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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.

17

In and Out of the Closet

A Young Man Gets Caught Inside His Employer's Walk-in Closet.

I had just turned eighteen when I started gardening for a young couple in their early thirties. The Shelby’s were quite well off, living a large four-bedroom house with both a swimming pool and a tennis court. Both were good-looking too. I had observed them playing tennis just the day before. She was a little blonde bombshell with light blue eyes and a terrific body, ample boobs, and...Read On

24

The Compromise: Part 1

A suggestion from a counselor sets in motion a fantasy compromise that changes my life forever.

My wife, Ally, and I have been married for eight years. What once could be considered a torrid love affair had subsequently lost its sexual passion. We don’t have any children, both being career focused, but our sex life had become quite stagnant from the steady grind of life and over-familiarity we had with one another’s sexual tastes. That is, until one crazy night changed everything. ...Read On

20

Curious No More

I used to call myself bi-curious, but now I know!

I began dressing in my sister's clothes. I would get so hard and excited when I felt the soft panties against my cock and the bra wrapped tightly around me. But my dress up time was always short. Now that I live on my own I have my own femme wardrobe and plenty of time to dress and perfect my makeup and appearance. The more I dressed and the longer I stayed dressed, the more I wondered what...Read On

31

Confessions of a Ladyboy - Part 1

He helps me resolve my boy/girl confused sexuality dilemma

I was eighteen and new in the boy's hostel. No one had wanted me at home. I had never known my father. I saw my mother go out with a different man almost every night ever since I was old enough to remember such things. She taught me some valuable lessons - how to be attractive, how to carry myself, how to be seductive, how to do my makeup. She always said, "You are such a cute boy, you...Read On

12

Jenny and Mike: Date Night

A loving husband and wife begin a long weekend of crossdressing and pegging.

It’s Friday night, but for me and my wife it’s Date Night. Most couples have date nights on Saturday, but we have it on Friday nights to get an early start on the weekends. Michelle and I have been married for a little over two years now and we live a very happy life. I was not always so happy because I am a crossdresser and have been dressing up ever since I was 16. I met Michelle when we...Read On

5

Jenny & Mike: A Day out

Role Reversed day of shopping, a dinner date and pegging at the movie theater.

I woke up in the morning with Michelle’s arm around me. We were spooning. She was the big spoon. I held on-to her arm stroking it gently as I recalled how ‘Mike’ and I had gotten it on in the living room the previous night. ‘Mike’ had fucked me on numerous occasions in the past, but my ass was still sore after what we had gotten up-to last night! God it was so hot! I turned my head to look...Read On

4

slut on the town

I got put in a full nelson the other night by a naked black guy. It happened in a video preview booth at Corey's Adult Video store in Oakland. I had been hanging out in the arcade, wearing just a black two-piece string bikini, and a pair of fire engine red high heels. I had been there for about a half hour, but I hadn't seen anyone. But it was early, only 3.30 p.m. Then I heard the buzzer go...Read On

7

One On the Way. Part 1

A new plan was required if he wanted to see Vicki.

Darren had met Vicki through Charlene, one of the girls from his school. He had just attended a Saturday movie matinée and was waiting for the bus to take him home when they walked up. Apparently, they were there too. From the moment they were introduced and locked eyes on each other, there was an instant attraction. He mentioned that he was surprised that he had never seen her in the...Read On

6

Jessie's Path

A true story of the Path that Jessie took.

One’s path in life has three primary sections. The first one is what made a person who they are. Everything from their parent’s genetics, to how they were raised, the environment they grew up in, and any uncontrollable outside influences causing a life changing event. The second section of the path is what we see, feel, hear, taste, and touch at this very moment in time. It is a collection...Read On

10

A Night of Firsts pt 1

So many firsts for a shy gurl while traveling

'Oh my God, this was the night,' I thought to myself. 'I'm finally going to go out dressed.' I work for a small company and get to travel a bit, but I've really only dressed in hotels when I could drive as flying with all my things makes me really nervous. The idea of me and a travel bag being examined and having a stranger discover my femme things just didn't do it for me. However, this...Read On

9

Discovery Part 2

It had been an amazing year for Kyle. At eighteen he attended his first get together for those that cross dressed and their supporters. It the first time since the urge to dress up came upon him he finally felt safe and accepted. Over the following months, he perfected his skills at makeup along with dressing, walking and talking like a female. Soon he was one hundred percent passable in...Read On

8

One On The Way Part 2

In Vicki's Room

Darren could only stare dumbfounded at Vicki's statement. He watched her slid off the bed and head to a tall narrow chest of drawers across the room. Darren admired her firm backside and slender legs as she bent to pull out a couple of the lower drawers and look inside. Vicki finally returned to the bed and handed him a few folded items. "You're dressed for the streets, but you need to...Read On

3

Jenny & Mike: Fantasy Sunday

A day of fantasy role-playing with more crossdressing and strapon action.

MICHELLE’S POV The alarm was buzzing, and I couldn’t understand why. We never set it to go off on Sundays. I tried to open my eyes as best as I could. It was only 9 a.m.! I reached over and tried to shut the darn thing off. After a couple of failed attempts, I finally found my target. The awful noise stopped. I turned around realized that James was no longer in the bed with me. “James?” ...Read On

4

Jessie's Fantasy Chapter 8: A New Beginning

Jessie finishes having fun with her male friends, So what does Tracy have in store for her?

I sat in stunned silence after the love of my life gave up my little secret to all of my friends. After losing a bet with John, I had to dress up as a woman and try to hook up with a guy as payment. Tracy and her friends did such a good job making me look like a woman, that I was able to fool all of my friends into having unplanned, but very much enjoyed, sex with me. It wasn’t until Ross...Read On

5

One on the way. The Conclusion

Darren heads home.

Once inside the bathroom, Darren removed the silky nightie and handed it to Vicki. He cleaned up as much of the puddle of cum in his panties as he could before he redressed. Once again he slid up the short tight skirt up and donned the silky blouse and padded bra. He grabbed the pantyhose Charlene had loaned him and opened the door. He found Vicki waiting for him when he exited. She was...Read On