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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.

2

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

10

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

1

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

3

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

12

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

16
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

3

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

3

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

2

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

14

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

10

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

20

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

12

A Close Encounter (Part 1)

Not just another crossdressing story.

A few weeks ago my wife remarked on how "the gals" hadn't had a night out in months and suggested that we should perhaps go out later that evening. "What! Yeah, sure! What's brought that on?" It wasn't like Judy hadn't been around, on the contrary, she'd been around twice last week. I'm one of those cross-dressers whose wife gladly shares her wardrobe. And Samantha's the kind of wife that...Read On

6

Another Road Trip Story. Part 2

As Gary was returning from his car with his cases, he bumped into Silky who was standing in the living room. He had not redressed and was wearing a plain terrycloth robe. He asked Gary to join him in the kitchen before cleaning up. Steaming cups of coffee waited for them on the kitchen table. After taking a seat and enjoying the first sip, Gary noticed that his new friend appeared nervous. ...Read On

5

Another Road Trip Story.

With trembling fingers, he began to pack his large suitcase. First, he started with some of the silkiest and sexiest lingerie in his extensive collection. At least a half dozen silk and lace bikini panties along with tiny silky thongs were placed inside first along with their matching bras. Garter belts made of satin and silk came next. A half a dozen pairs of black nylons that were...Read On

12

A Dirty Fantasy

I just have this urge…this fantasy…

Tuesday I’m looking at the parcel on the table right now. It seems a big box for what’s inside but that’s packaging for you. I offer my thumb up to my mouth and bite on it; nibbling at the skin before my hands come down on the packaging. I pick up the knife and rip open the seams; spilling out the contents on the table. I feel excited. Like this is something I have always wanted to do,...Read On

14

An Introduction To My Crossdressing

Celebrating 50 years of Crossdressing!

Many of the crossdressing life stories I've read on Lush have similar beginnings. The early adolescence, the mother's or sister's clothes, the masturbation! It's fifty years since my first urge to dress in feminine garments, and ever since then, it has been an integral part of my colourful life. I remember the day fairly vividly. I was settling down in our bathroom, to do what EVERY...Read On

7

The Car Wash

Bent over a Cadillac.

I woke up early, because I had some early morning business to take care of. Since business was in another town a few hours away, I decided I would dress up a little gurly for my drive there. I figured I would wear some short-shorts, and change after I got to my destination. So, since I woke up a little horny, I cleaned myself out, and jumped in the shower. I shaved my face, and shaved...Read On

15

My Sissy Summer

Discovering my feminine side

It was a hot summer and my parents had sent me to stay at my aunts house while they went away on vacation. My aunts house was huge, so big that it was easy to get lost in one of the many rooms that now lay mostly empty. My uncle had left years ago and my cousins had all long since moved out, all except for the youngest, Veronica, but she was away at college. My Aunt worked during the day so...Read On

11

Taken Outside For The First Time

How I was taken outside by my lover and he left something inside of me.

Another true story. Back in the ‘90s, I lived in Manchester. Nowadays it is a vibrant city with a fantastic LGBT culture. Back then it was a grimy city. The gay “area” was Canal St, and it was seedy. Meeting like-minded people wasn’t easy, it wasn’t accepted. I was also struggling with my sexuality. I had been dressing on and off, with regular purges of course. I was trying to convince...Read On

4

My New Life As A TGurl Slut - Pt 4 - DP'd By The Bouncers

True story about a wonderful night last month at a trans club...

Jack was the first person I met on my first night out dressed as a girl... a sexy, slutty girl. He is the head bouncer/ co-owner of the security firm that deals with security for various gay and tranny nightclubs including this particular TS/ TV/ CD club which was my first introduction to 'the scene'. And I must say it's an awesome club. The trans scene is much larger than I realised but...Read On

10

Old Dressed Virgin at the ABS

Old CD gets some action at the ABS

So it started with putting on one of my sister's dresses when I was sixteen. It was a long velvet dress and felt incredible on. Prancing around the bedroom, I felt super sexy and so turned on. I was skinny, blond, smooth and could look like a young chick. So turned on, my cock was throbbing. Within ninety seconds I shot a huge load inside the dress. Funny that I had no thoughts of men,...Read On

10

Encounter With A Stranger

Met with a stranger and had some fun.

I have been dressing in women's panties and stockings for all my adult life. It's a huge turn on for me. I have always considered myself straight, but as I have got older I have become bi-curious, only when I'm dressed up though. I was out of town on a business trip and I went to Walmart and bought a pair of panties, stockings and a mini skirt. I then went to a gas station bathroom and put...Read On

5

Car Park

Out in public dressed

I finally got the nerve to go out in public dressed. I've been dressing in private for years. It started with panties, Some of my wife's, some of in-laws that have stayed with us from time to time. I finally got the nerve to buy some at a store. So exciting, looking at panties wondering how they will look on you. Took a while to find my correct size; I like them tight not no so tight I fall...Read On

9

An Old Friend Comes to Visit

An old friend comes for a visit and surprise.

Five o’clock finally arrived and it was all I could do to stop myself from doing  handsprings out to my car. I’d really done nothing but fidget in my chair all day anyway. The only thing on my mind from the moment I woke that morning was my plans for the following week. An old friend would be arriving to stay with me and I’d taken the following week off so we’d have nine lust filled...Read On

7

My New Life As A T Gurl Slut - Pt 3 - Nine Cocks in 48 Hours

A true story about a recent horny, cock-filled weekend with hunky men and hot tgurls

I was going to be the gurls' slutty French maid for the night and couldn't wait to get to Karen's so the fun could start with four hot t-gurls and four hot cocks for my mouth and ass.   Lucy picked me up, and as soon as I got in her 4x4, I slipped out of my jeans to reveal my knee-length black boots, black lace top hold ups, black suspenders, and wet look black micro mini skirt. I unzipped...Read On

14

Across The Street. The Conclusion

Mike left his telescope at the window even though it wasn't used any longer; his laptop was the new tool of choice. Every night around midnight he would receive a chat request and a second later Leann's beautiful face would fill his screen. There was the usual small talk about their day as Mike stared at her pretty face. They didn't have to talk about sex. Between her looks, dress...Read On

7

Vanessa and Ken's Second Date

A forbidden second date draws us closer.

It had been a couple of weeks since Ellie and had our little trysts with Derek and Ken, and I couldn't stop thinking about it.  As much as I loved being with Ellie, there was something magical about that night with Ken.  We had talked about it, and I downplayed how wonderful it was to make love to Ken.  She told me that she enjoyed her night with Derek too, but she didn't really seem to make...Read On

11

Across The Street. Part 3

Mike was leaning back in his desk chair enjoying the after-effects of his orgasm. He leaned forward and looked into his telescope to check on Leann. He saw that she was still in her chair with her eyes closed and her legs spread, floating down from her orgasmic high. As he flopped back in his chair, he still couldn't believe it. The girl he had been spying and masturbating to her...Read On

8

My New Life As A TGurl Slut - Pt 2 - 2 Men, My Girlfriend & Me

True account of my recent first experience with men

It was only two weeks earlier that I'd met Lucy and the girls but what a fortnight it'd been. I was having the time of my life being girly and feminised so much of the time, being given an endless supply of gorgeous new lingerie, clothes, shoes, boots, and costumes to try on and wear - on top of my own already extensive slutty wardrobe.   All the girls took turns doing my hair and makeup...Read On