Crossdressers Chastity Stories

18,166 results
Orientation
Length
Source
Infinite Scroll

Sister Mary-Margret and Jenna

by tgirl_Mary on Sep 12, 2017
Transsexuals & Crossdressers

This is not another cliché Halloween story. The fact that it happened on Halloween is purely coincidental. It is a story about a night out with my friend Jenna. I first noticed Jenna on her online profile. It was a transgender and cross dresser website. I had my own profile on there for a number of years. I had just turned forty and had been actively cross-d...

The Bus Ride Home Ch. 3

by iser21 on Sep 12, 2017
Transsexuals & Crossdressers

The last time I sent something in it was about Friday night. The first date with Amy. She took me to a place that I have never been. The sex was so great. It is now Saturday and I just got up, about 10:00 am. And let me tell you, my ass hurts, not to bad. But it feels like I have been butt fucked 100 times. But it was only 5 times. My jaw hurt's from taking...

Mistress and Master

by davemacc65 on Sep 16, 2017
Transsexuals & Crossdressers

I had been to Mistress Elaine's and Master Johns several times but today's visit was different. Mistress Elaine had buzzed me in the gate but it was James their butler who waited for me at the door. I had not met the staff of the house properly but I had heard them moving around and cleaning. I had wondered if Mistress had more slaves but the people I had br...

My First Time Sucking Cock Pt. 02

by katiecdsub on Sep 13, 2017
Transsexuals & Crossdressers

This is part 2 of a story in the First Time category titled "My First Time Sucking Cock". ***** Teen (18) male experiences interracial sex with older man. I got back into my usual routine and often thought about him and had conflicting thoughts by this time. I went to the gym at different times hoping not to run into him again. I like the softness of girl...

I Never Thought...

by Randomguy664 on Sep 16, 2017
Transsexuals & Crossdressers

I would consider myself lucky. You would consider yourself lucky too if in your dullest, longest and most tedious class there was a cute girl sitting next to you. The class was Economics 101, and no college career would be complete without an incomprehensible class that seemed to never end. The fact that all my fellow college buddies are hanging out at this...

On the Edge

by Ijhel on Sep 16, 2017
Transsexuals & Crossdressers

1_On the edge "You're fucking disgusting" Linda snarled at me. I blinked repeatedly, trying to fight back the unstoppable tears that welled up. "Just look at you" she continued. Her eyes flashed with anger and she stepped to the door, jerking it open then turning back to look at me again. For an instance, her eyes held mine, and through my blurred vision I...

Alexis Ch. 03

by naughtynikki112 on Sep 12, 2017
Transsexuals & Crossdressers

Hey everyone! This chapter features very little sex. I feel like it's necessary for the development of the story though, since it's a big turning point for Alexis. I decided to wait posting this so I could post the next chapter as well, which gets back to all of Alexis' nasty, slutty adventures. So if you are really into the story, then stay with me. But...

Wife Becomes Bitch

by Intercontinental on Sep 16, 2017
Transsexuals & Crossdressers

"This is a true story of my T journey. If you want to start from the start, try "The Odyssey", "The Odyssey Ch2","Becoming a wife" "Being a Wife" and "Lucy Learns More". Each story is self-contained and is an erotic vignette in itself. But fellow t girls may want to see how it all began." * Lucy had settled into domestic life and was quite enjoying it. Her...

Stevie's Coming Out

by michaellajones on Sep 15, 2017
Transsexuals & Crossdressers

Chapter 1 – Early Days I couldn't believe my luck, alone at last with weeks of fun time ahead of me now, my cock stirred at the thought as pictures filled my head , visions of silk and lace washed over my overactive young mind causing an eruption in my hand. The warm spurts of my cum soaked my eager fingers and seeped into the panties I had always been so c...

My First Transsexual

by iser21 on Sep 16, 2017
Transsexuals & Crossdressers

When did it all start. After the first few times with my best friend (Ed), I thought I would try another guy. That went well. By the time I was in my second year of college I knew I was Bi. Being Bi, I think is better then being just gay. You can have men or women. I had had about 6 different guys in college. And about 5 woman. They all knew I was Bi. By my...