File this one under "essential survival guides"

"Black Lubrication and the Sexican Standoff"
by Troy Frost

This is a true story but the names have been changed to protect the innocent... except for mine, because I'm guilty as fuck.

My relationship to the fairer sex has always been a bit... complicated. I was once a teenage boy after all, and we all know how smoothly things go around teenage boys.

It's very distracting being a young man, everything you see gives you a raging erection. The lingerie ads in the PennySaver newspaper, your friend's mom, sometimes your sister. It's really NOT cool.  As a teenage boy in the 90's my life was very simple and I found my time and brainpower divided across sex, video games, skate boarding, sex again, Mountain Dew, and violent masturbation. Mountain Dew comes before violent masturbation, that's very important.

Back then there was a movie called "Wayne's World" that had a scene where a character describes a feeling in his crotch as "like when we used to climb the rope in gym class". Every young man that attended grade-school gym class before they started handing out participation trophies for watching other students play ping pong knows exactly what they're talking about.  I can tell you that's actually a thing, and I could never get to the top of that god damn rope without wetting the front of my pants.  Sometimes I'd just hang out up there until class was over to 'test my endurance', or at least that was my excuse.

All of this happened before the internet existed mind you, and long before online porn consumed 38% of the world's natural and human resources.  Today young boys can get any porn, anywhere, at any time.  I still can't fathom what that must be like.  For us back then porn was very different. It wasn't just our primary source of entertainment; it was our fucking currency! You could literally trade that shit for a firearm. Today's kids are billionaires by 90's teen standards. If I could go back in time I wouldn't trade the stock market, I'd bring back all our porn and trade it to my younger self.  I actually did the math on that, the porn produces a higher return on investment.

Like most currencies, the porn we peddled back then was of the paper variety. Magazines were small, easily transportable, and could be 'used' anywhere. The photos in those magazines were also 'normal'.  By normal I mean in the sense of just two people in a traditional sexual act, not the gangbang bukkake Japanese tentacle shit play that we're used to now. Boys have and still do get their primary sexual education through pornography, and ours was... somewhat medically accurate.

Regardless of where or when you get your sexual education, I think the first time anyone has sex it's inevitability going to be awkward, especially if you happen to be a teenage boy.  I can't imagine an initial encounter like that going down any other way, it's just not possible, you have no concept of your angles yet.  It's a math problem that you solve with your dick and NOBODY studies for the quiz.  Show me a person who just dives in like a pro the first time they get it on and I'll show you a fucking time traveler.

My first sexual encounter was with a girl I went to Highschool with, Missy.  She was a very cute girl, about my height, brown hair, kind of a hippy but in a cool way (I had a thing for chicks like that). I was lucky to have her in my life. We had known each other for almost a year, the entirety of which I spent figuring how to get into her pants. Missy also happened to be my sister's best friend, which made getting her alone a strategic game of thrones.  

Then, one day while skipping school, I found myself at home with my just my sister and the primary target.  My parents had stocked the liquor cabinet with old people booze like peach schnapps and Black Velvet. So I did what any good host would do - get everyone slamming drunk on someone else's stash.  They say that necessity is the mother of invention, and my inventive mind could get pretty creative when it came to alcohol.  I was a sixteen year old master mixologist, and I wouldn't let a little thing like resources get in the way of a party so I designed a cocktail that mixed peach schnapps with mountain dew in a beverage I call "Social Lubrication."  There was just one problem, the peach schnapps was almost gone and the only other booze we had in liquor cabinet was Black Velvet.  I knew my Social Lubrication was an established hit with the ladies, but if I wanted any chance to get everyone buzzed, I'd have to introduce an untested ingredient, the Black Velvet.

Black Velvet is a Canadian whiskey that tastes like your grandpa’s nutsack. You must be at least 50 years old to enjoy it, and that's all you need to know about Black Velvet. Fuck that shit.

I could sense my guests were getting restless, and the teenage alchemist in me had to make a decision. I figured my odds of concocting something palatable to be around 50% so, with reckless abandon, I poured the Black Velvet into the bottle of Social Lubrication to create "Black Lubrication."  This wicked potion has the potent effect of making other people hate you while you resent your life. It's not something that an adult would drink, or anyone for that matter. I returned the cap and shook the Mountain Dew bottle... like an idiot, in an attempt to mix the ingredients.  My sister had retrieved some classy and artistic stemware rendered in the style of Dixie cups.  She placed three cups on the kitchen counter.

"Would you like some Black Lubrication?" I said, as if anyone else got the joke. Half of my sister's brow furrowed, the other half was pointed right at me.

"Cheers," I said, BEFORE I poured the booze. My sister and Missy stole a glance from each other.

Of course I wanted to serve Missy first, so I used the force to summon more of the alcohol to the top of the bottle.  She held out her cup, and I obliged by opening the cap of the pressurized bottle that was now pointed at her face. I could feel the cap's threads clear the bottle and the force from the ejected black lubrication. For a brief moment I actually thought that maybe it would all land in her mouth. But physics being a sloppy bitch and all, Missy instead found herself with a face full of flat, dripping wet Black Lubrication.  Not a single drop found its target.

Missy wasn't the type to scream at something like that, she was more of the hold her breath and judge your future kind of gal. My sister meanwhile began to freak out, worried that our parents would discover that we'd skipped school now that I had alchemically transmuted our expensive beige carpet into a edgy but tasteful leopard print rug. Apparently my sister had no appreciation for the dark arts, as she dropped to the floor and began scrubbing.

I turned to find Missy but she was missing. I figured she must have gone upstairs to clean herself up.  My first instinct was to dive in and help my sister cleanup the mess.  I was after all culpable here too, but then I realized something.  My sister is distracted and Missy is alone, upstairs, near my bedroom and the probability of her being topless was high enough to override my parental fear. I bolted up the stairs to find her in my bedroom donning one of my black t-shirts.

"GOD DAMNIT" I thought, "I just missed it"

"I borrowed your shirt" she said with a factual tone.

Of course a young man can never show his true emotions so I gave my best attempt at acting nonchalant.

"Cool, but that's going to cost you" I said, like a complete fucking moron. That wasn't the first time I put my foot in my mouth around her; I once told her that she "looked beautiful in the dark".

"Oh, would a face full of brown liquid shit about cover the tab?" she said coyly.

I was a try-hard guy, always persisting but never succeeding. I think she may have seen that in me, or maybe she wanted it just as bad as I did. In my experience as an older, slightly wiser man, the latter tends to be true more often the former.  We started making out, and then our pants came of, but we kept our shirts on because... reasons.  I realized that I was wearing my best friend's jersey, who also happened to be her brother.  I don't know which act was more sacrilegious - screwing my sister's best friend and my best's friend's sister at the same time with one penis, or cleaning up the mess with my buddy's jersey.

Sacrilegious or not, I'll never forget how it felt to be with someone for the first time. My anxiety began to vanish revealing honest human emotion.  I felt that sense of being so connected to another person that you can't tell where you start and she stops. I felt my fateful curiosity melt away.
When you actually do the act for the first time, you realize a lot of things; that porn is mostly incorrect, sex requires a lot less contortion and physical exertion than you'd expect, and the vagina was much closer to the butt-hole than you originally thought it was.

It was pretty clear that I had no idea what I was doing, like an athlete who’s spent an insane amount of time visualizing his sport but not practicing it.  It was Missy’s alleged second time so I felt like a complete idiot trying not to ruin it for her. My confidence was boosted once I had deduced the mechanics of the act, but that was short lived when my sister barged into my room, unannounced, looking for a pack of cigarettes.  

I stopped, but the bed kept squeaking as if to beckon my sister to look in our direction. I then witnessed the slowest head turn in human history, and the look on everyone’s’ face clearly acknowledged the awkwardness of the situation. Like a classic western film, I found myself in a ‘Sexican Standoff’ chuckling to myself in front of my sister while balls deep in her best friend.

Needless to say we all walked away from that situation a little worse off and potentially traumatized. My personal loss included self-esteem, my sister's respect, and $40 to my friend for defiling his jersey.

I'm confused.

Is this an essential survival guide, or is it fiction?

Too funny, OP.

I could picture it all, too. Well written.

"Tastes like your Grandpa's nutsack" do I need to ask how you know what that tastes like?