Crossdressing

SashaCD_ThongPanties

My first halloween night as a teen CD!

My first time i dressed up like a chick and how lucky i got that whole night

This is halloween!! A day that everyone goes out and dresses up in costumes and other things, and go to parties and drink and show off their wild side until the wee hours of the next day. And I thought to myself, since everyone goes out and wears costumes, why not dress up myself into something wild and willy?? Or in fact, why not dress up in a manner of expressing who I am and what I...Read On

Added: 13 Nov 2009 | Category: Crossdressing | Avg Score: 4.85 | Tags: thong  shower  crossdressing  anal  creampie     | 2 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

purekink

A Taste of my Girlfriend's Dildo

I'm caught - and made to love it.

I can’t think of anything I’d rather be doing than sneaking into my girlfriend’s wardrobe while she’s out and trying on her lingerie. The moment she leaves the house, I head for her garter belts, bras and knickers. I don’t have anything to put into her 36C bra cups, and my cock barely fits her panties but all that silk, satin and lace is irresistibly sissy and feminine. On the day...Read On

Added: 10 Apr 2010 | Category: Crossdressing | Avg Score: 4.97 | Tags: crossdressing  strapon  fm   | 7 Comments

Kelsie

A Maid Story

Paul lives out his maid fantasy

It had been a long day and Paul was tired.   After a week of traveling and a full day of meetings, Paul was ready to unwind with his wife, Marie.   They were what many people might describe as soul-mates. They were best friends who shared their deepest, darkest secrets with one another and who regularly consulted with one another on a wide variety of topics. Their love life had...Read On

Added: 02 Nov 2007 | Category: Crossdressing | Avg Score: 4.30 | Tags: smoking  spanking  anal sex  maid   | 2 Comments

Adelleda

My First Time

I'll never forget the day I lost my virginity as a cute crossdresser...

I remember I was 16 when I first started becoming interested in girl's clothes. When my parents would go out I would try on my mom's sexy panties and nylon stockings. They would fit right over my slender teenage body. I had always kind of been interested in guys but it wasn't until I started crossdressing that I started jerking off to gay porn. The idea of being fucked in the ass used to turn...Read On

Added: 27 Aug 2010 | Category: Crossdressing | Avg Score: 4.61 | Tags: crossdresser  teenage  first  time   | 7 Comments

libertina

My Strapon Fantasy

A girl helps her boyfriend live out his fantasy

I woke up in the middle of the day and smiled; my girlfriend had gone to work a few hours earlier and promised me a really good time when she got back. I ran upstairs to shower and make sure I was hairless before getting ready for her. I wandered into her room to dress for her arrival. I found a purple sheer thong and matching bra in her underwear draw that would be perfect. I really wanted...Read On

Added: 15 Apr 2011 | Category: Crossdressing | Avg Score: 4.90 | Tags: strapon  crossdressing  role-reversal  anal   | 12 Comments

jjomes

First Time Dressing

Helping a friend find his inner female

A few weeks ago my gay friend Paul phoned and asked if I would go out with him on Friday night. My husband John and I have known Paul for ages and we knew he was getting over breaking up with his long term boyfriend so I happily agreed. John stayed until Paul came round so we could all have a drink together and then he went off with a couple of his mates. After John left we had some more wine...Read On

Added: 20 Dec 2007 | Category: Crossdressing | Avg Score: 3.69 | Tags: gay  crossdressing   | 4 Comments

GirlyWorld

The Panty Princess

Dominant girlfriend discovers her love for submissive boyfriend

Jane and I had only been living together for three weeks when I was caught red-handed. I was mortified when I saw her in the mirror, standing behind me with her mouth wide open. She had managed to come through the front door, up the stairs and into the bedroom without making any noise. I tried to explain that it was the first time I’d ever done such a thing, but she was having none of it. ...Read On

Added: 11 Jul 2011 | Category: Crossdressing | Avg Score: 4.86 | Tags: cross-dressing  humiliation  femdom  panties  blowjob  straight sex   | 14 Comments

philippasubmaid

Caught and the Consequences

Husband caught dressing and the wife's retribution

‘What the hell do you think you are’   I just lay there not knowing what to say and I am sure going very red under my make up.   ………..   I will go back many years and start at an earlier age.   For as long as I can remember I have cross dressed, always in private, without my partners or girlfriends knowing, totally in the closet,...Read On

Added: 18 Nov 2009 | Category: Crossdressing | Avg Score: 3.43 | Tags: crossdressing  female domination  bondage   | 2 Comments

simonelovesyou

Caught in a Prom Dress

I Should of Listened to What my G/F Said!!!!

If you can remember the stories LUCK RAN OUT AND I GOT CAUGHT then good this has escalated from there if not please read it first. It was a few weeks before my G/f college prom and said had her prom dress all prepared and hung up in the spare bedroom where i stayed. (her folks where very strict) As you can probably guess by now i wanted to try it on, it was a gorgeous gold long dress...Read On

Added: 30 Jun 2009 | Category: Crossdressing | Avg Score: 4.11 | Tags: caught  crossdressing  anal  torture   | 1 Comment

thony777

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

Added: 20 Mar 2011 | Category: Crossdressing | Avg Score: 4.63 | Tags: crossdressing  sissy  bisexual   | 8 Comments

simonelovesyou

Keep Silent or Be Caught

Remember be silent or be caught!! Last year my girlfriend got asked to be a bridesmaid. She of course sed yes, this ment she would have to have a bridesmaid dress. Now all cross-dresser has a dream of wearing a wedding or bridesmaids dress and i couldn't wait for her to get it and try it on. The dress was a gorgeous white satin dress from Bhs. The top was strap-less and had a...Read On

Added: 06 Nov 2008 | Category: Crossdressing | Avg Score: 3.83 | Tags: crossdressing  self bondage   | 2 Comments

Suzy

CAUGHT WEARING MY UNDIES.

Found out and 'forced' to educate respected women in village - inc vicar's wife.

CAUGHT WEARING MY UNDIES. Having recently been left quite a large sum of money by my late aunt in her will, I decided to buy my own house, and start my own business as a handyman. Because I was bored with my present location in the north of England, I moved down to the midlands and bought a very nice isolated cottage about 20 miles south of Birmingham on the outskirts of a...Read On

Added: 23 Jun 2010 | Category: Crossdressing | Avg Score: 4.9 | Tags: outdoor  bi  multi  found out  wives  cd     | 7 Comments

anotherfeeling

Put it on!

A not-so-reluctant housemate dresses for his live-in landlord

I was living and working in London, my first job after college. No chance of having a place of my own with these crazy house prices and this being my first job at the age of 23, so I rented a room from a guy older than me, in his mid-30s. His name was Steve and he was a masculine type, split up from his wife but seeing a feisty Spanish woman called Manuela. There were big arguments now and...Read On

Added: 16 May 2011 | Category: Crossdressing | Avg Score: 4.85 | Tags: first time  housemate  crossdresser  anal   | 17 Comments

Chrissy_CD_slut

Chrissy's First Black Cock

Chrissy gets fucked by a big black cock for the first time

  After I awoke from a deep slumber of a much needed nap, I laid there recounting memories from the night before with Todd. I got out of bed, walked to the kitchen and grabbed a soda from the fridge before sitting down on the sofa. As I sat down, a pain rippled through my ass, reminding me of the brutal fucking I had received from Todd. I sat there smoking a...Read On

Added: 17 Dec 2009 | Category: Crossdressing | Avg Score: 4.94 | Tags: anal  interracial  oral sex     | 9 Comments