Tranny Surprise Stories

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Orientation
Length
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Infinite Scroll

Talk to the Pussy

by KatPissinger on Feb 4, 2020
Transgender & Crossdressers

"Miss Bartlett?" The young woman held the door wide open. She was wearing the formal dark suit of Deborah's personal servants and her curly brunette hair was pulled up straight into a bun. Ruth sighed and gathered her things, holding a tablet in one hand and a bag in the other. She had been waiting in one of the large, luscious empire armchairs in front of...

Tranny Tales Ch. 08: Driving Miss Daisy

by erectus123 on Sep 15, 2017
Transsexuals & Crossdressers

Please note-- this story contains graphic sex descriptions between participants who are over the age of 18. All sex scenes described are consensual. ***** Tranny Tales #8--PreOp Tranny Sub Gets Gang Banged I wasn't always gay, or a Tranny for that matter, although it's turned out that way for the moment. I dated in college, even pinned a girl named Rober...

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...

Who Killed Jenny Schecter? Ch. 15

by OGSalli on Jun 9, 2020
Novels and Novellas

Chapter 15 Divided Highway "Okay, pull over here," Detective Sgt. Collins said. Lauren put on her hazard flashers and pulled off the road onto the shoulder. "Be careful getting out," Collins said. "They'll clip you." The shoulder was wide enough for Lauren's cruiser, but just barely. Collins and Carmen, who was riding in the back, carefully opened their...

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...

O Is for Olivia

by BethanyJ on Sep 16, 2017
Transsexuals & Crossdressers

"OK Oliver. Are you sure? REALLY sure?" I looked at Gina. The question, THE question. But I was sure, after two years of vaguely thinking about it and then six months of researching and consulting, and seeing my doctor and then the therapist he referred me to and then two other therapists - I was sure. Bite the bullet, do it now. It had to be done. "Yes. T...

Samantha Meets a Dom Master

by SamanthaSatine on Sep 16, 2017
Transsexuals & Crossdressers

A true story - I am the main character and all the various activities described were undertaken with my consent...no harm came to me in any way... ***** The date was fixed. The room was booked – neither of the willing parties could accommodate, a not unusual event in the world these two inhabited from time to time. The morning of their meet had now arriv...

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...

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...