Prom? Ch. 04


Hey everyone, Chapter 4 is here! It's a bit longer than the others. If you liked the story, feel free to leave me a comment or a rating. Thank you!


I slowly faded into consciousness as beams of sunlight shone through the curtains of my bedroom window. I lifted the sheet from my body and noticed a bulge in my pajama shorts, and I rolled my eyes. My poor cock had been taking a beating these past few days, and I just couldn't bring myself to do anything. I thought about my usual turn-offs as a rolled to look at my alarm clock, noticing that the time was 11:30 in the morning. For the first morning since I had transformed into Anna, Natalie was not in bed with me.

Natalie and I had sex for the first time almost a week ago, back when I had turned into Anna for the first time. We settled into a routine after that, with either me sleeping at her house or her sleeping at my house. It was easy enough that way, considering my parents were away and her parents were barely home. Mornings would start with a quickie, and after showering and eating breakfast Natalie would teach me any number of "girl" related things to me: fashion, makeup, anything she could think of. In the afternoon we'd go out, and she always made me dress as Anna. Usually it was something small, like a trip to the mall or a coffee shop. On one occasion we went out to a fancy meal with Mike; the two of us wore little black dresses while Mike wore a suit.

Natalie also insisted that Mike and I go out together, sometimes with her and sometimes on our own. She said that it made us seem "like we're a couple" and will help us "get comfortable with being together." At first it was awkward as can be, but after some encouragement from Natalie, we both started to get more comfortable with the idea. Mike and I would hold hands when we walked, or sometimes he would wrap his arm around me at the movies. I was beginning to enjoy being treated like his girlfriend, and it seemed to me that Mike liked having a girl with him again.

Mike and I hadn't kissed or anything at that point, but sometimes I'd find my mind drifting back to him in ways I had never imagined. Ever since I had transformed into Anna for the first time, I was starting to think of Mike in a sexual context. He was big and strong, and could certainly manhandle me in bed. Sometimes stray thoughts about him would enter my mind and I'd find myself having to think about baseball to calm down the bulge in my panties.

Nights were reserved for Natalie and I. Every single night we were having sex, always with me made up/dressed as Anna. We were having sex everywhere: her bedroom, my bedroom, her poolhouse, hell even in her pool. I was going through packages of condoms at breakneck speed: she had been on the pill since she was 16, but given the amount of times I was fucking her we wanted to be sure. In addition, every blowjob she had been giving me had involved her fingering me. At first it was just one finger, but over the past few days she had progressed to having up to four fingers up my ass at once. This, of course, led to me having mind blowing orgasms, leaving me spasming and absolutely breathless.

I put on a large sweatshirt over the tank top that I was wearing. The sweatshirt was so large that it came down to below my pajama shorts, giving the illusion that I wasn't wearing pants. I took a minute to admire this look before leaving my bedroom and going downstairs, tying my hair into a bun as I walked.

I entered the kitchen and saw Natalie sitting at the kitchen table. Two identical plates of toast and half of a grapefruit sat next to each other on the table, along with cups of coffee and orange juice.

"Come," she said, "sit. Light breakfast this morning. Don't want you getting all bloated in your dress."

"Oh please," I said, sitting down. I raised my leg up so it was practically on the table. "Like this could get bloated after one meal." I caught a glimpse of a smile before she took a sip of coffee.

We sat silently for a bit, the only noises in the room being the gentle hum of the refrigerator and the occasional crunch of toast when one of us would take a bite.

"Natalie?" I asked after finishing my coffee.

"What's up?" she said, looking up from her phone.

"What is all of this?"

"What do you mean?"

"This. All of this. Playing house, you and me. The sex. Anna. What is all of this?" I asked. Natalie sighed and put her phone down on the table.

"I guess it's time we have this talk." she said, sitting up straight in her chair.

"You've always been my best friend, Andy. Ever since we were kids, I've trusted you and told you everything. And you've always been there for me. And since you know everything about me, you know about my...thing...that I had with Jade Garcia during the summer before junior year? Well, seeing you all dressed up as Anna kind of reignited those feelings again. And when you're Anna, you look nothing like Andy. So I guess it's easier to just...not think of you as my best friend, but rather as my hot girl friend," she said. She paused and took a long sip of coffee.

"So it's mainly sexual?" I asked, not quite sure what she was trying to say to me.

"Yes, exactly. I see you as a hot girl. Who's packing a cock, of course," she said, winking. We both briefly broke into giggles, before reverting back into silence.

"So like...we're not a couple or anything, right?" I asked, finishing my toast.

"No, hell no," she said. "We're just fuckbuddies. Lesbian fuckbuddies. Or bisexual. Whatever."

"Okay good," I said, relieved. "That would have been a challenge. With you going to Berkeley and me going to New York for college and everything."

"Oh yeah, no, of course not. You could suck Mike's cock tonight and I wouldn't even care," she said, a devilish grin crossing her face.


"What? It's obvious," she said. "He told me about that time at the movies when he put his arm around you and you immediately crossed your legs. My favorite part was when he asked you what was wrong and you just blurted out 'BASEBALL!'."

"Oh...shit," I said, instantly turning beet red. Natalie started laughing at my admitting to getting a boner with Mike.

"I wouldn't worry about it though. He said it was kind of cute, and if he's being perfectly honest...he was thinking about baseball as well," she said, winking at me.


It was two hours before prom and I was sitting on Natalie's bed. I was wearing a white lacy strapless bra, a pair of white panties with black lace trim, and a single white garter on my left leg. I had shaved that morning, so the garter felt especially good on my smooth leg. I had no idea why I was wearing it, but Natalie insisted that I did.

Natalie had called up Alexander Tan, a friend of her parents and one of the best beauty gurus in the Bay Area, and told him that she and her "friend" needed hair and makeup for the night. Alexander immediately reserved space for us at his salon, where he had a squad of workers ready to make me pretty. My blonde hair had been curled and braided into a half updo, simultaneously giving me a classy look with the braided portion and a sexy look with the long curls going down my upper back. They then went to work on my face, applying foundation and contouring wherever it was seen as necessary. Next came eyeshadow, a cat-eye eyeliner, and mascara, in addition to a pair of false eyelashes that were glued on, giving my blue eyes an even sexier appearance. Alexander himself took over and applied a hint of blush and a sexy red lipstick that matched the color of my dress.

Natalie returned to the bedroom, holding my dress in her hands. Her makeup was similar to mine, albeit with a pink color scheme. Her red hair was in an full updo, with a few curly locks intentionally falling down either side of her face. Her dress was pink to match her makeup, and it was tight in all the perfect places.

I took the dress from her hands and felt a hard object buried in the fabric. I dug through the dress until I found a metal flask. I unscrewed the cap and took a sniff, and the burning sensation in my nostrils told me it was vodka.

"For your garter," Natalie said. She knocked on her thigh, and the contact of knuckles to metal indicated that she had a flask strapped to her thigh as well. At least I didn't have to do this shit sober.

"Can't I just put this in my purse?" I protested. "I put my flask for our prom in my breast pocket."

"And that's good," she said, "but that's...boring. C'mon, live a little."

I rolled my eyes and took a quick sip from the flask, much to Natalie's delight. I tucked the flask into my garter and stepped into my red dress, zipping up the side once I had adjusted it properly. Natalie had altered it slightly, making the neckline just a little bit higher. I may have had C cup breast forms in my bra, but I certainly didn't have the cleavage to make up for it, which the higher neckline hid perfectly. From a casual observer's point of view, my breasts looked perky and natural. The rest of the dress wrapped perfectly around my slight curves before becoming a bit looser at my hips, leading into the long skirt that went down to my ankles, with the high slit on the right side, exposing my right leg. The 4" heels made my ass stick out, the fabric wrapping even tighter around my pert and firm butt. Natalie gave it a slap, and watched it jiggle a little bit in the mirror. I used to hate having a feminine body, but seeing it in my prom dress made me wish my curves were more pronounced.

I was snapped out of my trance when I heard the doorbell ring. Natalie went to her computer, bringing up the software that controlled the security cameras in her house. She went to the front door camera and saw Mike wearing a tuxedo, with a slightly shorter tuxedo clad asian guy.

"Looks like our dates are here!" Natalie said. I winced. I was used to doing theater, sometimes performing in front of hundreds of people on stage. This, however, was like no performance I had ever done.

Natalie and I went down the stairs, opening up the front door, allowing Mike and Cameron to see us for the first time. I swear I could see Mike's jaw drop when he got his first glimpse at me, the blonde bombshell in the sexy red dress. He quickly returned to normal, however, so as to not look like a buffoon in front of his friend.

"Hi Cameron! Hi Mike!" Natalie said, offering her hand to Cameron.

"Hey Nat, hope we're not late or anything. Who is your friend over here?" Cameron asked, shifting his eyes towards me.

"Oh, her? Well, that's my-"

"Friend, Annabelle. But you can call me Anna, for short," I said, giving him a wink and offering him my hand. He took my hand and shook it a little bit, his calm demeanor disturbed by my attempted flirtation. Clearly, it had worked to some degree.

"Hey now, man, don't steal my girl," Mike joked, causing all four of us to laugh. Mike looked over to me and shot me a winking, and I smiled in affirmation.

"So, might I suggest we come inside and do shots while we wait for the Uber?" Natalie suggested. Cameron took Natalie's hand and I held on to Mike arm as he walked through the door.

"So, we're going to a pregame first?" I said, dropping my "Anna" voice for a minute.

"Yep. Kid who's hosting it has a massive house, even bigger than Natalie's. Everyone who's going to prom is going to be there, maybe even some crashers who just show up."

"Wow. Okay." I said.

"What? Are you, like, nervous or something? You shouldn't. You look really hot."

"Yeah, that's what I'm nervous about. Some petty bitch might get insecure or something. Or maybe Ashley Witten-"

"Ashley Witten is going. Shit. I totally forgot," Mike said.

"Oh well. Can't control that. Good thing I got my good friend with me," I said, giving a knock on the flash attached to the garter on my left thigh.

"Jeez, Andy, you're bringing a flask with you? How much booze is in there?"

"Anna. That's Anna, to you," I said, putting my girl voice back on. "And not that much. Don't worry. You know my liver is strong."

"God. I hope so. The last thing I need is for you to get drunk and do something stupid," he said, grimacing at the thought.

"Relax," I said, wrapping my arm around him, "I can take care of myself. Who knows, maybe if you let me take care of myself all night, you might get a little reward." I winked at him and took him by the hand, leading him into the kitchen.

The Uber wasn't that far away, so we only had time to take one doubleshot of tequila each before the black Escalade pulled into Natalie's semicircular stone driveway. The four of us piled in, Cameron sitting in the front passenger seat and Natalie, Mike and I in the backseat, me sitting between Natalie and Mike. The car ride to the pregame was pretty raucous, with the four of us gleefully dancing, aided by the shot we had just had. The driver was fun too, and he became jubilant when he learned we were going to prom. He let us play music from our phones on the stereo, and even joined in on our goofy dances. I almost didn't want to leave the car, but the promise of more vodka at the pregame forced me out of the car.

My heels clicked against the pavement as the four of us walked up the driveway. I had grown accustomed to walking in heels, but I still found myself holding Mike's arm, at least for a little stability. Even though I was around 6 feet tall in my heels, I still felt dwarfed by Mike's massive frame. He towered over me.

We finally reached the front door and climbed up the stone steps, passing cigarette and marijuana smokers alike. As I was walking with Mike, guys were offering me hits of whatever they had, whether it be a blunt, joint, or Marlboro. I took puffs from the joint and the blunt; I'm not one to pass up free weed. However, I made sure to hang on to Mike the whole time, letting him know that I meant nothing by it at all.

I walked into the house before Mike and immediately saw Natalie waving me down, facing a circle of girls. I came over, nervous about separating from Mike so quickly. That feeling was quickly shaken, partially by a newfound confidence in myself being the hottest girl in the room, in addition to the alcohol going through my system. I sized up the other girls in the group: one black girl and two white girls, one brunette and one blonde. They were all at least a head shorter than me, given that our heels cancelled each other out.

"Anna, this is Kiara, Jenna, and Kelly," she said, motioning at each of the girls. "They're cheerleaders at Polk, and I used to cheer with them back in elementary school."

"Oh wow, that's really cool!" I said, putting on my girl voice again. I breathed a little easier, knowing that at least my girl voice was up to par.

"So, Anna, how do you know Natalie?" Jenna, the brunette, said.

"Yeah, she never mentioned your name, like, ever," the blonde, Kelly, said.

"I'm just a really old friend of hers. We knew each other way, way back. I moved to Berkeley awhile ago, but we still talk a bunch, and when she asked me to be her friend's date to a prom she was also attending, I figured it'd give me a good excuse to visit," I said.

"Oh wow, Berkeley! Are you going there in the fall?" Kiara asked.

"Nope, I'm actually not," I said. "I applied there and got accepted, but I didn't feel like going."

"Really?" Kelly asked. "Well, then, where are you going?"

"UCLA. On an acting scholarship," I said with a grin. I could hear Natalie choke on her drink next to me, coughing lightly for a second before regaining her composure.

"Oh wow!" Jenna exclaimed.

"Good job!" Kiara said, smiling.

"I'm so jealous!" Kelly said. For some reason, only Kiara's remarks had felt genuine. Jenna and Kelly's words dripped of envy.

"Yep, well, you should be. She's a great actress. In fact, she's SUCH a great actress," Natalie said, glaring at me. I chuckled a bit.

"Alright, we better find our dates. See you around Natalie and...Anna," Jenna said, and the three of them turned to leave, with Kiara turning around and giving me a light wave.

"Oh. My. God. Did you see that?!" I exclaimed, almost jumping out of my heels.

"Yeah, I did see that. Acting for UCLA? What the heck?"

"Oh, c'mon. It's a little white lie. Who does it hurt?" I asked. She rolled her eyes.

"Okay, fine. Just don't lie too much, or make yourself look too good. You already literally look prettier than like 99% of the girls here, so you already have made all those alpha bitches feel insecure."

" I really prettier than 99% of the girls here?" I said, raising an eyebrow.

"Yeah, pretty much. It's 99% and not 100% because I'm here, and I'm still prettier than you, you big bitch," she said, winking at me.

"Who's a big bitch here?" I heard Mike say from behind me. He wrapped his arm around me and put a red cup into my hand. I briefly looked down at the red liquid inside the cup before raising it to my lips and taking a sip, leaving a little ring of red lipstick on the rim of the cup. Vodka Cranberry. I took another sip.

"Well, apparently your little girlfriend over here is going to UCLA on an acting scholarship," Natalie said.

"Oh wow, that's a lot. Might want to tone it down a little bit," Mike said.

"That's what I'm saying!" Natalie cried.

"Okay! Relax guys," I said, pausing to take another sip of my drink. "That's going to be my big lie for the night. Nothing crazy anymore. I'll make sure everything's okay." Natalie and Mike nodded in agreement.

I actually almost upheld that agreement. Luckily, I had chosen to lie about something that I knew pretty well: acting. Therefore, I was able to at least keep up the lie pretty well. Still, I embellished a little bit when I felt it was necessary. I only told one outright lie: one girl who was particularly drunk was bragging to me about how her modeling career was going to take off once she graduated high school. Just to spite her, I decided to tell her that I was already a model, and that although I was unsigned as of right now, I had done catalogue and print modeling before, and I was sure that my career would take off once I moved to LA in the fall. At first, she didn't believe me, but then I went into my phone and showed her my "headshot," which was really just a picture that Natalie had randomly decided to take of me when I was dressed as Anna one night. The way Natalie shot it made it look like an actual, professional headshot. The girl was so exasperated that she dropped her almost drink on the floor. Well, it was partially her exasperation, and partially her drunk self losing her grip on the cup.

When it came time to go to prom, a caravan of limousines lined the driveway of the mansion. I found Mike, who led me to a limo that already contained Natalie and Cameron. I was told that we were going to be riding with some of Cameron's friends on the basketball team. I was happy to find out that Kiara was dating one of those basketball players, and she immediately sat next to me, giving me a light hug. There were ten of us: five guys, four on the basketball team and Mike the lone football player: four girls, one of whom was Natalie: and then whatever the hell I was, in my red dress with my hair and makeup all done. At least my cock was tucked away.

We shared some bottles of champagne that one of the basketball players had brought onto the limo, and needless to say, by the time we got to the country club I was stumbling around on the pavement. It reached a point that I required Mike's arm for stability, not just as a vanity display.

"Jeez, Ann, you're drunk aren't you?" Mike asked.

"That's Annaaa to you, miiister," I half-slurred. I immediately realized how drunk I was, and suddenly was hyperalert and aware.

"Oh, crap. I need to fix this," I said to Mike. I stood a little taller, keeping my back a little straighter, making sure I didn't look like some boozy bimbo.

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