Gay First Time Bottom Stories

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Assuming the Position Ch. 01

by bi golly on Sep 25, 2017
Gay Male

I had been playing with my ass before I even learned to jack off. Playing with my anus felt good and I liked it. When I learned to jack off, I did that for a while, but soon added anus play and fantasized about being fucked. First it was that I was going to get tricked into getting fucked, but then I was honest with myself. If a guy I could trust ever wanted...

A Teen Seduced and Hooked on Anal Ch. 05

by walterio on Jul 29, 2019
Gay Male

ANOTHER WEEKEND BY THE BAY Traci slept in on Saturday morning as she was dead tired from a hectic Friday night at the club. She needed her rest before another busy Saturday night. Eric and Scotty went out for breakfast and did some more local sightseeing around the city. They ate lunch by the Wharf and later returned to the apartment. Traci had already left...

Never Say "Never"

by walterio on Mar 2, 2020
Gay Male

Ted woke up on Saturday morning to the sound of heavy rain. Normally he played golf but he knew it would be rained out. He turned toward Erin who was still sleeping. They were both naked as they had remained that way after having sex the night before. He slid the bedcover down to reveal Erin's super fine ass. Ted loved fucking that ass and with golf rained o...

Bottom-Slayer: 1st Bottom Slain

by silkstockingslover on Sep 14, 2017
Gay Male

Bottom-Slayer: 1st Bottom Slain Summary: A black stud learns white boys are great bottoms. Note: A special thanks goes to Estragon for editing my work and for providing assistance in a crucial scene in the story. Note 2: Of course, all participants are 18 years old! * BOTTOM-SLAYER: 1st Bottom Slain PROLOGUE: Now let's get something straight (pardon...

Journey of a Middle-Aged Man Ch. 02

by bdavidson on Mar 12, 2019
Gay Male

Before my two awesome bottom encounters with Don and Pete, I had met and had sex with other men, which were fun, but didn't meet my expectations in one way or another. Early on, I was just groping around, not sure of what I wanted or how I wanted it. But, looking back, each one set the stage in some way for what was to come later in my life, when I lay on my...

The Harrington School for Boys Ch. 03

by AgentK on Nov 27, 2017
Gay Male

It was around midnight on a Thursday night, and Graham Ainsley was sleeping soundly when suddenly he was startled awake by his bedroom door opening and a light turning on. He looked up to see the prefect, Reed Burgess, dragging his roommate Aidan by the arm. Aidan appeared to have been crying. Reed pushed him roughly towards the bed, giving him a scornful lo...

An Enjoyable Bisexual Encounter 01

by walterio on Aug 30, 2017
Gay Male

PRELUDE Kurt woke up Saturday with a morning erection and he rolled over expecting to find Sandy but the other bed was empty. Kurt was disappointed that Sandy had already left his bed as he would have loved fucking that curvy ass first thing that morning. He reached down and took a hold of his 7+" thick cock and stroked it slowly. He thought back to last ni...

Vaseline, My Best Friend

by 46204_zipper on Aug 18, 2017
Gay Male

I grew up in Arlington Heights, Illinois, and was a late bloomer. I was also a geek, but in the mid-1960s we didn't use that term. I was a serious student who liked technical subjects and military history. Most of my free time in high school was spent playing basketball with my male friends. I had dates but most girls did not let you do anything except fondl...

Family Offerings Ch. 03

by walterio on May 23, 2018
Gay Male

START OF ANOTHER WEEK On Tuesday morning after Martha left for work Aaron arrived at the house. Now that he had fucked Martha, he would have to figure out have to balance his time between mother and son. He took of his clothes and left them in the family room before heading to Chris' bedroom. Aaron got in bed and slipped under the covers. He felt the slen...

One Disgusting Pervert

by Formosa46 on Aug 18, 2017
Gay Male

You seemed genuinely surprised when I reeled around and grabbed your wrists quickly pinning your hands above your head against the wall. With my face right in front of yours I looked you in the eyes and taunted "Dan I'm about to prove you are one disgusting pervert." We had been exchanging steamy texts for over a month. Sheepishly trying out new possibilit...