Shemale Boss Stories

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Family Duties

by Thepervertedgeek on Oct 24, 2020
Transsexual

Dear diary, Lol what am I saying, me a XX-year-old starts off this with "hello diary", my chores must be getting to me. Anyhow, hello future me, or whomever finds this, the reason I began to write here is because recently some strange things had begun to transpire here in my home.Writing about it will help me mentally, so for the next few years I w...

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A Shemale Attack: Vennomous Vol. 01

by Vennessa on Sep 12, 2017
Transsexuals & Crossdressers

The near twilight calm of late afternoon was suddenly ripped apart by the deafening rumble of what sounded like thunder close to the ground. Glass, metal, concrete, body parts and other debris blew out from the front of the bank across the plaza shrouded in a ball of smoke and fire. People in the plaza ran for cover, shocked by the suddenness of the explosio...

Working Late with Maggie

by mightymax1234 on Sep 12, 2017
Transsexuals & Crossdressers

Hello, I want to tell a story...my story, about my first love with a shemale who just happened to be my boss. I worked at a bed, bath, and beyond store. I had worked there for about 1 year and a half, and my boss really liked me. I always went and picked up her lunch with mine, never messed up. Her name was Margaret, but I always called her Maggie. In fact,...

Pam's Shemale Experience Ch. 10

by majicman21 on Dec 2, 2019
Transgender & Crossdressers

Pam woke up, and as she remembered what day it was, a smile crept across her lips. Earlier in the week, her owner had decreed that she would not fuck Pam until Wednesday. That had been Sunday night, and now, with Monday and Tuesday past, today would be the first time in a long time she would feel that magnificent cock opening her up. It's been too long.....

Pam's Shemale Experience Ch. 08

by majicman21 on Mar 11, 2019
Transgender & Crossdressers

Content warning: one scene with a golden shower... Pam woke with a start. It took her a few seconds to hear her alarm ringing. Next to her, Tanya was still asleep, and further down on the bed, Alex was as well, her head resting on Tanya's thigh. Pam reached over to the bedside table and quickly turned off the alarm. Neither of the other women stirred....

Pam's Shemale Experience Ch. 11

by majicman21 on Jun 1, 2020
Transgender & Crossdressers

Content warning: one scene with a golden shower. "Ah, what a way to start the day," Tanya sighed, letting her cock slip from Alex's pussy. The shemale had just filled it with a load of cum, dribbles of that gift already leaking out. Pam smiled from next to them, at the possessive yet affectionate way Tanya slapped her cock onto one of Alex's thighs and...

Shemale Utopia

by Lewd_Ruby on Jun 15, 2016
Transsexual

*De-De-De-De-Deep* *De-De-De-De-Deep* *Click* I gently pressed the large red button atop my alarm clock to stop the annoying racket of those high pitched beeps. Sitting up I began to take a look around at my surroundings, Beige wallpaper spread across the walls, the odd video game poster stuck on lazily with some blu-tack. Letting out a small sigh I swung my...

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The Gym Ch. 4

by Kip Carson on Sep 14, 2017
Group Sex

John arrived at Kate's house at 6:50 pm. She answered the door in a very tight fitting short dress. "Damn, you look good" John told her. "Sorry I'm so early, but I was so excited about tonight" he added. "That's fine, I'm always ready early" she said. "And you look pretty damn good, too" she added. She eyed him up and down. He was wearing black dockers, a ni...

Por que

by Ssrd33 on Apr 22, 2019
Transsexual

We're all super, for some reason my mouth felt tired and had a taste, my ass hurt, the other night we were having a great time on a record. It's the only thing I remembered from the other night. Suddenly the teacher said that a new student was going to enter. We were excited by a new student, fresh meat. The teacher said that his name was Melany, for some re...

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Compromised Pt. 03

by HorribleHenry on Oct 5, 2020
Transgender & Crossdressers

COMPROMISED PART THREE CHAPTER EIGHT Park Green Private Hospital specialised, and probably still does, in mending wealthy people, particularly those with kinks. There was nothing that people did to themselves, or each other, that fazed the dedicated staff of the hospital. A patient with a torn arsehole caused by anal sex was very low down on their list of...