Gay Sex Story Surprised Fist Hole Stretch Stories

315,443 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

Fifi La Femme: A Pansy at Last

by pris69696 on Sep 16, 2017
Transsexuals & Crossdressers

I have written this story "Fifi La Femme-A Pansy at Last" mainly from personal experience as a mature homosexual transvestite who was a gay virgin until my early 40s. I hope that it will appeal both to extreme effeminates and the ultra-masculine men they ache to serve. Now divorced I've been living with my boyfriend Ron for three years as his gay wife and ye...

For Passion Conquers All Ch. 02

by TheRisenStorm on Sep 12, 2017
Transsexuals & Crossdressers

Outside the gymnasium the sun had nearly fallen completely away past the horizon, handing over the sky to Luna for the night. The wind had let up some although the breeze continued to toss brown and gray leaves randomly about. Mike and Eli where slowly walking toward the bus stop in the mystical evening twilight. The temperature had fallen a few degrees and...

Your First Flight

by f1dude_lotus on Sep 12, 2017
Transsexuals & Crossdressers

I've always enjoyed stories in which you get to choose the main character, as I've done here (it's set in 1st person perspective but also in 2nd person perspective). I've purposefully made it vague so you can fill in the details to your own liking. Also, I should have mentioned this before but if anyone wants to offer ideas to stories and wants me to write...

Pleasing Juliette Ch. 04

by MTL17 on Sep 14, 2017
Celebrities & Fan Fiction

Disclaimer: I do not own Nashville and have no association with anyone involved in the show. I do not make any money from the writing of this story. ***** For a few precious months Juliette Barnes was actually happy. This was a newsworthy event. Literally. All the gossip magazines and shows had picked up on it, some even correctly guessing the reason for t...

Lisa and Maddie Pt. 06

by Generalgums on Sep 16, 2017
Celebrities & Fan Fiction

If you have any ideas or suggestions about where I take the story or what Lisa and Maddie have to do, let me know. ***** While Maddie was off searching the walls of the room to use one her mom Lisa Ann, who lay blindfolded and tied to a bed like an X, Jason played with her pussy. Lisa wondered where Maddie was, when she felt Jason's larger hands massaging...

I Fisted Him, Now You Fist Me

by libidinal on Sep 13, 2017
Anal

Deb couldn't wait for her girlfriend Jessica to arrive at her place after work on Monday for a drink. She had a story for Jessica and was itching to tell it, knowing how Jessica would freak hearing all about what happened to Deb that weekend. "So what is it you're dyin' to tell me about, Deb?" Jessica asked, settling down with a beer. "Wait'll you hear, yo...

Danielle's First Time Ch. 02

by FellatiaViper on Sep 15, 2017
Transsexuals & Crossdressers

Danielle's Lust Chapter 1 After having experienced sex for the first time with a man as a woman in a threesome with Danielle's best friend Brad and his girlfriend Jessica, Danielle discovered that she really loves having sex with men more than women, but this confuses her greatly because Danielle is attracted to women, the aesthetics of a man doesn't do...

A Trip North

by Jaywesal on Aug 31, 2017
Group Sex

The following story is true and took place in approximately 1992. I've changed names and locations for obvious reasons. Readers should also be warned that this story contains sex between three men and one woman. If you are offended by acts between men and creampies then read no farther! +++++++++++++++++++++++ My wife and I were separated by ten years. At...

Look How Far We've Come

by MTL17 on Sep 13, 2017
Celebrities & Fan Fiction

I know we've had some small issues in the past @KaitlynWWE , but I'm so happy for you. Look how far we've come. #chickbusters4life Kaitlyn frowned and turned to the girl sitting next to her, who of course had that huge grin on her face which Kaitlyn struggled to stay mad at. Not that she didn't try her best, "You are so going to get me fired." It was now...

Vivian Laaning Ch. 24

by Bodington on Aug 14, 2018
Novels and Novellas

The next morning, Vivian awoke first. As soon as she was aware she had a woman in her arms, she became cognizant of the events of the previous night. She slid her bottom hand underneath Angela's arm pit to reach and maul Angela's ample tits. With her other hand Vivian fingered Angela's pussy. She concentrated on Angela's clitoris, which had the effect of awa...