Annie breathed more normally than she had expected, as she waited for Jeff's answer. After two weeks of anxiety to get her plan this far, she was starting to get immune to nerves. Of course, one statement from Jeff could still throw her off, like it usually did.
"What….what do you mean, where do we go?" Jeff asked. So he was still going to go this route, then. Well, not after all Annie put herself through, he wouldn't.
"I mean that we've done….private acts because of each other, and we both know it. We can't just reset that, can we?" Annie mistakenly asked as a question that Jeff could still say yes to.
"How….how did you even know about my private act? There's a reason they're called private, you know." At least Jeff wasn't denying how this started, but the deflecting tactics were still there. So Annie still had some work to do – which meant she'd have to lead by example.
"I'm going to assume you didn't see me work outside the study room before you….got to work. I was too busy to notice you too, at least until I heard you call out my name." Witt that, Jeff slipped into his 'ashamed for being a dirty old man' face, which probably wouldn't be helped by the rest of the story – at first.
But Annie had to get it out of the way anyway, so she went on. "I figured out that I had to….make us even….about a few days later. It took me about 10 days to practice doing what I did last night, though. I mean, it took about five days before I made myself….finish in my room while Troy and Abed were outside! Then when I did it the next four days, I figured I was ready to do it with you out there."
"Wait, so you really planned last night all along? You entrapped me?" Jeff exclaimed, trying to brush past the entrapment term – and how the movie "Entrapment" had a couple with even greater age differences. But Jeff was more Bond Sean Connery than "Entrapment Sean Connery" while Annie was far more devious than Catherine Zeta-Jones ever could be. Jeff stopped before he wondered if Annie was as bendable as Michael Douglas's future wife was in the movie – and now he had another old man/hot young woman couple to block out.
"Come on, you really thought I didn't hear you open the door and breathe funny?" Annie exclaimed. "I was much better at keeping my moans quiet, by the way. I'm just glad I kept looking at the ceiling instead of catching you, or I'd have cracked up before I went off!"
Jeff was reeling enough without Annie talking about….these subjects without blushing or stammering. What the hell had he created? Then again, he didn't make her watch, or want her there to watch, or set him up to look even more depraved for revenge! Because that was what this had to be!
"So you put yourself on display for me out of revenge? Troy and Abed never had a noisy project that drove you out, did they?" Jeff argued.
"I may have oversold how noisy it was," Annie answered. "Don't worry, I didn't tell them why I was coming here – I mean, why I wanted to stay here! Abed made some guesses, but even he can't get everything right."
"Good, at least one of us is still sane." Jeff declared. "I mean, I clinched my spot on a dozen sex offender lists, and you finally caught my pervert disease. Lesson learned, okay?"
"You think that was the lesson here, Jeff?" Annie protested.
"Even if it wasn't your lesson, what else could it be?" Jeff responded. "My mighty Winger made you go from a prude into my dirty fantasy, just to get back at me! And you said it took two weeks to get ready for it? That says something about me corrupting you and making you miserable….somewhere."
"Jeff, I know for a fact you didn't forget my Dungeons and Dragons routine, my Santa suit or my paintball outfit. They must have rattled around in your fantasies somewhere! If you do remember and you still think I'm that squeamish about sex, then it's the dumbest lie you've ever told me," Annie reminded. "Granted, masturbating with Troy and Abed in the apartment and then doing it last night was…..challenging. But no matter how nervous or sick or grossed out I was, even with the tissues, I got through it! And that's the lesson I was teaching here!"
Annie started to breathe shaky again, since this was the make-or-break speech of the plan. But she was composed enough to at least get started. "Jeff, it wasn't just fantasy sex that got you off in the study room. I heard you say all those things about my eyes and beauty and 'if only.' Even I know you don't usually get that sweet when you're finishing yourself! Not if it was only for sex stuff."
Paragraph one looked to be a success, which emboldened Annie going into paragraph two. "You want something more, but you're too scared to actually take it. So you're stopping yourself by doing….stuff like this so you don't do it for real! I know the usual reasons why you don't want it for real….stuff like my age and how I can't handle you or how gross you are, or handle adult relationships in general. Well, I saw you jerking yourself to me in a very adult way and I didn't freak out like a child! In fact, I faced some of my old childish sex hang-ups to make us even! What does that tell you?"
"That you changed yourself to be 'more adult' for me. I'm sure regular you and Britta and Shirley can lecture me on why that's wrong. But I already know it should make me guilty because…..well, you're already wonderful the way you are." Okay, Jeff threw Annie off a little bit on that one. But he did help her segway into paragraph three, at least.
"And you're amazing the way you are, too. That's why you shouldn't have to go this far to hide how you feel about me. And you shouldn't think I can't handle you, because I can….even if it's gross stuff like this! If I can go out of my comfort zone to….do that stuff, I can do it for anything else in a relationship! And you already know if there's something I don't know, or some problem I want to solve, I don't rest at all until I figure it out! Especially if it's important to me or it involves someone I care about, and you're both those things!"
All right, big finish time….good time to remember that being stubborn part before the nerves get away….
"I know you should be the one trying to win me over, and that masturbating doesn't mean we'll work out. But we don't have to handle these things by ourselves…. I mean, we can if we have to, but it's easier with someone's help." Annie then got sidetracked when she realized her accidental innuendo. "Not that the things we have to handle are genitals, I mean….well, you know! No wait, you don't….then I meant we can handle emotions and relationships and our differences! Those things….and the sex things too, but that can come later!"
Annie then stopped herself before correcting herself over the word "come" then managed to get back on script. "The point is, even if there's something you think I can't handle, like your feelings or relationships or….dirtier stuff….I can get through it. And if I can't do it by myself, I know you can help me, like you do with everything else...even most of the uncomfortable stuff. And if you're uncomfortable, I can handle it and help out anyway. Maybe pleasing myself in your bed was a…flawed way to show it. But it was the best thing I had for this situation."
Well, there it was. The cards were all on the table, except for one leftover. "I'm not trying to make you commit to me, get over everything and want to be with me right now." At least now that Jeff wasn't making a move or saying anything to the contrary. But Annie didn't really expect him to, so she went on as planned. "I just want you to think about it next time….something comes along. And if you have trouble thinking, I'm right here and I'll try not to make it worse for you."
Jeff still had no response, leaving Annie to keep to the script as expected. "I'll see you on Monday, Jeff," she wrapped up, glad she had two days off to put herself together. Then maybe when he ignored it and went back to assuring her they were just friends, she'd get through the week better.
As Annie already built herself back up and walked past Jeff, her brain and body froze when his hand grasped her arm.
"You know, we're not quite even yet. All we proved is that we can….handle ourselves. But if you really think we can handle each other…." In the past, Annie wouldn't have gotten his innuendo, or what Jeff was actually suggesting. If she did, she would have fainted, freaked out or jumped on him right away.
But once it sunk in and Annie had a few seconds of deep, nervous breathing, she remembered the bigger picture – not that kind of bigger – and stated, "Well, if….that's all you want, Jeff, I'm afraid I can't help you." she somehow finished without stammering.
"Damnit, I knew I should have led off by saying it isn't all I want," Jeff lamented. And it got a little harder in non sexual ways….mostly….for Annie to compose herself after that one.
"Jeff, even if that's true, it's hard – more difficult – to believe in this context. It could just be sex stuff talking, or all those times I said handle! How do I know you'll still feel that way once you're not aroused anymore?" Annie nitpicked.
"Well, if I asked you out first, you might have thought I did it out of pity, or to make sure you didn't cry! See, these are the confusing, aggravating things I'm no good at! Even a genius like you is going to have trouble!" Jeff exclaimed. "I mean, I asked for us to jerk each other off before I said I wanted to….at least try for more! That tells you what you're in for right there, doesn't it?"
Jeff was barely shocked that he screwed this up just when he thought he got it right – or was ready to try and get it right. But there was still room for surprise when Annie responded, "Well….let's do that first idea before we try the others, okay?"
This made Jeff keep a close eye on Annie's hands before he made himself talk. "Are you sure? Because now it sounds I want to be with you just to make you touch me. I didn't mean that, but I can't blame you if it sounds like it. Not that I-'
"Jeff, I thought I was the nervous sex prude here, remember? Look, we're both clearly….backed up from last night and our talk today. Let's…clear our systems now, then we'll have the rest of the weekend to sort out the rest….if that's what you really want. I'm sure Troy and Abed will like making loud noises again for two more days. And I'd like to make some too."
Damnit, that just about got him. Plus once Annie saw his pants, she'd see she really had him. Well, Jeff never wanted to disappoint Annie – not even in the one area where he did, really. And now that he wanted to try and stop that…
After Annie looked down and started reaching for what she saw, Jeff took her hand and led her to the more comfy couch. No matter how much Annie made herself learn on this subject, Jeff still had some things to teach. But then again, he had to start before she touched him and he was the one who discombobulated.
Annie's fingers did some fine work last night, but Jeff probably had a few maneuvers they hadn't tried. He tested it by putting the tips of his fingers between her legs, brushing back and forth oh so delicately. From Annie's coos, it had the intended effect – but he had to halt once Annie's own fingers touched the front of his sweatpants.
As Annie traced the shape of his erection, Jeff's hand went just as stiff. Not so much from the stroking, although that was quite good. He had to admit that it had….this kind of effect because it was Annie. He then had to concede that no matter what she was doing and how, it was going to have that effect on him. This was the case when they weren't touching each other, and now that they were….
With that, Jeff made his fingers move up higher, which made Annie groan long and loud before she traced up his pants too. But Jeff got his fingers in her pants first, then worked on stroking her through her panties – which somewhat helped distract him when she stroked through his underwear. If only barely.
Jeff then sped things along, taking his hand out and signaling that Annie's pants were coming down. Once she lifted herself up and let Jeff take them down, he took his down by himself. Now that their bottoms were exposed, they savored getting a more up close look at what they were packing this time.
Soon, Jeff put his right hand on Annie's bare opening, studying it intensely – especially when he felt Annie grasp his bare erection. They stared at each other's crotches as they started stroking them, adjusting to the feel of stroking someone else this time.
Jeff's heavy breathing only barely drowned out Annie's as they moved their hands faster. But perhaps going faster wasn't the right way to make this last longer. Yet the soft grip of Annie's hand and the painfully slow way Jeff traced his finger inside Annie made going slow risky too.
Foolishly, Jeff took his focus off of Annie's groin and looked up at her face. It was still looking down at his crotch, yet he still saw her studying it so hard, just like a book. He also saw the same arousal from last night, which wouldn't help him last longer. Yet he was losing his ability to care at the moment.
"I need you to look at me, Annie." Jeff somewhat regretted his words, since they were the exact ones he used with fantasy Annie two weeks ago. Real Annie knew that too, and he didn't want her to think he was just living out the fantasy. Even now, a part of Jeff did want her to think that and leave more room for denial – but he was annoying enough in regular situations. Now he was downright irritating and Jeff had better things to focus on.
Like Annie's eyes looking right into him during their mutual masturbation.
At that point, Jeff almost repeated another fantasy line – the one about her being so fucking beautiful. Which she was, but quoting his fantasy to say it was too cheesy.
But once it registered that Jeff hadn't even kissed Annie yet, he got cheesy anyway and did just that.
His free hand went on her face and hair while her spare hand went on his waist. Although their hands were pumping faster again, their lips were still moving rather slowly and softly. This contrast even held up once they started using their tongues. Even with Annie's perfect hand churning him out so much better than his own – despite its 25 year head start – Jeff remained stable enough to savor the touch of her lips, tongue, face and hair.
Well, that was the final clincher right there, wasn't it?
Annie was well past any clincher, as Jeff's lips, tongue and hands practically commanded her hips to move up and down. She tightened herself around his right hand, even more so than she had against her own last night. But that was partly for show and to clear her system for today's follow-up talk. This was for a far greater need, as her hips and hand went faster once their lips finally parted.
Even now, a part of Annie did say she was being foolish, and that Jeff would run again once he got off. If he could go far enough to masturbate in the study room, his techniques here might just be more advanced ways of getting off. She already flirted with demeaning herself last night, so falling for this act would be a fitting ending.
But she knew that going in and she went ahead with it anyway – and it was exceeding all expectations so far. Annie took a risk, got through some very awkward moments and situations, and here Jeff was at last. Even if it was a sham, that didn't mean the plan itself was.
In any case, she said she could handle any situation, or learn to do it eventually. So it had to apply to heartbreak as well. And just as Annie said Jeff could count on her for help, she knew she could count on others too. She had Troy and Abed to support her, as they did when she explained her PG-rated version of her plan. It made her feel guiltier about being lewd while they were outside, but that couldn't be helped. In addition, she had Britta, Shirley and even Pierce to pick her up – and come up with Jeff revenge plans if hers fell through.
And if revenge plans weren't necessary….well, it almost made her lose it then and there.
Annie would be fine no matter what – eventually. Yet there was no point thinking about that when she had Jeff's thing in her hand. She was shocked she could pump him and have this inner dialogue all at once. However, now she should focus on doing just one task for once.
Powered by that truth, Annie gripped Jeff's member as softly as she could, yet stroked even faster. After Jeff's moans got louder than ever, she switched up by gripping him harder and stroking slower. Before long, Jeff repeated the same pattern on her as well. Soon their free hands worked to pull their bodies closer, before both their hips thrusted against the occupied hands and they kissed again.
While they were fucking each other's hands, there was probably no time to fuck each other. Yet that was fine, since they were only working on masturbation closure. There would be time for the rest later – and that didn't seem like just a fantasy anymore.
For now, Annie just focused on Jeff's fingers inside her, his lips on hers, his cock throbbing in her hand, and her upcoming first orgasm from someone else's hand. The thought of releasing in this apartment for the second time, only from his own hand this time, made her impossibly hotter. So did the thought of him releasing because of her again, only this time by her own hand. "Oh, fuck me….Jeff.…" Annie called out without thinking, and that was that for both of them.
Annie tried to keep her eyes open while she came, knowing Jeff would love that, They were closed about 85 percent of the way, but she steadily opened them up more. Jeff took notice – if only to notice something other than her hand and his coming release. But then he practically went blind as he felt himself go off….and then keep going.
At that, Jeff suddenly realized something. "No, no, not on her!"
Jeff barely got Annie's hand off his erupting cock in time, then covered it with his free hand instead. But it wasn't to stop his juices from getting on his clothes or couch – that battle was long gone. He was doing it so they wouldn't get on Annie or her clothes instead.
However, he was going on sudden instinct, so it didn't completely register yet. Right now, all his attention was on watching them both come – then on watching his last few spurts when she was done.
After several seconds, Jeff took his right hand out of Annie and his left hand off his cock. He clasped them together – two seconds before seeing how he pressed his juices and Annie's against each other too. This was probably some profound hidden metaphor, but Jeff could only see the juices now. By the time he noticed the stains on his lower shirt, pants and couch, Annie was already laughing over his hands.
As gross as sex stuff was to Annie a few years ago, she had learned not to be so squeamish – obviously. Now the sight of her and Jeff's releases mixed together in his hands was making her laugh. It was absurd that Jeff had both hands covered in the stuff, that he clapped them together – and that it even got that far in the first place. Yet the last part was absurd in the good, relieving way, which helped make Annie laugh even louder.
"That's right, laugh it up," Jeff pouted as he held his clasped hands up. "Once you get a job, your first paycheck is going to pay me back for my dry cleaning bill. Just know that going in."
"Too bad I'm one of Britta's 99 percent, so you'll probably wait a while," Annie got out before laughing harder. She did get out a few "I'm sorry"'s to show she wasn't laughing at Jeff. But he had already gone to wash his hands – with his pants still around his ankles. Yet the little grunt she did hear sounded suspiciously like a chuckle.
He was obviously going to change, and Annie briefly wondered if she should watch – but spying on him a second time probably wouldn't pay off as well. Abed's rules about inferior sequels probably applied too. Besides, the grossness of sitting on a cushion with….stains was starting to sink in. So Annie got up to clean herself off, then went back to the kitchen table.
When Jeff returned fully dressed up, Annie waited for him to say anything. Once he didn't, Annie figured that the silent, deflective Jeff snuck back up during his post-sex haze. She gave it a few moments before planning to take her leave and let them recover until Monday. "So….I guess I can go get changed, then?"Annie asked when those moments were up.
This represented Jeff's last chance to try and get free and clear. Yet that last session, and all it symbolized….was too exhausting for him to think up another lie. Maybe it'd be like that even if he wasn't exhausted – though it didn't make a difference anymore. But he would at least have fun with this first.
They could have fun in an even hotter way than they did on the couch. Yet after that sleepless night and that draining couch time, even Jeff had to recharge. Besides, they had a whole weekend to cross that off – only if Annie kept it on the table. However, he knew she wanted, needed and deserved deeper promises right now.
"Well, I had to change, but you're clean. And we don't have to go to lunch for another few hours, so you got time," Jeff blindsided her.
"When did lunch get into this?" Annie investigated.
"Oh, sorry. I don't know the protocol in Troy and Abed country, but people usually eat lunch at noon. It's a few hours before noon, so we're eating breakfast first, right here. But I don't have any lunch foods, so we'll need to go outside then, and in nicer clothes than pajamas. As cute as yours are, there is a time, place and location for them. Don't worry, you're a new immigrant to Jeff-merica, you'll learn the lingo in time."
Annie was unsure if Jeff's wise-acre commentary was promising or not. "Is….there a Jeff-merica to English translator that can help me?" she tried to play along.
"Right….well, I had to speak Annie lingo sometime," Jeff sighed. "Annie, I usually send women on their way after sex, or stuff close to sex sex. Doing something different is out of my comfort zone….but getting out of there has been a winning strategy so far. So we can keep it up by eating breakfast here, lunch outside, and then do whatever you want the rest of the weekend…whether it's talking or other stuff. After that, we'll probably need a week of rest before I can take you to dinner. But whatever schedule you can handle is fine."
Before Annie officially got giddy, she figured it'd be better to keep playing for now. After all, it seemed they had a whole weekend to talk and straighten the rest out. She probably needed something in her belly first, though. "Well, I can handle breakfast better with….actual breakfast. I'm sure that's a universal language in any country."
Jeff groaned his first non-sexual groan of the last 12 hours, since he did forget to put out breakfast. Yet Annie giggled and got up herself. "No, I'll find something. I'm a guest worker, I should pull my weight if I'm going to get that green card!" Annie briefly thought he saw Jeff's her-smile before turning around to look for cereal.
Now she could get carried away with romantic possibilities, even after the dirty stuff they had done. Perhaps if they had time, Annie could ask Jeff about the specific fantasy he used in the study room – and if it was workable. But that was probably third or fourth date material. After all, she still had some standards left.
Meanwhile, outside Jeff's apartment door, Abed had just taken his hand off of Troy's gaping mouth. It had been holding in a shriek ever since they came into the halls seven minutes ago – and overheard the tail end of Jeff and Annie's little 'study session.' They came by to check on Annie, figuring her plans with Jeff had reached a climax – but even Abed didn't anticipate it being literal. Not until May sweeps, anyway.
"All right Troy, we've officially filled the old 'friends overhear comical, dirty sex stuff' cliché. I'm surprised it hasn't been used more in our adventures, actually. But we filled the quota for this season, and they sound like they're good with their clothes back on, so we can go," Abed reasoned.
"Yeah…..you sure we don't need more research and super sex hearing?" Troy asked while still in a trance, as his jaw was only slightly closed now.
"No, accidentally spying on sexual activities never pays off in the long run," Abed assured as he finally led a frozen Troy away.
At least there was a 50/50 chance Troy would recover before Annie came home on Monday afternoon; maybe 20/80 for him acting normally Monday morning in the study room. Yet Abed figured Jeff and Annie would severely upstage Troy that morning anyway.