Sissy Bet Stories

70,272 results
Orientation
Length
Source
Infinite Scroll

Three Days

by uncola man on Nov 28, 2002
BDSM

Setting: You're a Co-Ed belonging to a fraternity that made a bet with a fraternity from another school about the outcome of a football game between the two schools. If your team won, you'd get one of their girls for three days to do as you like with. If your team won, they'd get you for three days, from Friday noon until Monday noon. Your team lost. You jus...

Open in Reader

EroFights

by Winston on Oct 12, 2020
BDSM

You can't see anything. Blindfolded, you stay in your seat, stiff with apprehension and not a little fear as you feel the airplane make contact with the runway. Your 3-hour flight in total secrecy is finally over, but the excitement has only just begun. You've heard of this place in snatches of conversations before. EroFights - a place where every sexual whi...

Open in Reader

Complete Humiliation

by Mmeh on Dec 31, 2020
Fantasy

Anyone who Sammy passes will feel strong urges to humiliate him in a variety of ways regardless of their sexuality. Through Wedgies, pantsing, stripping, nudity or other sexual acts. Will he find a, way to break the curse? Sammy woke up on a warm Monday morning. He was already sweating from the crisp Australian heat. He went to his walkin bathroom, stripped...

Open in Reader

Her Enormous Son Ch. 02

by kimberlykitten on Sep 19, 2017
Group Sex

Cathy was smiling at her friend Cynthia with a goofy oh I just got fuck by a big black dick kind of smile while I just had an oh shit I just got caught fucking a while lady here comes the police kind of look. Cynthia didn’t really move. She just looked at the two of us. I guess she was in shock seeing me fucking her friend. I release my huge dick from betwe...

Mother in Law's Suitcase Ch. 03

by sethwaite on Sep 19, 2017
Fetish

Having cleaned myself up I went downstairs and put Ann's bra into the washing machine, set the program to wash and dry it and then retired to the front room. I poured myself a drink and sat down in front of the tv feeling a little guilty about what I had just done. "Shooting cum into your own mother in laws underwear, how depraved are you?" I thought to mys...

Secretary Morgan's Period Ch. 02

by headtyper on Sep 14, 2017
Fetish

Writer's note: I wrote the first chapter of Secretary Morgan's period at the beginning of the year sometime. I didn't realize they rejected it because of spelling and grammer mistakes. Sorry about that. Chapter 2 Secretary Morgan's Period It has been almost a month since Morgan and I discovered we had the hots for each other. Since then we spent much...

Any Given Fantasy Ch. 01

by Torres17 on Sep 26, 2017
Celebrities & Fan Fiction

AUTHOR'S NOTE: I have gotten permission from the author Hearsz who made a series called "Jerk-Off Sessions" to use his format and make my series "Any Given Fantasy", which there are many differences from Hearsz series and my series, such as going down different paths as you will see as the story goes on. I'm formerly known as "HornyTroy" as some of you may k...

Her Box Ch. 02

by mobyCock on Sep 14, 2017
Fetish

At this point, I knew Peter's balls must be quite heavy from many days of not ejaculating. I have been able to enjoy all of the anal sex I want, as regularly as I like and Peter has had no power to resist me, exactly as I had planned. I walk over to Peter, tied as always and put the box on his penis in order to make him hard. I am already fantasizing about...

Want to Watch the Game

by Ashson on Sep 16, 2017
Loving Wives

I'd caught a lift home from Mike and he suggested that I have dinner with him and watch the game. In case you're wondering, Mike and I live close to each other so we'd carpool to work. Saves us money and we're both going to the same place so why not? Anyway, not having any plans for the evening except to watch the game, I agreed. This way I got a free meal a...

Give Me What I Need...

by wetandwhat on Jan 15, 2019
Erotic Couplings

I flounced into the kitchen giving my hips just enough swish to flare out the pleats on my extremely short shirt. I tugged the tails of my button down shirt covering another inch of my mid rift, but exposing said amount more of my cleavage. He was there, still in work clothes. His mind probably still hung up on all those petty office things. I smirked as I...