Transsexuals+&+crossdressers Stories

15,868 results
Orientation
Length
Source
Infinite Scroll

The Life of Janice Ch. 03

by Kim_Oh_No on Sep 13, 2017
Transsexuals & Crossdressers

Her name was Cindy. The barista at the coffee kiosk. I ordered that coffee as Janice, I paid for that coffee as Janice, I made a friend as Janice. She was a petite brunette; pretty eyes. I discovered my voice wasn't as masculine as I had feared as long as I softened my tone and spoke with intent and sincerity. When she got off work, we sat and talked for...

Kissing Crossdressers Pt. 01

by Candyboi on Sep 13, 2017
Transsexuals & Crossdressers

It started when Carla, my hot sexy wife went away on a spa break a few days with some of her girlfriends. Carla is 40 (I'm 48), has blonde hair, blue eyes, 34DD tits and a curvaceous ass. She works long hours in a busy office as a manager, I work in a local library and my job is far less stressful than hers. And her job has definitely taken its toll on our s...

Bosom Buddies

by luk77 on Oct 31, 2018
Transgender & Crossdressers

"Terry, how are you man?" The voice at the other end asked. "Nick?" The low voice on the other end asked. "Yo, man, where did you disappear to? You left the base so quickly nobody knew where you were. All the officers kept mum. Are you ok? I just got back and had to visit your mum to get your location. She didn't want to tell me where you were but I broke...

The Varieties of Transexual Experience Ch. 01

by SciGuy on Sep 16, 2017
Transsexuals & Crossdressers

The Interview "Please come in and have a seat. Thank you for participating in the project...Elsebeth, is it? "Yes, Elsebeth. You're welcome, Doctor, it's a pleasure." "You do understand that this interview will be recorded?" "Yes." "And that the university must keep your identity anonymous?" "I understand." "Alright. Try to relax and be completely hon...

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...

Kim's My Best Friend

by michael1k on Sep 11, 2017
Transsexuals & Crossdressers

I sit here in my room stroking my 6" uncut cock watching my best friend gently fingering and playing with hers. Yes I said her. I've known Kim for years what I didn't know was that she was originally a boy. This information is all new to me and after 14yrs of knowing her she finally told me the story. When Kim was little her parents noticed she was very fe...

Mia More

by seams_straight2me on Sep 16, 2017
Transsexuals & Crossdressers

It was 5 days after my very close encounter with Mia. I was still on very high spirit after meeting her, and fucking her. I could think of nothing else. We kept in touch via text messages and phone calls. She was "on location" for some photo shoot. One less about fashion and more about horny transsexuals having very sexy fun. She sent me a few pictures of...

Be Careful What You Wish For

by DontMindMePls on Jul 27, 2020
Transgender & Crossdressers

This has been written as a one-off while I write some more stories for Jason & Katie. This story is quite different to the 'Jason & Katie' stuff, but rest assured it still involves lots of hyper action! This one has some heavy BDSM elements, and has a pretty dark ending, so if that's not your thing then maybe skip this one. But if it sounds like you...

Shemale Tales Ch. 01

by Richard Norman on Sep 16, 2017
Transsexuals & Crossdressers

Copyright 2005 by the author. * * * * * I didn't know at first that Julie was a pre-op transsexual. She's a beautiful woman, with great boobs and ass. We met at the Club Tango, where swingers went to show off their dancing skills and meet partners for friendship, all sorts of sex, whatever. That night, at my place, I unbuttoned her blouse and discovered...

Oh What a Night!

by golfer07039 on Sep 16, 2017
Transsexuals & Crossdressers

My girlfriend Vanessa is beautiful, sexy and a Transsexual. This weekend she felt like going into NYC to hang out, dance, drink. Since she knew the NYC club better than me, I was ready to go. Our first stop was Lucky Changs, for dinner and drinks. They have a lot of drag queens who are really good and look great as well. We were having a great time teasing...