Gay First Time Anal Stories

22,561 results
Orientation
Length
Source
Infinite Scroll

San Francisco Swinging Ch. 02

by KenJames on Dec 4, 2017
Gay Male

* * * * * * * * * * Note: This is a BISEXUAL story. It has male-female sex, as well as male-male sex. * * * * * * * * * * "Did you really mean it?" Fred asked. "About wanting me?" "Uh . . ." Lust fought with fear. Lust won. "Yeah. Whatever you want to do." Fred looked from Andy's stiff dick to his face and smiled. "Man. You're as eager as a horny virgin...

Cross-Dressing, Gay & Lesbian Sex 05

by SusanJillParker on Aug 30, 2017
Gay Male

There are no underage characters in this story. All characters are over the age of 18-years-old. * Daniel's one time bi-sexual fantasy consumes him "Maybe if you allowed me to have sex with Martin," said Emma to Daniel pausing without finishing her thought. She looked at him with teasing eyes and flirty sexiness in the way she used to look at him when t...

Gay Bottom at College (Now Public)

by meris on Feb 1, 2016
Gay

My name is Sam tomorrow is my first day at college I'm 18 and have been gay for a while. I wake in the morning and get out of bed feeling very awake and excited I look at myself in the mirror wild brown hair looking frizzy from my shower the night before yet still looking cute. My emerald green eyes stare back at me hungrily, popping noticeably from my almos...

Open in Reader

Drawn Behind Curtains

by Alluring_Crimson_Shifter on Sep 1, 2017
Gay Male

Joel had a bouquet of roses and was on his way to see his girlfriend Annie. He was in a happy mood. Joel knocked on the door. It was a pleasant day with a bright blue sky, and you could smell flowers and fresh cut grass. Annie opened the door, "Good morning!" Joel stepped in the door, "Here this is for you!" He gave the bouquet of roses to Annie. "For me...

Bathhouse Heaven Ch. 29

by glory_first on May 7, 2018
Gay Male

Riding back after the latest 3 hour bathhouse visit, ass feeling really good in a new way, as if it would love to continue being rimmed and finger fucked for another hour or two. Rarely has a visit started so unevenly, and then ending up revealing - and fulfilling - more about my desires, exposed in a place where they are so easily indulged. Men are not al...

Rear Windows Ch. 03

by KenJames on Nov 12, 2019
Gay Male

"Jesus!" Clark jumped to his feet, staring at the two big sexy black men who'd just walked into the room. They were obviously brothers. Both were tall and muscular with rich chocolate skin, warm brown eyes, and lush lips that invited kissing. One was Clark's height—6' 2'—and the other at least two inches taller. The tall sibling was a serious bodybuilder, w...

Danny Comes to Stay Ch. 02

by Robert_Furlong on Mar 12, 2019
Gay Male

Perhaps it's not surprising that my husband had lost his hard-on while he was watching my ex hungrily rimming my splayed hole. "Just gonna get him nice and slippy," Danny had said before plunging his face into my butt crack and giving me the most intense and satisfying rimjob I'd had in five years. As my old flame was slobbering and slurping away at my bac...

Anal Cherry Busted

by niplock on Sep 14, 2017
Gay Male

Up until a few months ago, I was strictly a heterosexual male. I was never even curious about having sex with another man, but after a divorce and several failed relationships I decided that I needed to at least explore the possibility. So I decided to read up on man to man sex on the internet and check out some of the porn sites to see if I had any intere...

2nd Time learning Oral and Anal

by RandyAlabama on Jan 29, 2020
Gay Male

This is a continuation of my First Time where he fondled, had oral sex with me and had anal sex with me: Jim was a friend of the family. Well liked and popular. He had an easy going attitude. He was 33 years old and I was 18 years old. I had taken him up on his offer to come to his house and we would have some fun. Jim gave me a cola and some Bourbon like t...

Enamored With a Pretty Gay Trainer

by walterio on Aug 18, 2017
Gay Male

THE DISCOVERY Coach Brian Wilson decided to go to his office on a Saturday morning. He was the coach of a small college wrestling team in Southern California. He had already run his five miles that morning so he decided to get some paperwork done at the office. His wife Wendy was playing tennis with the women that morning so he would not be missed. He was i...