Gay Penetration Stories

1,000 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2026 SmutMD.com

Orgasm by Anal Penetration

by Eagerbottom on Aug 18, 2017
Gay Male

I grew up in a Pentecostal family in Holland, but deled in silence with liking men. I get married with a woman and to my sadness after seven years I got divorced. Though I had not gone to church for a while, I started to go to one, in Amsterdam. I was already in my thirties. I did a bit of work out, but was too tiny to my taste. I liked to meet other people....

My First Gay Anal

by dkmywife on Sep 25, 2017
Gay Male

My first full penetration gay sex experience was with my FORMER gym teacher the summer after graduation. I was 19 and legal...graduated so he was no longer my teacher. Unlike so many gym teachers he was actually fit with broad shoulders teeny waist and a decent look to him. What none of us knew, at least what I didn't know was that he was gay. The first mont...

His Loving Beauty Ch. 02

by AaronCromwell on Sep 16, 2017
Gay Male

Even though the penetration hurt like hell most of the time that first night, despite Damon's tender loving, the sex was still incredibly fulfilling. It was the way Damon's body on top of mine completely immobilized me as I lay on my stomach. It was how he consoled me with sweet whispers into my ear, telling me, "I got you, babe," while pumping in and out of...

A Sunny Afternoon

by Pissdrinker on Mar 6, 2018
Gay Male

Please note that a condom was used during the penetration involving myself and the stranger, something I have omitted in this version of the story. Safe sex guys, always. *************** The back of our house isn't overlooked, only if the guy next door who rents some of our land is working there do we see anybody. If it's a warm day, we can sunbathe withou...

My Journey Ch. 02

by lonesomejones on Sep 14, 2017
Gay Male

We cuddled in silence for a while. I felt fully relaxed, if not still a bit tipsy, enjoying the afterglow of my first penetration and the feeling of fullness in my bottom. There was a very slight breeze and the moon was illuminating the spa and deck. After a while I climbed out of the spa and went to bed where I slept soundly until morning. I woke up with mi...

Jasper's Touch

by alexcarr on Aug 18, 2017
Gay Male

Jasper felt so good as always. His warmth passive and constant inside me as he did what he always did when we fucked, he paused clutching my shoulders so tight in order to get a maximum penetration- leaning behind me as I was bent astride the kitchen table - with cushions heaped neatly beneath my front for my comfort. Jasper was always the considerate lover...

I Thought I Wanted It Rough...

by LonelyVirgin on Sep 14, 2017
Gay Male

Let me start off by saying I'm straight. I'm very attracted to women, but feel absolutely no attraction to men. When I was younger, I always had a fascination with anal sex. I don't know why, but from when I first started looking at porn on the internet, I was always looking for anal sex. The odd thing was, I wasn't so focused in on the penetration of all...

Seduced by a Friend Ch. 03

by yorie on Sep 14, 2017
Gay Male

Following the painful fucking with Howard and John at Dave's place, I swore I would never go near gay sex again; I could not come to terms with what I had done, and had done to me. I was very disturbed about the day's events and the intense pain I got when Dave brutally fucked my ass for over an hour. All I could remember doing was absorb the pain, and keep...

Seduced by a Friend Ch. 02

by yorie on Sep 14, 2017
Gay Male

Howard and I did not get together after he first seduced me into the gay scene. It gave me a chance to reflect on the many sex acts I had performed with him, and in my own time I could come to terms with what I had done, and had done to me. It also gave me the chance to determine whether I wanted to carry on with this new sexual awakening or turn away from i...

Twister

by alexcarr on Aug 18, 2017
Gay Male

Danny and I were making it in the kitchen, to be more precise, over the kitchen sink. He had it on him that he'd catch me when I was doing the washing up after a meal. I always dished up something for him when he visited. But a knock at the front door put the mockers on that. We could have just ignored it I guess and carried on fucking but then, well I'd be...