The Babysitter
by Avery Sam
Copyright Information
The Babysitter
by Avery Sam
Ā© 2026 Avery Sam
All rights reserved.
Author: Avery Sam
Contact details: averysam.parachute371@passinbox.com
Book cover, illustration: Avery Sam
Editing, proofreading: Avery Sam
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Table of Contents
Kool-Aid
Guys rarely ask one another about how they lost their virginity, but women are always very curious about it.
I remember the night when my girlfriend Amy, who is now my wife, asked me.
I thought about telling her the truth, but then I figured it was safer to just skip ahead to the story about awkwardly fumbling around in the back seat of my parentsā car with Karen Allister on prom night. First, it was a true story, and second, Iād already given Amy a brief sketch of all my ex-girlfriends.
We both had a laugh, and that was it. We never discussed the matter ever again.
But lately, the real story has been on my mind.
It all started when my parentsā business was just taking off. My dad was frequently out of town in those days, trying to get new investors, and my mom was always going out to dinner meetings to try and woo clients. As such, I spent quite a few nights at home alone with babysitters.
Most of the time, nothing particularly remarkable happened. Some sullen-faced teenage girl, or occasionally a freshman in college, would come over. Theyād exchange a few words with my mother. My mother would force me to say hello. Then, once it was just the two of us, Iād go to my room and play video games while the baby sitter sat in the living room and watched TV.
Frankly, the whole thing was embarrassing as hell, but my mom insisted on it because of my medical situation, which sometimes caused me to pass out without warning, a condition that first began after I was in the car accident that killed my father.
My bedroom had wall-to-wall carpeting so I wouldnāt bump my head if I suddenly lost consciousness, so Iām really not sure what the point of having a babysitter even was, especially when most of my episodes usually only lasted a minute or two.
Nonetheless, my mom insisted, and so I had to go through the whole humiliating ritual of standing there while she explained to some stranger all of my personal details, a girl who didnāt give a shit about me and was only there to make easy money while eating our food and talking to her boyfriend on the phone.
So yeah, that was the situation when Lisa appeared at our house one night. About the only thing that made me pay any attention to her at all was that she had very intriguing green eyes and was wearing a belly shirt.
Of course, these days, it's commonplace for girls to go around wearing all kinds of skimpy outfits, but back then, the fact that I could see an inch or two of bare midriff on her was pretty spicy stuff.
Even so, five minutes after my mom left, things were going normally. Lisa plopped down on the living room sofa, and I headed ...