Crossdressers Chastity Stories

18,166 results
Orientation
Length
Source
Infinite Scroll

T-Girl, the Superhero

by WriteOrWrong on Sep 19, 2017
Transsexuals & Crossdressers

This story is pure fantasy. Hope you enjoy reading it as much as I enjoyed writing it. And as always, votes and comments are appreciated. Enjoy! Stan was sitting in his car in front of the bank, waiting on his new friends to make their withdrawals. He was new to the city and didn't know very many people yet. So when he met Frank and Vince while playing pool...

New Beginnings Ch. 09

by 69plus1 on Sep 14, 2017
Transsexuals & Crossdressers

It has been less than a couple of weeks since my time with the guy in the showers at the gym and was still waiting to hear from him. After his wife caught us he quickly dressed and they disappeared into the night. I hadn't seen Tara or my ex and was getting a little tired of jerking off. Thinking I might have to go on the prowl I came home as the phone was...

A New Beginning

by CrazyCrystalTS on Sep 25, 2017
Transsexuals & Crossdressers

"This story is about transsexuals. If you are not interested in this kind of story or find it offending, hit your back button and find something else. It plainly tells you what kind of story this is and if you don't like it, don't read it! There's no point in wasting your time just to read it and tell me how it offends you. I really don't care because you sh...

A Sissy's Reward

by keptsissy on Sep 19, 2017
Transsexuals & Crossdressers

Every time he does this to me he drives me crazy, keeps me addicted to his hand. I feel my sissy-like penis strain to escape from between my legs. I'm very small, only about 3" when hard. I keep it tucked for him, hold it tight between my legs at all times...except for when he does what he's about to do to me now. He's not interested in my tiny thing. Only...

Mistaken Identity

by tonyl65 on Sep 25, 2017
Transsexuals & Crossdressers

If you do not like sex between men, and/or transgender sex then this story isn't for you. Here I am at a hotel bar at another boring, sales convention. I'm divorced, 40 years old,but still have some looks left in this salt and pepper old guy. I work out a couple of times a week, which at least keeps the midsection tight. Not what you would call a GQ m...

Not So Subtle Changes Pt. 01

by DaniW on Sep 16, 2017
Transsexuals & Crossdressers

Note: this is outside the norm of my other works, in that it is more "far-fetched" than anything I've done previously. I hope you all enjoy it. :) ***** For as long as I can remember, I've always had a more feminine way about me. Even though I was born a male, my interests always seemed to lie with dolls and playing house and things like that. Throughout...

So You Want to be a Nurse? Ch. 07

by MicheleNylons on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Seven - Michele Ascending Michele and Polly sat in Michele's lounge drinking tea and smoking. "So? Inspector Burgess?" Michele asked. "Well you know the Matron runs a prostitution ring and that most of the clients are the elite of CMH and the hoi polloi who make up their close circle of friends," Polly went on. "Well us girls and our punters nee...

Sniffer and the Hotel

by tonyatll on Sep 16, 2017
Transsexuals & Crossdressers

The story starts with me getting an email on a sex website I belong to from someone calling themselves Snifferthenslave. The email told me that they were a secret submissive bi cross dresser that wanted to know if I wanted to meet for them to pose as directed for my camera and anything else I told them to do. I emailed back that I was interested and had a b...

Black Cock & Birthday Presents Ch. 05

by frezrevup on Sep 14, 2017
Transsexuals & Crossdressers

"Hi, Baby!" my wife said then ran across the cavernous hotel suite to hug me. "There's cum leaking out of me everywhere I said. I ruined your dress." "Stop it...naughty girl," Angela said. She pushed my hand between her legs to feel her sopping pussy. "You've never done this to me before. Oh I love it, sweetheart. You look so sexy with a black cock in you....

Young Guy Goes To College Ch. 02

by pantysubsissy on Sep 26, 2017
Transsexuals & Crossdressers

Thank you all for the great comments and votes. It helps keep my motivation going. As I woke in the morning I could feel Julie's body pressed next to me. I realized that this wasn't just a dream. I had actually gotten to "third base" with a girl. Granted I was still a virgin on the day after my eighteenth birthday. But the day of my birthday was by far the...