Gay Lost Bet Pegging Stories

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Turned into a Sissy

by drogon01 on Sep 14, 2017
Gay Male

I was 20 years old and had been going out with my girlfriend for about 9 months. Everyone thought I was straight, and although I had never really acted on it, I had often had gay thoughts and wanked over other men. So when my girlfriend told me that she wanted to fuck my arse with a strap on, I was interested. I was at university at the time but was home...

Pegging Peter Ch. 09

by KenJames on May 15, 2019
Gay Male

Author's Notes: "Pegging Peter" is a BISEXUAL series. It has male-female sex, as well as male-male sex. "Pegging Peter's Women" is a companion series to "Pegging Peter" and takes place on the same weekend as "Pegging Peter" Chapters 6 and 7. In response to the (quite justified) complaints about the confusing number of characters in Chapter 8, I'm providin...

Colorado Rocky Mountain Bi Ch. 04

by walterio on Apr 22, 2019
Gay Male

A QUICK VISIT Sandy and Gordy were seated in my great room with a beer after we unloaded Gordy's car. He would be staying with me until he found a place of his own. Sandy had a flight at noon on Sunday back to Denver. They then shocked me when they shared a new sexual experience. "So, what have my favorite twins been up to?" "Sandy started pegging me." "...

Kinky Tales: Many Cocks to Suck

by silkstockingslover on Jun 19, 2018
Gay Male

Summary: Straight guy finds a theatre where anything gay goes. Note 1: This is part 5 of a potentially lengthy series about a couple exploring many aspects of their once-hidden sexuality. Part 1 was told in two separate versions: To read the wife's version read: Kinky Tales: I Pegged my Husband In this story Dani accidentally learns that her husband has...

Exploring Sexuality: Cock Sucking

by silkstockingslover on Sep 19, 2017
Gay Male

Summary: Straight guy sucks three strangers' cocks for sister-in-law. Thanks to: Tex Beethoven, Robert, goamz86, Dave and Wayne for editing this story. Although this story can likely be read on its own, reading the first part will probably be useful. But in case it helps, here is a summary of Exploring Sexuality: A Pegging: Ben gets intrigued by the idea...

Always, Forever and a Day Ch. 02

by Baby789 on Sep 14, 2017
Gay Male

If you haven't read The Day It All Changed and Always Forever and a Day please read them first. Thank you feedback appreciated. * Tyler groaned and sighed, stretching as he woke up, he stomach cramped and he was soaked with his own sweat. "How are you, Tiger?" Matt murmured next to his ear. Tyler had came down with a bad case of the flu and Matt had been...

Master Comes on Sunday

by Cap_N_PieSissy on Dec 9, 2019
Gay Male

My Master is much younger than I am, and it would be entirely accurate to describe him as a twink. Small, lithe without an ounce of body fat in him apart from a certain softness of his facial features, and packaged in soft, smooth hairless skin. He fully enjoys all the greatest blessings of youth, but there is a devil in him. He found me on the internet. I...

He Gives It To Him Straight

by kai425 on Jul 31, 2018
Gay Male

Editor's note: this story contains scenes of non-consentual or reluctant sex. * I hear a bang of the front door slamming shut and loud footsteps heading my direction. It must be Matt about my recent Facebook post of coming out. All the responses have been extremely positive and supportive and I find myself grinning from one to ear to another. I turn to loo...

The Halfway Inn pt. 02

by Robert_Furlong on Aug 18, 2017
Gay Male

I got on the bed first, kneeling down on the mattress and splaying my legs wide open. Seeing me like that, facing him expectantly with my cock arching upwards, made Pete laugh again. "Bloody hell, mate," he informed me, "you've got the biggest dick I've ever seen – not that I've seen that many, mind!" I beckoned him to get on the bed with me, and, as he po...

He-wolf Ch. 06

by lonleylucas on Sep 14, 2017
Gay Male

Disclaimer: All characters involved in sexual relationships are over 18 years of age, and no minors are sexually exploited in this content. In no way are actual events or persons depicted. This is my own fictional story and my characters mine and my own if you want to get to know me add me on skype always happy to have more friends allen9980) Alex-18 werewo...