Gay Anal Virgin Stories

6,401 results
Orientation
Length
Source
Infinite Scroll

First Time Gay Anal and Breeding

by RoughBreedingLover on Sep 25, 2017
Gay Male

I've always wondered what it felt like to receive a creampie, at 24 years old I finally decided to post an ad on Craigslist. The ad was named "wanting first time gay anal with a deep breeding creampie." I wasn't interested in blowjobs and anything I just wanted to be topped really hard, balls deep with the absolute minimum amount of lube so I would really...

Pegging Peter Ch. 06

by KenJames on May 23, 2018
Gay Male

Peter kept thinking about his first time during the drive to Mark's apartment. He and Janna had been dating for two years, gradually progressing from tongue kissing to mutual masturbation. The last time, in the back seat of his dad's Suburban, he'd pulled her panties down, then eaten and fingered her to orgasm. She'd given him a great blow job. After he'd c...

Anal Sex for the First Time

by niplock on Sep 14, 2017
Gay Male

I have been a bi-curious male for some time. I tried going to gay bathhouses, nude beaches and even steam rooms at a local gym to explore my gay feelings. Up to this point, the only gay sex that I had experienced was sucking on a few cocks here and there. The most erotic experience was being naked in a porn movie room at The Club with a naked man sucking my...

Anal Sex Ch. 04

by fox-for-fun on Aug 18, 2017
Gay Male

I have been doing this anal sex, since 1985 but the best anal sex I did was in 1997 with a very cute young teenage boy of about 19 years of age. He became my friend while I was coming to my hometown by air from some other city. He was a very shy person and never had any sexual experience except playing with him self. Since we had become good friends, so we w...

My First Time

by GayGuyJason on Aug 18, 2017
Gay Male

I'm like most average nineteen-year-old guys. Struggling to find a job, trying to get into school, that sort of thing. I also suffer from Bipolar Disorder, and when on and off my meds for varying degrees and reasons, I tend to get extremely horny. This eventually eclipsed over one weekend until, eventually, I could take it no more. I was jacking off three ti...

How I Lost My Anal Virginity

by silverbullet2211 on Aug 18, 2017
Gay Male

This is a completely true story as to how I lost my anal virginity about a year ago. This is also my first time posting on here. Constructive criticism is more than welcomed. Hope you enjoy. ***** I had previous success with posting to Craigslist. I had met a few times before, but it was just for some oral play. Ever since I was eighteen I wanted to be fuc...

Valentine's Day at the Gym

by schaeff on Sep 14, 2017
Gay Male

(Author's note: This fantasy happened some time ago. Long before STDs were a known threat. If the time of these events were more recent, certainly safe sex precautions would have been followed - and recommended.) * After a long, hard, aggravating day at my job, I packed my bag and went to the Gym for a stress reducing workout. After warming up on the stai...

Taking the Big Step

by Shady_Lady on Aug 18, 2017
Gay Male

As a female this story makes me nervous about its content, not because of the subject matter, but because I have no idea if I have got the actions and feelings right. I would love to get any feedback but especially from any gay or bi male readers as to if it works or not. If it doesn't work I apologise but hope you enjoy. ******************* A whole weeken...

Joe's Extraordinary Library Visit

by Jack Gates on Aug 18, 2017
Gay Male

Being an author on Literotica I get a lot of feedback from both male and females concerning first time anal sex. From women who are curious because of pressing lovers who keep asking them to bend over backwards to please them. Then there are bi-curious guys desperate to feel a cock inside their bums and scared stiff to ask a guy to do it. Personally, I was...

First Time Fears Overcome

by JASONSHOMOEROTICA on Aug 18, 2017
Gay Male

A Help for Timid Young Gays A homoerotic tale ***** CHAPTER 1 Serge had been fucking his partner, Chris's arse for several minutes with ever increasing amplitude and force, when he suddenly felt that magic something in his cock which was the intimation that the climactic moment, that incredible sensation when he would reach what had the makings of being...