Shemale Surprise Babysitter Stories

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The Arms Of A Woman

by Samuelx on Sep 13, 2017
Transsexuals & Crossdressers

San Francisco. Mariah walked out of the Bordello. She was getting sick and tired of that place. Sick and tired of working endlessly to satisfy the depraved desires of those people. How she loathed them. Since she began working at the Bordello, she had seen a side of humanity she had never thought was possible. The worst imaginable side. She was just anoth...

Classroom suprise

by william125 on Mar 10, 2015
Transsexual

A recently qualified teacher, today is your first day at Tower sixth form college. You stand at 6' 2" and keep your self in good shape. On your way in this morning you saw a group of girls giggling and looking at you. Obviously talking about the new teacher. The bell rings and a little nervous you welcome in your 18 and 19 year old students. Note to r...

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BORG Collective Pt. 02

by bladeday on Feb 3, 2020
Transgender & Crossdressers

Prologue In my first story, BORG Collective. I had stumbled upon a chat group obsessed with Star Trek Voyager. Their interests were the BORG Collective. After two nights of interaction in a chat with ten people, they invited me to a Cosplay party. At the party I could join, I had to swear to serve the needs of the Collective and follow all orders given, wit...

"A Shemale Submission": A Lust Story

by silkstockingslover on Dec 23, 2019
Illustrated

"A Shemale Submission": A Lust Story Summary: Author Jasmine falls for a hot new teacher with a big cock. Note: Thanks to hfernandez1983 for the many pictures used in this story. He spent weeks getting these perfect for the many different scenes I requested. If you like the pictures in this story, please feel free to read the multi-chaptered series Cheerle...

The Sexiest Shemales Ch. 02

by cleanly_shaven on Sep 13, 2017
Transsexuals & Crossdressers

Holly and I didn't want to waste our day so got up and got ourselves in the shower. We stripped off our g-strings that we were still wearing from our sex fest and turned on the hot water. We always shower together. Sometimes we will fuck each other in there or suck each other off but we just had sex so we just soaped up each other's bodies and cleaned the cu...

Shemale Shock Continues

by standingstones on Sep 12, 2017
Transsexuals & Crossdressers

I met Cheryl at a party thrown by my sister. I asked Cheryl to come to my place afterwards and she agreed. That was where I discovered Cheryl was a shemale. I did something I had never done before. I sucked on Cheryl's cock and I took her load down my throat. After that I ended up fucking Cheryl's tight ass and giving her my own load of cum. We had now been...

The Making of an Angel Pt. 01

by AngelLawrence on Jul 29, 2019
Transgender & Crossdressers

This is part biography and part reminiscing. I've changed names to protect people's identities and skewed some of the locations to make it difficult for people to be identified. All persons are over the age of 18 at the time of what happened. I wish I was still 18... I would have had my surgery much earlier! ***** My name is Angel Lawrence and I'm a 48 ye...

ShemalePrey.com

by Wazzfup73 on Apr 24, 2019
Transsexual

(Apologies that this is not in the Guidelines, but the term 'shemale' is used only for the purpose of erotic fiction and should not be as a term or to represent trans women in real life. Apologies to any people it may offend) As the alarm clock goes off on my phone and your mom shouts your name 'Ryan' to come down for breakfast I jump out off bed to look at...

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The Sex Star Ch. 01

by pinata on Sep 12, 2017
Sci-Fi & Fantasy

Priscilla awoke to the pleasant sound of a woman moaning in lust. She had been a lesbian all of her adult life, and the sound of a woman about to cum immediately made her juice up. She opened her eyes and looked around the room. There were several other women in there with her, and all of them were very attractive and completely nude. Most were still asleep...

Journey to Trans Submission Ch. 01

by bluev on Jul 15, 2020
Transgender & Crossdressers

It has been at least thirteen years since I first discovered my kink and one year since I started to think about making it come true. This is a kink I have not shared a word with anyone for a fear of being judged and a fear of being told that it was not right to indulge in such objectification. Finally I came to the point where I said "screw the world, it's...