Gay First Time Anal Stories

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Finally!

by scrotus on Sep 14, 2017
Gay Male

It has been many, many years since I have been with a guy. I've wanted to have a cock in my mouth and my ass for a long time but it just had not worked out. I had responded to numerous ads on a popular hook-up web site but nothing materialized. By way of introduction and explanation, I am bi-sexual. I have sex with women and cherish my relationships with t...

Gay Fills In for the Secretary

by walterio on Sep 16, 2017
Gay Male

INTRODUCTION Pete Jenkins and Jack Lewis were wrapping up things at the office on a Friday afternoon. They both worked for an investment banking firm and shared a satellite office. The secretary of three years was getting married that weekend and she would not be returning to the firm. Under normal circumstances the guys and their wives would have attended...

Fun and Games Ch. 04

by jm02201960 on Sep 15, 2017
Gay Male

We both got dressed and went out into the living room and he put on a movie called Trainspotting which is actually a cool flick. I relaxed on one of the chairs and we both started to watch it. About halfway through the movie, he just blurted out, "So do you want to fuck each other in the ass tonight or are we done?" I scooted my ass around on the chair as i...

A Wonderful Friendship Pt. 01

by cruiser5050 on Oct 31, 2018
Gay Male

Mike glanced at his watch outside of him home, seeing it was six am, thoughts came out as he started to walk, thinking this is a beautiful warm day. He went for a walk. day, and it will get warm threw out the day. Being sixty-five years old, in good shape from the gym is a good thing, but I still smoke cigarette and marijuana. Everyday I still think of my de...

Jamies Saviour Ch. 02

by alexcarr on Aug 18, 2017
Gay Male

Jamie could hardly sleep being so excited about tomorrow. He felt himself rising like never before, with carnal images in his mind about how it would be, going all the way with Jack. He wondered if it would hurt first time with Jack, he imagined how it would feel with Jack penetrating deeply inside him, he thought about too; that Jack asked for him to suck c...

Painful Sex Is Not...

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

Painful Sex Is Not What I Want Dear readers I shall be telling you about an incident of anal sex with one of my class fellows. The name of class fellow is Martin. It was 1993 and I was just having some very good time as gay in the college and there suddenly I developed a desire to fuck or get fucked by my this class fellow. I actually found him very attract...

Anal Seduction Redux Ch. 03

by wiley4377 on Jun 26, 2018
Gay Male

My ass was sore for several days after my encounter with Hank. His enormous monster caused some extreme stretching. The week was slow at work. I went home on time with no overtime. Boring is the word. Neither Bill nor George had called me to fuck me. So I found myself so horny on Thursday afternoon. The silence was broken when my phone rang. Brnng—brnng—br...

Internet Anal Sex

by fox-for-fun on Sep 19, 2017
Gay Male

This is a true story of mine doing anal sex with a stranger whom I met through internet while having chat on a gay chat channel. It was 24 November 2005; I was at Islamabad (Federal capital) for my personal work. I was staying at a guest room and was alone. In the evening I went to an internet café for web browsing and chat. I had heard from my fellows that...

Bottoming with My Mentor Pt. 02

by shadoblivion on May 22, 2019
Gay Male

Once again, this story is entirely fictional. Names are changed. ***** It had been over a decade since I last saw Fred because of a falling out due to a miscommunication. Not long after our intimate experience together, he had tried to contact me to hang out casually but I was indisposed and couldn't meet up. He took this as a slight, like I was blowing...

Taking the Big Step Ch. 02

by Shady_Lady on May 1, 2018
Gay Male

When I wrote "Taking the big step" I was incredibly nervous because as a female writer I had no idea how it would be received. To my pleasure (and surprise) it was well received, and based on the positive feedback, I decided to write Chapter 2. This is a direct sequel to 'taking the big step.' Once again, if I got any details wrong, please forgive me. *****...