Crossdressing

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: 4.29 | Tags: mm  blowjob  bj  roommates  marines  uniform  crossdressing   | 6 Comments

rea123

My wife is the man and I am the woman at home

My wife has me dress as a woman while she plays the man

I had been interested in cross-dressing in the past and my wife knew it but she never really was interested in it. This was in a way surprising to me since she always was aggressive in her corporate career and always wore men's clothing, jeans, boots, tee shirts, and so on outside of work. I on the other hand always preferred to dress as nicely as possible both at home and work. Wearing soft...Read On

Added: 03 Dec 2012 | Category: Crossdressing | Avg Score: 4.64 | Tags: crossdressing  wife  strapon   | 11 Comments

LoriAnn_CD

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

Added: 01 Dec 2012 | Category: Crossdressing | Avg Score: 4.86 | Tags: oral  bi  anal  couple   | 2 Comments

LoriAnn_CD

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

Added: 30 Nov 2012 | Category: Crossdressing | Avg Score: 4.67 | Tags: anal  oral  bi  couple   | 2 Comments

LoriAnn_CD

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

Added: 28 Nov 2012 | Category: Crossdressing | Avg Score: 4.67 | Tags: anal  oral  group   | 5 Comments

LoriAnn_CD

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

Added: 27 Nov 2012 | Category: Crossdressing | Avg Score: 4.75 | Tags: oral  anal   | 5 Comments

LucyandBelle

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

Added: 23 Nov 2012 | Category: Crossdressing | Avg Score: 4.6 | Tags: crossdressing  sub  dom  girlfriend  lesbian  threesome  anal   | 1 Comment

LucyandBelle

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

Added: 22 Nov 2012 | Category: Crossdressing | Avg Score: 2.6 | Tags: crossdressing  sub  dom  girlfriend  lesbian  shower  pissing   | 4 Comments

LoriAnn_CD

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

Added: 21 Nov 2012 | Category: Crossdressing | Avg Score: 4.67 | Tags: crossdressing  oral   | 3 Comments

jerrixdresser

My Night at the XXX Video Theatre - Part One

My adventure in a bad part of town at an XXX Video Theatre

It was almost 2 AM when I pulled into the Big Town XXX video theatre in the southeast part of where I live. It was a Saturday and the parking lot was full. I had never been to this particular theatre but it was in the adult theatre chain that I had been visiting for the past two years. Each theatre is different depending usually on the part of town where it is located. Southest part of my...Read On

Added: 21 Nov 2012 | Category: Crossdressing | Avg Score: 4 | Tags: crossdressing bimbo  xxx video store     | 2 Comments

LoriAnn_CD

Becoming LoriAnn part 1

a boy becomes the girl he always wanted to be

I had two old sisters and spent many hours borrowing and dressing up in their beautiful clothes. I loved the soft texture of their panties and bras, the silkiness of their nighties and the tightness of their pantyhose. I especially loved feeling sexy in their miniskirts and tops that revealed just a little bit of my chest. I would dress up and wish I was a cute girl. One day it happened,...Read On

Added: 20 Nov 2012 | Category: Crossdressing | Avg Score: 4.59 | Tags: girlieboy   | 7 Comments

Ginna_CD away

Family Friend Outing

A family friend fucks me after outing myself to him

A few years ago I went back home to Greece for Easter to see my folks and enjoy a bit of the sun. My folks live in a small town where it’s impossible to get any cock if you are not out. As any typical small town where everyone knows everyone, coming out to a few people becomes coming out to the entire town after a few days. So naturally I spent most of my time gagging for cock in silence. ...Read On

Added: 17 Nov 2012 | Category: Crossdressing | Avg Score: 4.88 | Tags: passive  anal  cd  crossdresser  fucked   | 9 Comments

NatureLover

Afternoon Delight

Hot afternoon session with two gorgeous ladies

I was stuck in the office on a pleasant sunny day in late summer, daydreaming about the afternoon of delight that lay ahead of me; I was meeting up with my lover, Kate, later that day. Kate is a girl I have been friends with now for a number of years, we met through some mutual friends and hit it off straight away. We are both in relationships of one kind or another but we are good together...Read On

Added: 16 Nov 2012 | Category: Crossdressing | Avg Score: 4.79 | Tags: crossdressing  lingerie  threesome  strap-on anal     | 6 Comments

jess_xo

Motel Fun for College Crossdresser

A young college student enjoys a girly getaway at a nearby motel.

Before I start the story I want to describe the setting so you get a better idea: it's a highway side motel, very rundown and not very cleanly, not a dump either but not the best place to have a family sleep that's for sure. The layout of the motel is a rectangle. The rooms surround the rectangle's perimeter, in the center there is a pool, a park area, and a parking lot. There is a...Read On

Added: 04 Nov 2012 | Category: Crossdressing | Avg Score: 4.59 | Tags: crossdresser  motel     | 11 Comments

cdbottom2

Telling Mom I'm A Cross Dresser part 18: Missy's Halloween Party

Part 18 is about halloween. Hope you all enjoy despite i was a little rushed for this one.

I had enjoyed my week of sex with Thomas and Lemar but in the end it left me sore and used but not like I was complaining. It was now getting close to Halloween and mom and I were making plans to go to a Halloween party a few city blocks away from us. Yeah, sounds kind of boring I know but it was no ordinary party with costumes and drinking alone. It was an orgy for bisexual people. It...Read On

Added: 31 Oct 2012 | Category: Crossdressing | Avg Score: 4.56 | Tags: orgy  gangbang  bisexual  halloween  milf  toys  oral sex   | 3 Comments