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Crossdressing

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10

My feminine Urge Satisfied

My feminine urge took me to a new level at transforming myself into a sexy woman.

I had a three day weekend for me to dress en-femme, and so I took advantage of it. I was not looking to do anything other than dressing, behaving, and acting as a woman. I was content to just relax and be feminine at home without any expectations. I don’t know why I felt as such, except that I needed just to enjoy being feminine and doing so alone. With that in mind, when I got home...Read On

10

Memories

Reminiscing about time spent before dating

Just for fun, I though it might be nice to share some of the experiences I went through on my way to becoming the sexy slut I am. Before I had the confidence to fully dress and go out, and to go on the few dates I've been on, I was completely closeted. The only way I could express my girly side was through playing on the phone and all alone. I loved dressing up a few times a week. I...Read On

16

Lisa Lee Xdressing Adventures

I just love crossdressing sex!

    I have been crossdressing since I was about 14 and by the time I was 18 or so I was meeting with guys I met online for sex and I loved it!   I got married to a hot and sexy lady when I was 23 and I thought that might take care of my tranny urges but in reality it only made it worse. I now have to go long periods between playing dress up and it’s often all I can think of so when I...Read On

16

Fulfilling A Girl's Male Fantasy Part 1

Jennifer has a surprise request for Jack.

"Get undressed," the pretty brunette told me, and I obeyed. She was called Jennifer, we'd met the night before at the rock nightclub, and I'd thought that she looked gorgeous in her goth make up so she invited me back to her place. It turned out that she was eighteen and still living at home, so we locked her door and did our best to keep quiet as we fucked the night away. Now it was noon,...Read On

13

A Nanny Femtastic - 7

A NANNY FEMTASTIC! Chapter 7 After that first dinner Bradley and Felicity retired to their bedroom. And even though they were in a separate wing of the sprawling villa I could hear them making love! I thought of what Felicity felt as a transsexual woman having had a vagina created out of what was her penis. To feel Bradley rigid penis inside her. I wondered how nice it would be to put on...Read On

42

Caught by a neighbour

I've secretly been crossdressing from a young age. In my late teens, around 17, I became more adventurous. maybe because I was enjoying it more. At that age I was very slender, had long dark hair as well has having a naturally smooth and hairless body. My brother and sister were both at uni and my parents would work a lot of the time meaning I was left home alone quite a lot. I would "borrow"...Read On

27

Our Sissy Slave

Will you be our full-time cross-dressing lesbian boislut?

Let me remind you how you came to be in this situation before you refuse. I've been bi-sexual since I was old enough to have noticed how horny women made me. From the moment I noticed, I was unstoppable. My dominant personality seemed to bring me more girlfriends than I could really use. But I always thought the only thing better than a submissive girl is a submissive boy. And what...Read On

21

July 4th Celebration

My wife Ann sets up a mini vacation over the 4th of July.

On July first I returned home from our health club. Ann was packing my suitcase for a mini vacation at a bayside resort. My suitcase was filled with all my girlie things: lubes, vibes, wrist and ankle restraints and the paddle she used on me when I was bad. She also said Ben, his brother Josh, and two others were joining us. Before continuing, I should mention how I became the man I am...Read On

19

Surprise

Aubrey greets his boyfriend home from work in a new way. Slight BDSM ahead.

Aubrey swallowed the lump in his throat as his wrists grew sore from his restraints-being handcuffed to the headboard of the bed, naturally he grew stiff. Speaking of stiff... he peered down, under the frilly black miniskirt of his maid outfit was a visible bump, straining against the panties that constricted it, said lingerie was clinging to his soft pale skin. He bit a plump bottom lip...Read On

19

Laying the Groundwork

Extending the boundaries with my fiancee

My fiancée and I always have been a bit more adventurous than the average couple when it comes to sex. While we both enjoy the sensual feeling of pure, romantic love-making, we also tend to get a bit rough and voracious when the moment calls. In the past, we had experimented with some anal play, with me initiating most of the contact on her. Fortunately for me, her hands also had wandered a...Read On

19

Wedding Night: Part One

My fantasy night of being a married girl in bed with her hubby comes true.

As a tranny callboy/escort, I was always fulfilling the fantasies of lots of gay and bisexual men. But there was a fantasy of my own I had had for awhile that I wanted to fulfill with a handsome bisexual escort myself. I wanted to hire a handsome stud escort to pretend he was my hubby and have honeymoon sex with me like I was a bride on her wedding night. Every single girl fantasizes...Read On

49

First time

I was 17 when I had my first experience with another man. My sister was in her sophomore year at college and I in my senior year at high school. She was going to spring break in Florida and since me and her had always had a great relationship she invited me along with her and her friends. My sister was cute, blond hair and blue eyes. Very tan and athletic. She had that all American preppy...Read On

35

I become my wife's girlfriend. The beginning.

My name is Tony and I'm a regular straight guy. This is the story about my life as the part of lesbian couple, and yes, I'm aware of weirdness of this statement. During the first period of our relationship our sex life was fantastic, a man's dream. At this time I wasn't aware of my dark fantasies, our sex was very good and I thought of us as a very nice couple. And then, something like...Read On

29

Chelsea's New Slut

Chelsea makes me her new slut and begins to train me.

            I was wondering why Chelsea wanted to go swimming with me that day.   She had never shown interest in hanging out with me before, but I figured why not go for a swim with friends.   I thought she was way out of my league; she was 5’ 9’’ with beautiful straight black hair and huge double d breasts.   I was just 5’3’’ and a science nerd.   I mean she said it was just between the two...Read On

29

Confessions of a Sex Crazy Cross Dresser

The first two chapters of my first novel

The Confessions of a Sex-Crazy Cross Dresser Book I: The incredible first few weeks Chapter 1: Panties Thief and the Late Night Swim My name is Sandy. My name is Tony. I know it sounds confusing, but when you are a cross dresser life is always confusing. Just the terminology alone to describe you…crossdresser or cross dresser? Transvestite, tranny, she-male and many other names used...Read On

26

My First Real Outfit

My First Real Outfit I started completely dressing in women’s clothes shortly after high school. I didn’t really own anything of my own but I would fully dress in my mothers clothes a few times when I knew she would be gone for a few hours.. Usually it was just pantyhose, bras, and panties that I would borrow from my mom . I had experimented with it a bit when younger, stealing my...Read On

23

Accepting an invitation

On the third day of house sitting, I awoke to a nice surprise. After my neighbour, Daniel, had unexpectedly visited, I had decided to work on my make up and mannerisms. After a day of walking in heels, I had perfected my sexy walk as well as getting my make up just right. I was feeling in the mood to show off my new found skills so was excited to see a note waiting by the front door. It was...Read On

23

Aunt and Uncle Sex Slave

It was the summer of '82 and mom and dad were going through an awful divorce. They decided that it would be best that I stay with some good friends of theirs, Charles and Betty, while they got through this difficult time. They were an older couple, both were around sixty at the time. By this time I was a fully fledged cross dresser and no one knew of my secret except a neighbor. I had all of...Read On

20

My Dream story Part 1

My first story, be nice! Just a start to this story line.

My name is John, and this is my dream. I am 18 years old, I have dressed before but never seriously, and down the street from me lives a woman named Sarah. She is the mother of a very wealthy family and just radiates control and success. Ever since I had seen her, this story has played over and over again in my mind. So here it is. I woke up and the weather couldn't have been nicer. The sun...Read On

18

The Note

I awoke, sorry came to the following morning, still had on my tiny red skirt, blouse, nails and all my make up. I walked into the bathroom and looked in the mirror, OMG what a sight looked back. My make up was smeared over my face and a thick dried string of cum was visible on my cheek. I went back to the bedroom and grabbed my handbag, opened it and took out a cigarette, lit it and inhaled...Read On

15

the summer I became Suzie chapter 2

this is my fantasy

CHAPTER 2 My eyes follow a trail of goosebumps to where Jack's gentle tongue teased my sensitive nipples to life, driving me crazy. He reached into a pocket of his discarded shorts and pulled out a tube then demanded I turn around so I could see my pussy. "Wiggle that ass and tell me how you loved sucking Harry's cock"! Jack grated. "Oh yes, I loved sucking his cock." "Can you still taste...Read On

12

A Nanny Femtastic - 8

A Nanny Femtastic Chapter 8 When we got back to the villa I needed some time alone and left Thomas with Bradley and Felicity. We were all to meet for dinner that evening on the terrace. I had a few hours to myself and ran a big deep, bubbly bath. I had got used to pampering myself with an array of oils and scents. This and of course the regular hormone injections had softened my skin...Read On

12

Violation

Michele is a closet TV and awaits her lover so they can play out their fantasy

Violation By Michele Nylons I have been home from work for over an hour; I lift my head from the brief that I have been reading by the light of a desk-lamp. The room is full of shadows. I look at the antique clock on the mantle and see it is approaching eight o'clock and I look over at the window; it is dark out. I close the file on my desk and then close the curtains in the study. I...Read On

12

A Night at the Ambassador

An early evening of debauchery earns kudos for a crossdresser.

While on business in Colorado Springs, I had the opportunity to visit one of the adult theaters that I had visited previously. Although the booth area was in full swing, the booths had no doors and there was no privacy what so ever. One could still have a good time if they were so inclined. The attendants were cool and they did not mind the actions of others as long as there were...Read On

42

A Visit

Husband dresses up for his wife so that they can have a little fun during the weekend

My wife knew of my enjoyment to wear women’s lingerie when we married and over the months that followed our honeymoon she had often wanted to see more of me dressed up.   I always enjoyed these times although they were not as frequent as I would have liked them to be. One Friday, after a rather long and difficult week at work, I returned home and was greeted by a tender hug and a loving...Read On

34

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

28

Adventures in a Woman’s Body – Chapter 1: Plugging Up

Dressed up, plugged up, and ready for some cocks

After two years of hard work, I've finally come as close to being a woman as possible. The hormones and drugs that I've been taking for the past five years have made my body and voice quite feminine. With the help of toning exercises, I now have long slender legs, a soft and juicy ass, very feminine hips and a thin waist. My skin is very soft, smooth, and white thanks to the skin care...Read On

22

My Mother's Boyfriend, My Slut

He seemed like a slut to begin with, who knew he really was.

 Divorce often times traumatizes the children, but in my case, it set me free from all their arguments. Dad signed the papers and walked out the door on my seventeenth birthday; it was the best present he could have ever given me. I was finally free, I could go to parties and hang with guys. Mom was the lenient one who was always gone on some major trip. I was cool with it until she brought...Read On

22

My First Time

A true Halloween cross-dressing story

I met Lydia while living in Florida. I had recently won a law suit and didn’t need to find employment for a while, so I spent the first three months partying. A good friend had sponsored my membership at a well known and popular yacht club. They had a public side and a members-only side; the members-only side had better bands and more folks. If you parked your yacht and paid the docking...Read On

49

Caught in my girlfriend's lingerie by her friends

My girlfriend lives alone, so whenever I am at her house by myself, while she's out clubbing or working, I always take the opportunity to go through all of her sexy clothes and lingerie and dress up like the slut that I crave to be. I undressed and put on a pair of white fishnet stockings, a black thong, mini skirt, black and white see through top and a sexy pair of silver high heels. I set...Read On