Gay Lost Bet Pegging Stories

11,553 results
Orientation
Length
Source
Infinite Scroll

Personal Coaching Ch. 03

by BeltBuckle on Apr 17, 2019
Gay Male

It was a quiet night and the neighborhood was mostly quiet. Since it was monday, most people have gone to sleep early and most of the window were dark. A single, solitary floor in one older building was still lit though. If someone climbed onto the ledge and looked through that window, he would see a gigantic, beautiful man named Oscar, stark naked, sittin...

Grandpa's Summer Visit

by timmywells on Apr 3, 2019
Gay Male

I knew that my grandfather was going to visit us, so I wasn't shocked when I saw him that Thursday afternoon in the guest room. It was the way I saw him that set me back a bit. I walked down the hall that afternoon, and when I passed the bathroom I could tell that someone had gotten out of the shower recently. That someone was my grandfather, and while it w...

How I Became an African Man's Wife

by Secret_sex99 on Mar 2, 2020
Gay Male

I was straight my whole life. I was married to a beautiful woman for 8 years. We had 2 sons. We were divorced for about 2 years. I was never really athletic. I've always been chubby and more into reading books and eating food than sports. It got worse later on in my marriage as I was now in my early 40's and my metabolism has slowed down significantly. M...

The Unexpected Meeting

by CoburnAisling on Feb 4, 2020
Gay Male

Adam leaned back in his chair, the leather creaking as his weight shifted. Motes danced in the light streaming through the floor-to-ceiling window behind him; the same light shone through his dark blonde hair, leaving him just slightly warmer than was really comfortable, but not warm enough to overcome the sucking lethargy that kept him from getting up to di...

Kidnapped Ch. 01

by AgirlcalledBob on Jun 19, 2019
Gay Male

Chapter One Ollie Slater slams his long body between Mikey and I on the ratty sofa with an 'oomph' of exhaled air. "I'm screwed!" His face is twisted in dismay as he plucks the joint from Mikey's elegant fingers before sucking in a heavy drag. The motion highlights the strong bones of his face, his deep-set brown eyes narrowing as the smoke rises. I'm a...

Cairo Surrender Ch. 01

by KeithD on Jun 12, 2019
Gay Male

Note: All characters in this novella are older than 18. [This is a completed ten-chapter novella, to be posted in six entries by mid June 2019] ***** Shepheard's Hotel Gentlemen's Dining Room, Cairo, Egypt, November 1924 The times were such that it was folly for anyone of European visage to walk the avenues and alleys of Cairo alone. It had been four yea...

Drag Queen and the Indecisive Guy

by jim_janes on Jan 16, 2019
Gay Male

Walking down the steps my mind was at war with itself. My two personalities were screaming at each other. I have always had debates in my head. I envy those who know what they want or know what must be done without hesitation. I was never that lucky. Every decision was a WWE match between my ears. Indecision was my middle name. Mostly the internal argument w...

A Bend in the Road

by Writer_FM on Aug 22, 2018
Gay Male

My divorce was final and I was beginning to understand what it really cost me. It wasn't the attorney's bill, the lost equity in the house, or the lump sum I paid to avoid monthly alimony. I'd recover from all of that. No, the real cost was the realization that my sex life was probably over. I'm 45 and I'm no Chris Hemsworth. Not even an aging Chris Hemswort...

Box Shaped Heart Ch. 24

by laurasfox on Feb 26, 2019
Gay Male

Chapter Twenty-Four -- Not Good at Feeling Was he really ready for a visit? Aron wasn't a stranger, but that didn't mean he should receive him wearing pajamas. There was too much mess lying around, too. Mumbling to himself, he began tidying up the small living room, which now, after staying at Aron's house for a while, seemed unqualified for the 'living' pa...

A Cruising Life Ch. 06

by tommydntx on Jul 13, 2020
Gay Male

Thanks again for reading my stories and providing feedback. As you can guess from the tag line, this one will involve members of both sexes. But, before that, it will also involve a couple of other firsts. These three events are the most memorable from my times at a place I've yet to mention. So far in these stories, I've talked about places around Louisv...