Shemale Fuck Male Stories

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Orientation
Length
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Infinite Scroll

Size Matters

by idahoboy on May 5, 2015
Science Fiction

Adam rushed into his room after school. His dick was already straining in his pants. It seemed like it was getting harder and harder to make it through a day of school without jerking off. The young man had taken to blowing a load in the toilet at lunch. Today, he couldn't find an empty stall before the bell rang. The boy dropped his pants wrapped his hand a...

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Mistress M Pt. 03

by humblersub on Mar 2, 2020
BDSM

He was once again in her bed between her legs. He had lost track of her orgasms at about twelve. She was way past that now. He had also lost track of time. He never tired of making her cum. And she never tired of him being between her legs. She had given him increasing license to do what he wanted with his tongue and fingers when he was between her legs. He...

RWBY Futa

by AegisXP on Jun 15, 2018
Transsexual

Welcome to RWBY Futa! This is a collection of stories where you, the reader, get to have some intimate encounters with the various women of Remnant. Is what you're looking for not here? No problem! We are accepting submissions for any and all types of scenarios, so long as you follow the story's guidelines. Thanks for reading, and happy fapping!What's next?...

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Snowfall Seduction

by pantywriter on Sep 14, 2017
Transsexuals & Crossdressers

Early in the semester, the professor of Modern European Literature asked everyone where they were from, and whether they would be going home over either Thanksgiving or Christmas. Evan was from Arizona and already knew that his parents were planning on spending Christmas abroad. But the timing had not worked out for him with the start of classes, so his pare...

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...

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 Sexiest Shemales Ch. 01

by cleanly_shaven on Sep 13, 2017
Transsexuals & Crossdressers

When I wake up in the morning, I wake up next to the sexiest shemale in the world...right after me, of course. I woke up this morning next to Holly, my beautiful shemale girlfriend. She was still sleeping in our big bed. The sun was shining in on our bed with our white sheets and white comforter. She was naked of course, except for a bright pink g-string....

She Thong

by mrstanley on Sep 16, 2017
Transsexuals & Crossdressers

Her name was Cindy and she had been born a male. Cindy was a beautiful woman is every way except one. She didn't like the term tranny and preferred being referred to as a shemale. She was truly happy living as a woman. She began taking light doses of hormones at 19 she had stopped hormones because she had difficulty maintaining a full erection. Cindy was bru...

Have we met before?

by HYjaCK on Jun 1, 2020
Bisexual

Light shone through the curtains, blinding you momentarily as you sat up, taking in the environment around you as there's a knock at the door. Struggling to think, you stand up automatically, putting on a discarded red robe and staggering to the door. Leaning against it, the door knocks once more. "H-hello? Room service!" A female voice from the ot...

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Since that day....

by Ssrd33 on May 5, 2019
Transsexual

The weekend I finished and my whole body felt heavy, my ass felt more open and empty at the same time, I slept all the rest of the day. The next morning I woke up and had Melany's penis full of milk, I took it out and I felt that my mouth was very sticky, I went to the bathroom to take a shower because I could only smell the semen all over my body. When I ge...

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