Shemale Massage Stories

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Orientation
Length
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Infinite Scroll

When Sara Met Bob Ch. 04

by yellowfrog on Sep 14, 2017
Fetish

PART IV: Sara sculpts Bob's lovely penis Days turned to weeks, weeks turned to months and Sara derived ever-growing joys from milking Bob's prostate. The implanted micro-devices gave Sara the ability to massage his prostate remotely, be it from a distance in the same room, to the other end of the bar at the shemales saloon they frequented often, and even ov...

Becoming Victoria

by Writer345 on Sep 18, 2017
Transsexuals & Crossdressers

Prelude. I was happily married and still am, but things have changed; or should I say that things have been changed - I have been changed. I was or rather am still wed to Anika, a rather dominating Polish lesbian, who married me for reasons of her own that are still a mystery to me. I'm not the man that I was...Oh, this is so confusing I'd better start at...

Shemale First Time

by Canine51 on Sep 13, 2017
Transsexuals & Crossdressers

First time Sex with a shemale. Intro. I have read several stories of first time sex with Transexuals and none relate to my experience. So for those who are truly curious about how to go about it and what it is like this is my tale. I have always been a straight guy as far as I know. Married for over 15 years and never strayed once. Early in my life I was...

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...

Small Cock Frustration Pt. 02

by jamtby on Oct 7, 2019
Transgender & Crossdressers

Despite the relatively short distance to my home from Mistress Alexa's club, it seemed like it took hours to get home. The bulge in my pants demanded release but remained restrained in my new panties. It felt strange but all I wanted to do was get out of my clothes. Finally, after what seemed like hours, I arrived home. Once inside I stripped off everything...

Ex-Cellmate Looks Him Up

by SugarandSalt on Sep 11, 2017
Transsexuals & Crossdressers

Everything was going to be perfect. Nathan hummed an upbeat tune to himself as he set the table. His girlfriend would arrive for their dinner in any time now. Nathan checked the food simmering on the stove for the second time in as many minutes. He heard a knock at the door. "Be there in a minute," Nathan called out from the kitchen. He quickly ran a comb...

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...

One Piece Foot Journey

by sofly on Apr 25, 2015
Fetish

Your eyes, wincing as you look out into the distance sea as the sun reflects of its surface, "Is that them?" you think too yourself. In the distance you can see a small outline of what looks like a ship. Everyone too has spotted this in the distance as you hear a huge uproar behind you. "Its them!, the Straw Hats are coming" the screams b...

Open in Reader

Sex therapist

by qaz on Sep 1, 2016
Miscellaneous

Who do we follow?What's next? A boy A girl What's next? A boy A girl...

Open in Reader

2016 Literotica Reader's Choice Awards Winners

by Literotica on Sep 16, 2017
BDSM

The stories and authors below were chosen by our readers as the best of 2016, in voting which took place here. Though these are not the only wonderful authors and stories on Literotica, they are worthy of praise and recognition. Thanks to all of the writers for providing us with hours of hot reading, and to all of the readers for your input, support, and a...