When I was a teen I lived in a very small town. My parents were quite well known and had many friends, and soon I was enlisted as pretty much the town's only babysitter, albeit I don't know how more than a few couples went partying on a given night when I babysat for only one of them, but whatever; maybe there were more sitters than just me?
In any case, I had several regulars, including the Lowells, with a five-year-old girl, three-year-old boy, and, later, a baby girl; then there were the Ramseys, who had a baby girl; an older couple, the Sykeses, had a four-year-old boy and yet another baby girl (yes, I took care of a lot of infants, including diapers and the works!); while the Kirbys had a brood of several girls: two, four, and about six; finally, the Waynes' kids were a boy, nine, and a girl, eleven (both not a lot younger than me at the time!).
Since they were relatives, I started with the Lowells, but as far as I recall, nothing much happened the first few times I sat for them; at the time I didn't have a girlfriend, either. However, at the Sykes' place I began my education.
They had a stash of porn – several, in fact – that I found under the sink in the bathroom and in a linen closet in the hall (in their bedroom, too, but I wasn't brave enough to go in there, yet). Let me first say that Mrs. Sykes was fucking fine; long blonde hair and fairly petite, but with curves that would straighten Lombard Street. Naturally I fantasized about her, especially since she dressed in extremely risqué outfits for the size of our town: daring yellow miniskirts and low-cut blouses that I'm certain illustrated at least size D for me quite well, although of course I had no clue at the time.
I now know that they were probably going out to swinger parties; my first hint should have been the books I found under the sink – trashy pulp novels – portraying B&D with gangbangs and orgies. Naturally this was the first time I had imagined such a thing, let alone read about it, so you can imagine how I felt after poring through this stuff. I vividly recall one scene in particular, where a woman was tied up in a rope swing and gangbanged by five guys; I can almost still read the words regarding how she felt about having, "a cock in her pussy, one in her ass, one in her mouth, and one for each hand". Fuck!
Later, I also found their stash of dirty mags in the closet, and was busily perusing these one night when I heard noises from the bathroom. I got up to find their son (of three-or-four, you'll recall) in his jammies with almost the entire contents of his sexy mother's makeup drawers scattered all about, happily painting his face with her bright red lipstick. I'm sure I made some exclamation, and then found towels or something to clean him up before sending him back to bed. He'd inked up his jammies as well, though, so I found a clean pair and changed him. Interestingly, his little pecker was circumcised, and I'd never seen such a thing – but I refrained from checking it closer (even though I could have, but that would come later). The kid was talking by then, but wasn't very intelligible – to me – because he said something about, "zezzy plays", which I didn't understand.
I then tried to tidy up the bathroom, but it was hopeless; compacts and eyeliners and myriad esoteric stuff (to a 13-year-old boy) were mangled and smeared everywhere – counters, mirror, walls... Anyway, I tried to clean up that mess too, but didn't do a very good job, I'm sure; and I left all the makeup, because I hadn't the faintest idea what was what and what was salvageable.
I confessed on the way home with Mr. Sykes what had happened. He didn't say much this time, but I guess I needn't have been worried that they wouldn't hire me anymore and their stashes were lost to me forever, because next time, on the way to his place, he gave me a stern lecture about keeping an eye out, as I was supposed to do, and not get distracted, "reading comics."
"Not comics, I was reading your mag—" I immediately regretted my further confession, but, as it turned, should not have. I'm sure I blushed to my toenails, but was also too embarrassed to look at Mr. Sykes; I wish now I had seen what he may have been thinking.
In any event, I went in to find Mrs. looking hot as ever, and all thoughts of guilt over the 'accident' fled, as I checked her out again; it appeared she had replenished her makeup supply, and once more applied it to heart-stopping effect. They left, and much to my delight, they hadn't moved their stashes. Still, I felt too guilty and nervous that they might come back and catch me, though I couldn't say whether I was more worried about being caught looking at porn or not looking after their son. Both, I suppose.
The next (memorable) time with the Sykeses would have to wait, though, because I got my first sexual experience some time later, at the Lowells'.
I should tell you a couple things before getting there, though. For one, this may have been the first time I'd found and read dirty magazines – I don't remember the exact order of events – but I found others, including my dad's stash and some in a dilapidated cabin my friends and I used as a 'fort', as well as a huge pile that were tossed into the dumpster by the hotel I worked for as a busboy/dishwasher (I realize now they were unsold; the covers were torn off to be returned for credit). I didn't care that they had no covers; the interior – articles, of course – were far more titillating. Anyway, I hid a number of the more explicit ones, and brought a few softcores back home, and actually presented them to my dad (I knew he had similar ones, but not the full extent of his collection). He kind of smiled at my mother, who looked at me strangely, and took them, neither said anything then.
The second thing I need to tell you is that, odd as it may seem for a pubescent boy, I still did not know how to masturbate. I would soon get a lesson from a most unlikely source, however.