Death of a Bachelor

When Jack woke up, the sun was shining in through the blinds, straight into his eyes. He rolled over onto the pillow beneath him, and it only took him another moment before he realized the bed beneath him wasn't his own. Deciding to finally open his eyes, he wasn't very surprised to notice he was only wearing his boxers, sheets covering the rest of his body. Sitting up and stretching his shoulders, he still wasn't able to register the room he was in. Looking around for clues, he was growing more and more curious as the simple, nicely decorated bedroom didn't bring back any memories. A bit of spilt wine on the hardwood floor did catch his attention, though, and the footprint leading away from it confused him even more. It was the shape of a normal foot, until it disappeared for a bit, and then ended in a small point where the heel should be. Jack stared at the spill for a few seconds longer, before he realized, oh, it was a high heeled shoe. To go with the spill, there were a couple empty wine bottles lying around, too, as well as some that had previously held champagne. Standing up and deciding to look for his clothes, Jack made his way through the apartment, looking around some more. He couldn't find his clothes anywhere. Peeking outside, Jack took in the bustling hallway, filled with absolutely nobody recognizable. Just as he was about to give up looking around and phone somebody instead, he spotted a bright pink sticky note on the kitchen table.

'Be back soon. XO.'

Suddenly, Jack began to remember his adventures of the night before. It all started at a boring college party, not too far away from his own home. He had spent the majority of his night standing around with people he barely knew, making small talk and drinking mediocre alcohol. He had a couple of his clothes friends with him, too, which was nice, but after a couple hours, all he wanted to do was go home. That is, until a certain stranger approached him.

"Where did you get that?"

Turning to face the voice that had spoken to him, Jack noticed right away that the brunet was just about the same height as him. It was notable, as Jack was a fairly tall person. As he began to give the other boy a look over, though, he realized he wasn't as tall as he had thought; the stranger was wearing shiny, black platform heels. They dressed up his tight, dark jeans and leather jacket quite well, and as Jack was admiring exactly how well his jeans fit his body, his legs in particular, he realized he had crossed a line. He wasn't looking anymore, he was staring.

"You like what you see?" The stranger asked with a wink, stepping toward Jack and watching him fumble with his words.

"Uh," Jack said, resisting a groan at his own stupidity. "Get what? What did you ask before?"

"The drink you're holding," the stranger nodded at the cup in Jack's hand, "I can't find anything at this shitty place, I think they're out."

"Oh," Jack blinked, "Yeah, I, uh, got it a while ago. You can have some, if you want."

"Thanks," the boy smiled back brightly, taking the cup, "I'm Alex."

"Jack," Jack mumbled, taking another moment as Alex took a sip to give him another look over.

"You're acting like you've never seen a guy in heels," Alex said, catching Jack staring once again.

"I don't think I have, actually," Jack recalled, and Alex hummed.

"Well, there's a first for everything, right?" He grinned, causing Jack's expression to mirror his own.

"I suppose. Is this a one time thing, or do you do it often?" Jack asked, genuinely curious.

"I wear them out every so often," Alex said, "And when I do drag."

"You do drag?" Jack repeated, and Alex laughed.

"Yes, that's what I just said. It's fun, and I get money from it." He explained, raising an eyebrow at Jack.

"Money?" Jack responded.

"Money," Alex nodded, "We do competitions on some nights, and whoever performs the best gets prize money."

"Sounds fun," Jack said, "Like an easy way to make money. It can't be that hard, right?"

"It's definitely hard," Alex narrowed his eyes at Jack, "And very competitive."

"Are you saying you don't think I could do it?" Jack chuckled, and Alex bit his lip.

"Not at all, honey. I was going to head over to one later on tonight at a bar nearby. Join me?" Alex asked, finishing his drink and placing the cup on a nearby table.

Jack shrugged in reply, asking, "What's in it for me?"

"$50 for whoever does better," Alex suggestion, and Jack thought about it for a moment, before shaking on it. It didn't sound like he'd be losing too much, that is, if he even lost at all.

"Don't threaten me with a good time." He stopped text his friends that he'd be leaving, and when he was finished, Alex took hold of his hand, leading him out of the house.

Jack had never heard of or seen the bar Alex brought him too, but he realized he'd probably passed by it many times in his life. It was fairly dark inside, and everything was brightly coloured, yet it somehow still held classy vibes. Alex walked Jack right past the bar, saying hello to a couple people, before bringing him through a door by the stage.

"Where're we going?" Jack asked, watching from behind as Alex walked down the hall in front of him, heels clacking on the tiled floor.

"My room," Alex answered, and Jack rose an eyebrow.

"You have your own room here?" Jack said, following Alex in after the unlocked one of the doors on their right.

"I do, hon. I might have played it down earlier. I do this quite often," Alex said, "Not just for the contests. Alright, let's get you dressed."

It took Alex a while to find Jack an outfit, as well as shoes that actually fit, but he was able to find a few things in his closet that worked. After only several minutes, Jack had traded his T-shirt, jean jacket, pants, and boots for a red, sparkly dress Alex had picked out, with silver heels to match. He finished it off with a cane and a top hat.

"This is the weirdest thing I've ever done," Jack commented, as Alex set off to fix him a blonde wig and do his makeup.

"It's not weird," Alex hummed, "Don't be rude."

"Alright," Jack agreed, "That was the wrong word. It's just new."

"Like I said," Alex smiled, "There's a first time for everything."

Once Alex was finished with Jack's hair and makeup, he dressed himself, keeping on his black heels and changing into a fluffy white skirt and a pretty pink blouse. He finished it off with his own makeup and a brown wig, and Jack decided Alex looked just as good as a girl, as well. Long story short, Jack absolutely bombed the contest. He could barely walk in his shoes, didn't necessarily know how to model at all, and was too shy to interact with any of the people watching, who were the judges. Alex, on the other hand, worked it like a pro, and ended up winning first place. It didn't look hard at all, all Alex did was walk around on stage, sort of like he was on a runway, occasionally stopping to wave and make faces at people. Apparently, he had forgotten to include the fact that this was a common thing for him, winning almost every time. Jack didn't mind.

When they were finished changing back into their clothes, Alex said, "You can keep the heels, they're too big for me."

"Thanks," Jack smiled, "I look great in them."

"You do," Alex nodded, "But you'd look even better if you knew how to walk in them."

As they made their way back into the bar, Jack spent a fair amount of the money he owed Alex on drinks for the other boy, before they decided to walk back to Jack's house. To his dismay, he had forgotten his key at one of his friend's houses, where he had been before the first party. Maybe it was a good thing, because Jack wasn't sure how his parents would react to him bringing Alex home so late. He wasn't really the type to do so. At twenty-two, bringing home somebody that was also his age, he didn't think his parents would mind, but he was a polite boy. He would stay over at other people's places, instead. Being the creative thinker that he is, though, Alex took the chance to hop the fence over to Jack's neighbour's yard, throwing off his shoes and clothes, and diving into the pool. Jack's neighbour's were an elderly couple who were probably in bed, and he knew they wouldn't mind him using their pool anyway, but he still followed Alex to scold him for being such a disturbance.

"Relax," Alex giggled, as Jack stared down at him, "Loosen up, baby."

Loosen up, he did. Jack ended up following Alex into the pool with little coaxing, and they floated around for a bit, before deciding to call a cab back to Alex's apartment. Jack was surprised when Alex invited him over at first, but then he realized he was still locked out of his house, and it was just common curtesy. Most of him was sure that Alex would have done it either way, though. The rest of the night was a blur, and it turned out exactly as expected. Returning to Alex's place at nearly three in the morning left room for only one thing, and Jack was well aware of it as he found himself being pressed up against the wall, Alex's lips pressing kisses and sucking on his neck.

"I'm going to suck you off," Alex whispered into his ear, his hand moving down to rub Jack through his jeans, "And then you're going to fuck me. Sound good?"

"Sounds great."

Notes

suh dudes! this was the part i was most excited to write, and it turned out exactly how i wanted it to. i hope you all liked it, too!!!

also, since i'm having so much fun with this, i've decided to finish this before i revamp Ocean Avenue :^)

lastly, i probably won't be updating in the next two weeks, because i'll be away. sorry!

thanks for reading <3