Shemale On Guy Stories

702 results
Orientation
Length
Category
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2026 SmutMD.com
Create your own smut fantasy with AI

Her

by St_eve on Sep 16, 2017
Fetish

I could never say no to Her, I was helpless, if She said frog, I jumped. She called me into the bedroom; She was on the bed naked, lying on Her side, ass out towards the edge. She told me to take off my clothes and play with myself. I started slowly, looking at Her bare backside, the side of Her breast, Her long dark hair and finally at Her ass. She could se...

Master PC - NYC Edition Ch. 29-END

by Sementix on Jan 22, 2019
Sci-Fi & Fantasy

Twenty-Nine When Nat approached his apartment door (after entering his building from above not below), he smiled and prepared himself for a small harem of woman on the other side. It was about seven p.m. and he had set a dinner reservation for 8:30. That was plenty of time to wind down a little bit and then get changed, etcetera. He opened the door. As he...

Sensations

by beau_thwayz on Sep 16, 2017
Sci-Fi & Fantasy

They had been friends for 20 years, & in all that time he had felt attracted to her. They'd had many long conversations about sex over the years, yet had never acted upon them. When he tried to start something up, she often seemed stand-offish, & sometimes shy or even afraid of him. Figures. He should have never told her so much about his fantasies. Yeah, it...

Dick World

by darkness_drearing on Dec 25, 2019
Bisexual

For contributors As was stated at the top: while there were will be two general threads to go off of (for a guy and girl), feel free to create your own characters or scenarios. The only shared premise among them needs to be that they find themselves, however you decide that happens, in this universe and, as The Eagles would say, "You can check out any t...

Pegged for Love

by silkstockingslover on Jan 31, 2018
Fetish

Summary: Straight guy is pegged by the girl of his dreams. This is a 2018 Valentine's Day story so please vote. Thanks to Tex Beethoven, thor_ph, Robert, and Wayne for editing. Pegged for Love It is probably the truest saying in the world: you can't just be friends with a girl of the opposite sex. I mean it may be possible when you're an adult or marri...

BBC Lover's Interview on Stage Ch. 03

by ndeavour on Jan 29, 2020
Interracial Love

The past 9 months had been a very wild time for us. "Us" is me, Nancy Wladczyk, and the other part of "us" is my husband Ted. While I figure that anyone reading this on Literotica can find out about me by reading the first two parts of this, and, even though I don't get a damn thing out of it as an amateur author, you SHOULD read them since I don't really...

Life for Futa

by GCStarnen on Jul 22, 2018
Fetish

Disclaimer: This story is the story "Living in a Futanari society"/Shemale Worldo but kind of reborn, somethings in the story have been edited here and there and some characters names and traits they have might also change from the original. (Such as the mothers name being changed). Also this story is hugely inspired by Futanari World/Shemale World...

Futanari World

by styxmaster on Apr 16, 2016
Fetish

You wake up this morning to the sight of your younger sister Sarah pulling your covers off of you. "Get up Doug, you don't want to be late for school." You get dressed for school after Sarah leaves your room. you never mind school that much, you mostly get B's and A's in your classes but given the opportunity you would like to just stay home and wa...

Hooker Addiction

by Antarctica77 on Apr 22, 2025

So my whole life I had this weird fetish. With my upbringing, how I was taught, I had subdued this fetish for the longest. And I am not sure if it is a fetish, or more wicked curiosity spurned onto me from watching porn. I remember the first time I sorta discovered my predilection for this sorta porn. It was when I was eighteen years old. I had clicked the w...

Accommodating Neighbors Ch. 04

by gentlegem on Sep 14, 2017
Mature

Chapter 4 Our Visit to the Adult Toy Store (Authors Note. This is the 4th story in a series. For those of you who haven't read the first 3, it is based on the relationship of a 44 year old red haired lady and a 63 year old man who live in the same apartment complex. Much of it is based on true characters and events.) * Becca and I didn't see each other f...