Gay First Time Anal Stories

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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...

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...

How Life Changes Ch. 01

by bigskyben on Aug 18, 2017
Gay Male

A couple of years ago I wrote a couple of stories for Literotica and told about my first and only gay encounter when I was 19 year old guy. I never had another until my wife passed away 18 months ago. My life changed and so did my wanting for gay sex. I was on a project and in Anchorage, Alaska and started out marching in the Gay pride parade. I started vi...

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...

Anal Peep Show

by wiley4377 on Oct 11, 2017
Gay Male

PEEP SHOW XXX ***It is not recommended to have unprotected sex with first time partners. I was first fascinated at a book with a variety of pictures of men fucking men and women. The anal intercourse was especially arousing.*** It started when I was 19 and for the next five years, I enjoyed anal intercourse with several men. Two men were regular visitors...

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...

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...

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...