Sometimes you have no idea what's gonna happen when you're asked to do...

-----

“This is so stupid,” I told myself for probably the tenth time in the last half-hour. Nevertheless, I planted my elbow on the counter, held my hands steady, and went to work.

Carefully, ever so carefully, I traced the line of my upper lid on my left eye with the slick, wet eyeliner, drawing the wing out almost to the tip of my brow. Satisfied, I did the same on the other side, then went back to the first eye, being equally careful as I did a thin line under the eye as well… then back to the left to repeat.

Good enough, I assured myself, nodding in approval at the results.

Not that the quality was a surprise. I’d been practicing this look for weeks in preparation for the coming party, spending hours pouring over tutorials, trying different brands and styles, and figuring out what worked for me.

I was being paid to do it, so I might as well do it right, after all.

“Are you almost done in there?” Jacob called through the door, not so much pleading as amused.

“Hey, I told you this was gonna take a while!” I yelled back, getting a laugh in response.

Rolling my eyes, I walked over to the door and unlocked it, letting it swing open on its own.

“Yeah, but-- wow,” Jacob said, stepping back when he saw me.

“That bad?”

He laughed again. “You know the answer to that. You look stunning, and Buddy doesn’t deserve you.”

“You’re damn right about that,” I muttered under my breath but smiled as I pushed past him. “Bathroom’s all yours.”

“Thanks, Reese.”

“No problem,” I said, walking over to the little island in our apartment and propping myself up on one of the stools. “Just don’t move any of the stuff on the counter; I need to pack some of it in my purse later and don’t wanna forget anything.”

“Righto,” he said, even as the door closed behind him, and I almost immediately heard the sound of him whizzing.

Probably didn’t even lift the lid first, I thought with a frown. Rather than worrying about it I reached for the glass of wine I’d prepared myself before starting. My nails made a gentle clinking noise as their dark red tips made contact with the glass, and I had to mentally kick myself for almost making a mess.

“This is so, so stupid,” I said once again, lifting the glass to my lips and taking a sip. I didn’t need to look down at it to know there’d be a lipstick mark on the lip, in the same dark red as my nails. “But at least I’m getting paid for it.”

I’d told Buddy it was a fool’s bet when he’d made it, but he’d never been one to let a little logic get in the way of a good challenge.

It was a year ago, but I could still replay the whole sequence of events in my head as though it were only last week….

-----

“You’re a goddamn idiot.”

“I know,” Buddy agreed, taking a swig of tomato juice and wincing.

“Like, a world-class one.”

“I know!”

“Then why did you—”

“Hey, you weren’t there!” He said, flinching at the volume of his own voice. “Can we have this conversation after my hangover?”

“Nope, ‘cause you deserve to suffer both,” I countered, trying not to enjoy my friend’s discomfort too much.

“Bitch,” he tossed back at me as though that were an insult.

“Don’t hate me because I’m beautiful.”

“Yeah, well, it’s 10 AM. Why are you still dressed like that?”

“Like that,” in this case, referred to the green-sequined cocktail dress I was wearing, with the three-inch heels, and padding in just the right places to give me a nice if not overwhelming figure.

“It was a helluva New Year’s party,” I said, as though that explained anything.

“And your girlfriend wanted you to—”

“Yes, yes she did,” I said happily. And it was the truth – she had been the one who’d insisted I left her house fully dressed again that morning. Given how the night before had played out, I’d only felt it honorable to oblige.

Buddy shook his head and took another half-hearted sip of his tomato juice. “Fuckin’ hell. I can’t even find a girl who’ll date me, and here you are dressed up like a goddamn supermodel because that’s how your girlfriend likes her guys.”

“Plenty of girls date you,” I pointed out. “They just won’t go out with you more than once.”

“And why is that, oh, font of knowledge?” He asked me sarcastically. “Since you seem to understand girls so well?”

“One.” I ticked a finger. “You’re a pompous asshole. A rich pompous asshole, but still. Two, you’re good at pick-ups but terrible at keeping the charm on past that. Three, you’re not as good-looking as you think you are.”

“Hey now—”

“Four,” I continued, cutting him off. “You only go for supermodels and rich girls, neither of whom have any reason to put up with your shit.”

“I mean—”

“And lastly,” I said, ticking off my thumb, “you don’t know when to take ‘no’ for an answer, so you push until any goodwill you might have had is burnt up because you wouldn’t stop getting handsy.”

Buddy sighed. “So, basically, I’m undatable.”

“No. You’re just a dickhead, and need to learn to treat folks better,” I said a bit more softly, then patted his back a bit in commiseration. “Not that I think this deal’s gonna help any.”

“What was I supposed to fuckin’ do?”

“I dunno, maybe not promise your folks you’d be engaged by the end of the year?!”

“And give up my trust fund? Are you crazy?!”

The look in Buddy’s eyes told me he truly thought I was. Then again, the idea of having to work for anything had always given Buddy indigestion.

I shrugged my shoulders. “Hey, you’re the one who came over here to talk about it, it’s not like I made you leave your apartment with a hangover, drive to our place, and drink tomato juice.”

“But you are making me drink the tomato juice,” he argued, taking another sip, this time with less objections.

“Nonsense. I just told you that you could either drink it or leave. Not the same thing at all.”

“Whatever,” Buddy said, sounding defeated. “It is helping though, thanks.”

“See? Listen to Momma Reese, I know what’s good for you.”

“Don’t push it,” he said but smiled – just a little – around another sip of the tomato juice. “But really, what’s up with the getup? Not that you don’t look good.”

I shrugged. “Lily wanted to take me to a lesbian club for New Year’s, ‘cause a lot of her friends were gonna be there. I argued I wouldn’t fit in, so.” I waved down at my outfit. “She liked it. They liked it. Was a lot of fun.”

“Your girlfriend’s a dyke, you know that, right?”

I glared at him but didn’t correct him, only because she used the same word for herself. “Who’s more manly, the guy who can’t keep a straight girlfriend, or the guy who can keep a lesbian one?”

“Got me there,” Buddy admitted with a sigh, then growled as he slammed our rickety card table with a fist. “But… shit. Whaddamigonnado?”

“Weeelll….” I thought. “You’ve got a year, right? And you just need to be engaged by New Year’s, not any particular amount of time ‘til then, right?”

“Two weeks,” he said, grimacing.

“Two weeks before?”

He nodded.

His parents are smarter than I thought. “Okay. Well, still plenty of time to work on your charm, figure out how to keep a girlfriend, and maybe find The One.”

“You really think I can do it?”

“Not a chance,” I admitted bluntly, enjoying watching him squirm a bit. “And we both know your parents are big enough assholes to hold you to it, too. But ya gotta try, right?”

He nodded silently, then gave me a weird look.

“What?”

“Listen, just… on the off chance I can’t.”

“No.”

“It’d only have to be for—”

“NO.”

“Twenty grand.”

“We’ll talk about it in November,” I said quickly, before I could change my mind. “Until then, I’ll do everything I can to help you do better with the ladies.”

“Thanks,” he said, downing the last of his tomato juice and giving me a relieved grin.

-----

He did not, in fact, do better with the ladies.

By the time November rolled around I was already resigned to holding up my end of our little deal, if he was to his. As proof, he’d shown me his savings account balance, so with Lily’s help I’d began preparations.

I’d expected her to object, but instead….

My phone ding-ed at me as I sat perched on the stool, and when I looked at it I couldn’t help but smile.

“Hey babe,” the text read, “at the club with the girls. Showed them pics of your dress and they wanna see you all decked out. Selfies?”

“K,” I texted back, then held the phone out and took a couple of pouty pictures of myself, sending them her way.

Almost immediately five more dings came from my phone -- one from her, and four more from some of her friends, all of them full of hearts and smileys and, in one girl’s case, an eggplant emoji.

Another ding, this time with more text. “Sad your not here, but make that money and see you tomorrow. Hugs.”

I sent “Hugs!” back, then checked the time on my phone. Only a little annoyed, I used the speed dial to call Buddy.

“Yeah,” he said brusquely, answering on the third ring.

“Hey, where are you, it’s nine thirty and I thought we had to be there by ten?”

“Around ten,” he said back, sounding annoyed. “And I’m on my way.”

I’d figured that much from the sound of traffic coming over the speaker, but didn’t say it.

“You wearin’ the tits?”

I frowned at that. “Of course I am. You paid for ‘em, I’m wearin’ ‘em. And the dress,” I added, a little annoyed myself.

“Good. I’ve always wanted a big tiddy goth girlfriend, and that’ll be enough of a nightmare for my folks that when we break up they’ll be praising me for it.”

“If you think so,” I said back, not so sure. “Just make sure my twenty grand is in my account before—”

“Yeah, yeah. I’ll transfer it first thing next year.”

I rolled my eyes. “Very funny.”

“Be there in ten.”

“A’ight. See you then.”

“Yep.”

*CLICK*

I picked up my glass of wine and took another sip. If Buddy said ten, it’d be twenty, guaranteed.

“Big tiddy goth girlfriend,” I said aloud to myself, and rolled my eyes again. “I shoulda never agreed to this outfit,” I added, picking at the black velvety material and stretching it just a bit, then letting it go so it popped my thigh.

Usually when I’d dress up with Lily we’d go for more of a natural look, with only a bit of padding on my hips and some cheap foam forms to fill out my chest, but Buddy had insisted that wasn’t good enough for him. I’d thought the E-cup forms were excessive, but it was the smallest size I’d been able to talk him into, and he’d only agreed then when I pointed out that I couldn’t wear a dress that showed any cleavage even at that size, since the edge of the forms – and the weight – would be too much.

That was a bit of a lie, and Lily had loved how naturally we’d been able to blend the forms into my own skin... but he didn’t need to know that.

The dress, combined with a bit of padding in my ass and hips, went a long way to giving a Certain Vibe to my look. Lily had tried to help me class the whole thing up a bit with some nice jewelry and a makeup job that was on the goth side but not too over the top, but it was still Buddy’s choice of dress, and… well, he’d made up for the “no cleavage” mandate by having as little material below the waist as possible.

I wondered for just a moment how worried I should be that one of my best friends had wanted me to meet his parents wearing a dress that was barely long enough to hide the tag on my panties… but hey, it was his money to spend and lose.

And I did look hot as hell.

As if knowing I needed confirmation, Jacob looked over at me from where he was playing Xbox on the couch and gave me a goofy thumbs-up and a wolf whistle.

Yes. Yes I did.

-----

Twenty-two minutes later Buddy pulled up and honked.

He rolled down his window as I walked toward his car, and whistled at me. “Hey babe, lookin’ for a good time tonight?”

“Shut the fuck up,” I told him, pulling the coat I’d borrowed from one of Lily’s friends tighter around me as I circled the car and popped the door. “I’ve been waiting outside for you for almost ten minutes, and been propositioned three times.”

“I’m glad you held out for me,” he said, taking off before I even had my belt on.

“You’re paying better.”

“Touche’.”

I reached over and turned the heat in the car up a few notches, getting a glare from Buddy over it, but I didn’t care – he wasn’t the one wearing the dress and hose.

“So, last check on the plan,” I said, rubbing my hands together in the warmth from one of the vents. “We go, we schmooze for a couple of hours, we get drunk enough we can kiss each other, then we fight and you bring me home.”

“Pretty much, yeah,” Buddy agreed, reaching over and squeezing one of my too-exposed thighs. “Though it’s kinda a waste you got a dick. Watchin’ you walk around the car was a treat.”

I removed his hand from my thigh and shot him a look. “Hey. Watch it.”

“What?” He said, leering at me. “It’s all part of the deal, isn’t it?”

I shook my head. “Y’know, if you didn’t treat girls like this you mighta had an actual date for tonight, instead of having to pay me to do it.”

Buddy laughed at that, and not in a kind way. “Hey, not my fault bitches act all hot ‘til I put ‘em on the spot, is it?”

I looked away, trying to hide my feelings of disgust. I was absolutely sure that I knew a few ladies who could change his mind on that real quick.

“So what kind of party is this anyway?” I asked after I’d had a few moments to calm back down.

Buddy snorted. “Just one of my folks’ stuck-up bullshit things. I only go every year ‘cause I have to, but here’s hoping that changes after tonight.”

“Your folks probably aren’t gonna like your ‘engagement’ going just long enough to win y’all’s deal.”

“Eh, they’re business-people. They’ll respect it. Oh, speaking of respect.” Buddy pulled a small velvet box out of his jacket and tossed it to me. “You said a size seven, right?”

“Yeah,” I agreed, catching the box and opening it. “Ooooh.”

“Nice, right?”

“Very,” I agreed, taking out the ring and sliding it on. Rose gold, with a single flawless ruby in it, the ring sparkled prettily on my hand.

Buddy nodded. “Just be sure to give it back to me after the fight so I can return it. Unless you wanna knock four K off your price?”

“No way.”

Buddy smirked, then reached over and squeezed my thigh again. “Then again, I might be willing to let you keep it if—”

I removed his hand again, less gently this time, and jacked the heat up a bit more in the car. “Jeezus fuck, Bud! No!”

He rolled his eyes. “Come on, dressed like that, don’t tell me you don’t dream of sucking—”

*SMACK*

I grabbed the dash as we swerved, the breaks squealing, but Buddy got the car back under control with no issues, and only a smattering of honking horns.

“The fuck!”

I pulled the ring off and dropped it in the cup holder of the car. “Fuck this. Pull over and let me out.”

“Oh, come on, Reese, you’re not—”

“Now, Buddy!”

Buddy shook his head. “We’re in the middle of the fuckin’ highway! Just… listen.”

“I knew this was a bad idea,” I said back, pulling my phone out of my purse. “This isn’t worth twenty grand, and—”

“Hey, I’m—”

“—should call the fucking police about—”

“HEY!”

“What?!”

Buddy sighed, and actually looked contrite for once. “Thirty grand.”

Pause.

I looked down at my phone, and the half-finished text on it.

-----

“Mom, Dad? I’d like you to meet my fiancee, Reese Carlton.”

“Pleased to meet you, Mr. and Mrs. Langdon,” I said, giving them a small curtsey while I kept my left hand – and the ring – conspicuously laying on top of my breasts.

“A pleasure,” Mrs. Langdon said, reaching out for a gentle handshake, that I happily returned. She was a tall and somewhat severe looking woman, but she had Buddy’s green eyes and nose.

“The same,” said her husband, a more solidly built man who was like a salt-and-pepper version of Buddy himself, but with blue eyes. He took my hand as well, but held it just a little too long. “Reese, huh? Like the candy?”

“Like the actress,” I countered, glancing sideways for his wife, but she had seemingly already turned away to talk to someone else.

“Equally delightful,” he said, not even trying to hide the lust in his eyes as he looked down at my chest, then further down at the too-short hem of my dress.

Like father, like son.

“So,” Mrs. Langdon said, turning her attention back to me. “You and our Buddy are engaged?”

“Yes,” I agreed. “A month now.” I flashed the ring again, and my best smile.

“I must admit I was a bit surprised when he told us,” her husband said, taking a glass of wine off a passing tray. “We’ve heard him talk about his… friend Reese before, but we always assumed you were a man.”

I grinned at that. “I can’t imagine what would give you that impression.”

“Neither can I,” he agreed, once again giving me a leering once-over. “Nor can I imagine what kept you two apart for so long.”

“My girlfriend,” I said, causing both Buddy and his father to hiccough in the middle of their drinks.

“Girl? Haha! That’s my boy!” Mr. Langdon said, reaching over and clapping Buddy on the shoulder even as Mrs. Langdon’s expression become just a little more disapproving.

“Oh, so you’re… bi… whatsit?” She asked me with false brightness.

“Not really, but how could I say no when Buddy asked me?” I said, with my own false brightness, being sure to bounce my tits just a bit more than necessary at the same time. Not that I was going to tell them what he asked me.

“I… see.”

It was a few more minutes of awkward conversation before we managed to extract ourselves from his parents, moving to cousins, then business partners, then uncles and aunts, before finally making our way to the small dance floor at almost a quarter past eleven.

“Jeezus,” I muttered, pulling Buddy close – and ignoring a particular protruding annoyance when I did so – so that we could talk more privately.

“You’re doing great,” he assured me, sneaking a covert squeeze of my ass while he thought I couldn’t retaliate, and barely groaning when I nailed his toes with one of my heels. “They buy it.”

“I think they’da bought it if you’d brought in a hooker,” I said, looking around at the other women at the party. I’d thought when Buddy had shown me the dress he wanted me to wear I’d be the sluttiest look at the deal, but it seemed like a lot of the fifty-something businessmen had payed for their dates for the night too… probably with more fringe benefits than I was giving Buddy added to the cost.

“So you’re saying I’m overpaying you?”

“I’m not a hooker.”

“Not yet.”

This time I stomped a little harder, and had to hold him up when he almost collapsed on the floor.

“Should I lead?”

“Motherfucker.”

“Not with the way she was looking at me.”

He chuckled at that. “Yeah, well.”

“Your dad, on the other hand.”

“I told you the tits weren’t too big.”

I sighed at that, and covertly checked the little feminine watch I was wearing. “We gonna dance for the next half an hour, or go get more drinks?”

“Drinks.”

“Thank God.”

We ended our dance, and I did my best to give Buddy the most lovey-dovey look I could as I nailed his pinky toe one more time with my heel, getting an equally loving grimace of pain in return.

The wine was decent, but not great. I’d expected better of such a fancy to-do, but we were over two hours in to the party, so I imagined they weren’t running the top shelf drinks at this point. I sipped on my glass while Buddy downed two of his own, then went for a third, all the while continuing to drag me from group to group, sneaking gropes in whenever he thought he could get away with it.

There was a projector set up on one wall, and on it we could see the live feed of the ball in Times Square. As the midnight hour approached, Buddy not-so-subtly began to guide us back over to nearer his parents.

The countdown began, and we embraced each other once more.

“You ready for this?” I asked him through a false smile that made my dimples hurt.

“Abso-fuckin’-lutely.”

“My money?”

“On its way.”

The ball dropped, the room cheered, and I wrapped my arms around Buddy’s neck as the lights in the room went crazy. He grinned smarmily as he pulled me close and kissed me deeply, pushing for tongue and only yelping a little when I nipped the tip of it with my teeth.

“Happy new year!” Called the room, with several people watching us was we pulled back and smiled at one another.

I felt my phone vibrate in my clutch, and made a girly ‘excuse me’ gesture before pulling it out and checking it.

It was a message from my bank: “Transfer Complete.”

I closed my eyes for a moment and took a deep breath.

He doesn’t need to know how much you’re going to enjoy this, I reminded myself, working to keep the smile off my face as I put my phone away, took a step back….

And decked the shit-eating grin right off Buddy’s face.

-----

“You sure you’re sober enough to—”

“Yeah. Jeezus fuck, that hurt,” Buddy grumbled, only a little muffled by his swollen jaw. The butterfly bandages held the gash on his cheek closed, and I doubted it would even need stitches. I’d cleaned most of the blood off the ring, but I was sure the jeweler would have Questions when Buddy returned it. “Did you have to hit me so hard? I was expecting a slap or something but—”

“Hey, I’m not the slapping kinda girl. If you’re gonna hit someone, hit ‘em,” I said back, grinning as I waved to the parking attendant on our way out. “You wanted it to be realistic.”

“Yeah, but the screaming—”

“You are a cheating bastard, and you know it.”

“And the kicking—”

“I didn’t want to risk another punch with my nails, and you were on the floor.”

“The crying?”

“You saying you didn’t deserve it?” I gave Buddy a long look. He started to say something, but instead just rubbed his jaw and glared at me. “Thought so.”

“You really are a fuckin’ bitch, you know that?”

“Yeah, well.” I shrugged. “Club’s on Baker and Tenth. The Pink Kitten.”

“Cute,” he said, typing the name into his GPS. “Think I can—”

“No way in hell.”

“Fuck.”

“Go home and take care of that cut,” I told him. “And think about the stuff I yelled at you, too. I was serious about most of it.”

“Most of it?”

I gave him another long look.

“Yeah, yeah, alright. Whatever. Shit, that hurt.”

I laughed. “Yeah, but your mom looked awful pleased when I threw the ring at you, didn’t she?”

“Did she? I was too busy looking for my tooth to notice,” he said, though he was finally grinning a bit. “You know, we can still—”

“Buddy?”

“Yeah?”

“You finish that sentence, and you won’t finish this drive.”

“...Fair enough.”

We completed the rest of the ride to the club in mostly-companionable silence, save for the occasional groan of pain from Buddy when we would hit a pothole or dead policeman.

I climbed out of the car in the sexiest way I could, then leaned back in the door before closing it. “Hey, Bud.”

“Hmm?”

“Text me in the morning to let me know if it worked.”

Buddy nodded. “Will do, Reese. Will do. And, hey.”

“Yeah?”

“Happy new year.”

“You too.”

I closed the door and watched Buddy drive away.

“Hey Cindi,” I said to the bouncer as I walked up to the doors.

“Hey yerself, girl,” she said, checking me out only a little less hungrily than Buddy’s father had. “Late to the party, aren’t ya?”

“Had to work late.” I grinned and gave her a Franklin. “Get yer girl somethin’ nice, on me.”

Cindi whistled. “Will do. Lily’s at your usual table with the girls.”

“Thanks!”

The club was loud, but not too loud. At almost 1 in the morning things were starting to wind down, even for a New Year’s celebration, and it wasn’t hard to pick my way through the thoroughly sloshed crowd to our normal table in the back corner, away from the stage.

Lily almost launched herself out of her seat when she spotted me. “Reese! You made it!” She said, leaping up to wrap her arms around my neck and hang on. Not that I was spectacularly tall, even in my heels, but at five nothing I still towered over her. “How’d it go.”

“Oh, about as well as you’d expect,” I said, wrapping my hands around her waist and holding on. I gave her a quick kiss, then another, welcoming her tongue rather than snapping at it like I had Buddy’s.

After a few long moments she pulled back, still grinning. “You punch him like you said you were going to?”

“Yep.”

“And did he?”

“Nope.”

She grinned even more. “So that means—”

“Yep,” I agreed, lowering her to the ground. “You win.” I pulled the wad of bills out of my purse and handed it to her.

“Hehe! Toldja he wouldn’t hit a girl.”

“Yeah, well.” I shrugged, then looked over her shoulder. “Hey ladies, how’s it been?”

“Great!”

“Wunnerful!”

“I wassaboudda make my move!”

Everyone laughed at that: Gretchen had been threatening to steal Lily from me for months, but had yet to succeed.

I slid into the end of the booth, and Lily climbed into my lap, once again wrapping her arms around me.

“So, what’s this Buddy like?” Ellie, a tall red-headed friend of ours, asked from the other side of the table.

I laughed. “Arrogant. Misogynist. Rich. Handsome. You know the type,” I said, pulling a picture of him up on my phone with his cut cheek and swollen jaw.

I passed the picture to her, and she nodded. “About your height, ain’t he?”

“Yeah.”

“About… one seventy?”

“One sixty-eight,” I agreed. “Last I heard.”

She nodded again. “Nice legs?”

“Just what are you thinking, Ellie?” I asked, absolutely aware of what she was thinking.

“Nothin’!” She assured me, smirking. “Just that you wouldn’t be friends with him if you didn’t think he was redeemable, right?”

“Maybe.”

“So, the asshole rich boys usually make the best foot stools,” she said.

I shook my head. “I don’t know if he’s into that, hon.”

“Worth a shot, ain’t it?” She asked, winking. “Can I at least have his number?”

I thought about how Buddy had wanted into the club. Well, if Ellie has her way with him, he might just get his wish. “Sure.”

I cuddled with Lily as Ellie took Buddy’s number off my phone and texted him.

“So, any new year resolutions?” She asked me, nuzzling my ear.

“I think I’m gonna swear off guys, be a lesbian.” That got a round of laughs and cheers from the table at large.

“Mmmm,” Lily said, licking my ear lobe. “Me too.”

--END--

-----

NOTES:

Alright, so I managed to finish an entry for the contest! Yaaaay!

It's a little bit different from my typical kinda story, but I had the idea and wanted to run with it. If you wanna read a New Year's story that's a little more typically "me," then my FIRST idea will be going up on the Patreon as a short multi-part series called "False Start," starting sometime in the next few days :)

All comments and kudos appreciated, and I hope people liked the read!

Melanie E.