The Double Date That Didn't End Ch. 05

CHAPTER 5 - The "What If" Fantasy

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RIA
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"What do you think they're talking about in there?" I asked.

Shane didn't even hear me. He was sitting on the bed, staring off into space. Still naked from his recent shower with Tracy. I paced around the bedroom like an anxious kitten, unconsciously nibbling away at my manicure.

Five minutes earlier, we'd all been groaning like wild animals, licking and sucking and kissing and coming one after the other in a haze of pleasure. We'd gone right up to the edge; done everything, except the ONE thing. The one thing that there'd be no way for us to un-do.

The one thing that, deep down, we all knew we wanted.

Five hours from now-if all went to plan-Shane and I would finally be living out our longtime fantasies by having sex with our incredible best friends. But, in the meantime, I was just about ready to pull my hair out from all the anxiety. And I really like my hair.

After all the excitement in the bathroom-Connor ejaculating all over my naked ass and Shane making a mess on Tracy's boobs-we'd retired to our separate rooms to dry and dress for dinner.

Shane finally noticed my frantic pacing.

"Are you okay?" he asked. "With everything that's happening, I mean."

"Why wouldn't I be?" My voice sounded distant. "Are you?"

"Yeah," he answered, but there was hesitation in it.

I blushed. "I just... I just wish I knew what everyone was thinking, you know? I REALLY want this to happen, but I'm kind of-sort of-just a little bit totally scared shitless that somebody or everybody is gonna get their hearts broken tonight. I mean, fuck! Seeing you in the shower with my best friend..."

"Well, what about you?" Shane frowned, his voice rising. "Connor was rubbing his cock all over you and you were getting off on it!"

"So were you! You and Tracy were standing there watching us, touching and kissing and-and-"

Shane gritted his teeth. I felt an odd tension in my stomach as he looked at me with those way-too-intense eyes of his.

"Are you mad at me?" I asked.

"No! Sweetie, no, of course not. It's nothing like that. I'm not mad at anyone-what happened just now was like a million fantasies coming true all at once. I wanted it just as badly as you did."

I let out a sigh of relief.

Shane continued: "I'm just... seeing red right now, I don't know how else to say it. I'm fine with the idea of you fucking Connor-really I am-I just didn't ever think that I would get so turned on from WATCHING it."

He groaned in frustration, and I couldn't help but notice the way his penis was already starting to recover, just minutes after Tracy's soapy tit-fuck had blown his mind. This situation was nothing if not confusing.

"I know what you mean," I said quietly.

Shane shook his head, laughing at himself, "It's crazy-what kind of guy gets aroused by watching his wife with another man?"

"Honey, we ALL got aroused by what we were seeing. I can't even tell you how hot it was watching you come all over Tracy like that."

"I know! And the look on your face when Connor was..." he trailed off. "I guess just wasn't expecting it to be quite so intense. In all honesty it did get me kind of angry seeing Connor mauling you like that."

"Oh."

"But in like a good way. 'Good angry,' if that makes any sense."

Shane sighed in frustration. Instead of saying anything, I knelt down between his legs, gently wrapped my fingers around his thickening shaft, and planted a long, loving kiss on the crown.

"Are you sure you still want to go through with this?" I asked. "All the way?"

"Absolutely," he sighed. "Tonight it finally happens. No more role playing. No more wondering 'what if.' Tonight I want you to fuck my best friend, just like you've always dreamed."

Then he rolled back his head and luxuriated in the feeling of my tongue stroking his cock back to life.

After a few minutes, I reluctantly took my mouth off of him and whispered, "I better stop. Tracy would never forgive me if I stole one of the orgasms you've been saving up for her all day."

"You're such a considerate friend," Shane laughed.

"I want you and her to enjoy yourselves to the fullest," I whispered. "Go wild."

Suddenly, we heard Connor and Tracy's footsteps approaching from the hallway. We quickly hopped into some casual clothes and opened the door to greet them.

"Hi," Tracy waved, nervous. She was dressed in a fuzzy white Christmas sweater, her hair up in a playful ponytail. Beside her, Connor had on his old faded bomber jacket and blue jeans.

Seeing the two of them standing outside our bedroom, I was struck with a sudden case of déjà vu, but I couldn't quite figure out why...

Then Shane solved it for me:

"Those are the same clothes you guys wore on our very first double date, three years ago."

Tracy blushed, "Remember how we were talking about 'what if,' earlier? Well, when me and Connor were getting dressed just now, we realized that, totally randomly, we'd both brought the clothes from our first date with you guys-funny coincidence, huh?"

Connor locked eyes with me: "And we got to thinking, what if it was like a sign or something? A sign that maybe tonight we could all finally give that big 'what if' the chance it deserves?"

A brief but heavy silence filled the space between us, then Connor asked, "Ria, would you go out with me?"

I blinked, "What?"

"On a date," he explains. "Just the two of us. Just for tonight. Like we were supposed to do, three years ago."

I gulped, feeling a sudden weight on my chest as I answered, "Yes, of course."

Connor looked past me, to Shane, and asked, "That okay with you, man?"

Shane nodded, visibly holding his breath.

Tracy slipped past me into the room and sidled up next to my husband, whispering:

"If you're not doing anything tonight, maybe we could hang out?"

Shane smirked at her. "Would this 'hanging out' involve, like, a date?" he asked.

"If you want it to."

"Are your friends Ria and Connor joining us?" he asked playfully.

"Not tonight," she whispered.

The two of them were momentarily lost in each other's eyes, and I felt a brief swell of jealousy rise up when Shane took her hand in his.

********

SHANE

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Tracy looked absolutely adorable as we strolled through town together. Bright, happy, glowing with excitement-clinging to my arm like she needed it to stay upright.

Dinner had been a bust. The only place in town we could find that was still open on Christmas Eve was an extremely shady-looking Chinese restaurant that practically screamed "food-poisoning." We didn't want to risk it.

Instead, we hit up a gas station for some Funyons, a bag of beef jerky, and two cups of "hot cocoa" that honestly tasted more like chalk than chocolate.

But, while our Christmas Eve feast wasn't exactly what we'd been hoping for, Tracy and I still had a pretty awesome time just enjoying one another's company. We'd been close friends for all these years, yet we rarely spent time outside of work together, just the two of us.

We turned down one of the bigger residential streets, grinning at the preposterous amount of effort each home had dedicated to their holiday decorations:

Gigantic, hand-painted reindeer polluted the rooftops. Byzantine tracks for miniature locomotives wound around enormous winter landscapes in someone's yard. Man-sized robot nutcrackers marched in circles around a small gazebo. And the LIGHTS! Let's just say their electric bills for the month of December must have reached into the quadruple digits.

"How much time do you think it takes to set all this stuff up every year?" Tracy laughed.

"Weeks, at least. Neighborhoods like this, I bet you it's like an arms race between all the men. Less about the embracing the holiday spirit and more about having the baddest motherfucking yard in town."

"Yeah, Freud would have a field day with these people." Tracy opened her eyes wide, pretending to be aroused by what she saw: "Oh, Jimmy! Your Christmas decorations are so... BIG!"

When she turned to face me, Tracy's bright blonde hair caught the colors of the blinking lights: green, red, gold...

"You are so beautiful," I sighed.

Tracy placed her cute wool mittens on either side of my head-holding me steady as she brought her lips to mine.

"But, there's no mistletoe," I joked.

"We don't need it."

Our kiss was a slow burn, going from warm and pleasant to hot and heavy-and when we finally broke apart there was a whimper in Tracy's voice.

"Do you think we'd still be together?" she asked.

"You and Connor?"

"No, I mean me and you. If things had plays out differently on that very first double date, way back when. Earlier today, you said you sometimes imagine a whole complicated fantasy version of your life, where you wound up with me instead of Ria. That whole 'What If' fantasy."

"Yeah," I blushed.

"What's it like?"

"My fantasy?"

"Yeah, the 'What If' fantasy. I want to know what you think a relationship with me would have been like. Are we madly in love? Are we married? Do we fuck like five times a day?"

I chuckled, "Oh, at LEAST that much."

She took my hand, a playful smile on her face. "I'm serious though. I want to know."

I took a deep breath, suddenly self-conscious about the whole situation. Not two hours earlier, I'd been grinding my cock against Tracy's sexy naked body in the shower-and now here I was, feeling inexplicably shy.

"Come on," she pushed. "We've been 'revealing' things to each other all day, haven't we?"

"Okay," I sighed. I took her mittened hand in my own and we strolled side-by-side through the neighborhood. Some off-key carolers crooned in the distance. Snow crunched beneath our boots. And Tracy listened intently as I regaled her with the entire story of what might have been.

My 'what if' fantasy:

"Go back in time. Three years ago, tonight. I pick you up around this same time-around eight-and we head to the carnival to meet your friend Ria and some guy named Connor. You're dressed in those exact same clothes, with that exact same lipstick."

"You remember the lipstick I was wearing?" Tracy asked.

I smiled, "I remember everything about that night. I remember being so nervous on the drive over to pick you up, that my hands were sweating. I remember being terrified that you'd notice that I'd screwed up shaving and one of my sideburns was a millimeter or so longer than the other. I remember the moment you sat down in the car beside me-happy as could be-and I thought, 'Man, I hit the jackpot. This girl IS Christmas. Bright green eyes and deep red lips. Cozy and jolly and sweet as dessert. Festive sweater, fuzzy mittens. A nice girl who definitely belongs on Santa's naughty list."

Tracy smirked at that last bit.

"Point is, I felt like the luckiest guy in the world that night."

"But you still chose to go home with Ria."

I shrugged. "In real life? Yeah. You and me-we weren't right for each other, Trace. That much was obvious from the moment I handed you a bouquet of flowers, and you reacted like I had just bought an engagement ring."

Tracy shrunk down a bit, embarrassed. "I just get nervous when boys do things like that. I didn't mean to be ungrateful."

"You didn't do anything wrong. Me and Ria had a connection. You and Connor had a connection. The rest is history. BUT-"

I gave her another quick kiss on the lips.

"But we're not talking about real life, here, are we?"

"Right."

"In my 'what if' fantasy, Ria and Connor don't even show up that first night. It's just you and me, having a blast, enjoying the carnival. Getting all snuggly as the night gets colder."

To illustrate my point, I wrapped an arm around Tracy's shoulders and pulled her in closer.

"And as we get closer to midnight; closer to Christmas, I'm already falling head-over-heels for you. Not the way I fell for Ria-both of us perfectly compatible and instantly connected and all that-no, when I fall for you it's the complete opposite. It's wild, like jumping off a cliff because I can't stand the thought of standing on solid ground anymore."

She blushed.

"And then midnight finally rolls around and we decide to take a ride on the tunnel of love."

I lowered my voice, so that the passing carolers couldn't hear as I whispered:

"And as soon as that stupid swan boat starts moving, we've got our hands all over each other. You hop up on my lap and we start kissing, I start copping a feel beneath that sweater you've got on..."

I trailed off, pausing to take an appreciative glance at the way Tracy's luscious chest was straining against her Christmas sweater.

"Do we have sex in the tunnel?"

"No way," I laughed. "Way too cold and uncomfortable for a fantasy. No, we go straight back my car and we fuck in the parking lot."

"With the heater on full blast," she giggled.

"Of course, can't have us catching a hypothetical cold. Anyway, you hop up on my lap, and somehow we manage to struggle out of all our clothes-"

"And then I rub my wet panties all over your face."

I blinked, caught off-guard by her comment.

"Just trying to contribute," Tracy grinned wickedly.

"Oh, don't stop on my account."

"No, this is your story. I just wanted to throw that in there."

"Hey, by all means. You can throw your panties around any time you please, I won't complain."

"Anyway-"

"Anyway, back to the story: We're both buck naked, rubbing up against each other and fogging up the windows. I recline the driver's seat and lay down, and then I roll you over so those gorgeous big tits of yours are pointing up at the ceiling for me to fondle and play with."

Tracy pointedly stuck out her chest towards me. "You mean these tits?"

I started talking faster:

"My cock is sticking straight up between your legs, pressing against the length of your slit."

"Ooh, I like where this is going.'"

"You're so fucking hot and so fucking wet-and your body is just drooling honey all over me. Before long, you've lubed up my cock so much that your body literally can't keep me out anymore-and every inch I've got to offer slips slowly up inside of you."

Tracy shivered, enjoying the mental image. I circled around behind her-my arms still tightly hugging the girl's curvy body.

"Then what happens?" she whispered.

"Then we fuck as hard as we can, as fast as we can, and you come like fifty times before I pull out and blow my load all over your stomach."

As I spoke, I gave her both of her breasts a good firm squeeze.

"I think I'm gonna like this story," she panted. "Tell me more."

I playfully nipped at her ear. "Maybe I should tell you in the car."

********

RIA

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"But it's closed," Connor frowned, staring up at the dark, abandoned ice rink on the outskirts of town.

"So what? Let's sneak in. It'll be fun!"

"Sneak in?" he looked uncertain.

"What, you can't break the rules anymore now that you're a cop?"

"It's not that..."

"Good, because I plan on breaking a lot of rules with you later tonight."

He grinned.

"I can't ice skate," he laughed.

"Really? Mister 'Varsity-letterman-every-sport-known-to-man' can't skate?"

"Never even tried."

I took his hand in mine. "Me neither."

Sneaking into the rink wasn't too tough. It was outdoors and there was nobody around, so all we really had to do was climb over a little fence. Actually getting to the ice skates however, was a different story. They were locked up inside a cage, but Connor did a trick with one of my hairpins and managed to get it open.

"Where did you learn to do that?" I asked.

"When I was a teenager I was kind of a piece of shit," he answered.

I laughed, feigning outrage. "You're telling me that my hunky policeman best friend has a secret criminal past?"

"Technically, yes. Though I wouldn't call my teenage self a 'criminal' so much as an 'obnoxious little twat.'"

"Fascinating. You were the Judd Nelson type, then?"

"Pshh, I wish. How about you? You I bet you were like a Latina Molly Ringwald. Queen bee cheerleading captain and all that."

"I was more of a Michael Hall, actually. Four straight years of four-point-ohs, motherfucker!"

"No way."

"Oh yeah. Nerd-queen late bloomer. Guys didn't even realize I had tits until I started working at Hooters in college. Tracy gave me a pretty serious makeover, god bless her."

"No cheerleading then?"

"'Fraid not."

"Damn!" he cursed. "So much for my million zillion fantasies of you in a pleated miniskirt waving your pompoms."

"Hey, play your cards right and next Halloween I'll dress up as a cheerleader. A slutty cheerleader."

Connor handed me a pair of skates in my size and we tiptoed out onto the ice rink-stumbling and staggering like a couple of toddlers learning to walk. Connor held onto the wall, I held onto Connor, and together we made a few awkward laps around the circumference.

"Okay, what do you say next time we really go for it?" Connor asked. "All the way around the rink, no holding onto the wall. First one across the finish line wins."

"Wins what?" I asked.

"Respect?"

"Lame. How about the loser has to do something. Like a dare. Anything the winner wants, no chickening out."

"Oh, you're gonna regret saying that," he teased.

"You're assuming one of us actually makes it all the way around without slipping on the ice and shattering our pelvis."

Laughing, he and I took exaggerated starting positions for our little race, trying our best not to fall over before we'd even begun.

"Ready?" Connor asked.

"Set!" I answered.

"Go!" we both shouted together, and took off as fast as we could go-

Which for me was probably about two miles per hour, if you factored in all the stumbling and slipping.

Connor got a huge lead early on, but he built up so much momentum around the first turn that-

"Whoa!!"

-He lost control and hit the wall like a cannonball, cracking the wood on impact.

"Connor!"

He lay motionless on his back. I hobbled across the ice towards him with all the speed I could muster-

Then I tripped over my own dumb feet and landed knee-first on his crotch.

"Jesus Christ!" he groaned, immediately pushing me aside.

"I'm so sorry, I-"

"Breaking and entering, crashing into a wall, kneed in the balls... This is turning out to be about the sexiest date ever, isn't it?" Connor joked.

I was just glad that he was okay. Our laughter fogged up the cold night air all around us.

With Connor still lying down on the ice, I crawled on top of him and tenderly kissed his forehead.

"You're okay?"

"Yeah, I'm okay. The wall got it worse than I did." He squeezed his muscular arms around me, holding my body to his. Face to face, our lips were close enough to touch. "Looks like I lost the race, though. I'm gonna go ahead and say me falling on my ass constitutes a forfeit."

I mussed up his short-cropped hair. "Meaning you have to do anything I tell you to."

"That was the deal. What do you want from me?" Connor asked, his hands gently squeezing at my buttocks.

"You'll see, soon enough," I whispered.

We kissed, and beneath me I felt Connor harden through his jeans.

********

SHANE

********

Tracy's fingers teased their way down my zipper, finally freeing my cock to the chilly night air. She wasted no time, immediately gripping my naked shaft between her fingers and pumping me to full hardness.

Then she dropped her mouth down to my lap and-and-

"Ohhh..." I moaned.

Tracy took her lips off my cock just long enough to whisper, "Keep telling the story."

We'd been making out in my car for god knows how long. Our passionate bouts of kissing and groping were periodically interrupted by me recounting for Tracy the many, MANY fantasies I'd had of her over the years.