Cheryl

A coming of age story with a cool twist. 

 Published in The Wordsmyth, June 2025

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Cheryl by Damon Yeargame. It was a big day for us. A big, big day. I lay on top of the sheets, my double breasted suit, cumber bun, bow tie, and cufflinks tossed onto a chair, or near enough for me. I had my tee shirt and pants still on. The latter she liked to take off herself. It was a big day. It would be an even bigger night. She was in the bathroom getting ready. What would it be? A teddy, a costume, or maybe she'll just come out naked and jump on top of me. I smiled, stuffing another pillow under my head. How happy the world had become. Joy was now the norm. The expected result. Our light motif. It was such a contrast from the way things used to be. My body grew numb and the room spun a little. Tonight was the first time in a long time I'd had anything to drink. Maybe I should have stopped after the second glass of champagne. I closed my eyes not to sleep, just to rest. Rest a bit until she's ready. A memory comes to me, floating through my tired brain in fragmented pieces. The woods a sultry night. A girl. I force my eyes open, need to stay awake. I glanced at the nightstand. The hotel had neatly stacked the remote beside the channel guide. Music was offered through the TV and I flipped through the options until I found something romantic. Tomorrow we'd be on a beach in Hawaii. I raised an invisible glass towards the bathroom. Here's to a big day, a bigger night, and a long life together. May we be banging each other's brains out for many years to come. My eyes grew heavy. Again the memory calls to me, calls me back from so many years ago. How many? Ten? Holy Jesus, has it been that long since Cheryl? I remember going to bed early that night and was sound asleep when a loud thwack jolted me awake. In a single bound I was at the window. I threw it open. Hey Tommy, wanna come out and play? A voice giggled from the dark. Cheryl. I guess there was a reason my parents didn't like her. It's after midnight, I whispered back. Are you gonna turn into a pumpkin? she asked. I have finals tomorrow. If I fail I won't be in eleventh grade next year. Eleventh grade is overrated, she answered. Besides, you always ace those things anyway. Probably because I'm usually asleep at this hour. That's what I thought anyway. What I sighed was let me throw on some clothes. It was useless to argue with her. She always got me to do those things I would never do on my own. Cheryl was a year older than me, and cool. Just to be seen with her elevated me in the eyes of everyone at Wayne High. Back then I was in desperate need of a self esteem boost. I dug through the pile of clothes Mom had been stacking on my dresser all week. She said that by tenth grade I should be able to put my own clothes away. Clearly the parenting advice columns were working to perfection. It took some effort, but I think I found the right combo of shorts, shirt, and underwear. My shoes were downstairs, and not wanting to risk waking anyone up, I slid on my flip flops. As to whether anything matched, let's just say it was good it was dark, and Cheryl was the one girl who wasn't obsessed with fashion. I crawled out of my bedroom window. Our house was two stories tall. The garage a single story sat right next to my room, making it an easy hop onto its roof. I then grabbed the rope I'd tied to a post on the side of the house, one I knew could hold my weight, and tossed it over the edge of the garage. I'd use it to climb back up later. I squinted down at the black lawn below. Even though the jump had become almost routine, I'd only done it a few times in the dark, usually on nights when Cheryl wanted to take a late night walk and talk about whatever. Mostly she spent the time making lewd comments about the popular kids. My heart was racing. Every other time I'd made this jump I was wearing shoes. This time I had on flip flops. I wasn't sure how well that would go or how I'd explain a broken ankle to my parents. I took a deep breath and jumped into the void. No sooner had I hit the ground, performing a tuck and roll as I did, when Cheryl shoved a pillow in my chest. Let's go, she said. Where are we going? I asked. To sleep in the woods. But I don't have my sleeping bag, I protested. You're so innocent, she laughed, grabbing my hand. My sleeping bag is a double. Oh, I answered. Oh yeah, is what I thought. As she practically pulled me down the street towards the forest, I repeated to myself over and over again, I'm gonna get laid, I'm gonna get laid, I'm gonna get laid. At the height of my revelry, I was struck with a far more important, wider reaching dilemma, one that could emotionally scar me well into adulthood. I remembered watching this movie where a guy got a cramp in the middle of doing it. What if that happened to me? Oh God, what if I can't do it? Cheryl had lots of friends. It was sure to get around. I could see Bobby and Flip laughing at me. How come you're so quiet? Cheryl asked, interrupting my despair. Still a little groggy, I answered. Well, you better wake up. We'll be in the woods in a couple of minutes. Wearing flip flops had definitely been a mistake. I kept having to stop and shake out tiny stones that got wedged under my feet. Then we wandered off the path into weeds full of sharp, spiky burrs. I yelped. Cheryl apologized, then pulled a flashlight out of her purse and clicked it on. She slipped her arm around me and helped guide me out of the brush and back onto the dirt path. She, of course, had little trouble with the stones or stickers because she wore the same ratty combat boots she always wore. They were a perfect compliment to her cut off shorts and torn safety pinned sex pistols tank top. She was one of the most sought after girls in high school, and not just because of her boobs. Her hair flew in every which way, landing wherever it damn well pleased, as if in flagrant protest against all rules and conformity. Cheryl didn't care about anything, or so I thought, not about the bugs or the spiders in the woods, not about her parents, and certainly not about how others perceived her. While the rest of us, especially me, worried about everything, what others thought, how I looked, not being able to do it, and the wrath of my parents if I got caught on this little excursion. Cheryl had the freedom the rest of us lacked. It made her damn hot. When we reached her chosen spot, she spread her sleeping bag on the ground. I tossed the pillow on top, then lingered there as if mesmerized by the forest. She had chosen me, a tenth grader, a geek, and I didn't have a frickin' clue what I was supposed to do next. She laughed and slipped into her sleeping bag. Articles of clothing came flying out, boots, shirts, shorts. I stood there, frozen, wondering if she was wearing any underwear. This will lighten the mood, she said, pulling a bottle out of the sleeping bag. The plastic seal cracked as she twisted the top. At least my dad is good for something, she muttered, taking a big swig. She handed the bottle to me. I held it in my hand for a long moment. The dark, shadowy woods made the liquid look black. I had the feeling of being in line at some crazy ride your friends talked you into, not really wanting to go, but too afraid of what they'd say if you backed down. I slowly lifted the bottle to my lips. What I thought was a small sip burned like fire going down my throat. I choked. Cheryl laughed. You getting in or what? I pulled off my shirt and fumbled my way in. I kissed her, or probably more accurately, I pecked her the way you would with your aunt or grandma. She laughed and yanked off my pants, and then put her arm around me. I was astonished by the warm softness of her skin. I tried to mimic the way she moved her tongue around the inside of my mouth. I had thoughts about moving my hand elsewhere towards well, you know. I would have gotten there eventually too, except she suddenly dropped her head onto my chest. At first I thought she was laughing. Then I felt moisture pooling up on my torso. When you go off to college her voice cracked. Do you think we'll still be friends? Of course, I stammered. Why? I don't know. People Mom How can they be so? She stopped and rolled away from me. I became conscious of the sounds of the forest, cicadas, crickets, and a critter rustling in the leaves. Above me the faint outline of clouds drifted, grey, shapeless forms with no beginning, no end, no purpose. They simply hung there, drifting aimlessly with the wind. Dad came home drunk again, she said finally, turning back towards me. Not that I care about that, she continued. He's a halfway nice guy when he's had a few. But Mom was screaming at him. I went upstairs to her room, I don't know why, I guess I just wanted to escape. I grabbed her red nail polish. I don't even like nail polish, it's so fake. I didn't notice the screaming stopped, Cheryl continued. I hadn't noticed Mom was standing beside me. She cleared her throat and the sound startled me and I dropped the bottle. It shattered into a thousand pieces. She then bent over and swirled her fingers in the red polish. Hunched over like that she looked like a shell shocked old lady from one of those war films they make us watch in history class. A refugee rummaging through the pieces of her broken, battered, bombed out shit. It was a fucking five dollar bottle of nail polish I told her I'd buy a new one. Cheryl paused, nervously tugging at the zipper of her sleeping bag. Up and down it went, a little more forcefully with each iteration. Then with a final violent jerk, she zipped it all the way up and tucked part of her face beneath the fabric. In the moonlight I could see the reflection of her tears. Then Mom stuck her hand in my face, like two inches from my nose. Cheryl's voice was low. Red drops were dripping off her fingers. It was freaky. I couldn't tell if it was nail polish or if she'd cut herself on the glass. Maybe it was the drink or the night, but listening to Cheryl, I felt hyper aware of the moment. I'd dreamed of being with her countless times, and now I could see the faint outline of her naked breast under the sleeping bag. But there was nothing sensual about it. Instead I had a heightened sense of the expression on her face. And it didn't seem like her. Cheryl always made light of things. She cracked a snarky joke or said something wildly inappropriate that got everyone around her to laugh. Now there was no humor, only a face etched in pain. And then Mom Cheryl choked on the words. Mom said this is why your dad drinks. Then she hunched over the dresser and whimpered You work, you sacrifice and what do you get? Cheryl pressed her head into my chest again. She didn't speak for a long time. Finally, in a whisper she said I made him do it. That's what my mom said. He wanted to have an abortion, but I made him have you. I got the hell out of there, Cheryl said. I had to get out. I wish I were older, I wish I had money. I wish I could go away for good and never come back. She rubbed her hand against my stomach. I'm sorry I made you listen to my fucked up family shit. I didn't answer. The details were different, but I understood. It was a common misconception then and probably now, to think that kids doing well academically all have stable homes with squared away parents. Experience has taught me otherwise. Dirt is easy to find if that's what you choose to go looking for. Still, I didn't know what to say. To Cheryl, until that moment I think I'd always been the nerdy sidekick, but this girl, this bold, rebellious girl, was now vulnerable and afraid. She needed someone to be strong. Yet I couldn't find a way to console her. Instead, I lightly stroked my hands through her hair while she nestled her head into my shoulder. It wasn't until years later that I realized it was exactly what she needed. We woke up the following morning to the sound of a bus, a bus we'd already missed. Luckily, we only lived two miles from the school, basically a warm up run in track. Unfortunately, Cheryl didn't run track. I had to coax her into walking fast. There were several large hills close to the school, and Cheryl couldn't keep up. I grabbed her hand and gently pulled her along. She was out of breath when we reached the crest of the last hill. We could see Wayne High below. Yes, I said once she'd caught her breath. Yes what? Cheryl asked. Yes. I will always be your friend. She grabbed me and kissed me. The moment was short, too short, as it turned out, but we had to keep moving if we wanted to make it to the next grade. I only ended up missing twenty minutes of my first final. I didn't ace it, but I didn't fail, and I somehow managed to pull off a B in the class. My parents left for work really early that morning and they never found out I'd almost slept through my exam. The last of the finals were two days later. Even though we really hadn't done anything besides sleep semi naked to each other, Cheryl didn't do anything to dispel the rumors that were flying around. In fact, she encouraged them. Oh yes, she told a group of girls. Tommy and I slept together in the woods. The rumor boosted my stature throughout school. Girls who I didn't think knew my name began talking to me. I didn't see much of Cheryl over the summer, though. She ran away, only not from home. She started drinking heavily and then graduated into harder drugs. She ran herself into an addiction. Still, I kept my word. By the time I finished high school I had a completely different set of friends, but Cheryl was always there. When I went to college, I visited her once a month at whatever halfway house or treatment center she'd landed in. It was all very platonic in those days. We played cards and walked the grounds. She said those visits were what kept her going. She especially liked stories about my life and success, not my success at school or eventual career, she said those were expected, but the way I grew socially, the way I interacted with others and with women. She watched me evolve and it gave her hope, something to shoot for, a concrete example that self confidence was more than just rebelling for rebellion's sake. It could be built from within. Everything had its roots in that night. Before then I always felt like a dweeby kid, not deserving of anything, especially not attention from the opposite sex. Women to me were like rare, beautiful artworks, admired only from a distance. Cheryl knew what I meant. She'd been with guys, but they'd only wanted her for her body. No one cared who she was underneath, not even her parents. I was the first person, she said, who liked her for her. Years passed, recovery was uneven, but we stayed connected. Calls, letters, visits. We didn't realize it at the time, but we'd become invested in each other's souls. The return on that investment wasn't paid in dollars, but in dividends of something far deeper. She came out of the bathroom wearing cut off shorts, a t shirt layered under a sex pistol's tank top, ratty combat boots, and the veil she'd worn earlier today. She was carrying a double sleeping bag which she tossed onto the bed. She jumped into it, and clothes came flying out. I wondered if she was wearing any underwear. Well, big boy, Cheryl said, are you just gonna sit there with your mouth hanging open like a smitten tenth grader? Or are you gonna hop in and make a love to your wife?