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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.

6

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

10

A Crossdresser Gets Caught

A closet crossdresser gets caught and has the time of her life.

Johnny was gentle and had slightly feminine mannerisms for a guy. He had had quite a few escapades with women, a couple of failed marriages and a dozen or so relationships but all had fizzled out. He had never thought about the fact that maybe he was gay or bisexual and although he was not homophobic he thought the idea was not for him.  He found women attractive and loved them wearing...Read On

2

Happy to be Used (Pt. 6)

An educational strip club trip

  Sir now knew I was his slut and would question nothing he told me to do. Though I presume this excited him, there is no way it excited him as much as it excited me. I was distracted every waking minute thinking about past experiences and future erotic scenes to come. I spent hours day dreaming and was masturbating at least four times a day. Every time I masturbated I shoved something up...Read On

5

Crazy Sex Affair With Her Sister Part 2

Our lingerie affair continues...

I'd just spent the night with my girlfriend's beautiful and sexy sister Miriam, exploring her lingerie collection and her amazing body. We'd been playing dress up for hours. She would change her outfit and pass me some new clothes, a pair of frilly knickers and a baby doll, a bra and matching thong, a skirt, some stockings, fucking each other along the way. I wasn't sure what time it was but...Read On

13

Digging up the past gets me all dirty!

My jealousy about her past changes my future

My wife Cindy had a sexual past before we met. I'd only been with a couple of girls before her but her sexual history was epic. I overheard her talking about me to one of her friends once and she said that I was the sensible choice. I was safe, I had a job, I wasn't going to treat her bad or cheat on her. Everyone has to settle down sometime. What hurt the most, though, was how little...Read On

11

Wife Makes My Dream Come True

After a long wait of ten years, my wife finally comes to terms with my fantasy and makes me her girl

I had a fantasy for dressing up since puberty hit me. I wanted to crossdress even before I knew what it meant. I always dreamt of wearing sexy feminine clothes. I could never try any female clothes at that time though, but the curiosity in me never died. When I started dating my wife, I once gathered the courage and told her my fantasy. I am sure she did not expect that and was rather...Read On

8

Caught and punished by my manager

The power goes to her head

My job as a sales rep meant I had to work away a lot, traveling around the country to various events and conferences. It suited my lifestyle as it meant I was able to indulge in my secret obsession of crossdressing.  Every week I'd pack my suitcase with a new outfit of sexy lingerie, heels, wigs, makeup, a vibrating cock; all the things I’d need to satisfy my sexual urges each night when...Read On

13

The Wedding Gift Surprise

A wedding to remember

I'd been invited to my friend Whitney's wedding, I didn't really know anyone and had only met her fiance once before in passing. I think she only invited me to show off how popular she was and to be honest she was known for being a bit of an attention seeker. After the ceremony we all started to drink and I was getting quite tipsy, which meant I was also starting to feel horny. I left the...Read On

19

Almost Caught And Forced To Watch Cheating Wife!

Secrets almost revealed, with a happy ending!

It was our monthly weekend away. My wife was going to visit her friend Karla and I was going out of town to see my friends in another city. At least that's what she thought. Really, I would be using the precious time alone to indulge in my secret addiction. I kissed her on the cheek and said goodbye as we both got into our cars and drove off. I did my usual trick of driving round the...Read On

24

Crazy Sex Affair With Her Sister

Finding a girl who shared my love of lingerie.

My girlfriend Lisa and I met at a club when both fairly drunk. She came home with me and we fucked on the first night. It was nothing special but she was desperate to get with me and would put out anytime I wanted, so we carried on dating for a few weeks. The sex was ok, mainly because she would do whatever I wanted, including fulfilling my fetish by dressing up in lingerie and heels every...Read On

10

The Pool Man

I fucked the pool man

It had been several months since I moved away from the big city. It was hard moving to a city with not a lot of people I could hang out with or be with. I had become really good at dressing up and having anal sex, but was becoming more and more restless of not having a regular, daily thing with someone.  I began fantasizing about being with the pool man. He was always friendly when he came...Read On

9

My First Experience With A Man

My first experience with a man and he made me crossdress

It happen when I was 18 years old. I was working for a clothing company at the time and it was a slow Tuesday morning. As I was folding clothes, a tall (I’m 5’5 he was 6’2) light skinned black man approached me. He introduced himself as Sam. He looked like he was well into his forties but was really fit. He inquire about several clothing articles in our store and slowly the conversation...Read On

11

Dan into Danni pt3: Sex as a girl with a girl

Lucy gives Danni the best orgasm of his life... as a girl.

Back at Lucy’s room, Dan put down the dainty bags of lingerie and girly clothes that she had bought for him. He had been totally and magically transformed into a girl for nearly a whole day now, and every moment was a thrill. He was ultra-conscious of his body - especially his gorgeous 32C boobs, firmly held in the bra that had turned him into a curvy and sexy girl in the first place. ...Read On

7

Seeking a Greater Perfection

A young transvestite tries to navigate the challenges of a real life relationship with a man

I was on personal display for him. He would have me walk sensually while emulating the grace of a pretty blonde haired runway model. In my role of girlish temptress, I wiggle my sexy bottom in my exotic, six inch pink, high heeled, platform sandals. My body is slim, lithe, feminine and smooth. At the far end of his large living room he has me turn around, smile, and pose like a show girl...Read On

23

The House Sitter

Francis has an interesting twist to his house sitting week.

“Okay, that covers everything I think! Thanks so much for this, Francis. I know it was short notice but I really appreciate it,” said Ms. Wilson. “And remember, please, please, please help yourself to anything in the house.” “Oh, it’s not a problem. Just hope you have fun on your cruise!” I couldn’t help but wonder why she was going on a singles-only cruise for a week. She was hardly...Read On

7

Dan into Dani Part 2: Getting used to girlhood - lingerie shopping

Buying lingerie is challenging for new girls, especially if they're really boys.

OK, Dani, take off my knickers, choose a fresh pair from the drawer, and let’s get you dressed,” said Lucy. Dan sat up in bed. He was wearing a tight-fitting white bra and Lucy’s knickers - the ones he had pulled down Lucy’s legs before he had plunged his throbbing cock into her wet and inviting cunt. The night before. When he had been a boy. Now everything had changed. He had been...Read On

13

The Foreigner

His accent was strong, but his hands were stronger.

I had been chatting online with him for a while now, and he was keen to meet me. He identified as straight and was married, which is normally a deal breaker for me, but he was persistent. After a lot of chatting, I agreed to meet him at his place. When I arrived, he buzzed me into the building, and I went upstairs to find he had left the door ajar for me. Nervously, I went in. His place was...Read On

10

The postman

Lucy gets a delivery from the postman that was a bit more than she expected.

Lucy was in her man mode at home when she heard a knock at the door. She answered it and it was the postman delivering a couple of packages for her. They were full of sexy lingerie and three sexy dresses. The postman came inside her hall to talk. The postman had obviously found out what was inside the bag. “I’m sorry, but one of the bags broke so we had to repack it for you.” ...Read On

7

Mall Walking

I must see up her skirt!

I recently sighed a contract with an online Mistress. My main duty under the contract is to write or edit several publications I'm preparing for sale. If I displease her, she assigns me essays - writing of her choosing that doesn't contribute to my writing goals. I sent her a late response and she assigned me to write about a man following a woman in a mall because of her sexy pencil...Read On

5

Realized Fantasies. Chapter 2, part 1: Steffie Sucks

Crossdresser Steve/Steffie is blackmailed by coworkers into servicing their cocks.

Steve, or Steffie, was fearful of delaying too long in the bathroom, so, shaking his head, he picked up the panties and pantyhose left on the counter for him. He discovered that the pantyhose were crotchless, and considered putting them on first, since his panties could then be removed easily. But he decided that the guys were likely not interested in his own pleasure, so he donned the...Read On

17

Stephen and Stephanie

A young man's journey through cross-dressing, femininity and sexuality

As neighbors, Carol, Karen and I regularly met up on weekends during school term and more often during the holidays. We played many games together, and I happily joined in, despite their girly nature; I even played with dolls. Of course, the kids at school found out about this, and I was bullied mercilessly for being a sissy. I tried to explain that no boys were living nearby to play with,...Read On

11

Who is Bella? - Part One

Velda struggles to know if her boyfriend is what she really wants

It all started after a couple of week’s dating. I was nineteen at the time, and Velda was twenty-four. I knew she had strong opinions and was quite determined to get her way. She had spoken several times about women’s rights and how she felt that the balance of power between men and women had to change. For the most part, I could only agree with her. At times she seemed a little aggressive...Read On

20

Caught

It seemed to Ken that time had slowed down to a snails pace as he watched the events unfold before him. The door to his sister's bedroom seemed to take forever to open and for Connie to step inside. Connie's head was down as she placed something in her purse before it rose up. That act also seemed to take forever as did her eyes growing wide as she took in the scene in front of her. Ken...Read On

13

A Condition of Endearment

A Transvestite Finds Harmony in a Big City

I am a young, petite, passable and enthusiastic transvestite. I’ve been crossdressing and working on improving my look and appearance ever since I was a sixteen year old boy. Now after two years of weekends dressed in public as Cari, I had developed quite an attractive look and appearance. It often seemed at times, that many a man would come my way. Because of my exotic and sexy...Read On

10

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

3

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

9

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

13

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

19

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

15

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