Gay Shaving Sissy Stories

1,448 results
Orientation
Length
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Infinite Scroll

Becoming the Bear

by papawerebear on Sep 14, 2017
Gay Male

By PapaWereBear and UrsusMajr (What follows is a work of fiction. Enjoy the fantasy, but please do not confuse it with reality. None of the incidents portrayed happened, and none of the characters are meant to depict actual persons, living or dead. This story contains descriptions of sex between consenting adult males. If such offends you or is illegal fo...

Rest Stop Management Pt. 03

by rimaday on Dec 24, 2018
Gay Male

I awoke around 4:45 on my belly, my red panties a little twisted and crusted with dried cum. I could feel Big Daddy's deposit oozing down my taint and hardening in the panties. I could not believe, this was not some kind of twisted dream but my stretched leaking asshole took away all doubt. Twelve hours ago, I was kissing my beautiful wife and leaving for an...

Max's Chance

by robcub32 on Sep 26, 2017
Gay Male

(Note: This story features characters from "A Clean Start". You don't have to read that story first, but I recommended it.) "Hi, Max!" the familiar voice called out. As I walked out of the locker room, I looked and saw Pete's smiling face standing next to the weight rack. Pete was my best friend Tank's boyfriend or partner or whatever you want to call it....

Run and Hide Pt. 01

by CC_Ryder on Sep 25, 2017
Gay Male

I can see the headline: "Couple found strangled in paint aisle; home stager suspected." Ace Hoffman's shitty afternoon had bled into the evening, turning his mood sour and sharp. His last appointment of the day was supposed to be a simple design consultation, a first-time evaluation of the home with a list of suggestions. No heavy lifting, in and out in nin...

Pretty Boy

by tamgreen on Sep 25, 2017
Gay Male

I always hated stereotypes. At least, that was my excuse for resenting anyone who assumed I was gay. A guy can be fabulous and into clothes and still be attracted to the opposite sex. And I have been attracted to girls as far back as I can remember--that's no bullshit. Girls love a guy they can go shopping with. "Metrosexual" was what they called me, and I w...

Friend and Husband Seduction

by SluttyBisexualGuy on Mar 6, 2018
Gay Male

This is the first story that I have written in the first person narrative for Literotica. And that is because this is the first story that is absolutely true and without embellishment, as it comes directly out of my own sex life. Besides the names, nothing, and I do mean absolutely nothing else has been changed. I obtained permission from all parties inv...

A Gay Trilogy

by london_james2010 on Aug 30, 2017
Gay Male

Author's note. I have been struggling with my sexuality for some time. I have been experimenting. These three tales are about how I accept that I am gay Massage Seduction in Reverse I seduce the masseure! About a year ago, I was suffering greatly from a pinched nerve in my neck. I had been to a chiropractor a few times, but it just didn't seem to...

Tom and Luke Get a Family Pt. 01

by WittePiet on Aug 18, 2017
Gay Male

Tom and Luke get a family Pt 01 [This story follows on from Dom and Sandro] Chapter I The première of Oberon and a career opportunity A year had gone by uneventfully. Tom Appleton was now beginning his third year in his appointment as a lecturer in the University of Trabizona in Emilia-Romagna, and although he spent about 30% of his time in lecturing, the...

Pony Boy Ch. 05

by ChestersBoi on Sep 14, 2017
Gay Male

This is the fourth chapter of 'Pony Boy' and, if you haven't read the rest, then please do so first. Quite a bit of the story refers back to events in the earlier parts and it won't make much sense if you read them out of order. And, of course, there are the usual disclaimers; anyone involved in sexual acts is over eighteen and we're all fictional. Enjoy...

Fetish Galore

by sr71plt on Aug 18, 2017
Gay Male

I had been banished. My wife would be joining me in a couple of months, but I was sent ahead—banished from New York—for my transgressions. April's father had known I was bi before he bought me for her daughter—and he also knew how I made my living, because he had been paying April's bills. But I suppose he assumed I would put all of that behind me when we we...