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Crossdressing

28

Vanessa Goes All the Way

A few months after having my first date, I was feeling kind of anxious about not really allowing myself to go further. I had plenty of guys interested, but I wasn't really ready to make that move. I had been talking to this sexy college boy for a few weeks, but we couldn't set up anything solid. We finally nailed down a date, but he had some last minute issue come up, and had to cancel. I...Read On

15

Vanessa's First Date

This is a memoir of my first time meeting a man. I'd been crossdressing for many years. I had many fun nights dressing up and playing with my toys but I wanted something more. I liked to get on the phone with guys and play around. I had my favorite toys to use, especially my eight inch dildo and my butt plug. I really got into my phone sessions, but I felt like I wanted to go further. ...Read On

25

Dave and I

Dave called and asked me to go out with him on Friday

This is a work of fiction. Any resemblance to any person living, or dead is purely coincidental. Later that day we sat at the table talking about the events of the past evening. The phone rang. It was Dave on the phone. He wanted me to go out with him on Friday and he wanted me to dress sexy..  I had been with Dave only one time; it was at my anniversary party. My wife arranged everything....Read On

13

Stacy's First Time

I loved tasting his warm cum.

I have been cross-dressing for almost a year now. Ever since I can remember, I have had a fetish for high heels and finally was able to start buying my own secretively once I came to college. I have my own collection and wear feminine clothing mostly in my room, but one evening I was so horny from watching porn and wearing my dress and heels. I went on to an internet site to find someone in...Read On

33

Wife's crossdressing fantasy Part 3

I had to find a way to repay my wife for the wonderful anniversary gift she game me.

This is a work of fiction. Any resemblance to any person, or incident is strictly coincidental. My Wife's Cross dressing Fantasy 3 Then my wife looked at me and said “Happy anniversary darling.” How did she know the effect this experience would have on me. I was changed forever. It was such a wonderful experience. She deserved that I come up with something just as exciting for her,...Read On

7

Master's Reminder

I had been seeing Master John for about a year now and thing’s were going well or so I thought!

I had been seeing Master John for about a year now and thing’s were going well, or so I thought. I arrived at his home like any other weekend in the outfit he wanted me to wear for my punishment. He would always choose the week before and I knew that there was no argument whatever he wanted he got. I hoped that I had got everything just right for him. Anything slightly out of place or...Read On

35

The Awakening of Susi

Susi discovers the joys of anonymous cock sucking at a glory hole (true story)

Ever since I can remember I have loved being feminized and being made to wear very slutty clothing. This is a true story of my first experience at a glory hole and a coming of age for my sissy self. I had many female friends who loved to dress me up in their sexy clothes and strut me around in front of their boyfriends. They thought it was cute to see me in full makeup and a wig wearing a...Read On

8

Big Green

Loosely based on true events and it is my first story so please be easy. Being a Marine for most meant traveling, working out and above all alpha males only. For me all of this was of interest but I didn't work out and I was definitely not an "Alpha Male". Slim in stature I stood all of five foot, six inches weighing in at a whopping 145 pounds. I wasn't much to look at in a uniform but out...Read On

17

becoming LoriAnn - Part 6

Last minute preparations for our night with her husband Max!

Nikki and I got together one more time before we set her plan in motion. We had to make sure we were on the same page, that Max would have the ultimate night of his life and we had to spice up Nikki's wardrobe. Nikki was a beautiful woman, slim and sensuous, but a bit conservative in her dressing. So we made a date to go shopping. We started at Victoria's secret. We bought contrasting...Read On

10

Becoming LoriAnn - Part 5

Lori goes out for her first assignment and tries something new

I was now a full time working girl for Walter and I had been given my first assignment. Walter explained that I would be spending time with a couple. It seemed that this couple had decided to add some spice to their sex life by having a few threesomes. It began with the husband, wife and another woman. The second and the third time were the same except with a different woman. And while...Read On

12

Becoming LoriAnn - Part 4

LoriAnn has found hereself as a cock sucking, cum slurping, anal whore

I started seeing Walter, my friends uncle, about every other day and every other day was a sexual adventure. I was a cock loving, cum slurping whore in training. Soon I moved in with him and he had his way with me every day. All I was allowed to wear was a bra, a thong and stiletto heels. I was to have my hair done and full make up everyday. When expected I was to fall on my knees, suck...Read On

9

Becoming LoriAnn - Part 3

LoriAnn takes another step towards becoming the slutty gurl she wants to be

I was enjoying my new found sexual freedom. My first steps were slow and easy but nothing felt more exciting than discovering the feel and taste of a new hot, hard cock. The boys at school never really bothered me about regular sex and long as they got to shoot their big hot creamy loads down my throat or all over my tits, and I was happy each time I was able to swallow one of those...Read On

6

Belle brings back a girl

Belle goes on a drunken night out and brings a girl home to share with Lucy

Lucy was lazing around in the living room when she heard Belle drunkenly try to scrape the key in the front door's lock. She heard giggling - a second voice. A woman's. Lucy put her tattered copy of Asimov's Second Foundation down on the coffee table and owled the door with interest, her nylon legs sprawled across the arm of the sofa. Lucy and Belle were both avid readers. Between them...Read On

7

Mistress Lucy takes control

Power reversal; the usually sissy crossdresser Lucy has fun with her girlfriend, Belle.

Belle had finished disrobing and stood in her bra and thong, both pink, following Lucy's command. The latter stood in front of her girlfriend and, with a light touch of the shoulder, pushed Belle down on to the bed. Belle looked up at Lucy expectantly, eyes wide. Neither girl wore any makeup; they'd been awake for a couple of hours and, having spent the morning in the kitchen loafing around...Read On

15

Becoming Lori Ann - Part 2

Lori Ann learns some new tricks

The more I thought about the warm milky cum dripping down my hand the more I knew I wanted more. My sisters continued to take me to parties as their cousin and they enjoyed seeing me having fun with the boys - mostly jerking them off - but I wanted more. I wanted to meet boys on my own and more than anything I wanted to taste a rock hard cock. I convinced my mom that it was time for Lori...Read On