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Crossdressing

21

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

29

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

3

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

19

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

13

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

44

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

14

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

45

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

62

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

29

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

17

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

25

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

13

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

37

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

8

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

36

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

8

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

6

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

7

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

5

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

32

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

18

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

30

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

11

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

23

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

32

Wife's Crossdressing Fantasy Part 2

Her anniversary present to me

This is a work of fiction. Any resemblance to any person, or incident is strictly coincidental. Since my wife shared her fantasy with me and made me her bitch, our love life has changed. Now I always have something cute and satiny on, whether it is panties under my boy's clothes, or a silk nighty at night in bed. I love being my wife's bitch and I can never go back to who I was before. ...Read On

9

Yes Captain

The crew gets a little closer than normal

It had been a while since Sarah had a lover. She was aching to slip into something sexy and get a man going. She had been to a few clubs but found nobody that could fix her needs. That was until she arrived at work on Monday. Sarah was a copilot for a major airline. She entered the cockpit and met the Captain John. He was a good looking man. Tall, blonde hair, and a smile that would melt...Read On

47

Wife's Crossdressing Fantasy

My journey from boy to man to woman

This is a work of fiction. Any resemblance to persons or incidents is coincidental. My adventure began while I was a senior in high school. My mother took me to the dentist. It was late afternoon and shortly after I was called into the examination room the receptionist and assistant went home. The dentist then closed the door of the room we were in. He walked over to me and started making...Read On

119

Halloween Trick or Treat Surprise

Dan and Susie go to a Halloween costume party Susie has him dress as a women and changes him forever

Chapter 1 –Susan Charity Event To my surprise Susie my wife of 15 years comes home from one of her many business trips. She is all excited about a Halloween costume party fund raiser, for non profit that supports women studies. The invitation states, the best couple for this evening will receive a free weekend in Bermuda. She wants’ us to go as couple switching genders.  Let me...Read On

18

My Lesbian Lover

My first adventure out as a woman ended in the arms of a woman!

My wife was trying to come to grips with the realization that I cross dressed, with marginal success. Part of her plan was for me to meet in the Twin Cities with other CDs so I could have a ‘safe’ place to dress up, away from our small town. To be safe, I was to drive up, change clothes there, meet with my friends and then change again for the drive home. A good plan … a safe plan … but not...Read On