Gay Timmywells Stories

156 results
Orientation
Length
Source
Infinite Scroll

Did We Wake You?

by timmywells on Jul 17, 2018
Gay Male

Prior to our chance meeting very late one night in the hallway of our house, most of the times I had seen Mom's boyfriend were from waves we exchanged while he was in his car picking up or dropping my mother off on the several times they had gone out together. We had been introduced by my mother as well. With me starting college and working part time I wasn'...

Grandma's Got a Boyfriend Ch. 04

by timmywells on Sep 14, 2017
Gay Male

This is the conclusion of the story. I apologize for the delay because I thought I had submitted this before taking some time off from writing, but apparently I hadn't. Thanks for your patience and thanks for the folks who wrote and asked about where the end was, which brought my screw up to my attention.. *** Jeremy was wrapped around his Grandma's boyfr...

Bobby's First Suit

by timmywells on Aug 18, 2017
Gay Male

"I thought it would be a good idea to buy Bobby a suit," Gladys Bradley told the little Italian tailor whose shop was down the road from their apartment. "Not only for the dance, but with Bobby going to college in a couple of months he'll probably need a suit for other things." "A college boy now huh?" Tony Caruso asked as he rubbed the dense 5 o'clock shad...

Uncle Ed

by timmywells on Aug 18, 2017
Gay Male

Reader alert... This story contains sexual situations between an uncle and a nephew... ************** July 14, 1970 was the greatest day of my life, which at that point consisted of 18 years and two months. Even now, more than 40 years later, it still ranks as one of the handful of days that I remember most of all, and to think it almost didn't happen. I...

Crestwood Motel - Room 119

by timmywells on Aug 17, 2017
Gay Male

I turned off the shower and stood there for a long moment, trying to get myself to calm down. I was nervous and excited, somehow managing to both dread and look forward to what awaited me when I came out from behind the shower curtain, or should I say who was waiting for me. Mr. Fields. Mr. Roger Field, to be exact, and from what he had told me over the cou...

Fortress of Solitude

by timmywells on Aug 18, 2017
Gay Male

In the Summer of 1970... Charlie was heading off to college out west, while I was going to school nearer my home, and when we met on the day before he was flying out, I was filled with mixed emotions. I had known Charlie since kindergarten, and we had been best friends all of those years, sharing laughter and tears as we grew up. Now we were parting, and e...

Like the Old Days at the Barber's

by timmywells on Aug 18, 2017
Gay Male

In the very early 1970's long hair was in for guys, and in an effort to fit in with the rest of the guys I let my hair grow as well although it was not nearly as long as many of my peers. Even my barely shoulder length dirty blonde hair was too long for my Mom, who in an effort to make up for the father who was no longer around was doing her best to wear bo...

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...

Grandma's Got a Boyfriend Ch. 02

by timmywells on Sep 14, 2017
Gay Male

The next day at Grandma's house, Jeremy offers to show Ted where the apple tree way out back is. *** "This is far enough," Ted informed me after we got far enough away from the house. "You did good." "What are you doing?" "Getting comfortable," Ted informed me as he put out the blanket he had snuck out of the house and began to unbutton his shirt. "Take...

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...