Anal Bets Stories

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Bad Bets

by justsomeguy41 on Mar 11, 2019
Anal

Note: So as per usual, this story is heavily centered around anal with some light free use elements though NO ACTUAL SEX SCENES HAPPEN since I was more interested in dialogue, attitudes and the scenario. If that doesn't do it for you just skip this one. Also, I doubt I'll ever do a story from the girl's perspective again. ***** Opening the door, I was gr...

No Game No Anal

by DefeatedDamsels on Apr 22, 2025

All ****, war, and robbery are forbidden in this world. All conflict in this world will be resolved through games. In games, each player will bet something that they agree is of equal value. As long as it doesn't violate pledge three, anything may be bet, and any game may be played. The challenged party has the right to decide the rules of the game. Any bets...

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Sucker Bet

by The_Technician on Sep 14, 2017
BDSM

= = = = = = = = = = = = = = = = = = = = "One of these days in your travels, a guy is going to come to you and show you a nice, brand new deck of cards on which the seal has not yet been broken. This man is going to offer to bet you that he can make the jack of spades jump out of that deck and piss in your ear. Now son, you do not take this bet, for as sure...

Heather is Hot at Our 25th Reunion Ch. 03

by rafters11 on Sep 17, 2017
Mature

Saturday I awoke to Heathers soft voice saying breakfast is almost ready, followed by a passionate kiss. What a great way to wake up. I went to the bathroom then joined Heather at the table for breakfast. She had fixed pancakes, sausage and coffee for breakfast. We planned things to do for Saturday and Sunday while we ate. We decided that we would spend the...

Betting Your Ass

by OneSilky on Sep 14, 2017
Anal

A Silky Adventure This is a stand alone story, but makes more sense if you start with Adventures of Silky #1 * My name is Silky, I'm almost 21, and I live with my owner/lover/Daddy George and my sister/lover Jessica in Alabama. We all sleep together in one big bed, and life is generally sweet. We are college students. Jess is tall and blonde with blue eye...

Senior Week Day 01

by Good Burger on Sep 14, 2017
Fetish

Amanda was so excited. She had just graduated from high school, and was spending her first week of freedom with her boyfriend, Eric. They had rented a cabin in the mountains for a week and they had it all to themselves. Amanda and Eric had been together since Sophomore year. Recently, it felt like they had just been going through the motions, and this week w...

The Poker Game Ch. 01

by kellycummings on Sep 26, 2017
Group Sex

My husband and I had been swinging a little here and there over the last couple of years. It wasn’t the usual swapping or any of that, mostly me with other men while he watched and masturbated. He didn’t have any desire to be with another woman and I certainly didn’t want to see him with one so we kept our fun restricted to single men and the occasional coup...

Nancy's Mid-life Awakening Ch. 17

by Saltysooner on May 7, 2019
Romance

Chapter 17 Weekend Retreat Nancy remained excited from Dana and Steve's party for several days and found herself trying to think of how she might host a "Game Night" of her own for the other couples they knew. When she saw Jeanne and Craig at their club's regular run the following Saturday, she sensed a change in their dynamic with her. With their runnin...

Angel Wrestling League Ch. 04

by Stipend on Oct 6, 2020
BDSM

Hey guys, sorry for the delay in chapters. I've known since I started this venture how I wanted the story to play out exactly. The timetable is to have all 20+ chapters done by the end of the year, but that may be a little ambitious. I appreciate all the support, though, and if you have any questions about anything feel free to ask them in the comments below...

Vegas and Unrequited Love Ch. 05

by spoilmwhole on Sep 15, 2017
BDSM

End The bartender goes back to his duties and the four of us get comfortable on the couch. We're entwined naked together admiring the naked action around the room. The lights come up part way. "Ladies, Five minutes until speed 'dating'," Ms. Jess announces as she's throwing pillows around the outside of the oversize coffee table. Senegal takes me by the han...