpse of what she wore the night before while
getting rammed by God knows how many men. There was a purple one-piece
that especially caught his eye: cut in a V-shape from the shoulders to the
crotch. It looked like the perfect outfit for Sheila and her small, perky tits—
and the perfect outfit for Terry and his non-existent tits.
When Sheila came back, Terry snapped out from his daze. He looked
down at his newspaper and pretended like he’d never looked away. He didn’t
look up again until he heard Sheila mutter, “Damnit. I think it’s just ruined.”
She was holding up that purple outfit, looking at a small dark stain on the
stomach.
“What’s wrong?” Terry asked.
She looked over and smiled. “Candle wax,” she said. “Should I just throw
it out?”
Terry got up and walked over. He took the outfit from her and looked at it.
“I can get this out with a bit of work.”
She laughed. “No offense, T, but I ain’t got the money for that.”
Terry smiled. “I’ll do it for free. It’s a slow day anyway. When do you
need it by?”
Sheila had a hesitant smile on her face. After a moment she shrugged her
shoulders and said, “Okay, sure. Thanks. I’ll swing by tomorrow and grab it,
if that’s okay. You sure you don’t mind fixing it for free?”
“Not at all,” Terry said with a big, red-cheeked smile. Sheila didn’t know
that she was paying him, just not with money. She was feeding into his new
fetish, his new addiction.
But the shop really was slow that afternoon—so slow that Terry decided
to close down an hour early. He had nothing to take home with him except for
that purple piece of lingerie, which he kept in a plastic bag. He was halfway
home when he noticed the makeup store he walked by every day was still
open. He couldn’t remember the last time he’d seen it open; usually, they
didn’t open until after Terry and they always closed before he was finished
work. In the window was a sign: ‘Half off old stock, today only.’ Terry’s heart
stuttered. A bit of makeup would really bring his new addiction to the next
level…
So he found himself in the store, wandering awkwardly down the isles of
items that were completely alien to him. He bit his tongue when he came
upon a section of makeup kits. Most of them were for teenagers who owned
nothing, and some of them even came with instruction manuals for the
different items: exactly what Terry needed.
One of the store clerks nearly made Terry jump into the air when she
tapped on his shoulder. “Can I help you with anything?” she asked. Terry
spun around, his heart pounding. He forced a smile.
“My daughter just turned eleven and she wants to start wearing makeup.
I’m against the idea to be honest, but my wife keeps insisting that all the other
girls are doing it.” He tried to force the biggest smile he could. But he felt off,
as if the girl could see right through him, as if she knew he was actually
looking for himself. He looked down at his plastic bag and could see a tinge
of purple poking out. His heart fluttered into his stomach.
The store clerk smiled. “Well most teens wear makeup these days—and
lots of pre-teens like your daughter, too. I would recommend this kit here. It’s
got all of the essentials.”
“Perfect, I’ll take it,” Terry said without even looking. He was too
overwhelmed, too out of his element. He just wanted to get out of there so
that the embarrassment could start to subside. It wasn’t until he was back at
his apartment that he realized the store clerk probably could see right through
him. There were kits for sale at the makeup store that were obviously for
young girls: pink kits with pictures of Barbies and whatnot on them. But
that’s not what they sold to Terry. The kit in Terry’s hands now was more
mature: all black with fancy gold calligraphy. The brushes were all thin and
fragile-looking, and there were no instruction manuals with anything. So it
took Terry a good couple of hours to figure out what it was all for, and how to
put it all on. It took the rest of the night before Terry was satisfied with his
new look: a smoky cat eye look with carefully filled-in eyebrows.
He never realized how blue his eyes were until he had that mascara on his
eyelashes. And he’d never realized how big and stunning his eyes were either.
With a bit of red lipstick, he looked like a completely unrecognizable person.
“Looking good, sugar,” he said with his surprisingly sharp female voice. He
caught himself grinning in the mirror before turning to his plastic bag to pull
out the highlight of his night: the prostitute’s purple lingerie.
It fit nicely, and it looked good even without socks stuffed into the chest.
He did a few poses in the mirror and suddenly felt a naughty sexual energy
flowing over him. How many men had came on that little outfit? How many
cocks had rubbed up against that tight lace? Terry reached down and ran his
fingertips between his legs, feeling that well-used and well-fucked fabric. His
cock was suddenly rock-hard, throbbing, and leaking.
He quickly retrieved his black steamer handle and his little bottle of lube.
He was ready and excited for another round of ass fucking. But before he got
the handle lubricated and in his asshole, he teased it with his tongue and
pressed it into his mouth. He gave it the hottest blowjob he’d ever watched in
a mirror and then he didn’t bother with the lube—he didn’t need it. His saliva
was enough for his tight little asshole. It hurt just a little bit at first as he
stretched wide to accommodate the faux-dildo, but after thirty seconds of
thrusting in and out, it started to feel good. He wanted to make himself come
again without using his hands. He wanted to fill that tight little outfit with
warm jizz, and this time it didn’t matter if it didn’t come out. He could just
tell Sheila he wasn’t able to salvage it—she was going to throw it out anyway.
Hell, maybe then he could keep it for himself. Maybe he would just tell her it
wasn’t salvageable regardless of whether he could get the cum and candle
wax out.
He felt it coming. His body tensed up and a jolt of warm euphoria
overwhelmed his nerves. He started squirming and trembling and then he felt
his warm go splattering across his chest. “Oh God,” he groaned as he rolled
onto his side, his eyes nearly rolling into the back of his head.
And then he caught a glimpse of himself in that full-length mirror, looking
beautiful and amazingly convincing. He found himself frozen, obsessed with
his own reflection. Was he really that convincing, or was it just a good angle?
He moved and found himself mesmerized once again. The purple lingerie
looked so good on him, like it was made for his curves and his perfect bum.
CHAPTER VI
Terry was beginning to scare himself. In a matter of days, he’d gone from
being completely disinterested in trying on women’s clothing, to not being
able to think of anything else. Every time a girl came into the shop with a sac
of clothes, he would dig through it, hoping to find pretty clothes he could take
home and try on. He was always disappointed when the customers said, “I
need these back later today.” But still, by the end of the day, he had six sacs to
take home with him—six sacs that could have been cleaned in the store, but
Terry wanted to save for the privacy of his own apartment.
As he walked through his apartment door, he realized he wasn’t going to
get much sleep, even if he decided not to try on the various outfits—his
addiction had left him with more homework than he could handle.
But of course he spent the next few hours trying on different outfits. He
put on a cute skirt and a tight cardigan while he made himself dinner, and then
he ate his dinner wearing a black satin cocktail dress. He was digging through
the sacs for a third outfit when he had a peculiar idea that brought him to his
laptop computer. It only took a little bit of searching before he found out
hormone replacement drugs could be purchased for cheap on the black market
—almost as cheap as a bottle of Advil.
And then he closed his laptop hard as his sensibilities returned to him—at
least for a short moment. His heart was pounding. For that short minute, he
was actually considering it. He was actually about to navigate over to the
Dark Net to buy himself some hormone replacement drugs, so he could have
his own breasts and a softer voice and softer skin and fuller hair…
It was almost 11:00 PM and he had none of his work done. So he got
started, one piece of clothing at a time. Whenever one piece of clothing had to
sit on the steamer for an extended period of time, he would use that time to
get changed into a new outfit. It was his eighth outfit of the night that pushed
him into his bedroom where his old steamer handle was waiting for him.
It was a black satin babydoll slip, dropped off near the end of the day by
one of his prostitute clients. It was soft and used and adorable, and it had a
little pair of crotchless panties built in. His cock hung out from that crotch
hole, and he was erect within minutes of putting the outfit on. This time, he
couldn’t stop himself from stroking his shaft—and he came faster than he’d
ever come before.
He finally got to sleep around 5:00 AM, just an hour before his alarm
went off. So he spent his Friday dozing off behind his desk. Thankfully, there
were never many clients on Fridays. And that Friday wasn’t special. Terry
ended up falling asleep behind his desk around 10:00 AM and he wasn’t
woken up until 2:00 PM, when one of his usual clients tapped him on the
shoulder and said, “I need these clothes cleaned. They’re brand new, so I
don’t want to run them through the machines.” It took Terry a moment to
come back to life. He shook his head and processed the client’s words, and
then he accepted her wardrobe bag.
“No problem,” he said.
She was a prostitute, like many of his usual clients, but she was one of the
high-end ones, the ones that call themselves escorts. As soon as she was gone
and Terry was awake again, he looked through her bag and his eyes lit up at
the sight of the beautiful white dress inside. And there was a pair of white
heels. Terry occasionally found shoes and jewellery in wardrobe bags, as
people tried to keep their outfits together.
Terry looked around to make sure the coast was clear, and then he brought
the shoes out from the bag and placed them on the ground. He tried to wriggle
his foot into the left shoe. It was tight but it fit. He looked around again and
then he stood up, bearing his weight on that heel. It wasn’t nearly as
uncomfortable as he was expecting, though maybe he would change his mind
after walking around for a few hours in the heels, which he was already
planning on doing around his apartment.
There were a few hours left in his day—a few hours before he could get
the pretty clothes home so he could have his fun. He had a few more clients
come in with more pretty clothes, but he didn’t make the same mistake as the
day before—he cleaned the clothes in the shop and stuck to the single bag he
planned on taking home. If he didn’t get his sleep, he knew he would do
something stupid, like accidentally send a picture of himself in pretty
women’s clothing to his mother.
It was during his final open hour that he noticed one of his clients out on
the street, starting her night of work. She was only on the street corner for five
minutes before a sleek black BMW pulled up and commissioned her for a job.
She hopped in the passenger seat and the car zipped away. Terry’s heart
stuttered as he imagined himself in her shoes—literally and metaphorically.
He couldn’t even imagine how frightening and exciting it would be to have
sex with a stranger, for money. He knew the girls who did it—they never
seemed afraid or worried. Maybe it wasn’t as scary as it looked. Maybe it was
actually fun. Terry enjoyed having sex—having sex for money actually
seemed like the perfect gig.
He closed his shop down and started his trek home. He walked quickly,
excited to get into the expensive and pretty wardrobe, which he also had to
clean and steam before going to sleep for the night—and sleep was important.
He couldn’t go another night without getting eight hours of sleep.
Terry was halfway home when he remembered it was Friday and he didn’t
have to open shop until noon the next day. He had tons of time to enjoy the
night—tons of time to enjoy the adorable outfits that were in that wardrobe
bag.
CHAPTER VII
Terry was having fun, trotting through his apartment in the heels, feeling
the soft satin against his skin. He was starting to get the little feminine
mannerisms down, and his voice was getting better with each passing night.
He would stand in front of the mirror and talk, sometimes for over an hour
while admiring himself, trying to figure out how he could be just a little bit
more convincing.
He found himself sitting closer and closer to that mirror, trying harder and
harder to figure out which of his facial features were obviously male. Even
his Adam’s apple didn’t seem apparent anymore. Had it ever been apparent?
And his shoulders seemed so narrow—but were they ever broad?
His voice wasn’t terribly convincing, but aside from that, he was sure he
could pass. But there was only one way to know for sure. He walked over to
his window and looked down at the street. Groups of men and women flocked
in every direction, going from bar to club to pub and back again. As Terry
looked down at the street, he saw a pretty woman wearing a short skirt. A
carful of men pulled up next to her and whistled. “Looking good, darling!”
one of the men yelled, and then the car zipped away as faces turned red all
around.
And Terry wondered what would happen if he went out on the street.
Would people recognize him? Would they be able to tell that he wasn’t really
a woman? Would he get catcalled like the pretty woman in the short skirt? He
looked over at the mirror to decide if he was truly convincing, and then he
caught himself smirking with dark red cheeks.
Maybe they wouldn’t buy him as a woman, but they certainly wouldn’t
recognize him—so what was the harm? What did he have to lose? If they did
buy him as a woman, and he did get catcalled and hit on, then he was only
missing out by hiding out in his apartment. How could he pass up on the
opportunity to show off a thousand dollar dress?
He reached for the handle of his front door, and then his heart began
pounding. Why was his heart pounding? No one was going to recognize him,
so why was he nervous? He took a deep breath and realized his heart was
pounding with excitement, not with fear. He couldn’t wait to be a woman out
in the real world, and not just in the safety of his own apartment.
He opened the door and stepped out with eyes closed shut. He was too
afraid to open them, too afraid to see his neighbours staring back at him,
wondering why he was wearing a woman’s dress and makeup and a wig. He
was relieved when he opened his eyes and saw nothing but closed doors. He
took a deep breath and started down the stairs, moving carefully as he’d never
navigated a staircase in heels before.
But he managed to make it to the bottom without falling. As he went to
open the door at the bottom of the staircase, one of his neighbours beat him to
it. “Sorry,” she said as she moved to the side. And then she looked Terry up
and down with a peculiar look that was foreign to Terry. All Terry was able to
do was force a smile. He knew he needed to brush by her and get out of there
before she had too much time to look at him, but he couldn’t move.
“Thanks,” Terry said in his feminine voice, finally breaking free from his
paralysis. He skirted past her and rushed towards the door.
“Wait,” she said, making Terry’s heart stop for a moment. He turned
around slowly, still with that painfully forced smile on his face. He was
regretting everything: leaving his apartment, putting on the dress, getting into
cross-dressing in the first place.
“Yeah?” Terry said softly, hoping his voice wasn’t giving him away
anymore than his look already had.
“I love that dress,” she said. And then she looked at Terry’s feet. “And
those shoes. Where did you get them?”
Terry squirmed. Was she teasing him or was she serious? Could she not
tell that he wasn’t actually a woman? “Saks,” Terry said with his soft,
feminine tone. “See you later.” He turned around and got out of that building
as quickly as he could. And he didn’t feel safe until he was three blocks away
from the building, three blocks away from the neighbours who saw him on a
regular basis.
And then he realized he was three blocks away from his home, away from
safety. He was now standing out on the street on a busy Friday night,
surrounded by people who could see him—people who lived in the city, who
probably walked by his shop all of the time. He’d never been so vulnerable in
his life. He’d never been so exposed in his life, with his short skirt hardly
even covering his perky bum. And what would he do if he sprung an erection?
He hadn’t masturbated before leaving the house, and the lace of his panties
were already beginning to arouse him—and so was the tight satin of the
expensive white dress. Hell, even the heels were strangely arousing.
But he had to keep his composure. He had to keep his cock from
hardening. He took a deep breath and looked around. Across the street was a
busy club. A group of men stood outside with cigarettes in their mouths. Two
of them were looking Terry’s way. One of them nudged another, and a
moment later, all of them were looking Terry’s way. One of them smiled and
waved. “The party’s over here, beautiful!” he called out.
Terry’s legs trembled. He smiled and waved back. “Thanks,” he softly
called out—probably not even loud enough for them to hear. They went back
to chatting, looking over every few seconds, probably trying to figure out why
there was a woman in a skimpy dress standing alone on a street corner… Or
did they think Terry was a prostitute? Did they think he was waiting for a job
to come by? Terry’s heart stuttered again.
And what was Terry waiting for? Where did he want to go? What was he
looking for? He spun around and tried to figure out if he’d lost his mind. And
then he saw Granville Street, teeming with people, buzzing from club to club.
He saw a bouncer letting a group of beautiful women skip a long line, and he
saw a group of young men hitting on a group of young women. Everyone was
having fun—and all of the women were sexy. Terry wanted to be like them.
He wanted to be hit on and drooled over and slapped on the ass. So he started
walking down Granville Street.
And he only made it a block before he turned a set of heads. “Where you
going, baby?” a brown-skinned man asked.
Terry shrugged his shoulders, unable to hide the red-cheeked smile from
his face. “Why do you want to know?” he asked.
“Is there room for a few more?” the man asked.
Terry just laughed and continued down the strip. He wasn’t headed
anywhere. He was just basking in the attention, and loving the feeling of the
cool air teasing up his legs and tickling his bare ass. As he stopped at a red
light, he got exactly what he left the house for: a carful of young men
whistling from their windows. “Show us your tits!” one of the men shouted.
And of course Terry didn’t flash the men because he had nothing to show
them, but he loved the attention. He loved that they singled him out and not
the other fifteen girls who were standing on the same block, waiting for a
little bit of attention of their own.
Terry’s head was spinning with excitement. He was having more fun than
he’d ever had as an adult. And that excitement was starting to scare him. A
week ago, the thought of walking down Granville Street in a short dress and
makeup would have made Terry shudder with nausea, but now he didn’t want
to go home. He wanted to hit up that strip every night. And he wanted to take
his new fun even further. He wanted to see just how much fun he could have
as a woman, in his clients’ pretty clothes.
But for tonight, he knew he needed to cut himself off. He needed to get
home, jerk off, and get to sleep so that he could wake up with a clear and
straight head. He needed his sensibilities back before he did something stupid,
before he marched himself in front of people he knew and cared for—people
he didn’t want to know that he was a closer cross-dresser, like his family and
his friends. So he made his way back home, basking in the final few minutes
of his female glory. One of the people who lived in his building held the door
for him—something he wasn’t used to, such a small gesture but so nice and
refreshing.
It only took a few minutes for Terry to get off that night: a few anal
penetrations and a few strokes of the cock, and cum was everywhere. He got
the little dress nicely cleaned and hung before heading off to sleep. And then
he dreamed about pretty clothes and stunning eye makeup.
CHAPTER VIII
It was an unfortunate Saturday when the only clients who came into the
store were there to pick up their orders. No new orders, no new pretty clothes
being dropped off. Terry had nothing to work with, nothing for his Saturday
night, which he’d spent all morning looking forward to.
It was 4:00 PM when his shop was supposed to close, but Terry didn’t
close, hoping some beautiful woman would come in looking for some last
second dry-cleaning. All of the other dry-cleaners closed at 4:00 PM on
Saturdays, so maybe being the only one open would bring clients in… But no
one came. Terry was stuck with nothing on the most exciting night of the
week.
So he went into the back of his shop and started searching for anything.
There were a few sacs that had been sitting in the back corner of the shop that
he’d been meaning to take to a donation bin—sacs of clothes that were
dropped off and then never picked up again. It happened from time to time,
usually with older people who either forgot about their clothes or, God forbid,
passed away. But occasionally there were clients who didn’t come for their
clothes for other reasons: because they couldn’t afford the bill or because they
decided they didn’t want them anymore.
Most of the sacs at the back of the shop were filled with old ladies’
cardigans and old men’s suits—but there was one bag that had more along the
lines of what Terry was looking for: dresses. They were all matching
bridesmaids dresses, all blue, all different sizes. There was one in the bag that
was perfectly Terry’s size. He tried it on there in the back of the shop.
It wasn’t the most flattering dress, so Terry used a pair of scissors to cut
the cheesy flower decoration off of the shoulder, and that helped. Then he
brought the dress into his little alterations corner to make it a bit shorter, and
to make the straps a bit thinner. It took him a good hour and a half, but the
work was worth it. The dress suddenly didn’t look so ‘prommy’. Now it
looked more like something a girl would wear out at the clubs—or what Terry
was going to wear out at the clubs.
But the outfit wasn’t complete. Terry didn’t have panties, he didn’t have a
bra, he didn’t have shoes, and he couldn’t wear his wig and baseball cap
combination again, as it didn’t exactly compliment a nice dress. So Terry
made a few stops on his way home from work.
His first stop was at a woman’s shoe store. He was embarrassed walking
in, and even more embarrassed when the store clerk asked him what size his
wife’s feet were. “About the same as mine, actually,” he said. And then he
watched the clerk’s lips curl into a smile—she knew the shoes were for him.
So his face was dark red as he tried on shoes until he found a nice pair that fit.
They were about one hundred bucks.
Next was the costume shop, which was a few blocks out of Terry’s way.
They had a whole section of wigs, which was essentially reserved for drag
queens when it wasn’t Halloween—and it wasn’t Halloween. Terry had no
fake story for the store clerk at the costume shop. He thought about lying
about a wife with cancer who needed a wig, but he knew that would be a
stretch, especially when the clerk asked for his wife’s head size and Terry
would have to say, ‘About the same as mine.’ It was better to not lie about a
terrible disease.
So he said nothing. He just went to that wall and awkwardly asked the
clerk to take down the long brunette wig that closely matched his own natural
hair colour. The clerk asked no questions before taking the wig down and
fitting it on Terry’s head. “I think we need something a bit tighter,” said the
clerk before disappearing into the back room. Terry’s face was dark red as he
left the store, but at least he was leaving with a high quality wig that would
last him years.
Terry’s final stop on his way home from work was at the lingerie store. He
went in to get a single pair of panties and a bra, and he ended up leaving with
five pairs of panties, two bras, two slips, a lace bodysuit, and a garter belt
with a pair of fishnet stockings. It was a hefty bill, but Terry just couldn’t help
himself. He didn’t even bother lying to the store clerk at the lingerie store. He
just said nothing as he collected his items and paid the bill. At the counter he
noticed a little bottle of perfume, so he bought that as well.
He had a quick bite to eat at home before running a bath so he could
freshly shave his legs and armpits. Then he quickly got himself dolled up,
slipping into a pair of red panties and a matching red bra. He admired himself
in the mirror for a few minutes. It was amazing how feminine he already
looked, just wearing some women’s undies. He didn’t even have his wig or
makeup on yet. It was hard to believe he’d never noticed his feminine figure
before. Had he always had it? Well it didn’t just come out of nowhere…
Terry got to thinking: maybe all guys are born with a potentially sexy
physique. Maybe being feminine is more about the pretty clothes than the
body a person is born with.
Next, Terry did his makeup. He took his time. It was still early in the
night, and he wanted everything to be perfect. He went with that same look:
the smoky cat eye look, with a few minor alterations that he’d learned about
while doing some research on his phone at work. Next came his blue dress,
which he’d altered a little bit too short. The bottom cusp of his ass was
hanging down, but he didn’t mind. He knew guys would like it.
Finally, he got into his new heels and his wig. And then, once again, he
found himself in front of the mirror, staring at himself, admiring his curves
and his stunning features. He was sexy. He felt comfortable—like himself, as
if for the first time in his life. He was ready to show himself off, ready to go
out for the night, ready to try new things and feel that amazing excitement one
more time.
CHAPTER IX
The clubs were intimidating. The line-ups were long and the women
lingering around them were beautiful. And the men weren’t bad either—all
jacked and handsome and constantly scanning their options. Terry knew he
was making himself vulnerable by walking up to the front of that line to try
his luck with the bouncer. He’d watched a few girls pull it off, getting let
inside, skipping the line—but he’d also watched a few girls get rejected,
being told to go to the back of the line. One girl ran away as soon as the
bouncer told her, “No way. Back of the line.”
But Terry had to try. The thought of trying brought on that excitement that
Terry had become so obsessed with. He needed that rush and he wasn’t going
to get it unless he paraded himself in front of all those people. When the
bouncer turned to look at him, his joints froze. He nearly stopped in his tracks
and fell over like a stiff board. But he forced himself to carry on, and he
forced himself to smile.
“Hi,” he said with his soft, meek voice.
“Can I help you?” the bouncer asked with a stone cold tone.
Terry cleared his throat and held his composure. “One of my friends is
inside,” he said, and then he forced that smile bigger. The bouncer kept
staring at him with that cold gaze. And then suddenly, he moved to the side
and let Terry in.
Terry’s heart leapt up in his chest, pounding hard against his ribcage. He
was let in, he was accepted as a beautiful woman! But was it a good thing?
Was it good that society was accepting his delusion? Was it good that the
world was allowing him to get away with this degenerate addiction?
A man bumped into him. “Sorry, sweetie,” the man said. And then he
froze as he looked into Terry’s eyes. Terry’s heart stuttered, which he was
getting used to. “Can I buy you a drink?” the man asked with glowing eyes.
Terry just smiled, and a minute later there was a drink in his hand. He
drank it happily. He’d never been given a free drink before—but it wasn’t the
last one he would get that night. It was only twenty minutes later when
another drink ended up in his hand, but he had no idea where this one came
from. He still drank it, not wanting to waste it. And then another drink came,
and another, and another.
And soon, Terry was heavily buzzed, wobbling slightly in his heels,
worried he was about to topple over or let his natural male voice slip out. He
knew he needed to get out of that club and away from all of the attention for
just a short period of time, so he could get a hold over himself.
He stumbled out from the club’s back door and he took a deep breath of
fresh air in that cold, dark alleyway. His head was spinning, and not just from
the liquor and the flashing lights. He walked down a short ways before
coming across a window with a board behind it. He used the window to look
at his own reflection, still in awe of how feminine he looked. It still didn’t
seem real—it all still seemed like a strange dream that wouldn’t end, that he
didn’t want to end.
He reached the end of the alley and looked down the road. His heart
stopped momentarily as his gaze met the gaze of one of his clients: Sheila, the
prostitute and owner of the purple lace lingerie. She was wearing it now as
she stood on the street corner, wearing only a fur coat over it.
Terry had to remind himself that he was unrecognizable, especially from
half a block away. Now he just looked like another woman enjoying her
Saturday night downtown. He didn’t look like Terry, he didn’t look like
Sheila’s dry-cleaner. She smiled and then turned back to the street, waving at
passing cars. And she had the power to make every car slow down as men and
women alike stopped to admire her body. Terry was sure that many of those
men were considering her: thinking about cheating on their wives with the
beautiful escort.
Terry started to casually walk in Sheila’s direction, drifting wide and out
of her line of sight. He kept an eye on her, and then he noticed a few other
prostitutes down the block, all waiting for jobs of their own. Terry backed
himself against a wall near a bus stop, pretending to wait for a bus so that he
could watch the night workers. He was only there for a few minutes, and in
that time he watched as Sheila got picked up, as well as a few of her coworkers,
if you can call them that.
The cars picking them up weren’t crappy old Buicks. The girls were being
picked up by shiny new BMWs and the odd Lexus. These guys were probably
paying these girls a lot of money for a night of fun—or even just an hour or
two.
Terry wandered further down the street, venturing deeper into
Vancouver’s nightlife. As he came closer to Davie Street, where all of the
homosexuals hung out, he came upon a new block of prostitutes. But these
girls were different—they were taller, some were broader, and a few had a bit
of five o’clock shadow that their makeup couldn’t hide. These prostitutes
were men—some made more convincing women than others. The sleek
BMWs picked up the convincing girls and the rest got their turns in beater
trucks and old VWs. But there was a market for all of them.
“Hey!” a male voice called out from behind Terry, making him jump and
spin around. A man was staring at him, hanging out the window of a black
Audi. He was wearing a suit and an expensive golden watch, which dangling
down over his window frame. “How much?” the man asked. And it took
Terry a moment to realize the man was talking to him.
Terry cleared his throat. “How much?” he asked awkwardly.
“Yeah, that’s what I asked—how much for two hours?” The man wasn’t
bad looking—he was a bit older with some grey hairs. He was thin and he
seemed to be nicely groomed.
Terry wanted to tell the guy to beat it, but he was suddenly overwhelmed
by a curiosity—and Terry didn’t have the best track record when it came to
fending off teasing curiosities.
CHAPTER X
The man’s apartment was impressive, on the top floor of one of the bigger
buildings in the downtown core. Some of his walls were painted a deep red
colour, the others were painted black, and there were quirky lamps
everywhere. But nothing looked cheap. Even the hat rack by the front door
looked like it had real gold embellishments on it.
Terry wasn’t sure how his legs were still allowing him to walk. His heels
were starting to hurt, and the terrified trembling hadn’t gone away since he
told the man, “Five hundred dollars,” back on the street corner. When he said
it, he didn’t expect the man to agree so quickly. “Hop in,” he said without
missing a beat.
But Terry didn’t get in right away. He was way out of his element, about
to break through more boundaries than he was ready for: getting fucked by a
stranger, getting fucked by a man, getting fucked for money—the list went on
and on. But Terry couldn’t say no. For days, this had been his secret little
fantasy—the exact scenario that played out in his mind whenever he pressed
that black steamer handle into his asshole.
But now, his heart was stammering. He’d never been with a man before.
He’d never even been attracted to men before, but now, for some reason, this
particular man seemed irresistible, even though he wasn’t anything special.
He was just rich and horny; Terry only cared for the latter. But he was
terrified. Sure, before he got into the car he made sure to say, “I’m not really a
woman you know.” He was surprised when the man laughed and said, “I
figured, though you look stunning.” So now, Terry knew he didn’t have to
worry about letting his masculine identity slip. He didn’t have to worry about
dropping his feminine voice for a moment, or accidentally exposing the bulge
in his little red panties. His client knew exactly what he was in for, and Terry
was exactly what he wanted.
Terry was only a few steps into the room when the man walked behind
him and put his hands on Terry’s shoulders. “I love your dress,” he said
before slipping his hands gently down the sides of Terry’s recycled blue dress.
“Thanks,” Terry said softly. His body was tense. He was being touched by
another man, a man who intended to stick his cock in Terry’s ass, a man who
didn’t even have a name as far as Terry was aware.
The man wasn’t shy. Terry probably wasn’t his first prostitute experience.
It was only a minute before the man tried to reach down between Terry’s legs.
Terry, acting entirely on impulse, reached down and grabbed the man’s hands,
holding them around his pelvis, terrified to let them go any further, even
though it was exactly what the man was paying for. Terry didn’t like being
reminded that he had a cock between his legs. He wanted to feel like a
woman, and he felt like a woman when the man was kissing his neck and
rubbing his erect bulge against Terry’s ass.
But Terry especially liked it when the man reached around and cupped
Terry’s padded chest. He liked it when the man squeezed, eliciting a soft
moan from Terry’s lips. “Your heart is beating so fast,” the man said with the
palm of his hand against the centre of Terry’s ribcage.
“I’m sorry,” Terry said, though he wasn’t sure why he said it. The man
laughed and went right back to kissing Terry’s neck, teasing his fingertips
down Terry’s body towards Terry’s cock. Terry had the urge to stop him
again, but he resisted. The man was much bigger than Terry, and much
stronger. He didn’t want to make him angry. If the man snapped, he could
easily kill Terry and get away with it.
Those fingers drifted over Terry’s pelvis, over his pubic bone, and down
across his bulge. They teased up Terry’s skirt and then found themselves on
his panties, massaging his cock as if it was a clit. The man rubbed his fingers
in small circles, making Terry feel even more like a woman—and more like a
slut. Terry let a long, soft moan slip out from his lips.
“You like that?” the man asked.
Terry nodded his head. His long brunette hair fell in front of his face as he
looked down at the stranger’s hand under his skirt. “Shit,” he muttered. He
liked it—he liked it too much. He couldn’t wait to get the man’s cock into his
asshole. And he couldn’t wait to do this again and again. Who knew that
being a prostitute could be so much fun? And for five-hundred bucks? That
was more money than Terry made in a week, most weeks.
Terry was getting hard fast, but his little red panties did a surprisingly
good job of holding him down. The man made sure to locate the tip of Terry’s
cock as he continued to rub. Terry squirmed in his tall heels. And then he
found himself reaching back, running his fingers down his client’s abdomen.
He fought his fingers down his client’s pants and then located his cock. He
was already hard—and he was big, much bigger than Terry, and much bigger
than the black steamer handle that Terry had been using each night.
The man’s cock was warm—hot even. It was throbbing, and Terry could
feel all of his veins. He only stroked the man a few times before he could feel
a dab of warm moisture on the man’s tip: a small bout of pre-cum. The man
probably wasn’t going to last long once inside of Terry’s asshole—assuming
he could even fit inside of Terry’s asshole. It seemed unlikely now, as Terry
could hardly even wrap his fingers around the man’s girth. But the man paid
his money, and Terry was itching to get off as well.
The next few minutes were a blur. The man got Terry’s cock out from his
panties, and then somehow Terry ended up on his knees, turned towards the
man. That giant cock dangled in Terry’s face, making Terry’s heart stutter and
his hands tremble. But still, he reached up and grabbed it and stroked it and
felt it throbbing. He brought it to his lips and his heart stuttered again. He was
only able to fit half of it in his mouth before that tip was pressed against the
back of his throat. He gagged a bit, but managed to hold his dinner back—
even when the man grabbed Terry’s head and pulled it in tight to his pelvis.
“You like that, you little slut?” the man asked through clenched teeth. His face
was starting to turn red and his cock was throbbing even harder. He really
wasn’t going to last very long.
Terry was only able to respond by nodding his head slightly. He could
taste the drooling tip of the man’s cock, pre-cum oozing out onto his tongue.
It was sweet, and a bit salty, but Terry didn’t mind it. He kind of liked it. He
liked that he was able to make a man so hard.
“Get on the bed,” the man said, pulling himself back quickly, as if he was
stopping himself from ejaculating prematurely.
Terry stood up and realized his legs were trembling harder than ever
before. He looked down and saw that his cock was rock hard, holding up the
skirt of his dress like a tent pole. And then he looked at the large bed with its
black satin sheets, and he wondered: what the hell am I doing?
What happened? How had Terry degenerated so much in the span of a
single week?
He looked over and saw his reflection in the mirror, and he suddenly
remembered the woman who dropped the blue dresses off, two months
before. He remembered her face when he told her how much it would cost to
dry-clean all ten of the bridesmaids dresses, and he remembered her saying,
“They didn’t even cost that much to buy.” He had a feeling she wasn’t going
to be back for the dresses, or to pay the bill, so he only quickly ran them
through the steamer.
And when he looked at the blue dresses back then, the only thought that
ran though his mind was: are there any stains on them? And that was better—
that’s how his mind should have stayed wired. Life was easy and simple back
then. He knew his job and he performed his job and he didn’t get mixed up in
stealing clients’ clothes or breaking the law by becoming a transgendered
prostitute. Why couldn’t life be that simple again? How could Terry stop his
degeneracy—or was it too late?
“I said, get on the bed,” the man said to Terry. He was standing naked,
with his cock throbbing and nearly touching his sternum. That erection was
intended for Terry’s asshole. And if Terry let it in, there may be no turning
back. How could he turn back after losing his anal virginity? What else would
he have to lose at that point? As long as Terry had something to lose, he still
had his pride and his sanity. But if he let it all go, then there were no limits to
his new illness.
CHAPTER XI
Terry’s whole body was trembling as he lay himself down on that bed, on
his stomach. He tried to take a deep breath in as his client climbed on top of
him and bent over to rub Terry’s back. Terry could feel the man’s hard cock
throbbing on his ass, warm and large, taking a short break after nearly being
stimulated to orgasm by Terry’s soft lips.
Terry closed his eyes and tried to stop his head from spinning. He didn’t
care about the five hundred dollars. He wasn’t doing it for the money—and
that’s what scared him more than anything. He was just doing this for the
excitement. Had the man pulled up and said, ‘I’ve got no money but I want to
fuck you anyway,” Terry would have probably still gotten into the car.
He could hear the man slipping a rubber onto his cock. He was surprised
they made rubbers that big. Then he heard the squirting of lubricant as the
man got his long hard cock ready. Terry tried again to take a deep breath, and
this time he got a bit of air into his trembling lungs.
Terry found himself thinking about his friends and family members—
wondering what they would think if they knew what Terry had been doing
over the past week, wondering what they would think if they could see him
now, all dolled up and about to take a cock in the ass. And to think, this all
started because of a moment of drunken shenanigans. Was this degeneracy
always lying dormant? Did everyone have this in them, or was Terry just a
special degenerate?
Terry felt the man pulling his panties aside a moment before the tip of his
warm, lubricated penis pressed against his puckering hole. It felt impossibly
enormous, yet Terry just remained still, allowing the man to carry on. What if
his penis was so big it ripped Terry apart? What if it permanently stretched
him out and he had to wear diapers for the rest of his life? What if it hurt so
bad that Terry left that apartment with PTSD? Why wasn’t Terry stopping the
man?
He started pressing that hard cock in. The pressure was intense as he tried
to get that initial penetration. Terry bit down on a pillow as that tip finally
pressed through, rattling his ass. “Oh God,” Terry moaned. His fingertips dug
into the sheets and his legs squirmed—but the man had him pinned, and the
man wasn’t stopping. He sunk his cock in deeper—just another inch deeper,
but it was enough to make Terry tense up and squirm even more.
“Do you like it, slut?” the man asked.
“Yeah,” Terry said, and he was shocked to hear the word leave his tongue.
The man sunk another inch deeper, making Terry even tenser, making him
moan louder. There was a real cock in his ass: the cock of a stranger—a cock
that could have been in many assholes before Terry’s. He could feel it
throbbing. He could feel the man’s veins pumping blood.
“Please be gentle,” Terry managed to say. But the man only replied with a
chuckle. That cock sunk deeper. It was now deeper than that black steamer
handle had ever gone. It was deeper than the steamer handle could go. And
the man still had a few inches left to play with. He sunk in a bit deeper.
Jolts of warm energy were pulsing through Terry’s body. His hands were
twitching and his eyes were flashing. He moaned and squirmed and then he
started to feel it: the euphoria. The man had found his sweet spot, and his
giant cock was pressing hard into it. A bit of drool formed on the corner of
Terry’s lips. He fought back the urge to moan and let the man know that he
was suddenly enjoying the stuffing.
The man sunk in deeper with a final shove, pressing his pelvis into Terry’s
ass. Terry could feel the tip of the man’s cock pressing up to his sternum. He
could feel every throbbing inch of the impressive member inside of his body.
He turned his head in an attempt to fight away the urge to moan, and that’s
when he saw the mirror: his own reflection staring back at him.
And Terry realized he wasn’t submitting to degeneracy. Dressing up in
pretty clothes wasn’t just some sick addiction, or some mental illness. He
looked good as a girl. His face was stunning with a bit of makeup, and that
skimpy blue dress gave him curves worth of a magazine cover. He hadn’t
discovered some dark secret about himself when he first tried on those clothes
—he discovered something amazing about himself. He discovered that he had
a woman inside of him. He discovered that he was happy wearing pretty
clothes and cute makeup.
Now, he was happy that he put on those clothes as a joke a week before. If
he hadn’t, he wouldn’t have had one of the most fun weeks of his life. He
would be in that apartment now, making five hundred dollars for having a ton
of fun and getting off. He wouldn’t have experienced being catcalled on the
street, and he wouldn’t have gotten free drinks at the club. He had so much
left to experience as a woman—and this rich stranger was just a small part of
that amazing experience.
So Terry let his body relaxed. He continued watching his reflection as the
man started to thrust in and out. He watched as that long cock rose up and
disappeared, over and over, sinking deep inside of him. He watched as his
long beautiful hair bounced, and he watched as his big eyes glowed. He was
watching himself, in his element, with a big warm smile on his face—on her
face. She wasn’t a man in those clothes. She wasn’t a man with that makeup
and that wig. And in his heart he wasn’t a man either.
The client grabbed her hips firmly and pounded his cock down with force.
His pelvis slammed her butt, making it ripple, making jolts of warm euphoria
burst through her whole body. She didn’t want the moment to end. She
wanted that big cock inside of her all night long. And maybe she would offer
the man a discount for a second fucking in just an hour or so…
“You’re so fucking tight,” the man groaned through clenched teeth. His
hair was ruffled on his face, and beads of sweat were running down to his
chin. “And fuck, I’m so hard. It feels so good.” Terry liked it—she liked
making the man happy, even though she didn’t know who the man was. She
liked that she was sexy enough to make a man so hard. And she didn’t blame
the man. Looking in the mirror, she was arousing herself.
She groaned and squirmed and then felt a warmth pooling around her
cock. “Oh God,” she moaned. “I’m coming. You’re making me come.” The
man shoved his hand down, underneath Terry’s cock. He cupped the tip of her
cock and grabbed a few blasts of her amazing cumshot. Then he brought that
hand to her lips and made her lick it up, which she did without hesitation. He
wiped some of that cum on her cheek and then he grabbed her hips again so
he could drive his cock in harder.
And he didn’t last much longer. After just a few more pumps, he was
filling that condom with his hot load. He groaned and held her tight until he
was depleted, and then he fell back onto the bed. Terry stayed in place,
catching her own breath, even though she hadn’t done anything but lay in
place. Her asshole was a bit sore but the euphoria was still teeming through
her body.
The man paid another two hundred to have her stick around for another
hour. It was only twenty minutes later when his cock was back in her ass,
pumping her to another orgasm. When Terry finally returned to her apartment
that night, she found herself staring at the seven hundred dollars for a minute
before turning her gaze to the mirror. Even after everything, she still couldn’t
get over how beautiful she was—and how beautiful she would be from now
on.
She didn’t work on Sundays, so she spent the whole next day at the mall,
buying a new wardrobe with the money from her paid romp. She didn’t plan
on pursuing the life of a prostitute—that was just for fun, just for the
experience. But she did plan on pursuing a new life as a woman.
She knew there would be some embarrassing moments, especially at first.
She knew there would be some weird looks from the usual clients who knew
Terry—and not to mention friends and family members. But she knew that the
awkward phase was just that: a phase.
When she woke up that Monday morning, ready for the busiest day of the
week, she knew that the hardest part of the day was going to be leaving her
apartment, allowing her neighbours to see her in a dress and a pair of heels.
She knew that it would be awkward when the first usual client came into the
store, but she knew it would only get easier with each passing minute, with
each passing hour, and with each passing day. She was ready—because
sometimes it takes a bit of being uncomfortable to be able to truly appreciate
the good things in life.
THE END
ABOUT THE AUTHOR
NIKKI CRESCENT
Nikki Crescent is a young writer from the golden prairies of Alberta,
Canada. She spent her schooling years lost in her own imagination, writing
everything from articles, screenplays, comic books, and short stories.
Obsessed with the idea of love, fascinated with sex and captivated with the art
of writing, Nikki decided to become a writer of erotic romance. Nikki
Crescent is a top-selling writer of romantic and erotic fiction with over sixty
titles across many sub-genres. Her fiction work has found her on Amazon’s
best-selling charts many times over
English
Russian