Gay First Time With Older Stories

22,803 results
Orientation
Length
Source
Infinite Scroll

The Party

by davidshepherd on Aug 18, 2017
Gay Male

Man, married Bi-Curious seeks other similar men for daytime meetings. The paper had been in my bag for a couple of days now and I’d only just picked up the courage to phone the number advertised. It was a voicemail and the guy leaving the message sounded as nervous as I felt. He just left a number and his name, Pete. He asked that anyone calling should do...

4 Gangbanged by 40

by Scott_Heywood on Mar 2, 2020
Gay Male

Editor's note: this story contains scenes of incest or incest content. *** A friend had gotten ahold of me about 'a fetish shoot' someone had requested. She asked if I wanted to be 1 of 4 older guys strapped down and gang-fucked by a group of Young Guys. I hadn't done anything wild in a while, and I hadn't had a good ass pounding in almost a year. I agreed...

Sandy Liberates Me Ch. 2

by nowiamhere on Sep 14, 2017
Gay Male

I decided to call in sick the next day. I was exhausted from a night of love making with Sandy. My ass was also a little sore, so I did not fancy sitting down in an office all day. We had also talked for hours. We knew each others every intimate secret before long. Sandy had not had many lovers, and I was her first since she had a couple of operations to bec...

The Show

by Luckylucy1 on Aug 18, 2017
Gay Male

I am a 49 year old bi female. My husband is 51 and also bi. About 10 year ago we were watching an adult movie and it had the girl/girl scene when my husband asked if I ever thought of doing that. I admitted I had. Then he asked if I would do it if I had the chance. I told him yes. Then it was my turn, I asked if he ever thought of doing it with a guy. He tol...

Learning from Older Men Pt. 01

by letsplayhard1994 on Apr 1, 2020
Gay Male

This tale is a partially fictionalised account of my first time having webcam sex with an older man, an event which eventually led to my first time with a man. Names have been changed as well as locations but the following story is based off of real events. All characters are 18+. It was the spring of 2013, I had just turned 18 and I was extremely horny al...

The Joust

by Pelaam on Aug 18, 2017
Gay Male

The Knight pulled his destrier to a halt, the sounds of crying and pleas for clemency reaching his ears. He glanced back to the wagon that followed him. Ratafian was already leaping down, the thin, black-clad man reaching for the knives he wore at his belt before vanishing into the trees that lined the road. The Knight nodded, Ratafian would cut off the corn...

Catharsis

by HiRez on Aug 18, 2017
Gay Male

"I'm not a deadbeat." Asad said. Coach Henry Jacobs stood looking at the teenage boy, jaw clenched, his brawny arms folded across his chest. His green-hazel eyes were hard as slate giving him the forbidding appearance of a bald eagle. This had been arguing for some time now in his office, and Asad was going to be late for his AP Philosophy class. It was a...

The Watcher and the Woods

by Pelaam on Aug 18, 2017
Gay Male

Looking around, Jackson smiled at the thought of spending some time in the picturesque area. The autumnal colours a dazzling array of gold, ambers and reds. The crew of which he was a part were renovating a small hotel on the outskirts of a scenic, little town that relied heavily on tourist trade. The town had a nice variety of shops, not that he expected to...

A Dandy Boy's Awakening

by ThomasStevenson on May 7, 2019
Gay Male

Authored by Thomas Stevenson and Southern Suitor. ***** "Are those new shoes?" It was the man Tommy always noticed at the bus stop. The one who always had his tie in an immaculate double windsor, a gleaming fist of silk around his neck, sharp lapels and waistcoat, crisp French cuffs and cufflinks with gleaming patent leather shoes like angular black mirror...

Virginity for Sale

by KeithD on Jun 1, 2020
Gay Male

"OK, that enough for me for now," Gabe called out, tossing the frisbee one last time to the other Tulane student. Once free of the disk he loped over to the walkway in New Orleans' Audubon Park to the park bench, where he'd left his backpack, running shoes, and T-shirt. He'd been out on the park green in just shorts for the past half hour, tossing the plasti...