Gay Chubby Boy Stories

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Taking the Neighbor Ch. 07

by jjdtx on Oct 30, 2017
Gay Male

***Mom gets more interested in Allen's gay side... For the next two weeks, things had been going about the same way. Daily, I was able to fuck Allen in his tight little ass, and we were sucking each other every chance we had. Allen was getting better and better at taking large dildos in this ass too, something that he quite enjoyed. He had his girlfriend...

Finally Caught Up with Me Ch. 02

by felizfun on Oct 12, 2020
Gay Male

Editor's note: this story will make the most sense when read after "Finally Caught Up With Me" Randy wasted no time making good on his threat of blackmail. My phone buzzed me awake the very next Sunday morning. It was a text from a number I did not know, but soon deduced was Randy's. "You need to be at my place at 11am. Plan to be here for 2 hours." I wa...

Pile of Mattresses

by Boxlicker101 on Aug 18, 2017
Gay Male

It was the summer of 1975 and Curtis Holt was not happy to be doing a sixty-day sentence in the county jail for possession of marijuana, although he knew things could be worse. For one thing, he was aware there were plenty of men doing far longer stretches, and they would have gotten extremely horny, which should have greatly interested him. For another, he...

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...

Jared Ch. 01

by andrew1990 on Sep 1, 2017
Gay Male

Water splashes over his face; he stares into the mirror. For 5 minutes he stares wondering how he got there, only hours before he was sitting at home wishing he was in this position, but now it's here he isn't so sure. He looks at his 'cute face' and brushes his brown hair to one side of his forehead. He adjusts his glasses getting ready to go back to his ho...

Gettysburgh Alone

by whoisboss on Aug 18, 2017
Gay Male

I was vacationing alone in Gettysburg Pa. I am 34 and unhappily married. At 6 foot and 210 lbs. I can find women but I have been curious. I decided to stop at 8 p.m. At the local cigar shop just as it was closing. I talked to the older men who work there he was about 60 and I was about 35 at the time. He was over 6 foot and thin. He had a beard and a mean l...

Drive Ch. 01

by DiMarino on Aug 17, 2017
Gay Male

"Drive you home, Chris?" The young blond stopped at the door and looked back at his night's employer. The eighteen-year-old's pulse began racing. He'd thought the older man wasn't going to. "Sure, Mr. Mathers." Another week. Another babysitting job at Mathers' home. Another drive. Chris lived an eight-minute walk from Mathers' house. Somehow, Mathers' wif...

Used in the Bathroom

by chubby_biguy88 on Sep 14, 2017
Gay Male

Nate sat in his car and took another long drag off of the half-finished cigarette, he knew that if he was going to chicken out he had to do it quickly. He looked again at the plastic shopping bag in the passengers seat and was tempted to reach inside and feel the cotton panties again. "Pink." The message had said, and Nate did not want to disappoint the st...

The first time saying I love you

by summerlove91 on Apr 1, 2020
Gay Male

Dan and I had been seeing each other for a few months and during my second semester of my sophomore year in college, and I frequented him on Tuesday's at his apartment during my lunch breaks because that was the day I had a 3 hour break in my class schedule. On Tuesday's where I'd know I would see him, I would wake up extra early to get ready. I would even e...

Derek Pt. 03

by TAHammer on Apr 27, 2020
Gay Male

Everybody was decked out in cowboy boots, jeans, and bandannas at the afternoon barbecue. Of course, Derek with his sleeveless button-up shirt, tight jeans (with a big buckle belt), and cowboy boots looked like the Playgirl cover model for the cowboys issue. Everyone watched him swagger around the patio. Karen gave him a cowboy hat, and every gay guy and str...