Gay First Time Anal Stories

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28-year-old Bisexual Stepfather Ch. 05

by walterio on Feb 6, 2018
Gay Male

AUTHOR'S NOTE: This story contains straight sex, bisexual sex, gay sex and incest. DUSTIN GIVES IN TO HIS ANAL DESIRE It had been weeks since Dustin had anal sex and Brandon would not be home for another four weeks. He had not been with the sisters and he was still haunted by the scene with Rick and Tyler. The consulting gig had wrapped up and he was now a...

From a Finger to Fucking Ch. 02

by the_apocalypse on Aug 31, 2017
Gay Male

For the next few days I didn't leave the house until the post had been delivered, and I was getting more and more frustrated each day that it came without my order. I had even given up going out at night and looking for a woman, instead I would spend the nights in my room with my finger up my ass wanking until I eventually came. Finally, one week after I ha...

Never Say "Never" Ch. 03

by walterio on Mar 16, 2020
Gay Male

THE WORK WEEK BEGINS Ted was up at 5:30 to make coffee and get ready for the 6:00 AM conference call. He peeked at Erin lying naked in bed on his belly. His gorgeous ass was poised for the taking but Ted maintained his discipline. It was going to be a long day with calls and scheduling appointments. Erin was no bother and never interrupted Ted except to r...

Being A Gay, Flash Back From Past

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

I have been very curious about my anus and have been playing with it since child hood. But once I turned eighteen I became a bottom. As a bottom my favorite pass time activity was to bend over before dressing table mirror and open my hips and shove lipstick or hair brush in my anus and then move it in and out of my ass for hours, of course I always applied s...

Anal Sex with Stranger on a Train 04

by SusanJillParker on Sep 19, 2017
Gay Male

Peter telephones Robert for anal sex to finish what he started on the train. "Hello?" "Hi Robert. This is Peter. I, um, met you on the—" "I know who you are Peter," said Robert. "It's not every day that a stranger pulls up my dress, pulls down my panties, and fucks me up the ass on a crowded train," he said with a laugh. "Please call me Roberta." "I was...

Joe's Extraordinary Library Visit

by Jack Gates on Aug 18, 2017
Gay Male

Being an author on Literotica I get a lot of feedback from both male and females concerning first time anal sex. From women who are curious because of pressing lovers who keep asking them to bend over backwards to please them. Then there are bi-curious guys desperate to feel a cock inside their bums and scared stiff to ask a guy to do it. Personally, I was...

Black Cock Addiction

by JHelper on Aug 18, 2017
Gay Male

This is a true story about my sexual experience. To anyone who's reading this, I hope you it helps you figure out your own sexuality and what you want for yourself in life. To introduce myself -- I'm a 26 year old white guy, and I'd describe myself as straight, masculine, and very good looking. I have a fairly dominant personality and I'm a member of the U...

He Becomes Addicted to Twinks Ch. 02

by walterio on Oct 3, 2018
Gay Male

It had been six months since Jack hired Michelle and things had gone extremely well. Michelle proved to be a quick learner and had become an excellent programmer. Even Paul and Bob had to admit that. At first, they were upset with Jack as they did not like the idea of a gay guy working in the department. However, Michelle kept to himself and worked hard. Ja...

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....

One Night Stand Ch. 01: Nick

by KenJames on Dec 9, 2019
Gay Male

I'm leaning against the wall near the door at Dirty Sally's, nursing a beer. It's about noon on Sunday. This is a Labor Day weekend so the crowd is even bigger than usual. I'm a little shy in bars. Especially crowded noisy bars. It doesn't matter. I can just hang out in a gay bar and a guy will hit on me. I'm not handsome, but I am tall, rugged, and moderat...