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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.

1

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

7

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

7

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

4

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

5

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

5

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

11

My New Life As A TGurl Slut - Introduction

True story about finally being the feminised, girly, cock loving slut I always wanted to be

I love cock. I've always lusted after cock and the older I got the more I wanted it. I've slept with getting on for a hundred girls and done things most men can only dream about, like lesbian thresomes with a girlfriend and one of her friends or some other babe. But secretly I craved big hard cock to suck and fuck. I've always wanted to please hunky, horny men and be their slut....but up until...Read On

21

Ashley's BBC Therapy

Her destiny gets fulfilled.

I couldn't breathe, my whole midsection was tensing up as he deepened inside me. I moaned and expelled all the air from my lungs and took a deep breath. I already knew that this would be a challenge but I had no idea that it would be so enormous. He was an alpha, by all means, he shoved it inside and split me open like I was disposable, which I was to him most likely. But why do I care? I'm...Read On

21

OMG Last Night

last night a first for me

I suppose I'd better start at the beginning. Well, my femme name is Carly Hughes.I'm a 47-year-old male who has probably been cross-dressing since he was seven. I started dressing in my mum's and sister's clothes. I've built up stashes of clothes many times and binned them through guilt. I've probably wasted so much cash it's unbelievable. Anyway, I've done all the manly things in my life...Read On

20

The Cardboard Fort. The conclusion.

The conclusion of the story told to The Phantom.

My duo identity was not an easy thing to maintain. My lingerie was washed in the half bath sink in the wee hours of the morning. I then had to creep downstairs and hang them in the fort. They along with the wig and makeup were kept hidden in an old suitcase with a working lock I found in the second-hand store. All this secrecy was necessary because young men did not want to dress and...Read On

15

The Cardboard Fort. Part 2

The story told to The Phantom continues.

That evening I thought about Gene and what had happened in their old fort. I finally had the opportunity to wear something besides the slip I  had shoplifted. I really enjoyed dressing up for his friend and what had happened as a result. I didn't feel weird or strange about it. "Maybe I should have been born a girl." I mused before falling asleep. Two days later Gene appeared at my door...Read On

21

The Cardboard Fort

A story from the sixties as told to The Phantom.

I discovered at a young age that I had a desire to wear female clothing, but not just any clothing, it had to be silk and or satin. I thought maybe it was a phase I was going through. I figured if I ignored these desires they would pass. Ignoring them didn't work and they became more intense.  I often found myself sitting and staring at the lingerie section of the large Sears catalogue with...Read On

6

My Road to Cross-dressing (Part 3)

Part three of my cross-dressing saga, where I have sex as a woman.

From the first time I dressed, there was always a sexual element. I used to find the time to wear something feminine and wank myself. It went hand in hand, so to speak. One of the things I loved doing was getting dressed up and laying on my bed with my legs over my head and wanking. When it was time, I would cum in my own mouth. I did it so many times but it was always uncomfortable, but I...Read On

3

My Road to Cross-dressing (part 2)

A more in depth follow-up to my original story about how I started cross dressing.

I had dressed up since I was a teenager but it was only occasionally. Usually, it was just lingerie and it was always for me and just for masturbation. It was about ten years ago that I decided I wanted to go further and start using makeup and breast forms and wigs etcetera. Quite by chance one day, I rang an old friend just for a chat. I found out that he had rented his house out while he...Read On

14

A Night to Remember or to Forget?

A pretty transvestite finds herself getting a little too comfortable out on the town!

As a petite, pretty, and now fairly confident young transvestite, I feel fortunate to have discovered so many things about myself. I am proud to have a slim, smooth and well-exercised shape. I have longish streaked blonde hair and my goal is to always develop and improve my feminine elegance. My friends tell me I possess a very strong believability in my appearance as a young woman. I think...Read On

13

Chasing Skirts

Sam's crush, Heidi, turns out to be a girl with unusual tastes.

When I entered college, I was a virgin. Not to say it was particularly unusual; I was a quiet, nerdy kid. I wasn’t ugly by any stretch of the imagination, but a little short, not very masculine, a little self-conscious and not hugely used to interacting with girls. I was eager to change this fact, but I felt like something of a romantic; I didn’t want a random hook-up, and besides, I...Read On

10

Be Careful What You Wish For

A say in my life.

When I arrived home I noticed a note on my computer. It read, "Take off your clothes and put them in the washer. Go to the bathroom and shower, then go to the bedroom and put on the clothes laid out for you. Make sure My toys are prepared and in the right places, then you may join Me in the living room bringing your hood with you and taking your place at My feet (on your knees, hands behind...Read On

15

Caught And Punished By My Manager (Part 2)

I had to make a sale...

I lay there on the floor, my g-string still dangling around my ankles, my vibrator rammed deep inside my ass. My boss Mei had been gone all morning, leaving me vulnerable and exposed in my lace garter chemise set, sheer stockings and high heels.  I lay there staring at myself in one of the mirrors. I felt so feminine and slutty as I wriggled my bum against the floor and rubbed my...Read On

3

Happy To Be Used (Pt. 7)

I practice my dance and slut moves at the bachelor party.

  Bachelor party Friday was finally here. I would have woken up early, but I had partied really hard the night before and so I woke up with a crazy hangover. Good thing I had until that night to recover and get ready for my performance. Being hungover turned out to be a blessing in disguise because rather than doing anything all day and using up my energy, I essentially sat around the...Read On

22

Dressing up.

dressing up in sisters clothes

It was the summer of my sixteenth birthday. It was when I first thought of girls’ clothing as the clothes I would like to wear. My name is Matt and I live with my three sisters and mother. I am the youngest and as you may realize in this sort of set up, there is no shortage of girls’ clothing for me try on. I had just turned sixteen and it was summer. As usual, the four beautiful women in...Read On

A Freebie for Randy - continued

I was becoming addicted to Randy.

The Saturday morning after giving Randy a freebie I awoke feeling happy and very horny. I was still lying in bed enjoying the smooth feel of my soft skin and the silk camisole and panty set that I put on before bed.  While I was having a good time with myself and my favorite dildo, I heard a knock on the door.  Leaning towards the window I saw the UPS man walking back towards his truck, and...Read On

14

Andrew-Andrea

A boy's experiences through petticoating, boy-boy love and back to femininity.

My mum and I lived on the outskirts of a small Scottish village. John and his mother Beth were our neighbors, and he and I were best friends from an early age, sharing everything as we grew up. At Primary School and then Senior Secondary School, we were an inseparable pair, supporting each other through the good and bad times. This idyll came to an end when we had just turned sixteen. He and...Read On

18

Lisa's Lessons

A webcam crossdresser begins to learn more about himself with the help of a generous teacher.

I used to spend a lot of time away from home for my job. It had its downsides, but it gave me a chance to do my favourite thing: show off. My toolbox had a locked compartment containing a small selection of cam-suitable wardrobe items: a single camisole, a few panties, and two pairs of nylons - one thigh-high and the other to the waist. I travelled a mostly predictable route, so I was a...Read On

11

I Dressed Charlie Like A Girl And She Never Went Back

I always protected Charlene through college, before I knew she was to be my girl.

Today is our long awaited graduation exercises. I am just waking up from last night's party, Charlene is already up and in the shower. Not surprising, because she always loves to look her best in the morning. This morning was going to be very special in honor of graduation and celebration of our almost four-year love affair. Well, at least that's what she promised. I kicked off the sheets...Read On

33

Husband Caught Cheating, Punished

Husband used by wife and her friends

This is what happens when you get caught cheating on your wife. I love my wife dearly and never set out to hurt her. I was working away from home several years ago, and while I was away I became chatty with a lady at a nearby bar. Her name was Helen; she was very well spoken and was gorgeous. I had been visiting the bar for a drink most days after work, and Helen always seemed to be there. I...Read On

8

Part 1: Abandoned Parking Lot

It begins... Well, I found out that Anne fucked that professor again. She came to my dorm, drunk at 3 am, fighting with me, calling me a little bitch and pussy, and she began slapping my face. I won’t even get started on what she was on about. I tried calming her down, but whenever I said anything she just slapped me, or if I tried to stop her from drinking more from her loaded thermos,...Read On