Notes: Firstly, let me apologize to everyone who's been waiting for The Long Way Home to continue - by now, I've rewritten the end two times, but hopefully, I'll decide it's uploadworthy the third time (which is, at least, almost done).

In the meantime, though, I hereby present a plot bunny that's been haunting me for two weeks and is finally ready to be unleashed!

Setting: some time during the early seasons (seriously, when exactly Dean would hit his 100th one night stand is entirely up to your guesses)

Pairing: mentioned Dean/Random girls, eventual Wincest (mainly Top!Sam, Bottom!Dean)

Warnings: This gets dirty. Not as dirty and explicit as it could be, but still worse than most stuff I've written so far.

Disclaimer: I don't own Supernatural or anything related, I simply enjoy its awesomeness and great fandom :D

So, with everythign said and done, here we go...

One Hundred

99 and counting

Double D.

Glancing after their waitress, Dean silently nodded to himself.

Definitely a double D.

With long blonde hair and a curvy body, she looked pretty tasty. Considering she was a waitress and, as such, in pretty decent shape, she might actually turn out lots of fun.

But...after pondering for a moment, he came to the conclusion that she would not be enough fun. Enough fun for any other night, surely, but not for this occasion.

Heaving a sigh, he returned his attention to his brother, who, as it turned out, had been watching him over the breakfast table all the while.

So Dean had been intending to start the day with a nice review of their respective progress on the case, but the bitchface greeting him rendered that particular plan all but impossible from the very beginning.

"Dean, what the hell is wrong with you?" Sam accused in barely concealed annoyance.

Furrowing his brows, Dean blinked back. What? He did not even get to come up with any thesis on what the hell he had done wrong this time – they were simply eating in quiet, for crying out loud! - when Sam finally bothered elaborating. "Our waitress isn't just your type," he pointed out with a confusingly impatient nod towards the blonde in question, "she's hotter than basically any chick you picked up the last times you were this desperate."

Dean's jaw dropped. "This desperate?" he repeated incredulously, "I'm not – "

Sam rolled his eyes and released an even more infuriating sigh. "Our last three motel rooms were reeking of your sexual frustration, man," he pointed out and ran a hand through his hair as he leant back in the chair, "Seriously, this is none of my business, just..." He released another sigh. "Get this taken care of, man."

Inhaling deeply, Dean took a few moments to gather his composure. He hadn't even intended for Sam to notice, at least not yet, and not like this. Then again, though, he hadn't exactly expected this to become quite as difficult, either.

"Please don't tell me you need me to get her phone number for you," Sam pressed on when Dean was still failing to reply a minute later, and it finally shook the older brother out of his reverie.

"Nah, I'm fine," he stated simply and reached for his cup of coffee.

But Sam's stare kept drilling holes into his skin. "No, you're not," he countered with a frown, "I thought we'd established that."

"We also established that this is none of your busniess," Dean pointed out gruffly, but his brother would have none of it.

"Look, I wouldn't put it past the Trickster to orchestrate something exactly like this just to drive the two of us insane," Sam argued in exasperation, "So if you not being yourself is indeed a case, then it is my business."

Sighing, Dean took a sip of his coffee. "It's not a case," he assured his brother.

At first, Sam had looked ready to let the matter rest. When Dean added, "It's a mission," with a meaningful look, though, the younger brother slumped his shoulders with an expression that said, I should have known. "So basically, you're setting up some kind of sick, personal sex record," he summarized with what felt like the hundredth sigh that morning.

Apropos one hundred...

"It's not just some record, Sammy," Dean explained and leant forward meaningfully, "We're talking about the big one hundred."

As expected, his brother reacted with an exasperated sigh. His bitchface yet had to reappear, though. "Please spare me the details," he commented and finally resumed eating his rather unappetizing meal.

Now that they had already gotten to the topic, though, withholding the crucial part was the last thing on Dean's mind. "99 girls, Sammy," he elaborated with a grand gesture, "Some hot, some not, but all of them were great in their own way, which in turn means..." He lifted his finger for stress. "That Miss No. 100 has to be amazing."

As intended, Sam was beginning to look uncomfortable. "Too much information, Dean," he pointed out, but still seemed to consider the news in regards of their earlier problem – his brother's suddenly high standards in women and his subsequent unnerving behaviour.

"Our waitress is cute and all," Dean explained and tilted his head, "but not Miss 100 cute."

Sam heaved another sigh. "That's stupid and you know it. Considering you barely even remember the girls you make out with the morning after, I doubt that number is particularly reliable anyway," he stated and massaged his temple, "Most likely, Miss 100 was that freckled hooker back in Detroit and you're way past 110 already."

Frowning deeply, Dean was slightly disturbed Sam seemed just a bit too informed on his love affairs. More importantly, though, he refused to acknowledge his brother's argumentation. "Detroit, yeah, I got to give her that much, she certainly was flexible," he summarized a hazy memory from months ago, "but not – "

"Not Miss 100 flexible," Sam finished the sentence in his stead and sighed, "I got that."

"A man's got to have his personal highlights every once in a while," Dean defended himself. Especially with their lifestyle the way it was, he had all the reason to enjoy those little pleasantries all the more.

"Just...whatever," Sam humoured his brother at last, "Seriously, your little kinks are none of my business, just..." He grimaced, reconsidering his wording, "Make sure your self-induced sex deprivation doesn't get us killed."

Again, it was Dean's turn to frown. In all honesty, he had told Sam because the bugger wouldn't shut up, and then because he simply wanted to tease him. Now that the bombshell had been dropped, though, they might as well make the best of it. "You could help me looking, you know," Dean suggested with a casual shrug and flung a spare rib into his mouth, "You don't happen to know some gal that's just...you know, wow?"

Sam rolled his eyes, which landed on the blonde serving the guests two tables over. "If this waitress doesn't meet your definition of wow, there's something seriously wrong with you, man."

Joining his brother in oogling the poor girl, Dean had to rephrase his thoughts. "Of course she is, I mean, yeah," he agreed slowly and tilted his head, "but she's just too much like others I've already had. I need something different, something new – someone sexy, challenging and – " He subconsciously licked his lips. " – memorable."

Again, Sam sent him that exasperated glance. "If it's taken you three towns and you still haven't found anyone in spite of this – " He nodded once again towards the waitress, whose short skirt left very little to the imagination " – it's probably hopeless anyway."

Dean opened his mouth to protest, but just in that moment, his brother's phone rang. It was kind of fascinating to watch him switching into business mode within half a second, really, but the call only lasted half a minute anyway. "We got a new lead," Sam summarized as he chewed down the sad remains of his sad vegetarian meal, "We should get going." With that, he got up and handed the waitress a couple of bills before striding towards the exit.

Striding after his brother, Dean met him at the Impala. He had half-hoped the conversation to be over, now that they had to get back to work – but once again, Sam's bitchface told him otherwise.

"Seriously, Dean," the younger brother chided as they were standing next to the car, "we've got cases to solve and demons to hunt. Don't make this even more difficult." With that, he produced something small and white from his pocket and handed it to his brother.

Frowning, Dean found himself looking at a paper napkin with a phone number and a red lipstick mark on it. So Sam had gotten her number after all? Maybe on other days, Dean would have felt endeared by his brother's care – now, though, it was finally him who was getting exasperated. "Sam, this is my choice," he pointed out crossly, "She's cute, but not Miss 100 cute."

Rolling his eyes, Sam yanked the car door open. "Alright," he pouted, "If you really need something new, challenging and memorable..." He met Dean's look in a half-glare, "why don't you look for Mister 100 instead?"

Dean's eyes widened. "Dude!" he protested weakly, trying hard to force that particular nation out of his mind for all eternity.

But Sam, the bastard, only chuckled and looked as if he was actually giving that idea another thought. Of course he would take any chance to get back at Dean for all the awkwardness the mere conversation had put him in.

"Seriously, though," Sam pondered, "It might even work." A scheming grin formed on his features. "You're good-looking enough to turn even straight men gay," he explained and arched an eyebrow in challenge, "and I'm pretty sure Chuck the lumberjack will leave a lasting impression on you." With another light chuckle, he entered the car at last, leaving a flabberghasted Dean standing in the cold morning air.

It took about a minute for the older brother's brain to unfreeze from the mental images he certainly hadn't asked for.

"The fuck, man," he complained as he sat down in the driver's seat and accidentally picked the music cassette he knew Sam hated the most, "You sure know how to spoil a man's dream." With that, he turned the music on extra loudly.

He didn't hear it, but he could still see Sam sighing. "Just call the waitress," Sam all but pleaded once again.

Too bad Dean couldn't hear him over the stereo. Sam had just lost his license as anyone's dating advisor anyway.

- TBC -