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Crossdressing

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17

My First Time

Fist time oral

This a fantasy of mine and my first story that I am submiting. For a long time I had thought about oral sex with another man. I was married a few times and it never really satisfied me completely, I loved sex with them but I longed for sex with a man. I had wondered what it would be like to find a man looking like a woman, I talked to female friend and she helped me to dress up like a sexy...Read On

17

The Adventures of Patty

Patrick becomes Patty and doesn't look back

“You're wearing my things again!” Brenda screamed when she came home early from community college and found me prancing around the house in one of her short skirts. “Take them off, you little pervert!” It wouldn't be nearly as bad if I were her little sister and trying on her clothes but I was her brother. But it wasn't as bad as it could be. I mean, if she knew what Tommy and I had been...Read On

11

The Feminisation of Michael. - Chapter 5

The Feminisation of Michael. Chapter 5 I found out later that I had been in a coma for two months.  I was unrecognisable and unconscious but still just alive. I remember waking up and being totally lost and I didn’t feel like me. Sue was there when I woke and the memory of her face returned as did the events of the run up to that fateful night. When I first woke, I couldn’t...Read On

11

In Wonderland, Pt. 3

'Tilly' spent the night at Chris Smith's house, waking to find it impossible to avoid Leila Smith, a friend, peer and beauty queen. She was not best pleased about the situation, but helped to protect Tilly's true identity in lending out a girls uniform, one purposefully as feminine as she owned. Chris was just about to give them a lift to school... I shuffled down the stairs,...Read On

11

Becoming Chloe - Part 20

Chloe receives two invites for the weekend...

Unsurprisingly, I was very tired the next day, so I tried to keep busy to help me stay awake. Of course, the thought of a phone call from Colin certainly perked me up, and it must have showed. Around midday, Tina came in just to check on things. Nowadays I saw less and less of her at the shop because I virtually ran it on my own, plus she'd had a bad time with her morning sickness, so her...Read On

11

Telling Mom I'm A Crossdresser Part 17: Seven Days Of Sex, Days 1, 2

Part 17 of Missy, Sorry this is long but i hope you will like it.

This is a fairly long story but I broke it into two parts so that you can read the first half in one sitting and find your place easier if you want to come back and read some more. Also, I would like to say that this will be the start of a seven day sexcapade for Missy involving two of her past flings. Please enjoy and rate and comment at the bottom. Happy reading!! ;) It was now Monday...Read On

11

Fulfilling A Girl's Male Fantasy Part 2

Jenny and her friends have a party with a surprise.

Since our first meeting had gone so well, Jennifer and I started going out together. Other than the fact that in the bedroom I was the "man" only about half the time, it was a fairly normal relationship, apart from possibly being even more open with each other about our desires. One day a couple of months after our first encounter, we were both in her room talking and listening to music. ...Read On

11

Sharing Jessica With Nick

We introduced Nick to Jerry's secret, leading to one hot evening in preparation for his initiation.

Jennifer and I sat at my kitchen table on Saturday afternoon sipping beers following our fuck fest with Holly and Nick the night before. Jennifer didn’t have to worry about picking up her kids until Sunday late afternoon and Jerry wouldn’t be home until later Sunday night. We had both woken up late that morning and just now sat down to chat about what happened the night before. Jennifer...Read On

64

Do you want to wear my skirt?

Katie caught me looking at her skirt and made me wear it.

As I sat in the meeting I couldn't take my eyes off her. She was young and so cute and she was wearing a short pleated wool skirt. The skirt was a pink and light blue plaid color. She would cross her legs and pull the skirt down being sure not to show too much. When we went on a break many of us went outside. It was a nice comfortable fall day. I watched as she came out and stood by herself....Read On

23

Where do I begin? Chapter 1

Young man lets his inner woman out during an encounter with an older man.

Where do I begin? I’m normally not very open about my private life, seeing as I grew up under the pretense that secrets are meant to be secrets. However it seems I have come to a point where I am comfortable with who I am and where I have been. Comfortable enough to bare to you all my deepest secrets. Deep breath in, slowly let it out. My name is Alicia, well that's my new name, my old...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

23

Caribbean Vacation part 1

Lost luggage leads to wearing girlfriend's panties as a swim suit and more

 Susan & I often traveled to the Caribbean for our vacations. We loved the laid back atmosphere and all the sun and gorgeous beaches. Last year though we arrived to find that the airline had lost my only bag containing all my clothing including my swim suit! Imagine arriving in the Caribbean without even having a swim suit to wear!     I had just resigned myself to going down to the gift...Read On

16

Busted by a bud

Caught on home turf.

It's a hot summer day in 1994. Nowhere is a small, fairly poor, rural Illinois town; the kind of town where nobody locks their doors. Summer seems to be an average 19 year old. He goes to a small community college and works on the weekend's. He's kind of quiet and doesn't like to be around his parents. Both parents have jobs where they have to work the night shift. Summer's mom works for...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

16

Deann Finds Out

Deann finally works up nerve to go out in public

Jimmy sat up in bed and felt the dry cum on his belly from last night's masturbation. A quick look at the clock told him his parent's had already left for work and their weekend trip so he knew he had nothing to worry about. The plans he had for the day could begin right now. Stepping out of bed, he padded to the bathroom and began the process. A long shower began the day. He made sure...Read On

16

How It Started

I looked and saw her panties in the hamper.

At twenty five and being a blonde haired blue eyed light skinned guy, I had little hair except on my head. So, it didn't take long to achieve the smooth feminine look that I wanted. Of course, I left some "down below" because I looked young and if I shaved it all off I feared looking underage. My blonde hair was long, during the week I wore it in a guy style. On the weekends it was different,...Read On

16

First Night Nerves - Part 2

Tina agrees to meet Barry without 'the girls'

I sat by myself on the bus, my briefcase on my knees, counting the stops and wishing it would go faster. Since Barry’s text message last night and his surreptitious call to my mobile that morning, I had been so excited, planning what I would wear to please him most. Debbie hadn’t heard the beep on my phone so didn’t know that I would be meeting him without her that afternoon. So far I had...Read On

16

One's A Crowd

I almost lost my home... instead I found a date.

After my boyfriend and I broke up, I was devastated and it didn’t get any better after he left to be with his new love.  We shared a house together and had to be creative just to lease the place.  We posed as a married couple because the owner was a major homophobe.  Twice a month, just so we could pay the rent, we would play up our loving couple routine in full costume.  Which wasn’t hard...Read On

16

My Secret Revealed

My life was pretty good. I had an excellent job that paid well and afforded a nice mobile home. I played baseball on the company team and had a bevy of office hotties show up to the games to cheer me on, I even dated a few of them briefly. It was the nights that I really looked forward to. Once the day was done and I was safely behind the drawn drapes and locked doors of my trailer...Read On

37

Tammy, Lisa, and Karen part 1

This is my first story so please give me some feed back.

It was Friday and the first thing I wanted when I got home was a nice warm bath to clean off the day's hard work. I filled the tub with hot water and added some bubble bath. I shaved my legs and underarms. As I slid under the hot water I looked at my toes peeking through the bubbles, and realized I needed to reapply some polish. After a long soak I got out, dried myself off and went to...Read On

32

Telling Mom I'm A Crossdresser Part 3: Missy's Weekend

Part 3 of my Missy series :) enjoy and please rate and comment.

One day while watching T.V, my mother had come in and told me Missy’s services had been requested for the entire weekend and we needed to go shopping. I smiled as we got into the car and went to the store to buy lots more sexy clothing for me to play in. After we had bought all the clothes and makeup needed for the weekend, my mother and I went home so that she could give me the details of...Read On

27

Hot Fuzz

Caught by a cop

If you have read my profile you would know that I am married with three kids, and no privacy. That being said, I try to indulge in my favorite pastime of cross dressing whenever and wherever I can. I was working as a manager for a convenience store where I would have to get up early in the morning to open the store. It was a 24 hour store, so I just had to get there to send the graveyard...Read On

27

The Meter Reader

Caught Wearing My Bikini

I'm basically a 'city boy' but one summer decided to rent an old two story farmhouse in the country. It had its good and bad points. The bad was that it was quite a way from town. I was working nights at a bakery and had to drive the twenty or so miles to work in the dark every night. The good part was that it was secluded. I could walk around the house in just my bra and panties, a short...Read On

22

My First Taste of Cock

Tammy blows and swallows her first cock.

After fantasizing for so long about what it would feel like to dress as a slut and suck a cock, I decided it was time I tried the real thing. I posted an ad on Craigslist with a couple of pictures of me dressed, asking for someone to let me dress for them and swallow their load. I got a lot of responses and most of them just sounded creepy except for Matt. Matt was 36 (I was 25) and a hot...Read On

22

Becoming Chloe - Part 10

Chloe gets fucked by Vickie's new cock, and then Vickie arranges a meet with Tina

As I started to strip off, Vickie insisted that I leave my bra, suspender belt, stockings and heels on. She lay on top of me on the bed, kissing me and fondling my smooth body, which was something I adored. I felt her hand snake between my legs and gently caress my balls. "Mmm, my baby feels full," she whispered in my ear before she started sucking on my lobes. Then she got up and went to...Read On

22

A friend with something extra.

Ian makes a discovery about his boyhood friend.

So here Ian was standing in the doorway to his buddy's room and staring at this drop dead hottie clad in silk, lace and heels that he found inside. It was just a typical Friday and he'd dropped over his friend's house for a pizza and movie night. It was a rotating event for them on Fridays. They didn't have their own cars as of yet and had no desire to walk to the mall and hang out....Read On

22

My First Date

I had met Pete over an on-line dating site, and we had chatted for several weeks and developed a rapport when we decided to have our first real date. We agreed to meet at a local shopping mall parking lot and would do some shopping together. I spent the morning shaving my body smooth and getting ready. I went with a natural look for my make-up, and peachy pink lipstick. I slipped into a...Read On

15

In Wonderland, Pt.1

Costume mandatory...

When I was in high school I was always very camp, which was probably why almost all of my friends were girls. This was definitely why I first ended up crossdressing. I was sixteen and round one of my 'girlfriends' house for a few drinks on Halloween before we went to a house party nearby. I never much cared for Halloween, so just came as myself. When I came in they all sighed since I wasn't in...Read On

15

Crossroads Ch.02

A young crossdresser take things farther.

The second chapter in this crazy little tale. I really loved my little adventure out as a woman. I liked the power I had over men. I was seriously thinking that I would like to live as a woman full time. That would be quite a commitment and one that would change my life forever. As I said before I worked for a really liberal company and one day I got up some courage and went to...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