The Low Side of the Road

The following is a 99% true story, names have been changed to protect me from lawsuits.

For my entire life, the majority of my friends have been older than I and I always reveled in the perks I was afforded by having them. I had access to cigarettes first, I saw a real-live porno before anyone I knew, by the time I was 14 pot had become old-hat and in my sophomore year of high school I was granted access to senior parties. I was almost always the youngest person everywhere I went, but parties were a big deal because they were normally out of reach for anyone my age who wasn’t a relatively attractive and potentially slutty girl.

Now, I went to high school in suburban Milwaukee. The houses were big, everyone had a car and money for booze, and the rift between the elite and the invisible was nightmarishly large. Ergo, it was a bit to my surprise when my friend John (a Senior) pulled up in front of Travis Mackie’s house one Saturday night in August. John and I were in choir together and by most accounts John was not one of the popular crowd.[1] However, John played tennis; that made him cool-enough with the other cats on the tennis team and netted him certain privileges, one of which being party invites.

Travis Mackie, though, was your prototypical rich kid. He played on the tennis team, he was condescendingly polite, dressed well, and his parents were almost always away for the weekend. When we pulled into his massive circle driveway around sundown he was standing on the porch in his typical rich-kid-in-1999-uniform: cargo shorts, pre-faded Abercrombie & Fitch tee, hemp necklace, Birkenstocks, and can of Bud Light.[2] He approached the car with a slow, don’t-give-a-fuck-about-a-fuck saunter and his face and small talk for a minute before he asking us for our cover charge. ($5 all-you-can-drink parties were the norm)

Behind Travis, a guy I recognized as Trent was leaning against his car attempting to prop up his Friends-Only date.[3] His date, whose name I never caught and will henceforth be known as Drunk Girl, was already fucked up and the party hadn’t even started yet. She was thin and pretty with status-quo jeans and matching baby tee. It was abundantly clear that she shared with Trent the same type of relationship I shared with almost every pretty girl goodly enough to speak to me. You know, the pretty girl hangs out with the awkward guy because he always has her back, listens to her as if her every word could be the secret to cold fusion, and always volunteers to be her designated driver. In exchange, the Awkward Guy gets to be in love with her and occasionally accompany her in public.[4]

As the night wore on and more people arrived, the party proceeded in typical fashion; people played Caps, drunkenly confessed to crushes and half-true sexual exploits, and spilled more than was necessary. I, also in typical fashion, found myself on the back porch nursing shitty beer and trying to convince girls I was cool in the 3 and half minutes it took them to smoke a cigarette, 90% of which were bummed from me anyway. At some point the energy of the soiree changed. I noticed a discernable lack of partiers and an almost lunar-esque pull toward the stairs. When I reached the top and followed the dull mutter to the Master Bedroom, I understood the exodus.

A crowd of at least a dozen dudes had assembled in the spacious bathroom where Drunk Girl was in the shower fruitlessly trying to maintain her equilibrium. Sure, she was fully-clothed, but that had little effect on the near silence and copious number teenage jaws resting on the carpet. As proven by the immortal scene in the 1980’s film Porky’s, on the scale of all things exciting, getting to watch a girl shower is a mere one notch below receiving a Harrier Jet for your birthday.

Apparently Trent, being the astute Awkward Guy he was, had gently coerced Drunk Girl to get in the shower as a means of sobering her up before she had to be home. To this day, I am not entirely sure why people believe the cold shower method is a viable option under the circumstances. I’ve been in numerous drunken stupors in my life and none of them has ever been assuaged by running water. I do, however, understand why guys continue to suggest it to girls. It’s a virtual porno film waiting to happen. I would venture to guess that most of these films are still waiting decades later, but that does nothing to alleviate the hopeful diligence of horny students everywhere. And why not be hopeful? There’s a female mere feet away, in a place where one is typically naked. And who knows? I mean, the amount of time one can stand a rush of frigid water is a short one. And what’s to keep her from turning the knob to “Hot” and in a fit of refreshment, dropping her clothes and inviting a partner to join in on the scrub-fest?
Even as I type this, a grown man who knows better, this scenario seems oddly possible. After all, drunk women are more likely to engage in acts of senseless fornication. I just wish any of us had the foresight to suggest the shower routine before girls were fall-down-in-a-pool-of vomit drunk. The only actual hope any man has in a situation like this one lies in the question, “How are her clothes going to get dry and what will she be forced to wear in the meantime?” Again, no foresight. I’ve come to understand that when one’s penis becomes even mildly erect, the blood is allocated directly from the Foresight Sector of the brain.

While the rest of us feigned apprehension for her well-being and stood fascinated, half-waiting for her nipples to actually pierce all the way through her flimsy, sopping T-shirt, Trent’s gaze was a combination of embarrassment and chest-beating territorialism that is burned into mind, yet I still can’t accurately describe to proper justice. In truth, I probably had the same look when I orchestrated my own fruitless-but-ultimately-exciting version of this symphony during my Junior year.

Stories like this one, while few and far between, are surprisingly common in a young man’s quest toward manhood. High school is weird time; and even with an abundance of stories like this one, most guys will look back at their four years with an attitude of bored disdain. Most of us never actually got laid and if we did, it was probably a disappointing experience with a girl we never liked in the first place. [5] High school romance was a long series of Awkward Guy/Pretty Girl torture sessions culminating in a “Please-God-just-take-my-virginity” grope-a-thon with the only available bidder, usually a shy, smart, average-looking young woman that would make an excellent present-day girlfriend, if we had ever kept her phone number.

The absolute pice du resistance in the Awkward/Pretty saga happened to me at the tail end of my Senior Year. Her name was Amy and to this day, she was one of the prettiest girls I’ve ever known. She is also possibly the hottest woman I’ve ever seen naked and in person at the same time to this day. You may be asking, “How did this happen? Does this not shatter the Pretty/Awkward mold, completely disproving everything said up to this point?” The answer is ultimately “no”. And here’s how it went down (or more accurately, didn’t):

Coming into my final semester, I played the classic role of the tortured teenage artist desperate to break free from the chains of conformity. If this was going on today, I would have been labeled an Emo Kid. At that time, though, the term “Emo Kid” was not part of the lexicon. I was about 70 pounds overweight, an aspiring songwriter, the lead in the school play, and in serious danger of not actually graduating. I hated everything about school and never did homework or studied. I had made a career out of coasting by on talent and superior negotiating tactics and it had finally caught up with me. Therefore, it seemed only natural that I take Creative Writing as my final Senior elective class. It appeared to be something I could effortlessly glide through, especially considering my interest in the arts and penchant for the written word. On the first day of class I discovered two things: 1) this class was so rudimentary that a middle school degenerate could ace it and 2) Amy Keller was the sexiest girl in school. By the second week of class I was sitting behind her cultivating a serious crush and collecting puddles of drool on my notebook.[6] Amy was different than every female I had ever encountered. She seemed to have her shit together in all the right places. She was insanely attractive by anyone’s standards, but also the type to never act is if she knew it

As the semester progressed, we developed an interesting friendship. She liked me because I was this Pre-Emo Kid and didn’t think or behave like anyone in school. I was into music and books and film. I hated school-sponsored activities that weren’t focused on the arts. I may have well been the only guy she knew in that place who smoked cigarettes and wasn’t trying to either hide it or impress anyone with it. We would talk about the decline of rock music and the finer points of Tom Waits. In fact, she introduced me to Tom Waits. Before her, I only knew he existed and VH1 had listed him in their Top 100 Artists of Rock and Roll list. She came in one morning raving about his album, Mule Variations, which would later become my favorite of the year and win a Grammy. When she brought it up I pretended I had already heard it. In all likelihood, I probably dismissed it as, “Not bad, but it doesn’t really do it for me.” This is a phrase I used a lot when feigning knowledge about music and film I know nothing about but felt I probably should.[7] It was not, however, her interest in Mule Variations that made me buy it. What made me buy it was the fact that she mentioned that she once performed a strip tease to the song “Low Side of the Road,” the album’s second track.

Amy had a boyfriend, naturally. And naturally, it wasn’t anyone at our school. He was an older guy, 19, working on his GED. If my memory serves, he worked at gas station and drove a dilapidated Oldsmobile, which he once bragged about as being the vehicle involved in his successful outrunning of the local police. It seems girls like Amy always date chuds like this; perhaps it’s because it makes them feel even further removed from the usual high school girl. Regardless, Amy’s relationship with said boyfriend meant very little to me. He wasn’t around, therefore he didn’t exist. He couldn’t possibly understand and appreciate her the way I did. He didn’t see the way she looked at me. He also wasn’t there the day I took her shopping at the mall and helped her put together a new outfit, a skill I picked up from being raised in a family loaded with women, and a scenario that I understand now to be a non-negotiable ticket to the Friend Zone. Hell, it was a ticket to the only thing worse than the Friend Zone, the Possibly Gay Friend Zone.

One weekend that Spring she and I finally spent some time together outside of class. My friend Mark had an apartment (again, an older friend) where I spent most of my time and I invited her over to hang out with us. This situation seemed perfect as it was somewhere private, but another guy was around so it seemed non-intimidating. There was also booze and a wealth of available ashtrays. I had relayed to Mark how much I liked her and undoubtedly described how hot she was, and when I told Mark about the Low Side of the Road Story, it was all I could do to prevent him from calling her himself. She came over and we hung around doing nothing note-worthy, mostly talking and drinking, until she had to split. She made an appearance at his apartment several times over the next few weeks and even brought her boyfriend once. I was actually happy to see him, as he instantly proved to be exactly what I thought he was - a nice guy but ultimately a douche who was no match for my supposed wit and charm. On the nights when he wasn’t present, the conversations ran the gamut from music to Robert DeNiro to sex. (Not sex with Robert DeNiro, mind you, but sex with her boyfriend.) I remember her talking about her inability to climax via masturbation and how her boyfriend could “hold his nut” for over an hour. This immediately placed nut-holding at the top of list of things to learn, second only to learning how to have sex with Amy while holding my nut.

Sex was constantly discussed when we got together. More than likely it was because she was actively having it and I had only done it twice. I was earnestly interested in being a good lover, not just dry finger-banging some chick in the back of my Toyota. She actually once demonstrated her favorite sexual position to me on Mark’s living room floor. As she instructed me to position myself over one of her legs as she slid the other behind my head, seeing Amy naked became the most important thing to me since learning to play guitar. My crush had evolved from crush to infatuation. Amy even passed my Infatuation Test

I could masturbate to anyone when I was a teenager. It didn’t even matter if I was remotely attracted to the person involved. Actually, most of the people I thought of while spanking it were not anyone I would even sleep with given the opportunity. (For one reason or another, this still holds true today.) It went so far that I physically could not jerk off to anyone I wanted to be with in real life. Even following a guided tour of the Kama Sutra, I wouldn’t allow the image of Amy or any other girl I was crushing on to enter my mind as I masturbated. I guess at the time I felt it was demeaning to girl involved and cheapened what we had, even if “what we had” was nothing more than my crush and her sibling-esque fondness for me. No one had ever turned me on more than Amy Keller but I still never once touched myself to her image until the incident that marked the decline of our friendship.

The circumstances involving the night of said incident are hazy in my memory but the details of what went on are for the most part very clear. I’m not sure what day it was or at what point in the semester, though it was probably a Friday night. I have no idea how the actual subject of her alleged striptease came up, though I probably instigated it. All I remember clearly is the image of Mark sitting on one couch, me sitting on the other and Amy on the way down to the car to get her copy of Mule Variations. Chances are we all feigned something innocent, but everyone knew what was about to happen. Amy was going to re-enact the fabled striptease that up until that point existed as the pot of gold at the end of my awkward rainbow.

Reader's Note: I’ve toured the country on several occasions. I have played packed houses, and met most of my personal heroes. However, what happened over the next 2 hours that night is probably the coolest thing I have ever been privy to.

As she re-entered the small apartment, now glowing under Mark’s beloved blacklight, she closed the door behind her and proceeded to the CD player that constituted Mark’s stereo system. “Low Side of the Road” filled the space like the Marlboro cigarette spewing from my anxious, gaping jaw. Low Side is an incredibly sexy song, and not just under the circumstances. It walks the line of creepy, low-fidelity and unabashed grime like few songs have in history. Waits’ gravely timbre and slinky guitar play so perfectly against the plodding pulse I would dare anyone to listen to it and not feel compelled to roll their hips against the air. By the start of the second verse, Amy was doing just that, grinding up against some phantom pelvis and gently mouthing the lyrics. At first, her clothes remained on and her eyes stayed firmly shut. She hinted that she was just about to remove her first layer when the song ended . For a moment, she broke character and out of the trance, her eyes popping open like Kim Cattral in Mannequin. Mark, being the stand up guy he is, reached over and started the song again. with the haste of a driver who just dropped a cigarette in his lap. In an instant, she fell back under the spell and began taking off her top. Until Mark, in a stroke of genius remembered his CD player has a repeat button, we carried on like this roughly every three minutes: Amy swirling about the carpeted floor, her hair whipping across her face, the track ends. Amy’s thumbs begin flirting with the straps of her bra, the track ends. The amazing part wasn’t her willingness to keep re-starting the process, it was the exasperated sigh that followed every stop. All signs pointed to her absolute desire to strip at length for two horny idiots, neither of whom was her boyfriend. But with the repeat button deployed, no longer would the tyranny of time stand in our way.
Amy’s perky, flawless breasts finally entered the equation. Shortly thereafter, her skirt and thong followed. For an entire rotation of the song, Amy stood there, wearing nothing but a scrap of fabric, tracing circles around her nipples, never missing a lyric. By the time the night was over, everyone in the room had the song memorized. We knew every line, guitar riff, and section cue- from the lick that accompanied the start of a new verse to the sloppy transition at the end of the bridge.

I distinctly recall the throbbing of my dick as it jammed itself against the front of my jeans, I recall shifting it to one side just as it started to leak, and I especially remember a now-naked Amy crawling across the floor with her eyes locked on mine. She leaned in and whisper-moaned, “I want to see you touch yourselves.” The plural indicated that she meant Mark as well, which she made very clear when she crawled to the other couch and said the same to him. For a second I froze. You see, I was just getting to the point in my development where I could admit that I masturbated at all and now here was this girl asking me to do it in front of her and my best friend. It’s an odd thing to have to consider at the age of 18. When I saw police lights, I knew to run. Fight breaks out? Start swinging. Beautiful young woman asks you to take your dick out as she writhes naked on the floor? Freeze. Years later, having my dick out in front of my friends is still high on the list of things that make me uncomfortable. It’s not that I’m homophobic or have any issue with the idea of naked men, but when my friends are involved I’d much rather not masturbate in plain sight. I would go so far as to say that I’d take a bullet for a few of them, but I’d hesitate to drop trou with them in the room.

For a second I contemplated my situation, never more unsure of what to do in my life. So, I did what any 18 year old Awkward Guy would do: I giggled like a little girl. A high-pitched, guffaw stifled by my hand sprung from me at an alarming rate. I couldn’t stop it to save my life. Seconds later, Mark stopped it for me.

“Dude. Stop giggling. Just take care of business.”

Mark, a recovering homophobe and generally conservative, already had his shorts undone. Not wanting to hold up the party, I followed in kind. When I removed my piece from my jeans, I was so aroused I thought my skin might tear. I was probably about 4 strokes from an orgasm of geyser-like proportions, but if jerking off in front of my friend was embarrassing, I only imagined how mortified I would feel after launching a massive brick on his furniture. Now with two young men openly stroking themselves, Amy was visibly aroused. She was panting and sweaty, writhing against the floor, her neatly trimmed vagina humping the air like a phantom cock. I convinced myself that I was the phantom she was thinking about and if we were alone we’d be going at it for real. It didn’t even matter if it were true. I just sat there, sloppy dick in my hand, the luckiest schlub in existence.

Our collective sense of reality was gone. This was a consequence-free alternate universe, completely devoid of time and any other human being beside the three of us. I’m not sure exactly how long this scene had been going on, but it could have persisted until graduation. I would have gladly skipped the ceremony. It was a scene of suspended linear relativity. It was much like a long walk your last day at camp or on vacation. You know it has to end; eventually you will have to collect your things or hail a cab, but you tell yourself that if no one mentions it, sunrise will cease to arrive.

Our sunrise did arrive, however, with the sound of annoyed footsteps coming up the wooden stairs and a violent knock at the door. We all launched into action; Amy scooped up her things and ran toward the bedroom, Mark zipped up and answered the door, and I crammed my still-erect penis back into its denim holster. I watched Amy’s shadow get dressed in the darkness of the next room as a man’s voice muttered something I couldn’t make out on the other side of the open door. It was the building manager. Someone across the alley had reported that the music was too loud. Because it was warm out and Mark’s building being old-style brick, we had the windows open. I guess the sound was traveling farther than we anticipated. I joked to myself that I was amazed anyone could hear the music over the wet, slapping symphony going on.
Mark closed the door and we looked at each other with a mix of disappointment and utter disbelief. It was almost the same look we would have shared had we just dumped a body in a ravine. He whispered something and motioned toward the bedroom. Mark is an unbelievably standup guy. He facilitated this whole scenario and wanted nothing in return. Sure, he got to see a show with the rarity of Halley’s Comet, but just about anyone else would have been clamoring to get a chance at being the guy who followed Amy into the bedroom. In theory, if I ever had a chance at closing the deal with Amy, now was the time but when I entered the bedroom, I found our alternate universe shattered. She was sprawled out across the bed, face-down in the pillow. She wasn’t crying, but as tense and pensive as anyone who just pranced around naked in front of two idiots, neither of which were her boyfriend, would be. I ran my hand gently up one of her legs, stopping mid thigh. As I started on to the next, she rolled over and looked at me.

“I can’t. I just can’t.”

Naturally, I understand why she couldn’t let this go beyond a spectator sport. (Even if she did technically grab my dick for like 2 seconds at one point) I mean, she did have a boyfriend. He was kind of a douche but he certainly didn’t deserve to be cheated on, even if he would never understand her like I did.[8] And while I completely see how this could be viewed as cheating, it wasn’t for her. Amy was a very sexual, very exploratory being. From all accounts, she was active before almost anyone and was obviously an exhibitionist. She even told me that once when she was a girl, she had clubhouse that her father tore down when it came out that she was giving peepshows to the other neighborhood kids. (She vehemently denied the validity of the story, claiming that she never did any such thing, but it’s kind of hard to believe her in light of everything.) To her, the evening was just a chance for her to express her sexual urges in a “safe” environment. Amy loved a dirty little secret as much as anyone and while I viewed this whole experience as a clear indicator of her feelings for me, it was probably anything but.

Amy and I talked about that night a few times as the semester drew to a close, but never in any context besides, “Man, that was weird.” If I remember correctly, she broke up with her boyfriend shortly thereafter and I made some attempt at asserting my feelings to no avail. From there we just drifted apart, I guess. Unrequited love is a hard thing for everyone involved. Once it’s uncovered, it is equally uncomfortable for both sides. No one wants to hurt someone they care about and nobody wants to be cared about outside of their own terms. Even now as an adult I’d rather not be with someone at all than exist as a friend with no hope of ever being anything more.

Mark and I eventually talked about the event, but not until several weeks later. Once we called out the elephant, we continued to be best friends but never jerked it next to each other again. Sure, we attended strip clubs together a few times. We had a stripper in our shared room once in Vegas, but it wasn’t nearly as cool and our pieces stayed put. The mention of Tom Waits will still make us giggle. I slept with his wife once. To be fair, she wasn’t his wife at the time, but you get the picture. From that night forward, we became inextricably bound. When I gave the toast at his wedding, I really wanted to tell this story but his wife doesn’t have much of a sense of humor about these things. We don’t talk as much as we once did but we will always be close.
Technically, I ended up failing Creative Writing (Oh, The Irony!), but was allowed to pass through due to a modified final exam. While everyone else just turned in the poems and whatnot they’d spent the semester creating, the teacher told me if that if I typed up and played a few of my songs for the class, she’d pass me. For the record, I still tell everyone I failed Creative Writing and at least two of the songs I turned in were for Amy.

[1] He was actually kind of a dork.
[2] Were he a middle-class “bro” he would have been drinking Natural Light.
[3] Trent and John shared a special bond in that they both were included via history. Neither one of them really belonged here. John, Trent and Travis had all grown up playing tennis together and were thus all friends. But as Travis ascended to his natural place in the wealthy Diaspora, the other two didn’t come from that stock. They were just quiet, nice guys who half-heartedly played an ill-fitting sport
[4] Personally, I hold popular cinema responsible for glorifying the awkward Guy archetype. That, however, is another essay altogether and Chuck Klosterman has already said it better than I could.
[5] I realize this sounds callous, but I’m nothing if not appallingly honest
[6] Crushes like this one were nothing out the ordinary. I had a string of them each year to the point that I found myself making actual lists to keep track of them all. At the time the Amy saga began, I was nursing a trampled heart from the end of a pseudo-relationship with a beautiful girl who was much too crazy for anyone’s good; a girl I still refer to as “my first love”.
[7] In fact, if you ever hear me say this today, there is at least a 50% chance I have no idea what I’m talking about.
[8] Part of me thinks this didn’t end here. I remember something about ice cubes. I’m not sure if this happened on the same night or a different one. Is it possible this happened more than once? My memory is awful do to genetics and recreational drug use. Damn them both.