Crossdressers Chastity Stories

18,166 results
Orientation
Length
Source
Infinite Scroll

Malcolm On the Meddle

by CarrieQ on Aug 21, 2018
Transsexuals & Crossdressers

Malcolm was very lucky to get the job of caretaker at Lucania House. The owners were very selective but far from diligent; they took account of his military service, but failed to check out his dishonourable discharge... As for his time in jail, they didn't ask and he didn't tell! References from friendly former colleagues sufficed, together with his 'hones...

Real Estate Bitch Pt. 02

by mothman34 on Sep 24, 2018
Transsexuals & Crossdressers

"That's it, take my fucking cock you little bitch," Ms. Tyler grunted as she thrust her engorged cock into my mouth and down my throat. "You're going to make me cum soon, do you want my load?? Do you want me to empty my seed into your stomach you little cum slut?? Do you want me to feed you my jizz??" "Yes ma'am," I replied, slipping my mouth from her dick...

Josie's First Date

by Pisceszero on Aug 27, 2018
Transsexuals & Crossdressers

Hi. My name is Josephine, but everyone just calls me Josie, and I want to tell you about my first date... with a boy. This may not seem strange or problematic, but I should mention, I am a transwoman. But I don't like to boil myself down to one specific thing about me. Being a MTF is just something that is just part of who I am: like wearing glasses, or be...

A Murder, A Mystery, A Mistake?

by phoenixcinders on Jul 18, 2018
Transsexuals & Crossdressers

There I was, hard at work as usual. It was a busy Friday afternoon. Another high profile murder case. Same MO as the last. The victim was tortured with lacerations all over his body. Fingernails tore off. Eyeball out of its socket. A gruesome murder. How the killer was able to inflict this much damage, while still keeping the victim alive and conscious enoug...

Holiday Girl

by swbiguy on Jul 18, 2018
Transsexuals & Crossdressers

Everyone says you should go on holiday to get laid. I'd never found that to be particularly true, or maybe I was too choosy to fuck the drunken 18 - 30 crowd. I liked a bit more than a quickie with some chubby office girl spending her money on cheap Spanish booze and so desperate to get a suntan she ended up looking like an under-cooked steak. I prefer a c...

A Christmas Surprise

by jerrycross on Apr 10, 2018
Transsexuals & Crossdressers

As the 24th of December came about like it does every year, the gifts under the tree began to pile up. There was just my girlfriend and I, but the amount of presents under the tree this year was unbelievable. Although I'm not one to shake and guess what they were, the excitement was really getting to me. I was like a kid again, hardly able to contain my exci...

White Boi Learns his Place Ch. 04

by sissyashley4bbc on Aug 7, 2018
Transsexuals & Crossdressers

It took me a few minutes to recover from the fucking Daddy just gave me at the mercy of his big black cock. I was definitely handling his size better than when this whole ordeal started, but he still stretched me to my limits. As I laid on his chest, his big black cock softening in my boi pussy, I couldn't help but think about how I have been missing out o...

Quenching Thirst Ch. 02

by PutItInMyMouth420 on Jul 10, 2018
Transsexuals & Crossdressers

So there I was covered in Black mans jizz and piss, handcuffed to a handrail in a gay strip club. I was hard as a rock at this point and had realized in the midst of my humiliation that the sexiest part of all of this degrading shit was my lust for Mr. Warden. I wanted to know how it felt to truly give myself to a real man. Even though my ass was virgin, i w...

A Surprising Change

by chrissycockslut on Jul 10, 2018
Transsexuals & Crossdressers

This all started several years ago, as I finally turned 18 years old. That was when I discovered it, and it completely turned my life around. I had graduated high school the previous spring and my birthday was the first weekend after I moved into college. Now it's safe to say I wasn't the most popular kid in my high school. Fuck, I don't think anyone anywhe...

Mom's in Town Ch. 24

by 1sfshermale on Jul 10, 2018
Transsexuals & Crossdressers

Editor's note: this story contains scenes of incest or incest content. *** Brianna, with her gurl friend/roommate beside her, make their way into the hotel. She sees Juan, last night's doorman, again on duty and notices a glint of recognition in his eyes. "Evening ladies. Welcome back. You look lovely tonight." he offers with a smile directly at Brianna....