Transsexuelle & Crossdresser Stories

809 results
Orientation
Length
Source
Infinite Scroll

Crossdresser Evolution Ch. 04

by pantyhigh on Aug 7, 2019
Transgender & Crossdressers

Recap - Crossdresser Evolution - Ch 01 - How I got started crossdressing I was becoming addicted to masturbating while wearing panties. I could feel the arousal but at the same time was ashamed that I was wearing my wife's panties knowing that I would soon be cumming in them. There was this part of me that was telling me, "I CAN'T like this," but there was...

Sissy and Wimp

by 1Gratiano on Jul 14, 2020
Transgender & Crossdressers

1 Now the common belief is that any man who wants to wear women's clothes is gay, and that the heterosexual crossdressers who claim to be straight but "just like the feel" of silk panties and so forth, are being, well, less than candid. Be that as it may, heterosexual and homosexual crossdressers are in fact distinct psychological types. To be sure, ther...

Sarah Meets a Friend

by SarahCD on Sep 16, 2017
Transsexuals & Crossdressers

I posted a listing on Craig's List for a "cum buddy". I explained that I am a crossdresser and that I wanted to find a regular sex buddy. No commitment, just sex. I love to get on my knees to give a blow job. I had several replies. One was local and sounded promising. I don't rush into meeting with a total stranger. First I always exchange a few emails and m...

Rest Stop Romance Ch. 01: Pilot

by Dark_Rose90 on Sep 15, 2017
Transsexuals & Crossdressers

~The following is entirely fictional and just a fantasy of mine. Any likeness to actual persons or events is unintentional and coincidental. Also, this is just a Pilot. If the story gets enough positive feedback, I'll continue it on a regular basis.~ My name is Rosalie or just Rose for short. At least it is when I'm dressed up like a 20 year old college gi...

My Journey to Heaven

by Corina84 on Sep 14, 2017
Transsexuals & Crossdressers

How did I end up here? I couldn't believe what just happened! I was in a daze from what I just did. I was neither sickened or disgusted by it, I was just surprised that I had come so far. Here I was, on my knees with cum drizzling down my face. Something that I have fantasized about for years, but was never able to gather enough bravery to step out and try...

Dad My First Lover Pt. 01

by sarahchica96 on Sep 16, 2017
Transsexuals & Crossdressers

Introduction I'm Sarah a 20 y/o closet Bisexual crossdresser, 5ft 6 , slender body I achieved by working out a bit. I love dressing up in short skirts, dresses, heels, typical lingerie and I have a fetish for the Naughty Secretary look. Main story starts here I had come back home from college for the winter holidays. It was just dad and me at home since...

Crossdresser Evolution Ch. 06

by pantyhigh on Aug 12, 2019
Transgender & Crossdressers

Recap - Crossdresser Evolution - Ch 01 - How I got started crossdressing I was becoming addicted to masturbating while wearing panties. I saw myself in these cum soaked pink panties. I could feel some sense of arousal but at the same time was ashamed that I was standing there wearing my wife's panties. Recap - Crossdresser Evolution - Ch 02 - Getting my wi...

A Day at the Beach

by Danielle987 on Sep 16, 2017
Transsexuals & Crossdressers

Bit of background to understand the context. I am Danielle, I am 18, very petite 5" 8 65kg and have long blonde hair. I have been a crossdresser since I was 12. Australia, it was the middle of summer as I was driving to my friend Kate's house. We had planned to go to the beach as I became more brave in my crossdressing adventures. Kate was the same age as...

Sarah Meets a Buddy

by SarahCD on Sep 16, 2017
Transsexuals & Crossdressers

I posted a listing on Craig's List for a "cum buddy". I explained that I am a crossdresser and that I wanted to find a regular sex buddy. No commitment, just sex. I love to get on my knees to give a blow job. I had several replies. One was local and sounded promising. I don't rush into meeting with a total stranger. First I always exchange a few emails and m...

Parking Area 2 Miles

by Lovinhose on Sep 15, 2017
Transsexuals & Crossdressers

Prior to writing this next installment in my awesome sex life as a bisexual crossdresser, I thought I had already written about all of my worth while, true life experiences, but I had actually forgotten about this one. It happened in, I believe, 2008, during the end of the summer. I was driving my truck. I am a truck driver by trade. Three hours and a co...