Gay Initiation Stories

262 results
Orientation
Length
Source
Infinite Scroll

Big Man on Campus

by EarlytoRise on Aug 18, 2017
Gay Male

September, 1969 Big Man on Campus It had been a fabulous summer, and the amazing experience of having my first real lover still had my mind reeling. Alexander 's abrupt departure left me anxious to be moving on myself. I had no idea how to process the idea that I was a fucking queer, not completely, anyway. I jus knew that the sex had been fabulous and I w...

Initiation

by Castis on Aug 18, 2017
Gay Male

It was a hot summer's evening in South Kensington and I was sitting in my room in our Catholic student hostel. I'd just broken up with my girlfriend and was feeling alone and depressed. The thumping heartbeat of a disco came from the basement. There was one every week. The music got on my nerves at times like this. There are two things I can do, I thought. I...

The Beast Takes Beauty

by blondeallover_00 on Sep 14, 2017
Gay Male

The following is a sequel to my entry in the Halloween story contest of 2007 submitted a year ago. The title was THE TABOOS OF TRANSYLVANIA. * He was so handsome and charming in his dinner jacket that night in August on his eighteenth birthday. Reginald has his mother's big brown eyes and his father's debonair strawberry blond looks. But he inherited his...

Damien's Initiation

by ncdogging2013 on Oct 7, 2019
Gay Male

I had no idea what to expect (or what was expected of me for that matter) as I walked in through the front hallway. I had been in this house countless times and knew the layout well, but everything took on an unfamiliar look now. I instinctively headed toward the kitchen at the end of the hall. This had always been the rallying point any time I came to hang...

Sissy

by MVP6 on Jul 15, 2020
Gay Male

This is my fifth letter describing my expanding awareness from a naive man with a desire to suck a cock to a man willing to explore his seedier side. (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 an unsuspecting man into letting me give him my first blow job. In my second...

Shattered Boundaries Ch. 07

by Humilifuck on Sep 14, 2017
Gay Male

Chapter 7 - "This is how it feels to be fucked by a real man!" I hung suspended in the sling, spread-eagle with my privates displayed like a two dollar whore. He had restrained my hands above my head, denying me any modesty or protection. My legs were spread wide and hoisted into stirrups, laying bare my ass cheeks which now were smeared with lube. My ass-...

The Bike Ride

by rosewall on Sep 14, 2017
Gay Male

At forty two I disliked how out of shape I was. It didn't help that I had just taken a job working behind a desk. I started walking, but that didn't do much to decrease my waist size. After getting frustrated with the spare tire above my belt, I decided to buy a bike. I just fell in love with a 21 speed mountain bike with big knobby tires. After my wife wro...

Yet Another Frat Initiation Story Ch. 07

by Cyanlot on Aug 18, 2017
Gay Male

Part 7: Fraternity Service The morning's activities were once again labeled cryptically, this time as "Fraternity Service". When we got down to the breakfast table, we found that there was no food there. Instead, there was a note that said that pledges were required to service fraternity members before they would have anything to eat. We were to draw a name...

Initiating My Roommate

by blondeallover_00 on Aug 18, 2017
Gay Male

I had repressed feelings for my college roommate before I came to terms with my being gay. I came out my last semester after we had both made other rooming arrangements. Knowing him to be very open-minded, we remained on friendly terms, but I did not have the stamina to reveal my feelings for him. Many of my gay friends and ex-lovers marveled at his slim str...

Taking Out the Competition: Alan

by crazyNorbit on Aug 18, 2017
Gay Male

We had been friends for as long as I can remember. No, "friends" didn't quite describe what the three of us were. The word didn't suggest our competitiveness. Whatever we were was hard to name. It lay silently beneath everything we did, from casual conversation, to sports, to hanging out. It peeked its head out in little things. I'd make a cocky remark after...