Prom? Ch. 01


Hello everyone, this is my first story I've ever written and posted on here! I hope you like it. If you do like it, be sure to vote and comment so I know you want to read the next part!


My legs shook as I powered my bike up the hill. I knew I had to get to Natalie's house as soon as I could. A few minutes before I had received an ominous text that read:

ANDY. COME QUICK. My house RIGHT NOW. Mike here. Ripping bong. Sad boy.

I didn't even try to start my lemon of a car. I went straight to my bike, taking all of the trails and shortcuts I knew on my way up to Natalie's house. I dodged BMWs and Audis as I took a shortcut down the wrong way of a one way street, my ponytail flying behind me. I finally reached Natalie's house and hopped off my bike, ringing the call bell at the gate. I heard a beep, and the black iron gates that led to Natalie's stone driveway slowly opened up.

Natalie's parents are loaded: and when I say loaded, I mean absolutely loaded. They founded a cosmetics company 2 years before Natalie was born, and it achieved major success. After purchasing land on the hill that overlooked the entire suburb, the couple had a house built that looked like it was straight out of the Hollywood Hills, just repackaged and placed in the Bay Area. Natalie's father had a pool house built, and told Natalie that they'd rather she do any partying out in the pool house rather than in the main house. This included smoking weed, which is normally what we would do at Natalie's house.

I reached the pool and laid my bike down on the ground outside. I opened the door to find a paused game of Call of Duty on the TV, Mike curled up in a ball on the couch, and Natalie sitting nearby, her hand on Mike's shoulder. Mike was shuttering every few seconds, sniffling his nose as tears escaped his eyes. He was clutching the bong tight to his chest.

"Mike? What's wrong buddy?" I said as I set my backpack down and took a seat on the couch next to Natalie. He put the bong on the floor in front of the sofa and tried to sit up, ultimately failing and curling back up into the ball.

"Jessica...she...she...did..." he responded, struggling to get the words out in between sobs.

"Jessica cheated on him with a teammate of his," Natalie said, causing Mike to erupt into another set of sobs. She went in to hold him and I went in with her, holding my arm around her and using my other arm to pat Mike on the back.

"Screw her man, you can do better. She was always bossing you around too," I said. He nodded his head back at me, cracking a hint of a smile.

Natalie, Mike and I had really come a long way since we met on the playground back in 1st grade. Well, to be more accurate we met in the mud near the playground. Mike and I loved playing in the mud, and one day a redheaded girl jumped in with us, ruining her designer dress. A beautiful friendship was formed, and we hung out together all throughout elementary school, riding bikes and going on adventures. Even in middle school when we went off to form our own identities, we remained friends. We each ended up in three very different cliques at that time: I was into theater, so I quickly become friends with the theater nerds and the musical kids. Natalie was rich and pretty, so she was popular before she even started. Mike was more interested in computers and video games, so he ended up being a bit of a nerd. The summer before we started high school, Mike moved to the next town over, and had to switch from our high school, West River High, to a new school, Polk High School. Despite this, the three of us remained friends, hanging around at Natalie's ripping bong or my place watching tv.

We stayed in our positions huddled up against Mike until he stopped sobbing. When he composed himself, Natalie and I got off of him and sat on either side of him. Mike picked up the bong and grabbed a lighter from his pocket. He lit the bowl and took a big rip, clearing the milky smoke encased in the glass. He passed the bong to Natalie and exhaled. As he exhaled he began laughing, causing him to cough and choke a little bit, smoke exiting through his nostrils.

"Shit guys," Mike said as Natalie lit the bowl, "prom's in a week and I don't have a fucking date."

"Ah crap, that sucks man," I said as I received the bong from Natalie.

"Yeah, guess you can't bring a cheating bitch to prom," Natalie said. "I could probably find you a girl from me and Andy's school?"

"Yeah dude, Natalie can find you a popular girl or I could find you a theater girl? That would be fun, right?" I said. I had taken one of my theater friends to West River's prom, and I had a blast with her.

"No guys, I don't really want to go with some girl I don't even know. I wanted to go with someone special," he said. He sighed deeply and leaned back on the couch. "I wanted to go with Jessica."

"Well I'd totally go with you, if I wasn't already going to Polk's prom with someone already," Natalie said. Polk high school's was the fifth prom Natalie would be going to: I guess it's good to be popular.

We sat around for awhile, taking hits, lost in our own thoughts. Natalie and I both knew that Mike wasn't going to ask out a girl on his own: while he had grown to be a star offensive lineman for Polk's football team, he was still a computer nerd, and wasn't very popular with the ladies at Polk. It was a miracle he had even gotten with Jessica in the first place: she was one of West River's most popular girls. I tried to think of girls that Mike could bring, and I could tell Natalie was doing the exact same thing in her mind. Maggie? Nah, I think I lost my goodwill with her. Maybe Sherri? Sherri is an option, actually. That could wo- my stream of thought was interrupted by the sounds of Natalie's laughter. They weren't normal laughs, or giggles, they were deep, hearty belly laughs that permeated the whole room.

"WAIT...WAIT...HOLD ON...I GOT IT," Natalie said as she composed herself. She sat up and turned to both Mike and me.

"What if...well, what if you don't even take a...girl...Mike?"

"Um, what do you mean by that?" Mike asked, his brows shooting up.

"What if you went with Andy?" Natalie said with a sly grin on her face. Now my brows were shooting up.

"Um, little problem with that Natalie," I said. "Mike is straight. And everyone knows he's straight. So he probably wants to take a girl."

"Yes, exactly! A girl," she said, emphasising the girl part. I was still confused.

"Untie your hair, Andy," she said. I did as I was instructed. She took my hand and led me from the couch to the bathroom, with Mike following close behind. She stood me in front of the mirror.

"Your cheeks are pretty angular, that's nice. Jawline not square at all, another plus. Eyebrows could use some work, so could the nose. Nose has to be contoured..."

"Natalie, what are you talking about?" I asked.

"I'm saying, maybe he should go with a girl. Can you think of a good girl name, Andy?"

she asked, smiling.

"Um, what the hell?!" Mike and I exclaimed in unison.

"Natalie, I don't want to go with a guy! Nevermind a guy dressed as a girl! What the hell


"Yeah Natalie, in case you didn't notice, I'm kind of, ya know, A GUY!" I said. We went back to the couch, and Mike grabbed for the bong, taking a long, deep hit.

"Oh come on guys, it won't be that bad!" she said, sitting on the arm of the couch. Mike and I continued to huff.

"Okay, Mike, here's the reality. You have no date for your prom, which is in literally a week. You need to find someone, and we know you aren't going to find someone yourself, so we need to help you. Unfortunately, you don't want to go with anyone who we might suggest, so the only other options are either me or Andy. And I can't go because I'm already going as someone else's date. Therefore, Andy is your last option." she said, taking the bong from Mike's hands. Mike sat and contemplated for awhile before standing up and turning to me.

"I homo man..." he said, "but...I kind of need a date."

"Come on man, isn't there anyone else?" I asked, knowing the answer would be no.

"Think about it Andy! It's really not that bad, it's just for one night. You help out Mike, and you get to go to the afterparty!" she said. I looked at Mike, sitting on the couch again. It really was his time of need. I couldn't let my friend down like that. It was just for one night after all, right? How bad could it be?

"Okay. Fine. Do you really think that you can make me over into a girl?" I asked.

She smiled. "Of course I can! I just need you in a chair for about an hour and my full makeup arsenal. Well, that will be to make you look like a girl. Acting like a girl is completely different. You'll need to practice that."


"Yeah, like go out on a test run. Get you out in public as a girl. I can teach you how to blend in. Plus we need to get you a prom dress soon, especially if it's in a week. We better hurry up, we might even have to do this now," she said.

"Now? What are we doing now?" I asked.

"Oh, I have an idea! How about we go prom dress shopping today, and we let today be your 'test run' kind of thing! It'll look better than just a guy shopping for a prom dress. That would just be weird," she said. I rolled my eyes.

"Okay, fine. I'll do it. We should get going if this makeup really takes an hour," I replied. She squealed and jumped up from the couch, giving me a kiss on the cheek.

"Oh this will be so fun! It'll be like having my own little doll, but alive!" she said, literally skipping out the poolhouse door, going towards the main house. Mike and I rolled our eyes.

"Listen man-"

"Don't mention it," I said. "Really. Don't mention it."


"Okay I hope you have your robe on!" Natalie said as she barged into the room. I was in Natalie's bedroom, a first for me personally. It was hard to believe, but I had never been upstairs in her house in my 12 years of friendship with her. We usually just hung out in her poolhouse, since that was the designated weed spot. I was quite the sight to see: I was dressed in a pink fluffy robe, with my hair wrapped in a matching pink towel. I had shaved all of the hair off of my body below my eyebrows like Natalie said, and used the body wash, shampoo and conditioner that she left in the shower. Now I was sitting on the edge of her king sized bed, in her king sized bedroom, in her king sized house, legs crossed, not sure of what could happen next.

I had never actually crossdressed before. I obviously wore stage makeup for the musicals, and had dressed in crappy drag once or twice for Halloween. I wasn't exactly a stranger to feminine things: I was heavily involved in musical theater, and most of my friends fell somewhere under the LGBT umbrella. But in terms of actually trying to pass as the opposite sex? Never. Which is what mortified me even more: what if I ended up looking like a man in a dress? I wasn't too concerned about that actually. Years of cross country running and track team membership had toned my body, making it almost feminine. I was not bulky at all, moreso toned and trimmed, especially in my legs. I briefly uncrossed them and was reminded of the new silky-smooth feeling they had. Just as I crossed my legs back, Natalie came back into the room with a box in her arms.

"My parents boxed up all of my sister's clothes when she moved out. She's closer to your body type than I am," she explained. Natalie was about 5'5, and I was about 5'8, so it made sense that she'd raid her taller, older sister's wardrobe.

"I still don't know how you intend to pull this off," I said, getting up from the bed and looking in the mirror. "Right now I just look ridiculous."

"Well that's because I haven't done your makeup yet! Sit down at my vanity so I can do it," she said, directing me to the chair in the corner of the room.

I sat down in the chair and looked at the multitude of cosmetic products in front of me. The surface of the desk was completely covered: brushes, bottles, pencils, tubes of mascara, lipsticks, eyelash curlers and mirrors cluttered up the entire desk.

"Perks of having parents who run a cosmetic company," she said when she saw me observing all of the products on her desk. "Good thing you have my makeup skills at your disposal."

For the next hour or so she went to work on my face, slathering on layers of foundation and coverup, working me over with brushes and sponges. Next she worked on my eyes, lining them in a winged style and curling my lashes.

"Damn, I'm jealous of your lashes. Stupid boys never appreciate good lashes," she said, rolling her eyes. I batted my curled, voluminous lashes in response, sticking my tongue out at her. She continued her work, telling me to pucker up as she pulled out a tube of lipstick.

My hair was her last order of business. I had been growing and maintaining my wavy hair since the 8th grade, and I kept it to about upper back height. Typically, I kept my hair in a loosely tied bun on the top of my head; however, when I wore my hair down, from behind I kind of looked like a girl with dirty blonde hair. Natalie pulled my hair out of the towel, letting it fall down my back and chest. She took out a hair straightener and went to work. When she was done, my hair felt noticeably longer, now coming almost to the middle of my back. She backed up and signaled for me to go to the full length mirror in the corner and I sprang up from the chair, eager to see my new appearance. I went to the mirror and my jaw hit the floor.

The person staring back at me had long, straight, dirty blonde hair, that went down past her chest. She had narrow cheeks, a soft jawline, and a small nose. Her blue eyes were big, lined in black, with long lashes. Her lips were a flirty bright red, perfectly contrasting with her pale skin. I moved my arm, and she moved hers. I ran my hand through my hair, and she ran her hand through her hair.

Oh shit. That's me. I turned to Natalie, who was looking elated.

" you like it?" she asked, giddy with anticipation.

"Holy crap. Natalie, I look so hot, I'd fuck me!" I said, continuing to check myself out in the mirror. Natalie's face lit up and she walked over to me.

"Well, you do look hot. But you're not quite a girl yet," she said with a smirk, untying my robe and exposing my body. I scrambled to get the robe back on.


"Oh shush. We're just two girls getting changed, remember? I mean, you certainly don't look like a boy now."

I looked at the blonde wearing the pink robe in the mirror. Yeah, not much of a guy right now am I?

"You need a girl name too. I don't think I can go around calling you Andrew, or even Andy. We could stick to something closer to your name? Or we could just go wild with it. Call you Lyla or Brittany or Cinnamon."

"Cinnamon? Really?" I asked, rolling my eyes.

"Okay fine. Something more normal."

"I think closer to my name is better. If it's close to my name, I'll probably be able to remember it better," I said.

"Hmmm that's a good point...Andrea?" she asked.

"Nah, my cousin's named Andrea. Too weird."


I mulled it over for a bit. Anna. I looked back in the mirror. Anna has long blonde hair and long, toned legs.

"Anna. Okay, fuck it. I'm Anna," I said, smiling. Natalie smiled back.

"Well lets get Anna dressed then!" she said. "Shit, and me as well, I can't go out looking like this."

Natalie walked over to her underwear drawer, taking off her bulky sweatshirt as she did, revealing the black bra she was wearing underneath. She bent over, and emerged back with a piece of fabric that she threw at me.

"Here, put these on," she said, motioning to the fabric she threw to me. I held it in my hands, and stretching it out a bit revealed that they were pink panties, trimmed with pink lace.

"Yeah, you can probably get away with wearing my panties because you're pretty thin, but if it comes to clothes there's no way," she said. She pulled down her sweatpants, revealing a black thong. She bent down to reach into her underwear drawer again. I took the panties in my hand, unfurling them so I could find the leg holes. I stepped into one of the leg holes, pulling the panties up my smooth legs. The sensation of the soft, lacy panties moving against my smooth, hairless legs, combined with the visual of Natalie bent over in her thong started to cause a very unladylike tent to form in my robe.

I should say this about Natalie: she's hot. If she wasn't rich, she'd still be popular just by virtue of how hot she is. She had an athletic body that you just couldn't say no to, a product of years spent on the school's soccer team. Her C-cup breasts and toned stomach gave way to similarly toned legs. Her ginger red hair paired perfectly with her pale skin, skin that was even paler than mine. She had an appeal, and she knew it: every guy in our year had been trying to get into her panties since the beginning of high school, and the select few who earned that privilege were not disappointed.

"Getting a little excited there?" Natalie asked, smirking, snapping me out of my trance. I looked down and noticed that my tent was still there in my robe and my panties were around my thighs. Thankfully the robe was long enough to hide my entire crotch area.

"Uhh...okay, it's just all the soft stuff and the good feelings physically...and you're like naked right now!" I exclaimed, motioning to her bra and thong clad body. She giggled.

"Oh, so me being a little naked has you all turned on?" she said, slowly moving towards me.

"uhhh...Natalie...what are you-" I tried to get out before she gently placed a finger over my lips.

"There's nothing to be ashamed of, Anna," she said, reaching under my robe and placing the palm of her hand over the tip of my cock. A drop of precum that had developed over the tip of my cock was now spreading across her palm.

"'s me...Andy..."

"Shhhhh. I don't know who Andy is. I'm looking at a girl named Anna right now, wearing the fluffy pink robe with the blonde hair," she said, putting her other hand on me.

Natalie pushed me onto the bed and climbed in right on top of me. She pulled the panties that were around my thighs off of my legs and threw them aside. She kissed me deeply, her tongue flooding my mouth as her hand strayed up my robe, along my smooth thighs, back to my hard, wet cock. She scooped the precum from my cock and rubbed it along the length of my shaft, lubing up all 6 inches of my cock. I moaned as she played with the length of my shaft, and she squeeze my throbbing head with her hand.

"Do you want me to eat you out, Anna?" she asked, her hand never leaving my cock. I nodded, biting my lip, focusing on the pleasure radiating from my crotch. A wicked smile crept across Natalie's lips. She untied my robe and pushed me further back on the bed, my head now resting against her pillows. She climbed up the bed until she reached me, and I quickly spread my legs. Her head went between my legs, which she placed on her shoulders. She slowly started to kiss up my smooth thighs, nibbling on my bare skin. My cock grew even harder in response, and I felt my breath shorten.

Natalie kissed her way to the base of my hard, wet cock. She extended her tongue, and slowly licked her way up the shaft, going all the way to the head before giving the tip of my cock a light kiss. I shivered in delight before she pulled her mouth away, leaving a long trail of precum and saliva coming from her soft pink lips. She lowered her head back down to my cock, and my cock craved her touch. She opened her lips slightly and took the head into her mouth, enveloping the entire tip of my cock. She slowly flickered her tongue, moving it from the underside of my head to the top of the head. I softly moaned with each movement of Natalie's tongue.

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