Crossdressing

CourtneyFux

Club Night

Wearing my sexy minidress out to the club, I give the boys lots of thrills.

I hadn't been at the club very long when he came over to me: a very handsome man, tall with dark hair and blue eyes. "You have a perfect ass," he said. I was wearing a sexy, little minidress which barely covered my ass and I knew it would turn men on, but I didn't know it was going to happen this quickly. I smiled up at the tall stranger. "I'm flattered," I said. "I'd like to pull up...Read On

Added: 18 Feb 2013 | Category: Crossdressing | Avg Score: 4.76 | Words: 4,612 | Tags: crossdressing  exhibitionism  oral  anal   | 4 Comments

kylie_kained

In Her Shoes Part 2

This is the second part of In Her Shoes so to fully understand what’s gone on

please read the first part. After a short time of resting my feet on Peter’s bum I now slipped my foot back rubbing the sandal against his balls and cock. His knees started to widen slightly as I teased I could see his balls quickly rise up and tighten as they had before. His cock was now straight along my foot and his body was rocking back and forth in time with my foot. I could feel...Read On

Added: 07 Feb 2013 | Category: Crossdressing | Avg Score: 4.75 | Words: 1,770 | Tags: crossdressing  fetish  foot  shoe worship  first time  dominant  submissive   | 2 Comments

Adagio

From One To Another-Part 2

two sides of a chair

I rushed into my new consignment shop job, the one that Allison had help me get. The shop was actually a duplex. One part Mary's home, the other her shop. I was a few minutes late and apologized to Mary Elle the owner. Telling her that my Biology teacher was on my case about missing assignments and had kept me after school.  Mary Elle looked at me and suggested a nice warm shower to help...Read On

Added: 01 Feb 2013 | Category: Crossdressing | Words: 960 | Tags: fisting  enema   | 6 Comments

CourtneyFux

Porn Star Babe: Part Two

Time to get the lttle sluts on the set for some hot tranny action.

Being a sexy girly boy about to make her debut as a porn actress with two handsome, well-hung studs was so exciting to me. And having my friend, Chrissie Licks, along to show me how it is done was especially re-assuring. Chrissie and I were naked and about to get into our sexy lingerie for the shoot when Summer Cox, another hot tranny porn star, came to help us with our hair and make-up....Read On

Added: 31 Jan 2013 | Category: Crossdressing | Avg Score: 4.22 | Words: 2,569 | Tags: crossdressing  exhibitionism  oral  anal  group sex  bisexual   | 3 Comments

jessicahahn

Sissy at the Bookstore

Or how I humiliated myself in drag

I had gone to adult bookstores for many years and had done it in drag many times but never dressed as a sissy and never during the day. On this day I was so involved in humiliating myself that I decided that I need to take that extra step and I did. I had checked into an adult motel the night before and booked for two days so I had a lot of time on my hands. The night before I had pranced...Read On

Added: 29 Jan 2013 | Category: Crossdressing | Avg Score: 4.69 | Words: 1,500 | Tags: crossdressing  sissy  gay  exhibition  fetish.   | 13 Comments

CourtneyFux

Porn Star Babe: Part One

Making her first porno movie, Courtney discovers all the pleasures of being a porn star.

As a hot, 20 year-old girly boy, I was invited by another girly boy to star in a porn movie with her. It sounded fun and I was adventurous sexually, anyway. So, becoming an actress getting lots of big loads of cum from her handsome co-stars was very exciting to me. The movie was shot in a private house where I drove to with my girlfriend, Chrissie Licks, a pretty, 21 year-old, aspiring...Read On

Added: 28 Jan 2013 | Category: Crossdressing | Avg Score: 4.58 | Words: 2,553 | Tags: crossdressing  exhibitionism  oral  anal  group sex  bisexual   | 6 Comments

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 | Words: 1,412 | Tags: crossing dressing  transexual  piercing   | 6 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: 4.79 | Words: 3,151 | Tags: crossdressing  bisexual  anal  cunniligus  blowjob  exhibitionism  threesome   | 8 Comments

CourtneyFux

A Panty Boy in Paradise: Part One

Being an escort for men leads to new sexual adventures for Courtney.

I wasn't sure how it was going to go. My new client hadn't given me any specifics. But I was excited about the glamour of being on a yacht with a rich older man and his young crew. We would be sailing for the weekend to the Bahamas and I would have my own cabin to sleep in and take naps during the day. All expenses, including the lingerie and bikini bathing suits I would wear, were paid for....Read On

Added: 24 Jan 2013 | Category: Crossdressing | Avg Score: 4.5 | Words: 6,459 | Tags: crossdressing  oral  anal  voyeurism  exhibitionism  group sex  bi-sexual  

kylie_kained

In Her Shoes

I opened my online mail box as usual, looking down the list in case any new spam was in amongst the thirty-seven mails I had received. As I scrolled down the page I noticed a new mail from one of the sites I used to find new partners for sex. I clicked it open straight away not wanting to waste any time, hoping that this mail for once was from someone more sane and rational than the usual,...Read On

Added: 24 Jan 2013 | Category: Crossdressing | Avg Score: 4.95 | Words: 2,590 | Tags: crossdressing  fetish  foot  shoe worship  first time  dominant  submissive   | 9 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: 4.45 | Words: 1,308 | Tags: crossdressing  masturbation  phonesex  toys  anal   | 5 Comments

CourtneyFux

Born To Be A Babe: Part Two

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 girl and I wanted to wear...Read On

Added: 09 Jan 2013 | Category: Crossdressing | Avg Score: 4.98 | Words: 12,984 | Tags: crossdressing  exhibitionism  oral  anal   | 19 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: 4.67 | Words: 1,866 | 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: 4.86 | Words: 1,638 | Tags: cross dressing  father  son  mm  bi sex  oral anal   | 18 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: 4.79 | Words: 1,970 | Tags: strapon  panties  femdom  feminization  sissy  anal   | 10 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: 4.63 | Words: 918 | Tags: crossdressing  anal sex  oral sex  first time   | 9 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: 4.38 | Words: 631 | 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: 4.82 | Words: 2,388 | Tags: crossdressing  oral  anal  mm   | 11 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: 4.08 | Words: 633 | 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: 4.76 | Words: 6,119 | Tags: crossdressing  oral  anal  group sex   | 16 Comments

kylie_kained

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: 4.25 | Words: 1,573 | Tags: crossdressing  oral sex  water sports  humiliation  strangers   | 2 Comments

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: 4.83 | Words: 1,900 | Tags: glory hole  sissy  crossdresser  submissive  cum dump  exhibitionism  public sex   | 14 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: 4.25 | Words: 702 | Tags: mm  blowjob  bj  roommates  marines  uniform  crossdressing   | 6 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 | Words: 3,026 | Tags: crossdressing  sub  dom  girlfriend  lesbian  threesome  anal   | 2 Comments

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: 3.29 | Words: 1,049 | Tags: crossdressing  sub  dom  girlfriend  lesbian  shower  pissing   | 4 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 | Words: 887 | Tags: crossdressing bimbo  xxx video store     | 6 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: 4.67 | Words: 4,259 | Tags: crossdressing  lingerie  threesome  strap-on anal     | 7 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: 4.56 | Words: 1,682 | Tags: crossdresser  motel     | 19 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: 4.73 | Words: 4,039 | Tags: orgy  gangbang  bisexual  halloween  milf  toys  oral sex   | 3 Comments

CourtneyFux

Two Girls Are Better Than One

My girlfriend sets me up with other men we share.

My girlfriend, Sherry, had nice, big C-cup titties and a face like a young Marilyn Monroe. Needless to say, she got hit on by lots of men wherever she went. She was also a nyphomaniac who liked to be fucked ten times a day, so we had a great sex life. She found out I enjoyed wearing lingerie, so, as part of our sex play, she would dress me up in her panties and bras and stockings and...Read On

Added: 31 Oct 2012 | Category: Crossdressing | Avg Score: 4.81 | Words: 10,720 | Tags: crossdressing  exhibitionism  oral  bisexual   | 7 Comments