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Crossdressing

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26

Ray and the Halloween Party

My friend Ray meets Lisa for the first time as we go to a Halloween party....

   I have had sex with a few guys since my last story but there nothing much worth writing about so I thought I would “go retro” and tell you about a hot experience I had in my senior year of high school.    At that time I kept my crossdressing pretty much private and only a handful of people knew about my slutty side as Lisa. Even most of my best friends had no clue. (At...Read On

26

The Pool Man

Sunbathing near the swimming pool, I turn on the handsome new pool man.

It was June and time for sunbathing by the pool in my backyard. To my pleasant surprise, I saw that the pool man the company sent this year was young and handsome with a muscular body and porn star mustache. I was instantly attracted to him the first time he came and we hit it off quickly. I was wearing a pair of cut-off shorts with a sexy black thong panty underneath. And I felt very sexy...Read On

23

Andrew to Andrea (Part One)

Andrew is about to really see the other side

Hi, I'm Andrew; at least I was Andrew full time until about a month ago. I have always been fascinated by lingerie: its feel, its appearance, how it just makes a body look that much more sexy. Like most curious types I started young (at sixteen, so not all that young), swiping what I could from my sisters or cousins when I could and squirreling my prizes away until I could find time for them....Read On

23

Nice surprise for the delivery man

Me and the delivery man get cosy

I'm a crossdresser in my early 20's and still live at home unfortunately. The day started as it usually does when I'm home alone, dressing up. On this day I had gone for a pink G-string with a matching bra, my breast forms, and some tight leggings which showed off my pert bum very nicely. A black lace top and of course my light brown shoulder-length wig and my make-up. I was in a bit of...Read On

17

First Time, First Fuck, New Porn Star

A story I wrote while on a short break from my Missy series. Don't worry, I just need inspiration.

I am just a normal guy however I have what some would call an abnormal fetish. I am a 23 year old guy and I like to wear and dress up as womanly as possible. I am 5’9, a little chubby but can still pass as a woman, with brown hair, brown eyes and a 5 inch cock. One night I had gone out with one of my friends and had gone drinking to a few bars. As we went from place to place we started...Read On

17

Minding the House

Short true story about the fun I got up to while minding my neighbour's house

My neighbours Tom and Paula were going away on vacation and they asked me to keep an eye on the house for them. I gladly accepted as I wanted to see what their house was like on the inside but my curiosity really lay in exploring Paula's underwear collection. Paula was a 34 year old pretty mom of two kids, 5ft 7 with blue eyes and shoulder length brown hair. She possessed a slim but...Read On

17

The Sexy Girl-Next-Door: Part One

Wearing too many sexy clothes gets Courtney a big cock inside her.

As a sweet sixteen-year-old boy, I started my life of having transvestite proclivities. Being sexy for men and making their cocks hard for me became my favorite thing to do for pleasure. I already had a boyfriend, the blonde college boy lifeguard at my community swimming pool. He had seen me wearing some sexy little hot pants and come on to me, one day. The fact that he was handsome and all...Read On

14

My oddesy 2 - Liam

A friend cheers me up

It had been a few weeks since Glen's puzzling rejection and I was in a slump. I hated my body more than I had in years. Not even sneaking into my sister's old room and playing dress-up could cheer me. And my best friend noticed. Liam was in most of my classes at school and we knew each other since third grade. He had olive skin and a solid German build. Noticing my gloomy disposition he...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

14

Transitioning and Bound

Vanessa and her man find a mutual pleasure - her with other men

It had been a while since I started the hormones, and I couldn't have been happier. I was looking and feeling more womanly than I ever thought possible. It brought me a new confidence when I was in public, and made me feel so much sexier, and girly when I was in the bedroom. My breasts weren't that big, but they were growing over time. I had a nice handful, and Greg said he loved to suck on...Read On

14

Jessie and Sue

Jessie gets invited on a wild date with Sue.

I felt like my life was spiraling out of control. It all started that one fateful weekend when my secret love of cross dressing was discovered by my coworker Dan. He knew he had me, and he had his way with me. Then came the next weekend when Dan invited me to his house only to have himself, Aaron, and Zach take turns with their sissy slave. And now last night, I was humiliated because of...Read On

32

A Whole New Me - Part 1

Borrowed panties and a day with my friend reveal a whole new side to me!

“Honey! Are you around?” I shouted from my room, rummaging through my drawers and naked from the shower. “What’s up, sweetie?” My girlfriend, Lisa, popped her head around the bedroom door. Her eyes taking in my body and a cheeky smile forming on her pretty face “Oh, looking good.” I wasn’t the most muscular guy but I wasn’t fat at all and Lisa always claimed she liked my body not being...Read On

32

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

29

Jessi's coming out party

Jessi comes out to several friends and has an interesting night.

Hi everyone. My name is Jessi, I'm 23 and I have been a crossdresser for over three years. Recently I decided to go full time and was going to met up with some friends to come out to them. I arranged to go hang out with them at my friend Derek's house, them thinking I was still coming as my old self. My roommate, who started my path into crossdressing (that's a whole other story), told me if...Read On

22

A trip from his Hotel Room - Part One

Paul likes dressing up on his business trips, but this time it goes a little further.

As Paul did when he made every business trip to the big city, once he had checked in to his hotel room, he quietly made his way to the streets where there was a profileration of sex shops. He wanted to find the sexiest, sluttiest clothes that he could change back into when he returned to the hotel, and maybe a toy or two to enhance the stimulation. First up was some lingerie – definitely...Read On

Mistress Hannah's Pathetic Husband Part 2

The transformation begins

During my first week as her new slave, Hannah decided that I was too hairy for a little sissy boy, so I had to begin removing hair from the tip of my nose down. The mustache went first. It really was kind of pathetic anyways. I actually got compliments from some of the women at work about how handsome I looked without it. I had grown it because I had a "baby face" and I wanted to seem...Read On

10

A Terrific Threesome: Part Two

The fun threesome gets kinky in the bedroom.

When I told Sherry about the handsome maintenance man with the thirteen inch cock, she said, "He sounds delicious." I explained how he caught me wearing her panties and wanted a blow job right away. How I offered him a beer and a blow job and what a good fuck he gave me, too. We felt like two girlfriends talking about a big stud we both wanted badly and we were both very happy. "Oh,...Read On

10

Crossdressing Domina gets a new slave

A new slave drives a crossdressing Mistress wild.

I have been a crossdressing Mistress for several years now. I have a petite body and always looked good in a dress. I take on many slaves but my favorites are other men who look great in dress. This is a story about my favorite slave I have ever trained. I had been anticipating the arrival of my new toy all week, and he was moments away. My new slave, eager to be trained under my heels....Read On

34

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

28

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

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

13

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

13

Explorations beyond my expectations

My introduction to pegging, cross dressing and so much more

I was nineteen at the time and Lili was my first college girlfriend. She was a virgin when we met. I had only had one intimate girlfriend before her. We loved to explore together and every weekend her roommate would leave town on Friday night and wouldn't return until Sunday evening, giving us plenty of time to explore and play. She knew I liked ass play from conversations about things...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

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

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