Sissy Bet Stories

70,272 results
Orientation
Length
Source
Infinite Scroll

Dare Girl Goes Astray Ch. 02

by niteowl2003 on Sep 17, 2017
BDSM

Chapter 2 'The Coin Tosses' Mistress Mandy, It is now Monday morning and I have received the full report of Cindy's dare which took place on Friday night. I have cause to speak to you in connection with our mutual sub Cindy, as you are fully aware I issued a dare to Cindy, for last Friday night, which it seems you chose to hi jack. Whilst I am not in the...

A Night in the Playroom

by MarmotSteelsBabyGirl on Sep 17, 2017
BDSM

We meet at the designated time, 10 pm, in the hallway leading to our "playroom". "Oh daddy, you look so handsome", I gush upon seeing you. "You have chosen the perfect outfit for this evening." Grey cutaway tailcoat, ivory waistcoat, cravat, black pinstriped trousers. "And you my pretty pet, look ravishing. What do you call this look? Steampunk Saloon girl...

Britney Ch. 23: Out House

by SZENSEI on Sep 13, 2017
Exhibitionist & Voyeur

The barn door was wide open. Keith Foxx did his best to keep busy on the finishing touches on the Ruuthouse Farm. The barn he had helped erect was pretty much done. Paint and smaller fixtures were about it. He still stuck around to see what else he might learn. After Isaiah Ruuthouse's admission of wanting to experience sex with other women caught him off...

The Game

by charlotsky on Sep 16, 2017
BDSM

'Am I awake, or am I sleeping. I can't move... And, where am I?' I became suddenly aware that I was finally awake, but what happened? I find myself naked, gagged and blindfolded. I am strapped facing a device of some sort, in the form of a large 'X' leaning slightly forward; my hands spread and strapped above my head, and my legs spread and strapped. There...

Pleasing Misstress

by humblebumble38 on Sep 17, 2017
BDSM

I'm all a flutter. Tonight i get to spend time with Her. Its been a while since She allowed me to come into Her dungeon. I think back and rub my bottom remembering O/our last session. I knock softly and wait on bended knees. "Enter" i hear from within. I open the door and crawled in. She is standing just a few feet inside. All i see are Her shiny black bo...

Still Sex at 70

by ainu on Sep 17, 2017
Mature

I'm a 72 year old male in fairly good condition, all things considered. I do my sit-up exercises including push-ups and walk regularly. My regular route is a little over two miles. So I'm in better shape than many my age. However, I enjoy food and a friendly drink so I'm a little soft with too much around my middle. I've shrunk a little with age, used to be...

The Dream Job

by ThickFilling on Sep 12, 2017
Erotic Couplings

* * * ...those damned Yankees! Couldn't seem to live up to their reputation the one year I choose to bet on them! He figured they were a safe bet, literally, but no, oh no, no, no, no— "Yes! Yes, yes, yes, oooooooohhhh yes! YES!!! George snapped back to the task at hand, taking a moment to orient himself. It's a trick of the trade he learned long ago, men...

Trophies

by Untameable_Guy on Sep 14, 2017
Erotic Couplings

I pick up the pillow and throw it back on the couch and found another trophy. It is her black lace thong panties. I kneel down and pick them up and bring them up to my nose. I inhale deeply and can still smell her there. Damn did Heather look hot in those, although she was not in them for very long last night. I twist them around my fingers remembering how w...

Collecting On Our Bet

by EatU4Hours on Sep 12, 2017
BDSM

I hear you fumbling with your key at the door and get up to open it for you. You look up at me with that shy but playful smile on your face that always gets my heart beating a bit faster. I know you have been looking forward to this as much as I have and I am sure you hurried home from work, anxious to see how things will go. After a little kiss hello I loo...

Jon's Punishment

by JonMHoll92 on Sep 14, 2017
Erotic Couplings

Sometimes your life is going so perfectly, you're convinced that nothing could disrupt the success and happiness you enjoy every day. And then out of the blue, you realize that something you did has upset the most important person in your world, and they're not getting over it very easily. Such was the case for me just recently. I thought that my Caribbean g...