Gay Babysitter Stories

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The Good Old Boy

by carsonshepherd on Sep 25, 2017
Gay Male

“Sean, let’s go out. I’ve got a babysitter tonight and Tom’s working late.” “But Law&Order SVU’s on,” I protested, finishing my beer. The dark brown longneck bottle felt comforting in my hand. “You really need to get out of that basement, baby. Come on, we haven’t been out once since you got home, you can’t sit around feeling sorry for yourself forever.”...

My Dark Angel Ch. 05

by Prettyrock on Sep 14, 2017
Gay Male

"I'm going to kill that bastard! Who does he think he is? My father? I don't fucking need a babysitter! Where's Alex?" The guy hired to babysit me by the "king of assholes" himself, looked at me like I was crazy. Hell yes, I was! Crazily mad! I felt insulted! I was not two years old anymore! Even when I was eight, I knew how to take care of myself... But th...

Date Night Out with the Wife

by dixeenormous on Aug 30, 2017
Gay Male

My wife and I typically take one weekend night per month to get away from the kids and enjoy some grown-up time. On Friday night, Jules left the kids with our babysitter and met me downtown at my office. We were going to catch an early movie and then planned to grab a quick bite at a trendy Italian restaurant that our friends had been raving about. As we sa...

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...

Speech and Debate Pt. 06

by DAMackey on Sep 25, 2017
Gay Male

Through the Looking Glass: A Nerd in the Weight Room On a normal day, I would wake up by 7:00 AM to be out the door by 7:30 for first period bell at 8:05. I had my routine down to a strict science. 7 minute shower, 3 minutes dressing, 1 minute on hair, 4 to pack my bags and the rest at the kitchen table inhaling whatever was available before jumping in my C...

An Unexpected Love

by dreamcatcher549 on Sep 19, 2017
Gay Male

This story of course is complete fiction, to anyone out there that this resembles it is not intentional. Of course you should always practice safe sex, this is pure fantasy. As anyone else would when I look back on my life, I wonder was my life a full and happy one. Do you look at the glass is it half empty or half full. Mine was half empty until I met him...

Me - The Inconvenience

by Gay_sex_only on Sep 14, 2017
Gay Male

One Week Ago: I dropped my head, and let out a deep moan. There was a steady clapping as some guy fucked my ass on my bed. Doggy style was my favorite position at the time. We were both butt naked, sweaty as hell, and moaning like bitches in heat. It was fucking hot. "James!" I heard my mother shriek. I didn't even hear the doorknob turn. Now: Mom and...

Owned:Fantasy Becomes Reality

by silkstockingslover on Sep 14, 2017
Gay Male

Note 1: This story was written and is dedicated to a true wannabe faggot-cuckold Dave. Note 2: A special thanks goes to Estragon for his copy editing work. 1. THE BEGINNING I blame Literotica. No seriously...if it wasn't for Literotica, none of this would have happened. Now in all fairness, some would argue it is my fault; as it was my own stupidity a...

My First Time

by andreaplays on Aug 18, 2017
Gay Male

I have always like dressing in woman's clothes since being a child. I often would dress up when my parents would leave the house and I would parade around like a woman would. Now that I'm 33 years old and married, I have to wait until my wife leaves to dress up as she wouldn't understand. I often like to dress with the clothing that I like fucking my woman...

The Effects of Drunken Driving

by bi_indiana_chub on Aug 18, 2017
Gay Male

"Ma'am, can you step out of the vehicle." My wife looked at him with what I'm sure was the most drunken look he had ever seen, but I might be wrong. We hadn't been going that fast and I was pretty sure that we had been staying between the lines, but being half drunk myself, I didn't help. She turned to me and even with the drunken stupor, anger was written a...