Prom? Ch. 02

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Natalie helps Anna shop for a prom dress.
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Part 2 of the 5 part series

Updated 06/08/2023
Created 06/07/2017
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I hope you guys enjoyed Chapter 2! I know it wasn't as sexual as the first part, but trust me, we'll get there. Chapters 3 is already in the works, and I hope to have it completed soon! If you liked the story, feel free to leave me a comment or a rating. Thank you!

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The red Mercedes E class sedan raced down the 580, going a cool 70 miles per hour. The driver of the car, Natalie, confidently powered the luxury car in and out of lanes, bobbing and weaving through traffic with a crisp edge. In the back seat was Mike, nervously tugging at his collar and looking out of the window. I was sitting in the passenger seat, me, Andy. Only I wasn't Andy anymore. I had just been transformed into a girl named Anna.

After I had finished up being blown by Natalie in her bedroom, the fact still remained that I needed to get a prom dress. Natalie opened the box of clothes that her sister had left behind. She sifted through the garments as I cleaned the cum off of my stomach and chest. I stood back up and found my panties, and this time I pulled them all the way up my smooth legs until my soft cock was encased in the fabric. I found that while my cock was not making nearly as big of a bulge as it did when I was hard, it still created a slight bulge. Natalie frowned when she saw the bulge, and finally spoke for the first time since she made me cum.

"Ah shit, still poking out? Thought the blowjob would take care of that. Give me 15 minutes," she said, walking out of the room, phone in hand. I sighed and sat down on the bed, taking a casual glance through the offerings of the cardboard box. Natalie returned soon thereafter with medical tape and a pair of scissors in her hands.

"Uh, what's going on?" I asked. Goosebumps formed along my thighs, and I suddenly felt cold. My balls started to retreat inside of my body as I took a glance at the shiny blades of the scissors.

"Well, from my watching of RuPaul's Drag Race, cocks can be tucked away to make a flat front. Looks a lot better than a bulge in the front," she said, motioning for me to stand in front of her.

"Oh, and you're going to do it just like that?" I asked, walking towards where she was telling me to stand.

"Relax. I watched a youtube video. I can do this," she said. Natalie pulled my panties down to my knees and reached her hand between my legs.

"Okay...so I'm just going to do a little bit of this..."

"OH JESUS"

"Oops. Yeah, sorry. Too forceful? Let me try this," she said, fondling and gripping at my balls. Her hands eventually coaxed one of my testes to retreat up inside me, and the other one soon followed. She took my cock and folded it back, taking the place of where my sack previously was. A few pieces of tape kept my tuck job together, and Natalie pulled my panties back up, smiling when she saw her finished work.

I walked from my spot in front of Natalie to the full length mirror I had first seen myself in an hour ago. I looked at my reflection in the mirror again, and the blonde girl was staring back at me. This time, the girl had no bulge in her panties, nothing hanging between her legs. This girl had a smooth front to her panties. That girl, of course, was me, Anna.

The last trace of Andy within me had disappeared. Now, the person in the mirror looked like a hot, but remarkably flat-chested, blonde bombshell, with narrow, petite shoulders and long, shapely legs, connected to an admittedly large and rather bubble shaped rear end. I reveled in the knowledge that Anna had taken over, before I let out a quite uncouth belch from my red-painted lips.

Yep, Andy was still there.

Natalie handed me a pink bra, a perfect match to the lace trimmed pink panties I was wearing. "I believe you'll be needing one of these too."

"Yeah, right. Me and my flat chest."

"I wouldn't be so sure about that," Natalie said with a wink. I took the bra from her hands and slid the straps up my arms. I struggled to hook the two hooks in the back, but after awhile Natalie gave me some help. After the bra was fastened, Natalie produced two realistic looking silicone breast forms, filling out the cups of the c cup sized bra. I almost fell forward as my balance was altered by these new weights on my chest.

"Yeah, not so easy having tits, is it?" Natalie said, giggling.

"Hey, shut up. These things feel weird."

"Yeah, for you. I'm used to it," she said, winking. I rolled my eyes and went back to checking myself out in the mirror. Natalie held dresses, skirts and tops in front of me to get a sense of how they'd look on me. She finally produced a red dress that was to her liking, and took it off the hanger.

The red dress was a sleeveless skater dress, tight in my chest and waist while flaring out at my hips. The back was partially open, and the hemline went to about a few inches above my knee, allowing my legs to be on display. My fake tits filled out the high neckline perfectly, and no visible cleavage was out, allowing me to keep my secret. I spun around in the dress once, and the flowy skirt twirled in tune with me.

"Having fun with yourself?" Natalie said, smirking.

"Shut up. It's nothing. It's just...just..."

"Dresses are fun?"

"Why yes, madam," I said, doing a mocking little curtsy towards her. A pearl choker and matching pearl ballet flats completed my outfit, along with a purse of "Anna Essentials" that included: makeup, medical tape, panties, tissues, and...a tampon?

I debated the purposes of the tampon in my head as the red sedan weaved through traffic on 580. Natalie was sitting in the front seat, wearing a lime green sundress. Mike was in the back seat, wearing a polo and khaki shorts. And there I was, thighs pressed together, nervously tugging on my pearl necklace and running my hands down the length of my dress.

"Okay, so I figure if I park in the east parking lot we can start with getting your dress first, and then we can go right to shoes," Natalie said, stopping at a red light.

"Um, and how do you expect me to pay for all of this?" I asked.

"I'll take care of it. It's not like I'm struggling with money," Natalie said, revving the engine of the Mercedes before speeding off as the light turned green.

"Are you guys actually doing this? We're not actually doing this. Andy, you're dressed as a girl! This is...ridiculous. Just absolutely ridiculous!" Mike said from the backseat. I could see little beads of sweat forming on his brow.

"Of course we are! Look Mike, think of it like this: the person you're looking at in the front seat is Anna, she's your prom date, and we're just going to get her a prom dress. Just treat her like you would any other girl, man. Unless you think she's hot or something," Natalie said with a smirk.

"NO NO NO NO NO. No. Not hot. Just...shutup okay? Andy, you okay with this too?" Mike asked.

"I don't know who Andy is, sweetie. My name's Anna," I said in my best girl voice, earning me an eye roll from Mike. Years of voice training for theater had given me the ability to disguise my voice with relative ease, and I could go both an octave higher or lower than my usual vocal range, which was already on the higher pitched side.

Natalie pulled the car into the open air mall's parking lot, parking her car a row away from the Nordstrom entrance.

"Okay, we need to get a backstory on you. Let's say you're my...cousin?"

"Cousin? Really?"

"Friend. Old friend. From...Berkeley," Mike piped in, referencing the city nearly half an hour away. It was the perfect distance for a cover story, plus I was familiar with the area. "You kind of look like a Berkeley girl, anyway."

"Oh do I now? And what does that mean?" I teased, batting my long eyelashes at Mike.

"SHUTUP. You just...look like a hot blonde is all. Shutup. Let's get this over with," Mike said, quickly opening the door and going outside. Natalie and I giggled to each other, until my door was opened from the outside by Mike.

"Holding doors now, are we?" Natalie asked, grinning. Mike immediately turned beet red.

"It's instinct, I swear! My mom raised me right."

"Sure, raised you to open doors for hot blondes. Don't have to justify yourself to me, Anna's quite a hottie," Natalie said, giving me a wink. I briefly thought back to just a few hours before, when Natalie's glossy lips were wrapped around my hard cock: the way she licked and sucked at my cock, with her head between my thighs, how she made me cum like never before...

Shit. I felt a stirring start to occur in my panties. My thoughts instantly went back to more mundane things: politics, the Oakland A's standings in the AL West, recipes. Anything that could stop the thoughts of my hot redheaded friend Natalie sucking on my cock.

It was a cloudless day in the Bay Area, and I felt the warmth of the sun on my long, bare legs. I got out of the car like I normally would, and Mike snickered at me.

"Nice panties," he said. This time it was me who was turning beet red.

"Jesus Anna, you flashed him already? You need to learn to stop being such a tease," Natalie said, giggling.

"Shut up! I didn't realize I had to change how I got out of a freakin car just because I'm a girl now!" I countered.

"Clearly I still have much to teach you if we're going to prevent you from flashing your panties again," Natalie said. I rolled my eyes and the three of us proceeded into Nordstrom.

Despite the mall being two towns over from us, I had been to this Nordstrom location before; however, nothing could have prepared me for the exploration into the women's section of the store. The clothing options seemed so much more abundant: everywhere I turned I was greeted with different garments in all colors and styles, a stark contrast from the relatively boring men's section one floor above us.

"Okay Mike, I'm going to go with Anna to find a dress. You can go...I don't know. Do something else. Just don't get lost," Natalie said.

"Wait, I don't have to be with you guys for the shopping portion of this?" Mike asked, excited as can be.

"Just go. We'll find you later," I said, flicking my wrist and rolling my eyes. Mike gleefully took off to the tech section, leaving Natalie and me in a fit of giggles.

"God, what a typical guy," I said, in a tone that was far too sassy for my comfort. I was adapting somewhat well to my new role as a girl, mimicking Natalie's walk and movements, while retaining my own flair.

"So...what kind of dress do you want? It'd be a bit rude of me to just go and do my thing without getting some input from you," Natalie said, browsing some dresses from a rack. I started to look around and explore. There were all kinds of styles, with all kinds of hemlines and necklines and sleeve configurations.

"Um...what's best for me do you think?" I asked, sifting through some more poofy looking dresses.

"Hmm...well I'd hate for you to hide your legs...but a short dress for prom is a bit odd, especially at Polk. They always do long dresses. So we could maybe get you something with a leg slit? Show off a leg while still keeping it classy," Natalie said, pulling a dress from the rack. I nodded. I guess that was a good idea? I reminded myself that this was not my area of expertise, and I better just stick to Natalie's ideas. She picked a few more dresses for me, carefully holding each one up to my body to get an idea of how it would look.

"Okay so I have, like, five dresses here. Hopefully you'll like one of these. Now if we ca-SHIT! HIDE!" Natalie said, abruptly ducking me down behind a rack of skirts, almost causing me to fall and causing the contents of my purse to spill to the floor

"Jeez Natalie what the hell-"

"SHHH. Quiet. I think I see her."

"Who? See who? What?" I asked as I picked up the things in my purse. At least the tampon hadn't fallen out.

"ASHLEY WITTEN. That bitch. What the fuck is she doing here?"

"Oh shit," I said, moving myself into a position to take a peek above the rack we were hiding behind. I took a quick glimpse and, sure enough, there was Ashley, brunette locks pulled into a tight ponytail, wearing denim shorts and a tank top.

Natalie and Ashley used to actually be pretty good friends. Back in middle school and early high school, they were basically the two queen bitches, the most popular girls in school. However, a rift started to form as Ashley clearly emerged as the bigger bitch of the two, and it all came to a head when Ashley stole Natalie's boyfriend junior year. Well, Ashley won't admit that she did, but she essentially did. Rather than hating each other, Natalie and Ashley instead engaged in fake kindness and pettiness typical of high school girls.

"Okay, here's our plan. We emerge from here, and...uh...go shop someplace else?"

"Jesus Andy, can you think of a better plan?" Natalie snapped.

"Andy? ANDY? Natalie, we can't be doing this Andy shit right now. Ashley could frickin recognize me!" I whispered, almost giving away our position. I felt my heart rate begin to increase.

"Yeah, shit. You're right. Sorry. Okay, Anna, let's just take these dresses and try them on in another department? I'm sure there are fitting rooms somewhere else."

I nodded and gave another peek, and this time Ashley had her back turned, busy hanging up pairs of pants. I gave a nod to Natalie, and we quietly started to make our escape from the women's department.

"OH MY GOD! Natalie?" I heard a voice call from behind us. Natalie audibly groaned and turned around, resigned to the fact that now she'd have to deal with this shit.

"OH MY GOD! Ashley!" Natalie said in her "fake nice" voice. She put extra emphasis on the "Ash" part of Ashley. Natalie and Ashley approached each other and gave each other an incredibly too-friendly hug.

"What are you doing here?" Ashley asked, putting on a similar "fake" voice. I remained silent, not ready to face my first true test as Anna. I could almost feel my pulse without having to use my fingers.

"Oh, we're just shopping for prom dresses. You know how Polk has their prom next week."

"Yes I do! Who are you going with? I'm going with Carlos" Ashley asked.

"Cameron, he plays basketball over there."

"Oh that's exciting! Now, are these dresses for you, or for you...friend?" she asked, turning her eyes towards me.

"Hi, I'm Anna," I said, almost in my guy voice. I recovered just in time and put my feminine voice on. "I'm a really old friend of Natalie's. She said a friend of hers needed a date so I figured why not?"

"Oh that's exciting! Who's your date?" she asked, not quite in the same fake tone that she used with Natalie, but in a tone that still gave off an air of bitchiness.

"Mike is her date," Natalie interjected. "Seeing as he's not going with Jessica anymore."

"Oh yes! It's a shame they split up. She was...really good for him." Ashley said. Natalie and I clearly knew better, considering the whole her-cheating-on-him thing. "Okay, well I'll leave you two ladies to your shopping! Natalie, text me if you want to hang out this weekend." And with that, Ashley turned and walked away.

"Wow. That was close," I said when my pulse finally returned to normal.

"Close? Are you kidding me? She totally bought it! Hook, line and sinker. Are you sure you don't have prior experience doing this?" Natalie said with a wicked smile. I rolled my eyes and made my way to the fitting rooms, telling Natalie to wait inside.

Once I was in the changing room I let out a sigh of relief, which was followed by an overwhelming rush of exhilaration. I had actually passed as a girl! To a girl that I already knew! I chuckled a bit to myself as I took my dress off to try on the dresses.

The first I tried was the turquoise one. It was trimmed and covered in lace, and almost looked like the dress that Elsa wore in the movie Frozen. As much as I'd love to look like a beloved children's character, I'd rather pass on that prom look. The peach dress Natalie picked out looked a bit nicer, but the neckline was far too low for my liking.

Finally, I took the red dress off the hanger. It was quite the number: the dress went down the length of my legs, but a slit that went to my mid thigh exposed my right leg. The dress was pretty tight, showing off my bubble butt and flat stomach. It had a high neckline with an open back, leaving most of the area between my neck and my ass exposed. I looked at myself in the mirror and was absolutely stunned. I looked like a knockout.

Just as I was looking at myself, I felt a familiar stirring in my panties. Right now was the exact opposite time that I wanted to have an erection. I took another look at myself in the mirror, which certainly didn't help things. I was tempted like never before to take my panties off and jerk off to the hot blonde looking at me in the mirror. I kept my cool, though, and once I had my cock back under control I went outside to show Natalie.

"OH. MY. GOD. YOU LOOK SO HOT!" Natalie said as I did a twirl in my dress. The dress clung tight to my body, showing off my curves, both real and fake.

"So, is this the one?" I asked, waiting for a formal confirmation.

"Fuck yes. You look awesome. Hell, I'm jealous for Mike now. Take that off so I can pay for it, I'll be in the shoe department," Natalie said.

I met Natalie in the shoe section, and after giving her the dress and trying on some pairs of shoes, excused myself to the bathroom while Natalie paid for everything. This brought about a new dilemma I hadn't given much thought to: which bathroom do I use? From the outside, I very clearly looked like a girl; going into the men's room in this getup would be ridiculous. Plus, I just wanted to pee right? Should be simple enough. I pushed on the door of the ladies' room.

I was first taken aback by the lack of urinals, but then I remembered that I was in the ladies' room, and nobody here would be peeing standing up. I made my way over to the stalls and saw that 2 of them were occupied, leaving two of them unoccupied. Just as I was about to go into one of the stalls, a woman wearing a hooded sweatshirt and shorts barreled through the bathroom door and went into the stall next to me.

I went into the other stall and locked the door. I sat on the toilet and hiked up my dress and pulled my panties down, exhaling as my cock came out of its previous medically taped position. I let it hang free for a bit, sitting down and leisurely checking my phone. The girl in the stall next to me, however, was having a bit of a struggle. I could hear short, labored breaths coming from the stall. I was on my phone when I heard a sudden thud.

"Oh shit!" I heard the girl in the stall next to me say. I looked down and right at my feet looked to be the contents of a purse: phone, makeup, tissues, all kinds of things on the ground.

"Do you need help?" I asked as I reached for some of the items. I was glad that the stall dividers gave me some privacy, considering my cock was now on full display. I picked up the tissues and stuck just my hand underneath the stall wall, and I felt her hand reach for it.

"Oh yes, please, do you have a tampon? I forgot one this morning and my fucking period started," a female voice in the next stall said to me.

"Sure! Here you go," I said, silently thanking Natalie that she had packed a tampon in my purse. I handed the rest of the items back over to the girl, and as soon as I handed back the phone, the girl opened the stall door and raced out of the bathroom.

Something about that whole encounter seemed off. I debated what had happened as I pulled my panties back up, moving my cock back into position. I left my stall and looked into the stall that had just been occupied. The toilet had not be flushed, and there was no reason for it to be: there was nothing in there but normal toilet water. No toilet paper, no tampon wrapper, not even anything that suggested that the girl next to me had gone to the bathroom. She hadn't even flushed the toilet in the first place. I wanted to investigate further, but knew that I should probably minimize my time spent in the ladies room. I washed my hands and made my way back to where Natalie was.

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