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Crossdressing

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18

Halloween Fun

First time Out

My friend talked me into dressing up as a female this Halloween. It wasn't much of talking into; I was a closet cross dresser for sometime. The only person who ever knew was an old girlfriend, Mel, a few years back. It was a good thing she was bisexual because she was really into me wearing her clothes. She even mentioned that I looked better in her clothes than she did. So, I started wearing...Read On

22

Caribbean Vacation part 1

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

Susan & I often traveledto 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 shop...Read On

52

First Time Out

Crossdressing In Public

 This is a true story about my first time I went out dressed at a club I had been in the closet for years and up until this point only a few people had ever seen me dressed my freind Bill and some guys I went to an adult book store.  I had been dressing for Bill alot in mine and his apartment but I had this erge to go out clubbing dressed I had asked Bill several times but it seemed he...Read On

43

The Feminization of Michael - Chapter 1

The Feminization of Michael. Chapter 1 How I had found myself in this predicament Ill never fully understand. Ok I guess it was my own fault but why I didn’t kick against it when I could Ill never know. I had been involved in a sordid night of drink drugs and sex with a young transsexual hooker! Including her/him putting a bra and panties on me! I didn’t know any of this until my...Read On

28

The Slut Within

This is my first story. If you like it please comment and I will write chapter two :)

I was 22 years old at the time, and I had been crossdressing for a few years. For some reason I could never control my desire to put on women's clothes and prance around my apartment looking all sexy and slutty. Normally I can never decide what specifically to wear as I like to change it up all the time, from wearing latex lingerie to sexy roleplay outfits and beyond. I am 5'9 with a...Read On

39

Two girlfriends stay in for the night

Wife pleases her girlfriend then tells her whats going to happen next

The other day I came home from work and was looking forward to spending the evening with my wife. We had the next day off, and it was going to be great to just get some time with her. After I was home and settled my wife Dawn came and found me and told me she wanted to spend the evening with a girlfriend and have some fun. I was a little disappointed, but a few seconds later, she told me...Read On

18

The Guest

Is this in the job description?

"Do you want to keep your job or not?" She asked me. These were desperate times, I was up to my eyeballs in debt and bills, and the job at hotel was all I had. She had threatened to get me fired. I thought back to the beginning of this, wondering how I had got here. Slightly earlier "The lady in room 404 just called to say she had some kind of trouble with her wardrobe door,...Read On

9

A weekend with Nancy

It was staggering to think that it was only 8pm and Nancy was to be with us the entire weekend

  CHAPTER 1 Upon arriving home from work one Friday afternoon my wife informed me that the kids would be staying the weekend at some friends house, and that she had made some special plans for us. She then went on to say that she would be gone for a couple of hours and that while she was gone I was to shower and to shave myself from head to toe. Then I was to get my...Read On

26

The Worm Turns-Part 1

My submissive girlfriend turns into my dominant wife

I must have read about a million of these stories and I have to confess that mine isn’t so unique--maybe only in the details, but not so much in how things started or how things ended. You can probably write the first lines yourself: “Things started out so innocently. We had a typical relationship that somewhere, some way, took a dramatic turn that I never saw coming. At first, I was all for...Read On

44

Caught by Uncle in Aunts things

When I was a young boy, I started to find a fascination with feminine things.  Not sure how it started, but one day I found myself trying on some of my Moms things and enjoyed the feeling.  The issue I found early was that my Mom was very vanilla in her things, so I started to explore with an Aunts things, one I spent a lot of time with, as her son and I were very close.  She had very...Read On

15

Teenage CD Awakening Part I

A tale of a teenage boy’s first overwhelming urge to try on a pair of panties

As a child I lived in a town in the North of England. It was a fairly conservative place, where boys were expected to grow up to be men, and girls to become women. Despite this my mother was a fairly liberal person, and by the time I’d reached the age of 17 the topic of sex had already been raised in our house. Sex between men and women of course, with the aim or perhaps the danger of...Read On

45

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

51

Taking Control

Wife busted me doing some of my favorite things and then took control with some role reversal

* this is a story of how my wife busted me doing some of my favorite things and then took control of the situation with some role reversal to satisfy both her and my hidden desires - enjoy! * It was one of those rare days when I was working from home and my wife had plans to be out running around with a couple of girlfriends for most of the day. Work had been dragging me down and I was...Read On

24

Group Fun

Caught outside and forced to suck.

  This is a story of what happened a long time ago. I was 20 years old. I have always been a small guy, 5-5, maybe 125lbs on a good day. All the girls called me cute and I hated it. Until I tried on my girlfriends panties. Wow, I thought how girls were so lucky to wear all this sexy stuff. Well within a year I had gathered a couple of very slutty outfits. I loved Garters and stockings,...Read On

19

My Day in Panties

The day I spent at work in my hot panties

I'm a 21 year old sales rep for a drinks supplier. I'm tall and skinny, and love little sexual secrets....today was just another day in this secret life. The alarm clock rang out like a drill sergeant screaming at his soldiers. 6 AM and it was already light outside. It looked like it would be yet another clear sunny hot summers day and I awoke laying naked in my bed. It appeared that my...Read On