The Double Date That Didn't End Ch. 01-02

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Dance with the one that brung ya’. Or don't. Or both.
18.7k words
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Part 1 of the 6 part series

Updated 10/23/2022
Created 12/08/2013
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bosombuddies
bosombuddies
4,628 Followers

(This is an entry in the "Winter Holidays" Contest for 2013. Just a heads-up: though this submission stands on its own as a complete story for purposes of the contest, I will be posting an additional follow-up story with these characters in the relatively near future. In the meantime, please enjoy!)

CHAPTER 1 -- Dance With the One That Brung Ya'

********

SHANE

********

Most of my coworkers spent the day grumbling about the fact that they all had to come into the office on Christmas Eve. Everyone was so distracted by thoughts of hearty family dinners, mysterious pretty boxes, and little pine trees wrapped up with blinking lights, that hardly any work got done all day. But working on Christmas had never really bothered me. My parents had passed away a few years earlier, I had no siblings or extended family to speak of, and I'd never been particularly a religious sort of fellow in the first place. As far as I was concerned, I wasn't missing anything by putting in a few extra hours at the office.

Problem was, I wasn't concentrating on my work, either. Not because of the Christmas spirit, but because of the new girl sitting at the cubicle beside mine, her gorgeous figure a constant fixture in my peripheral vision.

To use the parlance of my ancestors, Tracy was a "honey." Sandy brown hair, enormous green eyes, and a playful, girl-next-door smile that conjured images of Homecoming dances and first kisses at summer camp. Her disproportionately large breasts—currently filling out a festive holiday sweater—were so spectacular that I imagined they would jump-start the puberty process for every boy lucky enough to catch a glimpse of her in profile. No doubt she'd broken a lot of hearts growing up.

I glanced back at my computer and let out an audible laugh when I realized just how pathetically little work I'd managed to get done.

"What's so funny?" Tracy asked, peeking into my cubicle.

"Nothing, I'm just having trouble keeping myself on-task today."

"Too excited about the holidays?"

I shrugged. People always acted weird when I told them I didn't celebrate Christmas. Like it meant I had some personal vendetta against all joy, everywhere in the world. When a young, single guy with no living family doesn't celebrate Thanksgiving, nobody bats an eye. But Christmas? What sort of monster doesn't like Christmas?!

Over the years, I'd basically mastered the art of the non-answer to such questions:

"Actually, I generally like keep things pretty low-key. How about you?"

"No plans," she said a bit dejectedly.

That caught me by surprise.

"Really?"

"I usually spend it with my brother, but he's deployed overseas this year, and my best friend is gonna be busy hanging out with this new guy she's dating, so—yeah, no plans."

"No way, that's awesome!" I said. Tracy raised an eyebrow at my callous enthusiasm, so I hurriedly clarified: "Not the fact that you don't have plans—that's not what's awesome. I mean, it's awesome for me. Or, I mean, it could be."

Fuck. It'd been years since I'd gotten this tongue-tied over a pretty girl. I made a goofy, self-deprecating face, and tried one last time:

"What I'm TRYING to say is—"

"Trying and failing," she teased.

"—Is that I don't have any Christmas plans, either. So, if you're not doing anything, maybe we can hang out."

"Ah, I see," she flashed me a coy smile. "Would this 'hanging out' you describe involve, like, a date of some kind?"

"Sure, if that's what you want."

She tapped her pencil thoughtfully on her knee, considering my offer while her eyes gave me the once-over. I held my breath, wondering what she thought of me. My appearance has always been kind of polarizing when it comes to the opposite sex. To half the women in the world, I'm invisible. The "nice guy." "Not bad." A "teddy bear."

To the other half, I apparently look like a movie star. I provoke sighs of longing, secret love letters, and doodles in diaries surrounded by dozens of hearts.

Doesn't make sense to me, either. I guess it's like how cilantro tastes like soap to some people. I just hoped Tracy didn't see Teddy Ruxpin when she looked at me.

"Tell you what," She said, at last. "Remember how I said my friend is gonna be busy hanging out with some guy? Well, she invited me to tag along, but I didn't want to be a third wheel."

"I see. But if you show up with me..."

"Exactly, then it's not awkward. How would you feel about doing, like, a double date thing with the two of them? My friend Ria is awesome, and this guy Connor she met is supposedly pretty cool, too."

"Hey, a double date sounds good to me. Long as the word 'date' is in there somewhere."

"Great!" she chirped. "You can pick me up at seven."

Glowing inside, I turned back to my desk and spent the next hour utterly failing to get any work done. Maybe I was gonna have a Merry Christmas, after all. How many times do you get to go out with a girl like Tracy?

********

RIA

********

How many times do you get to go out with a stud like Connor? I mean, seriously, he's just so damn yummy, head to toe. Those eyes, those dimples, muscles on muscles on muscles... I'd been horny pretty much non-stop since he asked me out last week. And now, with less than an hour to go before our date—

Where the fuck was my straightening iron?! Seriously, I always kept it in the same spot, and it had no business abandoning me in my moment of need.

Aargh!

I plopped onto the bed—deep breath—calm down, Ria. I'd remember where I put it if I could just stop thinking about Connor's big strong arms for like two seconds.

Overnight bag! Yes, from last weekend!

Victorious, I ironed the frizz out of my long, dark hair—damn you, winter climate—and put the finishing touches on my appearance:

Hair? Check. Killer eye-shadow? Check. Badass leather jacket? Check. Sexy new bra and underwear? Double-check. I typically didn't give it up on a first date, but a girl can never be too prepared.

The doorbell rang and I did an excited little dance on my way downstairs.

As I passed by the family photo on the wall, I said a quick Christmas prayer for Mama and Papa in heaven. I may be a middling/poor Catholic—not sure I believe any of it, anymore—but there are some things about the way I was brought up that still feel right, regardless.

"Wish me luck, guys," I said.

Then I opened the door and smiled at the scrumptious stud-muffin standing on my front porch.

I admit, I was a bit let down to see how casually Connor had dressed for our date—blue jeans and a faded bomber jacket—and he hadn't brought me flowers or anything (sue me, I'm old-fashioned). Still, he was definitely the sexiest man I'd ever laid eyes on, and my mind was already racing ahead to what we might be getting up to later on in the evening.

"Hey there, handsome!" I beamed.

"Hey Ria! You look... very, very hot." His eyes were already going everywhere, checking me out.

That horny voice in the back of my head suggested skipping our plans altogether and just inviting Connor up to my bedroom right then and there—but I really did want the chance to get to know him better first, and I'd already promised Tracy that we'd make it a double date with her and some supposedly "gorgeous" guy named Shane she'd met at work.

Plus, who can say no to cotton candy?

The four of us arranged to meet up at a big holiday-themed carnival that had been set up in the center of town. Bright lights, fried food, and a menagerie of those whirl-a-puke roller coaster things. It was a bit chilly to be outside, but I figured I could always warm myself by snuggling up against Connor.

"Ria!"

I spun to see Tracy running towards me through the crowd, drawing everyone's attention with the way her porno-sized boobs bounced around beneath her sweater. I loved that girl to death, but damn if she didn't know what a spectacle she made when she did that.

She wrapped me up in a big, friendly hug, and then—

Her eyes glazed over when she saw Connor. Not that I could blame her, exactly, but if you ask me she was looking at him a little harder than she really needed to. And Connor was checking HER out a little more than he needed to, as well. Not that I could really blame him, either. I've got a pretty decent set of curves, but my bra-size doesn't register nearly as far up into the alphabet as Tracy's does.

Still, those two could have at least been subtle about it. You dance with the one that brung ya', right?

"Ahem," I said, breaking the spell. "Trace, where's YOUR date?"

"Huh? Oh right! Shane. I ran ahead when I saw you. He's right back there."

Typical Tracy, ditching her date five seconds into the evening. The girl was a total sweetie, but she could be so clueless sometimes. I followed her gaze to discover a very average-looking guy hurrying to join us. This was her "gorgeous" man from the office? Average height, average build—really the only thing special at all about him was the color of his eyes. They were a sparkling blue-green, like the abalone necklace my mom used to wear when I was a kid.

Fine, maybe he was a bit better than average-looking, I don't know. But definitely not as sexy as Tracy had described him over the phone. Not like my Connor.

"Nice to meet you," he said. His smile was sweet and earnest, a far cry from the playful smirk Connor always wore.

Shane turned his attention back to Tracy and said, "Here, some guy was selling these over by the hotdog stand. Merry Christmas."

To my chagrin, he handed her a bouquet of flowers.

********

SHANE

********

I'd gotten a little miffed that Tracy had just bolted ahead of me through the crowd like that, and then a little more miffed when I'd finally spotted her making goo-goo eyes at her friend's date, and then a little MORE miffed when I'd realized said guy looked like exactly the sort of bloke who used to throw me in the dumpster every day in the 7th grade.

But, thankfully, I realized I was being stupid. I hadn't even met these people yet, and I was already talking myself into having another downer of a Christmas. Well, not this year! This year I was going to have some fun, maybe make a few friends, and, if Santa Clause was feeling a bit generous later tonight, even go home with Tracy.

Once we'd all broken the ice by surviving a ride on the Tilt-O-Tron, the four of us actually hit it off amazingly well. It helped that we all had one big thing in common: none of us had anyone to share the holidays with. Ria and I had both lost our parents, Connor wasn't on speaking terms with his family, and Tracy's was overseas.

"So then, you guys know what it's like!" Connor laughed. "To tell someone you're not celebrating Christmas and watch them freak out. Like, they're worried you're gonna go door to door and tear down all the mistletoe or something."

It hadn't been fair of me to dismiss Connor as a "dumb jock" the way I had at first. Despite our differences (he was an amateur kick-boxer who played fantasy football, I was an aspiring painter who played World of Warcraft), we got along like we'd been friends for years. We didn't see eye-to-eye on much of anything, but sometimes a buddy you can have a good-natured argument with is more fun than a buddy whose brain works the exact same way yours does. Even if the girls hadn't been there, I probably would have still had a fun evening, just hanging with Connor.

But, although my first impression of Connor had proven incorrect, my first impression of Tracy's friend Maria (or "Ria," as she liked to be called), was irrefutable: the girl was a knockout. Short, slender, and sultry. Deep, dark eyes and bronze Latin skin. Tiny waist, terrific butt, and perky, perfect tits. She probably could have been a model, if she wasn't five feet tall.

Ria was every bit as sexy as my own date, but while Tracy's impossible curves looked almost like an exaggeration, Ria looked more "real." She acted more real, too. Fun as Tracy was to talk to, she had her head in the clouds half the time. That girlish energy was cute, but it was also hard for me to really connect with. Ria, on the other hand, was down to earth and just plain cool. She always looked you right in the eye during a conversation.

"How long have you two girls been friends for?" I asked.

They exchanged a quick glance, and then Ria answered, "It's gotta be seven years now. Back in college, we used to waitress for the same restaurant."

"Which restaurant?" Connor asked.

Ria shrugged, "Just some tacky sports bar."

Tracy was biting her lip, clearly fighting the urge to say more. I spun to my date, looked into her gorgeous green eyes, and asked, "Okay, what isn't she telling us?"

"Nothing!" she giggled.

"'Nothing' my ass. Come on, what's the big deal?"

"It was a Hooters!" Tracy blurted out, grinning wickedly.

I blinked. For at least a minute, all I could think about was how insanely fucking hot Ria and Tracy must have looked wearing those skin-tight Hooters uniforms over their young, voluptuous bodies: That white tank-top stretched to the limit over Tracy's phenomenal breasts. Those bright orange short-shorts hugging up against the cheeks of Ria's firm, squeezable butt.

Their tip money must have been off the charts.

"Wish I could have been a customer," Connor teased.

Ria blushed, giving Tracy the evil eye for telling us.

"Oh whatever!" Tracy chirped. "We were nineteen years old and it was an adventure. I've got no regrets."

But Ria was clearly embarrassed, and I felt bad for bringing up. So, before Connor and Tracy could utter another wise crack, I changed the subject:

"Who's up for another ride on one of these haphazardly-assembled Carnie death traps?"

While the Tracy and Connor started arguing over which ride looked the most dangerous, Ria turned in my direction and mouthed a silent "thank you." Warmth flooded though my chest.

It was an odd moment for me. Ever since that afternoon, Tracy had been all I could think about. I'd been fantasizing non-stop about where our date tonight might lead—imagining my first glimpse of her incredible, nude body—or the sweet expression on her wholesome face as she devoured the length of my cock—or the way she would moan while I grabbed onto her big, swinging tits and fucked her doggy-style on my bed.

And yet, as the night wore on, I found myself thinking more and more about her friend, instead. After a few hours, Tracy's incredible body seemed somehow less important than Ria's incredible smile.

"She's stunning, isn't she?" Tracy whispered in my ear.

"Huh?"

"Ria. You keep staring at her."

"Oh! Uh, yeah, she's pretty. I guess."

My date gave me a knowing grin and I kicked myself for being so classless. Here I was, lucky enough to be on a date with a fun, sexy girl like Tracy, and I couldn't stop thinking about her friend. What the hell was wrong with me? It's not like Ria was interested in me; she had her own man to fawn over. A guy who made me look like Jimmy Olsen, in comparison.

By ten o'clock, most of the families with small children had left the carnival to head home. I watched a family of three walk past us—two blissful but exhausted parents carrying their tuckered-out eight-year old. To your average person, it was an adorable sight. Just another Hallmark moment. But to me—

"It sucks, doesn't it?" Ria asked.

She was watching the all-too-happy family, as well.

"I used to think their birthdays would be the worst," Ria continued, "but on Christmas—"

I nodded, "On Christmas, you can't get away from it. Everywhere you look, it's 'FAMILY, FAMILY, FAMILY,' in bright fucking lights."

The all-too-familiar twisting stomach pain I always got when I thought about my parents' deaths reared its ugly head. I looked back over at Ria and asked, "Were you close to them?"

"Puerto Rican parents with only one child? Oh yeah. You?"

"Not so much."

Her eyes met mine. "You think that made it easier?"

"Maybe. But it kills me to think I didn't take advantage of the time I had with them."

Ria looked away into space, considering my words for a moment, then sidled back over to Connor, who was so busy arranging the condiments on his nachos that he hadn't heard a word we'd said. I was happy to let the matter drop, not wanting to spoil the fun of our double date with any more unwelcome memories.

For the next hour, the disparity between Connor and myself became even more evident as we playfully competed in a succession of silly carnival games. Connor could kick my ass at anything sports-related (like fast-balling a stack of leaden milk bottles) whereas I proved triumphant at everything requiring delicacy (pub-darting a brightly colored balloon).

At the start of the games, things went pretty much as you'd expect, with our respective dates rooting for each of us appropriately. But when Connor stripped off his bomber jacket to swing a rubber mallet at the High Striker, Tracy let out a wolf-whistle:

"Whoo! Come on, Connor!"

"Hey!" Ria let out a cry of mock indignation. "You don't get to cheer for my date!"

"I wasn't cheering for him, I was cheering for his arms."

I let it slide. After all, my eyes had spent a good chunk of the night focused on Ria.

When we moved onto the next event—bouncing ping pong balls into jars of water—Ria got her revenge by cheering for me instead of Connor. With years of beer pong experience under my belt, I easily defeated my much larger opponent, and figured it was only fair to give Ria the prize:

"Alright!" She pumped her fist in victory. "A half-dead baby goldfish in a bag. Just what I always wanted!"

We named our goldfish "Pete."

From that moment on, the wires were crossed for our little group. Tracy cheered Connor, and Ria cheered me. By the time our money ran out, the girls had literally switched sides, and I got very comfortable with Ria hanging onto my arm. Each time I won, she'd reward me with a hug, pressing her soft, sexy little body up against me. We were all just being silly, of course, but I secretly really enjoyed all the attention I was getting from Tracy's beautiful friend. Even if it was only pretend.

Finally, with more tacky stuffed animals than we could reasonably carry around the carnival, Connor and I briefly left the girls behind while we went to stash the prizes in our cars.

"Holy shit," he whispered to me, once we were out of earshot of the girls. "Those ladies are gorgeous."

"No kidding. You're a lucky guy, Connor. Ria seems really cool."

"Oh, she's amazing," he agreed. "Stopping by her office is the best part of my week. But—"

"But what?"

"Listen, I know I'm a dick for saying this, but Tracy is just so much fun. And SO hot."

I stopped at my car, depositing all the carnival prizes in my trunk. I tried to sound casual as I asked:

"Are you saying Tracy's more your type?"

"No! I don't know. I'm just saying it'd be pretty horrible to have to choose between the two of them, wouldn't it?"

I nodded in agreement, and Connor quietly asked, "Why, are you more interested in Ria?"

A voice in my head screamed "YES," but I wasn't sure I believed it. I really, really liked Ria. That much I knew for sure. It even felt like there was already some kind of connection between us, though we'd only just met a few hours ago. She was genuine and intriguing and relatable—and beautiful enough to write songs about.

But I dreaded to think that I might be turning down an opportunity for some hot, sweaty holiday sex with Tracy.

"I don't know," I said at last. "But it doesn't matter. I doubt either of those girls would appreciate it if we told them we wanted to switch dates at the last second."

********

RIA

********

Tracy looked fit to burst. After all our years of friendship, I'd learned how to spot the signs when she got too horny for her own good—and right now she was bordering on manic. Something told me Shane was going to be a very lucky boy indeed come Christmas morning.

bosombuddies
bosombuddies
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