I am incorporating suggestions made by Angela Rasch. She helped me edit this so I am thanking her and using her suggestions to make this better. I think it is even better thanks to her. The first chapter is all her suggestions so I am giving credit where credit is due. I will use her suggestions for the next story I write as it does help to make it better. Also I cut the getting ready for the prom chapter and turned it into a paragraph inserted before Leon arrives. I was not happy with the chapter and felt it slowed down the action of the story. I hope you like this better. Also I incorporated this into a single story.

Chapter 1: Leon needs a new date

“You have got to find me another girl for Prom. Michelle dumped me . . . Can you believe it!”

Someone was playing “Happy” by Pharrell on their Beats, which seemed totally random given the maxi-frown that was Leon’s face.

In a way his obvious pain was at least partially my fault, because I had set him up with her. “She’s just impressed by Todd because he’s the captain of the football team.” I thought she was better than that!

“I’m captain of the swim team,” he wailed. “Doesn’t that count for anything?” He hadn’t touched the onion rings he’d ordered, and then smothered in catsup, even though they smelled terrific.

A cool, spring breeze blew around my bare legs every time someone opened the door into the Burger Shack. Spring makes deciding what to wear an adventure. I thought. Maybe it’s a little too early for shorts, but I like the way my legs look since I decided to shave them. I’ve told everyone I do it to support Leon, who has to shave his body for swimming.

“I don’t get it,” I commiserated, feeling his agony. “You’re better looking than Todd.”

Leon is the handsomest boy in school. He’s tall, at least a half a foot taller than me, and his dark wavy hair and emerald green eyes are impeccably lovely. What the heck is Michelle thinking! I picked her because I thought Leon would like her. I never dreamed any girl wouldn’t love the chance to be with him.

Leon blushed. “We’ve been best friends since the first grade,” Leon stated. “Be honest. Am I a dork loser, or what?”

“A loser?! If you’re a dork what am I? You seem to forget, I don’t have a date for Prom either.”

He looked at me for a moment. “Sorry. I forgot for a moment while wallowing in self-pity.” His face broke into that burst of sunshine that made me quiver inside. “Girls are crazy, Les. You’re one gorgeous guy with your long, dark-black hair. You could be a rock star.”

Gorgeous! I involuntarily reached for my hair and happily fingered its natural curl. “I’m too short,” I protested, hoping the burn I felt on my face wasn’t a huge blush that he would see and know what I was thinking.

Sometimes it seems my chocolate brown eyes are a little too warm and my hips too wide for a guy. I do like having my hair down to my shoulders, even though I have to brush it quite often to keep it neat. Mom has helped me with it giving me tips on conditioners and a proper trim from her beautician to keep it neat. Three weeks ago we had a “special” night together and she put my hair up in rollers.

I focused on Leon. “Okay, I’ll see what I can do. As long as I’m looking for the perfect date for you, do you have certain requests?”

Leon grinned mischievously. “Oh, someone about your height, with beautiful black hair and brown eyes. Maybe the female equivalent of you.”

I know he’s teasing, but. . ..

It won’t be easy finding another date for him with less than a week to go before prom.

Maybe it’s fate? The breast forms I’d ordered online arrived the day before. I hadn’t even been able to try them on, yet.

I know I can do it. With Beth’s help I’ve been passing as a girl. She had been assisting me for nearly six months. My “wardrobe” consisted mainly of things my older sister had left behind when she went away to college. She knew all about me and had okayed me using everything but her lingerie and cosmetics.

My mind raced. “Do you trust me?”

Leon smiled. “Of course. You’ve always had my back.”

“I know the perfect date, but it has to be a surprise. On the night of the Prom come to my house with a white corsage; and she’ll be waiting for you.”

“That’s just like you. The Mysterious Leslie! You should forget about college next year and go right to Vegas with a magic act.”

“I’m going to pull your date out of a hat,” I vowed. “You’re going to love her.” I hope.

* * *

Even though I’d had the overwhelming need to dress as a woman for years, it had been less than nine months since I’d told my parents. They had been shocked at first, but with their help, and the weekly advice from a professional family counselor I’d been able to put my guilt behind me.

Beth was the only one outside of my immediate family who knew. It had been an accident that she saw the cosmetics on my dresser. I hadn’t expected her to follow me into my bedroom when she was studying with me one evening. When she confronted me, it was only to confirm suspicions she’d had for some time.

For the last month we had become more daring and had gone shopping several times as girlfriends. I’d used birdseed in plastic baggies to form breasts under my tops. After I realized no one saw me as anything but a girl when we were out, I relaxed and had a great time.

Beth and I had been dating for about a year when she made her discovery. We continued to “date” for a while, but I had become less and less interested in kissing her. We mutually decided our relationship had evolved into something platonic, with her doing girl things with me. Last month she gave me a bottle of Pink Sugar perfume as a friendship gift. I wear it anytime I’m not in school.

She’d eventually started to date Alec, a boy I thought was right for her. I had become attracted to Leon and wasn’t sure how I felt about it. Beth and I had spent hours talking about it and wondering what I should do.

I left Leon at the Burger Shop and put my plan into motion.

“Beth!” I squealed into my phone when I had gotten a block away from Leon. “You’ll never guess what just happened. Michelle got asked to Prom by Todd, so she dumped Leon.”

“Michelle’s an idiot,” Beth stated flatly. “In a way I’m relieved. Alec had suggested that we share a limo with Leon and Michelle; and I can’t stand that empty-headed bee-yatch.”

“Guess who Leon wants to take to Prom?” I asked.

Silence prevailed for a few moments. “I can’t think of anyone he’d like, who doesn’t already have a date.”

“What about me?” I whispered.

“Leon asked you to Prom!” she screamed. “That’s awesome!”

“Not exactly, but ya. Yes he did, in a way.” I went on to relate our conversation . . . word-for-word.

“You have to go,” she said with the authority she had earned in our friendship to make certain decisions for me.

“Do I dare?”

“What’s there to even think about?”

“What will everyone think?”

“They’ll think Leon got really, really lucky.” Beth giggled. “I know where the perfect gown is for you. . .and shoes to match. That blue-green dress in Olivia’s has your name on it, Leslie.”

It does!

“I’m serious,” I said. “I don’t care what anyone thinks of me. I’m going to college a thousand miles from here. But, Leon’s going to State U. and will be living with his parents to save money. He’ll never live it down.”

“Does your phone have a calendar on it?” She asked sarcastically.

“It does, but. . ..”

“Check the calendar and see what years it is. Pull your head out of your past. Same sex marriages are legal. Clay Aiken is running for Congress, for gosh sakes. People will take one look at you, once I have my salon give you the works, and will know you were meant to be what you are. . .a stunning girl.”

“Maybe. . ..”

“No ‘maybe’ about it. You put on a nice outfit, brush you hair into a bouncy ponytail, and meet me at Olivia’s Dress Boutique in one hour. We don’t have anytime to waste, girl. YOU’RE GOING TO PROM. Not too much make-up,” she warned. “You’ll be trying on a lot of dresses.”

As soon as I got home I ran upstairs to my room. I got out my breast forms and glue and went into my bathroom. I checked to make sure that I was smooth all over. I noticed I had a little fuzz, so I decided to use depilatory cream to get rid of it. My body felt delightfully smooth. I can’t understand why guys like to keep their body hair. Oh well, to each his own.

I ripped open the box containing my breast forms, which match my skin-tone perfectly, and read the instruction. Lying on my back on my bed, I carefully lined up the breast forms on my chest and applied the glue. It’s better to glue them on just in case we decide to try on a strapless gown. Besides, I liked the feeling of having breasts. I wish I could have my own.

Waiting for the glue to set I looked round at my bedroom. Dad had painted it a lovely pink for me a month ago and Mom had helped me decorate it to feel more comfortable.

Despite the training I’d received from my counselor I allowed a few negative thought. I’m my father's only son, and I am sure I’m a major disappointment to him because I’m not a very masculine. I’m not into sports and Dad was a total jock when he was in school. Leon is more of my dad's idea of a son. They both are center-midfielders in soccer.

Leon! A smile formed on my lips. If things go right, maybe he’ll kiss me.

What my dad really likes about me is that I’m not a wimp. He told me yesterday that when I set my mind on a course of action I’m a real bulldog. He’ll understand that this is one of those times. The other night when Mom and I were doing each others' nails, he called me his little “princess” and kissed me on the cheek.

After the glue set, I slipped on a white lacy bra and matching thong panties. I’m so tiny down there, I don't have to really tuck it because it barely makes a bulge. I selected a mint-green t-shirt with a white Persian kitty on it and a dark-green skirt. It’s a special day so I’ll wear heels. I quickly applied a light coating of make-up.
I rushed out of the door, locking it behind me, and ran for the bus stop. Or rather, I floated along the street. I’m going to Prom with Leon!

Olivia owned a reasonably priced dress shop, and designed her own dresses. Beth and I loved the quality of her work and her realistic prices. She had some ready-made and she would also design a gown for you. Since I did not have the luxury of unlimited time, I had to settle for a dress off the rack. While I waited for Beth, I looked through the shop's windows and saw a few that I liked.

I knew which one Beth favored and couldn’t argue with her choice. It was a beautiful, midnight-blue-green, silk, floor-length gown that I also really loved and hoped was in my size.

We went in and it became fate when we found that dress was in my size.

“I loved the way the color picks up the blue highlights in your hair,” Beth gushed.

“The silk feels luxurious.” I stated. “All the lotions I use have paid off leaving my skin creamy smooth. It feels like someone is caressing my waist.”

“You’re lucky you dropped those six pounds,” Beth said. “That dress accents your slim waist.”

It flowed gracefully while I spun in front of the mirror.

Beth found four-inch heels that matched. “You’ll need to practice dancing a bit more before Prom.”

I smiled. Although Beth was Alec’s girlfriend now, we still loved to dance together and spent many evenings in each others' arms.

To be sure, and for the fun of it, I tried on about fifteen other dresses, including an amazing wedding gown that Olivia said was pretty enough for a beauty like me.

“If you’d like,” Olivia said. “You could earn some money working as a model for me.”

Wow!

I put on “my” dress again, and then Olivia suggested a few small alterations. She pinned the gown and promised to have it done by the next afternoon.

I gave her my parents’ credit card and began to plan an argument for the over $400 expenditure. It’s my birthday next month. I’ll tell them it’s an early present. I’m sure when they see me in it, they’ll understand.

Beth and I decided to go to Secret Desires for the lingerie. New lingerie is the base for a special outfit.

“You should get a lacy black style to compliment the dress’ colors,” Beth said. “If you get them in navy it would be too much blue.”

Having shopped Secret Desires nearly every Saturday for the last month, we quickly found what was needed.

Another early birthday present.

“Let’s go to the jewelry store where I got my ears pierced. I need those gold chandelier earrings.”

Beth laughed. “You’d better tell your parents all of this counts as a graduation gift. As long as we’re there you should get a gold chain to set off the blue of the dress.”

We stopped in the food court for a bottle of water and to catch our breath.

“Your new shape looks really natural,” Beth said, referring to my breast forms, which I’d totally forgotten, as if I’d been born with them.

“Now all I have to do is find the patience to wait until my salon appointment next Friday afternoon and the Prom that night.”

I’m going to my Prom with Leon. I can’t believe it.

Chapter 2: At School The Next Day

I got up the next morning and got ready for school. I put on a pink thong, it was a girl's thong but on the plainer side. I knew I could get away with it today, as this quarter I had Health and no gym, thank goodness. I wore boy clothes, but in a unisex style (mostly jeans and polo or t-shirts). I finished dressing and worked on combing my shoulder-length hair into a pony tail. I really wanted to put the band on it higher, but knew it would cause teasing.

I put my white Keds sneakers on, which I loved to wear as the male and female styles were the same. So I could at least be all girl in my imagination. I was a lovely girl who was in love with her best male friend Leon. I was looking forward to Friday night's dance as it may be the one and only time that I could realize my fantasy. I knew it would be well worth it if I only got that one chance.

I went downstairs, and had my breakfast. I was lucky today as both my parents were there. My father is a tall, muscular man. He was on the football teams all through High School and College. I know I was a disappointment to him. I was slender and not too tall. I had no interest in playing sports. My father got on well with Leon as Leon reminded my father of himself when he was younger.

My mother was a beautiful woman who was petite in build. I resembled her both in looks and stature, except I was a little bit taller than her. I think she really would have liked her only child to be a girl and encouraged my feminine behavior whenever she could.

We ate breakfast in silence, each of us dealing with our personal thoughts. Mine were on how was I going to pull it off. I had to figure out where Leon could pick me up. If I had him pick me up here, I would have to deal with my parents finding out about me. Also it would give away the surprise of Leon finding out who is date is. I could meet up at my friend, Beth's house and I was thinking of this. I also could ask her if she could help me with my hair and make-up and cancel the salon all together. It would make it easier to slip out with no one noticing. Besides if I went to the salon I would have to leave school earlier and would probably have to let my mom know. I would ask Beth at school today if she would do that for me. She was great at doing her own hair and make-up.

After finishing breakfast, I left the house and began my short walk to school. I had to pass Leon's house on my walk and today it happened that he was just leaving for school as I passed his house. He asked if he could join me and of course I said yes. He proceeded to grab my books from me, before I could stop him. I wondered to myself what was behind that. He always seemed to do little things for me that a guy would do for a girl he was trying to impress. It got me curious as to what was going on in his mind. But I shrugged it off thinking it was not important and probably did not mean what I thought it did.

We walked on in silence for a little bit, each of us wondering about Friday night. Finally Leon could not bear it any longer and started to ask questions about his date.

“Do you know what flowers she like? I want to get her a corsage in her favorite flowers. I think that would be so romantic, don't you?”

“She loves white roses.”

“Oh, what a coincidence, so do you Les.”
I suddenly realized that I had to be very careful of what I said, because I could give the whole game away before Friday night.

“Yes it is, but I am sure that a lot of people like white roses.”

We arrived at school, and had to go our separate ways as we were in different homerooms. I had to think up ways to answer further questions without giving my game away. I knew I would tell him that he would find out her name when he met her. I used a variation of my name as my girl name as it is unisex. When in girl mode I went by Lesley. I liked that spelling better. But if I told Leon that name I knew he was more than smart enough to put two and two together. I would let him know what dress I would be wearing if he wanted to coordinate his tuxedo's cummerbund color to match. I knew he probably would as he was romantic in that way. I really could not understand how he could not get dates. He was such a sweet romantic guy.

My morning went by like any normal school day. I focused my thoughts on the classes and put my thoughts about Leon and the Prom in the back of my mind. I knew come Friday night my relationship with Leon could very much change if not be over. I was willing to take that risk, because on the other hand I could very well become his girl. I had a smile on my face when that thought occurred, that would make my dreams come true. And like any other girl, I dreamed of being his wife and taking care of his needs.

“Les, what is 1,043 times 1.043?”

I was suddenly jolted out of my revery by the teacher's question.

“I am sorry Ms. Johnson, I don't know.”

“Well maybe next time you will keep your mind on the lesson?”

The rest of the class laughed as she resumed the lessons and I made up my mind to pay attention.

I met up with Leon at lunch and answered his questions. Beth was okay with my new plans, so I told him to pick me up at her house. I told him that his date was shy and tell him her name when he met her. He wanted to know what color dress she would be wearing as he wanted to match so I told him Midnight Blue.

The rest of the day went by in a blur. I was so distracted about thinking of the Prom. I could hardly wait for the next few days go by.

Chapter 3: The Prom

Finally the day of the Prom arrived and I went over to Beth's house where she proceeded to get me ready for my big date this evening. We spent several hours getting my make-up and hair just right. I had no worries about the dress. After a few hours I was ready and waiting for Leon to arrive.

The doorbell rang, chiming throughout Beth's house. She flew down the stairs to answer it before her parents could get to it, telling me to wait a minute or two to make my grand entrance down the stairs. As the moment was finally arriving and the fruition of my plans for my Prince Charming and my turn as Cinderella, my fears were kicking in and the butterflies in my stomach were in full flight.

I gathered my dress in my hands as I prepared to glide gracefully down the stairs and into the downstairs hall. Leon looked up at me as a smile played across his face. He looked up adoringly at me. He looked so sexy in his dark blue tuxedo. It so complimented my gown. I could hardly wait to be embraced in his strong arms. In my head violins were playing a romantic tune, I had a feeling just looking at him that things were going to work out, I only prayed that others would be accepting of me, as I thought that after tonight I could never go back to being a boy, especially after seeing the look of ownership in Leon's eyes.

“Hi Leslie, you look as beautiful as I knew you would. I am so glad that you are finally making an appearance.”

“Actually it is Lesley with an ley at the end, Leon. And what do you mean?”

“I always knew you were a girl, Lesley, I just could not think of a way to get you to show your real self, so I figured if I could not get a date for the prom you would dress up for me and you did. I have always been attracted to your feminine nature and now I see that you make a beautiful girl. I would love to date you now, if you are willing?'

“Leon, let's see what happens at the Prom and take it from there. I am just glad that you are not disappointed, but why didn't you tell me earlier, I have had a crush on you for a while but thought that you were not interested in me.”

“Well hon, I tried to show you in all the little ways that guys show their interest. I carried your books for you, opened car doors for you when I gave you a ride. Here is your bouquet of white roses and blue tipped orchids for the Prom. Hope you like them.”

As he said this he handed me a beautiful bouquet of my favorite flowers plus some that complimented my dress. I was in Heaven. He was so romantic and was really sweeping me off my feet. Beth grabbed her camera and took several photos of us, then we said our goodbyes.

Leon escorted me down the path, with the smell of roses in the evening air. He guided me to his car and opened the door for me. I swept my dress under me as I swiveled my legs into the car as Leon got into the driver's seat.

He drove to the High School and parked his car in a secluded part of the parking lot. He leaned over and gave me a passionate kiss on my lips. I could feel his tongue probing for a way to get into my mouth, I opened my lips and let him penetrate my mouth. The kiss was so divine. After we separated, I checked how my lipstick looked and touched it up. I reached up to his lips with a handkerchief and wiped off the lipstick that was smeared on his sexy lips.

We got out of the car and walked into the school and headed for the gymnasium. We got to the desk where Leon told the chaperones our names. They shot me a glance and a look of shock appeared on their faces as they realized who I was, but that passed real quick.

“You look beautiful, my dear, I am so glad that you are done being a tomboy.” My English teacher, who was acting as one of the chaperones said.

“I am looking forward to you in class Monday.” The other chaperone, my Chemistry teacher replied.

Leon escorted me into the gymnasium. The Prom committee really transformed the place. They were potted plants all over the room. Streamers of red, white and blue were draped all over the place. There was a Wurlitzer jukebox in the middle of the room playing music. It was playing “In the Mood” by Glenn Miller. I knew this cause I love the music from the Thirties and Forties and was a big fan of Glenn Miller and the Andrews Sisters. It was one of my secrets, but I found that music to be very romantic and glad that the theme of this year's Prom was the Forties. The gown I found fit into that theme very well, but yet had a modern touch to it.

Leon swept me onto the dance floor and led me into the Jitterbug. I never realize he knew how to dance, but he was great. I loved being in his arms as he guided me all over the dance floor. We stopped to a round of applause.

“I never knew you could dance like that.”

“I love that music and my mother forced me to take Ballroom Dancing saying that a gentleman should know those dances so that he can romance a lady better.” he chuckled.

We danced and talked all evening together. I was rapidly being swept off of my feet by him. He was everything I dreamed of and more. I could see that he was feeling the same way about me. He could not take his eyes off of me. We flirted with each other all night.

Leon walked over to the jukebox, to pick out a song for our last dance. He pulled me into his arms as the Andrews Sisters started to sing “I Don't Know Why.” He learned closer to my ear and whispered, “Please be my girl. I am so in love with you.”

I whispered back, “Yes, darling, for the rest of my life.”