Annie felt a big lump next to her when she woke up. At first, she briefly thought Abed was filming Troy in a death bed scene in her bed – while she was in it – without permission again. But when she actually opened her eyes, she got clued in.
In a flash, she remembered who was in this bed, whose bed this really was, and what happened last night to get them there. When it registered that she slept in the same bed with Jeff Winger for the first time, her heart did a little cheer. When it remembered how it happened, it turned in its pom-poms.
And here Annie had thought she was really becoming a grownup. That by treating things with Jeff so casually and taking his anti-commitment speeches seriously, she was being smart. That she could enjoy being in a relationship with him and be protected when Jeff inevitably ended it. That sex would either make it too serious, or scare one of them off. And that Jeff only wanted to cross Annie off his Greendale bucket list, and would lose interest after getting everything from her.
God, Annie really was a Britta. Her and Jeff assumed the worst in people, even when all evidence was to the contrary – not Annie.
But she had assumed a worst part of Jeff that wasn't there anymore, or at least wasn't in control of him like before. Yet after years of heartbreak and setbacks, Annie wanted to be prepared to get let down – even after Jeff started dating her. Even after she should have known she wasn't dealing with that hurtful, distant Jeff anymore.
The one who never said he loved Annie.
God, she even ruined that milestone too. And after groaning, she noticed that she could add waking Jeff up to the list of screw-ups. Though his back was still turned from her, like last night, he stirred and managed to turn himself around to face her.
"So was it good for you?" Jeff quipped, which made Annie blush a bit and nearly whisper that they didn't have sex. Yet as Jeff smirked, Annie figured that was just what he wanted, so she bit her tongue and stopped blushing.
"It could have been better," Annie tried to joke, but this reminded her how last night really could have been better. She already apologized to Jeff enough in bed last night, yet a few more sorry's might be needed. "Jeff, even if you don't want to keep hearing it, I'm still really sorry," she started.
"Kind of early to beg for forgiveness I already gave you, isn't it?" Jeff wondered. However, this inspired Annie to come up with another tactic.
"Then I'll go with the thank you's instead," Annie offered. "The thank you's I should have given you for being such a good boyfriend. You really have treated me like a princess and I am so proud of you. I just thought if I focused on that, it'd be too hard if…..or when, like I figured….you had enough." She stopped that line before going into apology mode again.
"I wanted to treat this stuff like I thought a grown-up would. Practical and realistic and not with my head in the clouds. You hated that anyway, and I wanted to make this easy for you while I could. Of course, the one time I believe that you believe your cynical nonsense about relationships, I get it wrong. What do you know?" Annie reflected.
"Well, it's not like I helped you know better," Jeff admitted.
"But you have in these last few months! I believe it now, and I'll never doubt your commitment again! Not until you give me an actual reason to!" Annie promised.
"I admit I might give you a few," Jeff said, which took Annie aback, just when she thought they were on a sentimental roll. "Annie, you are right. I might always believe that relationships and love are stupid. Even if I know you're the exception that proves the rule. I don't want to be too lame and sappy to be my usual awesome self – but I don't want to be too awesome to be a bad boyfriend to you. I want to be both! The cool, awesome winner the world knows me as, and the….better version I am with you."
"Aw, Jeff," Annie choked up. "Well, those two Jeffs are pretty spectacular together," she conceded.
"So are yours. Your two Annie's, I mean," Jeff started again. "I get that you weren't being naïve and you were being practical. I love that you're doing that. But I love the old Annie more, no matter how I tried to deny it earlier," he let out. "I want you to be the same sunny, bubbly, pain in the neck we all wind up loving to death anyway. Combine that with the grownup Annie, and you two will rule the world in days!"
"Jeff, I should probably graduate first before I rule anything. And technically, I want to be elected to the job, anyway," Annie stated, surprised but pleased that she actually teased him back instead of melting into goo. The grownup Annie really was alive and well, and being used for good this time.
"Of course you do, your Highness," Jeff promoted her up from Milady. "But I think voters want to see you be the kickass Annie you've turned into, and the kickass Annie you've always been. Keep those two sides together, and no smear campaign or dumbass co-worker can stop you."
"I will if you will," Annie proposed. And despite the labored metaphor, the basic point was true.
If Annie could combine her new skepticism and growth with her usual optimism and big heart – and not favor one side over the other – the results may well be epic. They certainly were when the new caring Jeff and the old awesome Jeff came together to iron out their rough edges.
And the way both their new and old sides came together reminded Annie so much of how her and Jeff did. Alone they were formidable, but together they might be unstoppable. And now that Annie could feel safe to think like that again, she was almost at a loss for words. So she used her kisses instead.
In the middle of their soft, slow making out, some words did finally pop up in Annie's mind. "You love me," she remembered as she nuzzled into Jeff's neck.
"Who gave it away?" she heard Jeff inquire, feeling the rumblings of laughter in the hard chest pressed against her.
"Oh, just some jerk," Annie mumbled, making sure to suckle on Jeff's neck extra sweetly so she could have the last word. As Jeff groaned from it, Annie suddenly wanted to hear him make that noise for her again. And again.
Once he did two more times, she wanted more – and without thinking about what that meant, she reached down to the bottom of Jeff's shirt. Yet after her fingers brushed Jeff's belt, Jeff inhaled sharper than Annie had ever heard him, then stopped her from going further.
"Annie, are you….?" Jeff couldn't even finish asking. But Annie didn't need him to, as she just nodded yes. "Wait a minute, this means our….first time would technically be makeup sex! Is that how you want it?" he made sure.
"Well, knowing you and knowing me, we'll probably need a lot of makeup sex sometimes. Might as well start practicing now," Annie reasoned. And with that acknowledgment that there might be a future in this after all, she rolled on top of Jeff and resumed suckling on his neck even more passionately.
However, Annie was in no hurry – although she really did have to get going and help Troy and Abed soon. Yet that was the furthest thing from her mind, as she started enacting the fantasies she struggled not to indulge in for three months. She broke from Jeff's neck and tried to get his shirt off, but Jeff soon took care of it for her. With that, Annie got her own shirt off herself, then laid back on top of Jeff with only a bra covering her top half.
She then went back to a slow, sweet treatment. Now that she could finally let herself kiss every inch of Jeff Winger, and that Jeff wanted her to, she wanted to fit in as much as she could. Annie put her left hand on Jeff's waist and her right on the back of his head, and kept the rest of her body below the neck still as her lips and tongue did the real work.
They kissed and nibbled up to his left ear, then kissed back down across his neck and all the way up to the right ear. Her right hand gently played with Jeff's precious hair as the left started to glide up to his brilliant abs. Meanwhile, her mouth went across his cheek and then gave him a few brief, fleeting kisses with tongue before returning downwards to his throat.
Annie was so focused on kissing as much as possible that she almost tuned out Jeff's moaning and groaning. Yet she couldn't tune out how his hips rose up and collided with her centre after that kiss – and the obvious things she could feel from it.
Jeff was raging hard and Annie hadn't really done anything. She didn't even get to the steamy stuff and ideas she kept in the back of her head. All she was doing was the sweet, romantic, gentle stuff to get that of the way before going hot and heavy. And yet as she examined Jeff closely, he looked close to the brink just from the gentle kisses and caresses. That was….somewhat surprising.
No matter how much she wrongly assumed about Jeff, Annie knew he didn't do this kind of sex too often. He was an overwhelming force of nature in bed, at least according to his biased opinion, and likely didn't have the time or motivation to be romantic with sex.
But in this case, it only took slow, gentle kisses and rubs to drive Jeff crazy. She couldn't even blame his erection on morning wood, since they talked long enough beforehand for it to go away – probably.
If not, then the conclusion was that this kind of sex did turn Jeff on. Or at the least, it turned him on when it was done by Annie. It couldn't just be because it'd been a while without sex for him – likely longer than most times for him. If he was that built up, he would have devoured her right away, but instead he let himself get swept away like this. Like he likely hadn't by any other woman before.
Yet once again, Annie was the special exception for him that no one else had been. And now that she'd thrilled Jeff in a new way, she wanted to thrill him in old ways like no one ever had before.
But just as Annie moved down to kiss his chest more intensely, and was about to head for his nipples and abs, Jeff chose then to suddenly leap out and put her on her back. "Jeff! I wasn't done yet!" Annie called out.
"Yeah, but I didn't want to be done yet," Jeff gasped out. "You've done enough making up for last night. I have three years to start making up for, thank you."
To begin that quest, Jeff started devouring Annie's neck and hit her most sensitive point right away. Annie now began to gasp, especially when Jeff's arms went underneath her and wrapped around her, pressing her half naked body right up against Jeff's. He then grinded a bit against her, which set Annie off on another series of moans and made her hug him close to her as well.
Jeff set off a few more goose bumps by trailing his hands down Annie's waist and then grasping the top of her skirt. His mouth soon trailed down to the top of her chest while slipping her skirt down until her panties were exposed. Once they were, his hands slowly went up the top of her legs and grasped her panties next, pulling them down just low enough to expose Annie's crotch.
Finally Annie tried to get her skirt and panties completely off herself, but Jeff got off her briefly and took care of that. This left him the perfect angle to look down at how Annie was nearly naked except for her bra.
"I waited all this time for that…." Jeff all but whispered. Before Annie could put her brain back together, Jeff added "Worth. Every. Minute." and then put himself right back on top of her. For good measure, he grinded his still covered erection against Annie's now bare pussy and almost made her voice give out then and there – among other things that almost gave out.
"Jeff, please, touch it for real….." Annie somehow had enough strength to ask. There wasn't much more she could say, as Jeff's steamy yet still sweet tactics were making her gasp too much to talk. And that was before he started brushing his hand over her opening. And before he put his thumb above her vagina and had his other fingers glide over her outer lips without dipping in quite yet.
Then he went and started kissing her still bra-covered breasts for good measure. Although Jeff didn't take the bra off yet for some reason, he still kissed and suckled her nipples and the rest of her clothed flesh through the fabric – which was still plenty hot anyway. So were the two fingers gently making their way inside Annie, for that matter.
Jeff took one of them out and let the other go a little deeper inside. After it thrust around and made Annie arch her back – and stick her chest out further for Jeff to play with – the second finger returned inside and went in deeper as well. After a few minutes, Jeff finally took those fingers out, saw them covered with her juices, and then glided the wet fingers up Annie's stomach and towards her chest.
Annie only had a second to try and see the wet trail left on her. At that point, Jeff dove down, gave her pussy one big lick, then licked all the way up the long trail of wetness and got as much off her as he could. Now back completely on top of Annie, Jeff's tongue got right back to work on Annie's breasts and bra cups – and after seeing what that tongue did earlier, Annie almost lost it then and there.
"Jeff! Jeff, finish it, please!" Annie yelled, fighting a losing battle to keep some self control. It didn't help in that regard that Jeff put two fingers back into Annie and brushed a third against her. But right before Annie could lose it, he cruelly took his hand away and only then worked to get his pants off.
Even more cruelly, Annie only got a brief glimpse of Jeff's exposed erection before he laid back on top of her, laying his head on her neck this time. Although she couldn't see Jeff's member, she could feel it as Jeff's right hand helped rub his head against her opening now. It didn't go in, yet his left fingers returned instead – and soon he rubbed his tip against her opening as fast as his fingers were rubbing inside it.
"Jeff, God, Jeff, fuck, God!" Annie called out incoherently as she was brought to the limit. Her orgasm landed all over Jeff's left hand as his head pressed deeper into her neck. Annie's hips shook and gyrated for several seconds until she was spent, then her and Jeff barely moved as they caught their breath.
At last Jeff removed his hands and fingers from below Annie, with his left even wetter than before. Annie got a good look at her own juices all over Jeff's left fingers, which distracted her as his right hand finally pulled down her bra cups.
With her breasts fully exposed, Jeff actually rubbed her juices into her tits, then started licking them up from there. Even when he got all of her juices off, he kept suckling her breasts a few extra moments longer to be sure.
Soon even Jeff had enough with even Annie's breasts as he rolled off her. Once Annie actually unhooked the bra and threw it away, the two just stared at the ceiling for a while until Jeff managed to look at her again. "And you really thought…..I would lose interest in you after I did that?" he double checked.
"Okay, so I can be just as clueless as you sometimes, you got me," Annie somewhat hoarsely responded.
"Well, you've got a long way to catch up to me there. Probably take you 40 years or something," Jeff joked. Annie knew that wasn't a commentary on how long he expected to be in….this, with her. But it did remind her of how she thought this was just temporary, and would reach the beginning of the end after sex, just 10 hours ago. Yet now….
"I want to say I love you too," Annie admitted. "But after….that, it'd sound like a heat of the moment, post-orgasm kind of thing." Jeff smirked at her using the o-word without stumbling, which made Annie roll her eyes and smirk back before being serious again. "But we're going to finish this, then I'm going to relax, and in a few hours I'll say it with a clear head. So there's no question that I mean it."
"I think I figured out you meant it long before today," Jeff reminded her. "But you know, I technically haven't had a post-orgasm kind of thing yet." At hearing him say the o-word and seeing him point to his still hard groin, Annie finally blushed. "So does that mean I can say I love you now and you'd believe it?" Jeff proposed.
"I think you reached your quota for 'I love you's' for a while last night," Annie let him off the hook. "Don't worry, Jeff. You don't have to be sentimental that much if it still makes you uncomfortable. I'm willing to work with you and whatever hang-ups you still have, not attack you for them. You've earned that leeway."
"Won't saying it more make me less uncomfortable eventually? God, I already have to do all the work and sacrifices in this relationship," Jeff comically complained. Annie rolled her eyes at the last part, but then reflected on his offer in the first part and smiled more sweetly. To punctuate it, she learned up and kissed him a few more times.
"I know you love me too, Jeff. I know it and I believe it now," Annie assured. "Of course, there's still one more thing you haven't done yet to prove it." Now Annie was the one to glance down at his groin, which made Jeff get the message and smirk in anticipation.
But first, Annie reached her hand down there, figuring she at least had to touch it once. Jeff backed up a bit so Annie could see her target, then she went and put it into her palm. She wrapped her hand around it and widened her eyes a bit at the feel of it, but adjusted quickly and went to place her thumb on the tip.
Annie let her thumb glide over Jeff's tip and was intrigued at how smooth it felt. Looks wise, what little she had seen from penises, or representations of them, made them look intimidating – especially for ex-prudes like Annie. Yet although this penis still looked intimidating – and as big as Annie imagined it would be – it was actually soft and firm and warm and welcoming to the touch. Kind of like its owner deep down.
Speaking of the owner, his breath seemed to be more uneven the more Annie swiped her thumb across his penis head. How very interesting. First he got extra turned on by Annie being sweet on him, and now rubbing his tip was doing a number. She had to remember these things and make sure they didn't get…..well, screwed out of her.
"Okay, I think we need to move this along now!" Jeff gasped out after two more slow thumb swipes. Annie let him get off her and reach for his desk drawer, where he got out a pack of condoms. He unwrapped one and Annie paid close attention to how he took it out, positioned it onto his cock and started rolling it over himself. This was the kind of proper condom use lesson Annie couldn't have learned or organized at the STD Fair, although this was more educational.
Annie giggled a bit at that thought and how much had happened since that infamous fair. But that spinster librarian Annie was no more, in spite of making a last stand in the past three months. Yet there would be no standing up involved here – not this time, anyway.
Jeff laid on top of Annie again, but he started off by reinserting his fingers into her. Annie clenched around them to get practice for later, as two stayed in and a third started to tease its way inside as well. Although this was still hot, she was getting a little impatient for the real thing – yet her train of thought was interrupted when the fingers pushed in her as deeply as possible.
Annie grit her teeth and closed her eyes, and thought she heard a little groan from Jeff as well. If that wasn't enough, she felt his now sheathed cock being rubbed beside her opening again. Then before she knew it, Jeff was pulling his fingers out of her – and the head of his cock then started entering her a second later.
Getting refilled like that made it go down a bit easier, although adjusting to this new size and girth was quite a task indeed. But Annie figured it probably could have been worse, if not for Jeff's finger foreplay. Of course, fingers had nothing on what was already halfway buried into her now. Then it pulled back a bit and thrust back in deeper than before, then repeated the pattern a few more times until finally sinking all the way in.
Annie rested her beet red, overwhelmed face against Jeff's shoulder, as she could feel Jeff bury his head in her neck again. Once her shallow breathing quieted down, she could hear feel even more shallow breathing against her. Interesting again….
"Worth it?" Annie forced herself to let out as a callback to all their waiting.
"Pretty close," Jeff answered, yet the fact he basically wheezed those words out said a bit more. Following a few more moments, he was able to start moving his hips back and forth again,
Annie adjusted to the movements and soon started to feel more comfortable. With the initial pain and discomfort fading away, she could let herself relax and savor this a bit more. Her hands grabbed onto Jeff's back and felt how tight and taut it was, more so than usual. Now that was something she could savor as well.
Just as she rubbed his front earlier, Annie worked on rubbing and caressing his back – and groping it after some particularly deep thrusts. Getting to feel his muscles like this, and getting to feel another big one inside her at the same time, was quite a lethal combination.
It got even better when she moved up to hold on to his arms and biceps, and had her fun feeling them up for a bit. Jeff responded by laughing just a little bit into her neck and then suckling it, so that helped too.
There was one more area left to hold onto, so Annie made her hands slide all the way down Jeff's back until they reached the target area of his ass. That cute butt stuck between those long legs and that scandalous upper body had taunted Annie for years, and now it was hers for the taking.
She grabbed onto his behind, made sure not to scratch it, and was able to use it to push Jeff deeper into her. And as she gripped his ass, pushed it forward and started to grind her hips up to his faster ones, Annie started to giggle again.
"This is fun!" Annie somewhat cheered, before a deep thrust made her groan again. She went back and forth between smiling and laughing playfully as she groped Jeff, and between groaning erotically from Jeff's own maneuvers. As she took that contrast in and saw how Jeff was gazing down at her in the process, she saw what Jeff was talking about earlier again.
The excitable little girl Annie and the wiser, experienced adult Annie were indeed coming together to make this even more fun and uplifting – to say nothing of Jeff himself.
As he leaned down to start kissing her again and she responded back, Annie realized she could get used to this. She was afraid to get used to Jeff and being together with him, when she assumed it was useless because he wouldn't want to keep it going. However, now that she knew that he wanted to, and even wanted to put in the work for it, it was a vast difference.
Now for the first time, Annie could feel safe to imagine doing this for a long time – maybe even longer than she could dare to dream right now. She could, but she realized there wasn't that much of a point to it.
There was little need to imagine or fear the future, because it would work itself out. It would because for maybe the first time since they met, Jeff and Annie were on the exact same page. They weren't hiding anything anymore, they both wanted the same things now, and they were each willing to fight for it and do it together. The rest would work itself out because of that.
And because of that, Annie finally felt safe enough to live in the moment.
A moment with a man who loved her, fought through years of doubt, self-loathing and excuses to be with her, made her feel safe and special, and let her know how safe and special she made him feel as well. The past and future remaining unresolved issues and relationship challenges didn't seem to matter as much compared to that. All that could be dealt with later because Annie knew that she and Jeff could defeat them now. Fully united, on the same page, and together.
After they finished this draining, mind blowing, hot, tight, warm and so fucking good sex, of course.
Once Jeff started using those fingers again, and Annie put her hands on his waist to finally get to those abs, she knew it wouldn't take much longer.
"Fucking…..please tell me you're close," Jeff got out. Annie smiled at his shaky voice, further emboldened by how little Annie was making sexual master Jeff Winger lose his composure the first time out. She hadn't even used those special tricks she found online over the years yet. But she could surprise him with those later – as now he deserved to just get off.
"Don't worry, I'm getting there….getting there…." Annie repeated while raising her hips to meet his thrusts. She then wrapped her arms back around him and made sure their naked chests were colliding and being pressed together. With that extra sensation of ample bare skin against ample bare skin, it was the final little trigger.
"Got there! Got there, oh God! Get there for me too, Jeff, fucking get it! Fuck me!" Annie yelled out with less coherency by the end.
With her going off for the second time, Jeff found one more burst of speed to get him over for the first time. Despite how he spilled into his condom and not into Annie, she was still swept by the most incredible sensations, as she felt him go off while she finished as well.
When they were both finished, Jeff fell on top of Annie, then took a lot of effort just to roll off and not crush her. Finally she was able to snuggle up with him and lay her head on his chest, trying not to feel too sappy about hearing his racing heart.
"You wanna review why that took three-and-a-half years again?" Jeff said with a limited amount of energy. "Actually, never mind. The first three years are kind of a drag, anyway."
"Good…..already sleepy,' Annie trailed off as their activities finally did a number on her. So did sleeping on Jeff for the first time and not beside him. She put a hand on his abs and stroked her thumb over them, as Jeff's exhausted and yet still sort of ragged breathing helped lull her back to sleep.
The next thing Annie knew, her head was still on Jeff's chest when she woke up, and she couldn't help but give it another few kisses. She wondered if this would wake Jeff up, then got her answer several moments later when she felt a hand go onto her cheek. Jeff then used that hand to pull her into kissing his lips, and Annie was briefly convinced she was still dreaming.
But there would be no need to dream about Jeff anyway – at least not any dreams that couldn't eventually become reality. Anything was possible now after sleeping together, having the hottest sex together, and both wanting it and more for longer than a fling. It was like something out of those movies on romcom night at…..
And with that, Annie remembered she was late to go home – then threw her clothes on when she saw how late.
And with that, Annie couldn't get home in time before the whole apartment was totally wrecked, since Troy and Abed didn't have a script woman to keep their shoot in order.
And with that, Annie's nap on Jeff's chest was the last bit of real sleep she got for the next few days.
Worth. Three-Quarters. Of The Minutes.