Crossdressing

kylie_kained

Picked up in the Toilets

How an encounter in a public toilet turns into a lot more.

Here I was just turned 16, I liked to dress in girl's clothes and was very curious about cock, no about sex. Oh, god yes! My hormones were driving me mad with the desire to not only dress up whenever I could but also to have sex. Anything I saw in newspapers or magazines about women, girls or with sexual meaning had my mind just a blur of indecent thoughts. This particular day I had...Read On

Added: 31 Aug 2012 | Category: Crossdressing | Avg Score: 4.77 | Tags: crossdressing  bdsm  oral  spanking   | 13 Comments

Chrissy_CD_slut

Dressed Up and Used

Young Crossdresser gets Fucked again

     This is a continuation of my first story "MY First Time in a Dress".  I love reading your comments, enjoy!      I avoided Dan for the next few days by playing sick.  I was not ready to go over to his house again yet.  My ass was so sore the next day I had to have some relief.  I was still having a hard time comprehending what really happened.      I finally went to his house...Read On

Added: 26 Sep 2008 | Category: Crossdressing | Avg Score: 4.77 | Tags: crossdressing  anal  reluctance   | 12 Comments

Km44

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

Added: 23 Dec 2012 | Category: Crossdressing | Avg Score: 4.77 | Tags: crossdressing  oral  anal  mm   | 11 Comments

SluttyTammyCD

Gang banged at a private club

This is what happened when a friend took me to a private members only gay, bi, and transgender party

After yet another hot weekend at my friend Heberto’s house, I was packing up and getting ready to go home when he told me he had something “special" in mind for us next weekend. I begged him to tell me what he had in mind but he refused. So I left. My curiosity was peaked. The week dragged on thinking about all of the possibilities. The anticipation was killing me. Finally Friday...Read On

Added: 23 Jan 2012 | Category: Crossdressing | Avg Score: 4.77 | Tags: cum  blow job  fucking  snowballing   | 5 Comments

Chrissy_CD_slut

My First Time in a Dress

How I Became a Crossdresser

PART-1 When I was younger I used to go and stay at my grandmas house during the summer. It was a small country town with about 15,000 people. She lived on a quiet street and there was only a couple of other kids close to my age. I used to go and hang out with one guy, Dan who was about 3 yrs older than I and his sister, Pam who was my age. Dan and I used to go mess around everyday....Read On

Added: 05 Sep 2008 | Category: Crossdressing | Avg Score: 4.76 | Tags: crossdressing  oral  anal  creampie   | 24 Comments

bethanngirl

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

Added: 03 Oct 2012 | Category: Crossdressing | Avg Score: 4.76 | Tags: crossdressing  skirt  masturbation   | 11 Comments

Cdashlynninsc

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

Added: 17 Aug 2010 | Category: Crossdressing | Avg Score: 4.76 | Tags: crossdress  wife     | 8 Comments

Jess_cd

A new friend

As I had a nice, big empty house I did what any good 17 year old would do. That first weekend I had a massive house party! I took a night off from dressing up and invited everyone I knew and when it came to the big night there were plenty of people, including a few I didn't know. I chatted to people and made new friends, sharing drinks and having fun. There was one girl there in particular...Read On

Added: 16 Feb 2012 | Category: Crossdressing | Avg Score: 4.76 | Tags: crossdressing  straight   | 3 Comments

SashaCD_ThongPanties

My First Thong

How the thong panty changed my sex life so young

When I was a little boy in grade school, I developed a curiosity so strong that it could not dare be mentioned to my parents...well, except for my father, since he was quite a perv despite being married to my mother who was more conservative than he was. Typical behaviors in a hispanic couple's life, really. No, it was not about my sexuality, but it involved underwear. Specifically, a...Read On

Added: 04 Aug 2009 | Category: Crossdressing | Avg Score: 4.76 | Tags: | 3 Comments

ChelseyR

In Wonderland, Pt. 2

To recap, our protagonist didn't want to dress up for a halloween party, so his girlfriends decided it was time he joined in the fun. They styled his hair, did his makeup and put him into an 'Alice' dress. However, the disguise worked a little too well, as Chris Smith has taken 'Tilly' back to his house after a passionate kiss on the street corner... Chris put his key in the door...Read On

Added: 08 Nov 2010 | Category: Crossdressing | Avg Score: 4.76 | Tags: crossdress  alice  schoolgirl  blowjob  humilation   | 7 Comments

jools

Capri

My first driving lesson

Friend of the family -Bi Curious story This is my very first story, I hope you enjoy reading it and I hope it inspires you to contribute My name is Jools I grew up in the west country from the late 60’s until the present day My tale based on a true story happen in 1970. At the time I would be at the tender age of 16. When your young the time can't pass...Read On

Added: 05 Jul 2009 | Category: Crossdressing | Avg Score: 4.75 | Tags: bi curious  mind games  tights fetish  cock sucking   | 2 Comments

cassandrababy

Surprise at Girls Night Out

Cassie's Encounters in New Jersey

Surprise on Girls Night Out in New Jersey I explained in an earlier story that my life took a strange turn when I turned forty. I had not been cross dressing for many years, but I had the urge again to bring out my alter ego and the urge was stronger than ever. I really prepared for Cassie, short for Cassandra (I also go by Sandy) by taking a year to buy all the things I needed and get...Read On

Added: 23 Jan 2011 | Category: Crossdressing | Avg Score: 4.75 | Tags: crossdressing  anal  oral  group   | 4 Comments

starbelliedboy

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

Added: 31 Aug 2009 | Category: Crossdressing | Avg Score: 4.86 | Tags: crossdressing  bisexual  sissy  forced  strap-on  goth  lesbian   | 1 Comment

cassandrababy

Confessions of a Sex Crazy Cross Dresser

The first two chapters of my first novel

The Confessions of a Sex-Crazy Cross Dresser Book I: The incredible first few weeks Chapter 1: Panties Thief and the Late Night Swim My name is Sandy. My name is Tony. I know it sounds confusing, but when you are a cross dresser life is always confusing. Just the terminology alone to describe you…crossdresser or cross dresser? Transvestite, tranny, she-male and many other names used...Read On

Added: 25 May 2010 | Category: Crossdressing | Avg Score: 4.75 | Tags: crossdressing  sex     | 11 Comments

Karin

The Worm Turns Part 2: The Routine

After establishing a routine, a surprise visit by a man took my tranformation to a new level.

Before I even realized it, we had fallen into a pattern of visits to the sisters’ salon. On a weekly basis, I was having my hair set, my nails done, and my make-up applied expertly by some combination of Kim and/or Kristie. Often one would do the work while the other recorded the proceedings on video or with a digital still camera. Several of the photos made their way onto the mirrors of...Read On

Added: 22 Nov 2010 | Category: Crossdressing | Avg Score: 4.75 | Tags: crossdressing  blow job  beauty salon   | 2 Comments