[ WP ] After trying on a ballgown a tomboy finds she is starting to want to dress and act like a 1950s woman

Growing up, I'd always been led to believe that just because I did n't have a penis, I was inferior. With three older brothers and an absent mother, I did everything I could to be one of the guys. I wore baggy clothes, I rolled around in the dirt, I spat on the ground and swore that I'd never be caught dead being a girly girl. 
 
 That mindset cost me a lot of friends. I left a sleepover at eight years old because the other girl wanted to play with makeup. I was n't going to be caught dead with my face like a clown. The last thing I saw as I left was this little redheaded girl bawling because of me. I never saw her outside of school again. 
 
 Things started to change when Samantha moved in to the cul-de-sac. Here was a girl a year older than me, who seemed to think exactly like I did. She wore her brown hair trimmed as close to a boy's cut as she could. I only ever saw her in jeans and sneakers for the first two years. When she saw that I was a girl acting macho like her, she immediately took me as her best friend. 
 
 Every weekend, Samantha would go to spend time on her father's farm, and one week, she invited me. We got into a lot of trouble out there. Samantha showed me the joys that I'd been missing living in the suburbs. We crawled through what felt like miles of bramble bushes. We stole Farmer McPhearson's blueberries, We caught fireflies in jars. And then, under the starlight on Overwatch Hill, we traded secrets. 
 
 Samantha was a tomboy because her mother was a former beauty pageant star. That's when I first learned the term `` Living vicariously.'' Samantha's mom wanted to recapture that glory by making her daughter the most beautiful person to stroll down a catwalk. But Samantha hated that. After one pageant, she had gotten her heels caught on her dress and had tumbled off the stage. While the other parents had tried to see if she was hurt, Samantha's mom only yelled at her for costing her a trophy. And that's when Samantha decided to give up being a girl. 
 
 I remember leaning back and taking her hand in mine. She surprised me by leaning over and stealing a kiss. I could n't tell what was brighter, the blush on my face or the jar of fireflies between us. But I also could n't deny that I liked it. 
 
 Those weekends with Samantha became the high point of my week. We'd stroll around that small town called Appleton, sharing drinks from the soda fountain and secret kisses where the eyes of the conservative farmers could n't see. Then, two and a half weeks after my thirteenth birthday, things changed. 
 
 Every so often, Appleton held a raffle. Usually it was for dinner at a nice restaurant, which involved riding the bus twenty miles to the east to Middleburg. Sometimes the prize was a new bicycle. Sam won that one, and came away with a real beauty that allowed her to zoom down the goat trails in the woods. 
 
 On that day, however, the prize was a `` Queen for a day'' package. This would involve a trip to Middleburg, two hours in a salon, and being fitted for a nice dress, and an all expenses paid meal at a four-star restaurant. By this point, me throwing my name into the raffle was a force of habit. The last thing I wanted was to be drowned in femininity. 
 
 Would n't you know it? I won. I tried to pawn it off on someone else, to claim any of the smaller prizes instead, but the rules were the rules. I had to take the trip up. Everything had already been booked for me. 
 
 Samantha went along with me because there was no way she was going to let her girlfriend face such an evil alone. 
 
 For those two hours in that salon, I was waxed, primed, and painted. By the time I could finally look in the mirror, I could n't recognize myself. They had even covered up the scars of the bramble bushes on my cheeks. I looked more like a magazine model than a young man. I looked over to Samantha, and she was blushing fiercely. Apparently, I was so beautiful that she had to bite her lip from saying something stupid. 
 
 My day was n't done there. From the salon I was ushered into the boutique, where they took all my measurements. It was the first time I had ever worn a bra. I had either bound them, or let them hang free whenever Samantha was around. But now, they were lifted and separated, making me look more like a college age woman than a junior high girl. After the bra came the matching underwear and I quickly felt that I had been missing something by wearing boy's underwear this whole time. It was silky and smooth and a whole new sensation. 
 
 As they started fitting the bodice of the dress over my chest and adjusting the layers of petticoats around my waist, Samantha seemed to vanish. I looked around for her as I was taught how to wear stockings. I could n't find her while they got me into the three inch heels and taught me how to walk. Just when I thought I had lost my girlfriend forever, she re-emerged, wearing a handsome tuxedo. Damn, she was amazing. 
 
 The two of us went to dinner at Patrice's, Middleburg's only four star restaurant, and we were treated to the finest food either of us had ever eaten. Most of it we could n't pronounce, and that just made us laugh through the night. 
 
 After dinner, we went to a dance hall, where we shared in three lovely slow dances and finally, we were done with the royal treatment. 
 
 I did n't want my brothers to know that I had actually enjoyed being primped and pampered. So, when we got back to Samantha's farm, I stored the dress in a wardrobe in the attic. Samantha noticed that as soon as I was back in jeans, I was still wearing the bra underneath. 
 
 `` You looked amazing, babe. Probably the hottest I've ever seen you.'' Samantha looked down. `` If you, you know, want to dress up all pretty the next time you're here, I would n't mind it as much.'' 
 
 I gave her a kiss on the forehead, leaving a perfect red lipstick imprint there. And we did just that. I bought clothes for myself to wear in her company. But for whatever reason, I never picked up anything modern. The first skirt I wore fell to just above my ankles. The makeup and nail care kit I had gotten from the salon was used to make me look mature. 
 
 Each week, more and more of my allowance went to creating this new persona. I had spent so much time trying to be `` Jimmy'' that I had almost forgotten my name was Jasmine. But now, Jasmine was coming back. When I got my first job, I spent that paycheck on an old style fifties dress. It was ivory, with a fake pearl brooch and I wore it to Samantha's farm to surprise her. 
 
 The look on her face when she saw me as this fifties housewife was priceless. I posed with a plate of pancakes as she took my picture on an old disposable camera and then we shared breakfast together. 
 
 When we were nineteen and eighteen, Samantha and I moved into a one bedroom apartment in Middleburg. 
 
 I bet you want to hear about the first time we had sex. But a proper lady never tells.
