Random little oneshot, hope you like it :)

"Here we are Ashy-boy." Gary said, dragging Ash into a night club.

"Why are we here exactly?" Ash rolled his eyes, he knew how a night out with Gary would always end, he'd pull some girl and Ash would be stuck as the awkward third wheel.

"Because you're 18."

"Correct."

"Single."

"Again correct."

"And never been with a woman." Gary smirked while Ash just glared.

"Unfortunately correct." Ash sighed. "And how is that going to change?"

"Look around you, drunk girls everywhere." Gary slung his arm around Ash's shoulders. "You don't even have to try, just give them a flash of that smile and they're yours."

"Really?" Ash asked in disbelief.

"Really." Gary nodded. "I will get you laid tonight, that's a promise."

"And why is tonight going to be any different?"

"Because I'm going to be your wingman, trust me Ketchum, with me by your side you'll be fighting the women off."

A blonde walked past the pair, stumbling due to high amounts she'd already drunk, spilling some precious drink on Gary's arm.

"Sorry gorgeous." She slurred with a wink before carrying on her journey.

"You're on your own mate." Gary smirked, following after the girl.

"Thanks for the support!" He called after Gary, his voice getting lost in the music.

Ash sighed, he could do this on his own, if Gary managed to get a girl every week how hard could it be?

Not fully paying attention to his surroundings Ash walked into a red head, causing her to fall, along with him, into the banisters. He took a moment to recover before he realised he was pinning the girl in place.

"Planning to get off anytime soon?" A voice asked, he assumed it was the girl.

"Oh, sorry… gorgeous." He tried the line he'd heard earlier, moving off her allowing her to stand.

The girl turned around and gave Ash a once over.

"Don't worry about it kid." She smirked.

"Kid?" Ash cried.

He stood up straight and looked down at her, she had to be at least a good five inches shorter than him, in heels.

"Yeah, does your mother know that you're out?" She laughed.

"What? She… I…" He stuttered, granted his mum thought he was spending the night at Gary's but that was beside the point.

"Oops, didn't you tell mummy about your night out? She'll be worried." She teased.

"I'm not a kid! I don't need to ask my mum's permission to go out." He crossed his arms.

"If you say so." Misty smiled at someone behind him.

Ash glanced over his shoulder to see a group of girls watching them closely.

"Well that's my cue to leave, see you around kid." She brushed past him and walked over to her friends.

"It's not kid! It's Ash!" He called after her but she was long gone.

He groaned to himself, maybe getting a girl wasn't as easy as he once thought.

Ash leant against the bar as he watched people on the dance floor, guys effortlessly finding a girl, why couldn't he do that?

He noticed the red head from earlier making her way towards the bar, he could always give her another shot.

"Hi." He said once she'd got closer.

"Well, if it isn't the kid. That better be a virgin."

"What?" Ash's eyes widened.

"The drink." She pointed to the glass in his hand.

"No it's not." He rolled his eyes.

"Aren't we just breaking all the rules tonight, kid?" She smirked.

"It's Ash, okay? Ash!" He moaned, trust him to pick the most difficult of girls.

"Cute." She smiled.

"And you are?"

"Misty."

"And can I get you a drink Misty?" He offered.

"I'm never one to turn down a free drink. Vodka and coke please."

"Coming right up." Ash said leaning over the bar to get the staff's attention.

"Great." Misty mumbled, barely loud enough for Ash to hear.

"Here you go." He turned back to Misty with two drinks and held one out for her.

"Thanks." She took the drink from Ash and had a sip.

"So, you from…" Ash was cut off by Gary coming over.

"Ashy-boy." He slapped him on the back. "You alright mate? And who's this beautiful creature?" Finally noticing the girl.

"Misty." She gave Gary a once over, much like she'd done to Ash earlier.

Ash noticed a blue haired girl that had arrived with Gary, now leaning against the bar for support. He couldn't help but wonder what had happened to the blonde from earlier.

"Helping Ash celebrate his birthday?"

"Birthday? Wow. Finally reached double figures kid?" Gary laughed at Misty's statement.

"I'm 18!" Ash called out, getting sick of the abuse.

"Wow, aren't we a big grown up boy?" Misty raised her eyebrow.

"Something like that, and it's not my birthday." He said turning to Gary.

"Well it was last week, what's the difference?" Gary turned his attention back to Misty. "And you're taking good care of my boy?"

"Oh yeah, I'm looking after him." Misty smirked again.

"Good, because he needs a little love right now."

"And why is that?"

"You see Misty, his heart has been broken." Gary said, putting his arm around her.

"Has it now?" Misty gave Ash a small smile, showing she wasn't buying any of Gary's spiel.

"Yeah, last girlfriend completely screwed him over, left him shattered."

"Oh no, and why did she leave him?" She was actually enjoying this a little bit.

"Couldn't handle that animal in the bedroom." Misty bit her lip to stop herself from laughing.

"Gary." Ash warned but he ignored him.

"He just needs a little TLC right now and you look like just the sort of girl to provide that comfort." Gary smirked.

"Wow, that's a little out of my depth. I'm better at wild, drunk hook-ups not nursing a broken heart back to life." Misty shrugged and both the boys' eyes widened. "Sorry, thanks for the drink kid." She gave Ash a wink before walking back towards the dance floor.

Ash watched her go and started to follow after her, only to be pulled back by Gary.

"Where do you think you're going?" He asked.

"To go talk to that gorgeous girl I was with earlier." Ash rolled his eyes.

"Forget her, she's a lost cause."

"Only because you scared her away with your broken heart crap."

"Regardless, I've got you someone else." He turned Ash towards the bluenette, almost passed out on the bar.

"Hi." She smiled at the pair.

"Ash, this is Dawn."

"Great, hi Dawn." Ash looked over his shoulder but he'd lost Misty in the crowd.

"Dawn's just broken up with her boyfriend, why was that again?" Gary asked.

"I found him in bed with another girl." Dawn slurred.

"In bed with another girl, isn't that awful?" Dawn hiccupped in response. "Now, she's looking for someone to get revenge with and I think that someone could be you."

Ash glanced over towards Dawn, she was a mess, could barely hold up her own head, not really the type of girl he was going for.

"Maybe some other time." He tried backing away again.

"There won't be some other time." Gary pulled him back. "Now is your only chance. Get with the girl."

"Let's call her plan b." Ash shot off into the crowd before Gary had a chance to pull him back.

"Ash!" He called after him but it was too late.

Ash made his way through the crowd on the dance floor, being bumped numerous times before he noticed Misty dancing with her friends. He came up behind her and placed his hands on her waist.

"I just can't seem to get rid of you can I, kid?" Misty said glancing over her shoulder.

"Apparently not." Ash smirked.

Misty turned around in his arms and looked up at him.

"So what can I do for you?"

"I'll settle for a dance, in return for that drink I bought." He gave her a slight squeeze.

"Seems like a fair trade to me."

She got closer to him and began swaying her hips from side to side, Ash awkwardly tried to follow her rhythm.

"Kid, you need to loosen up a bit."

She took hold of his hips and pressed herself against him, moving his hips with hers.

"You'll get the hang of it." She winked.

She turned once again in his arms until her back was against his chest, making grinding movements with her hips she placed a hand on the back of his neck. While making slight thrusts Ash trailed his hands over her body, imagining what it would be like to take her home tonight.

"Misty!" A brunette girl appeared in front of the pair, causing Misty to freeze.

"What's wrong May?" Misty asked.

"It's Dawn, she's being sick." May explained.

"Oh Jesus." Misty said, detaching herself from Ash.

"She's in the toilets." May grabbed Misty's arm and pulled her away.

Without even a glance back or an explanation Misty walked off. Ash slowly walked off the dance floor and sat down, she'd disappeared again.

"What happened to Red?" Gary asked sitting next to Ash, a new girl with him. How did he manage to do this?

"Friend emergency." Ash shrugged.

"Well you left it too long and plan b is no longer an option, just like I told you." Gary said smugly.

"Yeah I know, she was the friend emergency."

"Really, they're friends? Well maybe you can see if they both want to…"

"Stop!" Ash cut Gary off. "Don't even finish that sentence."

"Geez Ash, why so touchy tonight?" Gary asked.

"Long night."

"Well if you took my advice you wouldn't be so pissed right now."

"What advice?" Ash gave him a look.

"I told you to go for drunk girls, not stuck up bitches."

"Misty isn't stuck up!" Ash defended.

"Calm down Ashy-boy, you've known the girl for a couple of hours, you can't honestly tell me you've fallen for her already."

Ash didn't respond instead just stared down at his feet, sure he thought she was absolutely gorgeous and he enjoyed the way she teased him but had he really fallen for her? He had spent most of his night following her around when all said and done.

"Oh god Ash, you cannot be serious." Gary said, pulling him out of his thoughts. "The plan was to get laid not find a girlfriend. What am I gonna do with you Ketchum?" Gary shook his head.

Ash shrugged slightly and quickly changed the subject off himself.

"So who's this?" He gestured to the girl next to Gary. "Plan c?"

"You wish! This is Leaf." Gary placed his hand on Leaf's thigh. "And she's all mine." He turned to her with a smirk.

"You bet I am." She smirked back before pulling him down towards her lips, Gary eagerly responding.

"Oh lord." Ash said, standing up and leaving the pair alone.

Ash stepped outside to get some air to see Dawn sat on the steps.

"I'm so sorry Paul!" Dawn cried down the phone. "Take me back, please, I love you."

Ash was tempted to go over and offer some support but noticed the brunette from earlier was with her.

"Dawn, sweetie, hang up the phone." She pleaded.

At the bottom of the steps he noticed Misty talking to a bouncer, probably trying to convince him her friend wasn't drunk enough to get kicked out. Ash began walking down the steps towards Misty, just as the bouncer began to leave.

"Thank you!" Misty called after him, she turned around and almost walked into Ash. "I'm beginning to think you're stalking me."

"You're not that lucky." Ash smiled.

"No offence kid, but you're not really my type." She said, trying to get past him and back to her friends.

"And why not?"

"I prefer a mature guy." She shrugged.

"Seriously, how old are you?"

"19."

"Only a year older than me!" Ash cried out.

"Yeah, but in girl years that's a hard five." Misty smirked.

"So that's it? You're writing me off because of age?"

"Kid, don't make this harder than it needs to be." She looked away from him.

"Age is just a number." He tried.

"It's not just the age thing." Misty sighed.

"Then what is it?" Ash asked, desperate to know what he could do to get this girl.

"Because I know what guys like you are all about."

"Guys like me? What does that even mean?"

"At first, you came across as this hopeless, lost, adorable guy and then your friend shows up playing the wingman." Misty rolled her eyes. "You guys prepare that pile of shit you call a sob story beforehand or is it all spur of the moment?"

"I swear I didn't know Gary was going to do that I thought…" Ash started but was soon cut off.

"Spur of the moment, nice touch." Misty nodded.

"Would you just listen to me?" Misty stared at Ash, waiting for him to continue. "That whole broken heart story? All Gary. I'd never do something like that. I genuinely liked you and wanted to get to know you, Gary just got involved because he thought he was doing me a favour."

"How was that doing you a favour?" Misty crossed her arms.

"Because I'm a virgin!" Ash's eyes widened, he hadn't meant to say that and quite so loudly.

"Is this another one of your stories?" Misty raised her eyebrow at him.

"Nope, all true." Ash groaned and sat down on the wall.

"What's the big deal? So you're still a virgin? You're only a kid, you've got time." Misty said sitting next to him.

"It's not that I just… I've never even been with a girl." He looked towards Misty.

"I know, you just said…"

"No, I mean at all. For anything." He looked down at his feet.

"Anything? You've never even kissed a girl?" Misty's eyes widened.

"I just haven't found the right one yet." Ash explained.

"Yeah, but you're 18, I just find this a little hard to believe that's all."

"Well have you ever kissed a girl?" He asked, looking up.

"Yeah."

"What?" Ash raised his eyebrow.

"I was experimenting." Misty shrugged.

"And?"

"We're only okay, you're not missing out on much." Ash laughed slightly.

"How come you've managed to kiss a girl when I can't?"

"It's all about confidence kid, if you took control of the situation you'd have probably kissed a girl by now." She smiled.

"Control?"

"Yeah, girls love a guy to seduce them, take them by surprise. Be spontaneous and…" Misty was cut off by a set of lips pressed against hers.

Ash put his arm around her waist and pulled her closer, he lightly brushed his tongue against her lips, praying he hadn't made a wrong move. Misty slowly opened her mouth, allowing Ash entrance, his tongue exploring every corner of her. Misty moaned as their tongues danced, her hands making their way upwards and into his hair. Ash's hands began travelling in the opposite direction until they were just below her hips, making small patterns with his fingers.

"Get in there Ashy-boy!" A voice called out, causing the pair to break apart.

"Gary Motherfucking Oak." Ash grumbled. "I'm gonna kill that guy."

"He's harmless." Misty laughed. "Just trying to be a friend, in his own special way."

Ash glanced over his shoulder to see Gary stood in the doorway, he gestured for him to leave. Gary shrugged and went back inside. Ash turned his attention back to Misty and smiled.

"So, want to come back to mine?"

"And meet mummy?" Misty smirked.

"Or yours." Ash said sheepishly.

"Don't do this."

"What do you mean? I thought…"

"Look, you're a nice guy and I do like you but don't just give your virginity away to the first person willing to take it. Wait until you find that one person, make sure they're special or you'll always regret it. Believe me." Misty sighed, running a finger through her hair.

"So your first time…" Ash trailed off, worried he was getting too personal.

"Let's just say the first guy I was with was very similar to that lovely guy Gary." Misty sighed. "Hold on to it, in the long run you'll be glad you did."

"Misty!" May called out. "We're going."

"See you around kid." She gave him a quick kiss before getting up and walking off with her friends.

Ash sighed and soon went inside himself, the cold getting to him once Misty had gone.

"Alone again?" Gary asked, finding Ash slumped in a corner chair.

"Yeah, Misty took off."

"You let her get away? What's the matter with you? She could have been the girl."

"She wasn't interested in taking it any further." Ash shrugged.

"Seriously? But she was all over you back there. Fucking prick tease, I hate that." Gary grumbled.

"She's not like that." Ash smiled. "She was something else, unforgettable."

"If you say so." Gary shook his head, in his opinion any girl who wouldn't put out was far from special.

"I think I'm going to head home." Ash said getting up. "Not really feeling it tonight."

"Alright, I'll see you tomorrow with the details from my night." Gary smirked.

"Great, look forward to it." Ash rolled his eyes. "Where's your girl anyway?"

"Getting drinks, should probably get back to her. See you later." Gary gave him a nod before going in search of Leaf.

Ash dragged himself out the club and to the nearest taxi rank.

"Come on, she's not going to throw up in the taxi! I swear." Ash smiled to himself, he recognised that voice.

He looked up and sure enough there was Misty arguing her side while May tried to hold Dawn up.

"Sorry, that's policy." The worker explained.

"Well how am I meant to get her home?" Misty glared at the man.

"I'm sure you'll find a way." He looked back at his paper, indicating the conversation was over.

"Dick." Misty muttered under her breath.

She turned and once again came face to face with Ash.

"One of these days I'm going to turn around and you're not going to be there kid."

"Nice to see you too." Ash smiled.

"Mist, think you could help me get her outside then I'll try Drew." May asked.

Misty rushed over and took the other side of Dawn, together they walked out the taxi office and placed Dawn on the pavement.

"She okay down there?" Ash asked, having followed the girls out.

"She'll be fine, won't you sweetie?" Misty asked, giving Dawn a nudge.

"I'm going to vomit again." Dawn moaned.

"See? Right as rain." Misty smiled up at Ash.

"Hey honey." May said into her phone. "Yes, I know it's 3 in the morning… Yes, I know you have work tomorrow… I need you to come pick us up… I'm really sorry about the timing… No, this time it's Dawn… Thank you babe! Love you." She hung up the phone. "Drew's on his way."

"Your boyfriend is a life saver." Misty smiled.

"I know." May smiled back. "I'm going to go get her something to drink, you two okay to look after her?"

"Yeah, we'll be fine."

May walked off towards a chip shop down the high street leaving Ash and Misty alone, Dawn practically asleep.

"Did you have a good birthday kid?" Misty asked.

"I told you, my birthday was last week."

"I know, but I guessed this was your big celebration as Gary was desperate for you to get your cherry popped." Ash glanced nervously towards the girl on the floor. "Don't worry about her, she won't remember any of this tomorrow."

"Fair enough." Ash nodded. "And he wasn't that desperate, we know he's reached that stage when he offers to pay for someone."

"Let's hope it doesn't get that bad." Misty laughed. "But I meant what I said, wait for someone special."

A car pulled up in front of them and a green haired man got out the car.

"Drew!" May called out, running down the street with a bottle of water in her hand. "Thank you so much." She breathed once she got reached him.

Together May and Drew carried Dawn into the car and forced her to drink the water.

"I should be going." Misty turned towards Ash. "It was nice meeting you kid."

She began walking towards the car when Ash reached out and grabbed her wrist, stopping her in her tracks.

"Wait."

"What?" She spun back round to face him.

"Can I have your number?" He asked, before he lost the nerve.

"And why would you want that?" Misty smirked.

"I like you, granted you've been turning me down all night but there's something about you." He smiled. "And who knows? Maybe you'll turn out to be someone special."

Misty bit her lip and smiled up at him.

"You really are adorable kid, you know that?"

"Is that a yes?" He asked, hopeful.

"Yeah." She grabbed a pen from her bag and scribbled her number on the back of his hand.

"Thanks." He smiled.

"No worries." She began backing towards the car. "Give me a call sometime Ash." She smirked before getting in the car.

Ash stood there until the car was out of sight, he looked down at the number on his hand.

After everything that had happened tonight, he didn't feel like such a little kid any more.

So there it is :) may make this into a two shot depending on how I feel, who knows?

Please review :) thanks