Gay Age Difference Stories

7,185 results
Orientation
Length
Source
Infinite Scroll

Mom's Not Home

by timmywells on Aug 31, 2017
Gay Male

Henry Clarke stood at the fence and over at the cute boy who was reclining in the lawn chair, as naked as the day he was born and oblivious to the presence of his mother's new boyfriend. The middle-aged man took a deep breath as he enjoyed the innocent form of Todd Hastings, who at 18 was about the third the age of the voyeur, but while the lad had a boyish...

My First Bi- Black Cock Experience

by JJgreenville on Aug 30, 2017
Gay Male

I had always wondered what it would be like to have another man give me a blow job. Never in my wildest imaginings did I ever think it would actually happen, especially at my age. I'm a white male, pushing 82 years of age now. I'm single. Well, actually I'm a widower, having lost my wife of nearly 60 years, fours ago. We'd been quite happy during all that t...

If Motel Rooms Could Talk

by timmywells on Aug 18, 2017
Gay Male

The dingy and dated decor of The Skylane Motel on Central Avenue just outside the state's capital city hadn't been updated since Gerald Ford was President, but most of the people who stayed there didn't care. That was the case on the night of May 25th, when a nondescript 53 year old married man named Melvin Stark paid the $33.50 to rent room 108. The man ha...

It Was The Summer Of '85

by Messier82 on Sep 14, 2017
Gay Male

The following is a tale of actual events which occurred 30 years ago. I hope that the factual nature of my story is adequate compensation for any elements of the tale which may be absent or unsatisfactory. Whilst these events are among the most vivid and memorable of my life, the passage of time inevitably alters the reliability of our recall, especially whe...

Hard Start

by KeithD on Mar 17, 2020
Gay Male

(gay prostitution, age difference, gay interracial, tough times, street rent-boys, car sex, fake cops, gay anal, rough gay sex, historical) [There is no under-18 sex activity in this story.] Jimmy grimaced and let out a gasp as the cock bulb breached his sphincter and the rest of the cock followed it up into his channel. He looked over at the wad of bills—...

A Life Well-Loved

by bhart1 on Aug 18, 2017
Gay Male

Sunday morning, June 9, 1996...it was our first anniversary and just over a couple of weeks shy of my forty second birthday. My eyes fluttered open to see 9:47 displayed on the digital clock by our bed. I felt Chik's warm mouth gently nursing on the head of my morning hard-on and I looked down over the crest of my belly to see his head barely bobbing under t...

Falling for Matthew Ch. 04

by icyblue on Sep 14, 2017
Gay Male

"Are you dating Steven behind my back?" Oops. I'd planned to ease into it slightly more elegantly than that. Jane's jaw dropped in surprise; clearly she wasn't used to being accused of dating her step-brother first thing in the morning as she answered the door. "Do you wanna come in and maybe keep your voice the fuck down?" she hissed. I followed her to...

A French Reunion

by QuentinX on Aug 18, 2017
Gay Male

It was when I entered the next room of the art gallery that I saw him. His hair was only slightly sandy, retaining much of the blonde that he had when he was younger. It was still tied up at the back of his head, a sign of most older men that they were trying, but failing, to retain their youth. On him, it didn't matter. He may have been a pound or two heavi...

Kevin Has a Gay Old Time

by prostation on Sep 16, 2017
Gay Male

"Kevin!" Kevin's mom yelled at the top of her lungs. "What???" Kevin yelled back. Kevin was 20 years old, just out of high school, and very lazy. And moreover so, it was a warm, hot, sunny day, and like all young energetic young men, he had decided to take the whole summer off, just lazing around, doing nothing, nothing at all. Now, of course, he would h...

The Cycle Ride

by ScotishGuy on Sep 16, 2017
Gay Male

Saturday morning saw me at Dundee railway station, walking my bicycle towards the large group of cyclists which had gathered beside the Tay road bridge. This was the weekend charity cycle from Dundee to Pitlochry and back, to raise funds for testicular cancer research. There were dozens of cyclist gathered, waiting for the cycle to start. This was going to...