Gay First Time Stories

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If You Drop Your Wallet In P'town

by 69plus1 on Sep 17, 2017
Gay Male

I was about 23 and only out of college a couple of years. I was working for a hotel and restaurant supply company spending half of my time at the home office in Boston and the rest on the road. I had grown up in a small town in central Maine and going to school in Cambridge Mass was a real eye opener on many levels. The most exciting was my exposure to sex...

My First Encounter With a Man

by Just_TM on Sep 14, 2017
Gay Male

I found myself there more by accident than on purpose. Or so I tell myself anyway. The fact of the matter is that I was yearning for this new experience for quite some time. There was just something enticing about man to me even though I was (and still am) quite the ladies man. For years I was "curious". My first true step was to buy a Bi video. The sight I...

First Plane Ride Alone Opens Doors

by seanspence on Aug 18, 2017
Gay Male

First Time Flying? So it was time for take off. The attendants and the captain announce the normal flight procedures and the safety precautions. Just to be clear, this wasn't my first plane ride. I've been on tons of flights. Just that this was the first time I was flying alone. I'd been really nervous this morning about this. Especially cuz my first trans...

Bumping into Phil

by alexcarr on Aug 18, 2017
Gay Male

It was just by coincidence really that I bumped into Phil in the street one day. I say coincidence because after he'd almost knocked me over and strived to help me keep my balance, there we were laughing our heads off and he saying "I think I owe you a drink, sorry about that" He was some big fella to be sure but had a fine stance about him, about the same...

My First Taste

by MrE352 on Sep 14, 2017
Gay Male

They say you never forget your first time. Although it's been nearly 20 years, I can still remember it well. It was January of 99 and I had just turned 18. My parents went out of town to celebrate their anniversary for the weekend, and that meant one thing for me. Busting as many nuts as I could. I called my girlfriend at the time to try and make plans. L...

Eighteen Goes Into Thirty Six Twice

by danielblue on Sep 25, 2017
Gay Male

Jerry cursed as he whittled away at a stick. He was bored shitless, and as horny as hell. Trouble is, he didn't know what to do about it. He wanted nothing to do with the girls in his small town, although they all chased after him like he was the only guy in town. All Jerry wanted was to get his hands on a guy. Night after night he lay awake in his room str...

Giving Myself to You

by Matureexplorer62 on Apr 21, 2020
Gay Male

Up until recently, I had never really thought about myself as bisexual, but after my thirty plus year marriage ended a few years ago, perhaps it was time to explore my sexuality a bit, maybe open myself up to some new experiences. While I have had a number of interesting experiences with several women I have met over the last few years, lately, I seem to hav...

About a Minute or an Hour

by ThePurpleDragon on Nov 18, 2019
Gay Male

It was another time for sex and the internet. Cams weren't on every computer yet, and it wasn't necessarily a thing in chatrooms. It took a long time for even a picture to load, so imagination was key. People talked in sexually charged chatrooms, some using present-tense narrative structures to play-act sex (it was called "cybering"), and some just talked to...

Forbidden Fruit

by silverace1 on Aug 18, 2017
Gay Male

I was twenty-eight when I first met James. Not Jim but James. He was 33 years and a beautiful man; dark wavy hair, deep blue eyes and strong chiselled features. Sort of a GQ model type. I on the other hand was thin, silver-haired (as I had been since I was seventeen) and very unsure of my self in the ways of the world. I had only had a few dates with girls...

An English Boy Gets Turned Out Ch. 03

by RustyRover on Sep 14, 2017
Gay Male

Mr Tobias was at work earlier than normal today. He had an early meeting with Mick to discuss the new star of their porn website. The Porn industry used to be a license to print money but that had changed over the last few years. Now there was more free porn available than paid for porn. Between Porno YouTubes knock offs, torrents and all these other sites e...