Gay Grandpa Gay Stories

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Grandpa's Gay Christmas

by jmnov27 on Dec 23, 2019
Gay Male

Well, it was bound to happen sooner or later. My wife and I have been married for 46 years. Before we were married, I had rare opportunities to have sex with men. Less than five times from the age of about 16 had I enjoyed the look and feel of a naked man lying next to me. I seemed to have more luck with the ladies, but being shy, it made heterosexual relati...

Grandpa's Man Cave

by timmywells on Sep 14, 2017
Gay Male

For Glenn Saunders, the summer of 1979 promised to be pure hell. While his friends were enjoying the time after graduating high school doing things that 18 year old kids do before entering college or going on with life, Glenn was stuck out in the middle of nowhere. His parents were spending the summer in Europe, and while Glenn could have joined them, he ch...

Grandpa's Toy

by timmywells on Apr 3, 2019
Gay Male

Please note that while the subject matter is gay the people are related. *************** "I'm sorry," I said sheepishly when I noticed that my grandfather was standing in the doorway of Grandma's old sewing room, which had turned into a computer room after her arthritis made that hobby too uncomfortable. "Not nice to snoop around, Andy," my grandfather sa...

Grandpa's Summer Visit

by timmywells on Apr 3, 2019
Gay Male

I knew that my grandfather was going to visit us, so I wasn't shocked when I saw him that Thursday afternoon in the guest room. It was the way I saw him that set me back a bit. I walked down the hall that afternoon, and when I passed the bathroom I could tell that someone had gotten out of the shower recently. That someone was my grandfather, and while it w...

Grandpa's Surprise Visit

by timmywells on Apr 3, 2019
Gay Male

This story takes place in a sleepy town in upstate New York. ***** Chapter One: Busted. It was the most embarrassing moment of my life; and that's saying something when I think back at the many humiliations I suffered through as a teenager. When having your own mother catch her boyfriend in the midst of taking you anally comes in second, the winner must b...

Caught By Grandpa

by timmywells on Sep 14, 2017
Gay Male

Day one of my summer long visit to my grandparents farm had certainly been an interesting one, I thought to myself as I prepared for what I expected to be at best a fitful night's sleep. It was amusing in a way to think that while I had managed to keep a very personal secret from my folks for 18 years, a few hours up here and I was exposed. I had made a fri...

Exiled To Grandpa's Farm

by timmywells on Sep 14, 2017
Gay Male

The summer of 1969 hadn't turned out quite the way Lloyd Carmody had hoped. Expecting to goof off until college started in the fall, Lloyd got a shock when his parents told him that he would be going to spend the last two weeks of July at his grandparent's farm. "You haven't bothered to get a job, so it isn't like you have any responsibilities around here,"...

Bill's Sexy Straight Grandson

by javierp25 on Aug 18, 2017
Gay Male

Mike always took time to visit his grandpa at the retirement community. He owed that to the guy who had been a father to him after his own dad left when he was a toddler. Bill had been a tough with Mike, but strong hand had made Mike the successful young man that he is. At six foot two, two hundred and twenty pounds his beefy muscular body and gorgeous bla...

Grandma's Got a Boyfriend Ch. 01

by timmywells on Sep 14, 2017
Gay Male

This story ran a little long so I've broken it up into parts. *** This was a whole new experience in this summer of 1993, because while I had been sent to spend the summer with my Grandma every year since Grandpa died four years ago, things had changed around the old farmhouse. Grandma had a boyfriend, and I know that the term sounds funny when you atta...

The Lawn Rangers Ch. 08

by texaswade on Sep 14, 2017
Gay Male

I opened my eyes and looked around, confused as to where I was. A sharp pain in my ass reminded me that I was at my grandpa's cabin with my best friend John. He had just fucked my ass with his big eight inch dick – twice. We had arrived at the cabin on Friday in the early afternoon. It was apparently getting dark already. John was laying next to me, snorin...