Here's the thing: she's not with him because it's a good idea, or the best choice. Annie Edison hadn't unceremoniously dumped Vaughn at the last possible moment because Jeff Winger is such a sweet guy who's gonna make the big romantic gestures and say the right thing at the right moment and be sensitive and take it slow. She's with him because this is the culmination of months of slow, agonizing circling before they both went for the forbidden fruit at once, damn-the-torpedoes style, and now that he's got Annie underneath him on his bed, Jeff is fucked if he's going to veer from the course of getting exactly what he wants – or in this case, not fucked when he very much wants to be.
It's not like he's a complete jerk. He's taken her out several times in the past couple of weeks, each evening ending in a make-out session that Annie had ended at the least opportune moment, possibly out of some misguided sense of propriety – or, more likely in her case, anxiety. But now, both of their shirts discarded and his fingers nudging her bra up as his lips move along the warm, heavy underside of a breast, she doesn't have any protests.
Working behind her back, Jeff finally gets the tiny hooks separated, and lifts the pale pink cups of her bra up to reveal a matching pair of pale pink nipples. He knows now that it's best not to vocalize his appreciation, since a stray comment the night before about Annie's hair had broken the moment and sent her skittering away, every repressive shield at the forefront. So he limits himself to meeting her eyes with a grin before he lowers his head and takes a nipple in his mouth, feeling it pucker more tightly against his tongue.
Positive response. She's whimpering and her hands are in his hair and he's perfectly willing to concede that point in view of the larger goal he's set for himself tonight of having sex with Annie Edison. She may not know about that yet, but there's no way she doesn't want it: her legs are wrapped tightly around his waist, pelvis rocking up against his, and she's flushed a rosy color from cheek bones to ribcage.
There's nothing wrong with their relative positions, Jeff decides, that the removal of clothing wouldn't render perfect. Annie's well distracted by the current position of his mouth, and he's got her floral-print gingham shorts unbuttoned, and along with her panties, slid halfway off her hips before she notices.
"Jeff!"she protests, trying to squirm away from his hands.
"What?" He's all innocence, even as thumb and forefinger give a gentle half-twist to one of her nipples. She goes heavy-lidded at that, and he ventures a quick glance downward. Pink panties. With her bra, a matching set. Yeah, even someone as dedicated to the principles of coordination as Annie doesn't go all out for lacy underwear unless they expect them to be seen by someone else.
So, Jeff feels practically no guilt for silencing her with a kiss as he drags her last remaining garments down to her knees (although he almost forgets what he's doing halfway through when she sucks his lower lip into her mouth) and then off, and even congratulates himself on completing that relatively difficult and risky maneuver.
Then he's half-leaning, half-crouching over a completely naked Annie, and when she realizes it, she breaks off the kiss and clamps her knees together, embarrassed.
"Jeff, I don't know..." She can't meet his eyes.
He moves beside her, head propped on hand. "Annie, look at me."
"You're beautiful." He's pretty sure that this is an good moment to throw that out there, and couples it with a lazy stroke of his hand to her leg, moving from knee to hip.
She blushes even pinker. Jeff's running on pure instinct now, his prior experiences with repressed, only-somewhat-experienced teenage girls being severely limited prior to this point. Which is something to be proud of, he supposes (since, y'know, now is such a great moment to reflect upon his own moral fortitude), but it doesn't help him any in this situation.
He's expecting a protest when he puts both of his hands on her thighs and gets off the bed to kneel on the floor in front of her, but when he starts to separate her knees, she sits bolt upright with a jerk of astonishment. Jeff's eyes glaze a bit as he appreciates the properties of gravity, but when Annie crosses her arms protectively over her breasts, his mind snaps back to what she's saying.
"You don't need to – I mean, I'm not expecting this. I'm not even sure if I want that, and I know you probably don't, so –"
Okay, lawyer mode. He sits back on his heels and raises his eyebrows as she babbles on incoherently for a few more seconds, then interrupts. "Annie, remember those personality tests you made everyone take a few weeks back?"
(She's startled enough by the sudden change in topic that her arms fall to her sides, but Jeff sternly commands his mental faculties to the task at hand.)
"The Five Factor Model?" she ventures, puzzled.
"Yep. Remember how you scored on openness to new experiences?"
"Low," Annie admits.
(But not as low as "neuroticism" and "conscientiousness" had been high, he recalls.)
"Didn't you resolve to do something about that?"
"Yes. And I did! I went to the movie rental store with Abed and bought a box of Pocky." Which she'd never tried before, put off by its inflated price and unappealing box images. "And then we watched a lot of movies that I didn't want to see." She harrumphs. "What does that have to do with anything?"
At least she's almost forgotten she's having a conversation while naked. "Did you enjoy the Pocky?"
"I can guarantee you're going to like this a lot more." Not that his ego appreciates him comparing his sexual prowess to a snack imported for teenage animation enthusiasts. But it doesn't matter when he's parting her unresisting thighs and running his hands up to their apex, and it's completely inconsequential when the way he applies his tongue to her clit makes her fall back onto the bed with a muffled shriek, her knees now as akimbo as it's possible for them to be.
It's an dick move, Jeff knows, but when she starts to moan he draws back, pops his head up high enough to see her face. "Would you agree that this is good new experience?" Yes, he is smirking.
Annie whines in frustration, and doesn't exactly push his head back down, but he gets the message and resumes. He's got her taste in his mouth and two fingers sunk in her up to the knuckle when her thighs begin to tremble, and he realizes how close she is.
A gentleman would finish her off, but Jeff's never claimed to be a gentleman, and he figures that an orgasm right now would leave her sleepy, sensitive, and at least for a little while, that much less eager to be penetrated. So he removes fingers and mouth and stands up, stroking his hand over her enough to make her writhe, but not enough to let her get anywhere fast.
Annie's Disney princess eyes are wide, her lips parted mid-gasp, and she watches wordlessly as Jeff shucks jeans and boxers and rolls a condom over his hard-on with the kind of speed and manual dexterity that would rouse the jealousy of a Nascar pit crew.
Whatever smart-mouthed (or pleading, it all depends) thing he might ordinarily have said in the situation doesn't even come to mind with Annie splayed out, looking up at him like she is. He's working her with his hand again, and she may be begging and it may just be whimpers, but he can't take it anymore, and replaces his fingers with his cock.
Jeff's never been one who attempts to objectively rate his sexual experiences, because he believes in enjoying whatever comes his way. But being inside Annie? It's fucking fantastic, and immediately ascends to the top of a list he hadn't even known he'd had. He's not sure whether it's the forbidden fruit aspect of it or the anticipation or just her, but he's already going white behind the eyes with pleasure and he grits his teeth, trying to get a hold of himself.
He looks down at her, tries to give an encouraging "We're all in this together, comrade!" grin, but she wraps her legs more tightly around him and bucks up against him. "Please, Jeff!"
Well, there goes that plan. Not that he's not thrilled to acquiesce, but from what he knows about Annie, and the scant facts he's gathered about her previous sexual history, Jeff figures that making her come won't be simple or quick. However, he doesn't need one of Ian Duncan's Psych classes to know that positive reinforcement is the best way to keep someone coming back for more, and so Jeff settles himself in for the long haul, queuing up Colorado's DUI laws to recite from memory as a distraction, but he loses his place three times, and somewhere between his measured thrusts and his fingers rubbing at her clit and his mouth sucking at the soft skin under her ear, she's there, clenching around him, her back arched completely off the mattress, the look of ecstasy on her face warring with one of astonishment – so, yeah. Probably the first time for that.
Chalk another one up to Jeff Winger.
Which he'd be a lot more pleased about if he weren't entirely focused on angling her hips up that much farther, panting out obscenities until the shimmer of sensation down his spine and his last, desperate thrusts spiral him into mindlessness.
Jeff eventually realizes he's slumped on Annie heavily, and that's not the kind of finesse he'd usually employ, but then, hasn't he established that this one is off the map of prior experience? Annie's watching him and he blinks, trying to bring her into focus, and she smiles. So he smiles, and hey, he's muzzy-headed and feeling no pain and it's late and that's probably why she ends up snuggled in against him (because even if Jeff's not a snuggler, he's also not stupid enough to turn down an armful of naked girl), the covers drawn up over them both.
As he drifts off to sleep, he should be high-fiving himself for the absolutely successful execution of his plan for the evening, but instead he's thinking about how he could get used to this, and – fuck. Mojo lost, too many nosy friends acquired, teenage girl seduced, sentimentality activated. Fuck Greendale.
Jeff should be angrier about it than he is.