Homecoming Queen
My phone buzzes and I give it a brief glance out of habit.
"Holy shit, it's Jason." I say aloud.
And it's not just a text, he's actually calling me. I reach to grab the glowing device, but hold it at a distance as if it were a venomous snake. I never expected to hear from him again. Maybe it was an accident. In the decade of our friendship, I do not think he has ever actually called me. Should I just let it go or do I actually answer?
Jason has been my best friend practically my entire life. We met in First Grade, and up until this year, we have had most of our classes together. This past summer, right before our Senior year, his family moved a few towns over. Now, for the first time since I can remember, I started a school year without my best friend.
Fortunately, we are only about 30 minutes from each other, and even though he now goes to a rival school, we still hang out when we can. In fact, it normally wouldn't seem out of place at all for Jason to be messaging me at any time of day, but after last weekend, I never expected to hear from him again.
On Friday after school, I went over to his house and went with him to a party thrown by one of his friends from his new school. At some point in the evening, some girl confused me with another one of her girlfriends. Normally, not a problem, but once I told her that I wasn't the girl she was looking for, she exploded in laughter and made a huge deal about how much I looked like a girl.
My long hair and waifish looks made me the butt of all their jokes. It was probably just the alcohol flowing, but soon all the guys were pinching my ass and pretending to hit on me. The fact that I was from a rival school seemed to encourage the behavior even more. Jason didn't join in the mockery, but he couldn't exactly stand up for me either without being ridiculed himself. I turned to a bottle of Vodka and tried to numb the embarrassment.
The liquor didn't exactly help in that respect, but it did help to loosen my tongue. After the party, I stayed the night at Jason's house, not wanting to drive back home after drinking. We chatted a bit and he apologized for not having my back at the party. I told him not to worry about it, and that I understood why he couldn't, but I didn't think that I'd be going to anymore of his school parties. He agreed and we laughed, but then he said something that I now realize was a joke, but my drunk mind took it as something else.
He said, "Allen, you do have to admit though, you have a very pinchable ass."
For some reason I took that as a cue to confess to my best friend that I had been a closeted crossdresser for years. I told him that I liked to steal items from my older sister, and that I actually looked really good in her old cheerleader's uniform, leotard, pantyhose and all.
Unfortunately I had completely misread the room. When I was met with silence, I panicked and pulled up a picture of me in the aforementioned uniform on my phone and showed it to Jason.
"Why are you telling me this?" He asked, thoroughly confused.
"Um...honestly, I don't know," I said. "I guess it's the vodka and all the attention on my ass today."
Quickly, I tried to reverse course, but it was too late. The damage had been done. The awkwardness was unbearable. I woke up before Jason and snuck out, saying a quick bye to his mom as I rushed out the door.
All week I couldn't stop thinking about how stupid I was. What if he told our other friends? I couldn't believe what I had done. I had not heard from Jason since and never expected to hear from him again, but now he's calling me on the phone.
I finally slid the green icon to answer just before it went to voicemail and slowly brought the phone to my ear.
"Ummm...hello?" I practically whispered.
"Hey, uh...Al...it's...Jason."
This time my tongue was frozen. The lack of alcohol had rendered me speechless.
Jason continued, "Actually, it's probably better if I just talk...Oh man, how do I say this? I actually rehearsed it three times, but now I don't know how to start."
I knew what was coming and I was prepared to hear it. "Just say what you have to say, bro."
"Okay, here it goes. I don't know why you told me what you did last week, but I haven't been able to stop thinking about it."
"Yeah, me too," I interrupted.
"No, I mean I haven't been able to get that picture of you in that cheerleading uniform out of my head. You were...well you were right, you did look really good in it. I...I can't stop thinking about your legs."
I was completely floored. I was expecting him to tell me to never talk to him again.
Jason struggled to find the words, "I guess what I'm trying to say is, well, I wouldn't mind seeing it again."
"The picture, you mean?" I asked.
"No...well, yeah but," he stuttered. "What I mean is, I wouldn't mind seeing more of you like that."
"You want to see me in my sister's cheerleading uniform?" I asked, completely blown away at the turn of events.
Jason finally found the courage he was hoping to summon. "Yes, but I was wondering if you just dressed like that for fun around the house, or do you ever go out like that?"
I let out a small laugh. "No, I've never been out of the house in my sister's clothes. I can't even believe I told you, let alone showed you the evidence."
"Would you?" He asked.
"Like, would I wear it for you?" I questioned.
"No, would you go out in public as a girl?"
I had never really thought about it. I loved dressing up and I loved the way women's clothes and makeup made me feel. I had to admit, I could pull off a pretty convincing girl.
"I had never really considered it, but in the right circumstance, yes. At least I think I would."
Jason let out a sigh of relief. "Good, okay...um, well then can I ask you another question?"
Finally relaxing a bit, I said, "Sure...go ahead."
"Well, would you consider going to Sandberg's Homecoming with me as a girl? It's in two weeks, and I thought I had a date, but she bailed on me last minute."
I practically gasped, "You want me to be your homecoming date?"
He was hurt by my response, but in my defense, I couldn't believe what I was hearing.
"No, not like that. But, I'm embarrassed to go by myself and I don't want to not go to my Senior year homecoming. I just thought, you're my best friend, and I know we'd have a good time. You opened up to me and I didn't know how to respond, but if you'd let me, I'd like to see more."
I didn't know how to respond, but the prospect of getting to dress up in a sexy dress and show myself off had my mind flooding with ideas. I knew I wouldn't be able to say no.
"Please say something," Jason begged.
"I would be happy to." I finally said. "I have no idea where to begin or how we're going to pull this off without either of our parents finding out, but yes. I would like to try."
The rest of the conversation was a blur, but we decided that I'd tell my parents that I'd be taking a girl from his school to their homecoming and that I would be staying at Jason's house that night. I still didn't know where I would get ready for the evening, but Jason said he'd take care of it and that he would let me know. I just had to focus on getting an outfit put together.
Over the next two weeks, the initial excitement that I felt slowly morphed into nervous tension. What if the students from Sandberg recognized me? Maybe this was all just a prank to continue their earlier hazing of me. Jason did his best to calm my fears, but I was still hurt from that party and afraid of what might come at the dance.
It took a lot of convincing on his part, but I finally sent Jason a few pictures of me dressed as a girl, including the picture in the cheerleader's uniform that started all of this. In reality, him asking for a few pictures should have made me more nervous, but for some reason it really helped to put me at ease.
I took some money that I had been saving for some upgrades to my car and went dress shopping. I had bought small things here and there, like nylon stockings and jewelry in person, but I had never actually shopped for an outfit. I headed to a dress shop out of town, fortunately it was closer to Sandberg than it was my school, so it was not very likely that I would run into anyone I knew.
The woman working the store was very understanding and I was very upfront about my situation. My heart was pounding through my chest, and I felt like she could hear the terror in my voice, but I told the woman that I was transgender and that I was in need of a Homecoming dress. She practically squealed with glee and introduced herself as Claire.
Claire honestly seemed more excited about helping me find a dress than I was about getting to try on all the pretty clothes. She helped me relax and brought out a few items that she felt went best with my complexion.
At 18 years old and having never really been into sports, I really am quite diminutive and demure. I'm 5'6" and at only 130 pounds, I have a tiny waist, small shoulders, and as the students of Sanberg recently discovered, tend to carry a bit of plumpness in my buttocks and have womanly hips. My skin is tanned, not quite bronzed, but I do work outside in the summer, so I've held onto a bit of color. My hair is a wavy shoulder-length brown with natural blonde highlights, also a product of working in the sun.
Claire brought out three dresses for me to look at. The first was an emerald green spaghetti strap with a tight bodice that flared into an A-line that capped at knee length. The second was a strapless floor-length coral gown that had an iridescent shine to it. But it was the third that caught my attention.
The object of my desire was an off the shoulder, navy blue dress with inset sequins and a mid to low-thigh hem. The bodice was fairly form fitting but the skirt was wavy and puffed out from layers of tulle underneath the main fabric. It was so feminine and pretty that I reached out and touched the fabric with my hand.
"I take it you like this one?" Claire asked.
"I do!" I replied excitedly. "I like them all, but that blue one is simply gorgeous."
Claire nodded her approval. "Why don't you take all three to the fitting room and try them on? When you're ready, I'll help you with the fitting."
I couldn't wait. I bounded into the changing area with a hop in my step, ready to play dress up. Why hadn't I ever thought to do this before?
Of course, it would be a little awkward if I kept coming in to try on dresses but never purchased anything.
I tried on all the items Claire brought for me. The coral dress was pretty, but it was too formal for Homecoming and a little out of my price range. The emerald dress looked amazing with my skintone and I loved it until I slid the navy blue dress up my body. It felt and looked amazing. Claire even brought me some jewelry and a pair of 3-inch heeled, open-toe sandals to wear with it.
This was definitely the dress for me, but Claire noticed a slight frown on my face.
"What's wrong hun? It looks great on you." She asked.
"It does, and I absolutely love it...but I wish I filled it out in the chest a little bit more, if you know what I mean."
Claire smiled and gave a knowing nod. "I think I may have just the thing for you. Wait right here."
She disappeared to the back of the store while I admired my reflections in the mirrors. I could probably pull off A-cups with the addition of a bra, and I still loved how I looked, but a more feminine figure definitely wouldn't hurt.
Claire returned with what looked like a strapless bra.
"This should be your size." She said as she handed it to me. "It won't give you bountiful breasts, but it will help push up what you have and give you some cleavage."
Claire motioned to her own chest with cupped hands and smirked.
I slid the dress down and put on the strapless bra.
"It's really tight!" I exclaimed.
"It needs to be," she responded. "It needs to force everything into place."
That it did. I couldn't believe how this little thing squished all of me up into a fair amount of cleavage. I pulled the dress back on and marveled at the wonders of a pair of boobs.
"Wow!" was all I could manage.
"If you think that looks good, try a little bit of bronzer on the sternum and highlights on the top of your breasts. It will make them appear even bigger."
I just smiled at the mirror, happy as could be.
"Tell you what, if you buy that dress, I'll throw in the push-up bra for free."
"Claire, I think you have yourself a deal."
I bought the dress, a handbag, a silver necklace, and matching clip-on earrings. I didn't get the shoes because I wanted a closed-toe and all she had were sandals. A quick trip to the mall fixed that though, as I found a 4-inch heel, silver pump with an almond toe, and they had it in my size 9.
As I was leaving the mall, I glanced in Victoria's Secret and saw the most amazing lingerie set on display. It was a matching blue with shiny silver accent jewels and silver straps. It came with a bra, thong, garter belt, and nude, almost white looking glossy stockings with a navy lace top. The bra was even able to be worn strapless or as a halter. I was transfixed.
I went in to peek at the price tag.
"$149.99!" I gasped. That's as much as I paid for the rest of my wardrobe for the dance. I imagined what it would feel like to slide the silky smooth garments on and how they would look as I got ready for the dance. Unfortunately, I couldn't bring myself to spend that much money on something that wouldn't be seen anyway. It would have to remain just a fantasy.
I brought my items home and stashed them away in my closet, where my parents wouldn't bother looking. I was still unsure about where I would be getting ready for the dance, but I already had butterflies thinking about putting on all the finishing touches. Of course my mind kept drifting back to the lingerie I couldn't afford.
I texted Jason and described my outfit. He seemed excited and I almost sent him a picture, but decided that the first time he saw it should be in person. He told me that his parents were going out on the day of the dance and that I could use his house to get ready. I was to be there around 5 o'clock and park down the street so no one saw my car later in the evening.
It was the day before the dance and everything seemed ready to go. I had a nervous excitement about me and I couldn't wait to get home from school and get all of my things together. The only problem was that I couldn't get that lingerie set out of my head. I decided that after class, I'd drive back out to look at it, hoping it wouldn't be as grand as I was making it in my head.
The day dragged on forever, and when the bell finally rang, I sprinted to my car and sped back to the mall. I was huffing and puffing by the time I speed walked up to Victoria's Secret. There it was. Staring back at me. It felt like there was an angelic glow around the display.
I thought to myself, "Of course it would look better in person than I had been picturing it all week."
Just then, a saleswoman broke me out of my trance. "Can I help you with something?" She asked.
I felt like I was possessed. "Yes, I'd like to buy this set." I said robotically.
I was cursing myself as she bagged the items for me, but when it came time to pay, I dutifully handed her my credit card.
"Fuck, I need to make sure my mom doesn't see this bill." I thought to myself.
The saleswoman cashed me out and commented, "Thanks for shopping...whoever that is for is quite the lucky lady."
"You have no idea." I said with a grin.
I couldn't believe that I spent that much money on lingerie, but my heart felt full. I couldn't wait to put it on. Fortunately, I only had to wait a day.
After so much anticipation, the day had finally come. I spent the entire day trying to stop myself from clock watching. I still couldn't believe that I was actually going on a date with my best friend, let alone going to a school dance as a girl. I packed all of my things in an overnight bag, and said goodbye to my parents as I headed over to Jason's house. Thankfully, they were none the wiser to my real intentions.
I arrived and parked down the street as Jason requested. Like he said, his parents were already gone for the evening. He let me in and after a minute or so of awkwardness, he told me I could use his parent's bedroom to get ready.
I dropped my bag on the bed and just sat down for a minute. I felt like I had to catch my breath. Was I really doing this? Jason was down in his room getting ready, and I was about to transform myself into a woman for him in his parent's own room? What was I thinking? I was starting to hyperventilate.
I tried to calm myself and set upon my task of getting ready, but nothing could stop my heart from thundering inside my chest. Finally, I looked at my bag with a frown and realized that inside waited an immaculate dress and matching lingerie. My breathing finally slowed and I was able to focus on what I needed to do.
Having already shaved, waxed, and washed my whole body, I jumped right into finally putting on my outfit for the evening, starting with my lingerie. I slid the sheer nylon stockings up my smooth legs, releasing the lace top at the highest point of my thighs with a snap. I pulled up the thong and tucked my meager penis away, making sure to present a smooth front. I then fastened the garter belt on my waist, above my hips. The straps and accents cascaded down my abdomen, coming to a rest just above the top of my panties. Lastly, I leaned over and clasped the silver garters to the blue lace of the stockings.
Fortunately, the Victoria's Secret bra was a bit bigger than the push-up I got from the dress store. I layered the blue lace bra on top of the nude pushup and admired the sudden appearance of full B-cup breasts and a fair amount of cleavage. I took Claire's advice and added the makeup to make the cleavage more pronounced. She definitely knew what she was talking about. I couldn't believe how round and full my chest appeared.
I finally slid into the dress, pulled it up onto my shoulders, and struggled to contort myself in a way that would allow me to get at the rear zipper. The bodice dripped like a liquid off my chest and then flowed outwardly at the waist, ending in the sparkly tulle a few inches above my knees. I posed in the mirror and admired my new breasts and ample rear, still showing despite the puffed skirt.
Now it was time to transform my face. I set up in the bathroom and went to work on my makeup. I applied foundation, concealer, contouring, highlights, and a pink lipstick that made my lips plump up. I pulled out all the stops and used all the tips and tricks I had learned from watching countless makeup tutorials. I applied feathery false lashes and gave myself a smokey eye shadow that started dark near the eye and then transitioned to blue and silver in the corners.
I styled my hair with a lazy wavy curl. It rested nicely just above my shoulders and cut my face in a way that seemed to thin it out. Finally, I put on my dangling, silver earrings, matching necklace, a bracelet, and metallic blue press-on nails. I then slid my feet into my 4-inch pumps and gave myself a twirl to admire in the mirror.
The woman looking back at me was drop-dead gorgeous. I knew I was good, but the sight before me was a work of art. I was so happy, I could hardly contain myself. I finished off with a few sprays of perfume on my neck and breasts, grabbed my clutch, and then headed out of the room to find Jason.
The upstairs was dead quiet, so I quietly crept downstairs to find him. My heart was pounding, and I found myself gripping the railing extra tight as I discovered a weakness in my knees from the anticipation of Jason seeing me for the first time. The door to his room was open and I caught a glimpse of him with his back to me, affixing his tie. I stood in the doorway and waited for him to turn and finally see his date for the evening.
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