Sissy Bet Stories

70,272 results
Orientation
Length
Source
Infinite Scroll

More Than OK

by NaughtyAngel75 on Sep 12, 2017
BDSM

This story not to be reproduced for profit. Comments welcome. She watched the clock, waiting for his arrival home. He'd told her that morning that he had something special planned for this evening but wouldn't divulge any more than that. All day she'd wondered what he'd meant but it could be anything and all she could do was wait impatiently. Finally, she...

Confessions

by SciGuy on Sep 14, 2017
Humor & Satire

Thanks, Doctor. No, I had breakfast earlier. Can I have the sofa, today? Great. Let me get right to the meat of it, Doc. I had this strange dream a few months back. I dreamed I was a WOMAN! I AM calm. Sorry. Sorry-about-that. Well, I’ve had sex dreams before, I guess, but this was different. You know me, Doc. I coach ball, I’m a married man. A father. Wh...

His First Piece of Ass

by kandie on Sep 3, 2017
First Time

LeeAnn's pussy was on fire, she yearned to feel a hard cock sliding into it, but she couldn't take her eyes off of what she was watching. She must touch herself...it felts so good, inflamed by her lust from what she saw. It was her lover, Ray, sucking the cock of the man they just picked up at the local pub. Oh fuck, was the man hard! It was Friday night, a...

Fallout 3 - Talon Company Ch. 03

by Mackenzie Taylor on Sep 13, 2017
Sci-Fi & Fantasy

Hey everyone, this one is a bit short but the next one will be longer and much hotter! Votes and Comments are welcome, I thrive on the encouragement. Mac *** Mur woke up in complete darkness. She was on her back, Conn on one side of her and Wyatt on the other. Conn was holding her hands above her head and lazily running his free hand over her stomach maki...

Playing With The Playmate

by Dice_Casden on Sep 13, 2017
Celebrities & Fan Fiction

This story is written by both Dice Casden and Kristi as part of the D&K Universe. This and all of the other stories we write are for entertainment purposes only. If you do not like what we choose to write about, Literotica offers many other stories for you to read instead. ****** Hours before the start of the Taboo Tuesday 2004 Pay-per-view spectacular, E...

You Got The Moves

by Dice_Casden on Sep 17, 2017
Celebrities & Fan Fiction

This story is written by both Dice Casden and Kristi as part of the D&K Universe ****** In the backstage area of the Mohegan Sun Arena in Uncasville, Connecticut, the dancing and wrestling sensation known as DJ Gabriel is walking from the catering area after getting a small bite to eat. Gabriel is wearing jeans and his favorite black leather jacket, and he...

Is The Past Prologue?

by Tonyjoe on Sep 17, 2017
Non-Erotic

We were having our traditional after Saturday golf beer, talking about the one that got away – wait, that's a different sport – and other things, when Jerry took advantage of an opening and started telling me about his marriage. He ended his rant with a complaint about his wife: "I'm an affectionate guy, and she just isn't responsive." "I don't know of a ma...

Party Animal

by TJA on Aug 19, 2017
Exhibitionist & Voyeur

Feedback is welcome. * My name is Tony and I have a small outside catering business in Brighton. The business was hard work and I was struggling to keep it going. Until recently that is. I am 26, six ft tall, well built (thanks to my swimming, I am in the local team) and have been told that I am more than adequately endowed by my past lovers. One Friday...

Superbowl Party 2014 in Ottawa

by Samuelx on Sep 16, 2017
Transsexuals & Crossdressers

Sitting in my friend's living room in the west end of Ottawa, Ontario, I looked at Rhianna Brandon and smirked. If the Broncos lose to the Seattle Seahawks, her fine-looking, simply enormous chocolate ass is mine to do with as I see fit, that's the bet we had. I watched Russell Wilson and Richard Sherman massacre Peyton Manning and the Broncos and smiled con...

The Special Customer

by AngelaK on Sep 14, 2017
Transsexuals & Crossdressers

I'd been working at Jackie's long enough to realize her boutique offered more than high-end clothing. She also offered high-end girls for occasional outside 'services'. We never accepted money from a customer, or "client": Jackie handled all transactions. She paid all of us very nice salaries, more than enough to live on, and more than enough to be able to b...