Gay First Anal Stories

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Infinite Scroll

Steve and Kyle

by JASONSHOMOEROTICA on Sep 5, 2018
Gay Male

CHAPTER 1 Kyle Sinclair, the main character -- let us call him the hero -- of this story, is a Chicagoan; active, young, muscular, sexually superbly equipped and totally gay. Kyle comes from a working class family living in the western suburbs of the city and has never paid much attention to learning anything at school, which, when he was eighteen he left r...

Blow and Go Ch. 03

by Jay142 on Aug 12, 2019
Gay Male

It had been more than a month when my colleague Peter and I became suck buddies at a conference while we shared a hotel room. Our cheap company brought us together and the rest is history. Not only did I find another dick to suck but Peter also returned the favor and he found out he enjoyed sucking a dick as much as I do. Our schedules didn't allow us to ho...

Convenience Store Sex

by walterio on Sep 14, 2017
Gay Male

I stopped by the convenience store on my home from working out on Saturday morning. I was in the mood for a fresh cup of coffee and something to eat. I didn't feel like fast food or stopping at the diner. When I entered the store there were two people working there and I noticed that one of them seemed to check me out. The guy checking me out was actually ki...

First Time With Joe

by alexcarr on Aug 18, 2017
Gay Male

I was so pleased and happy when I started to realize my true leaning. For years I lived under the misconception that, because I wasn't particularly attracted tin a physical sense o girls, there was something fundamentally wrong with me. It didn't occur to me that I was gay or anything like that. There were guys who turned my head for a second look but that...

Leather

by fadedgiant on Aug 18, 2017
Gay Male

I was not sure what happened or why; really, I didn't care. I felt Jerome penetrating me and knew he would be my no tell lover. I am married to a sexless woman who won't touch me or let me touch her. Jerome pressed more of his thick hard shaft deeper into me. I wasn't sure what a swoon was but I think I swooned. Further his man meat went, deeper into my wai...

Jack & Walt Ch. 02

by lovebuns on Aug 18, 2017
Gay Male

[This is my second offering here at Literotica. I had several responses to my first story, and found that I loved hearing your thoughts, praise and criticisms...please let me know how you like this one!] It had been a little over three weeks since that surreal Friday evening that I lost my anal virginity to my roommate and best friend, Walt. We had both bee...

Before We Go Home Ch. 01

by kill4abutt on Aug 18, 2017
Gay Male

We both have the same Christian name, which we had found out about when we attended the same boarding School, where normally you only called somebody by their surname. Masturbating oneself was the normal way to relieve the sexual tension there. Some though were with the company of another boy whilst thinking of your relative girlfriends; some however, went b...

My Real First Time Ch. 2

by janvanwyk on Sep 1, 2017
Gay Male

This is just a carry on what happened between me and Joe after our first meeting: The next morning I woke up next to Joe and I immediately felt my anus which was really uncomfortable with a dull ache, this was probably not surprising after the night of fucking I had gone through with Joe’s very big and thick cock. I got Joe’s telephone number and left cat...

It's About Time Ch. 02

by oldfloridaboy on Aug 18, 2017
Gay Male

Having just fulfilled a long time fantasy of sucking a cock and having a load of cum shot on my face my friends suggested we take a break and have a few more drinks before my next lesson. It turns out that Tony and Rob were into what they called flip flop where both would either top or bottom during anal sex. Again as I had mentioned in my first story, in my...

28-year-old Bisexual Stepfather

by walterio on Jan 31, 2018
Gay Male

Editor's note: this story contains scenes of incest or incest content. ***** VISITING THE LOVELY BOTTOM In what had become fairly routine over the past couple of weeks, Dustin walked down the hall to his stepson's bedroom. His 40-year-old wife Margaret had already left the house leaving her 28-year-old husband at home. As usual, Dustin had fucked Margaret...