TRIGGER WARNING: Drug abuse/alcohol abuse and dub-con.
A/N: Written for an anonymous prompt at the Milady_Milord LJ Comm kink meme.

Annie's dealer had told her to meet him here, a rundown bar called L Street, and she had been desperate enough to agree. She had two papers that were due next week and while she had completed first drafts for both, she wasn't particularly confident in them. Worse, she had a presentation in three days and she was having trouble memorizing the slides. Hours of practice wasn't helping either and Annie needed to focus. So there she was, just before midnight, in a sketchy alleyway, hoping beyond hope that her dealer would remember making the appointment and show.

Another 15 minutes passed and Annie couldn't help but check her watch. It was hard not to watch the clock and wonder if her mother had realized that her daughter was nowhere to be found. Annie was the perfect daughter, it was doubtful she would even think to look. Annie was drawn out of her contemplation by noise at the edge of the alleyway. She burrowed deeper into the shadows, wary of any drunken strangers approaching her.

"Anna, whatever your name is, you here?" Annie started forward when she recognized her dealer's voice, hurrying to make sure he didn't leave.

"Yes, yeah, I'm right here." She waited until Mark produced the Adderall before pulling out her money. He never remembered her name but he seemed to have a soft spot for her because he had warned her, at the end of their first meeting, to quit pulling her money out before she knew her dealer had what she wanted. Good way to get robbed or worse, Mark had warned, muttering about her cardigans and something about his kid sister. He handed her the pills and she handed him the money, smiling briefly, as he counted the bills then nodded at her. He stuck his hands in his pockets and stared at her for a minute.

"Get out of here, okay? I shouldn't have set up a meeting here, isn't safe for a chick like you at this hour. You need a ride or anything?" He seemed slightly uncomfortable as if the idea of giving someone a ride was a foreign concept, grimacing immediately after making the offer. Annie shook her head, smiling in thanks.

"It's okay, I'll be fine. I'm not that far from here." Annie silently amended her statement, she wasn't far if she was driving. Unfortunately, while she was pretty good at sneaking out of her house by now, stealing her mother's car was still beyond her means, so Annie had walked three blocks and caught the bus. She hadn't considered that her dealer would be late and the buses would no longer be running. She waved at Mark as he shot her one last glance before disappearing into the dark. Annie could feel her nerves fraying, the anxiety mounting, and she realized that she had the immediate answer in her hand – getting home would be easier once she was calmer. She dry swallowed two pills and leaned back against the cool brick, waiting for the ever so slight tremors to stop, the calm to kick in.

Jeff walked out of the bar, stumbled really, and steadied himself against the wall. He was regretting, just a little, turning down the offer from the gorgeous blonde in the bar. But he could get laid whenever he wanted, tonight had been about getting shitfaced in peace. It might not have been his brightest move to go to his regular bar but he had wanted to keep his options open in case he changed his mind. He moved further into the alleyway wanting to avoid the prying stares of strangers and bumped into something. Make that someone. He reached out to steady them, quickly realizing it was a her. A charming smile slid across his face without a second thought though she likely couldn't see it in the dark.

He looked her over, as much as he could see, and realized she was young. She looked like she'd had a few so he figured she was around 21. Maybe 19 or 20 and in possession of a fake ID. She wasn't his usual type, if he had a type at all, but Jeff was a connoisseur of women and in a few years, when she grew into herself, the hormones levelled out and she invested in good hair cut and started following an extensive facial care regimen, she would likely be stunning. He smirked. He might prefer to sample the finished product but he'd been known to taste-test during the cooking process too.

"Excuse me, miss? Are you okay?" Annie was jolted out of her blissfully worry-free existence by the most beautiful man she had ever seen leaning over her. He asked her a question as he leaned in further, but all she could focus on was how good he smelled. She moved closer, attempting to find the source of his spectacular scent, and his hands moved to her hips involuntarily. She was pressed right up against him and she could feel every inch of his body.

Jeff revelled in the feel of her pressed against him and lifted her enough to line up their mouths. Kissing her was like a blast into the past. Enthusiasm and a full-speed-ahead attitude confirmed her youth. She was sweet, bubblegum lipgloss flavouring everything, and showed no hesitation. Her tongue tangled with his immediately, their kiss moving beyond the tentative stage within seconds. Surprised, but not at all put off with the quick pace of their encounter, Jeff pinned her higher against the wall and her legs fell open to cradle his hips.

Annie could feel the man in front of her, hard and pulsing, against her core and she made up her mind instantly that just this once, she was going to seize the day, live in the moment! She was 18, legal age, and she wanted this. She wanted this attractive man, who didn't know anything about her, to fuck her against the wall in an alley. She wasn't a bigger girl here, she wasn't a nerd here, she wasn't a disappointing daughter, she wasn't friendless or covered in acne. Right now, she was just some girl that he wanted to have sex with and given how good he was making her feel, Annie had no reason to turn him down.

"What's your name?" Jeff managed to grunt out his question even as he ground against her centre, and felt her entire body shiver against his. He already knew she would lie to him but that was okay because he was planning to lie to her too. Having sex in an alleyway with a strange wasn't about being honest.

"Ann-Anna. Yours?" Her eyes opened just wide enough for Jeff to see a clear blue, darkened with lust, before they slid closed again.

"Jay. Just call me Jay." His hands snaked under the skirt she was wearing, stroking over her underwear before slipping inside. His fingers moved against her clit until he felt her hips start moving and then he decided it was time to find out just how tight she was. He continued pressing down on the bundle of nerves with his thumb as his middle finger slowly pushed into her. She was wet and warm and so tight, Jeff wasn't sure this would be fun for her at all. Her hips kept moving restlessly against his hand, though, so he guessed she was on board. He pumped in and out for a few minutes, his mouth attached to her neck.

"Jay... Oh god, Jay, please." Annie couldn't help but ask him for something but for the life of her, she couldn't name exactly what she wanted. She felt his hand under her skirt leave her and she whimpered. Okay, whatever she was asking for, him removing his hand was the opposite of she wanted. Her hands which had been skimming through his hair and scratching against his chest attempted to grab his hand and bring it back under her skirt.

"Give me a sec, I promise, I just need to grab-" Jeff extracted the condom from his wallet triumphantly and began undoing his pants with his free hand, condom stashed safely in Anna's cleavage. Freeing himself, he put the condom on and returned his fingers to their previous work. Anna shuddered against him and he smiled as he kissed her, lining their hips up. He entered her in one thrust and she stilled, making him pause. "You good?" She waited for a few minutes and then nodded.

He rocked against her and dipped his head to her breast, pulling her top low enough to see her lace covered nipples. He watched her nipples harden at the cool night air before taking one in his mouth. One of her arms moved to anchor his head against her chest as the other splayed against his chest, brushing his pecs and causing him to twitch at the inconsistent sensations.

Annie didn't even take a moment to consider that she was no longer a virgin. If sex was always this good, it was no wonder everyone had lost their v-card ages ago. She had heard it hurt, losing your virginity, but so far, between Jay's fingers, his tongue at her breast, and his cock inside her, it had been so good. It had felt strange, when he first pushed in, but now it was just rolling waves of pleasure. Every time his hand brushed against her clit, every time his tongue and teeth pulled at her breast, every time his dick pushed back in.

"We'll meet at L Street for 9. How does that sound?" Jeff's question gets mostly non-verbal responses. Britta is nodding and making plans to crash at Troy, Abed, and Annie's place. Troy had flashed a big smile and two thumbs up at Jeff before turning to Britta and assuring her that she could spend the night in the blanket fort with Abed and him. Abed had given his standard, 'cool, coolcoolcool' before joining in the conversation between Troy and Britta. Shirley had waved excitedly as she hurried from the study room to make arrangements for a babysitter. Pierce had given a nonsensical dismissal that fooled no one before harrumphing and following Shirley out. Only Annie had yet to acknowledge his proposal. Jeff watched her with concern before sitting down.

"Excuse me, miss? Are you okay?" Jeff smiled gently and leaned forward to nudge Annie but before he could, she turned a stunned gaze on him, clear blue eyes dark with shock. Jeff felt a frisson of unease skitter down his spine, like a mind-blowing revelation was on the edge of his consciousness. "What? Annie, what is it?" His whispers were low and urgent, not wanting to attract the attention of the study group.

"Jay?"