Crossdressers Stories

12,121 results
Orientation
Length
Source
Infinite Scroll

Home in the Hills Pt. 01

by ValoryG on Dec 10, 2019
Transgender & Crossdressers

All names and characters in this story are fictional and have no connection with any actual person living or dead. ***** Jonathon Worley is in his sophomore year at Onanoma State University, majoring - at least for the time being - in art history. He's the third child in his family, and after his parents paid for the first two to go to college, there was...

Escapism: Nightingale

by chasingrisque on Sep 13, 2017
Transsexuals & Crossdressers

I slobber on the thick, veiny cock in front of me. I slurp away like it's an ice-pop on the hottest day of summer. I'm dressed in a red plaid skirt, a white shirt with a matching plaid badge that reads 'head girl', the neckline just low enough to reveal my leopard print bra. The skirt is riding high enough to reveal the matching thong and floral patterned...

Walking Miss Daisy

by RickieRene on Sep 16, 2017
Transsexuals & Crossdressers

My wife works 1st shift. I work second. We don't see much of each other during the week. Our children are away at college. When I haven't been left with too long of a honeydo list for the morning I like to get online for a few minutes and look at a little porn. I like a lot of different things, but one of my favorite subjects crossdressers. Today I had a lit...

Strange Love

by komrad1156 on Sep 16, 2017
Transsexuals & Crossdressers

*Note to readers: I've written quite a few crossdressing stories, many of them my own personal exploits. This is the first time I've written one from the perspective of an admirer. I hope you enjoy it. Callie ******* "I'm sorry, but I'm a little confused over here." There was some nervous laughter in the room. "I thought most of yuze people were gay. No?"...

My Babysitter Ch. 02

by GreenGale on Sep 11, 2017
Transsexuals & Crossdressers

There it was again. That hard, warm cock in my mouth. I loved it. I needed it. I knew it wouldn't last, though. I awoke from my dream with my hands on my dick as usual, but my mom was standing by my bed. I was so surprised to see her standing over the bed I almost forgot to conceal my erection. "Hey son we're home from our trip to Hawaii!" she beamed. "Oh...

The Roommate Pt. 16 - Miranda

by ValoryG on Sep 19, 2017
Transsexuals & Crossdressers

So now, Lori, the former Josh, intrepid college teacher and author, was again without a roommate and forced to scrimp to afford her apartment. After Miranda and Leigh Ann, the apartment felt quiet and empty, and she was unable to completely celebrate living as a woman. However, she could afford to shop used clothing stores -- looking, looking and looking to...

A Transvestite Odyssey

by lynntg0444 on Mar 18, 2020
Transgender & Crossdressers

I like playing a girl, but it's complicated. I have always been more attracted to women than men, and had many relationships with women including two marriages. As a young man I had several sexual experiences where I played a feminine role. Wearing girly things was a real turn-on for me, and it seemed to make it less queer for us both. I would later learn th...

Allie and Martine

by chloevargas on Oct 5, 2020
Transgender & Crossdressers

After a second drink, I had to go to the bathroom. I ordered another, looked at the girl next to me and her friend with whom we had been talking, nodded to the bartender. Shelly, the girl next to me, smiled and giggled, "Thank you!" "Save my seat?" I asked and she laughed out loud. I took that for a yes. Shelly and Martine worked in accounting. All the you...

My First Time as Sara... Pt. 04

by Sexy_SaraCD on Sep 18, 2017
Transsexuals & Crossdressers

I love being Sara and everything it has awakened in me. In the months since I have been with Steve and becoming Sara, I have slowly shredded away my old self like a snake looses its skin. The only time I even dress up as John is when I'm at work. Even then, I have a little bit of Sara with me by either wearing panties and sometimes pantyhose under my khaki p...

Mistress Aminata Kanu's Dungeon

by Samuelx on Feb 7, 2018
Transsexuals & Crossdressers

As Salaam Alaikum, to any kinky fellow Muslim reading this. Salutations and greetings, ladies and gentlemen. I am Aminata Kanu, also known as Mistress Ka, an expert on BDSM and Black sexuality. I'm a young Black Muslim woman living in the City of Santa Barbara, California. Before we go any further, I must warn you that I'm into some truly extreme shit, and I...