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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.

12

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

9

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

3

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

3

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

14

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

19

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

15

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

9

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

10

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

13

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

17

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

11

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

12

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

4

Happy to be Used (Pt. 5)

I finish my day of private booth service.

I was walking gingerly in my heels and panties from the assault my ass had just received. While it likely looked like I was just trying to be more effeminate, my ass hurt so bad it was the only way I could walk. When I reached the front of the store I saw Sir talking to an older man who was behind the counter with him. The man appeared to be in his early sixties.  I looked at him and Sir...Read On

7

A Night of Firsts

Jessica goes out for her first time and finds herself and a lot of fun

I have been crossdressing in private since I was young. Now in my late forties and after three failed marriages, I had decided to step outside as Jessica. So after a lot of planning over several months, the day had finally come. I stepped in the bath as JD and shaved any hairs on my body that should not be there. It did not take long as I had been preparing my body for weeks to be smooth....Read On

5

Being a Bride

Jessica gets to be a bride for her man

The alarm went off and I turned over in bed, I could not believe the day had finally come. I slipped out of bed and adjusted my satin night dress, fixed one of the spaghetti straps on my shoulder and covered one of my breasts that was exposed. In the kitchen I got myself a juice and croissant and sat at the table. My thoughts went back several months to my first meeting with Steve, I...Read On

11

Exploring Even Further

Shauna meets Jerry's wife and things get heated.

For the rest of the week I was a total wreck, dreading, craving, anticipating, and fearing, the arrival of Jerry’s wife and Rocketman69, whose real name I'd discovered was Jim. Just thinking about all of the possibilities had me literally trembling with lust and, at times, fear. Jerry, too, was in a constant state of arousal. Neither of us could believe what a slut I was becoming. After work...Read On

8

Happy to Be Used (Pt. 4)

Another Saturday, another visit and an escalation of my submission.

I woke up Saturday morning after a fitful night of sleep. I was so excited for the coming day I couldn’t get comfortable in my bed. I beat off once before I went to sleep, once in the middle of the night and once in the morning. All I could think about was the last two weekends and what might happen today. I got out of bed and drew a bath for myself. I was ready to prepare myself for my day...Read On

9

Being Suggestive

Cari seduces a handsome but dominant man.

As a young college student my life and my dedication to the joys of being a transvestite had become conflicting. I had to put my college classes first, but living off campus made my female life so much more workable on weekends. I now looked at my sexy mini-skirted flirty self in a very different way now that I had discovered that attracting men had a quite enjoyable side. I realized that...Read On

7

Happy to Be Used (Pt. 3)

I voluntarily return to the adult bookstore.

I replayed the weekend events literally every moment of my life for the next three days. I could not stop thinking about everything I had done and everything that had been done to me. I had planned a visit to the glory hole for so long I could not believe it had happened. And all those thoughts were, of course, drowned in the sea of memories of what had actually transpired. My plan had...Read On

4

My 2 AM Phone Call (Part Five)

The night got more exciting when they strapped me in

Bondage means different things to different people.  To some, it just means being tied up, but I always felt that true bondage means a lot more.  It can mean total surrender to the situation I find myself in and total embracing of the situation, knowing I can't do anything about it. When I looked more carefully at the machine that was in front of me, I realized that this was to be a...Read On

9

Happy To Be Used: Pt. 2

Part 2 of my planned book store visit, which did not go as planned

As soon as I felt him touch the plug I knew things were going to change. He had already taken control of me, and the situation, and knowing that I liked things up my ass would only give him more encouragement. His hands quickly figured out that I had something up my ass and he played with it for a moment before I felt him lean forward, pressing his weight against my back while his right...Read On

2

Being Christy - Part 4

Christy gets her man

I looked down at the city, checking my bearings and searching for the landmarks I knew. The station, the canal district, the shopping streets. At least if this didn’t work out I’d be able to find my way back. It was a dark, clear night and the skyline glowed through the clear glass of the 20th floor apartment I found myself in. I was in a modern, open plan living room which took up a corner...Read On

20

A Saturday Afternoon Visit to the Office

I get to let the sissy in me cum out during a Saturday afternoon visit to the office

I usually work from home as I have a very private place with a wonderful view and Lord knows I’ve put in more than my fair share of office hours over the years. But I do occasionally elect to make visits to the office both during normal office hours and off-hours to make copies, restock my home supplies and have a cup of coffee with a long-term friend or two. Usually when I do hit the office,...Read On