Shemale Babysitter Stories

4,301 results
Orientation
Length
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Infinite Scroll

futapus complex

by redpulse0091 on Jan 28, 2019
Fetish

Erik walks up to the front door of his home and pulls out his keys from his backpack. Unlocking the door and walking inside he takes a moment to stretch. Feeling relieved that finals are over and he isn't going back to school for a while he starts walking to the kitchen to grab a snack. Grabbing a protein bar and an apple he continues to his room, turns on h...

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Poke-Futa

by Sex-Shooter on Dec 6, 2020
Fan Fiction

A light came upon a mysterious figure, feminine with a bulge between the legs, and the figure waved. Then she spoke cheerfully: Hello there, [Redacted]! My name is Professor [Redacted] and welcome to the [Redacted] region! Before we start, let me tell you about the world. Our world is filled with Pokemon, special creatures that resemble us in terms of body s...

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Amy Finally Lives Out Her Fantasies Ch. 02

by LuvAGoodPegging on Sep 11, 2017
Transsexuals & Crossdressers

(Author's Note: This is a continuation of "Amy Finally Lives Out Her Fantasies -- Shy Amy uses her strapon on Kyle". Thanx to all who provided such great feedback. Hope you like part two. Warning: this story contains male/female strapon sex, cum eating, and as the category suggests, shemale sex. If those aren't your things, you won't enjoy this story. Love t...

Twenty-Two More Questions

by silkstockingslover on Jan 20, 2020
Reviews & Essays

Twenty-Two More Questions Summary: 22 questions asked by readers answered. NOTE: Thanks to Tex Beethoven and Robert for editing. I wrote the essay Twenty Questions in December 2017 and Twenty-one More Questions in 2018. I answered the following questions, in case you want to read them. 1. Are you really a teacher? 2. How often do you wear nylons? 3. Wh...

The Midnight Alley (continued)

by MrGenius on May 9, 2018
Transsexual

Apologies for making another story. I lost my previous credentials so I cannot continue the previous story. Without further ado, lets proceed... Continuing from: You gasp... There you were, pressed up against the wall and being railed in the ass by this mysterious black woman. Even though it seemed there was no way it could've gotten worse, it had. Your frie...

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Amanda and Me Ch. 02

by Tallnhard1 on Sep 11, 2017
Transsexuals & Crossdressers

I rolled over after reading Amanda's note with a big smile on my face. I couldn't believe that after all the time I had spent masterbating to shemales and fantasizing about meeting one it had actually happened. Not only had it happened but it had been the most amazing sexual experience of my life. As I lay there thinking about the night before I was surpris...

Mardi Gras Surprise

by HerLittlePiggy on Sep 12, 2017
Transsexuals & Crossdressers

"Is this what you want bitch?" Tiffany asked sternly as she waived her hard cock in front of my face. "Yes," I hissed as I looked into her dark sexy eyes. "Good answer bitch now open wide and suck my cock," the sexy shemale ordered as she rubbed the head of her cock across my lips. Precum oozed from her cock and coated my lips. I closed my eyes and ope...

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...

Erin and the Shemale

by kimberlykitten on Sep 25, 2017
Transsexuals & Crossdressers

Erin was up bright and early on Friday, getting a good hour jog into her schedule. She didn't have to be in class until two hours from now. As she was jogging, earlier male joggers had passed her by with their eyes directly on her bouncing melons. Even wearing two sports bras and two regular bras weren't enough to hold Erin's gargantuan jugs down. Erin did...

The Society Ch. 03

by Barno on Sep 13, 2017
Transsexuals & Crossdressers

Heidi's erect penis was sliding in and out more easily now. When she first mounted me being gentle wasn't her first priority. It was my first match and I had almost beaten her according to the wrestling judge. In fact many in the crowd of 60 or so spectators had disagreed and showed it by booing the decision, it had been that close a contest. This didn't sit...