Chastity Crossdressers Stories

18,166 results
Orientation
Length
Source
Infinite Scroll

Finding My Shemale Goddess Ch. 02

by TheGuyInBlack on Sep 14, 2017
Transsexuals & Crossdressers

Thanks everyone for the feedback on the last story, I tried to take all of it into account while writing chapter 2. I noticed that some people wanted the story to be longer so I added in a few extra scenes in this one, as well as adding two new characters. As always, any feedback or constructive criticism would be highly appreciated and encouraged. Thanks a...

Can I Be This Lucky?

by Lowendtheory on Sep 14, 2017
Transsexuals & Crossdressers

I had just broken up with my wife of 4 years. So I was definitely not feeling good about myself. My time in the Navy was just about up, & not a second too soon. Now that I was done with my wife, I had no reason to stick around here anyway. I decided to go check out a movie to get my mind off things. I had been mindlessly walking for the past 2 hours, so I wa...

The Farm Ch. 03

by ashmadison on Sep 13, 2017
Transsexuals & Crossdressers

CHAPTER 3: REFECTORY Georgie Suxcock has a name to live up to -- and a personal trainer all her own to help her practice! Dirk Shattler is one of the Fun Farm's assessors, working hard (quite literally) to ensure that the Farm's guests and patrons are fully satisfied. The door slid back, and I walked out -- a little unsteady in my high heels. Dirk wolf...

The Good Doctor Ch. 1

by Rebecca on Sep 11, 2017
Transsexuals & Crossdressers

Being in the medical community, I hesitated about telling my story but decided as long as I left the location out and changed the names it would be impossible for this story to be linked back to me. Being a fairly hi-profile plastic surgeon in a town where cosmic alterations were made famous keeps me quite busy and had afforded me many riches. First off, in...

Tilted Kilt Ch. 02

by call_me_dana on Sep 14, 2017
Transsexuals & Crossdressers

Unexpected Visit It was a little after midnight and I was just clocking out from my shift as a waitress at the Tilted Kilt when my cell rang. "Hello?" "Danika? It's Katie." Katie is the nineteen year-old daughter of the woman I'm currently fucking. I met Katie a couple months earlier when she was home from college for spring break. Katie had told her mom...

Imprisoned by My Fantasy Ch. 03

by Jemina004 on Sep 14, 2017
Transsexuals & Crossdressers

Even a month ago, when my wife's feminization plan was well underway, I never expected that one night I would be stumbling my way to a jail cell. Darius was half carrying me in the basement of the police station. My hands were still handcuffed behind me, and Darius had a grip on my upper arm. My stillettoed feet couldn't really keep up with his long strides,...

How I Became Sissy Willow Ch. 02

by willow619 on Sep 12, 2017
Transsexuals & Crossdressers

"Now the preliminaries are over, and it's time for the entertainment part of our evening!" That was what Fern, my wife, said to me as I lay on the bed after I had been fucked by our newly mutual lover, Jason. I was dressed in pink panties, bra and slip, and a floral sundress. A blonde wig with long curls was on my head, completing the transformation. Fer...

Sisters Forever Ch. 02

by Ginita on Sep 16, 2017
Transsexuals & Crossdressers

It makes no difference if a man is a stallion blessing to women or a conversely if his cock resembles little more than a clitoris. He will know every detail of his cock intimately. Every vein, bump, mark, ridge, dimension and pleasurable sensation is a fascination to him and he is intimately connected to all knowledge of his cock. With this in mind I must t...

Caught at Lunch

by BmthAdmirer on Sep 13, 2017
Transsexuals & Crossdressers

Only so long can you hide, if you are wondering what the hell I am on about then let me explain. As a part time transvestite dressing is always a thrill as is the joy of turning myself from a very average looking guy into a sexy cock loving slut, but due to where I live the chances to fully dress and enjoy the company of other trannies or guys was difficult...

The Virus

by bad_boy_good_girl on Sep 14, 2017
Transsexuals & Crossdressers

If it is illegal to read this where you are from, don't. If you are legal and enjoy the story please send feedback. * It all started with a bit of dust wiped on a subway handrail in New York City. The man who did the wiping came from Iran, though Turkey and into London. The dust was smuggled in the cotton stopper in an aspirin bottle. The first commuter t...