Lost Bet Pegging Stories

182,901 results
Orientation
Length
Source
Infinite Scroll

Clowning Around

by kevcol on Sep 17, 2017
BDSM

Part 1 It was a lousy place for a clown. She felt smug as she stood in Los Angeles' Union Station in her clown suit. It was complete with red nose, and big floppy, yellow shoes. Lauren felt a weird combination of anonymity and conspicuousness. She also felt somewhat empowered standing in the train station dressed as a clown. In the distance, she could see...

He is Your Master Now Pt. 06

by DomAlphamann on Oct 19, 2020
Transgender & Crossdressers

At the start of his first full day at the mansion, Ambrose decides to submit himself to whatever fate Cassilda ultimately plans for him, even though he is still daunted by whatever that fate might be. As a result, his stress is greatly reduced. Then, a new, unforeseen player arrives and contributes to his newfound mental well-being, even as she works to faci...

One Way To Spice Up A Marriage Pt. 03

by medic45 on Sep 16, 2017
BDSM

The Redskins had home field advantage for the first round of the playoffs. They were playing the Green bay Packers. The game was close going into half time but the Packers pulled away and won convincingly. The Redskins season was over and I had another CFNM party to attend. Jenn scheduled the party for the following Saturday night. After an early dinner she...

Black On Black Pegging Rules!

by Samuelx on Sep 11, 2017
Group Sex

Happily I slid my eight-inch strap-on dildo into Saul Jean-Pierre's tight asshole. The big and tall young Black man groaned as I penetrated him. Lying on his back completely naked on my big bed, he took it like a bitch. Bound legs hanging in the air and eyes filled with lust and shock. His hands are also bound for good effect. I wonder if he knew what he was...

Would You?

by Dragonologist on Mar 13, 2018
Toys & Masturbation

Would you? This question is being asked because, a week ago, we received a message on Facebook saying we should check our email for instructions because our lives were about to change. Normally, I simply dismiss random messages, like this, from an online person who I don't know, but the name that showed up was Mistress Trudy. It's the same name my wife use...

Bed and Breakfast Hotwife

by donaldelliott11 on Mar 9, 2020
Loving Wives

[Note: The hotwife in this story is, well, a wife, right? That means she has a husband. When she gets hot, he becomes a cuckold. You following this, Annony? Get over it, or read a different story. Oh, yeah, one more thing -- BTB is a fetish and has no place in Loving Wives.] *** Tracy and Don Elliott, empty-nesters in their late 40s, supplement their incom...

Olympic Bet Ch. 03

by legsfeettoes on Jul 9, 2019
Group Sex

First, I apologize for taking so long to finish this tale. Then I want to warn you that all participants are committing adultery and infidelity. The story contains BDSM, homosexuality, bisexuality, pegging, and group sex. If you find any of that offensive or unacceptable, please find another story to read. If you have not read the first two chapters (or hav...

Cigars and Whisky Turn into Wild Sex

by needsomerelief on Jul 9, 2019
Fetish

My lady and I have really grown in our pegging experience. She was new to it and I was minimally experienced, so we've gotten to explore more together. It's been a blast. We also have this tendency to see who can "outdo" the other with perversion. Last weekend, I think I won. We were out of town, and went for dinner, desert, drinks at the cigar bar. We get...

The Gentlemen's Panty Club Pt. 05 - Final

by joefelton on Aug 22, 2018
Fetish

Authors note: This is the fifth and final part of my story, and I believe I have saved the best for last. Thank you to those of you who've read the first four parts. For those readers who are new to The Gentlemen's Panty Club, I have included a short cheat sheet in this note, listing the major characters and a few significant details about them, that should...

Jason's Secrets Exposed Ch. 10

by jlenil on Sep 13, 2017
BDSM

I would appreciate if readers would rate and comment on this chapter. ***** Lillie and I had had a wonderful time, and I was enthusiastic about what a great pupil of perversion she had turned out to be. After Jason served us our breakfast, Lillie and I had our cigars on the patio and, afterward, she got ready to leave. She had a wicked glimmer in her eyes,...