Based on a Milady/Milord Ficcy Friday prompt from butterbadger

It was happening again. As per usual, Annie was finding ways to get out of sex. And this one wasn't even original.

Once Jeff started to get his hands under Annie's shirt, she looked at her watch, called out "Look at the time!" and explained that she needed to go home and sleep. She claimed Troy and Abed needed her to get up early and be their script woman tomorrow – which was the same excuse she used the second time Jeff made his move. She wasn't even trying to come up with new excuses anymore.

It had been three months since Jeff admitted he wanted to be with Annie, and everything was going good since then – except this part. Every time they made out and Jeff tried to get a little more from Annie, she backed off and made up some excuses for stopping. But the excuses were getting worse, and Jeff was getting more frustrated and downright confused.

In the past, Jeff wouldn't have put up with this for more than a week. Two weeks was his previous best waiting period. But he had put up with three months of having no sex with Annie – not to mention the already painful three years of buildup beforehand. If he was going to keep enduring this, he had to know exactly what phobia, neurotic quirk or paranoid thought he was dealing with.

"Okay, what is it?" Jeff finally asked straight out, as Annie got up from Jeff's couch and tried to straighten herself up. "What phobia, neurotic quirk or paranoid thought are we dealing with here?"

"Huh?" was all Annie could get out. "I, um, don't know what you're talking about, Jeff. And I have script woman duties to think about anyway." Yeah, that told Jeff he was way off base to suspect something.

"Come on, what's the problem? Are you still too hung up about…..sex?" Jeff asked in an Annie-like whisper to try and lighten the mood. But Annie just gasped like usual instead of laughing, so maybe he wasn't entirely on the right track. So he got more reassuring by saying, "I think I've seen enough role playing games, Christmas songs and paintball wars to know you're on the right track."

"Jeff! That has nothing to do with anything," Annie stammered out.

"Okay then, that rules one theory out," Jeff crossed out. "So if it's not that you don't know what you're doing….then I know too much, then?" he guessed, then actually smiled a bit when Annie didn't answer. "I see. Well, luckily I've had that effect on a lot of – people," he stopped before he started bragging about his past conquests, at a worse time than usual. "But that means I know how to get around that, you'll be fine!"

"Jeff, you don't have to push this," Annie insisted more firmly.

"Annie, I'm pushing this for you," Jeff reminded. "You've been too nervous to even sleep with me since we got together. If there's some serious hang-up you have, I want to help you get past it. And not just to snap the longest drought of my sex career! I mean, we're in a relationship now, and I pretty much have to-"

"I know this isn't real, Jeff!" Annie blurted out. Why the hell she did was another very confusing matter. Jeff certainly couldn't think of anything for a good 10 seconds.

"Annie….have you been getting funny dreams from watching 'Inception' again?" Jeff inquired. He thought Abed agreed not to play that movie while she was in the apartment anymore. But it appeared Jeff had to alter the plumbing for Abed's mini-Dreamatorium 2.0 after all.

"No, Jeff, I know we're not in a dream within a dream within a dream this time. And I only had that nightmare and believed it for one morning, okay?" Annie clarified. "Okay, maybe real wasn't the right word after all. What I meant was….I know this isn't a regular, serious relationship. So you don't have to pretend it is."

Jeff had no idea how it got to that topic of conversation. So it was probably best to clear up his old questions first, before he took on these new weird ones. "What does anything about that have to do with not wanting to sleep with me?" he tried to ask with a level head.

"I'm going to get to that," Annie promised as she seemed a little nervous now. This was pretty damn fitting at this point of the conversation/budding argument.

"So get to it, if it's not too much trouble," Jeff pressed, unable to contain all his rising snark/annoyance. But he tried to keep it in check while Annie was explaining herself.

"Jeff, I'm not getting carried away about what this is. I did assume things about what we could be once, but I can't do that anymore. We're not some fairy tale romance, and that's all right with me now. So I'm just taking this for what it is before it ends someday," Annie stated, although she wasn't exactly clearing things up yet.

"And what exactly is this?" Jeff asked. "I remember saying a few months ago that I wanted a relationship with you. Unless one of us heard me wrong, I don't see the confusion here."

"But you're not a relationship kind of guy, Jeff. It took me a while, but I got the message," Annie assured. "I don't have some romantic dream that you'd change your lifestyle, change your thoughts about couples and marriages, and stop telling people to nut up and die alone. " Jeff nearly chuckled at Annie using the word "nut" in a dirty context without blushing, yet he was still too confused and annoyed at her.

"You have relationships once in a while, like this one. But you don't believe in settling down and committing for the long haul. And if I tried to change that, this whole thing would be ruined and we wouldn't even be friends anymore. So I'm not going to," Annie promised, as it started to dawn on Jeff where she was going with at least 10 percent of this.

"This is just a casual relationship that'll probably end before we graduate and go back to the real world. Since I know that, I can let myself have fun until you end it, or we end it together, and we can still be friends later. That's sure better than the alternative," Annie figured.

Jeff couldn't figure that much, yet in his struggle, he remembered a still unanswered question. "So you won't have sex with me unless we're in a real long-term relationship? Annie, even for your new devious side, that's a low blow. And I'm less inclined to mean that in the dirty way now!"

"No, no, that's not it!" Annie cried out. "I'm afraid to have sex because it'll make me forget everything I just said! I'm afraid it'll make it harder for me to lose you later! And there's nothing dirty at all in that, Jeff!"

There may not have been anything dirty, but the odd, sad and somewhat insulting stuff was still there to make up for it. "You mind going a little deeper into that?" Jeff said, not even bothering to clarify his proper context for the word "deeper."

"Jeff, I know how to have sex with you by now. I know it would be incredible, and you'd go all out to drive me crazy. But it might be too incredible. You'd be the first man to ever show me how great sex can be, and that might make me too happy. So much that I forget it won't last forever. At least until it actually ends," Annie predicted.

"Well, if that's the case, fine! 50 percent of the Winger touch is still better than 100% from everyone else! I can go down to 40 percent, but that's as much phoning in for sex that I'm comfortable with," Jeff offered.

"Jeff, that's not helping!" Annie insisted. "I already know that's the one thing you really put an effort in! If I let you do that….it'll just hurt more later."

"And later is what again? When I dump you, like I haven't done yet except in your mind? Do I have that right?" a more annoyed Jeff countered.

"I know you're not going to dump me yet!" Annie shared. "I figure it'll happen after graduation, or after we try and fail to make it work a few extra months. Either way, once it gets real, I know that'll be it. And once we have sex, it'll start getting real. Then it'll be all downhill from there. I mean, by then, what's left for us to really do?"

"So you think I'll just have my way with you, then get bored and dump you?" Jeff tried to understand – then moved onto getting angrier. "You actually think I would do that to you?"

"Oh come on, you bragged about doing that to women all the time!" Annie reminded.

"That was other women, you're you!" Jeff stated, although holding Annie up on a pedestal even while yelling at her was a steep contradiction. "Why do you think I'd be that awful to you?"

"It wouldn't be the first time. I mean, you'd be having sex this time instead of kissing me before summer. And you probably wouldn't stay away from me for the next three months this time," Annie finished comparing. "But after dating me, kissing me, having sex with me, seeing me naked….there isn't much more you could do before you got scared off. I thought the longer I put off the sex, the longer we could enjoy ourselves before we tanked afterwards."

"And we're back to you being so convinced we'd tank," Jeff attacked, if only to do something other than forget that summer. "So you thought withholding sex forever would stop that?"

"No, Jeff, I was going to do it, I promise! Just after a little while longer, that's all!" Annie promised. "Just until I had a bit more fun doing other stuff with you. Then once we finally had sex, I could live with things falling apart from there. And contain the damage to save our friendship."

"Funny how I'm the only one doing the damage in this fantasy of yours, isn't it?" Jeff cut in.

"Oh, I know it won't be all your fault! But I'm sure I'll do something to make you afraid at some point, whether I mean to or not!" Annie predicted. "Jeff, I'm not attacking you for it! I understand you don't want to be with someone for a long time! I didn't let myself understand it before, but I'm not that naïve schoolgirl anymore! I just want to stretch this out as much as I can before we've both had enough."

"Sounds like you're the only one that's had enough here," Jeff shot back. "You know, I have jumped through a lot of hoops to get out of relationships. But you're shattering my world record and then some here!"

"Why are you mad at me? I'm giving you an out for the future!" Annie reminded. "You don't want the trouble of something real, and I'm trying to spare you!"

"Maybe I don't want to be spared the trouble," Jeff admitted before he caught himself. But soon enough, he realized he'd have to elaborate.

As awkward and somewhat lame as the rest of this would make him, he felt like he had to go on. After being told over and over that he would feel scared or smothered by Annie, it was time to get some facts into this.

"Maybe I want the trouble," Jeff stunned Annie by saying. "I haven't wanted the trouble in just about ever. But with you, it doesn't seem so….troubling."

"Jeff, you don't have to spare my feelings here," Annie disclosed. "I don't want to nag, guilt or manipulate you into saying something you don't mean. Or to do something you don't really want to do. Or think you want to say or do now, but regret later. I'm not that kind of person anymore, you can be fully honest with me."

"I am being honest," Jeff laid out there, without letting himself do any second guessing.

"Come on, Jeff, you're the most anti-commitment person in this state!" Annie low-balled. "And you've only officially dated me for three months! Why would you mean that you actually wanted a real future with me?"

"Because I love you, okay?"

Now that really got away from Jeff.

Yet within three seconds, he realized he really regretted it not because of what he said – but because he didn't want to say it like that. Certainly not during an argument.

He had seven more seconds to take that realization in before Annie spoke up. "That….is a low blow, Jeff. You don't have to say that to win this argument."

Now it was back to being mad again. More mad than ever after that, actually. "You think I said that to beat you? Annie, I've never said that to a woman in my life! Even the ones I've seen naked! Do you think I'd say it now if I didn't mean it? This is real Jeff you're talking to, not the evil fantasy Jeff you've turned me into!"

This did manage to take Annie back a bit. Yet she tried to recover by saying, "Jeff, I'm not trying to make you evil. You've said for years that love and relationships and couples and being with someone is a waste of time. I didn't believe you meant it then because I was naïve! Now I finally believe you! Didn't you want me to be more grownup and not so oblivious anymore?"

"Not like that, I didn't. I wanted you to be grown up and still believe in that stuff. I didn't know I killed that part of you that much…." As his familiar Annie guilt started kicking in, Jeff willed himself not to dwell on it until the argument was over. With that, he got back into defensive, offended mode.

"Second of all, you're basing all this on the old Jeff! Jeff since three months ago is different now! He does couples stuff now and he likes it! He goes on dates, doesn't need sex all the time and actually treats his girlfriend like a princess! But that's not enough for you, is it?" Jeff accused.

"Well, um…." Annie regrouped. "Well, how am I supposed to know that? That just proves you're good at taking me out! You're no good at that in the long term, you've made that clear for years!"

"That doesn't mean I don't want to try! And I've never wanted to try with anyone until you!" Jeff pointed out.

"How am I supposed to know that for real?" Annie countered, halfway proud that she wasn't thrown off her argument – while her heart still halfway fluttered in her chest. Yet she didn't want that to get the best of her, so she pressed on. "You don't have the best record on being clear with me! Believing in some romantic you has hurt me too much already! And you still never apologized for doing that so many times, either! So forgive me if I'm a little skeptical, Jeff!"

Jeff just stayed quiet for several moments, then responded quietly. "You don't believe in me. You don't think I can change. You still think the sooner I have sex with someone, the sooner I'll lose interest and end things when they get real. That was the old me….but I haven't done any of that in a long time, Annie. But you're judging me for who I was then, not for who I'm trying to be now!"

Now Jeff was in full on righteous anger mode, although he wasn't full on out of control as he continued. "You're the one person who always believed I could do anything. That's the biggest reason why I'm even close to being a good boyfriend now! But if you're still convinced I'll relapse, how do you think that makes me feel? I want everything with you, Annie, or at least I want to want it! But how am I going to do that if you don't believe I can? Or if you're trying to tell yourself you don't?"

Jeff just wanted this to be over with, before he said something he would truly regret – or before he made Annie so upset that this dragged on all night. She just looked stunned and taken aback, so he figured he had room for one more closing remark. "I expect to be judged like that by Britta, or Pierce, or even Shirley. But you….if you don't even have faith in me, then…."

There was no way to continue that thought without being really hurtful. So in another example of how Jeff really was changing, he just stopped there and headed to bed. He shut the bedroom door, trusting that Annie would show herself out and let them both cool off until tomorrow.

Jeff didn't hear anything, so he figured he could go to sleep and shut this out for a while. He changed into his perfectly ironed bed clothes and made sure not to get a wrinkle on them when he laid down. He then tried to go to sleep, but it wasn't really working.

He still thought about how Annie didn't believe he could be a serious boyfriend, or didn't want to believe it. Then again, he really gave her no reason to think he would be before now. But he thought acting like a real, committed boyfriend for three months would have told her different already!

Then again, Annie wanted actions and words, without any wiggle room to doubt them. And three years of doing the opposite for her couldn't quite balance out three months.

At that distressing thought, Jeff heard the door to his bedroom open. He knew who it was, but kept his eyes closed, in case Annie came to yell or do some other troubling thing. He stayed still and kept his back turned to the left, yet almost opened his eyes when he felt Annie sit behind him on the bed. He did finally open his eyes when he heard her lie down, then saw her right arm reach over his waist and come into his view.

Jeff saw Annie's hand tentatively search for one of his, yet could tell how hesitant and nervous it was – or rather, she was. It must have said something that he could read Annie's thoughts, nerves and regret just how looking at her hand.

But he took mercy and let his right hand gently touch hers, then let it slowly slip into his. Her thumb still glided slowly and uneasily over his skin, yet Jeff let her get comfortable and reassured before she finally relaxed.

"I'm so sorry, Jeff," he heard Annie say while lying behind him. "I….I just didn't want to get carried away like a child again. But I guess I went the other way. This time I really did see things in you that weren't there, huh?"

"No. You didn't," Jeff admitted. "I did make a good case for you to think that way. And I'm sorry for that….and all the other stuff. I always have been."

"I know. Or I liked to think that I knew," Annie voiced behind him. "Now I know for sure, so thank you."

"Well, here's more stuff you should know. Just so we're completely on track now," Jeff started. "A lot of me does still think real relationships are lame. But I don't want to believe that'd be true with you. I thought I was making that clear before, but just in case…."

Jeff swiped his thumb over Annie's hand and focused on it, as he willed himself to get into sappy mode. "I want to want a real future with you, Annie. I mean, we've dated for three months, but I've had some form of deep feelings for you for just under three years. And I've admitted it to myself for about a year. That's long enough to know I want that long term stuff with you. I'm just not sure I can give it to you, even if I try. And if you don't believe I can do that anymore, how can I?"

"Jeff, I do believe it, I do! I've always believed in you! With a few glaring exceptions, obviously. I just….I just wanted to make sure I'd be okay in case you couldn't. And that we could still be okay too," Annie explained.

"Well, maybe now I can help you be okay in other ways," Jeff offered. Annie didn't say anything, but when he felt her kiss the back of his neck, that seemed to be an answer.

"I think that's better than the alternative," Annie concluded. "I really am so sorry, Jeff."

"Annie, it's good. We're good," Jeff assured, trying not to sound dismissive. He rubbed her hand again to calm her further, promising, "Now that we're on the same page for the first time in three-and-a-half years, I think we're going to be fine."

"Finally," Annie exclaimed, which made Jeff chuckle for reasons he didn't entirely get.

Jeff didn't turn around to face Annie, or kiss or try anything else with her although they'd made up. He just settled for holding her hand, stroking it, and batting their fingers together playfully for no real reason at all. This actually entertained them both and soothed them as they drifted off, with Annie snuggled against Jeff's back and her arm draped around him.

It was almost hard for them to remember that this started because of sex, since it led into much deeper issues. Yet the end result still came full circle.

For the very first time, Annie Edison actually slept with Jeff Winger that night – even if they didn't "sleep together." And for the very first time, Jeff actually slept with a woman without making a move on her, and without any intention of having sex that night or afterwards.

Combined with how Jeff said "I love you" – which would have to be fully addressed another time – this was a milestone night in ways Jeff didn't anticipate an hour ago. But he knew just enough about being a good boyfriend to know that wasn't a bad thing. Not at all.

With that, any other milestones on the backburner could take their time now.

A/N 2: Jeff's "trouble" lines are mostly taken from "How I Met Your Mother"'s fourth season finale, when that show's own womanizer in great suits made a love confession.