Gay Naive Stories

395 results
Orientation
Length
Source
Infinite Scroll

Toby's Story Ch. 2

by RobbyRoberts on Aug 18, 2017
Gay Male

Chapter 2: Thursday Afternoon After school on Thursday, I rushed over to the health club again. I was very pre-occupied and spent most of the time keeping an eye open for Tim, but I couldn't see him anywhere. I was really disappointed and was starting to think that perhaps the encounter was only going to be a one-time thing. While I was having a shower, th...

A Hidden Life - First Time

by ASubmissiveCocksucker on Sep 4, 2017
Gay Male

As a young man, I had discovered many men went to public restrooms and masturbated while other men watched. Often times this was done through peep holes in the walls separating the stalls. Older restrooms would not have doors to the stalls. Sometimes men would masturbate at the urinals. I knew some men would play with another man's penis, either jacking him...

Alcohol as a Crutch

by timmywells on Aug 17, 2017
Gay Male

Paul had made it to the bed, but not into it. Instead, most of his slender 6' frame was sprawled across it, with his legs hanging over the side as he lay face first on the bedding. His tangled underwear were down to his knees and the only clothing left on him were his white athletic socks. We had been drinking, like we did every Saturday night, and just lik...

Roasting Rob

by reggie365 on Aug 18, 2017
Gay Male

I met Mike through an old flatmate of mine. Her name was Leanne. She fancied him like mad. He had bedded her a couple of times before we met. I think she realised he just wanted to fuck her if she was ther and nothing more. That was the kind of relationships she attracted. Anyway we went round to his house one night and got stoned and drunk. High and horny...

Banister Guy

by alexcarr on Aug 18, 2017
Gay Male

Banister guy. I suppose life is full of surprises, so when Henry asked me around to play some games - well was I naive or something in never imagining they would be the type of games he had in mind? "I have fancied you ever since I employed you in my company Peter" he confessed, and there was I thinking it was because of my academic ability. You see what...

The Couple Pt. 01

by YifftuSome on Jun 1, 2020
Gay Male

People who know me, describe me as absent minded and easy going, and rightfully so. I have always tried to get better, but finally accepted the fact that it's in my character and can't be changed. Why did I say this? Because I should have tried to change. I have two apartments, a small one upstairs and a bigger, more luxurious one on the ground floor. I li...

Gym

by MVP6 on Oct 5, 2020
Gay Male

This is my seventh letter describing my expanding awareness from a naive man with a desire to suck a cock to a man willing to explore. (M+M, oral, anal) In my first letter "Costume in a Costume" I describe how I dressed as a girl in a Halloween costume to trick unsuspecting men into letting me give them my first blow job. In my second letter "Gloryhole Il...

Business & Pleasure Ch. 01

by nero957 on Sep 5, 2017
Gay Male

Chapter 01: My First Time I have read several stories about first time encounters and realized that my first time was both interesting and maybe intriguing reading for others. I was 39, happily married with 2 children and in a very hectic business world. While I had thought of encounters with men, it was always just a fantasy. In the sports dressing rooms,...

Taking the Step Ch. 01

by texas0791 on Oct 15, 2017
Gay Male

It has taken me 3 years to get the nerve to put this to paper, but it is something I feel I finally must do. What follows is a true story of fantasies, curiosity, lust, desire and ultimately satisfaction. Enjoy . . . Like so many men in these stories, I was your typical heterosexual married man, in his mid 30's, who was pretty sure where he stood in life....

Teen's First Time

by TallNavyMan on Aug 31, 2017
Gay Male

Everybody has read a story about a first time and they all seem too unbelievable, but mine really happened this way. I was 19 years old and at the age when my dick was hard all of the time. I had never done anything with a guy at that point in my life and really never thought about it. I was working at a Convenient Store downtown and had to pass downtown t...