The Babysitter

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 parents’ car with Karen Allister on prom night. First, it was a true story, and second, I’d 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 parents’ 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. They’d exchange a few words with my mother. My mother would force me to say hello. Then, once it was just the two of us, I’d 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 wouldn’t bump my head if I suddenly lost consciousness, so I’m 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 didn’t 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 into my room to play some Super Mario Brothers or Sonic or one of the other games everybody now considers to be classics.

Sure, I was probably a little more stimulated than usual on account of Lisa’s belly shirt, but so what? I was a very horny teenager back then, sporting erections pretty much all the time. A stiff breeze could give me a boner in those days.

Anyway, the moment everything changed was when I got up to go to the bathroom. I walked down the hall, did my business, and was just about to re-enter my room to start a new game when I caught a brief glimpse of Lisa in the living room. And the thing that caught my eye was that it appeared like she was naked.

What?

I assumed I was just hallucinating things, the after-effect of staring at the screen too long plus my overacting hormones. But of course, I needed to double-check, so I cautiously inched my way into the living room.

Lisa was in the kitchen by that point, but my jaw just about hit the floor when I verified that she was, indeed, completely naked. And when I say naked, I mean she didn’t have a stitch of clothing on, no pants, no shirt, not even shoes or socks.

“Hey there,” said Lisa, giving me a big grin when she noticed my presence. “You thirsty? I was just thinking about making up a batch of Kool-Aid.”

“Uh...” I said, probably with drool dribbling down my chin.

Seriously, my brain just could not compute what I was seeing. Now only was there a good-looking young woman in my house who was totally nude, but she was acting completely nonchalant, as if this was all perfectly normal instead of it being the greatest erotic manifestations my febrile teenage mind had ever beheld.

“I’ll take that as a yes,” she said with a casual laugh.

All I could do was stand there and stare as she reached up to get the sugar down from the cabinet, a movement which gave me a clear look at her bare behind.

Remember, this was before we had the internet at home, so I’d never even seen a naked woman before. The closest I’d gotten was a few cheeky pictures in the lingerie section of a clothing catalog, and this was easily a million, billion times hotter.

“Wow, Cherry, huh?” said Lisa, examining the canister of Kool-Aid. “You guys like to keep it old-school. Nice.”

I might’ve grunted something by way of reply, but I don’t remember. My brain was just overclocked at that point, too busy trying to record everything for later enjoyment to waste any neurons on trying to maintain a conversation.

It was only when she had finished making the Kool-Aid, poured herself a glass, walked over to the sofa, and then sat down that I finally snapped out of my trance.

I’d always enjoyed studying the subtle sway of girls’ tits underneath their clothing, but seeing Lisa’s boobs bounce around unfettered like that took my arousal to a whole new level. I’d never imagined that it would be such a fascinating sight to watch.

“Go ahead,” said Lisa, making a little gesturing movement with her head. “Pour yourself a glass if you want.”

“Uh, okay,” I somehow managed to say, stumbling my way into the kitchen in a complete stupor.

Something about holding that glass in my hand helped stabilize me a bit, perhaps because it was my favorite one. It was made of red plastic and had a kind of pebbly exterior to it. It was very similar to the ones they used to have at Pizza Hut, which is why I liked it.

That cup grounded me enough that I was able to walk back into the living room without dropping it and making an even bigger fool of myself.

“Your name’s Benjy, right?” said Lisa, patting the sofa cushion beside her. “Come on and have a seat. Don’t worry. I won’t bite.”

“Um, okay,” I said, so focused on not spilling Kool-Aid down the front of my shirt that I completely forgot about the raging erection making a giant bulge in the front of my jeans.

“I bet you’re wondering why I’m not wearing any clothes,” said Lisa with a little laugh. “It’s because I believe in something called naturalism. Have you ever heard of that?”

“Mm-mm,” I said, using all of my willpower to force myself not to stare at her boobs.

“It's from a book. I’ve got a spare copy in my purse that I’ll give you,” said Lisa. “But the theory is that our bodies are spheres of energy, and anything that restricts that energy can cause sickness or unbalance us.”

“Uh-huh,” I said, gulping down a generous amount of Kool-Aid because my throat had suddenly become quite tight and dry.

“Anyway, clothes are just a modern invention. Did you know that?” said Lisa. “For most of human history, we didn’t wear them. Birds and fish and animals don’t wear clothes, so why do we feel the need to tie ourselves up like that?”

“I... I don’t know,” I said, having never once even considered the matter.

“A lot of people think naturalism is a freaky sex thing,” said Lisa with a laugh that made her boobs jiggle around in a way that I instantly knew I’d never forget. “But really, it’s just about getting back to who we were, man. It’s about freedom. You like freedom, don’t you, Benjy?”

“Huh? Oh, yeah, yeah,” I said, too busy trying to sneak a peek at her bush to really follow what she was saying.

“I’m glad you’re so chill and open-minded about all this,” said Lisa. “A lot of people bug out. But you’re cool, aren’t you, Benjy?”

“Oh yeah, cool, cool,” I muttered, sweat beginning to form on my forehead.

“I gotta say, Benjy, you’re not looking so well,” said Lisa, her eyes wide with concern. “You’re not about to have one of your episodes, are you?”

“What?” I said, my tongue feeling like an old sock in my mouth. “Oh no, no. I’m fine.”

“Are you sure?” said Lisa. “Your face is a bit red, and I can see you’re sweating.”

“Oh,” I said with a hard gulp. “It’s just, uh, you know, warm in here.”

“I agree,” said Lisa, giving me a smile that had my pulse racing. “So why don’t you take off your shirt?”

“My shirt?” I said, my anxiety levels flaring sky-high.

Now, you’d think that a horny teenage boy would jump at the chance to take off his clothes in front of a pretty girl, especially one that was already naked, but you’d be wrong.

Well, at least in my case. I was pretty scrawny and pasty, and I was quite self-conscious about how I looked. Heck, I barely even liked to take my shirt off when I was at the pool!

“Come on,” said Lisa with a teasing grin. “I don’t want you passing out because you can’t breathe. Here, let me help you.”

There was just nothing I could do but sit there as she began tugging my shirt up. It was only when I realized I was going to spill my Kool-Aid that I snapped out of it, setting my glass down on the coffee table and then helping her finish the job. I expected her to laugh at me, but she just gave me a warm smile and a friendly pat on the thigh.

And that was the exact moment I realized I was sporting the biggest wood of my life, my penis tenting out of the front of my pants like it was trying to tear straight through the fabric.

The whole thing was completely and utterly embarrassing, but even so, my erection stubbornly refused to go away.