A/N: Okay, so this story… I don't really know where I got the idea, but I kind of it. Just because I think Flynn is totally the type of guy who has a lot of one night stands. Let me explain a few things. This still takes place in the time period that Tangled does, but it's kind of AU. Rapunzel escaped the tower on her own; none of the stuff in the movie ever happened. And now she's just chilling in town or something. That's it.
Flynn Rider was spending his evening as he usually did: alone, in a bar, looking for girls. Not any girl in particular, really, just one that looked willing to get into bed with him. He wasn't very picky. As long as she wasn't hideous, she would probably work. He had a few preferences, sure – and that's why he liked evenings like this. This place had lots of girls in it tonight. He could take his pick.
He sipped on his beer as he looked around, seeing what his choices were. Some of these girls were hotter than others. Some looked really slutty (not that he minded that or anything) and some were actually really pretty. Some already seemed to have men with him, so he ruled those out because he wasn't into sharing, unless it was himself being shared between two or more girls. Soon enough he saw someone sitting at a table in the corner, and she made him forget about everyone else for a minute.
She was tiny – he almost wouldn't have noticed her at little if he hadn't be specifically looking – looking around the rest of the bar with huge, green eyes. She looked a little out of place as she watched everyone, taking a sip of her drink every once in a while. Her brown hair was cut very short, a pixie cut that was a little uneven around the bottom, but it looked very cute on her.
Flynn pretty stopped looking at every other girl in the place, just focusing on her. She was, well…she was amazingly attractive. She was small and sexy and innocent-looking and best of all she was a brunette. That was it. She was the one he wanted. She was the one who would keep him company tonight. There was no doubt in his mind of this, because he had never had a girl turn him down before. Well except that one time, but that didn't count.
He stood up and confidently made his way over to her table, the alcohol in his system probably helping with that. She noticed as he got nearer, her eyes following him. And her eyes – god, her eyes were gorgeous. She was definitely the best looking girl Flynn had found in a bar in a long time.
"Hey, sweetheart," he said, giving her a smile as he stood next to her. "How are you this evening?" He had a fair bit of experience in dealing with girls. It didn't take much for him to get them into the palm of his hand.
Her eyes were still fixed on him, in surprise and shock. Someone was talking to her again. She wasn't so sure if she liked this. She had been here a few days, staying in the inn that was part of this bar, and everyone who had tried to talk to her had been strangely flirtatious men. This guy did look much more attractive than the others, however, and closer to her age. Still, she wasn't that great with talking to people. Before a few weeks ago, she had never talked to anyone but her mother. "I'm…I'm alright," she said. "And you?"
"I'm pretty great," Flynn said. "Look, you seem kind of lonely over here all by yourself. You want some company, babe?"
"Um…" She gave him a soft smile. "Company would be good, I guess." To be honest, she was pretty bored. She didn't know what there was to do around here, so most nights she would just come down to the bar and watch everyone. The past couple nights she had given drinking a try. She didn't much like the taste, but the results were…interesting. She had only had about one drink by this point, so she was mainly in her right mind.
Flynn smiled and sat in the seat next to her. "Allow me to introduce myself. I'm Flynn Rider." He gave her another smile, his best one yet. "You've probably heard of me."
"Flynn Rider…?" It sounded familiar to her. "Oh, the guy from the wanted posters?" she said suddenly. She remembered seeing them posted around the streets. "You look different in person. Your nose is different."
He felt the urge to roll his eyes. Of course. But he didn't let that show, and continued to smirk at her. "I'm also much more dashing than they give me credit for. You know, most people don't know this about me, but…" He leaned in closer to her, half-whispering into her ear, "I've got a thing for brunettes."
She squeaked, blushing a bit. Good thing she was a brunette, because she hadn't been a few weeks ago. She used to be blonde until she escaped from home and cut her hair, turning it brown.
He grinned, pulling away from her. "You know, you look very beautiful?"
"T-thank you," she said. Maybe it was that stupid drink that was making her stomach all fluttery, but she really liked this Flynn guy. He was good looking and he was being very nice to her. She had always been scared of people before she escaped, but maybe they weren't bad. "You too," she muttered, glancing at him before looking down and turning red.
"Well thank you," he said. He looked around, as if to make sure no one was listening, and then said a little quietly, "Hey, you wanna get out of here? It's kind of crowded and I really think we could get to know each other better if we were alone."
"Sure," she said quickly. It sounded like a fine idea to her. "I have a room here. If you wanna use that."
Perfect. Much easier than getting his own room – or stealing someone else's. "That sounds great. Do you want to lead the way?"
"Of course," she said, standing up quickly and stumbling a bit. She was nervous. She'd never had a man in her room before, ever. "Just follow me." She went to the back of the bar, climbed a set of stairs and led him down a hallway before opening the door to her room.
She closed the door once they got inside, and Flynn quickly went over to lock it. She ignored this. "So…how are you?"
Flynn couldn't help but find her whole innocent act amusing. With how easily he had gotten her to take him up here, he was sure she knew exactly what she was doing. Her cuteness would probably only last for so long. He was sure she could get crazy in bed. His trousers tightened just thinking about it.
He grinned, gently taking one of her hands. "You know, I never got your name," he whispered, nibbling on her neck. It was always polite to ask them their names, even if he didn't actually care about it.
"It's Rapunzel," she muttered, her heart pounding in her chest due to the way his mouth was working on her. She had never had anyone kiss her before, so when he moved his mouth to give her a full kiss on the lips she wasn't at all prepared for it. But she was a quick learner, moving her lips against his. She knew how to do this, having spent several nights in the bar watching many couples embrace in public. He pulled away after just a few seconds.
"Rapunzel," he repeated. "Well Rapunzel. I think you'll enjoy this." He leaned in and kissed her again, leaving a fluttering sensation in her stomach. She couldn't believe he liked her so much that they were actually kissing already! She didn't even know him. But then again, he had probably been drinking, and drunken couples were always very keen on kissing. But she had to admit she saw the fun in it now. Maybe she should have tried this before!
"Well, I'm enjoying it so far," Rapunzel said, smiling a little.
He pulled away. "You know, you look pretty young. How old are you?"
"Eighteen," she said, a little nervously.
He looked at her and smiled. Not too bad. He'd been with younger, though not by much. "Twenty-six," he replied.
She gave a little nod at this. He simply grinned at her as he fumbled with his belt and kicked his shoes off. Rapunzel wasn't quite sure where he was going with this, but he seemed to be trying to get undressed. She froze up a little and just stared at him.
"Don't worry, I have protection," Flynn said upon noticing her stare. He pulled something small out of his pocket and kind of held it up to her, but she had no idea what is was. Then he went back to what he was doing. "Why don't you get your clothes off, baby? I'm sure you look even more wonderful without them," he said, glancing up at her with a smile that was kind of infectious.
She blushed. So that's what we wanted? She couldn't say she was surprised, but she wasn't sure if she should agree to it… "Oh, um, okay," she muttered, tugging on her dress a little but stopping when she saw he had his pants down.
"You okay?" he asked. He was used to girls looking at him when he undressed (he was pretty happy with the way he looked, needless to say), but she was different than the others.
"Yeah, I just…I never…" she muttered, looking down at his underwear, or more specifically the strange bulge in it.
Flynn stopped what he was doing, kicking his pants off from his feet, and stood up straighter, looking at her. "Never what? Shit. You're not…you're not a virgin, are you?"
Rapunzel nodded and looked rather embarrassed. "Um, possibly?"
"Shit," Flynn said again. He hadn't been expecting that. He assumed she was pretty experienced, judging from the way she was acting before. Not to mention she was at a bar – he was used to only sluts hanging out in bars. "I, um…well that's fine I guess." He wasn't really sure what to do. He hadn't been with a virgin in a long time (the girls he had been with lately were like the opposite of that). He wasn't sure he wanted one. But this Rapunzel chick was hot as hell and he still wanted to bang her either way.
Rapunzel smiled at him shyly. "Alright," she said.
"Yeah, so…just take your clothes off and I can show you where to go from there." He would rather just get right to it, but knew he would have to take it slow for her. He smirked as he watched her began to take off her dress, revealing lots of beautiful skin underneath. No matter if she was a virgin or not, this was going to be worth it.
She stood there in her undergarments, simply looking at him. Eventually his eyes landed back on her face. He stammered slightly before talking again. This girl was really hot. "So, so you're sure about this?" he asked.
Rapunzel thought for a few seconds. Was she sure? She didn't exactly know what she was doing, but she liked this Flynn guy, and if he wanted to do this then she had no problem with going along. "I'm sure," she said quietly, giving him a small smile and a nod.
Flynn grinned. "So how about taking everything off?" he asked. He was usually too lazy to take off a girl's clothes for her, even though some of them were into that. He watched her as she undressed the rest of the way, very pleased with what he saw. After she was done he came back to his senses. "So, you can lie on the bed, I guess? And I could take over?" He was used to girls giving back to him equally, so it was strange that he would have to do everything tonight. Virgins are too much work, he thought bitterly.
Rapunzel lay down on the bed, looking up at the ceiling, her heart beating very fast. She had never had anyone see her while she was this exposed. Maybe she should have got to know Flynn a little more first… But apparently in the real world you didn't have to get to know someone before getting intimate, so she guessed this was alright.
Flynn positioned himself over her and began kissing her again. It was strange, kissing, but Rapunzel was really starting to get the hang of it. She hoped she was doing alright. She was, because Flynn couldn't even tell that she had never kissed anyone before.
Flynn wasn't into foreplay unless he was in the mood, which wasn't right now. Usually if he went too long with someone without actual intercourse they'd actually think he liked them, and that was never a good thing. Although Rapunzel…he liked her a bit more than most girls he did this kind of thing with. Not because of her looks – she just seemed like a nicer person. He didn't want to waste time being all romantic on her, but he figured he might as well be nice since it was her first time.
He kissed her a while before exploring her body a little. It was intended to calm her down, but the more places he touched her, the quicker her heartbeat would get.
"You alright, hun?" he asked, kissing her collarbone.
Rapunzel gave a shaky nod. "Yes, I'm…f-fine." She had never had anyone touch her in this way before. Flynn really must like her a lot if he was doing all this. She kind of liked what he was doing, even if she was nervous.
Flynn gave her some more kisses before pulling away. He took his underwear off, trying to ignore Rapunzel's stares (this girl was too funny), and slipped on the condom. Better safe than sorry. He sighed, looking at her. She said she was sure about this…
He positioned himself again, propping himself up on his hands. He felt a lot worse than he should have. It was just that he felt kind of bad taking away her innocence like this. Girls always imagined their first time to be magical and romantic and perfect, and that was not at all what he was going to give her. It was sad, really. She deserved to be in love with the one she was losing her virginity too. But he wasn't going to stop just because he felt bad for her. "This might hurt a bit," he said. "Are you ready?"
Rapunzel felt like being brave and kissed him quickly, the first kiss that she had initiated with him. "Yes. I'm ready." She wasn't exactly sure what he meant by it hurting, but she trusted him and she knew this would be okay.
Flynn took a deep breath and slowly pushed into her. Rapunzel gasped, not really expecting it to feel like that. It hurt a lot and she felt tears form in her eyes. "Shh," Flynn muttered, feeling more sympathy for her than he should have. He wiped a tear away with the back of his thumb. "It'll feel really good in a minute or two."
He was right about that. The pain ended soon enough and Rapunzel couldn't help but smile a bit at being so connected with someone. She hadn't expected things to turn out like this, but she was glad that it did.
Flynn grinned at her, giving her a kiss. She just looked so goddamn cute right now that he couldn't resist. Anyway, it was driving him crazy being inside of her and not moving, so he slowly moved his hips away just to go back in. Rapunzel hadn't been expecting this and cried out a little, and Flynn ignored her, because she would get used to it soon enough.
He picked up his pace a little, and Rapunzel seemed to be alright with this. She moaned and wrapped his legs around him, holding onto him. "Flynn," she moaned. This was nothing like she had imagined this to be, but it wasn't bad. She was kind of enjoying it.
Flynn wasn't used to girls saying his name during sex. It made things a little too…personal. Although he didn't really mind, because it was good that they remembered the greatness that was Flynn Rider. "Oh my god…babe…" he groaned, speeding up more. He let out a slew of unintelligible swear words while Rapunzel just made soft, cute noises.
Finally he couldn't take it anymore, but he doubted she was anywhere near close with it being her first time. He reached his hand down between her legs and began playing with her until finally she moaned his name again and loosened her grip on him a little. Flynn came at the same time she did, collapsing on top of her. He rolled off, onto his back, and pulled the covers over them.
Rapunzel had no idea what to say. She couldn't believe she just did that. She had been really into trying new things lately, apparently. But it was…well, she didn't really know how to describe it.
Flynn was still breathing heavily. "Well, you are awesome, my dear." It was true. She was a pretty good fuck, even if it was her first time. One thing was for sure, he definitely didn't want to leave her quite yet.
"Did I…do everything right?" Rapunzel asked nervously. She hadn't done much but lie there; she wasn't sure what else there was to do.
"You were perfect, baby," Flynn said, kissing her. She was better than any girl he'd had in the past month or so, but that was probably just because of how cute she was.
Rapunzel giggled, getting butterflies in her stomach every time they kissed. "Thank you, Flynn."
He grinned at her. "Well, you're welcome, beautiful." He sighed contently, looking back at the ceiling. She was a lot more pleasant to be around than most girls he was with. His drinks from earlier must have been wearing off, because he felt almost totally sober again. He was sober and he wasn't disgusted being in the same bed with her. That was something new…
"You know, the night's still young," Flynn began. "We could still have a lot of fun together."
Rapunzel started imagining things at that, but she decided to ask what he meant. "Like what, exactly?"
"Hmm…" Flynn was already trying to think of ways to get back inside her, and he wasn't sure how quickly she would be up for that. Being with a girl without doing sexual things with each other was just a waste of time though. "Could I maybe buy you some drinks?"
Rapunzel had seen that move from the nights she had sat at the bar. Men tried to do that when they wanted to flirt with a girl. She herself had even been offered drinks a few times, but she refused, because she didn't exactly trust people yet. With Flynn, though, she guessed she had no problem accepting the offer. "Alright," Rapunzel said, smiling and nodding. She sat up, keeping the cover around her, and looked around for her clothes.
It would be a waste to get her dressed again, with what he had planned for later in the night… "Actually, you can just stay right here. I'll go get some drinks and bring them up. Sound good?" Flynn stood up from the bed and got his clothes back on.
"Yep. I'll be here," Rapunzel said. Flynn left to go back to the bar and Rapunzel fell back onto the bed, smiling and trying to process everything that happened this night.
A/N: I know it cut off kind of quickly there, but I figured this chapter was getting too long. I already have ideas for the next two chapters. Review?