Gay Gay Chubby Stories

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Caught with a Wedgie

by marriedhubbi on Oct 8, 2019
Gay Male

I never knew that my straight-laced life could take such a turn. Until that day I thought my hidden life of masturbation would remain undiscovered forever. You see, I have an unusual way of masturbating. When my wife and kids are out of the house, I often head to the bedroom and strip to my underwear. I prop up a couple of pillows in the middle of the bed,...

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...

All Potatoes and No Meat

by timmywells on Aug 28, 2017
Gay Male

"I could be like those folks that stand on the side of the road during them marathon races," Red Foster quipped as he watched the plump kid guzzle the bottle of water he had just been given. "Got plenty of time on my hands since I retired." The jogger, who the little old man knew only as Bobby, had lived down the road for years and until recently had been a...

Golf and Suck Buddy

by 40yrman on Sep 14, 2017
Gay Male

I was cruising an internet gay site, when I came across a profile of a married older man that was looking for some discreet sex. He was also looking for a golf partner. This was an interesting way to meet and play! At least it would make for interesting side bets! I e-mailed him to meet me at a local golf course that usually didn't have a lot of morning golf...

Nephew's Readjustment Pt. 17

by bart_allen on Sep 14, 2017
Gay Male

This story contains femdom, gay conversion, extreme humiliation, BDSM aspects, and frankly, is fairly extreme. If you enjoy it, please check out Power Trip, by wally_west, who inspired this story. ***** The next week went slower. He was studying for his final set of exams, and Cynthia didn't want to interfere too much with that. Not that she had to. One lo...

Gay Under The Table

by merichane on Aug 18, 2017
Gay Male

I still remember the first time I replied to a gay personals ad online. I was only 18, in the first month of university in a new city away from everyone I had ever known. Hung looking for younger gay 37yo bwm, masculine, drug and disease free Looking for someone who likes kissing, sucking, maybe fucking. I sent him my stats and a face shot taking at an...

From Straight Virgin to Gay Bitch

by sissyboi on Dec 24, 2019
Gay Male

I was 18 when I lost my cherry. Not in the normal way, not in the boy meets girl kind of way. That didn't happen until I was 22, and was a total let down compared to my real first. His name was Scott, he was tall, dark and had a tight firm body. My first girl was chubby and drunk and I didn't quite catch her name. Still before I met Scott I was very straight...

Secret Life of Chub Ch. 02

by BBB771 on Sep 15, 2017
Gay Male

"Talking It Over But Attraction Wins" On a humid summer night, Ben awoke with a wet feeling all over him. He thought he pissed in the bed, so he lifted the sheets and placed his fingers down his red briefs. He lifted his wet fingers to his nostrils and smelled. The odor was salty, and he realized he had a wet dream moments ago. Then he licked his fingers, t...

Massage First time Man to Man

by bidavy on Jul 30, 2019
Gay Male

I found him in the classifieds, this was in the late 90's, long before internet and the kind information I was looking for was hard to come by for a naive but sexually charged 22 year. I was so nervous, I almost didn't get to the door. Once inside his townhouse he told me about his massage therapy rates, there were 3 styles of massages he offered and the thi...

My First Taste

by MrE352 on Sep 14, 2017
Gay Male

They say you never forget your first time. Although it's been nearly 20 years, I can still remember it well. It was January of 99 and I had just turned 18. My parents went out of town to celebrate their anniversary for the weekend, and that meant one thing for me. Busting as many nuts as I could. I called my girlfriend at the time to try and make plans. L...