Caught Dressed As A Girl Stories

361,457 results
Orientation
Length
Source
Infinite Scroll

Stevie's Coming Out

by michaellajones on Sep 15, 2017
Transsexuals & Crossdressers

Chapter 1 – Early Days I couldn't believe my luck, alone at last with weeks of fun time ahead of me now, my cock stirred at the thought as pictures filled my head , visions of silk and lace washed over my overactive young mind causing an eruption in my hand. The warm spurts of my cum soaked my eager fingers and seeped into the panties I had always been so c...

Grannie Panties Ch. 02

by grgy56 on Sep 12, 2017
Transsexuals & Crossdressers

Note: This submission includes cross-dressing and incest. If neither of these topics interest you, DON'T READ IT! I am tired of anonymous bullies who don't have the guts to comment with their handle so we can read how great their submissions are. Therefore I will now start to remove these types of comments from my submissions. To everyone else, thanks for y...

Never A Word

by JohnB73 on Sep 16, 2017
Romance

Lance strolled idly down the street, lost in his own thought as the merrymakers at the carnival flowed around him like different currents in a sea of humanity. Bright balloons strained at their tethers, children laughed, and parents scrambled to keep up with their hyperkinetic offspring. Lance, however, wasn't as happy as they were. His girlfriend had broken...

Party to Remember

by SASHA109 on Aug 19, 2017
Exhibitionist & Voyeur

Hi everyone. My name is Sasha I just recently attended a party in which I was the only one in a bikini while everyone else were fully clothed. Just last month, my friend Katie invited my boyfriend Steve and I to an afternoon party at her house. Since with the onset of summer it had been quite hot lately, I decided to take along a bathing suit and take adv...

Becoming A Girl

by drlove1968 on Sep 12, 2017
Transsexuals & Crossdressers

This is a story how I became my step moms little girl. You see I had a very tragic childhood as a boy and grew up to become the girl I am today. But then again it is not so bad because for some strange reason it does feel very normal to me because it is the way I was raised and at times I have felt very much loved. I was raised by my step mother because my...

Halloween Transformation Ch. 1

by girlboybootsie on Sep 12, 2017
Fetish

Last Halloween marked a major change in my life and identity. It is amazing how much changed for me on that one day. And it was all a complete surprise! I had been seeing this really foxy girl named Barbie for a few weeks, and I was looking forward to going to the Erotic Ball with her, dressed up as slut and a dominant S/M stud with our gender roles revers...

My Introduction

by jamiesecret on Aug 18, 2017
Fetish

I was just a girl cruising the Internet for her master. Well I wasn't a girl at all; I was a guy in drag… I advertised on the Internet as a novice TV looking for a master. I got much more than I ever bargained for. I have been cross-dressing since puberty. My friends and I lived near a college, and one day we found a pair of panties on the ground near a dor...

Naughty Girl Ch. 01

by StoryTeller07 on Sep 26, 2017
Exhibitionist & Voyeur

Bernice was willing to indulge her husband, as it was a naughty fantasy of hers too. She took off her coat and threw it into the car, together with the keys. Unable to get back into the car, now meant it was impossible to back out of the game. This gave her an added thrill. She was committed to walking across the park, to meet her husband. She was dressed i...

Caught by Dave!

by kristycross on Sep 12, 2017
Transsexuals & Crossdressers

Let me start out by saying that I was very much in the closet about my dressing and the fun I have when I'm dressed. No one I know even suspects that I'm a slut at heart or that I am the least bit bi. But more and more I keep fantasizing about one of my male friends. He's very good looking and keeps in shape by jogging every day. Several of the times we've g...

Lifetime Mashup Pt. 01

by spaceche on Sep 17, 2017
Exhibitionist & Voyeur

I live in a large city famous for its beautiful people, very hot summers and free spirited way of life. I commute to work every day, go jogging, biking or hiking several times a week. I encounter and experience other people's beauty everyday. I get glimpses, accidentally or not, of their intimacy, and sometimes naughtiness, quite frequently. Here are a few...