Gay Widower Stories

91 results
Orientation
Length
Source
Infinite Scroll

Travelling

by vinceh23 on Dec 3, 2017
Gay Male

I am a retired widower and have been taking road trips of a week or ten days through the west. This trip took me to Arizona and today I was in Scottsdale looking at a property I own there. I had checked the property and spent the night in a nice hotel and was having breakfast at a nearby coffee shop. I like to wear panties and bras and have gotten rather bo...

My Shy (but hung!) Grandaddy

by BottomBoyUK on Jul 16, 2019
Gay Male

After my first few experiences with David (see my other stories), I wanted to sample a bit of variety. I was regularly cruising online and chatted to a few guys but was quickly finding out that older guys who are versatile was a big turn off for me. I realised I was looking for selfish tops. Men who wanted to be sucked and who wanted to fuck. They wanted to...

Home for Seniors

by isoro1 on Apr 14, 2020
Gay Male

I'm a senior citizen, almost 70 years old. I'm also a widower, my wife of 45 years passed away little over a year ago. My kids are all grown and live in other areas of the country. The house was too big for me to take care of, so I decided to move into a senior's only living arrangement. Nice place, combination of apartments and small cottages. Even provides...

The Bookstore

by vinceh23 on Aug 30, 2017
Gay Male

We'd met bumping into each other at an adult bookstore. This was a store where not all the magazines were wrapped. I had been looking at a trannie mag and he'd been looking at the same mag and we put them back at the same time. We looked at each other and there was a spark of, what? Recognition? A recognition of similar tastes and desires? Yes, that's what i...

Don't Look Back Ch. 05

by ShelleyRunyon on Sep 14, 2017
Gay Male

Burnham, Texas wasn't much to look at, at least not from an outsider's perspective. It wasn't exactly located on the road to anywhere, and it held no locations of cultural or other kind of interest that might draw a tourist's attention. No gourmet restaurants, no museums. Not even a single famous grave. The entire population of the community hovered somewhe...

A Field Trip Encounter Pt. 01

by metro610 on Jul 30, 2019
Gay Male

On a school field trip a few years ago, I had an unexpected encounter with another dad which awakened a sexual desire in me I never knew existed. My daughter attended a small private school since the 4th grade when we moved to our home 5 years ago. Now in the 8th grade my daughter and I were preparing to participate in the schools' annual trek to Washington...

The Older Man Pt. 03

by t2u1ck on Mar 20, 2018
Gay Male

It's a while since I wrote about my meetings with Tom, a 50 something widower who shared my particular tastes in music but also got me so horny that I just wanted to spend more time with him. The trouble was that I was 25 and happily married to a beautiful woman! The last story finished up with a wonderful session of 69 at the culmination of which Tom swallo...

The Older Man Pt. 01

by t2u1ck on Aug 18, 2017
Gay Male

How is it that a normally straight lad starts to get the hots for older men. I think it started for me in my teens with some of my teachers at school. I was never particularly interested in my classmates but when it came to the teachers there were times when I couldn't take my eyes off them - even to the point that I wasn't listening to what they were saying...

Jay Taught Me

by dipperyslick on Oct 15, 2017
Gay Male

The day I really learned to fuck a love anus. I had made a couple of hookups, before meeting Jay, but they were mostly, cuddle, kiss, and blowjob sessions. If I was lucky, I might get a 69 out of it. So, Jay wasn't my first male sex encounter, but he sure was the most interesting. He was well educated and somewhat debonair. He had a soft approach to sex th...

A New Old Friend Ch. 01

by idsweaterguy on Sep 16, 2017
Gay Male

The cold late October wind had thoroughly chilled both Eric and Jeffrey as they finished their round of golf at the neighborhood course. It was only noon but both men were die-hard golfers and had no problem starting early. Jeffrey, a tall thin man in his early seventies with bright blue eyes who still retained a nice head of white hair, was a retired wido...