Shemale Surprise Babysitter Stories

137,690 results
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...

The Sexiest Shemales Ch. 03

by cleanly_shaven on Sep 13, 2017
Transsexuals & Crossdressers

I woke up laying on Daisy's inner thigh. Her cock was lying right in front of my face. It smelled so good. It smelled like sweet perfume and cum from our previous romp. I smelled it and began rubbing the tip of my nose on it and then slowly I began kissing it. Daisy began to slowly wake up and did her cock. It grew more and more as I continued to kiss it and...

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...

Hot Massage

by william125 on Sep 26, 2017
Transsexual

It's been a busy day at the spa. You decided to stay on working at the spa in your university town over the summer break rather than move back in with your parents. The spa offered an excellent training program for new starters and you found you were a natural. You quickly went from collecting used towels to massaging regular clients. As you wash the oil fro...

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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 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...

Jabba's Shemale Slave Pt. 02

by mkh78 on Oct 8, 2019
Celebrities & Fan Fiction

This story is from the imagination of the writer and inspired by Return of the Jedi. I have used Huttese words in some parts. These are not of my own. *** 1:30 am. Tarno and the Twi'lek shemale prostitute he found and subsequently bought from the brothel's owner, were now quickly speeding across the Tatooine desert. He considered spending the night at a...

Mistress' Shemale Cock Gift

by MasterHornedGod on Jul 4, 2018
Transsexuals & Crossdressers

Mistress strides into the playroom in her usual seductive way, her curvy hips swinging side to side, very large full breasts jiggling ever so slightly even though squeezed together to form a captivating cleavage by her black latex skin-tight leotard. A see-through chartreuse skirt accentuates her luscious hip curves, revealing the french-cut leotard plunging...

Healthy Behavior

by BrettLynn on Sep 16, 2017
Transsexuals & Crossdressers

Yes, it's a new series, fans of mine. I know you like Marilyn, but she's on hiatus. Deal. Anyway, I do have something interesting for you. It's an unusual tale, but then again, my writing tastes have proven to be a bit unusual. I'm about as mainstream as N'Sync is underground. So without further ado, let's get started. Oh, and yadda yadda yadda over 18 to re...

Saving The World Porn Review #1

by vic_elor on Sep 16, 2017
Reviews & Essays

Since I seem to have sufficient free time and a steady access to pornographic material, I have taken it upon myself to save the world from bad porn! How am I going to do that you ask? By watching lots of porn, jerking it a few times to clear my head, and then give it either my thumbs up or thumbs down. My system of review will be fairly simple. I will pro...