Wow, it's been a long time since I've posted a story, hope I'm not too rusty! Heads up, this chapter is a hard T, but it will be the most inappropriate chapter in the entire story.

DISCLAIMER: If I owned Community, Troy and Annie would have at least kissed by now. I mean, c'mon.

September 2nd, 2011: The Night it All Changed

You're welcome... and I hate you...and I wanna have your children.

-Annie

8:43 P.M.

"Can you come over? Jeff just broke up with me and I don't know what to do. I just need someone to talk to. Please?"

Troy blinked and looked at his phone in confusion. Why was Annie calling him and asking him to comfort her? Why not ask Britta or Shirley? And, probably the most important question: Why did Annie want him to come over to her apartment?

To most males, one answer would immediately come to mind and they would rush over there, excited and hopeful. But Troy wasn't very smart, and he assumed that Annie just wanted to talk. He felt sorry that Jeff had broken up with her, especially because their relationship had seemed so serious.

Jeff and Annie had started dating the week after school had ended, even though it turned out that Jeff and Britta had been friends with benefits for most of last year and Annie and Abed had made out a few days before school had ended. Jeff and Annie definitely had chemistry and decided to finally give dating each other a shot, and it had seemed like things had been going well.

Apparently not.

"Troy? Are you there?"

"Yeah."

"Are you coming over?"

Troy hesitated. For some reason, his mind was screaming 'bad idea!', but he did want to see her and comfort her. Ever since Jeff and Britta had made Troy realize how 'much of a woman' Annie was, Troy had had some feelings for her. Okay, so they were mostly just feelings of the sexual nature, but every once in a while he would catch himself noticing how pretty her smile was, or how cute and dainty her feet were (Troy was an odd person, so it should come as no surprise that he noticed characteristics about someone's feet). He liked her. He didn't want to be in a relationship with her, and he wanted to have sex with her, but he didn't want to just have sex with her. He wanted to stay really good friends with her if they did have sex, because he loved her as a friend more than he liked her as a woman or a sexual object.

And if that meant not sleeping with her so that their friendship would remain the same, then so be it.

"Troy?" Annie's voice had taken on a pleading tone.

Troy wanted to be there for her, even if it was just as a shoulder to cry on, because Troy was in love with Annie, even if he didn't realize it yet.

Man, feelings are confusing.

"Yeah, I'll be right there."

9:02 P.M.

As soon as Troy opened the door, Annie flung her arms around him with such force that he almost fell backwards.

"Whoa, calm down." He said, patting her back gently.

"I'm sorry; I'm just a mess right now." Annie said, smiling meekly as she walked to her couch and sat down.

Okay, Troy, here's what you're going to do,. His mind told him about his carefully thought-out plan. Well, as carefully as plans are thought out when they take place in Troy's mind. You are going to talk to Annie, comfort her, and then try to cheer her up. Then, when she seems fine, you are going to leave without having sex with her. If she falls asleep, you are going to carry her to her bed and not have sex with her. If it's really late by the time you guys are done talking, you are going to drive home through a bad neighborhood in pitch-blackness because you are not going to have sex with her. You got that? Troy nods at his own thoughts. Okay, good.

"Um, Troy? You can sit down if you want." Annie said, looking at him in confusion.

"Oh, yeah. Cool." Troy said, taking a seat next to her. He looked at Annie and realized two things at the same time:

1. All she was wearing were a tank top and shorts.

2. She was drinking wine.

Troy decided to focus on the latter, as to not stray from Plan DHSWA (Don't Have Sex with Annie).

"Aren't you underage?" He said, gesturing to her wine glass.

"Yeah, but it's no big deal. I've had wine before." Troy nodded. It really wasn't a big deal. After all, he'd had wine before he was 21, too.

"Do you want some?" She asked.

Troy shook his head. He knew how alcohol clouded judgment, and he had a plan to stick to.

"Okay." Annie said, shrugging.

They sat in silence for a few seconds.

"So..." Troy said, unsure how to bring up the subject. "About Jeff..."

"Jeff!" Annie wailed suddenly, burying her face in Troy's shoulder.

"It's okay, Annie." Troy said, smiling as he stroked her hair. This was nice, just stroking her hair. Totally innocent. It didn't even cross his mind how her knee was on his thigh or how her chest was pressed up against his arm or-

Damn.

Annie lifted her face from his shoulder. "I thought he was the one, you know? We had so much in common and we got along so well. I just don't know where it all went wrong." She said, her eyes watery and doe- like.

Troy's expression softened. "So you don't know why he broke up with you?"

Troy mentally kicked himself. That was probably the total wrong thing to say to someone who was on the verge of tears.

"Ummm..." Annie blushed and scooted away from Troy. "I kinda do."

"So what was it?" Troy asked.

Annie bit her lip and poured herself another glass of wine. Troy hadn't even realized she'd finished her first.

"Okay. He broke up with me because..." She wouldn't meet his eyes. "...I wouldn't have sex with him."

Troy raised his eyebrows. "What?"

"He was really patient at first! He was like 'I'll wait until you're ready' and stuff like that, but then he was all like 'C'mon, we've been dating for two months! What's stopping you? Aren't you attracted to me?' Which led to this huge fight and when I still said no he broke up with me." Annie finished, looking down and picking at a thread on the couch.

A few more seconds of silence.

"Okay. Well it's good that you didn't give into that kind of pressure." Troy said, not really sure how to handle the situation. Annie smiled, looking happy with herself. "But, and I know this question is really personal and stuff so you don't have to tell me if you don't want to, but... why didn't you want to have sex with him? I mean, I'm straight, and even I know that Jeff's a hot dude, so why not?"

Annie blushed even harder and took another sip of wine. Well, more like gulp of wine. She was almost done with her second glass, and if Troy hadn't been so caught up in this newfound fact about Annie and Jeff, he probably would have been concerned about her level of alcohol consumption.

"Um, well... I've kind of never had sex before." Annie admitted, finishing the last of her glass and pouring herself a third.

Troy's eyes widened in confusion and surprise. "But what about your high school boyfriend? You know, that gay dude."

Annie probably should have been surprised that Troy knew about this, as she'd only told Britta and Shirley, but she wasn't. It was common knowledge in the group that if you told even one person about something, there was a good chance that the whole group would find out unless you specifically said not to tell them about it. Your chances were doubled if you told two people. Tripled if you told Shirley.

"I only said that we'd had sex before because Britta and Shirley were laughing at me because I've never seen a you-know-what before."

"And you never had sex with Vaughn?" Troy asked.

"No. I mean, c'mon. Who wants to lose their virginity to Vaughn? He's a stupid hippie. With no nipples." Annie giggled. "Hehe. Nipple-less hippie."

Annie was acting buzzed, and Troy notices that she's almost done with her third glass of wine. He wonders how many glasses she'd had before he came over.

"So you're a virgin?" Troy asked slowly, trying to let it all sink in.

She nodded.

They sat there in awkward silence for a few minutes.

"So, um..." Troy said uncomfortably. "I should probably-"

And before he could even react, Annie had flung one of her legs across his lap and was kissing him.

Troy pushed her away from him. "Annie! What are you doing?"

Annie flushed with embarrassment, but didn't let her confidence falter. "I want you to be my first, Troy. That's why I called you over here."

Troy looked at her blankly for a second, and then it sunk in. "Whoa! Really?"

Annie nodded.

Troy was faced with a dilemma. On one hand, he'd made a promise to himself that he wouldn't do this. On the other hand...

He really, really wanted to have sex with her. And here she was begging him to!

Okay, Troy, think of the consequences. If you do this, your friendship will probably be ruined forever. Shirley and Jeff will hate you. Abed might hate you, too, because he made out with Annie and you didn't even ask him if he was okay with this. Well, it probably would have been awkward if you'd asked, but still, you should have. Crap, this wasn't working. He still wanted to have sex with her. Okay, what would Shirley say if she found out? Troy, I can't believe you've done this. You took advantage of poor little virginal Annie when she was in a bad place. How dare you? She was probably saving her virginity for marriage. And there are millions of other women in the world that you could have committed that sin with if you had the urge to do so. Troy, you have lost our trust forever and you're out of the group. Troy didn't want to be out of the group. Okay, he could refuse Annie. He could do this.

"Annie, I can't have sex with you. I'm sorry, but if we do this, things will never be the same between us. It will get all awkward and then we won't be able to be friends anymore."

Annie's face dropped. "Okay, Troy, I didn't want to resort to desperation, but..." She took a deep breath. "Please, Troy. I want you. I want to touch you. I want you to touch me. I want you. To have sex with me. Right now." She said.

"Umm, I, uhh..." Troy was at a loss for words. He closed his eyes and weighed his options. Option 1: Run out of her apartment, drive through an awful neighborhood in the dead of night, and have your friendship maybe ruined anyway even though you didn't have sex because you still had this awkward conversation, or Option 2: Finally have sex with the hottest girl on the planet, who is begging him to do so, and who he just found out is a virgin, which, let's face it, makes her that much hotter. Well, then again, everything makes Annie hotter.

Troy hears a shuffling sound, and when he opened his eyes, Annie had taken off her tank top. His eyes widened.

Speaking of things that make Annie hotter.

"Annie, uh, I..." He said, his defense weakening as Annie is nearly topless. "I-I can't do this... I have to...go."

Troy starts to get up (which is difficult given his current 'state'). "I-I'm rea-"

In one swift move, Annie grabs his hands and cups her breasts with them.

Troy lets out a strangled cry. How many times had he imagined this happening? And here he was, right now, touching her boobs. Three-months-younger Troy would probably high- five him if he was here right now. Well, if that was possible.

No, Troy. You aren't going to do this.

He looks at Annie's wide eyes, looking right into his.

Aw, damnitt.

Troy moves his hands down to Annie's hips and lifts her up, and she immediately wraps her legs around his waist. They start kissing passionately as Troy runs the 10 steps to Annie's bed, neither thinking about the consequences that the next morning would bring.