Chastity Tranny Stories

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Master is Going to Cum Now

by Manndee on Apr 28, 2020
Transgender & Crossdressers

I had searched online for months to find a friendly like-minded group of people that I could communicate with and share my unique desires. I thought I had seen them and signed up to several dating type agencies that offered me the perfect match. The agencies then sent me non-stop emails from people that matched me. The people were not interested or simply di...

Miss Chianti's Troy-Boy

by justincbenedict on Feb 26, 2019
BDSM

Chianti finished brushing her hair and gave it a cursory look, and the doorbell rang. Chianti put her brush down, and pulled the scoop neck of her pretty pink sundress down a little, just so the jugs poked out a bit more. The bell rang again. "I'm coming!" What a beautiful dress, sleeveless and so short. Purchased by Ingersoll, a sad little man who needed...

Caught In the Tranny Master's Web

by CarrieQ on Sep 16, 2017
Transsexuals & Crossdressers

One of the nicest things about living in London's West End is how you can look out of your window at all the glitz and glamour, and feel like you're right in the middle of something big. And if something as big as Kurt's 14-inch cock happens to be pounding in and out of you while you look, then doesn't that just take the biscuit? An over-endowed black Germa...

Wandering Gem

by dkleiman87 on Sep 15, 2017
Sci-Fi & Fantasy

The ruby glowed in the stores fluorescent lights of the old thrift shop, shooting beams of red against the countertop as James walked by. The glint of light catching his eye as he passed, drawn into its radiance he reached out and gasped at it. "Excuse me?" he asked the woman texting behind the counter, "How much is this?" The girl unenthused by her annoyi...

Black Women Love Transsexuals Too

by Samuelx on Sep 16, 2017
Transsexuals & Crossdressers

A lot of girls out there are turned on by transsexuals, and I'm one of them. My name is Raquel Dawson, and I'm a young Jamaican woman living in the City of Ottawa, Ontario. I study psychology at Carleton University, and I'm a gal with a pretty ordinary life. My family moved to the region of Ontario, Canada, from Kingston City, Jamaica, in the summer of 2007....

My First Time with a Tranny

by daddydick89 on Jun 4, 2019
Transgender & Crossdressers

This is a true story. It happened on a Monday morning, after waking up with a throbbing hard-on. I called up my regular booty call. But she couldn't make it, because her husband stayed home from work that day. So I decided to browse Craigslist, looking for someone local. After posting my ad, looking for NSA sex, I sat back and waited. Within minutes, I re...

ESTIM Experiences Ch. 02

by jy55 on Sep 12, 2017
Toys & Masturbation

Since my first story, I have developed into a real estim freak. My daily pleasures are such that my body almost 'knows' that it is time. I generally masturbate every morning anyway, but estim is almost always the usual method. I have taken to looking at online porn the whole time as I stimulate myself for at least an hour daily. The sensations are so exqui...

Punishment for my Tranny Virgin

by Creamyirish on Sep 16, 2017
Transsexuals & Crossdressers

He and I know each other very well, though we live in separate states. I shared a rape fantasy with him that was to happen when he came to visit me. Instead, he caught me off guard when I visited him and he raped me. I fought and fought but he had more strength and he raped my pussy and raped my ass and left me bruised and bleeding. We share many fantasies...

Private Eye's Birthday

by Selbryth on Sep 16, 2017
Transsexuals & Crossdressers

In the dimness of the evening light, it looked like two pale bodied women sitting together on the couch. Al could see them quite clearly now through the three story high plate glass windows of the estate. They sat there watching the sun going down. He thought perhaps they were really dedicated sun worshipers because they sat there with almost no light, compl...

Greg Tries a New Angle Ch. 02

by kjherts on Sep 15, 2017
Transsexuals & Crossdressers

In part 1, Greg posts a selfie in his ex-wife's panties to lure a man's man on an adult dating site. To his delight, he meets Drew, who talks lightly but carries a big stick. Earlier in the afternoon, Drew unloaded in Greg's mouth, with the promise to return that evening to take care of unfinished business... ***** It was approaching 10 pm and three candle...