Gay Older Woman Stories

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Initiated by an Older Man

by honestWithWifie on Jun 9, 2020
Gay Male

I am a 60 year old male and this is my true coming of age story. This may not be jerk off material. It happened ... This was the seventies. I had just turned eighteen and was still living at home with my parents. We were living in suburbia on the outskirts of New Orleans. New Orleans is famous for the French Quarter and the gays who live there. I was young...

Caribbean Cruise Ch. 02: Chet Gets Laid

by sr71plt on Sep 14, 2017
Gay Male

At first Chet thought the older man staring at him from across the bar at the top of the cruise ship was Jamaican. The man engaged his attention because he had the most compelling light-gray eyes, which went really well with his silver-gray hair and the black suit with black silky shirt and black tie with a hash pattern of silver strands. But the thought tha...

Summer of '59 Ch. 03

by walterio on Sep 14, 2017
Gay Male

INTRODUCTION It would help to read chapter one to meet the characters but it is not necessary. Cliff had his first experience in chapter one with an older woman but things got a little too kinky for his liking. However that encounter with a woman twice his age changed the way he looked at older women and he had his sights set on his neighbor's mother. In ch...

Just a Number?

by NRMathis on May 9, 2018
Gay Male

Couples with large age gaps have some sort of assumptions that are automatic whenever people look at them or think about them. If it's a young man and an older woman, she's a cougar. If its an older man with a younger woman, she's a gold digger and he's her sugar daddy. If it's two gay men people assume a sissy-boy/daddy relationship. With lesbians, I have n...

To Live and Fuck in L.A. Ch. 02

by Fit_for_a_Fuck on Jul 11, 2018
Gay Male

The next morning Mr. Castle had a car pick Nicky up at his apartment and drive him to the tanning salon in Beverly Hills. When he arrived, he walked up to the front desk where a very attractive older woman with brunette hair in a ponytail and big tits was sitting. "Hi, my name's Nicky," he said. "Mr. Castle sent me here." "Ah, yes," she said with a sligh...

It Started as a Favor to His Wife

by vikkihawe000 on Jul 6, 2020
Gay Male

All through med school, Devon Daniels knew he wanted to be a fertility specialist. An older woman, considered to be the top specialist in the country, gave a lecture at a conference he happened to attend and he was hooked. She talked about how she was able to help people in dire straits. She talked about how it was problem solving unlike anything else in med...

First Bi-Guy Experience Ch. 03

by Resparvae on Jul 15, 2020
Gay Male

If you think you might enjoy this real life effort from me could I suggest that you read my first two real life submissions? In my first Literotica effort I wrote about an affair with an older woman, Muriel. From day one I have had a thing for older women, my first being when I was 17 with a firecracker hot 46 year old neighbor that I had known since I was e...

Accept My Apology

by LoveIsUniversal on Sep 1, 2017
Gay Male

Lazlo wanted a fun weekend, and his wish had been granted. He chose a city on the California coast for nothing other than to find a woman and share the fun behind closed doors. Manhattan Beach, which stood just a few miles south of Los Angeles International Airport (or more commonly known as LAX) became a city that he looked forward to visit the most. And on...

On the Job Training

by dixeenormous on Sep 19, 2017
Gay Male

Everybody's got a first time story. Being a 33 year old divorced guy, I thought all my firsts were long gone. You know, my first blowjob, my first fuck, my first older woman, my first three-way; I'd had some good times but I figured the rest of my sex life would be pretty run of the mill. On the downhill slide you could say. That is until I decided to becom...

Fixing a Flat

by buttcheeks777 on Sep 14, 2017
Gay Male

The day started out in the upper-70s and the temperature hasn't even started to rise yet. It's going to be a very hot day, in more way than one. My wife's sister married a manly-man, a former hockey player and party boy. A day laborer named Chuck. He's never held a job for long and he seems to do the same thing with women. He was caught cheating on my wife...