Lost Bet Gay Stories

190,163 results
Orientation
Length
Source
Infinite Scroll

Pump and Grind

by Archer2050 on Sep 12, 2017
Mature

Tanya had picked Bob up at the airport as a favor for Marie, her girlfriend—also known as Bob's daughter. Tanya knew that Marie's lesbian lifestyle was a secret to Bob, and she felt okay about that. The only reason Bob didn't know was because he lived in California, and they lived in Vegas, and he'd only come for short trips. The women were openly gay in the...

My Lust for a College Stud Ch. 01

by kauen on Sep 19, 2017
Erotic Couplings

(Authors Note. First things first this is my first story so go easy on me. Second this is hopefully the first part of a short series. I didn't want to write a rushed story instead I prefer one with atmosphere and some depth and a lot of build-up but likewise I didn't want a huge story so instead decided to split it into parts. Not much happens in this first...

Married Guy New Experience Ch. 03

by Marriedandneedingmore on Sep 19, 2017
BDSM

This is the third part of my first story, I hope you have read the first two to understand how I have got to where I am now. As usual I welcome any comments or suggestions. Still unsure what is the right category!! * Two weeks ago I was a normal married 50's guy, married 25 years with a non-existent home sex life. All work and no play! I have to travel...

Bi Exhibitionism

by jwc10010 on Sep 12, 2017
Group Sex

It started as a joke really. We were roommates and had been hanging out having a few drinks at a late night spot in town. Paul, myself and Adrianne. It was late and we were well into it. Anyway, a friend of Adrianne's at work was getting married and she wanted to have a bachelorette party for her at the apartment. She wanted to have something fun and wanted...

Kerri's Descent Ch. 02

by Honey_Bee_16 on Sep 12, 2017
First Time

Time really flies during your first semester at college. It had been several weeks since I had given head to Matt, a guy I met at a party. It was the furthest I’d gone with a guy, and I still couldn’t really believe it had even happened. I had thought about it several times when I touched myself at night, and sometimes my pussy would get wet during class jus...

Have Some Ribs & My Wife

by Tattletale on Sep 18, 2017
Loving Wives

An innocent backyard barbecue with friends led to the most exciting sexual experience of my life. My wife Laura and I were treating our best friends Jerry and Kim to a barbecue and a refreshing dip in our pool. The four of us had met at the company that we all work for. We had so much in common that it was inevitable that we would become best friends. We wen...

The Lock Ch. 07: GATHER

by theMasterBaiter on Mar 11, 2019
BDSM

TRIGGER WARNINGS: Simulated Rape, Pain (1 drop blood), Male Bi/Gay, MaleDom, FemDom, Family (no incest), Consensual Non-Consent, and Sex Work (idealized) The only coercion is from a sense of duty to family. All over 18. Credits: Edited by the 'Erotic Confectioners. Many thanks to Onyx03, Grrl Orc, Jasmine27, and allnitediner as well as others for editing th...

Out of Nowhere, a Gay Encounter

by NC_Coastal on Aug 21, 2018
First Time

I still can't believe this has happened. I'm 48, a former athlete who played a little baseball and ended up in sports marketing with a major firm in New York. The city's not for me, and I'm glad I get to travel all over for my job, I'm divorced, a father of two girls and have enjoyed a healthy sex life since I was a teenager. And never once did I consider...

Magic Dress - Felicity Pt. 03

by SlightlyRude on Apr 9, 2019
Transgender & Crossdressers

CHAPTER 5 We did some limited practice going out as Felicity. One time we went to a multi-storey car park after the adjacent shopping centre had closed and went to higher floor where there were very few people. I walked around in high heels backwards and forwards to the payment machine at the other end of where we had parked. One car came down from a higher...

Movie Booth Bang

by Fantasycd on Sep 16, 2017
Transsexuals & Crossdressers

I'd done lots of internet chatting before and heard about adult theaters and what went on in the private booths. And after years of cross-dressing, sliding on silky panties and bras and fantasizing about taking a cock, I decided it was time to go for it. Of course my true fantasy was to be dolled up and treated like a girl for hours, pampered and fucked. But...