Shemale Babysitter Stories

4,301 results
Orientation
Length
Source
Infinite Scroll

Tribal Ecstasy Ch. 01

by icemania on Sep 16, 2017
Transsexuals & Crossdressers

Denise pressed her hands as hard as she could over her ears as she tried to block out the low thunder of drums and the faint shrieking moans that had become her only companions. Her head still throbbed a little from the injury she had suffered in the car crash, but it hardly figured on her list of concerns right now. She had woken up here in this dark musty...

A Night with a Sexy Shemale

by MajesticLVR87 on Sep 13, 2017
Transsexuals & Crossdressers

This is a true story which goes deeper into my explorations of my sexuality in my younger years many people may not have the guts to share so much about their past I don't have that problem because I have met the love of my life and plan on sharing the rest of my life with her my adventures with other partners or random partners is over I have settled down s...

Shortening His Sentence Ch. 02

by SugarandSalt on Sep 11, 2017
Transsexuals & Crossdressers

I knew when writing the first chapter that I'd get around to writing a follow-up chapter. This one definitely requires another installment sometime as well. I mentioned at the start of the last chapter that there wouldn't be tons of sex from the get-go, the same can't be said for this chapter. ;) * Foster's tongue lapped at Miss Julia's cock head. It'd bee...

Three in Bed

by normadel on Sep 16, 2017
Group Sex

From my journal - Ray was out of town. I was horny, so I rented a shemale movie from our favorite adult video shop. When I got home I stripped and laid out my toys and lube for easy access and put in the tape. As I watched shemales having sex, I wondered why some could get hard and why some remained limp. Anyhow, I soon was wet and ready to play. I began on...

Transwood High Pt. 04

by BoobVillian on Sep 12, 2017
Transsexuals & Crossdressers

Christmas is Cumming... Authors note: All the characters in this series are over 18, this is the fourth part of the serious so be nice :-) Sorry for keeping you horny for so long, hopefully this satisfies. The story focuses on our main heroine, and some new/ old faces appear. Enjoy and leave comments! ******************************* 10/12/2016... 'Open u...

Awakening: A Author's Mindset

by silkstockingslover on Dec 19, 2018
Illustrated

PS: Yes I know it should be 'An' and not 'A' to be grammatically correct, but I need it this way to make them stay in alphabetical order for future parts. Summary: Deleted scenes, photos and reasons from Awakening: 7 Slutty Blackmail Tasks Note 1: This is not a story, but deleted scenes with explanation from the story "An Awakening": 7 Slutty Blackmails Pl...

Spicy Story

by TexanBelgianCutie on Jul 17, 2019
Transsexual

Family Kyle had wildly mixed feelings when he saw his mom walking towards him. He kept his feelings to himself however and forced a big smile to welcome her back from the SpringWood Adult Mental Hospice. He had not seen her since he was child, yet he was glad to see she looked healthy and happy. “Hey Sara”, he grimaced, “How are you? Sara had spent the last...

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Adrius' Noble Adventure Ch. 02

by ScumDumpster69 on Jul 6, 2020
NonHuman

Author's note: This chapter contains horse cock, breastfeeding and cum all the way through. (Make sure you know what that means before reading. Reader discretion is advised!) ***** To the far west of the continent of Korilia, the minotaurs ruled. From the taigas in the north to the equatorial grasslands, these huge, bovine beasts wandered the earth, rarely...

Virginia's Luxurious Evening

by JonathanStone on Sep 16, 2017
Transsexuals & Crossdressers

West Palm Beach didn't have many cold snaps, but when one did rake the city the weather seemed twice as frigid as it actually was. Virginia Stanton sat alone in her office on the third floor of Prism Design's building overlooking the Intra-coastal Waterway. She had been chilly all day, mainly because of the dampness in the air; Forty-eight degrees outside wa...

Mistress Coco School Wayward Boys

by tawnysuede on Sep 14, 2017
Transsexuals & Crossdressers

Where Boys Become Girls, Whether They Like it or Not by Mistress Tawny Suede assisted by slave Holly Introduction In Which We Meet Rich Bitch Kimberly and Domineering Mistress Coco Kimberly Caldwell's head thrashed about on the silk pillows; a cry of ecstatic pain escaped her luscious lips as she cupped her heavy breasts, her crimson fingernails ra...