How far would you go to help make your best friend's ex-girlfriend jealous?
|Sometimes, the most important moments in your life can be born from the smallest, most insignificant events. Take, for example, a man bumping into a woman in the hallway of their apartment building, after some apologies and helping to pick up dropped items, it can lead to the two having dinner together, and then lunch, and then dinner again and you skip ahead forty years to find an old married couple with seven grandchildren and one on the way. The cause of the most important moment in my life started out pretty mundane, while I hung out at the mall with my best friend, Billy.
I was trying my best with Billy, but I could tell he was only smiling to make me feel better, which is ironic because the reason we were hanging out at the mall was because I was trying to make him feel better. Melissa Miller, his girlfriend of a year and a half had just broken up with him, two weeks before prom and he wasn’t taking it very well. In fairness, neither would I, especially since it happened with the one-two punch that she’d also been cheating on him with the quarterback of the football team, and now she was breaking up with Billy so she could be with the quarterback full-time and be his prom date, and a shoo-in for Prom Queen.
“I can’t believe that bitch would do that to you…” I’d said when he called me, nearly in tears, after she’d dumped him.
“Don’t call her that, Jensen! Yeah, she did a bad thing, but there’s no reason to demean her like that…” Billy admonished.
“She should be demeaned! Humiliated for what she did to you!” I shouted over the phone.
“Just drop it okay, I don’t wanna talk about it anymore…” Billy sighed.
So a nice trip to the mall to visit the old arcade or the games store was just what the doctor ordered. As we were finishing up our lunch, I continued my quest to take Billy’s mind off the breakup.
“Oh! I almost forgot, did you catch that new episode of ‘Cosmic Expedition’ last night?” I asked.
“No, I haven’t really been in the mood to watch it, cause of you know…” Billy trailed off.
Shoot! That’s right, the show’s two romantic leads were in a pretty tight relationship. Can’t say I’d want to watch something depicting lovebirds in that state either… It was at that point that I stepped away to use the bathroom, and the moment I’ve been setting up happened, I wasn’t there, obviously, but this is how it was related to me by Billy. As I walked away, Billy heard a precise and familiar clicking of heels, and when he turned around to investigate the sound, he found Melissa, looking as pretty as ever (hey, his words not mine), standing in front of him with her hands on her hips.
“I can’t believe you!” Melissa exclaimed.
“You can’t believe what?” Billy replied.
“Don’t give me that innocent act, I saw you with that… slut! We’ve been broken up for three days and you’re already with some other girl?”
“I have no idea what you’re talking about, ‘Liss. And besides, you broke up with me for another guy! Why do you care what I’m doing or who I spend it with?”
“You know what? I don’t even care that you’ve already given that tramp one of your hoodies, cause Josh is twice the man you ever were!” Melissa snapped.
It was at this point, especially with the last comment about the hoodie, that Billy realized what the hell she was talking about. The “tramp” she was so angry about... was me. And I suppose I should explain why she’d think that, you see, I’m fairly short for my age (made worse standing next to Billy who was pretty tall for his), wasn’t blessed by puberty with a lot of body hair, particularly facial hair, and I liked to keep my hair pretty long, trying to emulate celebrities like Keanu Reeves and Adam Driver, so combining all that with the seething jealousy of a girl who thought she was the only one with a new relationship and the fact that thanks to an unfortunately timed ketchup squirt, Billy had graciously offered me his hoodie to cover up the obvious stain on my shirt, I apparently looked an awful lot like a girl.
“Listen, you’ve got it all wrong…” Billy tried to explain, stifling a chuckle. “That ‘slut’ is actually…”
“I don’t want to hear it! But if you decide to bring her to prom, stay away from me and Josh!” Melissa shouted.
Instead of continuing the argument, which he figured would be fruitless, Billy decided to let her leave, and with an “Ugh!”, Melissa turned on her heel and stormed off.
When Billy told me what had happened, frankly, I was pretty offended by the whole situation. After all, I spend a lot of time trying to accentuate my masculinity, but apparently, even to a girl that I’ve gone to school with since we were little kids, I look like a girl! Billy, however, found it absolutely hilarious, and when I got back from the bathroom, he was laughing the hardest I’d seen him laugh since the time one of our Chemistry subs accidentally scorched the chalkboard when his tie got caught on the bunsen burner.
“What’s so funny?” I asked.
“I just saw Melissa,” Billy replied, wiping a tear of laughter from his eye.
“And you’re laughing about it?” I asked with genuine concern on my face. “Are you okay?”
“She… she… Ahahaha! I can’t even say it, it’s so funny!” Billy tried to regain his composure.
Once he managed that, he relayed the story to me just as I relayed it to you, and while he continued laughing, my face was redder than the ketchup stain on my shirt.
“Me? A girl? Do I look like a girl?” I asked, searching my reflection in a metal tray for signs of femininity.
“To me? No, but with the hair, and the fact that you’re swimming in my hoodie probably didn’t make it that obvious. But isn’t it hilarious? She thinks I’m over her and it’s bothering her! She even asked if I was bringing you to prom!” Billy descended back into a fit of laughter.
“That’s it, at prom, you stay far away from me! I don’t want anyone else thinking I’m your date!” I quickly ripped off the hoodie and tossed it at Billy.
“Relax, it’s just a misunderstanding, a really funny misunderstanding, and she didn’t even realize it was you anyway! The only people who know about this are the two of us… and maybe anyone Melissa tells, but no one else will be dumb enough to believe you’re a girl!”
“Yeah, right…” I hoped she wouldn’t realize too late her mistake and tell everyone, or worse, come back and realize it in front of me. “Why don’t we head out? It’s getting late.”
“Come on, don’t let that ruin the day. I mean, it’s the least I can do to offer to take my… girlfriend shopping!” Billy continued laughing.
“Shut it!” I gritted my teeth and turned away from him.
“Okay, okay, I’ll stop, I promise! But wouldn’t that be something, showing up to prom with my best friend on my arm and a jealous ex across the dance floor…” Billy quickly regained his composure and put his hand on my shoulder. “Come on, let’s go.”
With Billy sufficiently cheered up at my expense, we parted ways and headed to our respective homes. As I tried to forget about what had happened, I was inundated by more jokes and pictures from Billy regarding Melissa’s mistake, so I turned my phone off. I should probably explain that Melissa was one of the hottest girls in school, blonde and well-endowed, and while she wasn’t head cheerleader, she certainly acted like she was the queen bee. A lot of people were surprised when she decided to date Billy, they’d hit it off when he’d tutored her and she seemed to really like him. At least until now.
Anyway, then I decided to troll social media, but with prom frenzy being in full swing, all the various posts from girls in our class didn’t make for the best scrolling experience, so I ended up just lying on my bed staring at the ceiling until dinner.
The next day, which was Monday, we were all back at school, thankfully Billy had seemed to calm down with his jokes and everything seemed back to normal, save for Melissa being even more overly amorous with Josh in the hallways whenever she thought Billy would be watching. She deserved to be taken down a peg, but I didn’t have any ideas as to how to do it. But as I found out a few days later, Billy did.
“You’re joking!” I slammed my locker in frustration. “I told you to stop it with those cracks!”
“It’s not a crack! It’s revenge! Living well is the best revenge, right? So if I had a cute prom date and we had more fun than her, then she’d have a miserable prom and the only person she can blame is herself!” Billy said.
“So find a girl to go with! I’m sure there are some girls left who need dates.” I said.
In fact, I knew there weren’t many, a lot of the girls I knew weren’t even going to prom and those that were had strangely high standards. I’d spent the last few days trying to find a girl who’d go with me to prom if only to assuage my fears of being seen as Billy’s date since we’d both be going stag otherwise. But of the girls I’d asked, the common denominator was a big fat “No”. Even given his recent breakup and the pity that there’d surely be, I didn’t imagine Billy would fare much better, even if he was the better-looking one between us. Especially since no girl in their right mind would want to incur Melissa’s wrath, even if it was just for a few more weeks before graduation.
“A girl didn’t make her jealous. You did.” Billy whispered. “Anyone ever told you that you’re cute when you’re angry?”
“Don’t call me cute!” I pushed Billy away and started heading towards the exit.
“I’ve given it some thought, I’ve already booked the limo, so we ride in style either way. But this way, Melissa gets her just desserts.” Billy rushed to catch up with me.
“What about me? I’d love to see her miserable after what she did to you, but what if people realize who I am? What if Melissa does? She’ll ruin my life! The boy who wore a dress to prom! I’d never live it down!”
“Listen, in the first place, it’ll make her so jealous that if she figured it out, she’d never admit it! Can you imagine her telling people that a boy in a dress made her jealous? And secondly, if anyone realizes it’s you, I’m sure we can play it off as a prank on ‘Liss and everyone would understand. No need for embarrassment.”
The more I mulled over the idea in my head as we walked home, the more conflicted I felt. As a man, I should feel the entire suggestion as an affront to my identity, but a small part of me that wanted to make Melissa feel as bad as Billy had felt for three days kept poking its head up. And since it’s only weeks until graduation, how bad could any potential embarrassment be? Nothing from high school matters in college anyway. Especially since Billy and I were both going to the same out-of-state school, a fair distance from our hometown.
“Okay, let’s say I go along with this crazy scheme of yours. And I’m not agreeing to it just yet, but if I did! Where would I even get a dress? And I don’t know the first thing about hair and makeup!” I said.
“You have an older sister, just borrow something from her! She went to prom last year, didn’t she?” Billy remarked.
My mind flashed back to the turquoise taffeta dress that my older sister had worn at her prom the previous year. And I knew we were close to the same size in shoes, to both of our embarrassment, since we’d each borrowed whatever footwear was lying around from the other when we needed to rush to the mailbox in a hurry. But I still wasn’t sure about the whole idea, and in matters like this, one needs an outside opinion. So I decided to go to the person I trusted even more than my best friend, my older sister, Chloe, recently back after her first year up at college. After I got home, I went upstairs and found Chloe’s door ajar, knocking on it as I poked my head into the room.
“Hey, do you have a minute?” I asked.
“Hey, Jens, what’s up?” my sister asked, as she looked up from her phone.
“I’ve got a favor to ask,” I said.
“Anything for my brother. What’s the problem?”
“Promise you won’t laugh?”
“You know I can’t promise that. Especially if it’s funny.”
“Okay, so, when Billy and I were at the mall the other day...” I started.
I explained the situation to Chloe and to her credit, while she had to stifle a few giggles, she managed to make it to the end of the story without laughing. As she processed the story, I noticed her lips curling into a smile and rolled my eyes as she burst into raucous laughter.
“Ahahahahaha! That’s fantastic! Serves her right, too.” Chloe said. “And you really want to do it?”
“Not really, but I want to help Billy, and I think he needs a win more than I need my masculinity. What do you think?”
“I think it sounds like a really sweet thing to do,” Chloe said. “So what do you need from me?”
“I was hoping I could borrow your dress from your prom. And you could help me do my hair and makeup and stuff.”
“I can definitely help with the second part, but I can’t give you my dress.”
“Cause we’re not really the same size. You’re as thin as me, but you’re taller, so it’ll be even shorter on you than it was on me, and Mom wasn’t thrilled with how short it was when *I* wore it. Besides, it’s out of date, if you’re going for the full experience, you need a dress you picked out on your own. We’ll go shopping this weekend, and you can bring Billy along to help.”
“Shopping? But I’ll be seen!”
“Okay then, not as yourself. I’ll find some stuff in my closet for you to wear and you can go incognito. Better to look like a girl on purpose, right?”
And that was how I ended up at the mall the following Saturday wearing my sister’s denim skirt and a pink summer top, a pair of ballet flats, and a grimace of fear on my painted face. Despite the hard work my sister had put in, styling my hair expertly into a girl’s style, and using makeup to ensure that my face looked sufficiently feminine, my anxiety was still spiking. I licked my lips nervously and tasted the strawberry flavored gloss on my lips, while as I kept my legs crossed, as instructed by Chloe, I slightly chafed as my body got used to being free of all the hair that I’d managed to grow in all my years of puberty.
“Stop fiddling with that.” Chloe admonished me as I tried to once again adjust the bra strap digging into my shoulder.
“It’s not my fault, it keeps digging into me,” I whined. “Isn’t there anything you can do?”
“Unfortunately, because it’s stuffed, I have to make sure it’s on tight enough that nothing falls out. If they were real, we wouldn’t have that problem… But I might be able to fix that before prom night...”
I really didn’t want to know what she had in mind, so I changed the subject.
“And did I really need to wear a skirt?”
“Sorry, Jens, but if you’re going to be trying things on, you need something easy to get out of and all of my pants are too tight. Besides, if you’re gonna wear a dress, you’ll need practice in skirts.”
“I guess that’s fair…”
“I know this is all new to you, but it’ll get easier once you get some practice in. How’s your girl voice coming along?”
“What do you think?” I attempted to lighten my voice both in tone and pitch as Chloe pulled into a parking space.
Based on Chloe’s face as I spoke, I didn’t need to hear an answer. It still needed work.
“We can work on that too… But I’ll try to do most of the talking today.” Chloe put a hand on my shoulder.
As we walked into the mall, I shivered as the air conditioner was blasting and my exposed legs felt the chill, which only made me feel more nervous. What allayed that was spotting Billy sitting on a bench outside one of the stores.
“Woah! Is that really you, Jensen?” Billy asked.
“Yep.” I nervously smiled as my best friend looked me up and down.
“Now I can definitely see why ‘Liss was jealous the other day if this is what she thought she saw.”
“Shut up!” I playfully punched Billy’s arm. “You don’t need to remind me.”
“Sorry, but I really appreciate what you’re doing,” Billy said.
“Let’s just get this over with…” I sighed.
“Okay, so we’ll start with the dress, and remember, you’re supposed to like it, so pick what makes you comfortable,” Chloe said.
“Okay… But what if we run into Melissa?” I nervously asked.
“I’m counting on it…” Chloe muttered under her breath, likely because she didn’t want me to hear it.
As we walked through the second store, having not found anything remotely to my liking in the first store, I started combing through a rack, with Chloe and Billy not too far behind, idly looking around. I felt them get closer to me as I pulled a sky blue dress off the rack, but I wasn’t sure why until I heard a familiar voice behind me.
“Well, well, well, fancy seeing you here again,” Melissa said.
I turned around to see Melissa glaring at me with unknowing eyes. It’s a strange feeling when someone who you know looks at you like you’re a stranger. Although in this case, I was very glad she didn’t recognize me.
“Hmph! I guess it’s time we were properly introduced. I’m Melissa,” Melissa started. “Billy’s ex. And just who are you?”
I was still too afraid to speak, but thankfully, my sister spoke up for me.
“Her name is Jenna! And she’s Billy’s new and improved prom date.” Chloe smirked.
“Wait a minute, I know that nose, you’re a Paganelli. Jensen’s sister, right? So that makes this…” Melissa started to trail off as she intently focused on my face.
I froze, hoping that the expert powers of deduction that had led to the initial mistake would win out once again. But I didn’t have to hope, because my sister had my back.
“My cousin. She was visiting for the weekend when Jensen was trying to cheer Billy up and when she heard he didn’t have a prom date, she wanted to help out and offered to take your spot.” Chloe said.
“Okay, now I get it. No girl at our school would go out with you so you had to resort to bringing Jensen’s cousin? And I thought bringing your own cousin was as lame as you could get!” Melissa laughed.
My nervousness began to subside and instead was replaced by anger. I clenched my jaw and felt my fists doing the same around the fabric of the dress in my hands. I’d taken my share of teasing and bullying over the years, but Billy always stood up for me, even when it was just people talking behind my back. And I’ll be damned if I was going to let Melissa get away with saying stuff like that to his face! I opened my mouth to speak, but before I could, Billy interjected.
“Wasn’t so lame when you came after me last weekend at the mall with fury over me ‘moving on’ so quickly.” Billy chuckled.
“You… you…” Now it was Melissa’s turn to clench her fists and pout. “Have fun at prom… Oh, and a heads up? He’s a terrible kisser.”
Melissa stormed off once more and I finally took a breath and relaxed both my jaw and fists. Chloe and Billy both put their hands onto my shoulders and looked at me with concern.
“Are you okay?” Billy asked.
“Yeah,” I nodded, then turned to Chloe and cleared my throat. “Help me find the cutest dress in this place. Come prom night, Melissa’s going down!”
“I’m very glad to hear that, and that voice is really coming along.” Chloe grinned.
Soon, I was standing in the fitting room with Chloe helping me squeeze into the sixth dress we’d found. The first couple had sleeves, which I wasn’t a fan of, because they had too much fabric hanging from them. The next few were sleeveless, but neither Billy, Chloe nor I liked the colors much. Through much deliberation, we’d all agreed that I should at least try on this strapless pink number with an embroidered bust and a frilly skirt that goes down to my knees, although I wasn’t sold on the length.
“Can’t I cover up my legs?” I asked.
“You could, and I know you don’t want to hear this, but you’ve great legs. And you might as well show them off.” Chloe replied.
“Melissa’s dress is pretty long, so if you show something she doesn’t…” Billy trailed off.
“Message received,” I said.
But all my concerns fell to the wayside once I saw myself in the mirror wearing the dress. I never thought I’d have any sort of emotional connection to a dress of all things, but looking at myself in the mirror, even with the straps of my bra visible on my shoulders… For the first time, I didn’t see myself in the mirror, I saw a girl. A girl that, with the softer features I’d inherited from my mother, some of which Chloe lacked, which she’d always remarked she was jealous of, had a chance at upstaging Melissa.
“Wow,” I muttered as I looked in the mirror.
“I think this is the one.” Chloe smiled. “Let’s show Billy.”
“Right…” Chloe started to walk away, but my eyes were still glued to the mirror.
I didn’t know how to rationalize the feelings I felt, but I knew that there would be eyes on me at prom and not on Melissa, which is all that mattered to me. A loud whistle broke me out of my reverie and I saw Chloe standing near the fitting room’s exit, waving at me.
“Oh, right.” I nervously chuckled and rushed out of the room.
“Wow!” Billy exclaimed. “You look… wow! And I thought you looked good when you got here!”
“Thanks.” I blushed.
“Is this the one?” Billy asked.
“I think it is,” I replied.
Finding shoes was a much less emotional journey, although I have a lot of respect for women now, in regards to footwear. Finding a balance between what looks good, what matches your outfit, and what you can comfortably walk in is extremely tricky. But despite the pair of three-inch pink open-toed heels being taller than I was used to, having spent my whole life in flat shoes up till that point, they were surprisingly more comfortable than the slightly tight flats I’d spent the day walking around in. And with that, and a quick stop for a strapless bra and panties, since Chloe decided that I’d probably be smaller than she is in the chest department, despite my height advantage, we headed home for the day, sneaking my dress and accessories into the back of Chloe’s closet for the time being, at least until we figured out how to explain this scheme to our parents.
We’d get that opportunity sooner rather than later, since the following night at dinner, after I spent the day practicing in heels and doing vocal exercises, Mom decided to ask me about my plans for prom.
“So, Jensen, are you still going to prom? Because you’ve got to get that suit of your’s dry-cleaned and remember, I want to take pictures of you before you go, even if it’s just you and Billy!” Mom asked.
I would have preferred to not lay all the cards onto the dinner table, but the quick aversion of my eyes and the audible choking of her drink from Chloe set off Mom’s BS detector.
“What’s so funny?” Mom questioned.
“What’s going on?” Dad asked, joining in on the impromptu interrogation.
Chloe and I glanced at each other, her nodding and giving a supportive smile as I took a deep breath and prepared, for the second time in a week, to explain that fateful day at the mall. Once I finished, Mom and Dad were clearly still processing the story, but having known Billy as long as they did, and having encountered Melissa at enough school-sanctioned events like band concerts or football games, they were definitely supportive of the idea.
“And you’re sure about this? I mean, crossdressing seems a bit extreme to me. Why didn’t you just ask Chloe to go in your place? You look enough alike that I doubt Melissa would be able to tell,” Dad suggested.
I opened my mouth to speak but paused. Dad had brought up a really good point that I hadn’t even thought about! It was Billy’s idea, but even he jumped to having me borrow something *from* Chloe instead of asking Chloe herself. Did I shave my legs, dooming me to wearing pants in the blistering heat until prom night, for nothing?
“Unfortunately,” Chloe jumped in. “I have a date that night, and while I like Billy and all, I’m not canceling a date to go to someone else’s prom.”
Well, I suppose that’s as good an excuse as any. Although I’d sort of hoped that Chloe would be available that night in case of emergencies, but I guess if everyone knows now, there’s no reason not to call my parents. Mom was being uncustomarily quiet though, was she lost in thought? Did she have concerns?
“Honey?” Dad asked, snapping Mom out of her thoughts. “Are you all right?”
“Yes, I’m fine. I was just thinking… I still want to take pictures of you! Even if you’re in a dress and heels!”
As much as I didn’t want proof of this endeavor to stick around, it was an easy bargain to make for her acceptance. And with that, I no longer had to hide my training in Chloe’s crash course of being a girl, which made things a lot easier. I spent the next week spending whatever time I wasn’t in school learning the ins and outs of being a woman. How to sit while wearing a dress, how to touch up my makeup, more practice with the voice, and even some prep on creating a plausible backstory for me in the event Melissa corners and interrogates me in the bathroom where Billy can’t defend me. All the while at school, Melissa had started the gossip mill up and both Billy and I were getting stopped in the hall and asked about the rumors. Billy got the better end with a lot of compliments on getting another date so quickly, and how so many people felt bad for him after what Melissa did, whereas I got questions about how hot my ‘cousin’ was, given that she was able to make Melissa so jealous.
The final “test” as it were, to help me get used to being in public, was a date with Billy. But it’s not what you think, they were having a movie screening at the park that we’d bought tickets for months ago, and it was one of our favorite movies, but it was also the night before prom, so I had to be in full girl mode for two reasons, one, because the day of prom was going to be a whirlwind of salon visits and getting into my dress, and two, because Chloe’s solution to not having to stuff my bra had arrived, a set of breast forms that would be glued to my chest to ensure that they couldn’t become crooked or fall out.
“I just don’t know why we can’t put them on tomorrow morning or something,” I whined as Chloe pulled out the bottle of adhesive.
“I told you, I don’t know how good this glue is going to work, so I’d rather find out they’re gonna fall off while you sleep or while you’re getting dressed rather than at the prom. I can’t tell you how embarrassing it is to have a nip slip, especially if the nip falls onto the dance floor!” Chloe held one of the breast forms and pretended to drop it. “Now, let’s try this out!”
“Okay, fine…” I started to pull my shirt off. “Wait, you do have the solvent for that, right?”
“Of course I do,” Chloe held up another, similar bottle. “Why wouldn’t I?”
“No reason, I just had a scary thought of being stuck with those for the rest of my life.” I chuckled as I pulled the rest of it off and laid down on Chloe’s bed.
“Come on, gluing them without having the solvent is just asking for trouble,” Chloe said, applying the adhesive to the left form.
I felt a little silly as I held my chest out to show Billy the forms, snugly resting in my bra, but he wasn’t a creep about it. Well, not that much of a creep at least.
“Wow, those look great!” Billy chuckled as he poked the right one. “Are they heavy?”
“You tell me,” I giggled and chest bumped him, pushing him back slightly.
“Ouch!” Billy laughed, then turned serious. “You know we don’t have to go, we’ve seen it a million times. We could practically re-enact the whole movie here.”
“And miss out on seeing the space battle on the big screen? No way! I love that movie way more than I’m embarrassed to be seen like this, besides, I’m gonna be seen tomorrow night anyway, and I won’t get to see any space battles.” I said as I pulled my favorite “Stellar Skirmishes” shirt over my head.
I glanced into the mirror and checked myself, as Chloe had trained me to do. My hair, which was styled as femininely as I could, was held securely with a green headband, chosen by me because it was the color of my favorite character’s costume in the movie, my makeup was subtle, but noticeable, with my features softened, my lips glossy and a little bit of mascara on my eyelashes, my shirt rested over my chest, which was a new experience for me, and my high-waisted shorts rested above mid-thigh, slightly higher than the hem of my prom dress, so it was good practice, as Chloe had said when she helped me pick it out. Rounding it off was a pair of sandals with a slight heel, which were slightly tight since they were Chloe’s. I chuckled as I thought to myself that I’m not making such a great girl if I only actually own one pair of shoes.
Arriving after the short walk to the park, Billy and I chose a prime location for our blanket, and Billy left me to set it up as he went to get snacks. Everyone was pretty spread out, but I was still on the lookout for anyone who might recognize me. Thankfully, I didn’t see anyone who might and Billy was soon on his way back with a large tub of popcorn and two sodas.
As the movie began, we started mouthing lines of dialogue to each other before the characters said them aloud, but we quickly got as invested in the movie as we had when we’d seen it for the first time in Billy’s basement as kids on his dad’s old VCR. So much so, that I don’t think either of us really noticed when we both reached for the popcorn at the same time, but I definitely noticed it the second time it happened. We both quickly looked away from each other, and I don’t know about Billy, but my face was flushed. I wasn’t really sure why I was so embarrassed, it’s not like we were actually boyfriend and girlfriend, and yeah, I liked him, but as my best friend! But there’s something about sitting on a blanket next to another guy while dressed in my sister’s clothes that made it a very different situation than any other time we’d seen this movie.
But it was just one more day and I could put all this behind me, and all I needed to assuage my trepidations was picturing Melissa’s smug face as she watched Billy and I have a better prom night than she did.
When the movie was over, after stretching our legs, we started to pack up our blanket, discussing the film while we did.
“It really is incredible that even forty years ago the sets were so well-put-together that you can’t even see any seams or strings in this remastered print,” I remarked, as I finished rolling up the blanket, handing it to Billy.
“Yeah, it’s crazy how it looks so much better than even the version that’s in the “Stellar Skirmishes” Blu-ray collection,” Billy said as he stuffed the blanket into his backpack. “Oh, hold on.”
Billy walked up to me and stared intently at my face. My eyes widened as he reached his hand towards my hair. I tried to ask him what he was doing, but my mouth was suddenly dry, despite the fact I’d finished my soda. Time seemed to stand still until Billy pulled his hand back and showed me a piece of popcorn.
“Saving this for later?” he asked, jokingly.
“Uh, thanks.” I brushed some hair behind my ear. “You could’ve just told me it was there and I’d have gotten it myself.”
“And then have to play the, ‘No, my left, almost, you almost got it!’ game? Seemed easier that way.” Billy smiled.
“Maybe for you,” I muttered under my breath.
After that uncomfortable moment and a relatively quiet walk back to my house, we stood on my porch talking.
“I should be done getting ready around five, and prom starts at six, so try to get here early. My mom still wants to take pictures.” I said
“And you’re okay with that? Pictures of you like that?” Billy asked.
“Not really, but she promised not to show anyone,” I replied.
“Sounds good. Can’t wait to see how well you clean up.” Billy chuckled. “Good luck with all that tomorrow.”
“Thanks,” I said.
As Billy turned to walk away, the porch light turned on and the front door opened, revealing my dad. I blushed, still embarrassed to be seen this way by him, although he was clearly finding a lot of humor in the situation.
“I trust you treated my daughter right tonight, son?” Dad asked, emphasizing ‘daughter’ and winking.
“Of course, sir.” Billy smiled.
“God, Dad, stop it!” I tried vainly to push my father back into the house.
“And you’ll treat her right tomorrow night too, right?”
“You know it!”
“Okay, that’s it, leave them alone!” Mom dragged Dad back into the house and smiled at me apologetically.
“Thanks,” I said, then turned to Billy. “See you tomorrow, now get out of here while you still can.”
Billy smiled and headed down the driveway towards the street and I walked into the house and put my face into my hands.
“What? I’m not allowed to have fun with this?” Dad asked.
“One man’s fun is another’s embarrassment, Dad,” I replied in a deadpan.
“All right, I’ll let up. But I can’t make any promises for tomorrow.” Dad walked away chuckling.
“I’ll keep him in check, don’t worry, honey.” Mom said as she hugged me. “Did you enjoy your movie?”
“Yeah, it was great,” I said, not really wanting to bring up the strange feelings I’d been having. “But I’m wiped.”
“And you’ve got a busy day tomorrow, better get some rest.” Mom kissed me on the forehead and let me head upstairs to my room.
I removed all the makeup and disrobed, leaving myself clad in just my t-shirt and a pair of gym shorts. A glance in the mirror showed me that with the false breasts and my still tucked male parts, I looked even more like a girl and I was in my own clothes! Crawling into bed, I fell asleep to visions of my walking across the dance floor in a dress and heels as everyone looked on, especially Melissa. Just a few weeks earlier that would have been a nightmare that might have been concerning to have, but it was about to be my real life. What a difference a few weeks can make, right?
The next morning, I was nervous as I walked into the salon, even if my outfit was by and far the most masculine I’d worn as a girl so far, a casual button-up blouse, a pair of jeans and flip-flops. Chloe walked me up to the counter and told the girl working there that I was there for my appointment, though all she’d told me was that I was getting the works, and the girl at the counter cheerfully walked me to one of the chairs as Chloe told me she’d be back to pick me up later. When I got to the chair, I met my stylist, who I immediately recognized, thanks to her very identifiable haircut. I'd know that short blue hair anywhere, it was Kris, one of Chloe’s best friends, and someone who’d surely recognize me in turn.
“So, what are we thinking about for today?” Kris said. “After all, prom is a big night, right Jenna?”
I froze, I hadn’t told her my name, and even if it was on the appointment listing, she said it in such a way that removed all ambiguity from the situation. She knew who I was. I nervously licked my suddenly dry lips.
“I… uh…” I stammered.
“Don’t worry,” Kris whispered. “Chloe told me everything. It takes a big man to do what you’re doing. And don’t worry about telling me what you want, Chloe was very specific about what she wanted.”
“That’s a relief,” I sighed. “She’s been training me to be a girl, but I’m still pretty clueless.”
“Let me handle everything, don’t worry, you’re in good hands.” Kris patted me gently on the shoulder. “And you’re already adorable, so you won’t need much help.”
Although I blushed at the comment, I was glad that I knew my stylist. Finally able to relax, I settled into the chair, kicking off my flip-flops and leaning my head back. Kris started to prepare and I remembered all the times I’d seen her doing Chloe’s hair before dates and dances throughout high school, never thinking that one day it’d be my turn in the chair.
I sat while she washed my hair in the basin, which was a lot more relaxing than I thought it would be, and we spoke a bit, as I filled her in on the parts of the story that Chloe had omitted in her retelling.
“And she really couldn’t tell it was you?” Kris asked.
“Nope.” I replied.
“I mean, I guess I could see it. I don’t know if I’d have guessed that you were you if Chloe hadn’t warned me and showed me a pic of you in your dress.” Kris remarked as she towel-dried my hair.
As I soon found out, the works are a lot more intensive than just getting my hair, nails and makeup done. It was slightly uncomfortable as my eyebrows were threaded, but the strangest part of the experience was the false eyelashes being glued to my regular ones. In seconds, I had a heaviness on my eyes that felt completely different than anything I’d ever felt. I guess I got lost in my own reflection, blinking and watching the false eyelashes fluttering because I felt a sharp tap on my shoulder from Kris, who had been trying to get my attention.
“Earth to Jenna! What color do you want?” Kris asked.
“Color?” I replied.
“For your nails, I know the dress is pink, but there are a bunch of shades to choose from.” Kris showed me a few bottles of pink nail polish, some lighter, some darker, some with sparkles in them.
“I thought Chloe picked everything out,” I questioned.
“She did, but she couldn’t decide between these two pinks, and french tips.” Kris responded.
I vaguely knew what french tips are, having seen them before, but a spot of confusion must’ve been noticeable on my face, because Kris quickly wiggled her fingers in front of my face.
“These are french tips. And here are the pinks,” she held up two bottles, one a very bright pink, the color of Pepto Bismol, which I ironically found nauseating to look at, and another which was somewhat understated and matched the dress better.
“That pink.” I pointed to the softer pink.
“I liked that one better too.” Kris smiled.
Getting my nails done was an interesting experience as well, soaking my feet, it felt like a foot massage as the attendant brushed away all of the callouses. Then she filed and buffed my toenails before she started painting them. I always saw my Chloe and Mom using cotton balls or those foam toe separators at home, but never thought I’d see them when I looked down and wiggled my own toes. The color looked nice, though. Then the attendant turned her attention to my hands, while Kris continued to work on my hair, using an iron to curl it. The attendant worked on my cuticles and shaping my fingernails before applying the acrylic tips. It’s incredible how just adding long nails can completely change how a hand looks. I didn’t think my hands were remotely feminine before, but now, they seemed like girl’s hands, even more so after my new nails were painted with the same soft pink as my toes.
At the end of it, my hair had been styled into what Kris called a Messy Braided Crown, with a braid going around over my ears and joining in the back, leaving several messy locks hanging around. I was appreciative that everything Chloe chose would be easy to reverse come Monday, no highlights or dyes or extensions. Makeup was a slightly different story, as my nails dried, Kris started work on my face. Some foundation to even me out, a brownish glittery eyeshadow, pink lipstick, not to mention the false lashes, all served to transform my face from a boy into a certified knockout!
“Wow…” I gazed into the mirror in amazement.
“I’m glad you like it.” Kris smiled as she started cleaning up. “You make a cute girl. I think, whatever the goal of this plan is, you’re gonna succeed.”
“I hope so.” I said, flexing my fingers and admiring my new nails.
As I slipped my flip flops back on, I heard footsteps walking towards me, which suddenly stopped and I heard:
“Wow!” Chloe exclaimed.
“Seems to be the word of the day here,” Kris giggled as Chloe remained slack jawed, staring at me.
I took a deep breath as I glanced over at the dress laying on my bed. While I’d certainly passed the point of no-return when I let Chloe glue the breast forms in place, it was still pretty daunting. I glanced in the mirror and looked myself up and down, clad in only a strapless bra and a pair of panties, still surprised at how well Chloe was able to help me tuck down the only thing that reminded me that I was still the same boy I was just a few weeks ago. As I turned back to the dress, my door opened slightly and I heard a gentle knock.
“Need any help?” Chloe asked.
“Sure, come on in.” I replied, and Chloe entered. “This is it…”
“You look great! And you’re gonna be fine.” Chloe said as I stepped into the dress and pulled it up to my chest. “I never thought I’d be helping my brother zip up his prom dress, but it’s been nice having a sister for a little bit.”
“Yeah,” I said, thinking about how, despite me only doing this as retaliation against Melissa, I’d had some fun hanging out with Chloe as she taught me the ins and outs of girlhood. I don’t think I’d go so far as to say that I’d miss being ‘Jenna’ when this is over, but I don’t think I’m going to regret what I did.
Once my dress was zipped, I slipped the heels onto my feet, wiggling my pink toes as I took a few steps to make sure that I hadn’t forgotten how to walk in them since my last practice session two days earlier. Chloe headed downstairs to “announce me”, and as I carefully stepped down the stairs, I was nearly blinded by a camera flash when I reached the final step.
“Sorry!” Mom exclaimed. “ Couldn’t resist getting an action shot!”
I rolled my eyes as I blinked and waited for my sight to fully return. As it did, I saw Mom with the camera standing next to Dad who was standing next to Chloe and Billy, who was uncharacteristically early, who’d clearly had a haircut and was wearing a sharp suit with a bowtie that matched my dress.
“Wow, who knew all I needed to do in order to get you to show up on time when we go places was to wear a dress?” I remarked.
“Well, I couldn’t disappoint your parents, right?” Billy replied. “You look breathtaking, by the way.”
“Thanks.” I blushed. “You clean up pretty good yourself.”
“That reminds me, what do your parents think of all this?” Mom asked. “Are they going to want pictures?”
“Actually, they still think I’m going stag with Jensen.” Billy chuckled. “I wasn’t quite sure how to explain all this to them.”
“Maybe you can tell them tomorrow with some pictures.” Mom said. “Now, get together, I need some pictures of the two of you!”
Billy walked over to me and we stood awkwardly next to each other, Billy still a bit taller than me, even with my heels. Billy kept his arms at his sides, no doubt because of my father keeping his arms crossed as he stood next to Mom.
“Come on, you two! Pretend like you know each other!” Mom shouted. “Billy, put your arm on his shoulder! Good, now Jen, put your arm around his shoulder, Billy, move your arm to his waist and Jen, put your hand on his chest… Perfect!”
Billy and I shared knowing glances in between shots as Mom continued to take photos.
“This wasn’t really how I expected it to look, but I’m so proud of you! A shame I won’t be able to post these photos anywhere, but you make such a cute couple regardless.” Mom smiled.
“Mom!” I blushed, while Billy chuckled.
“Oh! How about one where you’re kissing!” Mom exclaimed.
“Mom!” I snapped.
“What? Only on the cheek… Never mind, I think I’ve got enough memories for tonight. I’m so proud of you, baby.”
“Thanks, Mom.” I said.
“Wait a minute! Billy, don’t you have something for Jen?” Dad suddenly exclaimed.
“Oh yeah,” Billy walked over to a table and picked something up.
As he carried it over, I saw that it was a box for a corsage and a boutineer. He opened it up and took out the corsage, and made eye contact with me.
“What?” I asked.
“You need to hold out your hand!” Mom whispered to me.
“Oh… right.” I said, and held my hand out.
I imagined it would probably get worse from there, but this was the girliest I’d felt yet during this whole experience. It felt particularly girly since Mom had resumed taking photos at this point. When he finished securing it onto my wrist, I went to grab the boutineer and pinned it to his lapel.
“Well, I think that does it, right?” I asked.
“Yeah, I think the limo ought to be here by now,” Billy replied.
“A limo?” I asked. “That’s a bit overkill, isn’t it?”
“I’d already paid for it for ‘Liss and I. But I’d much rather share it with you.” Billy smiled.
“Good luck,” Chloe said, giving me a big hug and handing me a pink clutch purse that held my phone, some makeup and some emergency cash that I’d packed earlier.
“Have her back at a decent hour, okay, Billy?” Dad said, sternly.
“Will do,” Billy nervously chuckled, still not sure if Dad was joking or not.
“Have fun, you have your purse right? And your phone is in there? Make sure you have-!” Mom took a deep breath and started to continue.
“Don’t worry, Mom. I’ve got everything I need. See you when I get home.” I said, giving her a hug.
And with that, we were off, the limo ride was nice, and Billy and I discussed our game plan as we rode to the local hotel whose ballroom would be holding the prom.
“Okay, so we’ll walk in together, go find our table so you can put your purse down, and then we find out which part of the dance floor Melissa is at so we can give her a great view of us dancing.” Billy said.
“I hope I’m good enough, I couldn’t dance before all this, and I’ve only practiced at home.” I said.
“Don’t worry, if you’ve got two left feet and I have two left feet, then that means that collectively we should make one competent dancer.” Billy insisted.
“I don’t think that’s how the metaphor goes,” I giggled.
He really was a goofball, and it’s a shame that Melissa just wanted to climb the social ladder, cause she was missing out. Speaking of Melissa missing out, when we got to prom, after taking some photos in front of a backdrop set up by the student council, looking slightly more comfortable than we had at my house, there were the occasional stares, as people tried to place me, but I don’t think anyone figured it out, and if they asked, Billy and I kept up the charade that I was my own cousin, visiting from across the country.
“Ohmigod, you look just like Jensen!” said the girl who sat behind me in history class as we made smalltalk around our table.
“Yeah, we get that a lot.” I smiled as Billy and I crossed through the crowded ballroom.
“There she is.” Billy said, pointing out Melissa, wearing a purple sequined number, standing with Josh and a few other girls, (cheerleaders I think) and their dates.
Melissa clocked us immediately and her expression went from pleasant to furious in record time. I half-expected her to storm over to confront us, but she just started hanging off her date’s arm and acting overly happy.
“Mission accomplished, right?” I asked.
“Stage 1 is complete, but let’s see how much farther we can push it.” Billy replied. “Care to dance?”
“Sure,” I smiled and took Billy’s hand.
We went out to the dance floor and started moving to the beat. The DJ was playing a fairly well-known pop song, and I managed to hold my own, even as I felt my dress bouncing as I moved. We’d joined a group of our classmates, so the stakes were pretty low, but I won’t deny that I felt pretty self conscious as I swayed in my heels. After a few songs, Billy and I were both pretty out of breath and we decided to take a break.
“Punch?” Billy asked, motioning towards the refreshments table.
“Sounds good,” I replied, and we started to make our way through the crowd.
Arriving at the table, we found Melissa and Josh standing near it, chatting with some other couples as they poured themselves some punch.
“Let’s come back,” I started to pull Billy away, but he resisted. It was fun messing with Melissa, but I didn’t want a direct confrontation.
“No, we have as much of a right to be here as she does,” Billy said.
He continued walking up to the table and picked up a plastic cup, filling it with the ladle sitting in the punch bowl. I stood hesitantly behind him. As he handed me a cup, I felt a presence behind me and jumped slightly, but not enough to spill anything on my dress, thankfully.
“Hello, you!” Melissa grinned and spoke in that fake, sing-songy tone that people use when they’re really angry.
“Hi, ‘Liss… Josh,” Billy said. “You both look good.”
“Thanks, and so do you and your date! She certainly cleans up well,” Melissa smirked.
“Well, when I’ve got a guy who’s worth cleaning up for, I put in the effort.” I retorted.
Unable to think of a snappy comeback, Melissa just stomped her heel and grabbed onto Josh’s arm.
“Come on, Joshie-poo, let’s go dance!” Melissa snapped as Josh helplessly followed Melissa to the dance floor.
“Does that mean I have to call you Billy-poo?” I joked.
“Please, for the love of god, never utter that word again.” Billy chuckled.
With that, we returned with punch to our table, where some of our classmates had also decided to take a break from dancing and we chatted a bit, giving some fake highlights of Jenna’s life, as well as explaining how my ‘cousin’ had graciously given me his ticket so that Billy would have a date. Made me feel really good, since maybe rumors of my gallantness might help me in finding a girl for myself. After some more dancing, some eating and more showing off in front of Melissa, the night was starting to wind to a close, as Billy and I stood on the dance floor as the latest song to play had just faded out and the student council president had climbed up onto the stage with a microphone.
“Hi, everyone! Before the final slow dance of the evening, we’d like to announce our prom royalty! The votes are in, and it’s time to crown our Prom King and Queen!” the student council president exclaimed, waving an envelope.
“Wow, I totally forgot about this.” I whispered to Billy.
“Really? So you didn’t see the nominations list?” Billy replied.
“Nope. I guess it’ll mean Melissa will have a great view of us from up on stage, right?”
“I hope so…” Billy said, nervously.
“Okay, folks, as voted on by you, this year’s Prom King is… Billy Gardner!” the student council president exclaimed.
“What?” I questioned. “How did you win?”
“Maybe a lot of people feel bad for me…” Billy responded. “I knew my name was on the list, since ‘Liss nominated me weeks ago when we were going together, but I didn’t expect to win.”
“I guess Melissa loses either way, because I doubt she’ll be happy standing up next to you.” I remarked.
“And this year’s Prom Queen is… Oh, that’s surprising. Folks, we’ve got an upset this year, but for the first time, the title has been taken by someone who doesn’t even attend our school! But the margin of write-in votes was so huge that we can’t deny that our new Prom Queen is Jenna Paganelli!”
“What?!” I turned to Billy. “H-how did that happen? Why was my name even on the list?”
“Melissa made sure everyone knew that I would be here with your ‘cousin’, but no matter how many friends she has, I know most people were on my side regarding the breakup. I guess she figured Josh would get more votes and never bothered to take me off the list, but it backfired, and everybody voted for me in solidarity, and I guess they also wrote you in so that I wasn’t up there alone.” Billy said.
“Come up to the stage, lovebirds, we don’t have all night!”
I would have been frozen to the spot if it wasn’t for Billy, gracefully guiding me by my hand up to the stage. Looking out at our assembled peers, I stood still as the student council president put a crown on my head and handed me a bouquet, before moving onto putting Billy’s crown on his head. The president tried to hand me the microphone, but Billy intercepted it.
“Jenna, do you want to say anything?” Billy held the microphone out to me.
“I’m… speechless, I really don’t know what to say.” I said into the microphone, so nervous that I wasn’t even sure if I was still doing my ‘Jenna’ voice.
“Then I’ll just say thank you to everyone who voted for us, you really made this a memorable prom night. And I’d like to give a special thanks to everyone who made it possible, they know who they are.” Billy winked out into the audience towards Melissa.
To this day, I have no idea where the impulse came from, but as I saw Melissa glaring up at us, with Josh trying to comfort her, it was like someone took control of my body, and I handed the bouquet back to the student council president and grabbed his face with my manicured fingers and brought his mouth to mine and kissed him. My eyes were closed, but I imagine that Billy’s were wide open, at least until I felt him relax and accept the kiss. I heard the crowd going wild with ‘whoos’, ‘awws’ and ‘oohs’ until I released Billy’s face.
He pulled away, temporarily speechless and touched a finger to his lips as I smiled at him.
“That’s definitely one way to celebrate!” The student council president laughed as she handed the bouquet back to me and went back to addressing the audience. “Give it up one more time for this year’s Prom King and Queen!”
We quickly got off the stage and headed back to our table. Unfortunately, I wasn’t able to see Melissa’s face as we kissed, but I imagine she was seething, and I couldn’t see her anywhere in the ballroom as we walked. When we sat down, Billy grabbed my hand and looked into my eyes.
“Are you okay?” Billy asked.
“Yeah, why?” I replied.
“That kiss wasn’t part of the plan,” Billy said. “Not that I’m complaining, but…”
“I improvised,” I shrugged. “Felt like the right thing to do.”
“Yeah… It did, didn’t it?” Billy asked. “What does this mean?”
“I… I don’t know.” I replied.
I really didn’t know. Those feelings I’d been feeling as I spent time dressed as a girl, practicing, especially the time I spent around Billy, they’d frightened me at first, but when I kissed him, I felt safe… It felt right. But I had tomorrow to figure that out, tonight was prom, and I was determined to see it through. But first, I had something important to do.
“I’ve gotta use the bathroom,” I said, with all the excitement sending the punch right through me. I grabbed my purse and stood up.
“You sure you wanna be alone with Melissa around?” Billy asked.
“Don’t worry, after that upset, I don’t think she’ll be a problem.” I smiled and patted him on the shoulder, heading out of the ballroom.
I let out a sigh of relief as I walked into the women’s restroom and worked my way around the dress and the tuck job to relieve myself in the stall. As I finished up, I heard a low sob coming from one of the other stalls. I heard the stall door open before I stepped out and saw Melissa, her makeup running down her face standing across from me.
“I hope you’re happy, you’ve ruined my night.” Melissa pouted with crossed arms, leaning against the wall near the sink.
“I’m sorry that you lost, but I didn’t ruin anything. YOU confronted Billy at the mall after YOU cheated on and broke up with him! YOU got all up in my face at the dress store! And YOU spread it around that Billy was taking me to the prom so everyone knew who I was tonight! All I did was exist, so if I ruined your night by spending the evening with a sweet, caring, gentleman of a guy that you just tossed aside like last week’s moldy pizza the moment a better option came along, then I guess I did.” my fists were clenched as I shouted, letting out all my frustrations.
Melissa just glared at me, clearly not moved at all by my display of sheer emotion. But just then, another one of those impulses hit me, and I turned to leave, but hesitated.
“Oh yeah, and just so you know, I let you borrow a pencil in English class last month, I’d really like it back.” I smiled.
I watched as Melissa’s brain began to piece together what that crack meant, as each individual braincell lit up with the revelation that she hadn’t been upstaged by Jensen Paganelli’s cousin. She’d been upstaged by Jensen Paganelli in a dress and heels. I quickly made my way out of the bathroom before she could say anything and headed back to the table, sitting down next to Billy.
“How’d it go? Did you see ‘Liss?” Billy asked.
“We had a few words… But I don’t think she’s gonna come near us again tonight.” I giggled.
“Do I even wanna know?” Billy asked. “You know what? Probably not.”
“You’re probably right.” I said.
As another pop song came to an end, the lights went lower and the dance floor cleared of everyone except those with dates and the DJ began to play a much slower song.
“Sounds like the last dance is about to start…” I tapped my polished nails against the table.
“I think everyone would be disappointed if the Prom King wasn’t out there with his queen.” Billy said.
“I think you’re right,” I smiled as we stood up and Billy led me out to the dance floor.
The crowd opened and gave us a space in the middle to dance. Practicing slow dancing with my sister in her room had been very different, but I think I quickly got the hang of it as Billy had his hand around my waist and my manicured hand intertwined with his. For a moment, it truly felt like it was just us on that dance floor, and as I gazed into Billy’s eyes, I was glad to be in the arms of my best friend, and I wouldn’t have had prom go any other way.
And honestly there’s not much more to talk about, we finished off the night, had a long talk in the limo on the way back to my house where we had an even longer conversation with my parents and Chloe about me. My parents were surprised, but not shocked, nor was Chloe, and they were there to support me through everything, although we agreed it would be easier if I spent the remaining week of high school as Jensen and became Jenna full-time after graduation, and although I was sad to see the acrylics and false eyelashes go, albeit temporarily, I also didn’t want to suddenly become the object of attention.
So, at graduation, while Jensen walked across the stage to receive his diploma, it was Jenna who started college in the fall. It was a bit of a bummer, since Billy and I had schemed to become roommates, which obviously couldn’t happen anymore, but we still spent about an equal amount of time in each other’s rooms, so it all balanced out. Besides, once we save up enough for an off-campus apartment, it’ll be a moot point. And to think it all started because of a case of mistaken identity, but I’ve really got to thank Melissa one day, because that prom night, for better or worse, changed my life. And I definitely think it was for the better.