Jeff just wanted a quick and dirty masturbation session tonight so he could go to sleep.
So he went through his dirtier Annie fantasies – the ones that'd make him cum so quick, he wouldn't feel that awkward seeing her with clothes on tomorrow. The vision with her on all fours would probably do it fast.
So Jeff closed his eyes and pictured Annie on his bed, bending oh so perfectly on her hands and knees. As he started working himself over, he pictured Annie looking over her shoulder with a smoldering gaze. But then again, smoldering wasn't a look the real Annie had mastered yet.
Jeff was more used to seeing other gazes from her. Like that overexcited one when she aced a test. Or that schmoopy one when she saw a cute animal – or saw Jeff doing something she thought was cute. Or that smile before she hugged him for doing something right for a change. Or that "long looks and stolen glances" smile they'd been sharing together more than usual.
Without realizing it, Jeff pumped himself faster from picturing that smile alone. It wasn't one of her childish smiles, or her overly adoring smiles, or even a Disney smile. Recently it had become something more….real. One where she didn't look as schoolgirly or swoony as she did before.
Like she knew Jeff wasn't the romantic dream guy she daydreamed about in the past….yet could still adore and appreciate him. Like she could still be proud of him, despite knowing full well what he really was. Maybe despite knowing him better than he ever thought possible. Yet that smile saw right through him…..and liked what it saw anyway.
But once Jeff gripped himself too tight, he snapped out of it. It helped him remember this was supposed to be quick and dirty – not girly. So he went back to imagining Annie's more private areas.
The boobs would probably get him finished in a hurry – they usually did.
Jeff had practice in picturing Annie's boobs naked, and imagining how they'd bounce and jiggle against his chest while naked. Plus Annie had been showing so much more in the last few years, it wasn't that hard to picture them naked anymore. Not after seeing almost all of them in cardigans, low cut blouses – and especially sexy Santa outfits.
Unfortunately, the sexy Santa boobs usually made Jeff remember the baby talk too. Diminishing and disappointing returns indeed – both for him and for Annie, really. Jeff tried to think of something else to make him feel more aroused – or at least less guilty about feeling aroused.
But instead, Jeff somehow thought of what happened a few days after sexy Santa. He thought about that actual Christmas, when Annie was still embarrassed around Jeff after her routine.
And yet she got through it to give him her Christmas gift – one of the rarest and most expensive wine bottles he'd ever seen. Annie explained that after the rough semester he had, and the brainwashing he just survived, she thought he'd need the best alcohol to take the edge off over break. Then he could come back next semester and be ready to start anew, or some other kind of Annie logic.
Despite how awkward she still felt, she still gave him an incredible gift – one she spent way too much of her limited funds on. But she did it for him anyway, because she knew he needed all the help he could get after that horrible semester. And she knew him well enough to get him just what he'd like too. It all overwhelmed him, even before she gave him that perfect smile after he thanked and hugged her.
Jeff's hand went faster again after remembering that moment. It also went faster when he remembered the other generous things Annie had done for him. Like when she gave him advice, pep talks, courage, confidence, and her unwavering faith that he could do something – even when he didn't see it.
And she always looked so proud of him when he did it – and so surprised when he gave her credit. Like it still stunned her that someone could actually like something she did for them. Even that tiny, barely good enough gesture could subdue the….aching loneliness he knew she had deep down.
The kind that didn't completely go away after years of neglect, no matter how awesome and super hot she'd become. No matter how much more loved she should have felt every day. But the people who should have killed that loneliness before it was born failed Annie miserably. So Jeff figured he'd have to –
Great, he was getting all sappy again. And this was supposed to be disgusting in the hot way!
Jeff willingly ignored how he jacked off harder and faster when he thought of Annie's happy looks. He ignored being on the brink when he pictured himself making her look so happy. It was already sick, unrealistic, lame and…..not Jeff Winger to think this stuff at school, when she was around. Doing it when he was supposed to fantasize about Annie's unspeakable, naked, sexy, beautiful, gorgeous, lovely things was something else!
With that, Jeff willed himself to focus and be filthy one last time. This time, he just stayed on track and imagined fucking Annie, and nothing more. She was doing nothing but riding him, calling out his name, letting him play with her tits, and yelling unromantic things at him. It was ultra hot, straight up fucking with nothing else attached to it – much more like the real Jeff.
It didn't matter that this wasn't like the real Annie. It didn't have to be, since this was only about getting off. That was all that mattered here.
Now Jeff was feeling it, so this would be over soon anyway. Thinking about Annie bouncing and jiggling and just showing off her body was enough now. All she had to do was lay on top of him and fuck him senseless. Lay those perfect breasts on top of his chest. Bounce that perfect ass up and down his groin. Let that perfect skin rub against his as she brought herself to climax….
Of course, Jeff would have to hold her against him so she'd feel comfortable when she came. Common courtesy, really. Then if Jeff held on tightly to her when he came, she couldn't complain if he did it too hard. Then they'd have to catch their breath, since they'd be too tired to move for a while. Too tired to get Annie's body off him, or to get his arms off her smooth back.
Or to keep from falling asleep just like that. To keep from letting the feel of Annie and the breathing of Annie lull Jeff into sleep. Enough so he wouldn't wake up until the morning.
Even then, he wouldn't open his eyes. He'd still be too tired – and too surprised to feel Annie still in his arms. To feel any woman in his arms the morning after. But he'd be too exhausted to move his arms off her naked body. Yes, that was it.
Yet while Jeff's eyes would be shut and his body would be still, he would still feel Annie moving. He'd hear her yawn and stir herself awake, yet he wouldn't be ready to open his eyes and face her. But nevertheless, he could feel Annie looking at him – and probably awwwing at his supposedly sleeping form – and it would get too much for him.
Then he would turn his head, slowly open his eyes – and the first thing he saw would be Annie's bright eyes and sweet smile. God, she really was a morning person. Another way she was so different from Jeff. But Jeff never saw this when he woke up in the morning.
Of course, Jeff had woken up to his share of smiling, clingy, Jeff-crazy women before. But none of them were Annie. She didn't even look clingy or overwhelmed, or stunned at what they did. She just looked…..relieved, content and calm. And happy he was actually there with her in the morning.
And when she was happy, Jeff got to see her eyes and lips light up the most. In his bed when he first woke up this time.
True, it was nighttime in reality and he was imagining this while trying to jack off. And yet the thought of Annie's eyes and smile being the first thing he saw in the morning….it was still so vivid. And…..addicting. Like her eyes, smile and happiness usually were, but….in this context they were….
"Good morning," Jeff imagined Annie saying in bed before he finished that thought. Then he imagined Annie kissing him, but then pulling back after a second.
Now she looked a bit tentative, like she was afraid she had gone too far. That she'd assumed and thought something which was all in her head. Worse yet, it brought that fear of loneliness back in Annie's eyes, instead of all those other things Jeff wanted to see in them.
At least in a fantasy, he could do something real about it.
In there, he could start kissing her. He could stop himself from pulling away when she kissed back. He could keep his arms wrapped around her naked body. He could actually keep kissing her without trying to do anything else. He could be satisfied enough by just feeling her bare body, running a hand up to her shiny hair, seeing her eyes and smile look bigger when he broke off….
God, it even sounded good outside of fantasy land all of a sudden. If 'all of a sudden' was the right term.
The more Jeff thought about it, the more he didn't care. The more he thought about just holding and kissing a naked Annie in bed, the more he shut off everything else. The more he thought of these sappy images when he was supposed to jack off….the harder it was to mind their sappiness.
But he was still jacking off. And when his groans got loud enough, he snapped out of it and saw just how hard he was doing it.
When the fantasy faded and Jeff saw himself, he saw his hand move faster on his cock than ever before. And the feeling from it was more intense than anything he'd felt before. It was too late to stop his hand or body – until Jeff froze up.
Jeff could only grit his teeth and groan as he finally exploded. It was perhaps the most intense 'explosion' he'd had since he was a teenager. If not ever.
His release landed all over the bottom of his shirt, the top of his pants and on his sheets before Jeff finally took action. He covered his cock with his hand, but that got pretty drenched as well. He kept releasing and groaning for a few more seconds until he was done at last. But he still couldn't move for another few minutes, despite the mess he was in.
Jeff was only coherent enough to reach over and get some tissues, although he couldn't do a thorough clean up. Then he barely made himself get up to throw away the tissues and wash his hands. In between, he did some hazy thinking about how he came this much, and this hard, just from thinking about cuddling and looking at Annie in bed.
That was not in character, as Abed would put it. Jeff Winger was not this kind of a pathetic girl. He was just under the influence of something, so it didn't reflect reality of any kind. However, he was too worn out to determine what that influence was – or to use his other denial tactics.
And if he was in no condition for denial, there was only one other reason why he reacted that way. Why jacking off to those fantasies, and to that woman, gave him his most intense orgasm in years – even though he did this himself.
But since this was more intense, it meant Jeff would go to sleep a lot faster. And after he walked back to his bed, he fell face first onto the mattress – but away from the stains – and did just that.
Jeff didn't move again until the next morning, and then moved on autopilot to get to school and the study room. He kept zoning out due to being tired, and due to feeling…..other things besides tired. He barely had the energy to look at Annie, as his Annie hangover was stronger than ever.
Ironically, Annie herself snapped him out of it when the morning study session ended. "Jeff? Jeff! We have to get to class now!" Annie stated until Jeff remembered where he was. Which was all alone with Annie in the study room – of course it was.
"What? Oh yeah, right, class, 10-4!" Jeff rattled off, hoping that'd be enough to make Annie move along. But it wasn't.
"Are you okay?" Annie asked, with that concerned look he was so familiar with last night. "Did doing nothing last night take that much out of you?" she wondered, with that playful smile that really got him going hours ago.
"It's nothing. Nothing at all," Jeff said a little too forcefully, which put that not so hot, slightly disappointed look on Annie's face. In the fantasy, he could wipe it off with better words and touches that paid off…..so wonderfully. But in reality, as usual….
"Well, on the off chance it's something, you can still tell me later. I know, you can only do that a few times a semester. But I've got a lot of patience, mister," Annie said before smiling.
There it was. That smile Jeff woke up to in his fantasy. Maybe not that exact one, but it was pretty damn close. It might be the closest he came to seeing it, though – but it didn't feel like enough. It wasn't enough. Enough was never enough when it came to those smiles.
Maybe Jeff's natural defenses and denial weren't up yet, because last night took too much out of him. Maybe if he waited long enough, he'd go back to normal and brush this nonsense aside. Yet when Annie turned that big, loving smile away from him to leave the study room, he had the sudden epiphany – well, the sudden acceptance, anyway – that normal looked pretty rotten right now.
So before it was too late, Jeff started to turn fantasy into reality. Well, at least one G-rated part to start off.
"Annie, hold on!" Jeff started, then actually worked out what he wanted to say. He settled on, "There is something I'd like to tell you. But since we have to go to class….could I tell you after lunch? Alone?"
"Oh! Um, well….sure," Annie blushed a little, then caught herself. "The things I put off for a perfect on time record, right?" she tried to joke, giving Jeff that nervous, somewhat embarrassed but still hopeful smile of hers.
"Okay, I'll see you all alone then, Jeff. And, um, in case it isn't bad news and I forget to tell you later….thanks for coming to me." It took more work than Jeff had done in years to keep still at Annie's comment – and to take it the way she intended. Yet there she was with the smile and beaming eyes of his fantasies to make it worth it.
So Jeff made himself say, "Thank you for getting me to come to you," as sincerely and cleanly as he could. Then he left himself breathe a sigh of relief/slight disappointment when Annie finally left.
Well, at least Jeff had time to think of less suggestive material for later. He would need it – he would need a lot of things. But if it got him anything like he received last night – and not just the happy ending…..
Quick and dirty. Yeah, right. Like any of that could have anything to do with him and Annie. For the moment.