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Crossdressing

23

My Sexual Odyssey Part 2: Becoming a Slut

A continuation of the journey described in part 1

After having had a few experiences, I became slightly more comfortable with my sexuality. I decided to branch out a bit, and see what life had to offer. I wondered whether there were any bars or clubs that I could go to to meet people who were looking for someone like me, so I went online and discovered, that yes, there were quite a few such places. It is so wonderful having the internet...Read On

14

Call me Julie

Never assume you have complete privacy.

Coming back to garrison, after a yearlong deployment, is one of the best things ever. Imagine having to go a year without having your favorite lingerie to change into, and not being able to shave and pamper your body as you would like. As it so happens, we just got back the day before yesterday, and after all the clean-up and inspections, we are being given a four day weekend. My...Read On

13

Once Again in Silk - Part 1

It had been many years since my time in Florida and my transformation to Melissa to please my lover, Lydia, and also my own inner desires. She soon grew out of her desire to see me dress up and wanted a normal lifestyle and to date other men. It seemed that our time together had come to an end. I gave up my apartment and I moved back North. As I still had a sizable amount of money left from...Read On

10

My First night

A Night to remember with Marie

This is a true story that I personally have experienced and wanted to share with like minded people. Thankyou.  The evening drew closer after work which had been busy and made me rather stressed. I work as a graphic designer/illustrator in a well known and respected company. I left my studio in London and drove the twenty minute journey that I make, day in day out, to my flat which I...Read On

12

The Sexy Girl-Next-Door: Part Two

Courtney has a neighborly affair.

Once a girl gets a big hard cock in her, there is no stopping her from wanting another one in her. At least, that's how it was for me after my first fuck with my neighbor, Ben. He had just fucked me with his twelve inch cock, with a big head on it and I loved it so much I couldn't wait to do it again. Our friendship was growing like our dicks were. And I was now having an affair with my...Read On

28

Tickets please!

My life changed forever on the 07:28 from Bristol

Standing by the window, I watched as the countryside flashed by. My train had been delayed due to a dodgy signal just outside the station, but judging by the speed the driver was maintaining there shouldn't be much of a delay, thank goodness. Even though I hated my job and boss I needed the money desperately. With a sigh, I turned away from the dreary grey outside and tried to make...Read On

16

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

30

Being Sissy To My Brother In Law

Caught in panties, bsque and stockings.

Jenny knows I love to wear her sexy undies and lingerie but obviously apart from her it was a secret kept from everyone else. One day while jenny was out, I was feeling particularly randy so went to our bedroom & rummaged through her panty drawers. My hand felt the smooth shiny material of a pair of red satin tanga panties and I immediately got a twitch in my flaccid cock. Satin are...Read On

6

Christina and Cheryl - Part 3

Christina encourages Cheryl to go out with a little help from her friends...

I woke up naked being spooned by Christina. Her smooth arms held me tight against her. I turned around and woke her up with a kiss. She opened her eyes and kissed back before pushing my head down. I kiss down her body and slipped her pink panties off. I kissed up her thigh and edged closer towards her clitoris, this is how we spent most mornings. "No, my ass." I lifted her legs allowing...Read On

15

A Sweet College Girl In Love

As a sweet college girly boy, I dated a real big hunk with a ten inch cock.

I went to college in a beach town in California where all of the girls wore their little thong bikinis to the beach and showed off their asses for boys with very friendly results. I noticed that when the girls were bending over while playing volleyball in their little thong bikinis, the boys all looked at them with hungry eyes that I liked a man to have for me.  The sweet little college...Read On

16

Wedding Night For Ken And Barbie: Part One

Catching the garter at my cousin's wedding gets me a honeymoon fuck like the bride.

When I went to my cousin's wedding in Monterey, California stag, at the reception dinner she had me seated next to the only other male stag invitee, the photographer. He was my age and tall and we hit it off, immediately. Ken was a sports car enthusiast and he told me about the thrilling rides he took along the Pacific Coast Highway. He talked about the beautiful views at scenic lookout...Read On

15

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

4

A Terrific Threesome: Part Three

The first of many nights together with our big stud was wonderful.

Before I met Sherry, she had been having affairs with other girls. That was why she had a strap-on dildo to wear. She told me about the sex parties she would have with three or four lesbians that would last all weekend long. The girls would all get together on a Friday night and drink some wine and get naked and have all-female orgies for the entire weekend. Sherry had licked a lot of...Read On

23

From dream to reality

The ladies find out I wear their lingerie

My name is William. I am the eldest of a family of four kids, two boys and two girls. At the time I was seventeen. We lived in a small town, and my parents were well respected. I did well at school, played and succeeded in sports. I was and still am living an intense inner life fantasising on my sporting exploits and sensual encounters. In those days, it was just as normal for teenage...Read On

8

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

17

A Terrific Threesome: Part One

Wearing my girlfriend's panties leads to a big cock for both of us. .

When my girlfriend and I moved into our new apartment, the tall handsome maintenance man came by to put a hand-held spray-jet nozzle on our shower for us. I was home alone and dressed in a sexy little pair of Sherry's panties when he arrived and I put on her little short black silk robe to answer the door. When I opened the door, the maintenance man's eyes went directly down to my...Read On

41

My Sexual Odyssey Part 1 How I Got Started

This is the first in a series of stories that will cover my sexual experiences in chronological orde

I was always extremely sensuous, expressed in the love of the feel of satin and silk, as well as the feel of going barefoot, which was nearly impossible in the city, even indoors, not part of the culture. Where I live now it is, and so I go not only barefoot but also nude when at home. I don’t know if this is significant or not. However, the first time I noticed anything unusual was...Read On

7

Christina and Cheryl - part 2

Christina and Cheryl venture in to the public

"Pedicure?!" I was alarmed. This had all been fun and very sexy, but a pedicure? That would mean I would be venturing in to the public, something I had previously barely even considered. Would I pass? Would I be ridiculed? Would I be verbally abused? Would I be physically abused? These were the things that crossed my mind at first. But then I considered a different scenario. Would I be...Read On

22

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

8

My wife takes what she needs and wants

Normally conservative wife suddenly decides what she is going to take what she needs

I'm a very lucky husband. I have an extremely sexy wife, who is open minded, and loves to please. If she has any faults, it's that she doesn't realize how sexy she is. At 37, she has extremely long red hair (which she jokingly calls stripper hair, but it's actually the truth because it's so sexy how long it is and how it falls against her backside), really fantastic legs, nice curves, lots...Read On

0

Becoming John Collins' Mistress - Part Two

I'm invited to spend a day with one of John's hunky friends

The next day, everyone was a bit hung over. I needed to pick up my car, which I’d left at the bar the night before. Joe said it was on his way and he’d be glad to take me. I borrowed a raincoat from John to wear over my skimpy outfit, then Joe and I headed out. Joe was making eyes at me during the drive, and I decided it would be best to come clean. “Joe, there’s something you...Read On

11

Trio

A secret assignation in a country hotel turns into an unusual menage a trois

Dusk. As he turned off the highway into the country park hotel, Nick was relieved to note that its car park was barely a quarter full. Pulling his overnight bag from the back seat, he headed for the brightly-lit reception lobby. A giggly gang of women were disembarking from a mini-coach. Most were clearly very drunk. In the hotel's spacious lobby he quickly spotted Mark,...Read On

4

Leigh and Leila - Fantasy of a First Night

CD Leila gets read for her first encounter with her girlfriend.

“I don’t know when to stop talking, do I?” I asked. You smiled and kissed me again. It took my breath away. I closed my eyes and let myself get lost in the feeling. It was like nothing I’d ever imagined, nothing I’d ever felt before, nothing I could imagine living without. Your fingers moved just the slightest bit. I nearly came, my cock straining hard against the white satin thong. Your...Read On

14

Christina and Cheryl

Girlfriend makes me cross dress and fulfill her fantasies.

Christina and I had been dating for nearly two years. Within six months into our relationship, I confessed that I enjoyed dressing in women's clothing. She'd been more than accepting and encouraged me to indulge in this. She'd bought me bras, made me wear panties, painted my nails, and given me make overs. Seeing how horny it would make me turned her on even more so. I knew Christina was bi...Read On

13

Night on the Town

The girls and I go out to a lesbian bar.

Night on the Town Barbara Marsh “Well, come on, chicken!” I responded, “Cluck, cluck.” Okay, so I know it’s not original, but it was the best I could do. Despite my misgivings, I got out of the minivan, smoothed my skirt across my hips, and waited for Alexis. Her name’s really Alice, but she was Alexis for the night. The same way Jeanna was Gina and I was Betinna. I don’t...Read On

21

Oh, Daddy

Making of a cum slut

It all started with an online ad. I had always known I was different. I tried to pretend I liked girls, but I really wanted to be one. Let me describe myself. My name is Tony. I am 17. I'm 5' 10", 125 pounds. I have long blonde hair that girls are always jealous of, but it's always my blue eyes that draw everyone's attention. I was pretty shy and mostly kept to myself. I had a few friends,...Read On

12

An Uneven Christmas

He is dressed up by a girl for his friend's entertainment.

By Christmas, Sarah and I had been ‘dating’ for a few weeks. If you could call it that. I had been spending a lot of my time with her, but I often felt more like a servant than her boyfriend. Most couples might curl up together to watch a film, I was more used to curling up at her feet. Worse, I was sure my friends realised there was something odd going on. Mark, who had the room next to...Read On

13

Adventures in a Woman’s Body – Chapter 4: Public Humiliation

Used as a playtoy at the mall

I stepped out of the shower and began to dry myself with a towel. On this bright Monday morning, all I could think about was what happened on Friday night. After being gangbanged and cumed on thoroughly, Daddy drove me home that night. On our way there, he explained to me the situation that I am in. Daddy took out his phone and showed me pictures he had taken of me being a dirty little whore....Read On

28

Shopping with the Boss's Daughter

I came home from work after a successful morning meeting where we finalized a big project. I decided to celebrate by going out to buy a new dress. I changed out of my business suit and grabbed a quick shower to shave smooth. I put on my make-up, choosing to go with a conservative look for the day with a pink lipstick. I got dressed with black panties and bra, and pulled on the silky nylons...Read On

24

Workouts with My P.E. Coach

Courtney has a crush on her P.E.coach, Coach Cocker.

My P.E.coach, Coach Cocker, was a tall, handsome man. More than once when I saw him blow into his whistle, I wished he was blowing me. I was a seventeen-year-old tranny-in-training and I loved having a big handsome man sucking my dickie for me. So, it was only natural that I would want Coach Cocker sexually. I already liked flirting with him like the girls did. And I thought he liked me, too. ...Read On