Transsexuals+&ampamp;+crossdressers Stories

12,315 results
Orientation
Length
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Infinite Scroll

The Mistake

by teasingtee on Sep 16, 2017
Transsexuals & Crossdressers

First let me tell you that the following is true, it happened to a friend of mine who was 18 at the time. This is his story told in his words. I grew up in a small western town in Montana. Some say it was and is a vacation destination. I lived for two things as a teenager, playing football and sex, at that stage in my life, both held equal importance, as f...

A Secret Fetish Ch. 01

by margekershaw on Sep 13, 2017
Transsexuals & Crossdressers

When teaching a section of my favorite class, "Modern Erotic Literature", I noticed a guy in the back of the room acting strangely. He was in obvious discomfort, and I wondered why. It was during the lecture where I discuss fetish stories. Students find it a revelation. The first thing I usually do is define "shemale" tales: " 'Shemale' is a hardcore adu...

Craigslist CD Hookup

by Lovinhose on Sep 16, 2017
Transsexuals & Crossdressers

I have been crossdressing since I was a kid. I started out with a pair of my mother's pantyhose, as most other crossdressers start out the same way. Once you get bit by the bug, you're hooked. This is my first story, but I have so much to tell that this certainly won't be my last. All of what I tell you here will be 100% true. I will not dramatize or sensati...

A Great Day Off Work

by Lovinhose on Sep 16, 2017
Transsexuals & Crossdressers

Days off are great. Any day off is a great day. You can catch up on things, relax, take care of business, chill out, and just have a good time. Days off also open the door to many opportunities and possibilities. This day would prove to be a very good day. My wife was working this day, and I had taken the day of from work, just because. I stayed home and d...

Mistress Chantel, Tranny Dominatrix Ch. 01

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Prefix: Welcome to my next erotic story. This story will be written from the point of view of a Transvestite Dominatrix. It is a new twist in my mindset as I normally identify as submissive and as a sissy maid and slut to a dominant Master. It's my 'kink' but I have danced around in my mind a story from a position of Chantel being a true Transvestite Dominat...

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...

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...