Gay Babysitting Stories

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Babysitting for the Ulichny's

by Abrennan on Jul 8, 2018
Gay

* Hey everyone, this is a long WIP, and i'm willing to let people contribute, feel free to add or write a chapter, and if the quality is good, it will stay.* The Ulichny's had always been good clients. Their three kids were well behaved, quiet and always seemed to be ready for bed. Babysitting for them was always fun because it usually meant plenty of free t...

Dave and Leroy Ch. 07

by kmillerk1 on Sep 25, 2017
Gay Male

Chapter 7 - Babysitting for Allison and Mikey's Birthday Party The day finally came, when Terry and Shane were able to return to their house. All the repairs were done, and they pretty much had a brand new home. Dave and Leroy celebrated by having sex all night in the family room after Dave came in from work. An hour after their last session that morning,...

The Internet Submissive

by Indianaboy6555 on Apr 9, 2019
Gay Male

It was a typical Saturday at work for me. I was basically babysitting a computer all day, so I had a lot of time on my hands. Actually, probably too much time in reality. So naturally, since I had my computer there, I put it to good use. I pulled up a website, and started looking for a good submissive plaything. My Dom side was out in full force that day,...

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...

Little Girl Ch. 01

by gotholympians on Aug 18, 2017
Gay Male

Mr. Berkley checked his rear-view mirror and backed his Beamer out of his driveway onto the two-lane highway. His Rolex-laden wrist lifted so he could adjust the mirror a tad, then he ran his fingers through his silver hair. An aging man of expensive metals, he was. I sat in the passenger seat, my hands in my lap holding the twenty dollars I had gotten for w...

Life Interrupts

by rondick310 on Oct 29, 2018
Gay Male

It's hard to get old and even harder when you have grown-up responsibilities. While my bi-lover and I frequently lament "if we only knew then what we know now" we are old enough to know that life is imperfect, and you must take what you can, when you can. Just the other day, he texted me about my recovering wife (she had some back surgery that was rushed be...

It's Not Gay, It's Just Sex

by datura48 on Sep 25, 2017
Gay Male

As he pressed his cock into me, I wondered what had happened to me. I had never had the urge to take a cock up my ass, yet for the third time in as many weeks, I was bent over getting dicked by my brother-in-law, Jeff, and enjoying it. And this followed months of sucking each other off. I consider myself straight and happily married. From talking to friends...

My Married Friend's Son

by DavidPatrick on Sep 19, 2017
Gay Male

(Part One) I had known "Trick" (short for Patrick) since his third day. I was with Rob when he got the news that the water surrounding his second child, and first son, had broken, and I visited them all in the hospital 72 hours later. I babysat Trick and his older sister, "Sonny" (short for Jackson), regularly while he was a toddler. Trick was often in a C...

The Cocksucker Chronicles

by sterculius on Aug 31, 2017
Gay Male

What had started out in high school as youthful sexual experimentation with my best friend Larry, quickly turned into an obsessive need for me to be on my knees sucking on his very big cock in order to get him to cum in my mouth. I had happily become a full fledged cocksucker and I eagerly blew him at every opportunity until he went off to college. After h...

What a Headche!

by SumOfAllThings on Aug 18, 2017
Gay Male

"Hey sweetheart," A voice practically screamed a few feet behind him. Alex turned around, an angry retort on his lips when he saw who was tailing him. He swallowed what he was about to say and hurried towards the park gates. A young man, a couple of inches taller than Alex's 5"10 frame fell into step beside him and draped a well muscled arm possessively over...