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Crossdressing

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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.

111
Legendary Story

My night as my wife's sissy boy

My wife surprised me, and how! It Was a night I will never forget.

The last few weeks had been extremely busy and my wife and I had very little time to spend with one another.  We needed some alone time so we made arrangements for the kids to spend the night at their grandparents house.  My wife asked if I would mind dropping them off by myself as she had a few things she like to get ready while I was gone. As I pulled into the driveway I...Read On

82
Legendary Story

First time sex with a man!

How my first time anal started and happened.

So there is this guy who I've been talking with for awhile. I wasn't too interested because I was still on the edge about meeting up dressed with another person. At the time I was under the influence and I sent him this message.   "I have recently been dressing up more as a woman as my family have been busy. I have been eating my cum all dressed up like a sissy! I have been eating my...Read On

33
Legendary Story

Caught dressed like a sissy slut

My girlfriend was away for the weekend so I had the place to myself. I was feeling incredibly horny so I went through her knicker drawer and decided to dress up (which I've enjoyed many times before). I put on a really tight, pink thong, black fishnet stockings and suspenders, and her black mini skirt. I looked at myself in our full-length mirrored wardrobes. God, I looked so sexy and...Read On

44
Legendary Story

Caught

i was caught by my Hated(at the time) Step-father

I see all these girls with the first time or the first time they got caught dressing and it turns me on looking back and thinking of mine. Well I was young when I started getting into my moms and soon to be step sister’s clothes. My mother divorced my father when I was young but never really knew my dad do to the fact that he was always in the military and my mother was tired of moving...Read On

107
Legendary Story

My First Time in a Dress

How I Became a Crossdresser

PART-1 When I was younger I used to go and stay at my grandmas house during the summer. It was a small country town with about 15,000 people. She lived on a quiet street and there was only a couple of other kids close to my age. I used to go and hang out with one guy, Dan who was about 3 yrs older than I and his sister, Pam who was my age. Dan and I used to go mess around everyday....Read On

32
Legendary Story

My first halloween night as a teen CD!

My first time i dressed up like a chick and how lucky i got that whole night

This is halloween!! A day that everyone goes out and dresses up in costumes and other things, and go to parties and drink and show off their wild side until the wee hours of the next day. And I thought to myself, since everyone goes out and wears costumes, why not dress up myself into something wild and willy?? Or in fact, why not dress up in a manner of expressing who I am and what I...Read On

24
Legendary Story

The Feminization of Michael - Chapter 1

The Feminization of Michael. Chapter 1 How I had found myself in this predicament Ill never fully understand. Ok I guess it was my own fault but why I didn’t kick against it when I could Ill never know. I had been involved in a sordid night of drink drugs and sex with a young transsexual hooker! Including her/him putting a bra and panties on me! I didn’t know any of this until my...Read On

51
Legendary Story

The Party

It happened one halloween

I am a closet cd. It was Halloween. My wife called from work and said she wanted to go to a party at a friends house. It was a costume party. She said she had a costume and I was to wear one as well. What, I don’t have one. Yes you do, your going as a girl. But I’ve never done this. Well you’re going to tonight. No one will care because it’s a costume party so get dressed...Read On

44
Legendary Story

A Visit

Husband dresses up for his wife so that they can have a little fun during the weekend

My wife knew of my enjoyment to wear women’s lingerie when we married and over the months that followed our honeymoon she had often wanted to see more of me dressed up.   I always enjoyed these times although they were not as frequent as I would have liked them to be. One Friday, after a rather long and difficult week at work, I returned home and was greeted by a tender hug and a loving...Read On

47
Audio version available
Legendary Story

Panty Slut

Caught wearing my panties, he soon gets a taste of his own medicine

You little bitch! I can’t believe you're wearing my panties again. Do you want to be a girl? Do you? Well that bulge in your panties tells me you're lying. Come on in here Jennifer. That’s right, I told Jennifer all about you jerking off in my lingerie. I don’t think she believed me. Stay right there so Jenn can see what a little sissy you are. Isn’t he...Read On

41
Legendary Story

My Unexpected First Time With a Man

How a night of anal play, and crossdressing turned out to be my most intense sexual experience ever!

In the Arizona heat... It was Friday, the first day that I would be alone at home while my wife was on her trip. It was also the day that I timed a delivery of some clothing and accessories for a weekend of crossdessing and anal play. As I sat at work repeatedly checking the status of two shipments, one was a box of dildo's, lube and anal plugs, and the other was filled with lingerie, a wig,...Read On

48
Legendary Story

My New Sissy Life

A sissy lives out her ultimate dream.

I was so stunned I was unable to speak. I only thought things like this existed in my fantasies and could never actually exist in the real world. It had been three weeks since I found an ad posted online seeking two submissive males for "training." I read the description which said, "Attention sissy boys! Have you ever wished that you were a trained sissy slut? Of course we both know the...Read On

56
Legendary Story

Wife's Crossdressing Fantasy

My journey from boy to man to woman

This is a work of fiction. Any resemblance to persons or incidents is coincidental. My adventure began while I was a senior in high school. My mother took me to the dentist. It was late afternoon and shortly after I was called into the examination room the receptionist and assistant went home. The dentist then closed the door of the room we were in. He walked over to me and started making...Read On

35
Legendary Story

Feminized

My first time in panties

We had just finished making love, but Amy was still not satisfied. “I wasn’t done,” She complained. “You came too soon! Let’s go at it again.” “You know that I can’t get hard again this quickly. It will take me a couple of hours to recharge my batteries before I can fuck you again.” I replied. “That is completely unacceptable.” she pouted. “There must be something that we can do. I...Read On

65
Audio version available
Legendary Story

In My Panties!!!

Sarah discovers Larry's secret.

Larry and Sarah were your typical yuppie couple working two professional careers. Larry a techno wiz was the research and development department head at a local manufacturer while Sarah was the office manager at a local Saturn car dealership. Their weekends off work were filled with their hobbies of camping and outdoor fun. Both loved nature and enjoyed their time together on beaches and in...Read On

89
Legendary Story

Caught, Used and Loving It!

I was caught dressing up as female and used like a toy

I knew I had time now; my wife had gone out with her friendsand wouldn’t be back until 10pm at the earliest. As it was only 6:30, I knew I could spend time getting ready before playing around on the computer and enjoying a nice relaxing but exciting orgasm. My cock was more than ready as I hadn’t had sex for over a week and no chance to masturbate either due to either the kids being around or...Read On

41
Legendary Story

First time with a man

I have been crossdressing since the age of 11 years old. I never really considered myself anything other than straight. Up until I turned 19. I often fantasized about other guys when I was dressed but that's as far as I took it. The year was 1984 and one day I decided to stay home from work to play. I get dressed up in a pair of purple satin string bikini panties,matching bra,black...Read On

40
Legendary Story

I become my wife's girlfriend. The beginning.

My name is Tony and I'm a regular straight guy. This is the story about my life as the part of lesbian couple, and yes, I'm aware of weirdness of this statement. During the first period of our relationship our sex life was fantastic, a man's dream. At this time I wasn't aware of my dark fantasies, our sex was very good and I thought of us as a very nice couple. And then, something like...Read On

69
Legendary Story

Telling Mom I'm A Crossdresser

A story of me being open with my mom as a crossdressing slut andher becoming my pimp. Plz comment :)

When I was younger, my dad had passed away leaving only my mom and I. She is 45 years old with long brown hair, bright green eyes and stood about 5'10" in height. She is also a fairly busty woman with a 30DD chest with about 35" hips and in pretty good shape for a woman her age. I had been crossdressing for a few years and my mother had caught me a few times wearing her clothes. The first...Read On

37
Famous Story

A great experience as a crossdresser

Glorious glory hole session

I was born and grew up for the first 27 years in England. Ever since I was 16 years old I have always had an infatuation with sexy ladies lingerie. I used to dress up in my mothers and older sisters lingerie and get very turned on and wank myself off while dressed up. I am now 53 years old and still tremendously enjoy the thrills of dressing up and wearing sexy lingerie. One of my...Read On

60
Famous Story

Dressed Up and Used

Young Crossdresser gets Fucked again

     This is a continuation of my first story "MY First Time in a Dress".  I love reading your comments, enjoy!      I avoided Dan for the next few days by playing sick.  I was not ready to go over to his house again yet.  My ass was so sore the next day I had to have some relief.  I was still having a hard time comprehending what really happened.      I finally went to his house...Read On

38
Famous Story

Mom's Boyfriend

Once mom and dad's divorce was final I moved back in with mom into our house. Dad had purchased a townhouse a few miles down the road. Being 17 and staying with my aunt and uncle had given me the freedom to do and act as I pleased, so I made no bones about telling mom that her son was a crossdresser and enjoyed sex with men. She really didn't say much and pretty much told me that as long as I...Read On

54
Famous Story

The Panty Princess

Dominant girlfriend discovers her love for submissive boyfriend

Jane and I had only been living together for three weeks when I was caught red-handed. I was mortified when I saw her in the mirror, standing behind me with her mouth wide open. She had managed to come through the front door, up the stairs and into the bedroom without making any noise. I tried to explain that it was the first time I’d ever done such a thing, but she was having none of it. ...Read On

30
Famous Story

With the wifes help

wife takes me for my first gangbang

Last night I finally lived a long time dream of mine. My wife Melody of three years came home from work around 7pm and told me to follow her upstairs. Once we arrived in the bedroom, she laid back on the bed and spread her legs wide for me. She was dressed in a long white light cotton dress with a floral print and a belt cinched at the waist. The dress fell long enough to conceal most of...Read On

44
Famous Story

Caught by a neighbour

I've secretly been crossdressing from a young age. In my late teens, around 17, I became more adventurous. maybe because I was enjoying it more. At that age I was very slender, had long dark hair as well has having a naturally smooth and hairless body. My brother and sister were both at uni and my parents would work a lot of the time meaning I was left home alone quite a lot. I would "borrow"...Read On

129
Famous Story

Halloween Trick or Treat Surprise

Dan and Susie go to a Halloween costume party Susie has him dress as a women and changes him forever

Chapter 1 –Susan Charity Event To my surprise Susie my wife of 15 years comes home from one of her many business trips. She is all excited about a Halloween costume party fund raiser, for non profit that supports women studies. The invitation states, the best couple for this evening will receive a free weekend in Bermuda. She wants’ us to go as couple switching genders.  Let me...Read On

70
Famous Story

My Strapon Fantasy

A girl helps her boyfriend live out his fantasy

I woke up in the middle of the day and smiled; my girlfriend had gone to work a few hours earlier and promised me a really good time when she got back. I ran upstairs to shower and make sure I was hairless before getting ready for her. I wandered into her room to dress for her arrival. I found a purple sheer thong and matching bra in her underwear draw that would be perfect. I really wanted...Read On

79
Famous Story

Taking Control

Wife busted me doing some of my favorite things and then took control with some role reversal

* this is a story of how my wife busted me doing some of my favorite things and then took control of the situation with some role reversal to satisfy both her and my hidden desires - enjoy! * It was one of those rare days when I was working from home and my wife had plans to be out running around with a couple of girlfriends for most of the day. Work had been dragging me down and I was...Read On

32
Famous Story

Humiliated by my best friends

I had recently met a kinky lady online who agreed to be my mistress on a frequent basis. Tasks she set me included wearing panties to sleep in, leaving a butt plug in me, while we chatted and other kinky things. Last night, while we were chatting, I told her I was going to a friend's house with a few of the guys, to play cards and have a few drinks. Her dominant side took over and she told me...Read On

33
Famous Story

Caught!

Crossdresser is caught by his flatmate and fuckec

I stood in front of my full length mirror wearing my new black heels. Not just the heels of course! I had a sexy, short black dress to go with them. Underneath, I had some incredible purple and black underwear; all silk and lace. I twisted on my heels and pulled my dress up a little, wiggling my thong covered ass at the mirror pretending somebody could see... ...And that’s when he knocked!...Read On



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