Surprise Shemale Stories

136,276 results
Orientation
Length
Source
Infinite Scroll

My New Neighbours

by csm1967 on Dec 12, 2018
Transgender & Crossdressers

The house next door had, for the past 15 years, been a rental property, mainly for members of the defence force. Neighbours stayed not more than 2 years and some seemed almost gone overnight. Tenants ranged from singles, to couples, to families with children. The place had been empty for a couple of months since the previous quiet couple, and their noisy dog...

Alpha Gamma's Secret Ch. 3

by Wannabe Chick on Sep 11, 2017
Transsexuals & Crossdressers

-7- "This has been an important and exciting year for our sorority," said Jessie, House President, to the assembled sisters of the Northeastern University chapter of Alpha Gamma Tran. Today was a very special day. It was the annual Commencement Ceremony which marked a successful end to the school year. All the girls had gathered in their sorority house's sp...

A Shemale Shock: A MILF Falls

by silkstockingslover on Sep 25, 2017
Illustrated

Summary: Mom catches her daughter with a teenage shemale and.... Note 1: This is a Nude Day 2017 Contest Story so please vote. Note 2: Thanks to Tex Beethoven, Robert, and David for editing this story. I was having a bad day. I'd spilt coffee on myself on the drive to work. I'd gotten a rip in my nylons. And I'd forgotten my notes for tonight's intervi...

The Midnight Alley (continued)

by MrGenius on May 9, 2018
Transsexual

Apologies for making another story. I lost my previous credentials so I cannot continue the previous story. Without further ado, lets proceed... Continuing from: You gasp... There you were, pressed up against the wall and being railed in the ass by this mysterious black woman. Even though it seemed there was no way it could've gotten worse, it had. Your frie...

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Gym Surprise

by standingstones on Jul 6, 2020
Transgender & Crossdressers

I had been going to a certain gym for a couple of years. This place had a lack of weights and machines. I asked the manager if they were ever going to upgrade the place. He said they didn't have any money for new equipment. I soon found a new gym to attend. I really liked this new place. There were serious bodybuilders working out there. I soon found out I w...

Mark's Surprise Ch. 1

by Kip Carson on Sep 13, 2017
Fetish

Mark had just broken up with his steady girl, Diana 2 weeks before. He was finding it really hard to get over her. They had been dating for almost 2 years, and he was devastated when he caught her in "The Act" with 2 guys from the football team. He saw her car at the hotel, and pulled in to see what she was doing. He stood outside the motel room door, and co...

The Gym Ch. 3

by Kip Carson on Sep 14, 2017
Transsexuals & Crossdressers

The day after they shared his wife, Carl ran into John at the gym. "well, did you enjoy yourself last night?" Carl asked. "My wife sure had a good time, and is asking when you will be back again" he said. "Yes I had a wonderful time, your wife is very hot" John told him. "I'm going to go do my workout, maybe I will see you after while" Carl told John. "S...

The Society Ch. 03

by Barno on Sep 13, 2017
Transsexuals & Crossdressers

Heidi's erect penis was sliding in and out more easily now. When she first mounted me being gentle wasn't her first priority. It was my first match and I had almost beaten her according to the wrestling judge. In fact many in the crowd of 60 or so spectators had disagreed and showed it by booing the decision, it had been that close a contest. This didn't sit...

Connie at an Adult Bookstore Ch. 01

by cmorehead on Sep 13, 2017
Transsexuals & Crossdressers

Disclaimer: The following story is not intended for minors. If you are offended by sexually explicit material or it is not legal in your place of residence, please close the document now. If not, I hope you enjoy my attempt at entertaining you with stories of my adventures. * Let me start by introducing myself. My name is Connie and I am a 40-something tr...

Pool Party Ch. 02

by GuyIncognito06902 on Sep 26, 2017
Celebrities & Fan Fiction

It's time for a sequel and if you like imagining beautiful celebrities as hot, hung dickgirls with big tits and big cocks then this is the place to be. I hope everyone likes it. This story is COMPLETELY fictional and not meant for people under the age of 18. This is all fantasy and not any kind of reality. The story codes for this are FF, FF+, orgy, shema...