Shemale First Time Stories

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Orientation
Length
Source
Infinite Scroll

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...

Amanda and Me Ch. 01

by Tallnhard1 on Sep 25, 2017
Transsexuals & Crossdressers

I walked in the door of my one bedroom apartment and headed straight for the computer. Lately it seemed like I had the same boring routine everyday: get up early, work all day at my stressful IT job, go straight to the computer when I get home to look at porn and masterbate, then eat dinner and go to bed early. Unfortunately tonight was no exception. As I w...

Amanda and Me Ch. 03

by Tallnhard1 on Sep 11, 2017
Transsexuals & Crossdressers

The sudden ringing of my alarm clock woke me up at 6:30AM sharp. Rolling over I turned it off and then rubbed at my eyes as I began to wake up. Slowly the events of the night before came back to me and I smiled as I thought about Amanda and how wonderful another night with her was. We had great conversations and another round of mind-blowing sex and I wonder...

HypnoSissy: Educated to be Pegged

by silkstockingslover on Aug 13, 2019
Fetish

Summary: Cock sucker's training is advanced to hypno videos on anal sex. WARNING PLEASE READ: -This is a hypnosis story with potentially influential subliminal messages within it. -The story also contains hypnosis video scenes. -So if you begin behaving differently after reading this story and all your friends start pointing fingers, don't come crying to...

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...

Trapped in a Shemale Prison!

by waelator on Nov 12, 2018
Transsexual

The sound of the massive chain link fence closing behind you as you drag the chains shackled to your ankles along the concrete path makes the reality of your situation more lucid. You didn't know what to expect here but your life as an orphan living on the streets prepared you, at least somewhat. You know not to cry, and most of all, to never, ever snitch, o...

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Growth-XX

by FlatCap90210 on May 20, 2019
Science Fiction

James felt as if he was going insane. It was summer, the sun was shining and he was at the beach ogling girls. Tits of all shapes and sizes surrounded him, wrapped in bikini tops, one pieces and other pieces of fabric of varying coverage. James' heartbeat pounded in his ears and throbbed in his crotch, digging a furrow in the sand beneath him. He was lying o...

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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...

Male or Shemale, Still a Slut

by yeaimbored on Sep 11, 2017
Transsexuals & Crossdressers

So this is a 2 part story. Part 2 is strictly shemale and takes place a few years after Part 1. Part 1 is how Brandon became Brenda, although without the "I took bath and did my nails and shaved" stuff because that's not my thing. It's more tranny sex than anything, so if you're only looking for full on shemale skip to Part 2, they're pretty much standalone...

The Sex Star Ch. 08

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

When Kayla woke up, it wasn't in the department store fitting room she had fallen asleep in. She was in a white room filled with bright flourescent light, almost like a hospital or something. She tried to get up, and realized she had been immobilized... leather restraints bound her wrists and ankles, and another, larger strap encircled her torso just beneat...