Crossdressing

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: 4.89 | 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: 4.81 | 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

kyliekained

Twisted Fate

A birthday present I don't think I will ever forget.

My birthday was on the Wednesday that week so it would mean that any celebrations would have to wait for the weekend. I got the usual cards and a few presents from my family and friends but the present I always looked forward to the most was the one that Julia my wife always gave me in private before bed and away from prying eyes. That night as we got into bed Julia gave me a neatly...Read On

Added: 03 Jan 2013 | Category: Crossdressing | Avg Score: 4.74 | Tags: crossdressing  bdsm  group sex  oral sex  cuckold  riding crop     | 6 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

rea123

Switching roles

This story is fiction but based on my reality.

I guess you could say my wife and I always made kind of an unconventional couple. I am almost six feet tall and blond haired. My wife is about five and a half feet tall with magnificent tan skin and shiny black hair. I work out of our home as a graphic designer. She is a high powered executive at a stock trading company. Nevertheless we fit each other perfectly. I loved how hot she looked...Read On

Added: 23 Dec 2012 | Category: Crossdressing | Avg Score: 4.87 | Tags: crossdressing  wife  strap-on   | 7 Comments

rea123

My wife loves dressing me as a woman

My wife buys me beautiful women's clothing to make me look feminine for her

After a long day at work I was relaxing just reading a book. My wife wasn't home so I just stayed in my work clothes. She had decided a while ago that we were going to switch sex roles at home, but I still kept a full men's wardrobe for work. After a few hours she came home. Bringing a big shopping bag into our bedroom she said, "Come here honey, look what I bought for you." She emptied the...Read On

Added: 16 Dec 2012 | Category: Crossdressing | Avg Score: 4.67 | Tags: crossdressing  wife  strapon   | 4 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: 4.85 | Tags: crossdressing  oral  anal  group sex   | 8 Comments

kyliekained

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

Added: 05 Dec 2012 | Category: Crossdressing | Avg Score: 4.43 | Tags: crossdressing  oral sex  water sports  humiliation  strangers   | 1 Comment

susi_swallows

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

Added: 05 Dec 2012 | Category: Crossdressing | Avg Score: 4.82 | Tags: glory hole  sissy  crossdresser  submissive  cum dump  exhibitionism  public sex   | 11 Comments

CAPITALLETTERJ

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

Added: 05 Dec 2012 | Category: Crossdressing | Avg Score: 4.33 | Tags: mm  blowjob  bj  roommates  marines  uniform  crossdressing   | 6 Comments