Gay Anal Gaping Stories

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Doing the Dirty Pt. 02

by Robert_Furlong on Aug 30, 2017
Gay Male

It's odd but strangely compelling to watch your own son masturbating right there in front of you. I was fascinated to see how different his technique was from my own - his hand seemed so much more frantic and his fingers more agile - while marvelling at so many physical similarities between us. His cock was ever so slightly bigger than mine, but other than...

Peter Three Hundred

by exaucer on Sep 14, 2017
Gay Male

John was a distinguished looking man and ever so friendly. Young Peter was not exactly sure what he did in the hotel but he always seemed to be on his floor when Peter came out of his room or in the foyer when he returned to the hotel after work. John was such a big man, very handsome in a rugged sort of way and always took the opportunity to put his arm aro...

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. *****...

Escape of the Schlange

by sr71plt on Aug 30, 2017
Gay Male

On Sunday, April 28, 1793, the bells in towers of the harbor town of Charlotta rang out at 2 p.m. They were calling all nobles on the inland sea island of St. Silvus to the wedding of Reginald Reynolds, the governor-general's son, the most magnificently formed and handsome of the most physically gifted countrymen on the face of the earth. At that precise mom...

First Anal, with a MAN Pt. 02

by DougsLair on Nov 5, 2018
Gay Male

As I was driving home from Fred's, I was already wanting a next encounter. I'm lucky I made it home without having a major accident, my mind was hardly on my driving, or other cars and trucks on the road. Dangerous, I know. I made home safely, pulled into the driveway, and got out of the car. I noticed two things, right away. First, how incredibly pleasant...

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...

Dirty Butt Sex: Anal Threesome

by DirtyButtSex on Sep 4, 2017
Gay Male

I should start out by stating that the following story is true. I'm 28 years old and I've had sexual encounters with both men and women. While I lean in favor of being with women for dating purposes, I enjoy sleeping with men more. But perhaps the term "sleeping with" is not entirely accurate; I enjoy being fucked by men. Butt sex, as they say, is the best....

Return from Spring Break

by WFEATHER on Aug 18, 2017
Gay Male

The anal plug was buried deep within me, and as I tapped on the base of the thick, hearty plug, I once again felt a thrill as I felt he vibrations of that tapping cascading into me. With each tap, my breath caught briefly in my throat, and my manhood throbbed against the pillow beneath me. Yet part of the exhilaration of the moment was the noise coming from...

Surprise First Anal Experience

by BottomBoyUK on Jul 9, 2019
Gay Male

I was 21 and had just finished at university. I knew I was into cock and had sucked one before but had been too nervous to take one in the ass. To me it felt like crossing a threshold into being gay that I wasn't sure about. I had been chatting to a man called David online, who lived in my town for months by this point, and he made me feel comfortable enoug...

First Time With A Man

by Willing2Do on Apr 3, 2019
Gay Male

His knob pressed into my anal spinchter. It felt somewhat like a raquetball being shoved up my ass but different; round, hard, yet yielding as my anus gave way to its invasion, but warm, wet and pointed on the end. The rod pushing it into me was a bit thinner, but also hard and at the same time soft, fleshy, thickly veined and slimed with the lubricant he ha...