Gay Anal Fingering 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...

Pantomime Cow

by Robert_Furlong on Aug 31, 2017
Gay Male

Part of the 'Butt Monkey' series of stories by Robert Furlong === Jake mentioned over tea that the drama department at his college was looking for someone to help out with the Christmas pantomime. It was still early November but rehearsals were already underway. "I didn't think you were interested in drama, Jake." "I'm not actually in it," he replied, th...

Paul's First Assfucking Pt. 01

by JohnLeslie on Sep 17, 2017
Gay Male

My name is Paul, I am 40, tall, athletic, handsome and masculine. My girlfriend Michelle, is a cute 21 year old college senior with long black hair, a slightly curvy body and big boobs with sand dollar like nipples. We have an amazing sex life and often fantasize about threesomes and foursomes. Usually, I am very dominant sexually with her and the other wome...

Exploring My Bi Side Ch. 02

by bscurious1 on Oct 19, 2020
Gay Male

Randy and I kept up our meetings, sometimes weekly sometimes two or three times a week, just depended on our schedule and how horny either of us were. We always met at his house in his home studio which offered us a lot more privacy and freedom. As I had stated the massages pretty much stopped but he would still give me one when I needed one or just wanted o...

It's A Slave World After All

by KingAngle666 on Feb 4, 2019
Gay

Everyone who turns 18 dreads/looks forward to Reveal Day, a day that occurs once every six months. Today is your reveal day, just as it is the reveal day of your twin brother. You're more nervous than your brother who is confident everything will go his way, because it tends to do just that, you may be fraternal twins but you don't share the same gift of goo...

Becoming an Anal Sex Whore Ch. 02

by Patrick2380 on Sep 14, 2017
Gay Male

I recommend reading the first part of this story if you have not already done so. Please, feel free to give me feedback, scenarios you would like to see in future parts of this or other stories or anything else. I love hearing what people think, especially if this turned you on. * "... Now, I want you to go stand in the shower," he commanded. "Don't turn o...

Becoming an Anal Sex Whore

by Patrick2380 on Sep 14, 2017
Gay Male

"So, what made you decide to post your ad online tonight?" he asked as I we walked down the hall of my apartment building. "I don't know," I replied. "I guess I am just really horny and wanted to try something new." I knew, though, why I decided to post the ad that read "28 year old male looking to have sex with a man for the first time. Please, be open to...

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....

Big Brazilian Cock

by arkangel55 on Jun 5, 2018
Gay Male

Gay Blowjob Anal Submission Domination Not sure how to start other than this is a true story about two men who meet on the now defunct Craigslist Personals. It was in December. About two weeks before Christmas. He had come to my city from Brazil, but New York more directly. I was on the rebound from a busted relationship. My MO was to try to hook up with a...

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...