Crossdressed for PROM [Full Story]

Part 1: https://youtu.be/TEq51OIY1WY

Part 2:

Part 3:

Part 4:

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.

“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.

The end!