What Might Have Been

"They sure can talk when they get going can't they?" said the stranger in the same sort of rapid-fire friendly tone a car salesman would use.

"They can," agreed Kyle looking at the stranger with a frown.

"Sorry, I'm Paul Maturski," he said extending a hand.

Kyle took it looking more closely at the newcomer. He didn't appear to be wearing a badge.

"Kyle Flynn. You aren't class of 08'?"

"Oh! No," said Paul grinning.

"You're someone's spouse then?"

"Well, I soon will be..." said Paul without elaborating.

Kyle was just about to try to pin down the elusive stranger when Debbie reappeared.

"Paul, you're early."

"I know the moved up the charity auction by two hours...Sorry," he replied leaning over to kiss Debbie on the cheek.

Kyle froze in place looking from one to the other not sure what to say.

"I guess we need to go than I did promise to be there. It was good seeing you, Kyle, I'm sorry I have another commitment I can't get out of so we will have to catch up later. Maybe we can talk at the wedding if I'm not too bogged down. I will fetch my coat."

Debbie walked away leaving Kyle confused and still standing with Paul.

"You and Debbie?" he asked.

"Well, it's not public knowledge yet. She likes to keep things private, but I think the word will be getting around soon, Kevin."

"It's Kyle,"

"Right, well it was nice to meet you."

Paul walked off after Debbie's retreating form.

"Shit!" said Kyle feeling more than a little foolish. Here he was trying to pour his heart out to Debbie, and she was engaged to someone else.

"This is not how I saw this going," said Kyle under his breath.

The only dignified way to deal with the situation seemed to be having another drink, and that was exactly what Kyle did followed in rapid succession by three more. He soon found himself hanging onto the bar with one hand to keep his balance while trying to focus on the drink in front of him. This was the first time since college that he had managed to get well and truly drunk. He knew it would probably come back to haunt him in the morning but for now, it wasn't so bad.

A shoulder bumped his arm almost causing him to spill his drink. Kyle turned to offer an unkind comment on the manners of the person next to him, but she surprised him when she threw her arms around his neck before he could speak.

"Kyle Flynn! This is so cool! How are you?" she shouted in his ear.

He squinted in the semi-darkness to focus his slightly blurry eyes on the woman in front of him. It took a moment for the memory to come flooding back to him.

"No Pants!" he shouted.

The tall red-head frowned at him, "No one has called me that since high school. It was a very insulting nickname anyway, and so not true!"

Holly "No Pants" Vance had been the most heralded slut in the history of Alfred K. Merton High School. She had earned the nickname because supposedly she spent more time out of her pants than in them. Her exploits had been legendary back in the day including getting the ski club disbanded when she reportedly smuggled booze into the back of the bus on a trip to Brenner's Lodge and then gave Fred Harvey a blow job under a blanket. Fred had bragged to the whole school about it, and the school board had banned any further trips for the club.

"Sorry, Holly. You're right. I'm sure your reputation was greatly exaggerated," slurred Kyle.

"Damn right it was I never did half the shit they tried to pin on me."

"Except for streaking at the homecoming game," commented Kyle.

"That was a double dog dare I didn't have a choice!" she said laughing.

Kyle had to admit Holly still looked good. A brash red-head with fair skin and a face full of freckles she sported a very impressive pair of cantaloupe-sized funbags on her chest. Her thin lips were shiny with gloss and her well-toned legs stuck out of the bottom of her skin-tight dress that looked at least one size too small.

"What are you drinking," asked Kyle.

"Bourbon straight up," she said with a smile.

"Another one for the lady."

They toasted the class of 2008 clinking their glasses together.

The night had gotten away from Kyle after that point. He called for a cab realizing that he should probably be getting back to the hotel. This realization came when the bartender told him, "We got no more fucking liquor go home!"

Holly was kind enough to help him out to the curb to wait for his cab.

"You know maybe I should come with you? Help make sure you get into your room o.k," suggested Holly when the cab pulled up.

"Sure, I guess that would be a good idea," said Kyle trying with difficulty to manage the door handle.

The driver let them out in front of the hotel and Holly guided Kyle to his room where he fumbled with the key lock card to open the door. They eventually made it inside. Kyle tossed his key card on the dresser and turned to thank Holly for her assistance only to find her standing right behind him just inches away.

"Um...Thanks for the assist, Holly, I probably wouldn't have made it this fa...Mmphhhhhhh"

Kyle found it difficult to complete his sentence with Holly Vance's tongue in his mouth. He was so stunned and his reflexes so slowed by all the alcohol that he had imbibed that at first he hardly reacted, but slowly he slipped his arms around her slender waist and returned her kiss with more than a little booze enhanced enthusiasm. Holly put her arms around his neck as she slid her slick lips all over his twirling her tongue around inside his mouth. It had been nearly two years since the last time Kyle had enjoyed the company of a woman. His wife had frozen him out of bed the last year they had been together, and during the protracted run-up to his divorce he had been too busy and mentally taxed to think about dating. Still, at least a small part of his still functioning brain cells registered that maybe this wasn't the best idea in the world.

"MmmmmMmmm...Wait...Holly...Uh...I...don't know if this is such a great idea."

"How do you know for sure until you've tried it?" answered Holly with a wicked smile.

She had a point, or at least her logic seemed sound to someone who had just made a one-man run on an open bar.

While Kyle was still wrestling with the morality of what was happening Holly dropped to her knees and loosened his belt before removing his pants with practiced ease. His cock was only at half-mast at the moment, but Holly was more than confident in her ability to remedy that problem.

"Oh...shit..." groaned Kyle.

He looked down just a little stunned to see his penis in Holly's mouth, but he did nothing to correct the situation. Truth be told, her mouth felt really, really good. Holly's head moved up and down letting Kyle's rapidly swelling prick hit the back of her throat where she squeezed it tight. The length of his shaft quickly began to drip with Holly's spit, and she rubbed it with one hand spreading all that natural lube around. Kyle moaned louder sliding one hand into Holly's long red hair pushing her wet lips faster. He couldn't remember the last time a woman had given him a blow job, and Holly was proving to be one superb little cocksucker.

Holly pulled Kyle's cock free and started to lick it from the tip to the base of his shaft before she carefully sucked at his tight ball sack letting her tongue loll across the surging flesh. Her hand was a blur on his wet cock.

"Oh fuck!" shouted Kyle, all at once grabbing Holly by the wrists and pulling her back to her feet. He shoved her roughly up against the dresser kissing her hungrily driving his tongue deep into her mouth while his fingers struggled to come to grips with the catch on the back of her dress. The long zipper holding it in place came down a moment later, and as luck would have it, Holly had gone bra-less tonight, so her huge, round tits immediately spilled out into Kyle's face.

"Fuck, Vance, your tits are freaking huge!" he said before she forced his face right into one. They were quite a spectacular pair, big and pale with a few freckles sprinkled here and there. She sported a wide, bumpy pair of light pink areolas and nipples thicker than Kyle's pinky. He dove in sucking one of those fat nips right into his mouth and biting at it.

"Oh shit, Kyle! Ummm...Baby...Mommie likes that a lot!" cried Holly softly.

Kyle's head was like a pendulum swinging back and forth from one big flesh cannon to the other licking and nibbling the whole time. Holly's tits were soon gleaming with his spit her nipples rock hard and swollen from the insistent sucking. He swung her around toward the bed nearly ripping her panties getting them off after pushing her back onto the comforter. Her pussy was a mostly clean field except for a single racing stripe of red hair that ran down the middle of her Venus mound. The pink lips that guarded the entrance to her vagina were bright with her juice. Kyle wasted no time in getting his lips around them sucking at the loose skin before he plunged his tongue into the lighter pink flesh beyond.

"Oh...God! Kyle! Yes! OH YES! Eat my pussy baby! Eat Holly's pussy it's so lonely..."

He lapped away at her juicy insides taking her nectar all over his tongue. The tips of his fingers toyed with her pussy from beneath before he lifted his tongue to press it on her swollen clitoris. This sent Holly over the edge, and she gripped the comforter tightly humping at Kyle's mouth with her hips.

"FUCK! OH FUCK ME! Jesus...Kyle! That's my happy spot baby! Oh GOD YES! Shit! You're gonna make me cum if you keep that up!"

The sounds of Holly's loud moans of pleasure filled the small hotel room. Her desperation was written all over her face as Kyle pushed her closer to the orgasm that threatened to engulf her body. One hand slipped into the hair on the back of Kyle's head pushing his lips tighter to her clit. Her movements became more frantic until the inevitable happened and she creamed Kyle's face, loudly crying out while clenching his hair painfully in her grip.

"Motherfucker! Ah! Kyle! I'm cumming! OH GOD! Cumming so hardddddddddd!"

Holly's back arched into the air while her head was thrown backward by the sheer force of her orgasm. She remained like that for several seconds suspended, muscles straining, moaning in the back of her throat until she crashed back to the bed. The vibration of her body dropping to the blankets beneath her had barely rippled through the bed frame before Kyle was on top of her driven by his freed lust. Their mouths came together pressing tight, tongues darting back and forth.

"Hang on just a second, Baby," breathed Holly. She leaned over the side of the bed and fished a condom out of her purse pushing Kyle over onto his back while slipping it over his massive cock. The bed began to creak again as Holly guided Kyle's wrapped package into her slippery love hole.

"Ahhh! Fuck, Kyle! Ah! Uhhhh! Yesssss!"

Kyle was utterly lost in a haze of booze and crushed inhibitions. It had been so long since he had been inside a woman his body just seemed to soak up every sensation like a starved man sitting down to a five-course meal. He grunted animal-like pushing into her with deep, vicious thrusts of his hips his prick burying itself further into the moist heat of Holly's vagina. The pain of her dragging her long nails across his chest barely registered. The slapping of their skin was the only other sound in the room.

The alcohol prolonged the experience certainly, but the surging cum in Kyle's sack couldn't be contained forever, and it started to fight for release pouring up his shaft. His groans became more panicked, and his movements quickened. Holly's body was wracked by spasms heralding her own second cumming.

"Fuck...Fuck...FUCK! Ohhhh Shitttt!" cried Kyle suddenly.

"Kyle! Holy shit! Uhhhh..."

They came almost together with Holly falling just a step behind Kyle who emptied a seriously frightening amount of spunk into the condom gripping his cock stretching it to the limit while triggering her eruption as her pussy became a cream filled mess.

"Damn, Baby! I felt that jerking all the way up to my stomach. You would have made Holly's pussy all sloppy you bad boy!" said Holly laughing.

Kyle barely heard her as his eyes rolled back in his head.

The sun showed through the thick curtains of the hotel room the following morning one thin beam piercing the un-opened eye of Kyle Flynn annoying him just enough to crack open that very same eye immediately regretting the decision.

"Fuck me..." whispered Kyle rolling onto his back.

His head felt like it was clamped in a vise that a vindictive giant was cranking tight one turn at a time. It took him three tries to sit up, and he regretted the effort as soon as it was expended since it sent the room into a series of lurching spins that nearly made him empty his stomach on the rug. The events of the night before were a foggy memory that refused to coalesce for him until a particularly loud snore split the relative quiet. Kyle slowly turned his head to stare at the naked form of Holly Vance still sleeping face toward him on top of the comforter.

"Oh shit...What the fuck did I do last night," mumbled Kyle.

The room steadied a bit, and he rose to his feet taking a few tentative steps toward the bathroom. A splash or two of cold water from the sink helped to clear his head and slowly the events of the previous evening started to take shape in his mind. The awkward meeting with Debbie, finding out she was engaged to some motor-mouthed dweeb, and then a lot of drinking. The run-in with Holly was in there, but he struggled to recall exactly how they had ended up in his room. Things had gotten even crazier after that and he just vaguely was able to conjure up images of the two of them kissing and falling onto the bed.

"Wow, first sex I've had in forever, and I can't even remember it," said Kyle shaking his head at the horrifying image that stared back at him from the hotel bathroom mirror.

The ringing of his cell phone drew him back into the main room, and he struggled to fish the phone out of his pants pocket.

"Hello?"

"Kyle? Are you o.k.? You sound funny," said Jill's voice.

"Um...Yeah, I'm o.k. it was just...kind of a crazy night."

"Really? You sound hungover so I'm guessing it was a REALLY crazy night."

"Maybe a little too much..." said Kyle eying Holly on the bed.

"What's that mean?"

"Never mind, Jill. What can I do for you?"

"I was calling to remind you about the rehearsal this afternoon. Gary will be there to pick you up at two o'clock o.k.?"

"Right, I got it."

"I would find you some aspirin pronto, Big Brother. You sound like shit."

"Thanks for the advice kid. I'll see you at two."

Kyle hung up to spare himself any more of Jill's advice. He could only imagine the amount of crap she would be giving him if she knew he had spent the night with Holly Vance.

"Holly. Holly! HOLLY!" said Kyle shaking the sleeping woman and raising his voice when she refused to respond.

Her head finally snapped up, and she looked around with a confused expression on her face before her gaze finally settled on Kyle. A slow smile split her features.

"Hey, Lover...How are you this morning? Quite a night last night, huh? My legs are still shaking..."

"Yeah...It was some night," replied Kyle in a voice devoid of enthusiasm.

She placed a hand on Kyle's chest raising one reddish eyebrow, "Did you wake me for some more fun? I would totally be down for that..."

"Uh...Yeah, thanks for the offer, but I need to get ready to go to my sister's wedding rehearsal so not to be rude but I kind of need you to...Um...leave..."

If Holly was offended by Kyle's sudden dismissal, she didn't show it. In all likelihood, this wasn't the first time she had been summarily tossed from a man's bed following a night of drunken sex. She gathered her clothes from the floor and dressed herself stopping to hit the restroom before returning to fetch her purse. Kyle escorted her to the door where she stopped long enough to give him a quick peck on the lips which he begrudgingly accepted.

"I'll check in later. Maybe we could get some dinner tonight?"

Kyle merely grunted shutting the door.

"I should have my head examined. Holly Vance! What the hell was I thinking?" said Kyle to himself.

A shower helped restore some more of his pluck, and a few cups of coffee later he was starting to feel almost human when Gary showed up to take him to the rehearsal. The two of them rode mostly in silence since Kyle had reached over and turned down the radio as soon as he had gotten into the car.

"Jill said you were hurting this morning. I can see she didn't exaggerate," observed Gary.

"Things at the reunion may have gotten a bit out of hand."

"Did you see Debbie?"

"Oh, yeah, I saw Debbie alright..."

"I take it things didn't go exactly as you had hoped?"

"No. I might have been too optimistic on that score. There was more history to overcome there than I thought. Anyway, it doesn't matter she is with someone else. "

"Who would that be? I hadn't heard her mention a boyfriend."

"Not just a boyfriend. A fiancée`."

"Fiancée`? I can't believe she never mentioned anything about that during the time we've spent prepping Jill and I's wedding."

"Well, Debbie always was very private about her personal life. Maybe she didn't think it was important to mention."

"Maybe..." said Gary doubtfully.

The wedding venue that Gary and Jill had selected was at a vineyard owned by a local couple. They sometimes rented it out for parties and social occasions just like this one. It was a very romantic spot with the wedding set to take place on a small hill overlooking a gorgeous little garden with rows of cultivated grapes shooting off into the distance. Debbie was there when they arrived setting the scene and making sure everyone knew their place.

"Kyle, you and Jill will be at the house down the hill. When you hear the music start you will bring her straight up the hill following the trail, and stop right at this mark," Debbie instructed pointing at a spot on the ground just short of where a large wooden arch stood. The arch would be covered in flowers during the ceremony.

"Try not to trip over your feet," said Jill seriously.

"I am as graceful as a swan!" countered Kyle.

"Since when?"

"Could you two stop bickering and walk!" snapped Debbie in mock irritation.

The practice wedding went smoothly with Debbie doing an excellent job of keeping things flowing. Kyle spent much of his time trying not to stare wistfully at her while she went about her duties checking items off on a clipboard with a deft snap of her wrist. As things started to wind down, he found himself standing before the same wooden arch trying to picture what it would look like when Jill and Gary were standing beneath it in their wedding clothes.

"I know it looks a little stark right now, but tomorrow it will be perfect."

Debbie came up to stand next to him. The perfume she was wearing reminded him of the same scent she wore back in school. A smell that brought to mind fresh cut flowers and nights spent cuddling under blankets on his parent's couch watching the Saturday night Creature Feature on cable.

"I'm sure it will look wonderful. I wonder who you are going to get to do your wedding? Kind of like wondering where your doctor goes when they need medical advice."

"I imagine I have a long time before I need to worry about that," said Debbie with a laugh.

"You and Paul having a long engagement?"

"I beg your pardon? Me and Paul? Whatever gave you the idea we were getting married?"

Kyle froze for a long moment before turning to face Debbie who looked honestly puzzled by his comment.

"At the reunion last night he told me..." started Kyle.

"Son of a bitch!" said Debbie angrily, "I can't believe he did it again! After we just talked about it!"