Transgender & Crossdressers Stories

12,569 results
Orientation
Length
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Infinite Scroll

Leftover Lusts

by allourdesires on Jun 19, 2019
Transgender & Crossdressers

She found you there, tied over the desk, stained face betraying your recent history. A pair of satin panties formed a delicate puddle around the knot connecting your stocking'd ankles. None of your "companions" had bothered to undress you more interested, no doubt, in taking advantage and likely entranced by the lascivious sight of a bare bottom beneath your...

Discovering Stephanie

by CumInMyBum on Jan 16, 2019
Transgender & Crossdressers

I knew i was different but did not know why. I could not put my finger on it. I was definitely attracted to girls and many of my early kisses and fondles were with girls at clubs and bars, but I would also find certain older guys attractive to. I would occasionally feel a twitch in my boxer shorts if an older guy looked at me. At that time I started to disco...

My First Time

by ElephantJuice on Jul 15, 2020
Transgender & Crossdressers

My very first time sucking cock was with a beautiful blonde trans-girl with a big tasty dick. Firstly, I guess you should know a little about myself. I'm approaching 40, married and consider myself straight, I know technically I'm not but it's the category that best fits me if you have to categorise. I don't particularly find men attractive and have no urge...

The Sleepover

by lynntg0444 on Jan 22, 2019
Transgender & Crossdressers

When I was in college, I would spend the night at a friend's house whose parents lived close to the university. One very hot night we were sleeping only in undershorts in the same bedroom. We were both virgins and started talking about girls and both got a little hard. One of us suggested that we "practice" how we would fuck a girl, so we took turns being on...

Babygirl Ch. 02

by AdamWestie on Jul 13, 2020
Transgender & Crossdressers

They helped me out of the bath and wrapped me in a fluffy pink towel and led me back to my bedroom. Dada finished drying me whilst Mummy went off to fetch some things from the bathroom. Dada placed the towel on the bed and lay me down on my back. I felt contented. Mummy came back in with a bowl of warm water, soap and a razor. "Now Addison, in order to get...

Corey or Cora Pt. 02

by mfs1390034 on Jan 28, 2019
Transgender & Crossdressers

I kept replaying the events in my head. The dress... Donovan... Sam... I had never done anything like that. I hadn't even thought about it. But I liked it... No. I loved it. What had happened to me? Was I always like this? I honestly couldn't remember. All I could think about was cock. And where was Sam? I hadn't heard from him since it happened and that wa...

Sissy Cristal Used by Mistress

by mistressandpussyboy on Jan 8, 2019
Transgender & Crossdressers

This is a real life story, another day in my life with my Mistress. We were ready to go out to run some errands, when Mistress addressed me. "Plans are canceled. I want to bang a hooker: get dressed for me." No sooner said than done, I was getting naked, opening my sissy suitcase. I put on a pretty panty, black stockings, a miniskirt and my high heels. M...

Sasha

by Targloyalist on Dec 24, 2019
Transgender & Crossdressers

I await my goddess on my knees, my heart pounding in my chest as I hear the sound of your footsteps outside my door. You knock and I spring to my feet, opening the door. You enter, pushing me aside and closing the door behind you. You are radiant, tall and curvy, with long black hair, smooth caramel skin and devious brown eyes that radiate cold command. Tig...

Danielle's First Time

by FellatiaViper on Sep 15, 2017
Transsexuals & Crossdressers

Danielle was born in the winter to 1976, but she was born a male by the name of Daniel. Daniel looked like a normal male child aside from liking girly things. Whenever Daniel would play dress-up he'd always dress in his mother's or his aunt's clothes and his parents thought that was cute until Daniel got a bit older then his father sternly told him, "boys do...

We Dot Our I's With Hearts Pt. 01

by VSsissy92 on Sep 16, 2017
Transsexuals & Crossdressers

Disclaimer: This story contains transgender and crossdressing themes. If you are not comfortable with these, please go to another story. All names and places are fictional and not intended to represent any real place. All characters in the story are over the ages of 18. ***** Belleville is a semi-suburban town in southern California. Belleville does not bo...