Lost Bet Pegging Stories

182,901 results
Orientation
Length
Source
Infinite Scroll

The Bet

by tdallyn on Sep 12, 2017
Toys & Masturbation

Barbara and I had just finished a leisurely late breakfast when I lost the bet. I don't even remember what we had gambled over, but I do remember that I promised that if she won she would get anything she wanted. "I want you to masturbate for me," Barbara said. "That's not a 'thing', that's an action," I protested. "You didn't specify when you made the...

Be Careful with Your Cell Phone

by redwolf555 on Jun 19, 2019
Fetish

Steve was having a good day at the store that he managed. The store, a dollar discount store, was busy so time was moving along. A new employee had started last week and was doing very well. During a busy moment, Steve had set his cell phone down under the front counter to deal with a situation. Normally, Steve would never do that. There were things on the c...

Black Wife Cuckolding Black Hubby

by Samuelx on Sep 16, 2017
Interracial Love

What's up people? My name is Sheila Adeyemi-Williamson and I'm a Black woman of Nigerian descent living in the City of Ottawa, Ontario. I'm five-foot-nine, curvy and sexy, with dark brown skin, and short Black hair. I always look classy in tailored pantsuits when I go to work. And everybody notices. A beautiful, educated and confident Black woman is somethin...

Let the Games Begin! (JOI Idea)

by JMR85 on Mar 25, 2019
Toys & Masturbation

Alright, let's skip the long intro. Forget "setting the scene", forget about what I'm pretending to wear. I know you usually just fast-forward all that stuff anyway. You're mine, tonight. I'm going to give you your tasks, and you're going to follow my orders as close as possible. And, the tasks you achieve successfully are going to score you points. Points...

Tags.

by RicoLouis on Apr 19, 2017
Miscellaneous

As seen below their are many names for the large variety of sexual topics and no real agreed upon list of Tags so I am making a list as best I can to help readers find the stories that interest them. I will be using the most common named tags to make it easier for the readers to find what they like. Below we have an example. Name Stories Blowjob 34...

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Bollywood mixed wrestling

by maverick11111 on Oct 13, 2016
Fetish

This is your first mixed wrestling experience. You have waited a long time to wrestle women. And you find yourself an opportunity to wrestle bollywood babes.What's next? Kareena Kapoor Kriti Sanon Deepika Padukone Priyanka Chopra katrina kaif What's next? Kareena Kapoor Kriti Sanon Deepika Padukone Priyanka Chopra katrina kaif...

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Learning to Let Go

by NRMathis on May 15, 2019
BDSM

Jonah could not remember a time when he was more nervous. Per his habit, he showed up far too early at the Cheesecake Factory, and was waiting at a table. For her. For the woman he had been chatting with online and exposing some of his deepest, most embarrassing fantasies to. The woman who wanted to meet him in person. The Domme who he wanted so badly....

AC: lost in the animus

by Damos on May 17, 2019
Fantasy

“David; nice of you to come!” a voice spoke and looking over there I saw the dark haired woman standing there greeting me, “This is the team, Lucy!” I looked over and seeing the blonde nervous woman she whispered, “Hi!” I looked over to Rebecca who whispered, “She fancied a man who died saving the world!” I nodded before saying, “Desmond!” she nodded before...

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After Party Truth or Dare

by 4EyesDawn on Sep 17, 2014
Group Sex

You and your friends just spent the last couple hours at a party that turned out to be pretty lame. It's a Friday night and you've all had a couple drinks and want to have a good time so you all head back to the house several of you share to keep the party going.What's next? Male Female What's next? Male Female...

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A Shemale Shock: A MILF Falls

by silkstockingslover on Sep 25, 2017
Illustrated

Summary: Mom catches her daughter with a teenage shemale and.... Note 1: This is a Nude Day 2017 Contest Story so please vote. Note 2: Thanks to Tex Beethoven, Robert, and David for editing this story. I was having a bad day. I'd spilt coffee on myself on the drive to work. I'd gotten a rip in my nylons. And I'd forgotten my notes for tonight's intervi...