Gay Widower Stories

91 results
Orientation
Length
Source
Infinite Scroll

Angry Old Man

by Cicero6 on Aug 18, 2017
Gay Male

This short story is an abridged depiction of an experience that still leaves me baffled. My wife and I bought a home from an eighty-something widower four years ago. Victor seemed nice enough in spite of the fact that he was selling the home he and his wife had built in the mid-fifties. All was going well with the inspection and closing until a discrepancy i...

My New Older Friend

by BilyumQ on Aug 18, 2017
Gay Male

I've always had an affinity for older men, but these days it seems I'm either the older man or one of the older men involved when there's sex play. But recently I was fortunate to meet a man who at seventy-one made for the widest margin in age I'd been with in quite a while. John and I met at a rehearsal for a school function in which my granddaughter and...

Icebreaker

by CenCalBiGuy on Dec 24, 2017
Gay Male

Normally I hate these ice-breaker activities, especially at professional conference, but with this table-mate I was willing to give it a try. It wasn't an accident that I sat here. He has average looks but is fit and trim. He looks to be in his late forties or early fifties and takes very good care of himself. His polo shirt is snug around his shoulders and...

Never Too Late

by alexcarr on Aug 18, 2017
Gay Male

I recently moved to a sheltered home scheme renting through a local Housing Association. That's where I met Gordon, a widower with a heart by- pass which he said made him a little bit immobile. I got to know him doing my bit in the community garden, he would come and sit on the garden swing chair as I tended the garden. In between times I would take a seat...

Buying a Truck

by metro610 on Jul 30, 2019
Gay Male

Last weekend, I stopped at a local Ford dealership to look at their line of 2019 Ford 150's. I am nearing the end of a car lease and wanted to explore my options before getting another vehicle. As I walked into the showroom, I was approached by John, a 27-year-old good-looking salesman. He had a pleasant smile and greeted me with a firm handshake as he loo...

Block Party

by Triplebottom on Oct 8, 2018
Gay Male

I'm a successful young banker that recently bought his first home on the corner of the street. The neighbors were all friendly and decided to throw a party since I was the new guy that moved in. The block party was a success. There was good food, good music, and everyone seemed to have a great time. I was pretty buzzed when Rob, he lived 2 houses down, asked...

The Good Neighbor

by Monterock on Aug 30, 2017
Gay Male

Maria and I had bought our dream home after many years of sacrifice. This goal had become all consuming and had taken its toll on our lives. Due to the long work hours and conflicting schedules we had seen little of each other over the past several months. Maria is a legal secretary she works the typical 9 -- 5 and often later. I drive taxi and I try to tak...

Candy

by siktici on Sep 14, 2017
Gay Male

I didn't want to be a cowboy, but I certainly wanted one to fuck me. So, to honor those sojourners of the dusty trails I wrote this. When settlers in the 1870's first used "dude," to refer to pasty-faced Easterners coming to The Rockies, they took notice of men with a distinguishable lilt (I have no doubt), of men with a different spring in their step, of m...

The Older Man Pt. 05

by t2u1ck on Apr 1, 2020
Gay Male

It's some time since I wrote the stories about my affair with a much older man. I'm married and in my twenties and Tom is a widower in his 50s. I had not recognised that I was bisexual until I met Tom but since we first got together I have enjoyed the delights of oral and anal sex and shared a fetish for briefs, especially with shirts tucked in them. We also...

Top Becomes a Daddy Bear's Boy

by DaddyBearChaser on Jul 6, 2020
Gay Male

Uncle Bob had taken me out fishing again, it was a beautiful summer day, a perfect day to be out on the lake. I always enjoyed spending time with him when the opportunity arose. My Uncle was a rugged, mid 40's, 5'10, 250 plus pound, hairy brute of a man. I loved checking him out when he wasn't looking, maybe too much. It's just that when his shirt was off,...