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Crossdressing

Our crossdressing (cross-dressing) stories feature tales of either gender (usually male) dressing up in the clothes of the opposite sex, for reasons of sexual gratification. Crossdressers are akin to the transvestic fetishism, which is a sexual fetish for the clothing of the opposite gender. The crossdresser can be of any sexual orientation.

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Barrack Room Betty - Chapter Fourteen

Michele meets a Bangkok ladyboy and they strike up more than just a friendship

Chapter Fourteen – Supergirls Bangkok “I’ve fucking had it with Jason!” Michele spat at Rod Latham “That fuckwit tracked me down and found me in a bar in Naples and created an absolute shitfight. And every night I’m here in the club, he carries on like a petulant child whenever I work a punter and in particular Lieutenant Steve Winters who is one of our best customers. When is...Read On

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Barrack Room Betty - Chapter Thirteen

Transvestite Wrens visit Naples and have fun in the sun.

Chapter Thirteen – Naples – Whores and Princesses The Ark continued her voyage through the Mediterranean Sea, exercising with the Task Group as she went and arrived in Naples a week after she left Gibraltar. Lieutenant Steven Winters, RN, became a regular at Barrack Room Betty’s whenever there was no night flying. He entered into an arrangement with Michele that she would always be...Read On

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Barrack Room Betty - Chapter Twelve

Crossdressing sailors operate a brothel on a navy ship

Chapter Twelve – Pleasuring an Old Friend Ark Royal sailed for her deployment in a small Task Group of three ships and on the first night Barrack Room Betty’s opened for business and was an instant success. At first, the main earner was gambling and booze but as the ship got further away from her home port the temptation for the punters to ‘tap’ the attractive transvestite hostesses...Read On

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Barrack Room Betty - Chapter Eleven

The Bettys reunite on board the Navy's flagship where Michele turns adversity to her advantage

Chapter Eleven – An Offer You Can’t Refuse! Michele remained on her knees and waited for Chief Writer Rod Latham to come over to the bunk to see what he wanted of her. It turned out he wanted a quick fellatio session, which she provided. After the three sailors had satisfied their urges with Michele, it was time to talk business. “So as you can see, compartment Six Quebec Delta Alpha...Read On

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Kandie And The Dildo Challenge

His dildo collection was amazing!

Finding the right lover on Craigslist can be a time-consuming process, but every once in a while you find that perfect lover who takes you to exactly where you need to be. It was a Wednesday morning. I took the day off to get things done around the house, run errands and then relax. The day began with a cup of black coffee and my laptop. Let's check the Casual Encounters on Craigslist just...Read On

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Barrack Room Betty - Chapter Ten

The Betty's go to sea in the Navy but doesn't stop their crossdressing antics

Chapter Ten – Sea Daddies and Sea Mommies Seaman Michael Nyland graduated from Recruit School in March 1974 and was immediately posted to HMS Raleigh to commence training as a Writer; a sailor specialising in pay, personnel matters and administration. He was glad to see the back of HMS Chelmsford; Spike and the three other Leading Recruits had passed out at the end of January and had...Read On

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Barrack Room Betty - Chapter Nine

The ROP is over at HMS Chelmsford and the 'Bettys' go out for a night on the town for the first time

Chapter Nine – Pink Pussycats All good things come to an end and the six-week Reduced Operations Period at HMS Chelmsford ended on 15th January 1974. The Wrens and Leading Recruits were very busy as that day approached. The Depot needed to be de-winterised and preparations made for the return of the Ship’s Company, the other Recruits, and the Wrens from their leave. Even Petty Officer...Read On

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A Close Encounter Part 3

The perfect ending to an awesome night!

Homeward Bound   "Well, how was it for you?" My question was directed at my wife's reflection in the rearview mirror. She looked quite fresh considering that she'd just been fucked.   "Yeh, it was good! Pass me a tissue, babe." Sam stretched an arm between the front seats.   "It was certainly different!" Paul's assessment of the last hour's shenanigans raised a chortle.   "Not 'aff!"...Read On

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Barrack Room Betty - Chapter Eight

Four sailors and four pretty trannies locked up over Christmas, what are they going to do but party?

Chapter Eight – The Christmas Party Lieutenant Steven Winters was an extremely good-looking Navy fighter pilot whose last posting had been aboard the aircraft carrier HMS Ark Royal. There was some unpleasantness when, after a wardroom ladies dine-in night on board the ship, the rather portly Executive Officer had opened the door to a hangar workshop and found his glamorous wife bent over...Read On

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Barrack Room Betty - Chapter Seven

Michele sacrifices her ass to keep a secret.

And so Michele’s ordeal began. Every day at 1030, Michele and Jason left the administration building to conduct rounds of the Establishment, each going their separate ways. But Michele snuck back in the building as soon as Jason was out of sight. She would go to the ladies heads and dig around in her handbag and pull out her makeup, lingerie and heels. She applied heavy makeup and lots...Read On

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A Close Encounter Part 2

Not so much bi-curious anymore.

The dim ambient lighting inside the Coach House Inn gave the lounge a golden hue that was ideally suited for a guy masquerading as a gal. I couldn't have wished for a better location for Judy to come out to play. My wish list, however, would not have included the guy breathing into my left ear. "Perfume?" I croaked, continuing with the 'sore throat' ruse. I began to feign a cough in order...Read On

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Barrack Room Betty - Chapter Six

Michele offers herself to Petty Officer White so that the other Wrens don't have to service him

Chapter Six – A Turn For The Worse And so the Wrens and Leading Recruits settled into a routine. They knew that if they just spent their days jollying, drinking, having sex, and carousing that HMS Chelmsford would soon deteriorate into a shitfight, so they agreed to apply some discipline and stick to strict routines. The Royal Navy has run on routines from time immemorial; the day...Read On

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Bobbie Is In Denial

A femme boy's soak in the hot tub gets hotter than expected.

I woke up the next morning naked with Amy spooning me. She was fully clothed, even had her high heels still on. My mouth was dry and my ass was sore. I felt like a rag that had been rung out. What happened? Then I remembered kneeling in front of Joe, my ass hanging out like a juicy ham, practically panting and drooling over his thinly clothed cock. My sore little cocklet, which for some...Read On

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Barrack Room Betty - Chapter Five

Transvestite Wrens seduce their sailor tormentors and experience sex as a woman for the first time

Chapter Five – Boys Will Be Girls The three Wrens and three Leading Recruits were sitting engrossed in the movie. Michele rested her head on Jason’s shoulder and they were still holding hands. Jean was reaching into Mary’s popcorn bucket every few minutes, chewing popcorn around swigs of beer; he was enchanted by her perfume and found her very attractive but he had no idea how to woo...Read On

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The Shopping Spree

A shopping trip turns into an altogether different kind of trip

After a morning of shopping, I went for a hamburger. As I sat there with my bag of goodies by my side, a man in his early thirties sat down at the table next to me. He beamed a smile at me and said hello. It was unusual for people in the city to be friendly to strangers, but then again, he didn’t look like a man from the city. He must have been in his mid-thirties. His face was rugged, and...Read On

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Barrack Room Betty - Chapter Four

The leading recruits get friendly with the crossdressed Wrens

Chapter Four – A Night at the Flicks Michele was confused; she didn’t like Leading Recruit Jason Jones one bit, he was a bully but he was also handsome, strong and actually quite intelligent. She knew he had a thing for her as soon as the Leading Recruits made the grommets crossdress, and of course last night he had ejaculated in his pants when he was spanking her. Michele was no...Read On

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Barrack Room Betty - Chapter Three

The Barrack Room Bettys are starting enjoying dressing as Wrens; the boys like them dressed that way

Chapter Three – Michele’s Story The four Wrens of Collins Division woke at ‘call the hands’ at 0640. Doris had got out of bed at 0600 to prepare breakfast and was in the galley. She’d tried her best to do her makeup and dress like a Wren but she still looked like a ‘scranbag’; not that it mattered, in the steam filled, greasy kitchen. Her hair was matted and her makeup ran as she...Read On

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Barrack Room Betty - Chapter Two

Michele ensures the three transvestite WRENS meet the approval of their captors

Chapter Two – Wren Division Ho! The four Leading Recruits were hungover and hungry and in the grey dawn and cold bleak light of day they weren’t sure that their prank was really worth it. They entered the cabin and found the four ‘Wrens’ stood at attention and immediately began to break down in laughter. “Of my fucking god you guys look stupid!” Jean Burgess burst out laughing. ...Read On

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Femme Boy Gets Cock Drunk

My mind goes soft thinking about my bully's cock.

I’m not a very masculine guy. In fact, I’m downright girly. I blame my body. I’m 5’3” and weigh 110lbs, but the first thing people notice is my fat ass. It’s fat, tight, and juicy. It’s the kind of ass that women these days pay a queen’s ransom for. It flares out with my wide hips from a narrow waist and flat stomach and is complemented by proportionally thick thighs. My calves are...Read On

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The Motel And Black Lingerie

Being a lingerie showgirl in the motel

I had been on the road most of the day, having travelled almost six hundred kilometers in an effort to visit some of my most important clients. So, it was a relief when I arrived at the motel and was able to check in and get into my room. After checking my e-mails, I decided to head to the bar for a relaxing drink before contemplating what to choose from the restaurant menu. The bar was...Read On

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Where Did My Damn Key Go?! Part 3

When buying a cock cage, make sure you know where your key is (part 3).

Four days; I've dealt with four grueling days of not being able to touch myself. Jesus, how can anyone even do this without even going insane?! Ever since I crossed paths with that dominating bimbo, my entire routine had changed. And to be honest, I was surprised at how much sex was in my life. From the moment I woke up to the second I crashed and fell asleep, my mind was very frequently in...Read On

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Barrack Room Betty - Chapter One

Royal Navy recruits forced to crossdress - A prank with consequences.

Barrack Room Betty Ch. 01 By Michele Nylons©   Chapter One - Wish I Was Wren "Wish I was a Wren," Recruit Brian Perkins mumbled under his breath. 'Fuck! I wish he hadn't said that!' thought Recruit Michael Nyland. He knew that no good would come of it. "Your wish might come true," Leading Recruit Jason Jones (Spike to his friends) sneered. Michael Nyland shivered, and not...Read On

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Evening In The Office

Caught crossdressing in the office, but with a happy ending

The normal workday had finished and I gladly filed away the tedious paperwork that I had been toiling with over the past few hours. Knowing that I wasn’t going to depart for a number of hours, I went to the common tea room and made myself a cup of coffee. Back in my office, I sat back, sipped my coffee and contemplated my plan for the next hour and a half before the evening students started...Read On

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Recommended Read

To the Rescue

Norm is about to fulfill a fantasy and find out just how convincing he is as Natalie.

The music was loud.  The bar was crowded.  Norm had a good buzz going, and hadn’t paid for a single drink all night.  Actually, Natalie hadn’t paid for a drink all night, because that was the name he used – when he felt like offering it – on these little jaunts. He knew he looked good as a woman.  Heads turned and men approached him relentlessly every time he dressed to kill and hit...Read On

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Hostess With The Mostest - Chapter Three

Wannabe Airline Hostess TV Candi needs forged documents and blows the forger to pay for them.

Chapter Three – Passports and Payments   "How the fuck I am going to get my passport and references changed from Christopher Nyland to Candace Pops?" Candi sobbed into the phone. Michelle sat up in bed patiently listening to Candi whine on the other end of the line. Her lover was getting impatient and was rubbing his erect penis against her silk stocking-clad leg. She covered...Read On

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Hostess With The Mostest - Chapter Two

Chris becomes Candi so that he can attend the Flight Attendant training academy

Candi awoke late the next day with the sun streaming in through the window. For a few seconds, she thought she had dreamt the whole thing. Then she noticed her pillow was stained with lipstick, mascara, and eyeshadow and she smiled. She could still taste Michelle's sweet mouth on hers. She rolled over and tried to catch more sleep but her mind was racing. She had so much to do! First thing...Read On

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Happy to be Used, (Pt. 9)

I fill in for a shift at the bookstore and excel at customer service.

The next day I woke up very early.  I would have expected to sleep in since I got home after 2:00 a.m. but the clock said 6:00 a.m. when I opened my eyes.  I lay in bed reliving the events and my performance from the previous night.  The sex was amazing.  The double penetration was mind blowing.  But what really kept me smiling was my convincing female performance. No one suggested I was...Read On

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Second Place Winner

For Cari it's all about winning in the long run!

I’ve been dressing up as a girl in dresses and going out in public for the past two years since entering college. My goal has always been to be as pretty and as believably female as possible, when I choose to dress up as a female. I am blessed with being short and slim with facial features that can make me very realistic in make-up. Blonde hair extensions, false eyelashes, and glue on...Read On

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My Sissy Summer Continued

My name is Veronica..

Inside my cousin's room, I stripped naked and headed straight for her panty drawer. I felt giddy with excitement as I looked for the sexiest lingerie combination, sifting through her silky garments and pulling out a pretty pink bra and some panties. I reached back into the dresser drawer, desperate for a garter belt and stockings to complete the set. I was shaking as I put on the...Read On

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My Neighbor's Wife

If you want to keep things private, close the curtains!

Carol, my neighbor's wife, had been suspecting for some time it seems, and when her husband had to go away for several days she took it upon herself to confirm her suspicions. That was the beginning. It was early morning when there was a knock at the door. I thought 'What the fuck? No one comes to my door!' I was surprised to find Carol at the door. Although Carol was smokin' hot. She had...Read On