My Freaky Senior Prom

All characters are over the age of 18 at the time of any sexual activity.

This is my entry for the April Fools Day Story Contest 2024. I'd already been writing it when I read about the theme, and it just fit.

A twist on 'Freaky Friday' with a bit of '10 Things I Hate About You', this is a story about a couple of adorably overachieving, but under-experienced high school seniors. These 'frenemies' get an unexpected shock on the morning of their shared eighteenth birthdays, which you can probably guess. Of course the story revolves around the week leading up to prom, because what has more delicious high school drama than prom? As you'd expect, the characters are forced to grudgingly but temporarily experience life the opposite gender. If that offends you or isn't your thing, this tale probably isn't for you.

This one is a bit of a slow burn, but is sprinkled with some spicy bits to keep things interesting before the tantalizing will-they-wont-they ending.

* * *

This is one of those stories that most people won't believe. Hell, I wouldn't. Honestly, I can still hardly believe it even today, and it happened to me. This was almost exactly six months ago, and holy shit... what a six months. The interesting parts all happen in the first week or two, so maybe I'll start there. It's gonna take me a couple hours to unpack my stuff into my new dorm room anyway, so I have some time.

I should probably start with a little backstory, because it's pretty important to help understand the things that went down.

My name is Theodore Harper. Theodore was my grandpa's middle name, and is objectively horrible. I have no idea why I couldn't have his first name, William. I coulda been Will, Bill, Billy, or even stuck with the admittedly classy William. But no, Theodore. Thank god one of my best friends in kindergarten couldn't pronounce it right, so my dad offered Theo as an alternative. It seemed to stick, and Theo, I could live with.

I was what most of my teachers called a good kid. I always tried hard in school and got good grades. My parents encouraged me to do sports from an early age, and I just seemed to be good at all of them. Both my folks were college athletes from like a hundred years ago, so I supposed I had some of their good genetics to thank.

I knew a lot of my peers saw me as that guy. Smart enough to keep a four-point, good at sports, reasonably attractive. I know, I would have probably hated me too. Somehow though, I got along with everybody. Well, almost. We'll talk about that in a minute. I could walk into nearly any group of people and feel comfortable. People my age, younger, older, my parents friends... it didn't seem to matter. My mom called me an old soul, which for a long time, I had no idea what that meant.

I grew to an even six foot by the end of sophomore year, which was great for basketball and track, the two sports I settled on pursuing into high school. I got my dad's thick, wavy blonde hair, and my mom's fine features. I spent at least a little time most days in the gym, purely for fitness and performance in my sports... but I knew it helped my body. I liked what I looked like in the mirror, nothing wrong with admitting it. Between strength training for basketball and careful eating and cardio for running, I looked good.

The one part of the old soul nonsense I did understand was dating. Or should I say, lack thereof. I had all the normal hormones and urges of any guy my age, but holy shit... girls were by and large, completely bat-shit crazy. The constant drama, bickering, backstabbing, jealousy, I honestly couldn't fathom devoting enough brainpower to try and date, let alone have a girlfriend.

By junior year though, I finally succumbed to the steady stream of girls throwing not-so-subtle hints at me, and went on a few dates. Yeah, I know... poor me. A couple of them were alright. I even had a really nice first kiss that turned into a pretty steamy makeout session in the back of a movie theater. But of course, the next day at school was all the whispering, giggling, and pointing. It just wasn't worth it.

Hang on, I went too far ahead. Gotta back up. Like... way up. I can't really tell the rest of the story without her, so here goes.

Lily Whitlock.

Just saying her name forces an emotional response, but for different reasons now than then.

Lily and I have lived three blocks apart since we were born. We learned early on in kindergarten that we shared a birthday. It was kinda fun at first, finding someone who you could be excited with about the same thing that you happened to have in common. By the time our sixth birthdays came around though, our relationship had changed radically.

To say a first grader could have an arch nemesis is probably a bit dramatic, but that's how I saw it then. Not less than five times that year, both sets of parents were called to the school to deal with some kind of issue between us. We were never overtly hostile or wanting to cause the other harm, but to say we competed with each other would have been a gross understatement. Any game or assignment that could have a winner and a loser... we would take it too far, and then a couple steps beyond.

Even the moms got in on it. Two sets of birthday cupcakes on the same day... who went to the better grocery store? Who brought Capri Suns instead of a gallon of juice and paper cups? It was a thing. I don't even want to get into the great third grade Chuck E. Cheese birthday party double-booking fiasco.

As soon as I understood April Fool's Day, I simply assumed that it was in fact, some kind of cosmic joke that we'd been born together on that particular date.

By the time I got to fifth grade, I'd begun to realize it was the fact that we were so similar that caused the friction. I even overheard some of our teachers calling us the twins, which I'm sure started with our shared birthday, but then got reinforced by personalities that were simply too alike for there to be two of us.

I reached a new level of self-awareness in middle school, and it genuinely began to bother me. Me, the guy who got along with everyone, and yet somehow just couldn't seem to accept Lily as her own person that could have a life and success and happiness outside whatever contest we were engaged in. I made a conscious effort to be nice to her, but god it was hard. By the end of eighth grade we were squarely in the frenemy zone. Our lives overlapped in so many ways... nearly every class, student government, track and cross country. Our paths crossed every day. She truly felt like the irritatingly pretty, smart, and bitingly clever yin to my calm, collected, and popular yang.

Lily's growth spurt came the summer before high school. She shot up to five foot nine, which for the first half of freshman year, she loved to hold over my head. She could, because she was literally taller than me and pointed it out nearly every day. I got so frustrated one day that I said something horrible about her being stick straight and flat as a board. The handful of her friends that overheard my comment giggled, and I actually felt bad. Not that I let her know that or apologized, of course. The universe immediately responded, as it tends to do. I remember quite vividly watching her walk up the front steps the first day of Sophomore year. Lily got curves. It pained me to stare... her hips had filled out, and her chest was graced with a perfectly proportioned set of breasts that stretched her sweater out, oh so perfectly. Her face had always been beautiful, now she had the body to go with it. She'd even grown out her chestnut brown hair to fall gracefully over her shoulders.

I was briefly a half-step away from thinking of her very differently. Lily was the one of the few people I knew that when we weren't arguing about something, could carry on an intelligent conversation without descending into gossip or other high school drama. We had so much history that there could have been some kind of base, a starting point to build on... but then she got hot. The new Lily suddenly commanded respect and attention and popularity. She still managed to succeed at everything, but now she looked fantastic doing it and had people cheering her on.

I never talked with her about it, but she seemed to be in a similar mindset about dating and relationships. There weren't many guys who could keep up with her whip-smart mouth or the fact that she could probably beat them at any activity. Add the fact that she was stunningly beautiful...

Our sometimes less-than-friendly competition ramped up again after that. We consistently jockeyed for the number one and number two spot in the class, and fought like siblings at any extracurriculars we were at together. She won ASB president our sophomore year, I won it junior. We both ran track and cross country, thank god our genders made it so we didn't directly compete.

By senior year, we settled into something like a cold war. With college in sight, I think we both knew that our competition was nearing an end. I'd come to peace with the fact that one of us would be valedictorian, the other salutatorian. We'd both give speeches and get awkward applause from our friends and family. Both of us had our sights on winning our cross-country district events, maybe even regionals. We had multiple college admissions to choose from as spring rolled around. Things were going to work out just fine.

Alright, enough background I think. Yada yada, my life was pretty amazing. I had a bright future ahead, and despite my halfhearted efforts, Lily Whitlock was still frenemy number one. The real story starts on March thirty-first of my senior year, or the day before my— our eighteenth birthday.

* * * * * * *

"I won't be out late, I promise."

"You'd better not be," she said back with a top-shelf mom glare. "Everyone is coming tomorrow for your party and I don't want you all tired. Or hungover."

"I know, mom..." I rolled my eyes dramatically. "It's just a little party, and it'll probably be lame anyway."

"It's your eighteenth birthday! You'll be an adult? It is a big deal, Theodore."

I made a low growl and glared back at her. "So does that mean all the rules get relaxed tomorrow then?"

"Oh, sweetie... no. Listen, have you made up your mind about prom yet? It's a week from today, remember?"

"Jeez, are we really gonna do this again? I said I'd let you know."

"Honey, it's your senior prom! You can't just not go..."

The truth was, I did want to go. I'd even picked a couple of girls I could reasonably expect to tolerate for a whole evening. Neither of them were slutty, which would take some pressure off the after party. I really just wanted to dance and have a good time. Make the societally-sanctioned high school memories and get on with our lives. That was the plan. So of course, they all got dates before I asked.

"Maybe I'll go stag... just go ahead and rent the damn tuxedo."

"Language! What's gotten into you?" She took my empty plate and walked it to the sink.

"I'm almost an adult, mother, remember?" I tried to suppress a grin.

"Be that as it may," she smirked, "if you slip up and curse in front of your grandma Helen tomorrow, you'll get an earful. Oh, and please go by and get your hair cut? It would be great if this shaggy mess looked a little better for pictures."

"Jeez mom, I like it like this. It's how everybody wears their hair now, okay?"

"Don't be so sensitive. I'm just talking a trim."

I humphed and refused to agree to anything. "I'm out. See you after school."

I gathered my things and left. The spring sun had wiped the dew off everything and my car was already warm inside.

Pulling in to my usual parking spot, I glanced up at the dull cinder block building and had a brief swell of contentment. My high school career was amazing, and more importantly, almost done. Both very good things. I'd be a legal adult in less than twenty four hours, maybe find a date to prom today, and then finish out the year with an eye toward my choice of universities. Things are gonna work out just fine.

I found my group of usual suspects friends huddled in the courtyard. I pushed my way into the circle and listened to the current story. One of the guys had just shot his shot with a girl way out of his league and had been rejected pretty hard. The rest of them were doing a piss poor job trying to console him, so I stepped in.

"Adam, dude..." I said, pulling him aside as we walked to class. "Prom isn't about who you go with, it's a right of passage. Don't worry about getting the hottest girl that'll say yes, find somebody fun. Have a good time, dance like an idiot, make everyone else wonder how you're having a better time than they are."

He laughed and clapped me on the back. "Man, Theo... you're so wise. Hang on, you don't have a date yet either, right?" Adam flashed me a grin.

"It's still a work in progress."

"I see. So... fun girl. Any ideas for me? I'm kinda gettin' desperate. My mom is all up my ass about dinner reservations and tuxedo rentals."

"Tell me about it. Alright, prospects..." I stopped in the middle of the busy hallway and cued up my mental roster. Despite not being overly interested in ever changing landscape of high school hookups, it wasn't that I didn't pay attention. I scanned the crowd and spied an obvious choice.

"You really ready to do this?" He nodded back. "Come on then." I crossed to the opposite side where a girl with sandy blonde hair was trying to convince her locker to open. She was a foot shorter than me, but pretty.

"Chrissy, hey!"

"Hi Theo," she said brightly.

I gave a carefully aimed side-fist to her locker door and it popped open. "Adam here has recently decided he'd like to go to the prom. Katie G told me you'd been considering it as well. I'm seeing an opportunity for you two here... go together, casually of course, have a freakin' great time. I bet Adam would even take you out for a nice meal."

"Oh yeah, totally," he nodded eagerly.

"Well," said Chrissy, "I did wanna go, and it seems like I might have waited till the last minute."

"See? It's perfect. You two work out the details and make it official. I'll see you there... and save me a dance!"

I waved and left, watching the wide smile turn her mouth up. Adam turned around and mouthed thank you. Alright, I thought as I made my way to calculus, now just take your own damn advice.

I devoted a reasonable amount of brainpower that day to evaluating my options. A couple of promising choices presented themselves, but my discrete text queries and insta sleuthing quickly shut them down. One of the girls had a date already, and the other was going to be out of town. Maybe the party tonight will be better hunting? Yeah, I thought dejectedly, one week before... anyone left will be some kind of mutant or serial man-eater. Why did I have to wait so long?

Classes were at least easy on Friday. Most of the teachers had mentally checked out, and for the seniors, we were pretty much on auto pilot. I even got a text before last period that our cross country practice had been cancelled, which I was honestly okay with.

I busted out of the door of my computer science class, very ready to start the weekend. Not only was it Friday, but today was my last day of being seventeen. Adulthood and freedom in sight... I actually had an introspective moment about it as I walked down the hall. That was, until she sidled up to me.

"Hey," said Lily. "Happy birthday eve."

"Is that even a thing?"

She snorted and glared at me. "Of course it's a thing. This is the day before our birthday, hence... eve."

"I know what eve means."

She shook her head and kept walking with me. "So you going to Jessica's party tonight?"

"Yeah, probably," I said, lobbing her a curious glance. "Wait, are you?"

"Thinking about it, it'll be the last party we go to as kids. That, and my folks have the rest of the weekend destroyed with birthday and family bullshit."

"Yeah, I hear that. I guess maybe see you there." I had an intrusive thought and almost asked if she was going to prom. My logic center quickly reeled that back. I am not gonna risk that question getting taken the wrong way. Besides, we have districts the next Monday. No way she'll do any partying that weekend.

She arched an eyebrow and flashed me a look I'd seen thousands of times. "Fine."

I shook my head and split off to the parking lot. I got home and found a big note on the fridge reminding me to go in for my tuxedo fitting. I was ready to hop back in the car and go, but got a text from some friends who had arranged a Fortnite tourney that was going to back up against the party tonight. Hmm, lemme think... My buddy Dax sent me three messages in a row demanding I come help their team win with my sick skillz. I called the tux shop on the way and made an appointment for first thing the next morning instead.

The tournament was legitimately off the hook. We had twelve PS5s in somebody's basement and enough Rockstar to fill a bathtub. Our team narrowly won, my one in a million sniper shot taking out our last competition at the end. The whole room erupted when I made the kill, and Dax tried to lift me onto his shoulders. He's not a big guy, and we ended up crashing into the amber shag carpet and descending into hysterics.

Darkness had long since fallen when trudged out of whoever's house we were at. I drove home, glad to find my parents out to dinner or otherwise not there. I slipped inside to put on a nice shirt and grab a jacket, then made the short walk to Jessica's.

I could hear the music when I got close. Her house was infamous for parties and other less than upstanding events. Jessica's mom traveled all the time for work, and seemed content to buy her daughter's approval with few rules and a well-stocked liquor cabinet.

There were already quite a few people there when I walked in. A couple of my buddies had arrived and were playing beer pong. They good-naturedly shooed me away from the table, knowing my talent for sports involving balls somehow extended to party games too.

I mingled around and got hellos out of the way. I made sure to find Jessica and thank her for hosting. She was wearing a dress that looked more like some kind bathing suit, but who was I to judge. It was her house after all. Her barely covered tits pressed into my chest as she hugged me and gushed thanks for me showing up. Already pretty tossed... at eight thirty. It was a good mental reminder for me not to drink much. I obviously didn't want to be hung over at my own birthday party, but more importantly, if I showed up at home with even a trace of booze on my breath, my mom would smell it like a bloodhound. Thanks, just a beer, I said to her as she steered me toward the table covered with bottles.

I wandered through the party, chatting and generally having a good time. The cross-section of people was pretty good, but tending toward seniors who were getting early cases of summer-itis. About half the football team's offensive line was out in the backyard tossing a ball. I shouted at one of them from the door and caught a long pass from the opposite side of the grass. Much cheering. I tossed it back and made the rounds out there. I'd just come back in for a water when the front door opened. I knew it would happen, but it twisted my mouth into an involuntary sneer.