Shemale Boss Stories

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Infinite Scroll

Trip to London Pt. 02

by plez2tease on Sep 17, 2017
Loving Wives

I wake up early Tuesday morning and feel a little excited. Today is the day my husband and his friend have been planning for over a month to make happen. The only part I know about the plan is that I am supposed to dress in what my husband has provided me for the day and that a car would be here at the hotel around 11am to take me to some place. I was told t...

My First Time Out Ch. 01.5

by Shayna on Sep 16, 2017
Transsexuals & Crossdressers

Shayna paced back and forth throughout the entire Suite while she nervously smoked the long thin cigarette. She occasionally stopped and peered into the mirror thinking that all of her hard work had gone to waste for tonight. She was dressed to kill and had no place to go. The red patent platforms with 5” gold colored stiletto spikes. Her long legs encased i...

Mardi Gras Surprise

by HerLittlePiggy on Sep 12, 2017
Transsexuals & Crossdressers

"Is this what you want bitch?" Tiffany asked sternly as she waived her hard cock in front of my face. "Yes," I hissed as I looked into her dark sexy eyes. "Good answer bitch now open wide and suck my cock," the sexy shemale ordered as she rubbed the head of her cock across my lips. Precum oozed from her cock and coated my lips. I closed my eyes and ope...

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...

Erin and the Shemale

by kimberlykitten on Sep 25, 2017
Transsexuals & Crossdressers

Erin was up bright and early on Friday, getting a good hour jog into her schedule. She didn't have to be in class until two hours from now. As she was jogging, earlier male joggers had passed her by with their eyes directly on her bouncing melons. Even wearing two sports bras and two regular bras weren't enough to hold Erin's gargantuan jugs down. Erin did...

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...

Craving Shemale Cock Ch. 01

by jeritza on Oct 22, 2019
Transgender & Crossdressers

I stood nervously on the dark cobblestone alley street, in front of the unmarked door, running through the possibilities in my head, speaking under my breath. I was thinking of all the events that led me to this moment - the perverted path I had gone down. This is it. This is finally happening. No turning back now. Dear god, no turning back now. *** I was...

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...

My Stepmother's Surprise

by sissybr on Sep 12, 2017
Transsexuals & Crossdressers

This is my first story, so I would appreciate some tips and comments. Please enjoy ^^ * My name is Robert, I'm 18, skinny and not too tall. I've never had much luck with girls, in fact I never dated one and I used to spent my days playing games on my computer and watching porn. Shemale porn. Dominant shemales fucking men. I wish i could be one of those men...

Growth-XX

by FlatCap90210 on May 20, 2019
Science Fiction

James felt as if he was going insane. It was summer, the sun was shining and he was at the beach ogling girls. Tits of all shapes and sizes surrounded him, wrapped in bikini tops, one pieces and other pieces of fabric of varying coverage. James' heartbeat pounded in his ears and throbbed in his crotch, digging a furrow in the sand beneath him. He was lying o...

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