Crossdressing

adagio

From One To Another

a woman is born

I was raised by my aunt due to unknown circumstances in my life. Although she was puritanical and strict I loved her. She had some rules for me. For example, I needed to say Grace before every meal and go to church every Sunday. I needed to read the scriptures on a daily basis and she monitored the TV shows I watched. I was not allowed to listen to modern music or read magazines. This...Read On

Added: 26 Jan 2013 | Category: Crossdressing | Avg Score: 4.28 | Tags: crossing dressing  transexual  piercing   | 3 Comments

biguy2play

Always Up for a Party

Trevor's idea of a party, with me as entertainment

I got home late. What a night! I had gone to the video booth at the bookstore horny as hell but in my wildest dreams I could not have imagined the outcome. Oh sure, I expected sex. I had yet to leave those dark little booths without a mouthful of cum, an ass full of cum or having my balls sucked dry but tonight … tonight! Not only had my ass been filled in the booth but at Trevor’s party...Read On

Added: 25 Jan 2013 | Category: Crossdressing | Avg Score: 4.88 | Tags: crossdressing  bisexual  anal  cunniligus  blowjob  exhibitionism  threesome   | 6 Comments

vanessagrrl

Vanessa Spends a Night Semi-alone

One night I was laying around bored, so I decided to get all sexied up for no one but me. I got out one of my favorite outfits, which you can see in my picture. I was so excited as I undressed, and laid everything out that I was about to slip on. First I put on my sexy Victoria's Secret thong. It was white with black lace, and it felt so hot as it slid on. Then, I put on the matching bra. It...Read On

Added: 14 Jan 2013 | Category: Crossdressing | Avg Score: 4.38 | Tags: crossdressing  masturbation  phonesex  toys  anal   | 7 Comments

CourtneyFux

Adult Bookstore in My Hot Pants

Wearing a sexy pair of hot pants, I go looking for men at the adult bookstore.

After discovering that I enjoyed wearing sexy little panties, tasting cum and having a big vibrator in my ass, I began to have these auto-erotic sessions, every day.While wearing panties and playing with my ass with a dildo, I would lay in my bed and fantasize about all the big cocks I wanted to satisfy for men. While I was only 16 years-old, I had decided I was a daddy girl's and wanted to...Read On

Added: 09 Jan 2013 | Category: Crossdressing | Avg Score: 5 | Tags: crossdressing  exhibitionism  oral  anal  incest   | 9 Comments

CourtneyFux

The Sexy Secretary Gives at the Office

Working as a tranny escort, I get dressed up as a sexy secretary.

Working as a tranny escort is my favorite way to earn money and get lots of cock, at the same time. I love to put on sexy panties and show off my body to men, so it is a job I enjoy doing the most. The fact that lots of men really like me and call me back again and again makes me feel wonderful, as well. I have long hair that makes me look like a woman from behind and my breasts are big for...Read On

Added: 07 Jan 2013 | Category: Crossdressing | Avg Score: 4.88 | Tags: crossdressing  exhibitionism  oral  anal   | 6 Comments

BiUKSwinger

My First Time with a cross dresser

Introduction to crossdressers

Growing up, like many children I went through phases. I would climb trees and play football, then as I reached my mid-teens I continued these phases but also became a lot more sexually aware, thanks to the porn magazines and porn films usually belonging to my mates dads or older brothers. Now I am in my late teens and at college. One day my Dad made a pot of tea and breakfast.“Did you...Read On

Added: 06 Jan 2013 | Category: Crossdressing | Avg Score: 4.87 | Tags: cross dressing  father  son  mm  bi sex  oral anal   | 15 Comments

libertina

The Perfect Choice

A girl works to turn her boyfriend into her toy

Andrew had moved in with Hannah a few short months ago and so far everything was going just the way she wanted. She was an endless tease; wearing short skirts and dresses when they were out during the day or tiny shorts and vest tops when they were at home together. She did everything she could to turn Andrew on, and it was working perfectly.She hadn't slept with him yet and the tension...Read On

Added: 05 Jan 2013 | Category: Crossdressing | Avg Score: 4.78 | Tags: strapon  panties  femdom  feminization  sissy  anal   | 7 Comments

vanessagrrl

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

Added: 03 Jan 2013 | Category: Crossdressing | Avg Score: 4.67 | Tags: crossdressing  anal sex  oral sex  first time   | 8 Comments

vanessagrrl

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

Added: 02 Jan 2013 | Category: Crossdressing | Avg Score: 4.62 | Tags: crossdressing  mm  handjob  hotel   | 8 Comments

Km44

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

Added: 23 Dec 2012 | Category: Crossdressing | Avg Score: 4.77 | Tags: crossdressing  oral  anal  mm   | 11 Comments

dougysweet

First Time Fantasy

Fantasy - The Dom, the sub and the bi-virgin After all these years of being in the closet, I finally believed that it was time to move from fantasy to reality. Years have gone by of me wanting more but not being ready to step out and experience things for myself. My stockings ran and my lingerie started to collect and time and time again, I purged and replaced more than one collection...Read On

Added: 14 Dec 2012 | Category: Crossdressing | Avg Score: 4.85 | Tags: fantasy  crossdress   | 9 Comments

stacyarthur85

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

Added: 12 Dec 2012 | Category: Crossdressing | Avg Score: 4 | Tags: first time   | 4 Comments

Km44

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

Added: 10 Dec 2012 | Category: Crossdressing | Avg Score: 4.82 | Tags: crossdressing  oral  anal  group sex   | 8 Comments