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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

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

7

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

11

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

3

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

6

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

4

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

9

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

8

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

3

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

28

Night Trawling: The Crossdresser

Sometimes the streets offer the most delicious surprises.

The streets of Pomona live two lives. Like maternal twins, they coexist in parallel, appearing as virtually identical to those merely passing through its old and storied neighborhoods.  During the day, with the sun high overhead, myriads of people — whether they’re commuters traveling like drones or soccer moms distracted by their busy lives — they choke the streets in a constant pulse of...Read On

4

Being Christy - Part 3

Christy finds release after moving to university

My experiences with Jenny and James had been amazing, but summer drew to an end and it was time for me to take up my place at university. I didn’t need much and only took a couple of bags with me, but the move did mean saying goodbye to my sister’s wardrobe. My parents gave me a lift to my student digs and after some typically over the top parental farewells, I was left alone three hundred...Read On

Stranger Fuck

A crossdresser is pegged in a sex club.

  I noticed the time strike 10pm on my watch as I got out of the cab outside the Red Circle. Hopefully tonight I was going to get lucky. After paying the cabbie and stepping out of the cab, I fixed my tight pink and black striped dress as I stood outside the club. The Red Circle was the most notorious Sex Clubs in the city where couples and singles went to hook up. Tonight was their...Read On

22

She Made My Dream Cum True

A girlfriend helps me bring out my inner slut

I had been seeing Ellie for a few months before I told her about my little secret.  We enjoyed straight sex, but something was always missing for me.  After I told her about Vanessa, and my desires to dress up and be treated like a woman, I was really scared she was going to cut and run, but she actually was interested in knowing more.  I confessed some of my innermost desires to her.  I...Read On

4

Taking That First Step. A New Chapter Begins. Part 2

Cassandra's new idea

September had arrived and Lance returned to high school for his final year. He still found himself attracted to and flirting with all the girls and not the guys. He surmised that it was only when he was dressed as Lana did his choices change. He couldn't see Cassandra during the week as he worked out after school and then went to his part-time job. He got home in time to join his family...Read On

10

Soldier Standing to Attention

A soldier and the slutty nurse

I had been flirting with a soldier that I had met online for a while. He was a lot younger than the guys I normally go for, but surprisingly open minded for his age. He was also really hot and had a nice body, so I agreed to meet. We toyed with the idea of some roleplay during our online chats. My favorite was the wounded soldier and the slutty nurse; it made me very hot. I got myself a...Read On

23

My First Time With Two Guys

I got more than I bargained for when I met a guy for sex

I had made a date with a guy I had been exchanging emails with on and off for three months. He seemed nice enough and was pleading with me to meet with him. He convinced me to meet him at a nearby hotel and left the key at reception. Then, he was going to wait at the bar whilst I got ready and I would text him. Then, he would come up to the room and let himself in. I arrived at the room,...Read On

12

Taking That First Step. A new chapter begins

Cassandra introduces a new pleasure.

The Summer was drawing to a close, and Lance would soon return to school for his senior year. As excited as he was about his final year, he was saddened that meant no more early morning rendezvous with the stunning Cassandra. It had been a great Summer. Thanks to her assistance Lance had taken his desire to crossdress to a whole new level and he became Lana. In order to complete his...Read On

2

Alexia's Tale Chapter 3 - Sensual Outgoings

Venturing out to embrace her fem side, Alexia discovers a glimpse of her desires...

Sunlight beamed through the curtains, warming up the room. Under the sheets, a mildly aroused Alexia laid half asleep, one finger halfway up her ass and her mouth gently sucking on her other hand’s fingers. Her cock was slightly bulging, as it tried to break free from its fabric cage, causing it to pull on the thong. Her hair was messy, but in a way that you’d love to see after a good...Read On

15

Busted by My Step-Sister's Boyfriend - Chapter 1

My Step-Sister's boyfriend catches me watching the two of them having sex

My step-sister Alicia is two years older than I am and built like a Greek Goddess with her braided blonde hair, slender body, long silky legs, tight round ass, and 36D breasts. Her boyfriend Bob is a college freshman soccer player who regularly spends the weekends at our house. My parents do a lot of weekend travel to relieve the stress of their jobs, so the house is virtually ours to...Read On

4

Alexia's Tale Chapter 2 - Online Exploration

Continue the tale of Alexia as s(he) goes down the path of being a gurl!

Looks like it's never gonna stop," Alexia muttered, the warm vapor from the cocoa rising past her face like a discounted sauna. Her voice pitched higher, much to her liking, she continued, "twenty-four years old, with a job as a writer. Yet I'm bored." The maroon cardigan wrapped her exposed shoulders, but did little to envelop her breasts upon which she rested her hands that held the...Read On

3

Rainy Day For Alex(ia)

Alex copes with a rainy day Sfw. Please comment, rate, and i'll develop her NSFW!!!

The smell of rain danced near his nose, as Alex sat by the window. It had been raining for two hours now, with no sign of stopping. The clouds were ever so gray and the wind gave the trees reason to dance. “I guess I know what will make this afternoon cozier,” he said, making for his wardrobe.  Passing his mirror, he caught sight of himself again, 5 foot 8, 62 kilos, with long brown...Read On

17

The man of My Dreams - Continued

I opened my door and there stood my beautiful black lover!

When the second day of my conference was over I returned to my room to change and become Melanie.  My hopes was that my beautiful, black god with his massive, uncut cock would be waiting once again at the bar.  For tonight I chose a sexy floral mini dress.  It was a white background with a floral print.  It had a tight strapless bodice and a full skirt.  My heels were 5 inches with a 1...Read On

20

I met the man of my dreams

I noticed him at the gym when his cock was peeking out from under his shorts

I work from home and only have to go into the office at the beginning of the week and at the end.  So with travel and time in the office and a few extra chores, I dress in guy mode about 10-12 hours a week.  The rest of the time I am Melanie!  In the morning I dress as if I am going into the office.  I often wear a skirt and pretty top or a dress.  I always wear hose, my wig, full makeup...Read On

29

My best friends dick

After giving my first blow job it was time to let my sissy ass be fucked

I was a closet crossdresser with a crush on my best friend and finally, after we had both graduated I worked up the courage to show him how I felt.  I invited him only and met him at the door dressed in my sexiest/sluttiest outfit.  I fell to know knees and gave him his first bj.  It was also the first j I had ever given.  It was wonderful for the both of us.  It was something I had wanted to...Read On