Prom Queen

"Play your cards right and who knows?" Colette teased, certain that would never happen.

She carefully cut and shaped a couple more pieces of the squishy material making these two larger and rounder than the hip pads then stuffed his bra.

"Hmmm," she mused. She pulled one up a bit then pushed the other one to the side, then said, "Oh, yeah. Just like that. Perfect!"

Dillon turned sideways and said, "Holy shit! I've got boobs."

He hollered for Damon who came to the door.

"Don't laugh or I'll kick your ass," he said. "Just take a pic."

"You look ridiculous, man," he said as he took two more quick snaps.

She picked up the dress then said, "Okay, step into it like this." She showed him how then handed it to him.

The fit wasn't perfect, but it was very close and more than good enough.

"Okay, very nice," Colette said once she zipped him up.

She took another close look, shook her head and told him, "And I hate you even more for being able to wear a dress in my same size, too. And worst of all, you look better in it than I do!"

Dillon was surprised at how nice it felt as the material moved against his body or the way the pantyhose felt on his legs. He was even more surprised when he felt himself getting physically turned on, something he'd never expected. The padded garment hid any kind of bulge that could show through, but the feelings quickly passed as Colette told him to sit down so they could start on his makeup.

She put a towel around his neck and upper body so that nothing would get on the dress then explained what she'd be doing starting with a liquid foundation she began applying with a makeup sponge. That's when she realized her brother's eyebrows would have to be tweezed before she could go any further.

It only took about five minutes, and it stung each time she plucked a hair until the brow was thinner and shaped in a more feminine way. Waxing would have been better but this was more than adequate for a Halloween costume.

Dillon didn't pay much attention as Colette applied his makeup. She was talking the entire time, explaining what she was doing and why, but Dillon couldn't stop marveling at the change that was taking place in the mirror directly in front of him.

The foundation made him look pale, but once Colette started applying other kinds of makeup he understood why it was necessary as it made his face look soft and smooth while serving as a basis for everything else.

The first thing she did was fill in his eyebrows using a dark-brown pencil and just that alone made an incredible difference in his appearance.

"Oh, my God! You are gonna be such a cute girl!" his sister said as she looked at her handiwork.

"Next...we're going to apply eye shadow like this...and then blend it like that..."

By the time Colette added eyeliner and mascara, Dillon's eyes had so completely changed his face he no longer recognized himself.

"Jesus! I really do look like a fucking girl," he said turning left then right admiring the way the makeup made his eyes pop.

"Dude. Get a shot of this," he told Damon.

Damon didn't say anything, but his body was telling him what he could never say out loud. His best friend now looked enough like a female—and a very cute female at that—that his brain was sending signals south to his Johnson.

"Damn, you really do look like chick, man," he said as he took some more photos.

"Told you!" Colette said proudly.

"Okay. Now...let's put a little bit of blusher on those apples under your gorgeous cheekbones..."

She brushed and swirled and Dillon noticed he was once again getting hard just looking at himself.

"Excellent!" Colette pronounced.

"We're gonna hold off on the lipstick and nails until we get your hair done, okay?" She wasn't as much asking as she was informing her younger brother.

She plugged in her blowdryer and curling iron and grabbed a brush. "First, we're gonna give you a side part..." She made a line down the right side of his head then divided the hair left and right. "I'm gonna have to trim one side a little though, okay?" she told him.

Dillon not only didn't care, he was so into this he couldn't wait to see the final result. "Yeah, sure. Do whatever you gotta do," he told her, now fully mesmerized by the transition.

"That's the spirit," she said as she began drying it right after trimming the long side. In just a couple of minutes, his hair was not only dry, it looked...different.

By giving the ends of his hair a trim and a well-defined side part, his hair now looked as feminine as his face. It was soft, shiny, and silky and he was nearly fully erect although Mr. Happy was pointed straight down; something that would become very painful unless he could reach down and straighten him up. But the thought of letting either his sister or his best friend know he was this aroused wasn't going to happen, so his rock-hard cock was just going to have to wait until he had some privacy.

She then used the curling iron to turn the last few inches of his hair underneath giving his hair a soft, gentle wave at the bottom. When she finished, the image staring back at him was so incredibly sexy he involuntarily groaned.

"Fuck me!" he said again quietly turning his head to both sides as Damon snapped some more pics.

The photographer was also suffering from a similar dilemma and made sure to stay bent over as he took his pics to avoid showing off the huge bulge in his jeans.

"Well, look at you!" Colette said thrilled with the near-final product.

"Now we'll take care of those big, puffy lips of yours then paint your nails."

Dillon chewed his nails and they were a mess, but Colette had some kind of press-on things in a plastic package, and after gluing them to his own nails, he had instant female-looking fingernails that were already painted a dark red color which matched the glossy lipstick his sister was painting on his lips using some kind of wand thing.

"Oh, yeah! That's what I'm talkin' about!" she said.

She pulled the towel off and said, "Voile! You look amazing!"

And he did. Dillon literally could not believe he was the person looking back at him in the mirror. The image he'd had of himself, the one he'd seen all of his life and that was so deeply burned into his brain, was gone. In its place was this very pretty, very young girl looking back at him, and it was blowing his mind.

"Now, let me see," Colette said. "Oh, here we go. I knew I had a pair of clip-ons."

She held the gold earrings up to his ears and said, "You're going to look stunning!"

She clipped on the long, dangling earrings before removing one of her own gold necklaces with a gold pendant from her jewelry box and hung it around her brother's neck.

"I now pronounce you...a girl!" she said. "No, wait! Not yet!"

She grabbed her perfume and said, "Hold out your wrists together for me."

She dabbed some on them then told Dillon, "Rub them together then do like this on your neck. Gently, okay?"

The smell was intoxicating and the look was mesmerizing. Dillon couldn't take his eyes off the mirror.

"Jesus, fuck!" he said still staring.

"Hold on. We're still not done. Stand up, okay? Then go sit down on the bed. You still need some shoes."

There were several pairs of black heels at the foot of her bed Dillon hadn't noticed before.

"I borrowed from some of my friends hoping one of these will work. Nothing too high because having never walked in them, you'd be crippled after a couple of hours. But I think these will be perfect," she said picking up a pair with an ankle strap.

"Sit down right here," she said tapping the bed. "But smooth your dress first, okay?"

Dillon had seen girls do that all his life and as he did it for the first time, he couldn't believe how natural it felt. He sat down and held out his right foot as Colette tried on the shoe.

"I knew it!" she said. "A woman's 9 is perfect for you. Not bad, dude," she teased. "If you had feet like Damon, this couldn't happen."

Damon wore a man's 12 and Colette wouldn't have been able to find anything that big without special ordering it and that meant spending money she didn't have.

"These heels are 2 1/2 inches so they're not all that high, but you're going to feel like you're on stilts. They're not too spiky, either, which is good because you'll have more surface area on the heel for walking. Spikes are a bitch. Trust me on that."

She strapped both of them on then offered her brother a hand. He stood up, wobbled, caught himself, then stood still.

"Oh...my...God!" Colette said before calling out to their mother.

"Mom! Come check out your new daughter!"

Colette helped Dillon take his first-ever steps in heels, stopping when their mother walked in.

"Oh, my heavenly days!" she said putting her hands over her face. "Dillon? Is that really you?"

"Um, yeah," he said in his masculine voice.

"Oh, my... You look...unbelievable!"

She turned to Colette and said, "You did such an amazing job! I can't believe that's your brother."

She turned back toward her son then said, "Damon, please, please, please get some pictures! Oh, my goodness! You are so pretty, honey!" she said before realizing to whom she was talking.

Dillon couldn't help but smile, and when he did both his mom and Colette said, "Look at that smile!" They turned him around and told him to smile in the mirror and when Dillon saw his image, he felt some kind of fluttering in his stomach but the word 'tummy' came to him almost naturally.

"Dang, dude!" Damon said still snapping pics.

"He's hot, isn't he?" Colette said.

"No comment," Damon replied.

"How's the weather outside?" their mom asked. "Does he need a sweater or a coat?"

"Ummm...I don't think so," Colette said. "Lemme check real quick, okay?"

She stood out on the front porch for a few seconds then said, "It's not bad, Mom. It's pretty warm for the end of October. I'd say we give him your black cardigan but he can just carry it over his arm with a purse."

"I'll go get both!" she said still smiling. "Just in case he gets chilly."

"His arms are kind of bony so it might be a good idea," Colette called out to her mom as she smiled at her...brother.

It was a quarter 'til six by the time Dillon was completely ready to go. Damon was already posting pics to the school website which he knew would have to be approved by a faculty member before anyone could see them. But they were all in good taste so there was no reason they wouldn't pass muster.

"You want me to post these on Facebook, too, bro?" he asked.

As he turned around and saw his best friend he laughed and said, "Or rather...not bro?"

"Smart ass," he said whacking Damon's head with the black bag his mother gave him to carry around the few things he might need.

Colette stepped in and said, "Before we go over to Mackenzie's, you really gotta work on that walk of yours. You can't just trudge around like a guy. Here. Watch."

Colette showed him how to walk, then walked the way Dillon normally walked. "See the difference? Watch my shoulders, my arms, and my wrists both ways." She walked like a guy again and then like a girl.

"Now you try."

The first two attempts brought howls of laughter from Damon and a more subdued version from Dillon's mother.

"It's harder than it looks, isn't it, honey?" his mom said.

"You're doing this with your arms," she explained by showing him how he walked. "Keep them in more like this, but don't 'hold' them in."

The third try was much better although still not even close to perfect.

"Good enough for Halloween!" Colette said. "Okay, let's get you outside and into the car. We don't wanna be late now, do we?"

Dillon couldn't take his eyes off the little mirror on the passenger's side the entire way there. More to the point, he couldn't stop looking at his eyes. They were a gorgeous blend of grays and a smoky black making them look sultry and sexy as hell. And then there was the glossy, dark-red lipstick. But it was more than any one thing.

He took another look then decided it was the entire face that held his attention. Or was it the soft, silky hair framing that pretty face causing so much disturbance 'down there'? In the end, he realized it was a combination of both, then suddenly became aware of how wonderful this beautiful dress felt on him or the way the high heels made him feel. The clicking sound they'd made on the concrete in the driveway as he walked out to the car was incredible.

As he continued staring at himself the thought hit him that he had never in his life ever felt so...right...before. But before he had time to sort through that thought, he dismissed the it when Colette pulled into Mackenzie's driveway.

"Nervous?" she asked.

"Oh, yeah," he said.

"Try and relax and just have fun tonight, okay?" she said encouragingly feeling very envious of her little...sister. "You really do look like a girl, you know. A very pretty girl at that."

Before his sister could say, "I hate you" yet again, he turned toward her and said, "Thank you."

"Ahh! You're so welcome, sweetie," she told him as she took another look at her new creation.

Dillon was getting ready to get out just as he noticed someone coming out of the house. This person's hair was long and slicked back, and he was wearing a tuxedo. Even so, there was no doubt that it was Mackenzie. As she walked up to the car, his mind was almost as blown looking at her as it had been from looking at himself. She really did look like she had a couple of days worth of dark stubble on her face, and because of the black and white outfit, he couldn't tell she had boobs. In a word, she looked pretty damn convincing as a guy.

"Let me get that for you, ma'am," she said in a faux-sounding deep voice.

She held out her hand and helped Dillon stand up. "Wow! You look...beautiful! Dillon? Is that really you?"

"Um, yeah," he said in his male voice while trying to keep his balance.

"Colette, you did an amazing job!" Mackenzie said. "Gimme a hug!"

Colette did just that and her heart ached to be able to hold the girl she loved knowing it was only for a few seconds.

"Thank you," she said. "And speaking of amazing! Dude!"

Both of them laughed before Mackenzie offered her arm to Dillon. "Please allow me to escort you inside, beautiful," she said with a big smile.

The only 'issue' Dillon noticed was how he was towering over Mackenzie. He was only 5' 7" but in the heels he was nearly 5' 10" while Mackenzie was only 5' 5" in the flat, black, patent leather shoes she was wearing.

Dillon did his best to walk as he'd rehearsed, but it really wasn't easy. The fact that Mackenzie didn't seem to care helped, but he was very afraid he was going to twist an ankle and be unable to run the final cross country races of the season the following week.

When they walked inside, her parents and her brother, who was there with his boyfriend, all broke into very loud applause.

"You must be Dillon!" her mom said. "Look at you! You are soooo pretty!"

Dillon smiled nervously and thanked her.

"And so brave!" she added. "Thank you for being willing to do this."

Mackenzie's brother came over and shook his hand. "Thanks, man. This is really great of you."

He then introduced his boyfriend who also thanked him sincerely.

"We need pictures!" Mackenzie said. "Come over here, Dillon. By the fireplace."

They posed for quite a few shots with Mackenzie on the large step to make her almost as tall as her date.

"Just one more!" Mackenzie said. She turned to her 'date' and put her arms around him and, without warning, softly kissed him on the lips. Dillon was taken by surprise to the point it shocked him, but when Mackenzie kept kissing, he finally kissed her back.

"You are so hot!" she whispered as it ended as cell phones clicked. "Oh, and you're gonna need to touch up your lipstick, sweetie."

Colette smiled but felt like she'd just been kicked in the stomach. Without another word, she quietly slipped out, got in her car and drove home as hot tears welled up in her eyes.

Was it possible Mackenzie was rejecting her in favor of her brother who, granted, looked like a girl, but wasn't, when Colette most certainly was and was willing to give herself completely to his beautiful high-school senior? It made no sense, and yet the way she had reacted to Dillon—especially the way she'd kissed him—told her it was true, and the more she thought about it the more it hurt.

Mackenzie, who didn't even notice her friend's departure, was holding her date's hand after the kiss then told everyone that it was time to get ready to go trick or treating.

Once the room emptied out, she said to Dillon, "You really do look pretty, Dillon. As pretty as any real girl I know."

She smiled at him then took his hands in hers and asked, "Would you mind if I gave you a girl's name? You know, just for tonight?"

His heart was pounding out of his chest as he stood there holding her hands after being kissed by the hottest girl he'd ever seen. He couldn't think of anything he wouldn't do to make her happy.

He smiled back and said, "No. I mean...I guess not. What are you thinking?"

"Well, since you're sooo pretty, I wanted to give you a really pretty name," she said. "I kind of like Peyton. So maybe...Peyton Ashley Freeman. It suits a beautiful girl like you, don't you think?"

Mackenzie may have looked like a guy to Dillon at that moment, but her eyes told him she was anything but. They were twinkling and so alive, and he knew he was powerless to resist. He knew he didn't even want to try and resist.

"Ummm...sure. That sounds fine to me," he told her.

"Great! Then Peyton it is."

She kissed him again then said, "I'd like it if you'd call me Ken tonight. Would you do that for me, Pretty Peyton?"

She brushed back his pretty hair and gave him that look.

"Yes. Of course I will...Ken," he told her.

"We're gonna need to work on that voice of yours, but for now, I guess it'll do."

She pulled him close then kissed him one more time. "Now be a good girl and go touch up your lipstick for me, okay?"

Colette had put everything 'Peyton' would need in 'her' purse so 'she' headed for the bathroom then realized she was tromping down the hall. She slowed down, paid attention to her arms, wrists, and shoulders, then took care of the task she'd been given.

"All ready, pretty girl?" Ken asked when Peyton came back out.

'He' was wearing his top hat and twirling a black and white cane.

"I know. I look like the guy on the Monopoly board, huh? he said smiling at her.

Ken offered Peyton his arm and escorted her out to his car. He opened her door and made sure her dress was out of the way before closing it.

When he got in and started the car, Peyton asked, "Macken...sorry. Ken? I was just wondering. Why are you doing this? With me? And...dressed like this?"

He smiled at her, put the car in reverse to back out of the garage, then said in his faux deep voice and with an evil smile, "I could tell you, but then I'd have to kill you."

Seeing the confused look on her pretty face, Ken said, "Just trust me until we're done trick or treating. Then you'll understand okay, gorgeous?"

There were a lot of smiles, surprised looks, and even one, "Get lost, you sick fucks!" as they went from house to house. Ken wasn't so much interested in candy as he was letting people know he was proudly supporting LGBTQ rights. But beyond that, he was doing this for a much more personal reason, one he wasn't ready to share just yet with the lovely Peyton.

For her part, Peyton loved all of the hand holding, the walking arm-in-arm, and the occasional kiss which she thought might have been mostly for show, done primarily for the benefit of those who enjoyed their very convincing, gender-bending portrayals. What she didn't enjoy were two feet that were killing her by the time Ken said that was enough for the evening.