Shemale X Male Stories

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Orientation
Length
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Infinite Scroll

Office Punishment

by Chewiebon on Oct 15, 2017
BDSM

Contrary to her name, Sandy had long, brunette hair. She was a little over 5 feet tall, and very skinny and petite. She lived in a pretty normal neighborhood, filled with traditional families with traditional parents and usually around 2 or 3 kids. There were a few singles in the neighborhood like her, but only a few. The moms in the neighborhood were pretty...

Cabin Fever

by mutterguffin2 on Sep 13, 2017
Illustrated

For the past few months I have been been having an incestuous relationship with my two older sisters Becky and Lisa. The last weekend with my sister Lisa left me with mixed emotions. We both confessed to having developed strong feelings for each other that went beyond normal sibling affection. It even went beyond the amazing physical connection that she and...

Young, beautiful, Nurse

by spitzharder on Sep 16, 2017
Transsexuals & Crossdressers

The light was blinding me, the masked figure moved into my eye line but he was just deep shadow, my mouth was open in a silent scream, I could taste the metal pliers that had wrenched the tooth from me but wouldn't give him the satisfaction of moaning, despite the pain. At nineteen I was not the sort to show fear, regardless of the blood pooling at the back...

What It Takes Ch. 01

by YKN4949 on Sep 25, 2017
NonHuman

Dear Reader: This is part 1 of a 4 part story. All four parts are written and will be posted sequentially. This is not one of my "normal" genres (check out my lesbian, shemale, and incest stories). I am not sure if I am cut out for non-human stories, but I wanted a change of pace in my writing. Let me know what you think. If you readers think I have a knack...

Debra and Tom

by murphy621 on Sep 19, 2017
Loving Wives

I was bent over the back of our sofa with my wife's strap on buried deep in my ass. I was screaming, "Yes, yes, fuck me Mistress, I am yours, I belong to you, I am your slave boy." She stood behind me, a big smile on her face as she pounded away, the other end of the dildo in her cunt and she commanded, "Cum, cum, slut boy, cum with me now." And we bo...

Young Sissy Ch. 01

by smittysimon on Sep 19, 2017
Transsexuals & Crossdressers

Author's Note: This is a follow up to The Young Master series. You can start here if you aren't interested in Belle's misadventures as spoiled young man turned out by his own sissy slave and eventually enslaved by his step-father, but it does introduce a lot of characters you'll read about in this series. * I don't know how long I was under...days, weeks....

Cheerleader's Mom: Fucking Her Ass

by silkstockingslover on Dec 9, 2019
Illustrated

Summary: Submissive Mom is trained in orgasm denial and ass fucking. Note 1: Thanks to hfernandez1983 for doing the visuals for this story. Note 2: Thanks to Robert, Wayne, and Tenzin for editing. Recap: In Part One, A POWER SHIFT: 39-year-old mother, Michelle, decides to try on her daughter Allie's slutty cheerleading outfit. Once she has it on, she beg...

The Robertson's Sissy Ch. 14

by Clite69 on Apr 28, 2020
Transgender & Crossdressers

My apologies on my disappearance, life has been crazy. Though this chapter might not have been worth the wait I am sure the following chapters it sets up will. *** Lela and I had spent most of the night cuddled up on the couch. I was woken around 4am by Lela who wanted to go up to the bedroom. In a half sleeping state I followed her upstairs and collapsed...

A Ski Bunny is Born Ch. 03

by Nikki H on Sep 18, 2017
Transsexuals & Crossdressers

Kim and I are thrilled that so many people are enjoying reading about our adventures. We have received so many really nice e-mails from lots of lovely people, its good to know you girls and guys out there are enjoying them! We had promised each other a trip to Europe but hadn't really made any firm plans. Kim and I were relaxing by the sea. We had bailed ou...

Beautiful Men

by Jonathan_Stone on May 7, 2019
First Time

[An Account from the PRISM Chronicles] Chapter 1 An Unexpected Opportunity Huffing and puffing wouldn't make it go away any more than believing that Howard Hughes' enormous wooden aircraft, the Spruce Goose, was a practical way to build a usable plane made it so. His fiancée, Parker Scott, had gone to considerable trouble to get him an interview with a...