Prom Queen

*Author's Note: I shared my own very unique love story in Serendipity. I got into crossdressing late in life compared to most guys who start somewhere between 5-15. I was married, and had been on active duty for four years and was totally into weightlifting since my sophomore year of high school. When I first tried wearing women's clothes, I was in my early 20s, so I suppose that's 'late'.

After my divorce, I swore I'd never, ever get married again. I got quite proficient at makeup application very early on and was quite passable even before I grew my own hair out. I shared some of those experiences in stories called By the Grace of Guile and Cruisin' for a Bruising. The latter story proved conclusively that I was not a transsexual and that I had no desire to live full time as a woman. That is still the case today, but I do 'transform' every other day, and for special occasions for the woman I love.

Post divorce, I dated only men for several years, and then, before a marathon, I met a beautiful, female Navy officer, who is 'bi' but mostly gay. Long story short, her biggest fantasy, once she discovered who she really was, was to meet a guy like me; someone who looked like a woman but who had...something special. I'd never even considered ever meeting another woman who would accept, let alone love, my little hobby. She did and this works for both of us quite well.

This story is an ode to my life with her, the woman I married several months ago. I know. I know. But hey, she asked me five times, and I really do love her, so I finally gave in and said 'yes'.

She tells me I was a very beautiful bride, and I'll take her word for that, but I can say with certainty that she most definitely was.

*****

Early October, 2014

"Please? Just this one time? Come on, it's Halloween."

"Sorry, that's not happening," he told his sister.

"But Mackenzie is the one who suggested it," she said.

Just the mention of her name made him stop and pay attention.

"Are you serious?" he said very seriously.

"Yes, I'm serious. In fact, she said you were super cute."

"Don't jerk my chain, Colette. I'm not buyin' it."

He paused, looked at his sister, then asked, "Mackenzie really said that about me?" not sure he should believe his older sister. She'd pranked him several times over the years, and although he'd gotten her back quite a few times himself, he couldn't take her word for anything.

"Dillon, I'm serious!" she insisted.

"Mackenzie said I'm super cute?"

"Well...kind of."

"Oh, okay. Here it comes. What's the punch line?" he said knowing the other shoe was about to drop.

"Well...she said you'd be super cute if you dressed up like a girl."

"Give me a fucking break!" he said. "I knew this was bullshit!"

He started to walk away when his sister said, "She said she go out with you if you did that."

He stopped but didn't turn around or speak.

"All you gotta do is walk around with her for a couple of hours on Halloween. Look, you know her brother, Max, graduated last year with me, right? He and I go to college together. Okay, it's just community college, but still. Anyway, he's gay and just came out like a month ago. Mackenzie is trying to show her support by pushing gender boundaries. She wants to wear this Top Hat and tails costume. She's gonna have a fake beard using coffee grounds for stubble and she's gonna look really convincing as a guy. She wants a...a fake girl who can look convincing to go with her."

"So...that's where I come in, right? I'm the um...'convincing' girl?" he said as he used his fingers to exaggerate the air quotes around the word convincing.

"Well, you could be. I mean, you are pretty small for a guy and you run cross country so you're like super skinny. And your hair is like really long and I'd kill to have your eyelashes," his sister said. "So, yeah. I think you could pull it off with the right kind of help."

"Let me guess. You're talking about hair, makeup, a dress, fake boobs, and the whole nine yards, right?"

"How else are you supposed to look like a girl, doofus? That's the only way you're gonna looking convincing. You can't just throw on a dress and a lopsided wig and look believable. We'll get you all dolled you up and make you look super hot."

"And what do you get out of this? You always have an agenda, Colette. What is it this time?"

"I have my reasons," she said coyly. "Maybe if you agree to do this, I'll tell you."

"She really said she'd go out with me? Mackenzie Davis said that?"

"Yes, she did," Colette reassured him. "So you not only get to hang out with her while you're trick or treating, she'll go out with you just for playing along. It's that important to her."

"So it's not like she's into me for who I am, but for something she thinks I could temporarily become, which is really for her. Which is actually really all about you. Is that about right?" Dillon asked, the sarcasm dripping from his words.

"Take it or leave it," she said knowing he'd had a crush on Mackenzie Davis for a very long time.

He finally turned back around then said, "Don't even think about punking me on this, Colette."

"I won't. I swear. She just really, really wants to do this with you. So...will you? Please?"

"Fuck," he said knowing he'd do damn near anything to go out with Mackenzie Davis. "What do I have to wear?"

"So you'll do it? Really?" his sister said as her level of excitement grew.

"If this is legit, then yeah, okay, sure...I guess. Tell me more about this first, and then I'll let you know for sure," he said before sitting down.

"I pretty much told you everything I know, Dillon. Mackenzie is supporting her gay brother, this is the way she wants to do it, she thinks you would be a very cute girl to her boy, and she'll go on a real date with you if you'll do this. End of story."

"Okay, but why didn't she tell me this herself?" he wanted to know.

"My best guess is she thought it might be easier for me to convince you to do it than if she did it herself. Either way, you get the same results, right?"

"I don't know. I mean, guys have given me shit about looking like a girl since...well, forever. The last thing I need is to give them more ammunition."

"Look, Dillon. You're 18 now and a senior in high school. Trust me, in six or seven months, these people will mean nothing to you except for your closest friends. High school is a phony, make-believe world of clicks and smart asses whose best days are high school. They're losers, so who cares what they think? The question is, do you want to go out with Mackenzie Davis or not?"

"Well, yeah. Of course, I do. What guy wouldn't?" he replied. "But this is just...fucked up."

"Okay, think about it. Just don't think too long. Halloween is coming up and you're either in or you're out, and if you wait too long, she'll just find someone else. And if you're out, you'll never go out with her."

His sister laughed then said, "Or ever get in Mackenzie, if you catch my drift."

"Bitch," he said only half joking.

"Oh, grow up, Dillon. You've liked this girl forever, and now you have a chance to not only finally meet her but to go out with her, and if she likes you back, you're in. Maybe...all the way in, right?" Colette said with an evil smile.

"And you really would make such a cute little girl," she said pinching his cheeks just under the high cheekbones she also envied.

She looked at her little brother then said, "You know you make me sick, right? It isn't just your eyes. I'd kill to have your face!"

"Fuck off," he said with disgust as he walked away as his sister laughed loudly at his expense.

That night, Dillon's years-old fantasy about Mackenzie Davis took on new meaning. He had no idea how many times he'd already jerked off thinking about her, but he also didn't care. What he did care about was finally getting the chance to be near her, no matter how screwed up the reason for it might be. And once he got close to her, the 'snowball's chance in hell' he'd given himself for ever scoring with her went up exponentially. Or at least a little bit, a little bit was a whole lot better than the big fat zero it had always been.

The next day, he realized he needed to talk this talk this out with someone, and there was only one person he trusted enough to tell without it being retold and blabbed all around school.

"Dude? Are you seriously thinking about doing this?" his best friend replied.

"Yeah, I am. Well, maybe. What do you think? I mean, would you do it for a chance to go out with Mackenzie?"

Damon Ferguson had been Dillon's best friend since moving to his neighborhood back in the fourth grade. Like him, he ran cross country and track, and like Dillon, was rail thin. Both of them had dated girls, but neither had ever had any real shot with someone as cute as Mackenzie Davis. She'd recently broken up with the guy every girl in school said was the hottest of the hot, so she was definitely available. But why would a girl like that ever be interested in a guy like Dillon Freeman?

"I don't think I'd have the balls to do it, bro," Damon told him. "Not even for a shot at the hottest girl in school. How do you know she'll even go out with you if you do agree to dress up like a chick?"

"I don't," he replied. "And that's the problem. Well, that and all the added crap I'm gonna end up getting from the guys once this gets out."

"Okay, what if you...owned this?"

"Owned it? What the hell are you talking about, man?" Dillon asked shaking his head.

"Instead of being all passive and afraid, what if you stand up loud and proud? What if you say, 'Hell yeah, I'm doing this! I'm standing up for people like Mackenzie's brother. I'm standing up against hate and bigotry. I'm proud to be taking a stand for gay rights and I'd like to see more people do the same thing. I mean, you don't have to be gay to support gay rights...right?"

Dillon sat there for a moment thinking then looked over at his friend and said, "You know what? That might just work."

He smiled at Damon then told him, "You're not as dumb as you look."

"I have my moments," Damon said proudly jutting out his jaw.

Getting excited, Dillon sat up straight then said, "Actually, that's actually pure genius! I don't have to believe any of that crap. I just have to say it like I do!"

"Yeah, you'll be a hero to a whole lot of kids in school and the few who want to give you shit about it will be too afraid once they know this is about gay rights."

"Yeah, this might just work!" Dillon said. "High five, dude!"

While Dillon was getting feedback from his best friend, Colette was providing some to Mackenzie who texted her demanding an update.

"So how did it go with your brother?" Mackenzie asked once Colette showed up in person.

"I think he's in," Colette said.

"Really? Cool! Thank you so much!" she told her. "That is like so awesome!"

"You're welcome," Colette said as she moved closer and brushed Mackenzie's pretty blonde hair back. "So...is there anything in this...for me?"

"You're like super hot, Colette, and I'm very interested, but I kind of have my eye on someone else."

"So let me get this straight. You tell me you're gay, you ask me to talk my brother into doing this to support you supporting your brother—who is also gay—and you shoot me down just like that?"

"It isn't you," Mackenzie said, playing with Colette's pretty, long, dark hair. "I just have this...this thing I can't really talk about. But if I didn't...if I didn't really like someone else or something about them I think I really like...I'd be with you in a second."

"Could I at least have one really nice kiss as a thank you?" Colette asked.

Mackenzie smiled then leaned over and pressed her soft, full lips to Colette's and left them there for 2-3 seconds before pulling away. "Thank you, Colette. And thank you for not outing me before I'm ready."

Colette was still reeling from the kiss. "Wow. That was like the best kiss—ever."

"Yeah, it was nice, wasn't it?" Mackenzie agreed. "You are so hot and lots of girls are going to be dying to go out with you. Just be patient, okay?"

"Even if you're the only one I want to go out with?" Colette said back.

"I know it's hard to want someone who maybe doesn't feel the same way, but...I just can't. I have to know if this special someone might really be...special. Okay?" Mackenzie knew Colette was hurting so she kissed her one more time only this kiss was long and slow and very passionate.

"I am so in love with you," Colette said as their lips parted.

"You're just infatuated, sweetie," she told her. "And thank you again."

"Yeah, sure," Colette said, her voice heavy with sadness. "I mean, what are...friends for, right?"

"So..when are you going to come out?" Mackenzie asked.

Colette didn't know the answer to that question. She also understood she was never going to be anything more than Mackenzie's friend. Further, she knew full well that she would do anything this beautiful, younger girl asked her do as she was helpless to refuse her anything—large or small.

******

October 31st

"So once your sister finishes...transforming you...you want me to take some pics and post them to the school's website, right?" Damon asked just to make sure.

"Exactly. And you have the words to go along with the pics, right?" Dillon told him.

"Yep. Right here in my hot little hand. You'll be bold and unashamed, standing up for the rights of the gay and transgendered communities."

Damon paused for a second then asked, "Dude? You're not gay, are you?"

"Jesus, fuck! No I'm not gay, you dumbass. I'm in love with Mackenzie Davis. What's wrong with you anyway?"

"Okay, okay. Just...checking, that's all. Don't blow a vein in your head or something. Sheesh."

"And for your information, I've been doing some research on this crossdressing stuff, and it seems like most of the guys who are into it are straight," Dillon informed his friend.

"No shit? That doesn't make any sense to me," Damon said. "Why would a guy want to look like a chick if he doesn't want to attract guys?"

"I don't know, man. All I know is what I read and that's what it says. Oh, and crossdressers aren't the same as transsexuals, many of whom are gay except that they're not because they think they're actually women stuck in the wrong body."

"This shit is confusing me big time, man. All I know is I like pussy," Damon said the way most typical 18-years spoke.

"Yeah. I hear you, bro. I got no interest in sucking some guy's dick. I mean, if that's what a guy's into, that's cool. But I am most definitely not into that."

"So when's your sister getting started on this 'Transformer' project?"

"Anytime," Dillon said. "I'm supposed to hook up with Mackenzie around six at her place so..."

"Dude? Newsflash. You ain't hookin' up with Mackenzie Davis."

Dillon shook his head and said, "Sometimes you can be so obtuse."

Damon had no idea what 'obtuse' meant, but he thought he caught his friend's drift. "Did you just call me stupid, bro?"

"If the shoe fits..."

"Yeah, well fuck you and the horse you rode in on," he shot back just as Colette walked in.

"Hello, boys! So...are you ready, Dillon?" they heard Colette ask.

"I'm leaving until you're all dolled up, dude. I don't think I can stand to watch the process."

Dillon held up a hand and said, "No. Hang on. You should take some before, during, and after pics. That'll be even better. You know, let people see how much pain and anguish I'm willing to go through to support the LGBTQ community."

"Yeah, and LMNOP to you, too, buddy," Damon said trying to be cute.

"Okay, let's do this!" Dillon told his sister as Damon followed them with his cell phone to take the pictures his best friend asked for.

She led him back to her bedroom and on the way his mother passed them in the hall and said, "You must really like this girl, honey."

"Oh, he's got it really bad for her, Mom," Colette interjected failing to mention she also had it bad for Mackenzie Davis.

She had no idea why she'd suddenly realized she liked girls after having dated boys all through high school. She just knew that she did. And after having first one and then a second amazing experience with girls from college, there was no turning back. Colette liked women and that was that. Telling her mom was a different story entirely, and that helped her understand and appreciate Mackenzie's concerns even more.

"Well, have fun," she said. "I always wanted another daughter so tonight I can pretend for a little while, right?"

"Come on, Mom. Not you, too? Gimme a break, would you?" Dillon said as Colette dragged him along.

Once they got into her room, Dillon stopped and stared.

"I'm wearing that?" he said pointing to a beautiful black, lacy dress laying on her bed.

"Um...yeah. Mackenzie's wearing a tux so you need to be in a beautiful dress. This one is perfect because it doesn't show any cleavage, but it's long and slinky with a really nice slit up the side."

She held it up and showed it to him then held it against his very-thin body.

"Just as I suspected. A size 6 looks perfect. Well, after we give you some hips and a butt, and some boobs."

She laid the dress back down on the bed then said, "Okay, first thing is go take a shower and shave your legs and any other hair that isn't on your head. Underarms, chest—not that you have any hair there... Just shave everywhere. Oh, and shampoo your hair and towel dry it, but don't use the blowdryer. Got it?"

Dillon really did have very little body hair other than a few dark strands under his arms. He shaved maybe once a week and even that was more out of some kind of hope that shaving might make his facial hair grow in faster so he'd actually need to shave than out of necessity.

His chest was virtually hairless with just a handful of light-colored hairs over the breastbone. One stroke of the razor would eliminate them for weeks. His legs did have hair on them, but it was very light and and very sparse. They didn't really need to be shaved, but if this was the way to get a date with Mackenzie Davis, he'd shave them all day, every day.

Thirty minutes later, he came back having done exactly what his sister had asked him to do. "Okay, so now what?" he asked standing there with a towel wrapped around his waist and his almost shoulder-length hair still very damp.

Damon snapped a couple of pics before Colette got started then sat back and found himself unable to avoid watching.

"Now, we get serious," Colette said.

She had some kind of undergarment thing in her hand, and there was a large block of some kind of soft, spongy material on the bed. Colette measured him in several places then cut out four pieces of whatever the material was and told him to put on the undergarment.

"Turn around," he told her before again doing what she'd asked.

"Okay, I'm gonna put these two in your butt area and one of these on each side, and you'll have a very nice ass and a set of hips."

Colette made some adjustments then took a final look. "Perfect!" she said as she looked at her brother from the back and the side.

"Now...pull the pantyhose on but be very careful not to run them. Here, let me show you how," she said as she rolled one leg up. "Point your toe then carefully slide it up your leg then do the other side."

In less than a minute, Dillon's legs were covered in a barely-black shade of nylon which would go perfectly with his dress while allowing his freshly-shaven legs to be seen.

"And now we need a bra," she said. She grabbed one of her own which was a 34C in black and said, "I don't know whether it's good or bad, but we both wear a 34. I guess you're lucky I'm not an A-cup, huh?"

She had him slide his arms through then hooked it for him in the back.

"Oh, fuck me," Dillon said looking at himself in the mirror.