Gay First Time With Older Stories

22,803 results
Orientation
Length
Source
Infinite Scroll

A Dandy Professor and a Dapper Boy

by ThomasStevenson on Jul 17, 2019
Gay Male

Something about the sheer dress socks made Charles nervous. He was at his bed, fully dressed in his best three-piece suit, lush paisley tie knotted around his crisp cutaway collar, grosgrain braces to match, silk handkerchief spilling out of his breast pocket, glittering cufflinks--the whole nine yards. But he saved the sheer socks for last. It was the way...

Frustrated

by LittleTommyTudor on Sep 14, 2017
Gay Male

I was very frustrated and horny as hell as I boarded the car train in Sanford, Florida heading to Charlotte, North Carolina. My car was on board as I was going to be staying in Charlotte for at least three months. The Company I worked for was sending me to our Charlotte branch to oversee the start up of a new computer system that I had help develop over the...

Making Friends in Troy, New York

by timmywells on Feb 6, 2018
Gay Male

"Say, would like a ride?" the middle aged man in the aging Ford Fairlane called out as he pulled up to the bus stop where the solitary young man stood waiting for a bus that the older gentleman knew wouldn't be coming for quite a while. "It's the weekend and they only run every hour or so," the man continued after the youth shook his head in response to the...

Mirror Image

by Pelaam on Sep 19, 2017
Gay Male

This is a re-working of a classic as suggested by loves_sg1 More than one pair of appreciative eyes took in the agitated young man clearly waiting for an incoming flight, but his own anxious, jade orbs were oblivious to them all. If he was not staring at the board checking that there was no delay on the flight he awaited, he was looking at his watch. He be...

Exploring my Sexuality

by alexis19901 on May 12, 2020
Gay Male

I'll just start by saying that I've never attended any sauna that may get mentioned in the story. No names that are mentioned are real people either. It's something I've purely put together based on fantasy alone. Thanks for reading! Today was finally the day. I'd been waiting months to go and push myself to try the closest sauna to me which was a short tr...

Love, Lust and Loneliness

by danielblue on Aug 18, 2017
Gay Male

Not for the first time Ralph cursed his rotten luck as he cleaned up the mess other people had left behind in their offices. A scant six months ago he had been one of these office types but that was before he had lost his job and, to add insult to injury, his wife had left him for his boss. Somehow his life had spiraled out of control after that. He had hit...

Tommy Boy

by Northface on Sep 14, 2017
Gay Male

As a young man, I developed a strong attraction for older men. My fantasies, in the main, focused invariably on being seduced and then laid by attractive older guys. In these imaginings, I was eager to follow the lead of the experienced, and always strikingly masculine man that I conjured from thin air. Some of these fantasies were ultimately realized, and I...

Nando and Will Ch. 04

by Pelaam on Sep 14, 2017
Gay Male

Chapter 4: Ceremonies and Consummations The tall dark man stood proudly at the side of his soon-to-be Spouse. His hair, as black as a raven's wing was shining, tied neatly in black silk ribbon at the nape of his neck. His deep brown eyes radiated joy. He was certain that on this day, his perpetually slightly stubbled cheeks were smooth enough to rival those...

Facing the Frat Boy Ch. 02

by thealphamale on Oct 26, 2020
Gay Male

Hey guys! Thanks for all the responses to the first chapter- really glad you guys enjoyed it. Keep letting me know what you guys think. I love reading your feedback. Here's chapter 2. I already have the first couple chapters written and waiting to be released. Ch. 02: What even is Levi Truong? Ryan placed his bag on one of the empty tables at the far edge...

Breaking My Cherry

by bilove69 on Aug 23, 2017
Gay Male

Previously being a happily married 36 year old straight male I couldn't believe after my first fleeting time man to man how much I desired more cock. My first time took me slightly by surprise as I had gone to a nudist beach to look at girls and before I knew it had found me being jerked off by this amazing stud. I wanted more and as much as I tried to resis...