Accidental Double Date

Story by draconicon on SoFurry

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A little story done for finalmagic on FA. A wolf has been cheating on two girls, and they find out when he accidentally invites them to the same dinner. Chaos ensues.


Candles lit, food laid out...incense burning to set the mood...Check, check, check.

Gregg smiled to himself as he shook the match, putting out the fire. "Heh, after a night like this, Pepper is going to be eager that I bet we won't even make it to the bed," the wolf said with a little chuckle.

At least, he was pretty sure that it would be Pepper tonight; it could be Track, instead. He knew he'd invited one of them to dinner tonight, but whether it would be the tigress or the raccoon was something he couldn't quite bring to mind. It didn't really matter, though; both of them were the definition of a fun time, though he could never pick just one of them.

He looked up at the clock on the wall. It wouldn't be much longer before they arrived, that was for sure; whoever was coming was probably in the parking lot right now, if not coming up the stairs to his apartment. Just enough time to get the flowers, he thought to himself.

Walking into the kitchen and pulling the bouquet out of the water, he shook the stems dry before walking over to the front door. Gregg waited, hearing the footsteps coming along the hallway, and smiled to himself. "Tonight's gonna be great," he muttered to himself. Oh, everyone had told him that there was no way that he could keep having fun with more than one girl at a time, but he'd proven them all wrong. He was juggling Pepper and Track just fine. So long as they never met each other, he'd be set for fun for the rest of his life.

Knock knock, on the door. He smiled, reaching down and pulling it open -

And was met with two sets of very familiar breasts, and two sets of very angry eyes.

He paled as the tigress and raccoon looked him in the eyes, their hands on their hips as they stepped through the doorway. They ignored the flowers in his hands, and Gregg started to curse rapidly in his head. They'd found each other, and judging by the fact that they were both here, they had compared notes.

They weren't happy, either, as they glared at him when he started opening his mouth. "Don't talk," Track, the raccoon, said. She pointed towards the couch. "Sit. Now."

Seeing no point in going against that, Gregg sat himself down on the couch, pulling his tail around and holding it over his lap.

Both females looked down at him angrily, but surprisingly, they looked at each other almost as angrily. Whenever one of the females looked at the other, her eyes were full of venom, like she would like to do nothing more than rip the other woman limb from limb. Gregg would have thought that they would be angrier at him than at each other; maybe there was some hope here after all.

Pepper, a tigress, looked at him. "Gregg, I was coming here for our date tonight -

"You mean his and my date tonight," Track interrupted.

"Whatever." Pepper shook her head. "We were both coming here for our date tonight, and we ran into each other on the elevator. When we both started coming to your door, we started talking. Apparently, we were both invited up here for dinner with you. Something that you've been doing for a while, from what Track tells me," she said.

It was all that Gregg could do to keep from slumping down, his face in his hands. As it was, he couldn't stop himself from wincing. How could he have been so stupid as to invite them both up on the same night? He'd been sure that he'd kept them coming on separate nights. This was such a basic mistake.

They continued, Track taking the lead. "So, we started talking even more. It looks like you've been trying to get what every guy wants; unlimited pussy with as many partners as you can get. Am I close?"

Gregg nodded slowly.

"I thought so. Well, you're going to have to choose," Track said, putting her hands on her hips. "You're going to have to choose one of us."

"But -" Pepper spoke up before he could say anything. "We're going to make it a little easier for you to choose."

The confusion on his face must have been pretty funny, considering how they both started grinning after Pepper said that. They leaned forward, just enough for it to look like their big breasts were going to slide right out of their shirts. Despite himself, Gregg felt a little reaction growing in his pants from the sight of the lovely breasts, but he did his best not to stare.

That best wasn't very good, of course, and they both laughed. Standing up straight again, Pepper said, "We're going to have a quick sex contest. Whoever does better with getting you off, gets to keep you. The other one goes off and never comes back again. That's the deal that Track and I have made."

He looked back and forth between the raccoon and tigress. They looked absolutely serious about the deal, but he still could hardly believe it. A sex contest? A sex contest with him being the one that chose the winner? That seemed almost too good to be true; it was something that guys fantasized about, not something that would actually happen to anybody, particularly not someone that was cheating on both people at the same time.

His eyes went wide as both of the females pulled off their clothes, and his bulge in his pants got bigger as they took off piece after piece of clothing. Neither wore all that much, really; no jewelry needed to be taken off, and nothing more complicated than a button needed to be undone. Shirt, bras, pants, socks, underwear all went flying to all corners of the room, leaving Pepper and Track completely naked before him. Gregg stared, his eyes wide and his cock throbbing hard in his pants.

Track stepped forward first, smirking back at the tigress. "I'm going to go first. I know just what he likes, so after you see how fast he cums with me, you can bow out with a little grace, you little slut," the raccoon said.

Gregg could only watch as she fell to her knees in front of him, unzipping his pants and yanking them off. He almost went backwards from the tug; Track was very strong from all the training she did, and it showed when she decided to be the one in charge, getting rough with him. She was fast, too, as he had no clue where she'd thrown his pants or when she'd gone back for his underwear, as both were gone, out of sight.

The naked raccoon knelt between his legs, her tits laying against his balls, and he could see that her nipples were erect. Felt it too, for that matter; they pressed against his balls like little fingers, and he shuddered softly. "Titjob?" he asked, a little grin growing on his muzzle despite the situation.

"Titjob," Track said with a nod. "Got some oil or lube or something?"

He nodded rapidly, reaching over to a stand by the side of the couch. After rifling through the drawer for a few seconds, he pulled out a bottle of slick lube. She didn't give him the chance to offer it, though; instead, she yanked it right out of his hands, and started covering her breasts with a liberal amount of the slick stuff. The fur flattened out and shone as she rubbed it in, rubbing her huge breasts together to spread it over them. The whole while, she looked up at him, grinning slightly at the way he stared.

When they were shiny enough to reflect the light from the lamps, she tossed the lube back to him. "Heh, that better be enough, big guy," Track said. "Now, why don't you put that cock of yours between my tits, and we'll see how fast I can get you off, huh?"

No guy could have resisted that offer, let alone someone that knew how good Track was with her tits. Grabbing his cock at the base, Gregg scooted forward on the couch cushion, pushing his cock between those massive, slick globes, and groaned softly at the way that his cock slid against the slick curves.

Track immediately pushed her breasts together from the sides, increasing the pressure around his cock. The raccoon dragged herself up and down his cock, her breasts slapping wetly against his crotch every time she slid back down, and her mouth was open slightly, allowing just the very tip of his cock into her mouth. Gregg would have tried to get more in there, but her breasts were so big that they swallowed his cock utterly, keeping it from getting up to her mouth the way that he might have been able to do with a girl with smaller breasts.

But despite not being able to get any oral stimulation from her, the fact that she could swallow his whole cock with her breasts was more than enough to make up for it. They were huge and smooth, gliding along his cock with the aid of all the lube that she'd put over them. It was hot and slick, almost like a smooth pussy, but much more cushion-y. He groaned softly, leaning his head back as she lifted and lowered herself along his cock, teasing him and pushing him along towards his climax quickly.

Suddenly, she changed things up. Rather than bouncing up and down, she started to sway from side to side, slapping his cock between her tits, bouncing it back and forth. Then she went back to going up and down again. She swiveled a bit now, though, turning herself from side to side as she went up and down, adding a spiraling feeling to the feeling of penetrating between her breasts.

"Come on, big guy, come all over my tits...all over my face," Track muttered up at him, her tail swaying behind her as she squeezed her breasts around his cock again. "You know you wanna cum all over my tits...show this striped slut just how much you like my breasts instead of hers."

Groaning softly, Gregg tried to hold out a bit longer, but the hot, slick breasts rubbing along his cock were just too much for him. With the way that Track used them, how she had gotten them so slick, how she was just begging him to cum all over them, there was no way that he could hold back. After all, she always looked so much better when she was covered with his cum.

So he came. His cock pulsed hard as it shot his load, some of it squirting between the raccoon's breasts as she bounced up and down his shaft, some of it getting her lips and chin. She turned away a bit there, but not by much. He groaned, the sight drawing another shot of cum out of him, soaking the area between her breasts even more, adding to the slickness there.

As soon as he was oozing instead of shooting, Track stood up with a smirk, looking over at the tigress. "Beat that, you skanky striped slut," she said.

"Oh, I can beat that easy," Pepper said with a grin.

Rather than walking over to the couch, the tigress turned around and went to her knees. Gregg's and Track's eyes went wide as the naked feline lifted her tail and spread her legs a bit, showing off her soaked slit, even reaching back and fingering herself a little bit. A few soft moans slipped from the tigress's lips before she pulled her finger back, licking it clean while they watched.

Pepper looked over her shoulder, fixing Gregg with a smile. "Get over here, Gregg. I know how much you like this pussy's pussy. Why don't you show this booby bandit just how much you prefer it to her tits?"

At the start of the challenge, Gregg had worried he might not be able to get it up for the second round, not if it came around too quickly. With a sight like that, though, his flagging cock immediately went the other way, going back up immediately. He grinned as he stood up from the couch, hurriedly crossing the room. He spanked Pepper once, enjoying the sight of her butt jiggling a bit, before getting to his knees behind her.

His cock rubbed against her pussy, and he trembled at the feeling of just how wet she was back there already. Had she gotten turned on from the show of his cock between Track's tits? Or had she just been looking forward to this so much that she had started getting wet in anticipation? Either way, he had never thought he'd see the tigress so wet without some foreplay first, and seeing her this way was just too sexy to ignore.

Hands on her hips, he yanked her back onto his cock, groaning in pleasure as he felt his cock get sheathed in her hot, wet depths. She was tighter, far tighter than the pillowy smooth slick space between Track's breasts, and he started thrusting away almost immediately. His fingers tightened their grip around her hips, digging in as he growled in lust.

Her moans were fuel on the fire for him, and he thrust away into her pussy, humping her in abandon. He knew that Track was watching, knew that the raccoon could see how much he enjoyed this, but he barely cared that this would probably piss her off. Instead of scaring him, it turned him on to know that she was watching him do this, to be seen fucking someone so hot as the tigress was.

The sound of Pepper's moans, his cock sliding in and out of her slick pussy, and her breasts slapping against her chest every time he rocked her back and forth made for great mood 'music', and Gregg could feel himself already getting close to his limits. Gritting his teeth, he tried to slow down, but his body had other ideas, just speeding up, ramming his hips forward faster, pushing his cock in deeper. His balls slapped against her pussy every time he pushed forward, and he could feel his pre and her juices running down his cock and over his balls, soaking them in their combined juices.

Before long, he could feel his climax welling up inside of him, could feel his balls starting to draw up. "Ugh...so...so close," he muttered under his breath.

"That's it...that's it, Gregg....cum in me," Pepper whispered back. "Just cum....cum in me..."

It was like a magic word or something. As she commanded, so he did. He wasn't sure if it was as big as the load that he left between Track's breasts, but he knew that it was pretty big, feeling it swirl around his cock as he kept thrusting through his orgasm, moaning loudly. It only got better as Pepper clamped down on his cock, squirming around under him in her own orgasm, and drawing more pleasure out of his cock as she tried to milk him for more of his cum.

Slowly, he slumped back, his cock pulling out of her pussy with a loud slurp. He managed to make it back to the couch before falling down, and almost fell right back off of the couch in the process, almost losing his balance as he hit the cushions.

The two naked females stood in front of him, their arms crossed. Cum leaked down the raccoon's chest, and from between the tigress's legs, running down their bodies to their feet. Both of them looked a bit sweaty, and entirely sexy to the wolf.

"So?" Track asked.

"Who's it going to be?" Pepper said.

Right...he had to choose. "Um..." He looked between them, at Track's tits, and at Pepper's pussy. Both of them were so very fun, and both of the females would do other things with him too. But which one to choose?

The silence stretched on and on, and just when Gregg was about to open his mouth, the females sighed. Pepper started getting dressed, as did Track. The raccoon looked at him with a shake of her head. "Look, we have things that we need to do. Why don't you give us a call, and then tell us when you finally figure it out? But trust me, you're getting nothing from either of us until you get this figured out," she said.

"Absolutely nothing," Pepper confirmed.

The two of them dressed in silence, walking out of the room and leaving him on the couch, all on his own.

A small smile started to grow on his muzzle again as he thought about it. If they were just going to let him call them...well, maybe he could salvage this situation yet. He just had to be very careful, and not make a mistake like this again.