Postcards from a Wasted Youth: Episode 2

When Holly and Courtney asked me to go to the city with them one night, I had no idea what it would lead to: one amazing and crazy summer.

Postcards from a Wasted Youth: Episode 2

EVEN IN MY EARLY teens, I was a kid who was allowed a lot of freedom. To this day, I’m not sure if it was because my dad trusted me or if it was just because he knew there wasn’t a chance in hell I could be contained. After all, I was a rebel! A kid who got it done, sir! I went where I wanted, and did what I wanted, and there wasn’t anything that was going to get in the way of my good time!

So what did I do with my rebellious spirit? Go out binge drinking? Nah. Steal cars to go on joyrides? Only once, and it was my mom’s car (the cop told her that I drove quite well for a fourteen year old). No, mostly I spent my time hanging out with friends at the diner.

New Jersey is known for a lot of things, but three stand out: highway exits, girls with sky-high hair, and diners. Diners owned by Greek families, to be specific, and they were multitudinous in North Jersey. My favorite was always the Randolph Diner, especially since it was right down the street from my house, but if you were looking to spend a lot of time doing a whole lot of nothing after two a.m., you had to go elsewhere during the week. Diners in North Jersey were becoming the thing, and later on in my life, I would waste too many nights in them, mostly with my group of gaming friends. At the Randolph Diner, on Thursday nights, we owned that place; our numbers were easily in the 20-30 range, and Diego, our regular waiter, made bank on those shifts. We would pack into the smoking section, armed with Magic: The Gathering cards or D&D campaigns.

But we’re not there yet: rewind to fifteen. So it was that some of my friends - most of whom were older kids who drove - would spend many a summer night at the Victoria Diner. An all-night venue with vigilant owners who made sure if you were going to drink coffee into the wee hours that you were going to eat meals to go along with it, it was the only game in town that was close by, and we kept the tips decent enough to stay in their good graces.

On one of those hot summer nights, a few months after I turned fifteen, we were just about ready to leave and were in the parking lot, lighting up our cigarettes, when I heard a girl’s voice call out my name. I turned around, and there was Courtney.

Courtney: a lithe, blonde-haired senior with pretty, narrow eyes and thin lips, a couple of inches taller than me, and athletic. She played lacrosse and had thighs that could snap your neck in two. She was also really sweet. I met her through another kid I knew named John, who I think might have been hooking up with her when he introduced us a few months earlier.

Needless to say, I walked over to say hello. One does not just ignore a very attractive, older girl who is addressing you across a parking lot when one is fifteen.

“Hey,” I said, sauntering over there like I thought I was James Dean or something. She was dressed more girlishly than I had seen her before, in a pretty white dress, and she was with a couple of other well-dressed people. She introduced me to her friend, Holly, and Holly’s Dad, whose first name has been lost to a bad memory. We stood and chatted for a bit, all three of us; I charmed Holly’s Dad, something I was good at in those days. My friends were all leaving, but Courtney had other plans for me. “So, we’re going to drop Holly’s Dad off and then maybe hang out. You in?”

You should already know that I wasn’t going to say no to that.

I CRAMMED INTO THE BACK seat with Holly’s Dad, and after the short ride back to their apartment, where he disappeared into their home with a wave and a “have fun, kids!” remark, Holly, who was driving, said, “so… to the city, then?”

“The city” to Jersey kids only refers to one place, and that’s New York City. About an hour by speeding car, it was the most exciting place Jersey kids knew. I had never been there, and was a little nervous about this adventure, but… girls! Two of them! Courtney and Holly exchanged looks and smiles as I said I was game, and Holly peeled out of the parking lot.

Holly: 5’3”, brunette high school senior with eyes that make your pants tighten when she looks at you and an ass that wouldn’t keep a quarter you dropped on it. 17 years old, moved to New Jersey from Texas, and liked yellow cars when yellow cars weren’t so stupid.

On the way to the city, the girls grilled me on everything I could tell them about myself. I had never received this much attention from two girls at once, and especially two seniors. I mean, older girls just didn’t dig freshman guys, and yet… here I was. And as we sped down the highway that would take us to the Lincoln Tunnel and the spectacle that is Manhattan, I was certain of two things. For one thing, I wasn’t going to make it home that night, at all.

For another thing, not making it home was going to be so worth it.

I DON’T THINK THE GIRLS had really done much in the city before, either, because we didn’t spend much time there at all. We got gas, ate at McDonald’s, then turned around and headed back to New Jersey. We were there for all of an hour.

Me, well… I was still having a grand old time. Sitting in the back seat, somehow garnering the attention of two hot older high school seniors was absolutely enthralling. While Holly drove us back into the ‘burbs, Courtney was sitting sideways in the passenger seat, her hand on my leg, throwing me frequent smiles.

So worth it, indeed.

When we arrived back in Randolph, it must have been about three in the morning. They asked me if I wanted to come inside.

“Won’t we wake up your dad?” I asked, suddenly nervous.

“Nah, my dad sleeps like a log,” Holly said, and inside we went. I couldn’t see very well in the dark, but Holly took me by the hand and led me into the room she shared with Courtney, who was following close behind me. I sat down on the bed as Courtney closed the door behind us, and I looked around at my surroundings. Lots of soft lighting sources; lava lamps, an aquarium, and other little light-up knick-knacks dotted the room. I sat down on the edge of the bed.

Holly put on some soft music, and jumped on the bed behind me, locking her legs around my waist as she began massaging my shoulders. I was very confused. I thought Courtney liked me, but here Holly was, her hands all over me… “Here, lie down on your stomach,” she instructed. “You’re all tense, and I’ll give you a proper massage.”

I did as she bid. My heart raced as she took my shirt off, and then I felt her warm, massage-oiled hands on my back, my spine, rubbing all of the tension out me. I had never before felt anything like what this girl was doing to me. It was erotic, relaxing, sensual… things I didn’t really know existed before. I was so relaxed, I don’t even remember falling asleep.

I DO REMEMBER WAKING UP next to Holly, her arms around me, the sun streaming in through the venetian blinds above her bed. It should’ve been hot, but the air conditioner was running; I felt cool as a cucumber, and well rested in her enormous bed. However, something seemed off, like there was something I should remember about last night, but it was foggy as consciousness came into focus…


I slid from under Holly’s arm, and sat up, looking around the room for Courtney. She wasn’t anywhere. I gently shook Holly, who was lying next to me in the same clothes she was wearing the night before. She awoke with a start.

“Where’s Courtney?” I asked. It seemed early in the morning, no later than seven, and I couldn’t imagine she’d gone somewhere. I looked over at the clock. It was 7:04. Holly gurgled something in her sleepiness. I swung my legs over the side of the bed, and pulled a crushed pack of Marlboros from my jeans pocket. I smelled coffee brewing, and I fired up a cigarette. “What did you say?”

Through her pillow, I heard, “she slept in the car.”


Holly flopped over on her back. “She’s jealous you ended up in bed with me.”

I drew on my cigarette. “But it’s not like we did anything. I fell asleep.” And though I was justifying myself to Holly, I did feel at least a little bad. It was obvious from the night before that Courtney liked me, and, if we’re telling the truth here today, I was much more intoxicated by Holly. Courtney was attractive, but Holly was electric. She stirred some primal feelings in me I’d never experienced before, and she was goddamned sexy. I’d seen sexiness before, but never had I slept in the same bed as it.

A few minutes later, Courtney came in the room. “Morning, kids,” she muttered, dropping a blanket on the floor. “Holly’s Dad is awake, and he made coffee.”

THE NEXT HOUR OR SO should’ve been uncomfortable, and it was. We sat around the cluttered living room; me, Holly, Holly’s Dad, and Courtney. I smoked a few cigarettes, as did Holly and Holly’s Dad, during the awkward “hey you slept in my daughter’s bed last night” minutes.

“So, you go to Holly’s school?”

I didn’t, exactly. I’d gotten in trouble in the year before I was to enter high school, so I was sent off to a “special school” for not as well-adjusted kids. I was sent away for something stupid, really. A misunderstanding. But before I could divulge all this, Holly spoke up.

“Yeah, he’s a grade below me,” she lied. I swear I saw her eye twinkle. Her dad nodded, and sipped his coffee. I lit another smoke. The rest of them made regular morning small talk, and after an hour or so, I split.

I spent most of the day at home, hanging out with my dad before heading out to the coffee shop with a book. I’d been reading No One Here Gets Out Alive, the acclaimed biography of Jim Morrison, and I wanted to dig into it a little. Then I wandered back into the complex, and over to their apartment. The walkways actually led me past her bedroom window, and the sun was starting to go down, so the light on in her room told me she was home.

I went to the front door and knocked. Holly’s Dad opened the door. “Johnny m’ boy! We’re ordering pizza!”

WE WERE IN HER ROOM, waiting for the pizza to come. It would be about forty-five minutes (since "30 minutes or less" promises had been all but outlawed due to some pretty bad car accidents). Courtney went out for a bit when I came in; again, I felt a pang of remorse. The hormones of a young boy usually outweigh any moral outrage at barely slighting someone, however.

I don’t remember what the conversation was, or even if there was one. The memory of this night starts at her throwing me down on the bed and straddling me. This was something new for me; no girl had ever been so aggressive with me before.

She leaned down on me, kissed me hard, and then sat back up. I was stunned, and it only got more intense when she took her shirt off, revealing a white lace bra. I involuntarily had a situation happening below where she was sitting, and it didn’t go unnoticed; she began writhing on top of me when she reached behind her back, and started undoing the snaps to that bra, while asking, “do you want to fuck me?” Holly was nothing if not direct.

I stuttered. “Y-y-y.. well, I mean... of c-course, I...”

“Wait,” she said, re-securing the bra. “We can’t. My dad’s just outside, and if he were to come in while I was naked, on top of you... but, I could leave my clothes on and give you a blowjob!” she exclaimed cheerily.

Before I could answer, she swung around, rear end facing me, and I realized my pants were being unbuttoned and unzipped. I could not--NOT--believe this was happening. Here I was, a fifteen year old virgin, about to have this happen with one of the sexiest girls I’d met - at least, up until then. She was older than me; that was exciting. She was so sexual, and that was exciting. And she was dangerous.

That might have been most exciting of all.

Before I knew it, her mouth was on me, and though this was not the first time I’d been the recipient of oral sex, this was the first time it was so good. She used her teeth, her lips and her tongue to create sensations that until then I’d never experienced, and haven’t again to this day. I did everything I could not to scream when she finished, and I bit down on my lip, hard. She wiped her mouth, which was wearing a wicked smile, put her shirt back on, and said, “yay, time for pizza!”

I said, “wait, I need a few minutes.” I was still in shock, and in heaven. I lit a smoke, inhaled deeply, and whispered, “that was incredible.” She looked at me as if I had said the most obvious thing in the world, and in retrospect, it was. When I finally regained my composure, we joined her father and Courtney in the living room, where what was probably the most awkward experience of my young life was about to occur.

As we sat on the couches, eating our pizza and generally having a good time, Holly's Dad grinned slyly at me, and said, "it's amazing how much she can fit in her mouth, isn't it?"

I nearly dropped my pizza, but I kept a straight face, and glanced at Holly, who was indeed inhaling a medium slice at breakneck speed, and replied, "sure is!" He winked at me, and then resumed eating. After my bite, I breathed a quiet sigh of relief.

THE SENIOR PROM WAS ONLY a couple of weeks away, and Holly was fretting about whether or not she'd have a date. I didn't present myself as a option, knowing that she couldn't really bring me to such an event without sacrificing herself on the altar of High School Coolness. She ultimately decided to skip the dance, and asked me if I would come over and keep her company since she was likely going to be sitting home, solemnly contemplating her lack of a boyfriend. I quickly agreed to be her date for this lonely evening. "You have to promise me one thing," she said. "If I get completely hammered, which I probably will, you can't have sex with me." I would never have even thought about taking advantage of her, so I put to rest any fears she had. "I would never do something like that," I said. I meant it; I couldn't fathom being that cruel, not to anyone.

I arrived at 8 o’clock; Holly’s Dad and Courtney were out for the evening, so it was just the two of us. Holly was half into a bottle of wine, from which she offered me a drink, but I wanted at least one of us to be sober and responsible. I wasn't so sure I could resist her if I had also been inebriated.

We made out quite a bit, progressing on to a more erotic and intimate playtime, but there was no sex that night. In between various stages of fooling around, she got drunk, told me all about her life in Texas, and asked me questions about my life. I told her about Meredith, about my parents splitting when I was six, and my boring hobby of computers.

It’s safe to say we didn’t leave the bed all night, but I realized later I probably should have. I found out that night that Holly is Crazy, with a capital C. She teased me about wanting to have sex, and each time I rebuffed her, keeping my word. She showed me the huge bucket of condoms she kept in her nightstand, every conceivable type of sheath on the market was in there: lambskin, extra large, lubricated, unlubricated, ribbed... she had it all. At some point in the wee hours, she got up to go to the bathroom and came back completely naked. I was in awe of her body; this was the first time I’d been in bed with a completely unclothed other person. She was stunning. She laid down next to me, and we made out some more, but then she sat up and started... punching herself in the legs?

“Holly! What the hell are you doing?”

She started crying. “I’m so fucking stupid, I hate how stupid I am!” I grabbed her and held her so she’d stop hitting herself. She hung on to me, crying into the crook of my neck and shoulder. I was confused; I didn’t understand what was happening, but it occurred to me just then that this girl totally had some issues. I probably should have been tipped off that she was 17 and fooling around with me. She finally stopped sobbing a few minutes later.

“I’m sorry... I... do that... sometimes,” she said.

“It’s okay,” I whispered. I didn’t want to press the issue too much.

We stayed up all night, touching each other, holding each other, kissing each other. By dawn, we were still awake, lying in bed, her back to me. She was grinding against me, and I was grinding back; she was driving me absolutely crazy. Finally, when it was light out, she was on top of me, pulling me out of my underwear. I whispered loudly in protest, “no, I promised you I wouldn’t!”

“Silly boy, it’s been six hours. I’m not drunk anymore.”

What happened next happened quickly - disappointingly quickly, for both of us. I couldn’t believe the sheer sensation of it all, though. Then it was over. After I cleaned up (both myself and the bed, which I finished on), despite knowing my performance was not up to par, I felt elated; Cloud Nine was nothing, this was like being on Cloud Twenty.

Holly, however, was not impressed or amused. “I think you should go home.”

THE WALK HOME WAS BITTERSWEET, partly because I was still reeling from the knowledge that I just had sex for the first time, and knowing I was probably never going to have it again after that unsatisfactory showing. I didn’t let the latter ruin my day, though. I spent most of that day in my bedroom, remembering every touch and feeling that happened from the night before (and the morning). I was no longer in the “V club”! I could finally be one of the men. And I was sure Holly would give me another chance, maybe even teach me how to be a better lover.

The next day I was with my best friend, Bill, who had himself been building a rather large crush on me, unbeknownst to me at the time. I decided we should stop by to see the girls, and Holly was outside, sitting on the steps in front of her apartment, looking rather sullen. I tried to talk to her but she kind of dismissed me. Courtney appeared in the doorway, asking me to come inside. I left Holly with Bill outside, since she was being friendly towards him, and followed Courtney inside.

I waved hello to Holly’s Dad, and proceeded to the bedroom with Courtney. She asked me if I wanted to join her and Holly on a trip to Six Flags Great Adventure sometime that week. Because of all the weirdness, I asked if it was okay to bring Bill; I didn't want to get stuck there for one thing, and then at least if things got too weird, I'd have him to just hang out with. She consented, we struck our plan, and I turned to go.

On my way out, Holly didn't even say goodbye.

OUR TRIP DAY CAME, AND I went down to the park with Bill, while Holly and Courtney drove down in Holly's yellow Saturn. We met at the park, and throughout this most awkward day, while Courtney seemed to be enjoying herself quite a bit, Holly was considerably bitchy. She refused to go on any rides with us, and was generally contrarian. Even though the three of us were all trying to stay positive, it was difficult to keep doing so when she was trying to bring us all down... and the worst part was, none of us really knew why. I tried being affectionate towards her, but she was cold.

Courtney, on the other hand, was being exceptionally flirtatious with me. She would take my by elbow a lot when she wanted me to go somewhere with her, and when she stood next to me, she would often press her body into me. She always smelled so good, and she was quite attractive, so I sure wasn't complaining. Besides, Holly didn't really seem to be all that interested in talking to me anymore.

At one point, Bill and I were off by ourselves for a few minute, enjoying a cigarette and a soda. Holly and Courtney approached us. Holly stepped right up to me, and said, rather unemotionally, "I'm tired. I want to go home. See you."

And with that, she turned on her heel, and walked away. Courtney lingered for just a moment. "I'll call you tomorrow," she said, and they walked off into the sunset, leaving Bill and I alone for the rest of the day.

I DIDN'T SEE HOLLY FOR about a month after that day. Courtney and I had been seeing a lot of each other (perhaps a story for another day), but Holly would always be absent whenever I visited Courtney. We usually spent time at my place when my dad was away, anyway.

One day, while walking through the apartment complex, her yellow Saturn pulled up a few dozen yards away me. She rolled down her window, and tossed a half-finished cigarette out of it, before calling me over to her. I considered ignoring her for just a moment, but after a brief hesitation, I figured it was just as well to say hello, so I ambled over to her.

"How are you?" she asked, rather cheerily. I looked down at her in the car. She was dressed in all black, with a sleeveless blouse and a short black skirt that, while seated, showed off her stunning legs. I was still a little leery, but I attempted a smile, saying, "I'm pretty good. How are you?"

She looked at me in a way that I can only describe as hopeful. "I'm moving back to Texas. I... miss home. A lot." She looked down at the steering wheel, drumming it with her thumbs, and then looked at me again with that hopeful look, as though she believed that going back home would solve her problems. I said, "well, Holly... I wish you luck."

"Will you miss me?" she asked, with a fake southern drawl and her mischievous smile. Contained in that smile was all the personality, flirtatiousness, and pure sexiness that sucked me into her crazy world to begin with. For just a second, it was tempting to allow myself to fall for it again, but I wasn't ready to step back in that world again.

"I already do," I said, smiling back. A small part of me even meant it.