Gay Sissy Whore Stories

3,205 results
Orientation
Length
Source
Infinite Scroll

Bikini Boi

by MySissyWorldx on Oct 3, 2018
Gay Male

My Brothers Troublesome friends... Note: everyone is of a legal age, and names have been changed for the sake of this story Enjoy *** My first time was more than a little bit terrifying, but enriching to my life beyond my wildest dreams. It began on a family holiday, just after my older brothers 21st birthday, him being 2 years older than I was at 19. Be...

A Natural 'Gurl'

by sexyR2 on Aug 18, 2017
Gay Male

Yes, I know that it has been a few years since I last posted. I was busy. I hope, however, that this new story makes up for the delay. It is in a new category for me, gay male instead of gay female like two of my previous submissions. Enjoy! Debbie, er, sexyR2... ***** Today... When the somewhat urgent knocking came to the door, Debbie knew in an inst...

Juera

by nancyvasquez on Aug 18, 2017
Gay Male

My name is Kevin Jean Bardot and, yes, I am a sissy. Most guys of my age had matured to where they had begun to look and act like men. I was small and skinny and had no body hair to speak of other than a few sparse, very blonde hairs on my pubis. I had sex with another person for the first time when I went into the navy and was stationed in a small city...

Owned:Fantasy Becomes Reality

by silkstockingslover on Sep 14, 2017
Gay Male

Note 1: This story was written and is dedicated to a true wannabe faggot-cuckold Dave. Note 2: A special thanks goes to Estragon for his copy editing work. 1. THE BEGINNING I blame Literotica. No seriously...if it wasn't for Literotica, none of this would have happened. Now in all fairness, some would argue it is my fault; as it was my own stupidity a...

Ozark Bitch

by oskarwild on Sep 14, 2017
Gay Male

Stranded Patrick let out a stream of obscenities as he kicked the tire of his rental car. The damn thing had stopped running in the midst of a rainstorm the likes of which Patrick had never seen before. It was a veritable deluge and Patrick was soaked to the bone as he tried to figure out why the car had just stopped running. He was on his way from Springf...

A Day In My Life

by keptsissy on Aug 18, 2017
Gay Male

I've been seeing my current boyfriend for almost two years. This is a very accurate day in my life with regard to that. **************** I love the way my hand opens and closes around him. My pink fingernail polish sets his cock off nicely. He's so big! 9 ½", I know because he let me measure it once, teased me about doing that after he made me measure my l...

From Alex to Lexi Ch. 02

by oskarwild on Sep 14, 2017
Gay Male

Lexi drifted back into wakefulness, opening his eyes slowly. At first he was disoriented, not remembering where he was or how he had come to be here. Then he became aware of the man lying next to him. He could feel his hairy chest and feel his stomach rise and fall against Lexi's back with each breath he took. He could feel the man's large hand resting on hi...

Transforming Tim

by oskarwild on Sep 25, 2017
Gay Male

The Elevator Rafe could hardly wait for his lunch hour to come. But he wasn't hungry for food. He was hungry for the new elevator boy. The new boy was just the type Rafe lusted after. He was short and slim; probably five-six and maybe a hundred twenty pounds at the most. And he was young. All of the elevator boys the building employed were high school seni...

The Exploits of Cockslut Kelly 05

by CSK on Aug 29, 2017
Gay Male

WARNING!! THIS IS A GAY MALE STORY, BUT IT IS ALSO AN EXTREME BDSM STORY AS WELL. THIS STORY COULD EASILY BE PLACED INTO ANY OF THE FOLLOWING CATEGORIES DUE TO THE CONTENT: GAY MALE, BDSM or FETISH. I HAVE REQUESTED THIS FOR THE GAY MALE SECTION, BUT IT MAY END UP IN THE BDSM SECTION OR ANY OF THE OTHERS IF THE EDITORS OF LITEROTICA DECIDE TO RE-CATEGO...

Punished Asian Shoplifter Ch. 12

by asianspankee on Sep 19, 2017
Gay Male

After my oral submission to you, I'm left quietly in the corner to reflect on everything that's happened so far till now. Mrs. Jones leaves satisfied, having "conquered" yet another sissy boy with her obscene weapon. After ten minutes you call me back to your side and announces that next week will be my final punishment session. I feel both relieved and sad...