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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.

7

Bought

A pretty transvestite finds money can talk!

I love the transvestite lifestyle. Since I was sixteen, I have been boldly going out dressed to the nines as Cari in public. Now finally of legal drinking age, I go out to one of Boston’s gender friendly nightclub establishments on the weekend. I am lucky to be considered one of the prettiest and the most believable of the girls at these clubs. At five foot five inches tall and one...Read On

1

A Satin Dream Comes True

An encounter with a dominant transexual escort

I’d explored my fantasies with a transsexual escort several times and after my last encounter, which was the basic girlfriend experience, though she did wear a corset and stockings with satin panties as I asked. She was very open to fantasy play I have long had a scene I’d wanted to play out and she seemed to be the perfect gentle dominant. Now my thing is dress up. My iconic Mistress isn’t...Read On

8

From Sam to Sarah: A Genre-Bending Story of Personal and Sexual Discovery. Chapter 3

The plan was set. Would I be able to follow through with watching my girlfriend get fucked?

Aubrey had just finished building up my confidence to the point where I was ready, as ready as I would ever be, to cross the threshold of that door and make my first public appearance as Sarah, the female persona she had helped create for me to trick her side-guy into letting me watch them fuck. She told everyone that I was her lesbian roommate; that was the cover. Our heels clicked on...Read On

9

The Skimpy Red Dress

A transvestite's alluring dress leads to unexpected consequences.

There is a very special sensuality in the image of a pretty blonde haired girl who is petite and shapely enough to be able to look great in a tight and skimpy dress. I confess to owning many of these types of sexy dresses. Because I am five foot five inches tall and slim, I am able to look rather alluring while dressed in one. I have many styles and colors and usually favor black. Once in...Read On

4

A Day In The Life... Of My Wife! (Part 2)

A fictional fantasy based on true characters.

So far my day as 'Vicky' had been eventful. I had fucked Kevin from 'Carpets' and sucked my Sales Director's cock. I'd also swapped my soiled panties with Angela Willis, the company's top salesperson. And it was still only two o'clock! As I sat behind my wife's desk gathering my wicked thoughts I heard the girls filing back to there workstations in the adjacent office. I contemplated taking...Read On

18

From Sam to Sarah: A genre-bending story of sexual and personal discovery. Chapter 2

Sam's request is honored in a most unusual way.

The anticipation was eating me alive. My girlfriend, Aubrey, a strikingly sexy, gorgeous, blonde, polyamorous, bombshell grad-student and I had been living together for about three months. She had taken my virginity and was the dominant one in the relationship. She had been fucking another guy, Scott, every other weekend for about two months, and I had finally asked if I could be there in...Read On

11

Sex With Wife Who Doesn’t Know

Secretly wearing panties while sex with wife

A little about myself. I have been married for 40 years. I work in a professional career and I secretly like to cross dress. My wife does not know, or, I suspect she might, but prefers to not acknowledge it. I started dressing about twenty years ago when our two daughters were off to college and we were empty nesters. Out of curiosity I tried my wife’s panties on one day while she was gone....Read On

6

A Meeting of TV Girlfriends - Part 1

The meeting of two TV friends and future lovers.

I spent my day getting ready - shaving all over, showering, and cleaning myself inside too.   I gave myself a close shave and then moisturised fully.   My outfit was set - black holdups, matching red & black satin bra & knickers (a thong, maybe), black PVC midi skirt (or optional mini-skirt), and a dark lacy blouse.   Black patent stiletto heels.   Jewellery included rings, bracelet, watch,...Read On

10

Another Halloween Party Part 1

I managed to control my temper when the program director informed me that I would be making a personal appearance to function as an emcee for a Halloween bash. I thought my promotion to full time air personality would change things. I was wrong. Now, before I could launch into my rant my boss informed me that this was a costume party at the popular nightclub that was located inside of...Read On

9

Realized Fantasies. Chapter 1: Exposure

Secretly a sissy, Steve becomes Steffie and is coerced into servicing those who outed him/her.

Steve wasn’t sure, but he thought he heard the bathroom door close. He was in the shower and the bathroom fan was running, so he stopped for a moment to listen. Maybe one of the guys came in to use the toilet, he wondered. “Hello?” he said aloud. No reply. It was probably just one of the other guys getting something they’d left in the bathroom, he thought. Steve was one of the last to...Read On

8

A Day In The Life... Of My Wife!

Just another day at the office. (Part One)

 I'm not one to conspire with the opinion that women are the weaker sex. The power they have in their sexuality is greater than the strength of any man. I call it "The Power Of The Pussy." As a life long transvestite, I envy the power that my wife Vicky possesses. I envy her whole sensual being. Even in her late fifties, she can still give her work colleagues, decades younger, a run for...Read On

11

Vicky's Mrs. Robinson Moment

My wife the company cougar.

  I had heard my wife Vicky mention the name Scott a few times over the last couple of months, and by her account, he was a polite, good-looking young salesman. I remember asking her if he was fuckable, and her reply was "Yeah! If I was twenty years younger." My wife Victoria is at the wrong end of her fifties. In truth, she could pass for mid-forties and is considered a 'cougar' by...Read On

10

How to Treat a Lady

A pretty crossdresser learns how to please a man.

Being a pretty, petite, believably passable crossdresser makes me a very happy person. I have been dressing up as a sexy girl while daring to go out in public for the past two years since I was sixteen. I have had this urge and desire to dress as a female for as long as I can remember so I have gradually come to accept that I have a feminine side that needs to be nurtured and encouraged. I...Read On

7

My Mrs. Robinson Moment.

Toby's little problem.

Annabelle could not have known the Pandora's box she was asking me to open. It was during post-coital conversation that she expressed concern for her son Toby. "He's high from morning to night, and I'm sure he's dabbling with speed." Toby was Annabelle's thirty-year-old son. She was oblivious to the fairly recent encounter I'd had with him. As indeed Toby was! She rudely interrupted...Read On

2

Being Christy - Part 5

Christy gets it all.

Leading me towards the bed, Nick pulled me into his arms and I willingly let him. I lifted my face to his and parted my lips, inviting him to kiss me. Our tongues probed each other, our lips moist and eager. Nick was moving his hands all over me – to my face, my neck, then travelling firmly down to my sensitive waist and kneading my panty-clad buttocks. I couldn’t help myself from melting...Read On

2

Towards an Advanced Degree - Part Two

Cari seduces a handsome but dominant man.

So it began. My next official act as Daddy’s submissive slut was about to begin. I was strapped by ankles and wrists into the sling. The sensations of complete helplessness had me even harder than I’ve ever been. I was lit up with an acute awareness of my sensuality and the need to surrender my body completely to him. My surrender was like some kind of strange relief in my heart. I was his and...Read On

6

Towards an Advanced Degree - Part One

Cari seduces a handsome but dominant man.

At age eighteen I had finally made it into one of the best universities in the country, yet my true life lessons and deepest learning would ironically take place for me during the weekends. I’ve had the complicated urge to dress up as a girl since my early teens. Eventually I consciously chose to act on my need to do so. Though I live a mostly normal existence and also do enjoy my male side,...Read On

15

My first time in a bar

The first time I met a guy in a public bar for a drink

For a while now I had been chatting with a sweet guy named Allen, who was bisexual and was eager to meet a crossdresser. He was very muscular and handsome, a hard body but with friendly eyes. He seemed to really like my pictures and said he had cum, stroking himself, while looking at them several times, and was eager to meet me in person. He wanted to meet in a bar which is something I had...Read On

18

A New Friend at the Adult Toy Store

I am usually not this forward, but he was so handsome.

I decided to go to my favorite Adult Toy Store.  Now, this is not one of those dark, dingy places that make you feel uncomfortable.  It is well lit and attractive.  The people who work there are very nice, polite, helpful and make you feel right at home.  So I can go and feel at ease while I browse.  This store carries lingerie, clothing for clubs or stripping, stripper shoes, toys, and...Read On

16

Service Call

What a service call!

I spent the entire morning and afternoon to transform myself into a busty, curvy woman. I did my typical routine to feminize my face and make my body look womanly. I shaved very close, three times. I moisturized my face. I added concealer, and then three coats of foundation. As I waited for that to settle, I cinched my waist. I added my very real feeling and looking breast forms. I lined...Read On

10

Cum Ahead If You Think You're Hard Enough

A tale of two old folk fucking.

"You don't get as hard as you used to!" I thought my wife's assessment of my current condition a tad harsh, especially on my 63rd birthday. We had been celebrating the occasion at a local luxury spa hotel. The evening had been a success so far, with copious amounts of alcohol consumed by both parties. I had stuck to wine, but Victoria's tipple list consisted of grape, and grain, and more than...Read On

6

Finding Tammy

Tammy is made

John knocked on the door to his friend’s house and it swung gently open. The latest chart music boomed from inside.  He called out, “Hi its John?” No answer; so he went further in the house the music was coming from upstairs so John went to investigate. He needed to find someone so he could pick up the money. The music was louder upstairs and though he called out again no one answered. ...Read On

15

My Secret Revealed

My life was pretty good. I had an excellent job that paid well and afforded a nice mobile home. I played baseball on the company team and had a bevy of office hotties show up to the games to cheer me on, I even dated a few of them briefly. It was the nights that I really looked forward to. Once the day was done and I was safely behind the drawn drapes and locked doors of my trailer...Read On

11

The New "Gurl"

Transforming mind and body one nylon at a time.

Every since I was four or five years old, I can remember being extremely interested in girls’ and women's’ clothes.  This interest continued on and off throughout my childhood, and became quite an obsession during my teenage years.  At sixteen, a most exciting experience occurred that I shall now recount in detail with help from my diary.   During my teenage years, I was raised by my...Read On

14

Sissy Transformation Party

My dream's are realized, in more ways than one.

The day I have been waiting for had finally arrived. Today was the day I would be transformed into a woman. My dominant girlfriend had the idea and enlisted a few of her friends to help out. My girlfriend's instructions were specific.  I was to check into a hotel and wait for them to arrive. When they finally arrive, they were not empty handed each carrying a suitcase. Everyone was smiling...Read On

16

One's A Crowd

I almost lost my home... instead I found a date.

After my boyfriend and I broke up, I was devastated and it didn’t get any better after he left to be with his new love.  We shared a house together and had to be creative just to lease the place.  We posed as a married couple because the owner was a major homophobe.  Twice a month, just so we could pay the rent, we would play up our loving couple routine in full costume.  Which wasn’t hard...Read On

12

Unexpected Turn of Events

Jessica meets a neighbour at a bar

I sat in my favourite bar sipping at my glass of Chardonnay; I had been coming to ‘The R Lounge’ for a couple of years. I watched the guy talking to his friends across the room. They were all dressed with a bit if style but he had caught my attention. He was wearing trousers with a casual blue and black stripped shirt. He was probably five feet nine inches tall. He had an average build; not...Read On

8

Memories of Anne

Jessica's new secretary learns the consequences of mistakes

The time on the mantle clock showed 9.20pm. I sat on the sofa and slipped my heels off and tucked my stocking clad legs under me. I picked up my glass of Chardonnay and took a sip. My thoughts went to the events of today. It had actually all started a month prior. I was recruiting for a new secretary when Anne’s curriculum vitae had come across my desk and it struck a cord with me. So I...Read On

4

A Weekend away

A weekend in a hotel turned out to be more that was expected.

Stevie had always wanted to have a weekend away with a load of like minded people, i.e. trannies and admirers. He decided to find a place where he could do this and be the real Stevie, or his girly name, Lucy Lou. He searched the net and found a place about two hours drive away. He booked it and counted down the days to be there. He had bought some new stuff and had practised his makeup....Read On

13

My Early Story

My girlfriend helps me learn and explore.

From my earliest memory, I liked trying on girls' things. My mom’s slips, sister’s panties, even my aunt’s nightie, (that is another story). I even went as far as dressing up completely when I was home alone. Mostly I wore my sister’s things. I loved her short shorts and halter tops. We were about the same size even though I was a year older. I didn't necessarily want to be a girl, just dress...Read On