Tranny Surprise Stories

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Orientation
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Infinite Scroll

Dirty Black Summer Ch. 03

by Stardog Champion on Sep 15, 2017
Transsexuals & Crossdressers

"Do you have some extra cash on you?" Trina asked from the passenger seat as we headed downtown to meet Summer's Husband. "Why?" I turned and asked. "I told Larry while we were IM'ing earlier that I would bring some blow to the room...as drunk as he was I thought he was just kidding and I told him I'd do what I could," Trina sighed. "It probably wouldn't...

Transsexual Treasures

by dirtyjoe69 on Sep 14, 2017
Transsexuals & Crossdressers

My name is Steve and I am a thirty seven year old divorced male. I am considered good looking. I am very tall standing six foot seven and have a good build for my size. My marriage didn't work for many reasons money, being too young were a couple of them but the biggest reason was sex. I wanted it and she didn't. It always seemed to be a chore for her and wh...

Recruiting of a Sissy Maid Ch. 15

by Sissy_Chantel on Dec 22, 2017
Transsexuals & Crossdressers

Chapter Fifteen: Life Changes but Normalizes Monday morning, Carl and Chantel are up and at it, breakfast in the hotel restaurant and then a shopping excursion to an are Jewelry store for Carl to buy Chantel her engagement ring. Dressed sharply but casually Carl in a white button down shirt, Khakis and black walking shoes. Chantel a white turtle neck, black...

A Sissy's Wish List

by slutty_lucy on Sep 16, 2017
Transsexuals & Crossdressers

Boys, boys, boys. First off, let me tell you that I have a butt plug shoved so deep in my little tranny pussy right now. That might help to explain how depraved I might sound. I really need some cock in my ass right now! I am sitting here stroking my tiny little tranny clit right now thinking of how to best share my desires. I want to be a perfect little slu...

I Wanna Both His Balls

by enfantterrible on Sep 14, 2017
Humor & Satire

The Brooklyn mob boss Joe Slow is sitting in Carlito's slurping on a bulging bowl of meatballs. The restaurant is dark and empty, just the way Joe Slow demands it everyday at the same time. A mobster with a habit like this is a Hitman's dream, but that's another story. So we see the scene and tomato sauce is smeared all around Joe Slow's fat chops, which fla...

Trailer Trash Tranny Ch. 03

by Travel_by_day on Sep 26, 2017
Transsexuals & Crossdressers

Chapter 03: Strip Club Jeannie, a blonde tranny living in a trailer park outside of Omaha, Nebraska, was working as a hooker to try and make enough money to get a boob job and move to New York City. She was working the parking lot of the truck stop just down the highway from her trailer. After an initial night where Jeannie made a good amount of money, thin...

A Glory Hole for Tranny G

by Creamyirish on Sep 13, 2017
Transsexuals & Crossdressers

I am reveling in what a difference almost a year has made. I remember meeting Chris online, exchanging a few funny e-mails, two days after my birthday. No more and no less, just a person somewhere who I had no idea what he was like or looked like, but someone who made me laugh with our e-mails each days, growing into text messages each day, and more. No idea...

Listen to Your Gut

by 36FF_Tiki on Sep 14, 2017
Transsexuals & Crossdressers

This was inspired by a fan, Pantycladlad. He said he liked cross-dresser stories with some rough treatment. So be warned, there is some non-consent action and a little bit of roughess. Like always, I did it all myself, and although I proofread, there may be a few things I missed. There will be some Midwest regionalisms too. I hope none of it stops you from e...

Recruiting of a Sissy Maid Ch. 04

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

Chapter Four: Chantel, Fitting Into Her New Lifestyle. Master Holt says, as the two of them walk out from the elevator on the 2nd floor, "This will be the floor that you will begin your life in servitude to us Chantel. Lets go find your head maid Penny and then get you to your room." Chantel grows more and more resigned to this new life as she see's a very...

Trailer Trash Tranny Ch. 02

by Travel_by_day on Sep 26, 2017
Transsexuals & Crossdressers

Chapter 02: Truck Stop Jeannie grew up poor in a trailer park just outside Omaha. That made it tough at school. So did being born with the wrong gender. She was a girl trapped in a boy's body. Even though as a kid she only dressed up as a girl in private (what little there was of that in the small trailer she shared with her mother), it was obvious to every...