Homecoming Queen Ch. 02

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Allison and Jason continue their relationship.
14.3k words
4.78
33.2k
100

Part 2 of the 3 part series

Updated 06/10/2023
Created 03/01/2021
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AshRynn87
AshRynn87
709 Followers

All Characters in this story are over the age of 18.

*************

It had been two weeks since I went to homecoming as my best friend Jason's date. I spent the following weeks working off the debt I had gotten myself into in purchasing that lingerie set from Victoria's Secret. I was pretty bummed that I no longer had a reason to wear it, but the memories of the night and the dance gave me a warm feeling inside.

Despite all that, I still had a feeling of dread that was eating away at my insides. I had yet to really speak with Jason following the night of the dance. Giving him a blowjob was one thing, but I still couldn't believe we ended up fucking. Hell, I lost my virginity as Allison before I did as Allen. I don't know if that was Jason's first time or not, but just the thought of talking with him about that night and where we go from here gives me heartburn.

I was actually more uncomfortable now, having fucked Jason than I was when I had just shown him the picture of me dressed as a cheerleader. The two weeks of silence had me running all sorts of scenarios in my head, and for every one that turned out pleasant, there were another 10 that ended in disaster. This doesn't even take into consideration that it seemed like Jason's mom recognized me that night.

But finally, when I least expected it, Jason called and asked me to another party. The phone call was short and to the point. He asked me if I'd come as Allison and I said yes. No mentions of what happened that night in his room. No discussions about what this meant for us. I guess I should have been relieved that I didn't have to have that conversation, but it has to happen eventually.

Anyhow, Jason suggested that I again meet at his house and get ready there, but I told him that my parents would be out and that I could just meet him at his house and be ready to go from there. Of course I had no fucking clue what I was going to wear. I had never really expected to go to a high school party as Allison. It was one thing to buy a homecoming dress, but I didn't really have anything casual and cute in my wardrobe. I only had cheap lingerie and a few ill-fitting, slutty dresses.

My older sister was still away at college, so I decided to rummage through her things to see if she left anything behind that I could scavenge. It was slim pick'ns...mostly tee-shirts and a few pairs of jeans. It would have been a fine look, but despite my slim build, I'd never fit in her jeans. But to my luck, at the bottom of the drawer of jeans, I came upon a pair of shiny, black, metallic leggings.

I though to myself, "My ass will look great in these, now I just need to be able to squeeze into them."

I quietly checked the house just to make sure no one was around. I shut the door, locked it, and then quickly dropped my pants and boxers and then slid on the leggings. Well, squeezed into them inch by painful inch was more accurate. When I finally got them up and my meager manhood tucked and smoothed, I feared that they would just be too tight. But the waistband was a perfect fit and didn't cause a muffin top. The thighs were stretched to the limit, but I gave them a few squats and bends and they held perfectly. More importantly, they looked and felt amazing.

I spent a few minutes running my hands over the silky smooth fabric and admiring my curves in the mirror. I was sold. Now I just needed to find the rest of the outfit. I pondered a few tee-shirts and tank tops, but it was really to chilly out for that. My sister had a midriff bearing sweater that looked fabulous with the leggings, but I was too scared to wear that to the party. I settled on a chunky, white, large knit sweater with a cowl neck. This one stopped just below the waistband of the leggings, so it still showed off my legs and ass, but it was still fairly short, so if I reached for something over my head, my belly button would show.

Fortunately, I already had a pair of ankle boots that would go perfectly with the outfit, so I didn't have to do any shopping. I quickly got out of my sister's clothes, folded them up, and stashed them in my overnight bag in the corner of my closet. The next few days were spent debating makeup and accessories. I decided to steal a white tank top from my sister to wear under the sweater in case it got hot.

With much anticipation, it was finally Friday and I was ready to get home from school and begin my transformation. Unfortunately the day dragged on forever, and when I finally got home, my parents were still there. I really wanted to start my makeup and get into my outfit, but instead I was relegated to sitting on the couch and playing Call of Duty until my parents finally left for dinner.

"Allen, are you going to just sit there all night playing video games? I thought you were going to Jason's? I'm glad you too are still finding time to hang out." My mom said.

"Uh, yeah. I'm supposed to head over there in a bit. Just feel like hanging out on the couch for a bit though. It was a long day." I tried to play off my anxiety.

"His mom told me about his homecoming date. Apparently she was very pretty. Judy thought the girl looked familiar but couldn't figure out how. Did you know her?"

Fuck!

"Um, no Mom. I met her that night. She's pretty cute, I guess. Allison, I think." I did my best to play ignorant.

"Oh, well Judy seemed to think that she went to school with you." My mom continued to press for information.

"I didn't ask. I assumed she went to Sandberg." I lied.

"Oh well," my mom continued. "You father and I are leaving in about 30 minutes. You and Jason have a good night."

"Thanks Mom, you too."

"Oh...and ask about Allison. I'd love to be able to help Judy out. Apparently Jason has been pretty quiet about her."

"Yeah Mom, I'd love to get you the dirt on Jason's girlfriend." I said sarcastically.

My mom finally left the room and I let out the breath that I'd been holding in since she first mentioned Allison. This might be a bad idea. Now both Jason's mom and my mom are on my trail. I didn't even know my mom talked to Mrs. Trevino, but I definitely needed to make sure that Allison steered well clear of both of our parents.

At last, my parents left and I could start the process of getting ready. I was shaken from my conversation with my mom, but it still couldn't numb the feeling I got from transforming myself into Allison. I loved every part of becoming her, from the shaving and waxing to the makeup and the clothing. I loved being a woman and they way she made me feel.

After I cleaned up, I put on the pushup bra I got to go with my homecoming dress and a black thong. It was super low cut in the front, and really difficult to get a good tuck, but I was able to manage and get a nice smooth front before pulling on the leggings. I was actually surprised at how well I was able to hide my boy parts. It was getting easier and easier to hide that part of me away. The leggings looked flawless and hugged me in all the right ways.

I threw on the tank top, the sweater, and a chunky black belt around my waist as an accent. I clipped on stud earrings and put on a black choker. I did my hair and makeup, opting to go with the long wavy look again, just like at the dance. This time my makeup was a little more natural. I still did a fair amount of contouring, but I went easier on the eyeshadow and did a neutral lip gloss instead of the pink lipstick. Lastly, I contoured my breasts and gave myself a few spritzes of perfume. Lastly, I threw on some ankle socks and my boots and got ready to head out.

As I walked though the house, I realized I had made a huge mistake. I had dressed in the house before and walked around, but I had never gone outside. My car was parked on the street and I'd have to walk about 100 feet to get to it. The odds of someone seeing me were low, but if one of my neighbors was outside, I was screwed.

I grabbed my overnight bag with clothes for Allen and peeked out the front door. It seemed quiet on the street and I didn't see anyone around. I decided to make a break for it. I practically fell down my front steps as I hurried to the car, getting into the passenger side so I could play it off as being a girlfriend in case anyone spotted me.

I sat in the car, checked my surroundings, and then hopped over the center console to get in the driver's seat. It looked as if I had gotten away with my gambit and I hoped I wouldn't have to explain anything to anyone the next day. I started up my hunk of junk and headed off to Jason's. This night had already started off as quite the adventure. I hoped it would be a little less stressful from here out.

Unfortunately, that wouldn't be the case. As I pulled up to Jason's house, his parents' car was still in the driveway. I kept driving past and pulled over a few blocks down.

"Well what the fuck do I do now?" I said aloud.

I pulled out my cell and texted Jason.

"Your parents are still home?"

It took him a few agonizing minutes but he finally responded.

"Sorry"

"They haven't left yet."

"Can you wait down the block?"

Great. I'm stuck hiding in my own car until his parents leave, but I guess its better than running into Judy again. I'm not so sure I'd be able to keep her off my scent for long.

"OK"

"Let me know when to come in."

I sat in my car for another 20 minutes, reapplying my makeup, going over in my head what I would say to Jason, trying to figure out how to keep Allison a secret from our parents. Finally, Jason texted back.

"They're gone."

I drove back to the house and parked on the street. I gathered all my courage and my bag and headed to the door. Normally I'd just walk in without knocking, but decided that was a privilege for Allen, not Allison, so I rang the doorbell.

Jason answered after a minute.

"Shit, you know you can just come in. You had me thinking someone else was here." He said with a sigh of relief.

"Sorry," I frowned. "Just wanted to make sure."

I followed him through the door and entered the front room.

"Damn, you look amazing." Jason complimented. "I was wondering what you were going to wear tonight."

"Do you think its okay?" I asked. "I wanted to be casual but cute."

"Yeah, you nailed it. I can't wait to show you off." He replied.

"Um, thanks. I think." I said with a grimace.

"Sorry, I didn't mean it like that," Jason back-pedaled, "I just love how fashionable you are. Never would have guessed until you showed me."

"Apology accepted," I said with a polite nod, even though I was still a bit peeved with his cavalier attitude towards me. "We heading out, or staying here for a bit?"

"Let's go in case my parents make a surprise return again." Jason urged.

I laughed, "That sounds like an excellent plan."

Jason led me to the car and held open my door for me. We both got in and he proceeded to drive us to the party.

"Are we going to Dan's house again?" I asked.

"Um, no." Jason replied as I looked his way. "This party is at Jenny's house. The, uh, girl that Katy thought you were."

Jason all of a sudden wavered in confidence and sounded nervous.

"Something bothering you?" I asked.

"I didn't know how you'd feel about that." He responded, sheepishly.

"So you figured the best plan was to get me in the car and hope I didn't find out?" I laughed. "Don't worry, going to Jennifer's house doesn't bother me...but you hiding it from me has me concerned."

"Sorry," Jason said, looking like a scolded dog.

"I guess there's a few things we need to talk about, huh?" I said as I side-eyed Jason.

"Probably." He admitted.

The drive was short, but we got a few things out of the way, the big one being that our parents were getting a little close to sniffing me out. It was probably best to tell Jason's mom that Jason wasn't seeing Allison anymore. Unfortunately the chat about how this would continue, if it would continue, had to wait for another day. But if I was going to continue seeing Jason as Allison, I didn't want to be his old buddy playing in a dress. I wanted him to treat me as if I was always Allison. That needed longer than a drive across town.

I perked up as we pulled up to the party, however. I was excited to be back out as Allison, and I was happy that I'd get to see some of the girls that I had met at the dance.

As Jason and I walked in, Katy saw us from across the room and squealed.

She yelled out, "Allison!" and came bowling towards me, knocking a poor girl out of the way with a hip check that a hockey defenseman would be proud of.

Katy rushed up to me and gave me a huge hug.

"Allison! I was wondering if we'd ever get to see you again!" She exclaimed before turning to Jason. "You haven't been hiding her away from us, have you Jason?"

I butted in. "No, I've been pretty busy with work, and it is a bit of a ride out here from my house. But it's nice to know I'm welcome."

"Of course!" She practically yelled.

Katy grabbed me by the wrist and pulled me from Jason yet again, but he let me go without too much of a fight. I couldn't blame him. Katy seemed like a girl you just had to let do what she was going to do, lest you face her wrath. I was glad she liked me.

Katy reintroduced me to all of the girls that I had met at the dance. We chatted and I was happy to answer everyone's questions. Katy insisted on getting my number and hanging out again sometime. I happily exchanged numbers, but deep down I was nervous about a continued friendship with this girl. It was one thing keeping this charade up with mine and Jason's parents, but adding another friendship would take maintaining my female persona to the next level.

I eventually grabbed a drink and went back to talk to Jason after I caught him and a few of the guys eyeing me from across the room.

"You boys see something you like?" I said with a wink as I sidled up to Jason.

Jason smiled. "Just pointing out to the guys how amazing you look." He said.

"Yeah, and wondering why you don't come around here more often." Said a boy named Derek.

I made a serious face. "Well, I hate to break it to you, but I do have a life outside your school and your little parties."

I enjoyed our little back and forth. It made me feel desired but in control at the same time. I loved my newfound confidence as Allison. As Allen I'd have skulked in a corner until it was time to leave, just the weird dude that tagged along with the new kid. As Allison I was an attention whore and I liked it. I gave Jason a hard time, but secretly I liked that he wanted to show me off. I loved that all the guys eyed me when their girlfriends weren't looking. If only they knew the truth!

I was becoming more and more comfortable with myself. I flirted with Jason and even teased some of the other boys. We danced to a few songs. I even stole a kiss or two from Jason throughout the evening. We were all having a great time and I felt completely natural as Allison.

A few people had started to leave and only a few people remained, including Katy, Dan, Jennifer, Jason, and I. Dan was pretty drunk and kept trying everyone to play Truth or Dare. It was obvious he had a motive, but we eventually relented to his pestering just to get him to shut up.

The game was mostly harmless. Just high schoolers probing each other about what they've done sexually, all of it very tame compared to what Jason and I did a few weeks ago. After a few rounds, I suggested to Jason that we head home, but Dan stopped me as I went to get up.

"Whoa, whoa, whoa!" He slurred. "You can't leave yet, it's your turn Allison."

"I think we'll all live, and I think you need a bed." I laughed.

"Nope! Nope! You can't leave!" He yelled.

I rolled my eyes and sat back down.

"Okay, let's get this over with." I sighed.

Dan grinned. "I dare you to kiss Katy...with tongue."

"Ah, I see." I laughed. "Was that the whole point of this?"

Dan remained quiet, but Jason finally spoke up.

"Dan, I uh, don't think that's a great idea." Jason mumbled.

Katy lept up. "Shut up Jason! Allison can decide for herself."

It was clear that she was eager. She may have even put Dan up to it.

I looked at Jason, "You afraid she's gonna steal me away from you?" I egged him on.

"No, it's just..."

I knew what it was, but he couldn't tell everyone I was a guy. So he shut his mouth. I put a hand on his thigh.

"Just sit back and enjoy." I comforted him.

I crawled on all fours to meet Katy in the middle of ourittle circle, putting on a show for everyone. I reached up to her face with my left hand and brought my lips to hers. Her bottom lip settled between mine as I nibbled on it and took in her scent. She was intoxicating. We smiled into each other and then I grabbed her head from behind and put my tongue in her mouth. She attacked my mouth with a ferocity I'd never experienced.

Dan elbowed Jason and guffawed at the sight. Katy and I put on the show for about 30 seconds before finally backing away from one another, never breaking eye contact until we sat back down.

"Holy fuck that was hot!" yelled Dan.

I grabbed Jason by the hand and pulled him to his feet.

"Come on babe, let's get outta here." I said, before looking at Katy. "Katy, that was fun! Call me sometime."

She gave me a big smile. "Definitely! You two enjoy the rest of the night."

"You too," I said with a wink as I nodded at Dan.

He was clearly all worked up after seeing our little performance. I had to admit, I was a little turned on and I was excited to get Jason back to his house. From the look in his eyes, he had the same idea. I held his hand and led him out the front door. Jason turned around to close it behind us and when he turned back to me, I wrapped both arms around his neck, stood on my tip toes, and planted a huge kiss on his lips. Jason put both of his hands on my ass and pulled me into him.

After a minute or so of making out on Jennifer's front porch, I finally broke the kiss and pulled away.

"Wow, what was that for?" Jason exclaimed.

"I saw how you were looking at me after I kissed Katy. Thought you might be a little jealous...all better?" I said with a giggle.

"Yeah, definitely."

"Come on stud, get me home." I nodded toward the car.

Jason couldn't get me to the car and back to his house fast enough. He hadn't had anything to drink, but I still had to tell him several times to slow down. His bed wasn't going anywhere and we needed to make sure his parents weren't awake before I came inside.

Speed racer made it back to his house in half the time it took to get there. We walked up the steps to his front door. The lights were out, but I was still nervous about running into Mrs. Trevino, so I told Jason to go inside and make sure the coast was clear. Jason opened the door with a slight creak and looked though the living room and down the hall towards his parents room. Looks clear he whispered out to me.

I popped inside and scurried down the stairs. Halfway down I was wishing I had taken my boots off as I tried ever so hard to silence my heels as they hit the wooden steps. Fortunately, I wasn't drunk and giggling like last time. We got down the stairs and I sprinted into Jason's room, closing the door behind us and locking it.

"Who's in a hurry now?" Laughed Jason.

"Sorry," I said with a smirk. "I'm still a little spooked from running into your Mom. Even moreso now that my Mom is asking around."

"I guess I'll just need to keep you quiet."

Jason approached slowly. I finally relaxed and enjoyed the sight of him. I'd never really considered how handsome he was, but now as all 6'1" of him strutted toward me in his designer jeans and button-up shirt with the sleeves rolled up, I could feel my juices flowing and I involuntarily licked my lips. He wrapped me in his big arms and again lifted be by my ass, pulling my lips up to his. I craned my neck and again stood on my toes as he supported me.

AshRynn87
AshRynn87
709 Followers