Lost Bet Gay Stories

190,163 results
Orientation
Length
Source
Infinite Scroll

Darlene Lost The Bet

by Diabloirishman on Sep 17, 2017
Loving Wives

My wife of thirty plus years and I started playing some card games that led to more tantalizing games to a game of poker that has continued for years with some amazing stakes. Some years back it all started out tame enough but over the years our stakes have become real kinky. We both really love the excitement and this has added a new dimension to our lives...

Mixed Pairs

by 4glory6 on Sep 17, 2017
Loving Wives

[Webster's definition of April fool: The butt of a joke or trick played on April Fools' Day. also: such a joke or trick] Boston, Massachusetts, 1 April, 2016, Faneuil Hall Marketplace "Is Victor still pouting at his room over at the Millennium Hotel?" Serge Agapov slouched back in his chair at J. J. Donovan's Tavern in Boston's Faneuil Hall Marketplace an...

I Put on A Cock

by ndeavour on Jan 6, 2020
Erotic Couplings

Hi, my name's Liz. I'm not about to tell you how old I am -- but I have a 25 year old son, so that should give you a sense. I've only just stopped coloring my hair and begun letting a whole lot of silver to emerge. I no longer have the slim figure I did before having my son; I gained nicely in the boob department, but picked up some extra padding all over. I...

Never Lose a Bet with your Wife

by Everyday2 on Sep 15, 2017
Fetish

I had been married to my wife for 9 years when a life changing event happened. Julie, my wife, is a very attractive 28 year old woman. She is 5'5" tall and is in very good shape. She has a beautiful ass and likes to show it off in tight jeans and short skirts. My name is Tom, and I'm just a bit taller than her and also in very good shape. She tells me that I...

American Hustle: Swing It

by Zev95 on Sep 17, 2017
Celebrities & Fan Fiction

I love my wife. That is, of course, I love Sydney. Sydney's wonderful, she's amazing, you know Sydney. But Rosalyn, my ex-wife—okay, I love her too. What can I say, the heart's not one of those computer-machines that just boops and beeps. It sings, it makes its own music, and I never quite could stop seeing all the great things about Rosalyn I fell in love w...

How We Became An "Owned Couple" Ch. 08

by watchdwag on Sep 11, 2017
Loving Wives

It was evident that Connie was much more interested in Laura than me but I still enjoyed the sessions where she invited me to play with along in their little love games. Laura and I had only had sex one time since she had allowed Connie to seduce her and begin exploring this new lesbian lifestyle. Though that was the case, I was still confident my girlfriend...

A Weekend in a Cabin Ch. 03

by tascalun on Sep 17, 2017
BDSM

Angel looked at the sleeping man tied spread eagle on the futon and thought about how she had gotten him there. Every weekend she got together with a few friends and played poker. Becky used to pick on Angel saying she needed a sex slave. So when Casper had agreed to play strip poker Angel decided she would follow Becky's advice and see what it would be like...

Paula

by Marlene on Sep 13, 2017
Transsexuals & Crossdressers

Hi----I got the idea for this story from a Literotica fan. I’ve never done anything like it but it’d sure be fun wouldn’t it? A few months ago I met a woman while getting coffee at one of our local “gourmet” houses. We were in line and started talking about whatever (I was in my male persona). Her name is Paula and she’s 42 but looks an easy mid 30's, Very...

An Alien Love Bk. 02 Ch. 03 Again

by Read_Moore on Jul 15, 2020
NonHuman

Horray! I am done with my work on Holiday Cup Of Joe (That is my next Ice Era Chronicle.) So you know what that means??? I can play with this again. Writing about these alien takes me back to a time when I didn't have so much to worry about. I know. That's odd. Anyway, if you are still here reading, thanks! Cheers, ~M. from C.M. Moore *** *Chapter 3*...

Hell Has No Fury Like A Drag Queen'

by Victor C. Anderson on Sep 16, 2017
Transsexuals & Crossdressers

The Morning After: Scott slowly awoke to his cock being stroked. Relishing the smooth skin pressed to his back, the silky leg thrown over his, and the lips nibbling at the nape of his neck, he was surprised that his wife was this amorous in the morning. Susan was no prude, but she also was not the sexual aggressor in their marriage. Indeed, their first sexu...