Gay First Time Anal Stories

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First Time Anal

by iamcontent on Sep 14, 2017
Gay Male

I have always known I was bisexual since I was a kid. I have topped but never bottomed, I have attempted bottoming a few times. First time I was in my teens and my friend and I tried, we didn't have lube and I wasn't stretched out properly. A few months ago I bought a butt plug which is 4 inches long and a 8 inch dildo. I lube every night and put the plug in...

First Time Anal

by ironclad75 on Aug 18, 2017
Gay Male

First time writing, so decided on a real story: I'm a 35yo divorced guy, and have known I was bi-sexual for some time. I am 6'3"200lbs and well built. I am fairly smooth, attractive, with a nice cut 8" cock. As a former college lacrosse player, I've been around the typical jock-world for a long time. My friends are straight, and I am very discreet about my...

Femboi has First Time Anal

by Alluring_Crimson_Shifter on Oct 8, 2019
Gay Male

Jacque was coming over and Ryan waited in anticipation. Finally he heard a knock on his apartment door. Opening the door he greeted Jacque for the first time in months. Both were starting college. They gave a hand shake and a hug to head and shoulders, with a hand around each others back. "How are you?" Ryan wanted to know. "Fine, you look as good as ever,...

First Time Training Session Ch. 02

by playtime2728 on Aug 30, 2017
Gay Male

My throat was sore for a week. It got so bad that I lost my voice-my friends were all telling me to go to a doctor to see if I had strep, while I was secretly turned on every time I tried (and failed) to say something. No one suspected in the least that I was whispering because a strange guy with a big dick had given me an hour long lesson on what deepthroat...

Straight Cocksucker: 1st Time Anal

by silkstockingslover on Nov 26, 2019
Gay Male

Summary: Married cocksucker has crazy submissive night including anal. Thanks: To Robert, Wayne and goamz86 for editing. Straight Cocksucker: First Time Anal Once you have crossed the imaginary line between straight and gay, once you drop to your knees and fish out a stiff rod from a stranger's pants, once you have had a cock in your mouth, once you've...

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...

Nympho Discovery, Love of Cocks

by Alluring_Crimson_Shifter on Aug 31, 2017
Gay Male

Ricky was getting ready for his first sales convention with his new job. He hoped he would make a lot of valuable contacts. Looking in the mirror he straightened his tie, and practiced a charismatic smile. For a 19 year old he was confident and knew he would be successful in his new sales career. He had opted to postpone college and try making a successful c...

Cross-Dressing, Gay & Lesbian Sex 05

by SusanJillParker on Aug 30, 2017
Gay Male

There are no underage characters in this story. All characters are over the age of 18-years-old. * Daniel's one time bi-sexual fantasy consumes him "Maybe if you allowed me to have sex with Martin," said Emma to Daniel pausing without finishing her thought. She looked at him with teasing eyes and flirty sexiness in the way she used to look at him when t...

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...

My Life is You Ch. 08

by mypussyandyours on Sep 19, 2017
Gay Male

I TRULY WANT TO THANK EVERYONE WHO HAS BEEN SO WONDERFUL ABOUT GIVING ME FEEDBACK. IT’S NICE KNOWING THAT YOU ARE AS INTERESTED IN DILLON AND SETH’S STORY AS I AM IN TELLING IT. OK: STANDARD WARNING. THIS IS A NON-SEX CHAPTER. THOSE TEND TO HAPPEN WITH ME. YOU HAVE BEEN WARNED! LOL Dillon felt a huge sense of accomplishment as he made his way down the ha...