Gay First Anal Stories

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My Girlfriend Would Like To See Two Men

by CindyUSA on Aug 18, 2017
Gay Male

My girlfriend would like to see two men have sex Each person remembers their first time for the major events in their lives such as going to school, a date, kiss, and sexual intercourse. For the more adventurous, anal sex can be enjoyable for both the person receiving (bottom), and giving (top). On study has reported that 40% of married couples had experime...

Bottoming with My Mentor Pt. 02

by shadoblivion on May 22, 2019
Gay Male

Once again, this story is entirely fictional. Names are changed. ***** It had been over a decade since I last saw Fred because of a falling out due to a miscommunication. Not long after our intimate experience together, he had tried to contact me to hang out casually but I was indisposed and couldn't meet up. He took this as a slight, like I was blowing...

Massage Clinic for Men Pt. 02

by mastertosub on Sep 14, 2017
Gay Male

John turned partially on his side when Eric introduced himself. When he looked up at Eric he realized that the picture on Eric's website didn't really do the man complete justice. Eric was dressed in a form fitting t-shirt and a pair of silk Japanese pants similar in style to those worn by martial artists. Outlined in the thin material of Eric's pants John c...

Gay Bottom at College (Now Public)

by meris on Feb 1, 2016
Gay

My name is Sam tomorrow is my first day at college I'm 18 and have been gay for a while. I wake in the morning and get out of bed feeling very awake and excited I look at myself in the mirror wild brown hair looking frizzy from my shower the night before yet still looking cute. My emerald green eyes stare back at me hungrily, popping noticeably from my almos...

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Anal Sex Ch. 04

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

I have been doing this anal sex, since 1985 but the best anal sex I did was in 1997 with a very cute young teenage boy of about 19 years of age. He became my friend while I was coming to my hometown by air from some other city. He was a very shy person and never had any sexual experience except playing with him self. Since we had become good friends, so we w...

Vacation Sex Ch. 05

by Olive Hizklosoff on Sep 15, 2017
Gay Male

My wife went out to California to visit her cousin for four days. I know that she had an ulterior motive for visiting her cousin. She wanted to "run into" the woman we met while we were on vacation. My wife had hit it off with Sonny immediately. Their rapport was as if they had been friends all their lives. Although they had never met before and my wife had...

Quarantine: Day 1

by Gingermedic on Mar 30, 2020
Gay Male

This is my first time writing a story. please let me know what you think! This was not how I expected to spend spring break, locked in my apartment with my roommate for 14 days. We were told we can't leave until the incubation period for this virus was over. I need to think positive to get through this, at least I have my roommate David. A little bit about...

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...

Special Procedure Ch. 02

by KenJames on Dec 24, 2017
Gay Male

It had been a long hard week for Steve. Literally hard. His wife Christie loved sex. They had two kids and were enthusiastically working on a third, but he couldn't stop thinking about the after-hours treatment Dr. Harry Wu had given him last Friday. He parked his car in the medical center lot and walked to the door, painfully aware of the gigantic bulge in...

Relieving after a Field Trip

by NicoDeviante on Oct 6, 2020
Gay Male

John was back from a field trip for his PhD thesis. It had been academically very productive, but also all work and no play, ten weeks without sex, John was desperate for cock. He had a debriefing with his thesis advisor and after that he went home and prepared thoroughly for sex, he wanted to be very clean and very sexy. The place to get all the sex he ne...