Shemale Fucking Guy Stories

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Crystal, Meth and Me

by MrStaggerLee on Sep 11, 2017
Transsexuals & Crossdressers

Author's note to the reader: The objective writing this story was to capture a really seedy and sordid encounter involving a few men and a transsexual prostitute. The story is sexual in theme and could be considered erotic by some, but it's also pretty dark and bleak. You have been warned... I wasn't sure I remembered the last time I had seen Crystal stra...

Sister's Shemale Friend

by silkstockingslover on Sep 12, 2018
Illustrated

Sister's Shemale Friend Summary: Family seduced and dominated by an irresistible shemale. Note 1: This is a Summer 2018 Contest Story so please vote. Note 2: Thanks to DarkBreezly for creating the pictures in this story. Note 3: Thanks to Tex Beethoven, Robert and Wayne for editing this story. I came home from work a couple hours early, as our manager...

Create a Shemale

by wsauthor on Sep 29, 2018
Science Fiction

*Author’s note: This story is Public, if you have an idea, start writing!* Robots, science and chemistry have all advanced further than the public is aware of. Due to patents and trade secrets, nobody knew it was even possible to create a sex bot. They can have gravity defying shapes and sizes. They can even alter their owner with chemical cocktails. Cockbot...

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The Shemale Possession

by SexyKate69 on Dec 12, 2018
Transgender & Crossdressers

I was in another day in the laboratory, arranging the experimental machines. It would be an ordinary day if it were not for one of the machines that went into overload and exploded, after the explosion I opened my eyes and I was scared to see myself stretched out on the floor. How could that be? There was only one explanation, I was dead, that's when I notic...

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...

Neighborhood Good Boy

by Kami107 on Feb 13, 2020
Transsexual

Brian had recently turned eighteen, he was finally a man. Although he didn't quite feel it. He was much smaller than the other boys around his age being only 5'4" and weighing in at a measly 120 lbs. With black hair, pale smooth complexion, skinny but proportionate limbs and wide hips that contoured his firm bubbly butt, his effeminate features didn't q...

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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...

The Deviants' Room

by sissyrikki17 on Oct 14, 2017
Transsexuals & Crossdressers

Upstate New York, 2007 - Day 1 They all kept talking—bitching—about "sloppy seconds" but if you're drunk enough, and these guys were drunk most all the time, you don't really care about dipping your wick into a hole filled to overflowing with other guys' junk. You just stick it in, numbly hump for a few minutes, then make your own delirious contribution to...

The Society Ch. 04

by Barno on Sep 13, 2017
Transsexuals & Crossdressers

I have a little explaining and an apology to make. The last installment of The Society, called The Society part 4 was uploaded by mistake. If you are following this story you will find that the first part of this installment is very similar to part 4. Please take this story for what it is, parts 1 through 3 and then followed by this installment, part 5. Sorr...

Pam's Shemale Experience Ch. 04

by majicman21 on Sep 12, 2017
Transsexuals & Crossdressers

Neighbors strolling by the residence of Pam and John believed the day to be one like any other. It was a Saturday, balmy and humid; nothing out of the ordinary had happened or most likely would happen. Some neighbors knew that John was away for the weekend, and that the children had gone to visit their grandparents. Those same neighbors also knew that a frie...