This is the final follow up to "Oedipal Wreck" and "Oedipal Wreck 102" as the main details in both stories are detailed in this fic – in lue of reading them if you haven't already. But this finale is up to an M rating for soon-to-be obvious reasons.
In mid-February 2012, Jeff Winger made the biggest one-night stand mistake of his life; and considering that long list, it was actually an impressive accomplishment. It was also impressive just how destructive it nearly was, considering his one-night stand was Carol Edison; mother of his decade-plus younger dear friend, Greendale community college study partner and not-so-secret crush, Annie Edison. Add to it that she was Annie's estranged, manipulative, downright psychopathic mother who then blackmailed Jeff into silence while she tried to force Annie to leave Greendale two days later, and the hyperbole is more than warranted.
After it all came out anyway and Carol still failed to force Annie into transferring, it took until mid-April 2012 for Jeff and Annie to fully repair their friendship. By then, Jeff was no longer in denial about what he felt for the younger Edison, and was days away from telling her so. And then her estranged father had to die, they had to reunite with Carol at the funeral, and Annie was driven to make out with Jeff out of revenge right afterwards. Yet Annie then found some way to get closure on Carol once and for all, and was ready to try and be Jeff's girlfriend by mid-May 2012; although having sex with him was something she wasn't ready for.
Nevertheless, Jeff was done making mistakes with Annie; at least on purpose. So he willed himself to wait, enjoy their new relationship and help her get through her hang-ups. Up until mid-June 2012, it was going rather smoothly, as they had their honeymoon phase of official dating, kissed a bit more each time out and were relieved to not have as many complicated burdens anymore. Then it was right on cue for Annie to back away when Jeff got under her shirt, for Jeff to boil over a little bit, and for a few hurtful things to be said on each side.
A Jeff Winger who went four months without heavy making out or sex was extinct before now. Add on two years of trying to deny he wanted to have sex with Annie, then four months of admitting it and not getting to do it anyway, and it was startling he didn't act out until now. On the other end, Annie was going through all these psychological hang-ups just to have sex with someone who had sex with her evil mother; when he could have been sleeping with Annie a lot earlier. Both of them knew that Jeff didn't deserve that effort deep down, but their feelings for each other made them ignore that; although they were bound to have a slipup or two.
Since they were on summer break by then, they didn't even have a wacky, movie genre spoofing Greendale adventure to take their minds off their fight. So it took two days of stewing in their apartments, a lot of regret and a ton of guilt before they made up again. After about a week, they were back to their old routine and having fun once more, yet were both still nervous about the next inevitable fight.
The next one was hardly that bad in mid-July 2012, as Annie needed to use Jeff's laptop and wound up stumbling onto a rather nasty Internet history. Given that Jeff could only touch himself from now on, he had to get some weird inspiration to do it so he wouldn't take it out on Annie. That didn't lead to a fight as much as it made Annie creeped out for a day or two, and made Jeff angry and guilty over being caught. They brushed it aside with each other in almost no time, but for Annie in private, it was the last straw.
She couldn't really blame Jeff for cracking up under the pressure; although since he knew what he was getting in for from the start, she could try a little. But Jeff was doing everything he could to be patient and control himself, as it really was a miracle he'd done this well. Annie was killing herself trying to get through her mental blocks and just sleep with him, yet she clearly wasn't doing it enough.
On the other hand, the only sacrifice Jeff was making was not having sex; as if being like normal people and not having it every single week was a grave tragedy. Blocking out how the man Annie had crushed on for years slept with her rotten mother instead, and accidentally brought her back into her life for a few terrible days; that was the real cross to bear. And Annie was a veteran at being uncomfortable with sex stuff, so that was an extra bit of fun.
But Annie loved him. She could hate herself all she wanted for it every so often, yet she still loved him. She hadn't said it out loud yet, although Jeff clearly knew it was true. As much as it might make her sound like a naïve schoolgirl crawling back to someone who treated her badly, it wasn't true anymore.
For Jeff, going without sex was going above and beyond in a way he had never done in his life. He had beat himself up over the past 10 times worse than Annie had – not just for sleeping with her mother - and was desperate to get something right for her. He knew his complaints were trivial and kicked himself every time he made them; which almost made him fall right on his living room table when he tried to do it literally once.
Jeff was straining to keep his hormones in check, be a gentleman and actually say the right, romantic things; but he was trying, and most of the time he was succeeding. He would never do that for anyone but her, which showed just how much Annie meant to him; and admittedly, him being out of control from not touching her was a little flattering.
Annie was sick of making Jeff suffer long enough, let alone herself. Therefore, it was time to hunker down and grow a pair other than the ones on her chest once and for all.
For the next month, Annie set up an intense psychological exercise for herself. When she was in her bedroom, she willed herself to picture Jeff and her mother together in bed; and covered her mouth to muffle the screaming so roommates Troy and Abed wouldn't hear. But after the screaming subsided, Annie tried to imagine herself in her mother's place with Jeff. If she was going to stomach it in real life, it had to eventually get hot in her imagination first.
It took the first week just to put herself in her naked mother's place without spending most of her time screaming in her hand. The second week was spent imagining her and Jeff actually getting naked. The third week started slowly when Annie struggled to imagine Jeff and her mother actually….thrusting against each other. But she told herself it was necessary, so that it would mean more when Annie pictured herself thrusting against Jeff next. This did bring about a few nightmares; yet luckily Troy and Abed stopped being disturbed by her night terrors months ago, so they weren't suspicious.
By the start of week four, Annie knew she had to go one step deeper. Now that she was comfortable imagining her and Jeff….together, she needed to be aroused by it. Annie's sexual imagination had grown over the last three years, yet….arousing herself wasn't something she did on a regular basis, even when it came to Jeff. Her fantasies over him in the pre-Carol days were more romantic than sexual; but considering that this was Jeff Winger, some sexual ones did slip in somewhere.
Annie used some of those standbys to try and settle in, as she laid on her bed one night and let her imagination get more erotic than clinical. She drew on memories of their two kisses in freshman year, all those other times they were pressed close to each other, and all those lustful looks that Jeff tried and failed to hide from her. Then she moved into a little alternate history….imagining that Jeff was playing naked pool with only her as the audience, that Jeff did something other than say "relationships are complicated" in the men's room with her, and that her sexy Santa routine last Christmas was a little less babyish and got more grownup.
Soon, she even felt emboldened to think of how she made out with him right after her dad's funeral, for all the wrong reasons. As wrong and guilty as she felt about that for months, she was on such a roll that she willed herself to wish it was different. That she wasn't jamming her tongue down his throat just to show up Carol, that it had happened a few days earlier, and that there was no reason for her to pull back after 40 seconds.
Once that was established, it was easier to shift the scene to Jeff's bedroom…..easier to envision their funeral clothes disappearing….easier to imagine everything else off. When Annie imagined Jeff….making his move inside….she gasped for real and almost thought it was happening until she remembered her fingers had now….made the move for real. And after months of not doing this, months of waiting to be ready to fulfill this fantasy for real, and years of waiting for Jeff in general…..this was not going to take much longer.
Since Annie was a master at covering up her screams by now, she got her free hand over her mouth in the nick of time. She wound up letting out muffled screams for a good minute straight, while her other….occupied hand worked non-stop as well. By the end of that minute, Annie even noticed her hips were starting to thrust back against her hand; or she would if she could think.
Not thinking is the rarest thing in the world for Annie, but it was also rare for her to get herself off like this, especially since February. And that had now been accomplished and then some.
Annie would worry about feeling embarrassed, cleaning her hand off and wondering if Troy and Abed could tell that her "night terror screams" were different than usual. Right now, she wanted to revel in the fake afterglow of imagining Jeff inside her; especially when she realized she actually did it without thinking of Carol. Even thinking about her now didn't make her as horrified as she thought she would.
The point was she had finally imagined perfect sex with Jeff. Doing it for real was still another tall order all together; but that was why she had to schedule it soon before her erotic high wore off.
As such, after Annie thoroughly scrubbed her hand and wiped off her sheets, she finally got back to thinking. It was too late to call Jeff tonight, but she would do it the next morning and ask if she could come over his apartment that night. She wouldn't tell him the real reason why and get his hopes up too early, as she only stated she wanted to stay in for their weekly date. He would try in vain to find a movie they hadn't watched together yet, or one that she hadn't watched with Troy and Abed, and they would eat in as well. Somewhere in between, she would tell Jeff that she wanted to go into the bedroom, and hopefully…..the fantasy would play out the same in reality.
Annie didn't plan to dress extra sexy or do anything out of the ordinary that would tip Jeff off right away. So all she had to do to prepare was keep her courage up, keep her nerves from coming back and try not to think about how this might be the biggest night of her life. Since Jeff was the most important part of her life right now, and given how this might finally make their relationship move forward or kill it altogether, a lot was hinging on this. And now she was thinking about it, so that didn't help.
But Annie's will got back on track by the time she left for Jeff's. In the meantime, Jeff still needed a few internal pep talks.
He had finally made just enough food and gotten enough non-alcoholic drinks for Annie to last the evening. Jeff also made sure that his alcohol intake would be moderate, since if anything was going to happen tonight, it could not be under any influence. Drunken sex with Annie was pretty much the only mistake he hadn't made yet, and he preferred to keep it that way; it if nothing else.
Once again, Jeff had to tell himself over and over that he would not make another mistake tonight, and that he would make his hands behave. They had already gotten him in trouble twice this summer, and he wasn't sure sometimes that he and Annie were stable enough to survive a third. It was really a ridiculous fear, considering how well they were doing otherwise; but so much of this whole thing was ridiculous as well.
Jeff willed himself not to think it was ridiculous in the wrong ways; even though part of him still ranted and raved over Annie's inability to just get over it. Sleeping and having sex with him was not the same as when Jeff had sex with her mother, in so many ways. Sometimes he wished Annie would just see that and get naked already; after denying that he wanted to see her naked for two years, he really didn't feel like waiting for two more.
But then Jeff just had to remind himself that this was his fault to begin with. He just had to remember that he was the one who had sex with Annie's mother and made Annie's life hell the week afterwards as a result. Then he just had to feel guilty that Annie still wanted to be with him anyway, and was fighting to make herself want to have sex with him. This was precisely why he avoided guilt for the first 33 years of his life; back when getting women to take their clothes on for him wasn't remotely difficult. Those were some times.
Yet these were times in which the women he was with were of a higher quality. Times when he could be with the highest quality woman there was, in fact. When he allowed himself to realize that sex wasn't the only thing to revolve a relationship around. When he didn't want to have sex just to satisfy his own urges, but to make the other woman happy and give her some relief after all she had been through. And to show her in every way just what she meant to him.
These were thoughts that still made Jeff feel icky and lame sometimes, even when he just thought them to himself. But that was Annie's superpower, in making him do and think things he never would before. And look what it got him so far; it got him the best friend he ever had, a front row seat as Annie became even more amazing and grown up by the day, a rush of pride when he actually did something right and made Annie light up just for him, and validation that someone like Annie could actually care so much about him. He had done nothing to deserve it, yet Annie made him believe it a little more each time he doubted himself, even after they fought.
Jeff always needed some kind of sex to be happy with a woman until Annie. But even without it, they had been able to make out more and more over the months, so he wasn't completely deprived. Feeling her lips, tongue and embrace at least once in a while was both more than enough to pacify him, and enough to make him all too hungry for even more. Considering the unbearably sexy things he hadn't felt yet, even Annie couldn't blame him for not feeling….fully pacified.
But Annie did understand, just as she seemed to understand everything about him. It was just one of the reasons why Jeff still found her beautiful regardless of her looks; as jaw-dropping as they were. Those reasons were why he put up with all this, why he went out of his way to make her happy, and why he swore he would never push her away or disappoint her on purpose again.
As he heard a knock on his door, he still reflected on that even as he walked over to open it; since he knew who was on the other side. Once he opened it, he would make himself have fun and enjoy Annie's company, no matter how much touching he got to do. And he shouldn't have to make himself, because he did have fun and always would find ways to have fun with her, no matter what they did. He could find those ways simply because-
"I love her," Jeff unknowingly said aloud – and unknowingly said it right after he opened the door and Annie could hear him.
When he finally did notice her, he panicked and thought Annie would take it the wrong way, so he quickly corrected, "You! I love you, I mean, there is no her….." But it was in that moment where Jeff realized he spoke without filtering himself again; since this was the first time he said "I love you" to Annie out loud.
"There isn't? I mean…..you love me?" Annie finally said quietly. This certainly wasn't the way she pictured the night starting, even in her best fantasies.
"Well…..I guess if all these months and years didn't tell you, that should just about do it," Jeff said before he wished he had filtered himself that time. Even now, being sincere and heartfelt without adding one-liners or snark was harder than it should be. As such, he once again stumbled to correct himself, stating, "Or in simpler terms, I love you…..yes, I love you," he said a bit more honestly the second time.
Jeff wasn't nervous when Annie had nothing to say, since he knew she loved her without having to say it. In fact, she actually did it say almost two years earlier as part of a script to expose Dean Pelton's role in some convoluted conspiracies; although he knew it wasn't a script to her. But as Annie knew herself, she was in love with him in a more meaningful and deeper way now. Yet instead of saying so in words, Annie expressed it by coming over and kissing him deeply.
It took a while for Annie to remember that she wasn't planning to get carried away and have sex with him yet. If she still had nerves about it, she wasn't going to ruin this moment with them, at least. So she let herself make out with him for a safe period of a minute, hoping that it was a safe period for Jeff as well. But although he was holding her tightly and had a hand on her hair and another down her back, they weren't going any lower.
"So….hello, by the way," Jeff finally gasped out when they broke apart.
"Hi, Jeff," Annie said almost tearfully, before making herself get back under control for the moment. She wanted to settle down, eat for a while, get comfortable and then spring her intentions on Jeff. Fortunately, she spotted what Jeff had prepared and practically skipped over to start drooling over it.
Although Annie didn't have any extra words or even an "I love you, too" Jeff was convinced that she was pleased; and that she didn't spend 15 more seconds making out with him or he would have been a goner. They ate the first half of their dinner at Jeff's table, then sat together on the couch to finish it off and flip through the TV before putting on a movie. By the time that it was almost movie time, Annie put her pitch into motion.
"Jeff? I was already planning to say this before you told me you loved me, just so you know," Annie set up.
"I….believe you for now," Jeff quipped, in lue of trying to figure out what she could possibly mean.
"I think….I'm ready to try now." That didn't help clear Jeff up, so Annie tried to be more direct. "What I mean is I want to try….spending more time in the bedroom." Now this was officially sad; Annie's days of dancing around and whispering sex related words were over for a year now, and if they were back now, this would not bode well for the evening. So although Jeff was now putting together what she meant, Annie still blurted out "I want us to fuck tonight, Jeff!" before realizing she had wildly overcompensated.
Annie was usually the one left blushing and flustered at Jeff's words and innuendos, yet Jeff was the one taken aback now. After getting over the shock of hearing Annie say the f-word, he finally brought himself to ask "Oh….there's another reason I should have said I love you sooner."
"Jeff, I just told you that's not why I want it!" Annie protested before managing to steer back on course. "I've been preparing myself for a while, and I….I just think it's time we gave this a real shot."
"Okay….so what did convince you, then?" Jeff asked, wanting to stick to generic questions instead of blowing the mood with sarcasm again.
"Well, there's no better time than now, really. Look, in a month we'll start our last year at Greendale, and that gives us enough to worry about. If we try to have sex and fail, we'll at least have a month to recover and get back on good terms so we can come back on a good note. If we succeed, we'll have a month to celebrate and make up for lost time, then we can come back on a great note! Either way, we can't leave this hanging when we go back, and I figure we have just enough time now to recover no matter what happens." Jeff just nodded at Annie's clinical analysis, figuring it was best to smile and nod at the moment. "Oh, and the fact that I love you too played a small part in it," Annie added for effect.
Once Jeff was able to take that in, he carefully asked, "So….we're adjourning to the bedroom right now, then?" while trying not to sound too hopeful or not hopeful enough.
"No, we're in no rush tonight. We can just watch our movie, get comfy and get in the mood to make out, like always. Only this time….I don't want to stop at making out. Not anymore," Annie assured.
"Well….if that's what you want, then I have to be the good boyfriend and cave in. You're lucky I'm easy to bribe, Edison," Jeff joked and then once again wished he had a better understanding of when to make a joke. But after telling Annie he loved her, and considering Annie knew how to properly translate his one-liners, he figured he was still escaping hot water for now.
Annie confirmed it by getting their chosen movie into Jeff's DVD and then sitting back down to snuggle against him. They had only watched this film once before together, so they could at least have the pretense of focusing on it, remembering the good parts and making fun of the bad; instead of just working themselves into a panic over later. Yet this was designed to get them in the mood in the first place, so they had to give some token attention to the movie.
Jeff wasn't what one would call a natural cuddler, but it was part of the fun for Annie to break him down while they watched TV. She took her time getting closer to him, slowly putting her head on his shoulder and putting an arm around his waist. She could feel him stiffening up, but after she felt him for a few minutes, he usually softened up and tried to nonchalantly put an arm around her. After savoring how she was snuggled next to Jeff, and vice versa, Annie slightly tickled him by brushing her nose on the side of his neck. Once she caught him emitting a little chuckle, she kissed that part of his neck to fluster him a bit more. After Jeff turned to actually look at her and saw her smirking, with that special little Jeff-glint in her eyes, he was pretty much a goner.
Annie snuggled up a bit closer to help her lean in and start kissing Jeff once more, and they quickly picked up where they left off over 70 minutes ago. After the first few minutes where they used their tongues, Jeff made the move to slide his hand under the back of Annie's shirt. Once his fingers touched her skin, he waited for any sign of resistance, but she was still as playful with her tongue as ever. However, his fingers only stayed on her back for 10 more seconds before she finally pulled away.
Yet before Jeff could ask/groan if something was wrong, Annie reassured him by explaining "I think the main event should be in the bedroom." The faster Jeff agreed, the faster they could get there, so he got up – while only trying a little discreetly to pat down his groin area – and took Annie's hand to lead her to the bedroom.
When they got to the bedroom door, Jeff opened it and Annie stood still to take in the scene. This was the scene of dozens of Jeff Winger hookups; including the one with Annie's mother. Doing this right here would be the ultimate way to get this mental block behind her once and for all. So after getting her strength back up, Annie took a step forward inside; yet stopped when she noticed Jeff wasn't stepping in with her. Despite him leading her here, now he was the one frozen in place.
"I don't know what I'm doing," Jeff muttered before he seemed to know what he was saying. When he figured it out and saw Annie looking worried and confused, he knew he'd have to elaborate now. "I mean, I know what I'm about to do, that's fairly obvious. I'm just…."
"Now you're nervous because it's really about to happen with me," Annie hoped she understood. "I thought that was my job…..not that I'm not grateful to take a break from it." But this time Annie was the one lightening the mood at the wrong time.
"Annie, I feel like this is my last chance. I've done so many things wrong already, and if I screw this one up too…." Jeff worried.
"Jeff, don't blame yourself for this anymore, I'm the one who's been putting this off," Annie reminded him. "You had no idea you slept with my mother until it was too late, and you didn't make her try to take me out of Greendale. You didn't start kissing me after my dad's funeral either, you know. I'm the one who let it all get to me longer than I should have because I'm neurotic that way, and one of me is crazy enough."
"Granted, but still! I've waited so long for this….to get this right and make this perfect for you like you deserve. Now that it's time, I just….don't want to disappoint you in this too. I'm worried that I don't know how to really do that…it's not like I have the best track record," Jeff confessed.
"All we have to do is just do it and I'll call that a win," Annie promised. "Once we both get over our fears, we'll probably be off and running non-stop! It's just a problem of taking that first step forward, that's all."
"You know, when I pictured this before, I was either wowing you with my sexual brilliance, or you were wowing me by being a hidden sex expert," Jeff recounted. "But now in reality, neither one of us is the expert and we're both equally nervous. There's something sad and reassuring about that."
"I know….we're actually on the same page for once, but it's not the page we want. We just have to think about something better than our hang-ups….and I guess our naked bodies won't do it quite yet," Annie conceded. At the least, this put her back in her natural element; thinking and over thinking to solve a problem. And suddenly, it hit her.
"I've got it! Sit over on the bed!" Annie was getting swept away by whatever idea she had, so Jeff had no wiggle room to actually ask for clarity. He just sat down on the right side of the bed and waited for Annie to explain herself, but she was busy heading for the bathroom. Instead of actually….using it, Annie stopped in front of the second largest mirror Jeff had in there, and seemed to be playing around with her hair.
As it turned out, she was doing her hair up until it was in the same pulled back style it was in her first weeks at Greendale. "I thought the point of this was to take things off, not pull them back," Jeff questioned as Annie hopped back in front of him.
"Do you remember the last time my hair was like this?" Annie inquired. Recalling his memory wasn't the best skill Jeff had in bed, so this would take a while. But as he searched through his Annie archives all the way to the beginning, it came to him. "Debate preparations…" was all Jeff had to say to let Annie know he got it; referring to the night in fall 2009 that they first noticed each other in a non-platonic way.
"I let my hair down for the first time at Greendale when we prepared for that debate. And that was the first time you noticed me as more than just a little girl, a new friend or a study partner. Shirley and Abed made us think we would kiss five seconds later and that's when we got awkward….but before that, letting my hair down was the first time we really had a true moment. It was one of the few moments we've had that didn't have stupid complications, awkward feelings or repressed emotions buried underneath…..and it was the first time I realized that someone thought I was beautiful. That's how we really began….and this is where it's all finally paying off."
Jeff let those memories, and what Annie pointed out they really meant, flood him as Annie sat down next to him on his right. "Those are the memories that I really want to think about tonight, Jeff. How far we came from that little, perfect moment and survived every stupid one that came after. So I think it's perfect that I pay homage to it now….before I kill the image of me as a spinster librarian once and forever."
As she did over two-and-a-half years ago in the study room, Annie reached over and undid her pulled back hair as Jeff was enraptured. And like back then, Jeff had nothing to say as Annie shook her hair loose and let it cascade down to her shoulders again. When she did it back then, it was the first sign of Annie loosening up to become a slightly less uptight, more open and more grown up young woman. As she took in how far she had come since then, it made her light up gently as the courage, hard-earned wisdom and love she had gained from the past three years overpowered her nerves.
"What do you think?" Annie asked just like she did on that night. Jeff was fully intending to say "Yeah" just like he did back then; yet instead he said his actual thoughts out loud, which were along the lines of "Just that you're the most beautiful woman I've ever seen." Apparently the sight of Annie letting her hair down was even better with age, as it made him return to saying sappy, sentimental things he was embarrassed to let himself say out loud at first. He said lines like this regularly to pick women up; but it was different when it was absolutely true in this case.
Jeff's uneasiness at being cheesy was derailed by Annie's even brighter smile, as it always was. It was bright with both his admission and his comical embarrassment over letting it slip out loud. And that was as good a cue as any to finally get going.
For the third time, the two embraced each other and began to make out, yet even more passionately than before. After Jeff got to savor feeling that tantalizing hair in his hands, he slid them down and prepared to start moving them back up under her shirt again. Yet Annie had beaten him to it by placing her hands at the bottom of his shirt and beginning to creep up underneath.
Jeff wasn't one to pass up an opportunity to be shirtless, and he wasn't going to dare change that now. Unfortunately, this meant he had to pull his lips and tongue away from Annie, yet he tried to tell himself it was worth it as he got the distance he needed to remove his shirt. Annie had seen him shirtless more than once; and peeked at his entire naked body playing pool two springs ago; but seeing it this close and in this context was a far different matter.
The abs, muscles and taut flesh that had haunted Annie's repressed erotic memories were now right there for the touching. Annie tentatively placed a hand on each of Jeff's biceps, amazed by the feel of them and how her petite hands looked on top of them. She then put her hands on his bare chest and slowly slid them down, focusing on their trajectory and not how Jeff was catching his breath at Annie feeling him up.
"We've joked so much about your insane health care regimen….but if this is the result, I'm glad you're crazy," Annie admitted as she trailed a few fingers over Jeff's abs.
"Glad that you finally appreciate it," Jeff stated in more ways than one. While Annie was distracted, Jeff took the time to start his own examination, as he pulled Annie's shirt half way up before she finally noticed and decided to finish the job herself.
After throwing her shirt away, Annie watched Jeff intensely examine her; mostly on how her upper half was only clothed by a blue bra. Annie knew she wasn't playing fair by now having both her eyes and chest – Jeff's two favorite physical features on her – surrounded by the color blue. But that was exactly the point, and Jeff seemed to like her cheating in this case.
Jeff pulled Annie back against him, as their bare flesh was now touching for the first time. He let himself fall on his back and let Annie lay on top of him as they kissed again, mainly so his hands could better explore her bare back. As he finally reveled in their skins rubbing together and his hands doing some rubbing of their own, Jeff's lips ultimately left hers and went down to her neck.
Annie responded by putting her left hand through his hair and pressing his head even deeper against her neck, while her right went back to trailing over his arm and chest. Jeff's own hands went up higher on Annie's back, until he could more clearly feel how her chest was crushing his; a chest he had a pretty good downwards view of from this position.
"Ah, the other things I noticed for the first time on debate eve," Jeff commented, as that night was also the first of many times he noticed her cleavage and got flustered about it; but that failed modesty wasn't needed now. He backed away to lie back against the bedroom wall, intending to start removing Annie's bra once she sat up in front of him. But when she got there, Annie shook Jeff's hands off her back; which made two other things shake a bit and sufficiently kept Jeff distracted.
Annie stated, "I've got this," before reaching her hands back to start unhooking her own bra. Once she finished, her hands came back in front and slowly peeled the bra off. She took a deep breath; without intending to push her chest up further in the process; and then unveiled her breasts to her boyfriend for the first time.
She expected Jeff to attack them right away, but instead she found him just staring blankly at her assets. If she didn't know better, she'd swear that Jeff was truly speechless at them, which shouldn't be that likely. Jeff had seen countless breasts over the years, and surely he had seen bigger ones than Annie's. Yet Annie had to admit he probably hadn't seen many which were that bigger than hers; although that still didn't explain why he looked at them like they were the first he ever saw. He was looking just as overwhelmed as Annie imagined she would when she saw his….equipment in a few moments.
But after Annie had gradually shown more of her chest in the last three years, she imagined Jeff had a vivid imagination about it. Now it seemed it was living up to the hype and then some, which actually filled Annie with pride. Despite all the naked breasts he had seen over at least the last 20 years, Annie's C-cups were reducing a breast connoisseur like Jeff Winger to a puddle of goo. She felt almost empowered; although this made her have to ignore the Britta voice in her brain about how this was hardly female empowerment.
Nevertheless, Annie finally giggled and broke Jeff's concentration, then pushed her chest up a little more. "Go ahead," she softly insisted, ready for Jeff to do more than drool over her boobs. Finally he let himself grab both of them gently, then place her left nipple in between his fingers before leaning in to nibble on it.
After his initial taste, Jeff started to let his mouth taste more of her breast, opening it up more as his left hand pushed her boob up. His right hand palmed her right breast and covered most of it, which spoke to how big both his hand and her breast were. Annie now let herself moan as Jeff kissed and nipped as much of her left breast as he could before suckling it into his mouth again.
"Your mom has nothing on these," Jeff actually said against Annie's boob. But as he cursed himself for saying precisely the wrong thing now, he noticed that Annie wasn't cringing or pulling back. In fact, he thought he heard her moan deeper, and began to wonder if she made out what he said. Yet considering that his mouth was full of Annie's ample bosom, there was probably no way he was speaking remotely clear.
"No, big boobs really did skip past your mom's generation," Jeff commented right against Annie's breast to test this out; and the vibrations from his voice seemed to really get her going. So much so that she didn't notice what he actually said; as if she could have understood him. But the humming against her breast was all she could focus on; which would surely happen to Jeff when/if Annie hummed with a….sensitive part of Jeff in her mouth later.
For now, it seemed Jeff had found the perfect way to muffle whatever douchy, unromantic comments might slip out to ruin the mood; and in a way that would actually heighten the mood for Annie. "Wow, saying the wrong thing isn't always stupid after all," he said unintelligibly with his mouth covering Annie's nipple, and an extra lick to it afterwards really got Annie to groan. But with that, Jeff decided he shouldn't waste his vocal talents on saying stupid things against her boobs; at least until the next dumb thing almost slipped out.
Jeff reluctantly slipped Annie's left boob out of his mouth and finally got around to use it on the other one. As Annie continued to grit her teeth and groan, Jeff trailed his left hand down her now free breast and then brought it down to her waist. He searched for the zipper on her skirt and ultimately found it, pulling it down and ghosting the side of his hand over her backside. Once Annie actually noticed Jeff's other work, she focused enough to finish pulling her skirt down herself, leaving her with only her panties on.
"Oh God…..I'm guessing you never did that with Mom," Annie got out, feeling good enough after all that to actually mention her dying demon. Jeff put his mouth back on her right nipple and just moaned "Nope" as a final teasing hum, before resting against the bedroom wall again and giving his busy mouth a rest.
Annie sat right in front of him, then impulsively bent down to give both his nipples a playful kiss. It was the least she could do after his nipple work, and she hadn't forgotten the rumors of his own nipple play fetish. Judging by how Jeff caught his breath again, Annie was wise to remember those rumors. So she decided to keep going and kiss his nipples once more, then go up to his upper chest and start kissing it as well. She then kissed down a bit and looked up to see Jeff's reaction; which was improbably getting even more undone.
"Annie….if you're going to keep kissing me like that, I will need you to keep looking at me," Jeff let out. Annie was a little puzzled, temporary looking down as she kissed his chest again, only to see him all but bite his lip when she looked back up. "Yeah, something along those lines will do," he let escape.
Out of all the Annie fantasies Jeff actually let himself imagine in bed, a recurring favorite involved her looking up at him in some fashion. Often that was while she was on her knees and doing a special job, yet anything that had her staring up at him with those wide, ungodly gorgeous blue eyes would do. While she wasn't on her knees in this case, as long as Annie's sweet, now increasingly erotic peepers were gazing right at him, Jeff would be reduced to sheer putty; like he was by them almost every single day.
Annie was starting to be aware of this effect, so she zeroed her focus right on Jeff's eyes as she kissed across his abs. With this latest example of how little, inexperienced Annie was indeed mastering control over professional skirt hound Jeff, her eyes, lips and hands were taking on a more devious approach. As her eyes darkened and she even started to use her tongue while kissing his lower chest, her hands made their way onto Jeff's pants and started to dispose of them.
Jeff got enough control back to slide his pants down when Annie had them unbuckled and unzipped. After Annie helped get them all the way off, they were both just left in their underwear; yet Annie decided Jeff was still over dressed. With a deep breath, she grasped each side of his underwear, closed her eyes and pulled it down; then opened back up when she was fully prepared to see what had been unveiled.
Now it was Annie whose breath was caught, as she saw the object that had teased her imagination for so long. It was fully erect and sticking straight up, about one or two inches longer than her initial projections, and looking fully and utterly engorged. Annie had no words to describe seeing it, but maybe she would find a few more when she touched it.
"Annie, wait!" Jeff called out before she could test his theory. "I don't think you should do that."
"How is it sex if I don't touch it, Jeff? I did my research, I know what I have to do," Annie reassured.
"Yeah, but after all we've done here and all this waiting…..you'll probably accomplish your mission really quick," Jeff tried to allude to without outright saying it. "Look, I do last quite a while under normal circumstances….but these aren't normal ones, and they aren't usually this hot either. So I think we should….jump to the main event while I can still do it."
That was innuendo that Annie managed to understand, as she gasped in recognition. "Oh….the main event. Well….I said I wanted us to fuck tonight and here we are," Annie said, glad that she again suppressed her instinct to merely whisper the f-word or use an abbreviated version. This was a sign that she was still ready for the final test.
Jeff needed an extra minute to give his erection time to settle down. Even with that, he knew that once he sunk into Annie, it would not take too long to ultimately blow. She had the limited sexual experience and yet he was the one worried about coming too early like a virgin; but at this rate, he would have a lot of time to make up for it. For this first time, it was just about helping Annie get over the hump, even if he could only do it for a few minutes.
When he was set to go, Jeff went over to his desk drawer of condoms, as he was not taking the chance of messing up on that end. In any case, if he wasn't going to last a long time even with a condom on, he feared he wouldn't last a minute unsheathed inside Annie. As for Annie, she passed the time and attempted to keep her nerves from coming back by removing her panties, leaving her fully naked by the time Jeff got his condom on and turned back around.
Being greeted by the sight of an entirely naked Annie for the first time, lying on her back and in position to go…. "Yeah…..this is not going to be my longest work," was all Jeff could say to that. All he could hope for was that Annie was just as worked up and could….lose it at or around the same time he did.
For her part, Annie was filled with so many thoughts; even for her; that she didn't know what to feel. The anticipation, hope, nerves, fear and good and bad memories were all colliding together in her, leaving her a little bit numb. But as Jeff crawled back into bed and settled on top of her, Annie forced herself to actually stop thinking. If she thought too much, her mind would wander back to how Jeff laid her mother down in this position, or one like it, in this same bed months ago. And that was not how Annie wanted her first time with Jeff to finally go after all this time.
Something had to make her stop thinking about that or anything else; and that something was now starting to push into her.
Annie may not have been a virgin, but the feeling of someone else inside her was still rare enough to hurt a little. However, even now Annie still thought fast enough to know that Jeff wouldn't keep going if he thought he was hurting her. So before Jeff could say anything or pull out, Annie waved him off and signaled for him to keep going while she adjusted to him.
She kept her face from showing any more pain as Jeff got halfway in, then decided to pull out and then back in for an experimental thrust. This made Annie groan a little bit, so Jeff figured he was on the right track. He still wouldn't go in all the way yet, so he slowly thrusted a few more times while he was halfway inside. Annie shifted her hips a bit to keep adjusting to Jeff, yet that only made her feel tighter around Jeff and made him thrust a little deeper and faster. They had to work out the exact mechanics for a few more moments before Jeff finally settled into a steady rhythm.
Annie now let herself reflect in wonder that she was really doing this, as the pleasure stared to flood through her. But she didn't want to just lie there while Jeff did all the work, as she moved her arms up to drape around him and pull him into a deeper embrace. His head rested on her neck while her hands started to trace up and down his back, savoring his muscles once again. And now the muscle that was pumping inside of Annie was inching all the way inside of her in the meantime.
Jeff finally sank himself completely into Annie, which made them both pause to savor the milestone. Annie clamped her legs around him to fully take it all in, and Jeff had to keep himself under control as Annie's insides completely surrounded him and were putting even more pressure on him. As he got moving again, her legs clamped onto his thighs for dear life as she took more and more of Jeff in.
With Jeff head still lying on Annie's neck, her moans, pants and the occasional "Oh God" were being placed right near his ear. So not only was the feel of Annie bringing him closer to the brink, the sound of her wasn't helping either. He could silence her by kissing her, but she would likely still be moaning and the vibrations into his mouth would probably end it then and there.
Annie wasn't trying to bring him closer to climax, as she was just trying to take in everything she could. She clung to him below him and even started to move her hands lower to get a better grip. They soon grabbed onto his hips and unconsciously helped push Jeff in even deeper.
After a while, he seemed to be trying to slow down and pull out a bit more. But when it felt like he was almost out all the way, Annie acted on instinct and slammed herself right back up against Jeff to get him all the way back in. Now Jeff was the one groaning right into Annie's ear, especially when he almost pulled out again and both of their hips slammed right back onto each other this time.
Annie hoped that Jeff got the message, and it seemed that he did as he didn't try to pull so far out again. So she clamped her legs back around him and put her hands back on his hips, as she soon groaned and grimaced back in his ear again. She even caught herself using the f-word again during one particularly hard string of thrusts. After that, she could have sworn that Jeff's groans were getting louder than her own.
Before Annie finally focused enough to start kissing Jeff's ear and face, he lifted his head from her neck and started to stare back down at her. She was expecting to see him cocky and confident after he saw what he was doing to her, yet Jeff actually looked more undone than she might have been right now. In fact, he was gritting his teeth even more after seeing her and had started to thrust a little more wildly. Once he did, Annie barely kept her eyes on him as Jeff kept burying himself to the hilt; and then the thrusts suddenly stopped.
Since Jeff had a condom on, Annie wouldn't be able to feel what he was releasing inside. However, it was becoming clear that he was….finishing himself as he completely stiffed up above her. He seemed to be trying to get inside her even deeper, while his face was clenched tightly enough that Annie had to stifle a little laugh. But just as suddenly, he loosened back up and literally fell on top of her as he tried to catch his breath.
Annie rested her hands on his upper back to feel him breathing quickly, as she took in how she had made him that out of breath. But he could still talk even then, as he gasped out, "Did you….did you go too?" Now that Annie was starting to think at normal speed again, she did a quick analysis and realized "No….no, not yet." And now that Jeff was probably going soft….although it didn't feel like it yet…it seemed like she wouldn't be able to go off in this position.
"Uh uh. That laziness won't do….not this time," Jeff panted out. Before Annie could ask him to clarify, she suddenly felt him pulling all the way out of her. He then even got up from up above Annie and slid down her body. Before she knew it or could even guess what he was doing, she looked down to see his head settling in between her legs – and to feel his lips in between them as well. A second later, his tongue was clearly joining in the act as well.
"I never even bothered to do this with her," Jeff said right up against Annie's opening, wondering if the vibrations would drive her crazy down there too. Since this area wasn't as big and supple as her boobs, Annie could have probably made out a few of Jeff's words this time; if they weren't drowned out by her moaning.
At that point, Jeff wanted to stop playing games and get Annie to the end. And Annie was certainly feeling close; she may not have been as close as Jeff when he was inside her, but she did feel like it was coming soon, to coin a phrase. Now that she could feel his lips and tongue in her, it was taking all she had not to come too quickly too. But when Jeff raised his hands up to grasp her boobs and he looked up at her in the same way she had done, Annie's usually indomitable will crumbled.
Her hips shot up right against Jeff's mouth as Annie let out her loudest series of groans. But when she felt herself….come undone, she had just one loud moan left in her, which faded in volume very slowly as her release winded down. Finally she slumped back down, closing her eyes and catching her breath; barely even feeling Jeff's tongue still on her.
She had only a few moments to reboot herself before she didn't feel Jeff's face on her groin anymore. He was crawling back up on top of her, but Annie snapped back into action when he tried to kiss her. "Jeff, ew! You're going to kiss me after you tasted my….." Annie trailed off trying to find a euphemism for her cum. Then she gave up and insisted "Brush your teeth first! I'd like to kiss you tonight and only….well, taste you!"
Annie briefly cringed, thinking she had ruined the moment by being old neurotic Annie again. And yet after a few seconds, Jeff just laughed, as it seemed he did appreciate that even after all that, she was still the same old Annie. Yet he teased her by nearly kissing her lips after all, but settled for her cheek before getting out of bed to clean himself up.
Slowly, Annie started to feel like herself again as her orgasmic high came down. Then it hit her that she actually had an orgasmic high to begin with. "I did it….I really did it…." Annie reflected, as the fact that she had gotten over the hump fully hit her. Jeff had sex with her mother, and yet she had brought himself to have sex with him in that same bed anyway. And it was…..certainly something.
She even put Jeff's last audible comment into proper context, as he said "that laziness won't do" because he didn't want to just settle for getting himself off. He made extra sure that she reached the same heights too, although it came after he did. But considering how Jeff was the expert in this area, and yet he had exploded first….Annie liked to believe that wasn't just because it had been so long for him.
Not only had she gotten through her first time with Jeff, she had made him come probably a lot sooner than usual. Even Annie knew that being quick like that was usually embarrassing; but not when someone was so turned on and enamored by his partner like Jeff proved to be. The fact that Annie could inspire that was quite a boost to her ego; one which was often as big as Jeff's was, although….he had some other big things to help him recover anyway.
Speaking of which, Jeff emerged from the bathroom with his teeth apparently brushed, and the condom now off his formerly wet and hard erection. But even though it wasn't hard anymore, just seeing Jeff stand up in this full frontal state made Annie's….baser urges get back up. She loved Jeff for who he was on the inside; as much as Jeff thought that was impossible sometimes; so Annie could justify ogling him like a piece of meat right now. At the least, it made them even after his little ogling of her eyes and breasts.
"I want to go again…." Annie found herself saying once she looked back into Jeff's eyes. It hit her just why that was as Jeff commented, "Ah….so it seems sex addiction is a sexually transferred disease after all." He then cringed a bit at using those types of words, muttering "Damn, I should have said that into the boobs."
"Jeff, I'm not a sex addict now," Annie pointed out. "But I just got hooked. I really did it after all this time….and now I can do more. I did this to prove that I could do it, and now I can do it for fun."
"So that wasn't fun? I knew we had different meanings for fun since the day we met, so I can't say I'm shocked. Hurt maybe," Jeff quipped and hoped Annie took it as just a quip.
"Jeff, that isn't what I mean. We took that first step forward, and now we can have regular old sex. No awkwardness, no waiting, no trying to hold back demons or bad memories…..we know what we're doing now! And since we both just….got off, we can make the next time last longer. It'll be like…." Annie hesitated before she could say "making love" since her own instincts to not be too cheesy kicked in. Instead, she said "Like sex between a regular couple….and that's what we finally are now."
"We might have different definitions of normal too, but I get your point," Jeff conceded. "Well….if you really want to, it's going to take me a while to…..get ready to go again," he said, pointing down to his soft tool. "And we kind of need him to be at full strength before show time."
"Okay then, this is a problem. But I'm a good problem solver," an emboldened Annie proclaimed before getting out of bed and walking over to Jeff. He wondered what she was setting up, until he saw her take a breath and go down on one knee in front of him. A moment later, she was on both of them.
"Annie, wait," Jeff let out while he still had the mental capacity to check if she was okay with this. Yet it deflated quite a bit when Annie took a tentative hold of his shaft.
"I didn't get to do this before because you thought you'd lose it. But you just did that a while ago, so it should be able to handle me now," Annie theorized.
"In theory, yeah…." Jeff admitted, although he was starting to doubt it.
"Well, I like testing theories, you know," Annie reminded. "And you were so thorough and fair with me before, Jeff. I know you think you haven't been fair with me until now, but you really are…..more than both of us might give you credit for sometimes. You came through for me in the end, like you always do….and now I want to make us even."
Annie started her quest by experimentally stroking Jeff once, then bending her head down to give his little head a little kiss. But it was starting to grow again, and when she kissed it once more, it stood straight up and made Annie pull back a bit and giggle. Once it was approaching full mast again, Annie leaned back in and kissed it again, adding a tiny bit of tongue before breaking off.
Not for the first time, Jeff contemplated how he was the one that could never make things even with Annie; whether due to his screw ups or her being incredible. Although she obviously was new at this, the feel of her mouth starting to surround him was making up for it; as if he didn't already know how warm and silky it was from all their kisses. Nevertheless, Annie's mouth won him over anew as it started to open up and take more of his head in. She added her tongue again when her lips got to the bottom of his head, then suckled a few times in earnest.
Impressed, Annie hummed her approval, the vibrations of which made Jeff hum out his approval as well. "Annie…." Jeff called out, which for some idiotic reason made her take his mouth off his member. "Oh right, the eyes, sorry!" Annie misinterpreted, yet it was just fine as she suckled his head again and made Jeff almost sink to his own knees once her perfect eyes stared up at him once more. Seeing them look up at him while Annie kissed his chest was one thing, but this was above and beyond.
Jeff tried to stop himself from looking at her every few seconds, although he could still clearly feel her mouth taking more of him inside. When he felt brave enough to look back down, he tried to look at more than just her deceptively innocent mouth and eyes. Soon he began to notice her entire face, and how serene it was becoming. A relaxed Annie was so rare, and Jeff had figured that this would reactive her nerves and over thinking, yet it was different here.
Now that she had faced her sexual fears once and for all, Annie did appear calm although she was bobbing up and down someone's penis for the first time. But the same old Annie was still there in her eyes; just not the neurotic sides. While her amazing blues were getting more sexual, there was a familiar pride and warmth in them; the pride she felt when she had gotten something right and was making someone she cared about happy, and the warmth she showed him whenever she was in Jeff-adoration mode and was truly proud of him. This combination made Jeff reach over and stroke her cheek and hair, instead of trying to just push her head down his length; another way in which Annie inspired behavior in Jeff that he'd never shown for anyone else.
Annie showed an even deeper mix of warmth and sexuality in her face and eyes as she fit almost all of Jeff into her mouth. This made Jeff stammer "Okay, I think show time's just about ready now!" as his fears of letting loose early made a surprising comeback.
"Oh, okay then!" Annie said with her chipper tone, as if her mouth hadn't been filled by Jeff's raging hard on seconds earlier. She even got back onto her feet and gave him a few kisses on the lips as well.
"So it's okay for you to kiss me after something of mine's been in your mouth, huh?" Jeff pointed out in hopes it would help him compose himself.
"That's different, you had….my juices in your mouth!" Annie said carefully. "I stopped before….yours got in me!"
"Well, maybe this time," Jeff warned, which made Annie actually give a scandalized blush for the first time tonight. Yet by the time Jeff went back into his condom drawer, wrapped himself up again and sat back down on the edge of the bed, Annie recovered and maneuvered herself to sit on his lap; among other things.
"Just fuck me first, okay?" Annie asked, as if she was asking for any normal thing on any other day.
"You need only to ask, milady," Jeff responded in words. In actions, he responded by guiding Annie back down as he entered her again.
Although Annie had brought him back into full strength fairly quickly, Jeff was confident that he would be able to last inside her a good long time now. Then again, this was a new position they were in, as Annie was now right on his lap with her perfect, shapely breasts bouncing in front of his face; and her perfect, shapely backside bouncing on his lap as well. This reminded Jeff to actually grab a hold of that other round, seductive feature of Annie's this time, as he held onto her ass while she started to get a hang of riding him.
Like Jeff said, he had imagined that their first time would either have his expertise reduce Annie into a puddle, or her learning on the job well enough to turn him into goo. In truth a little bit of both had taken place thus far, as they had gone back and forth between being in control. But now they were each on the same wavelength, as they were both on the top of their game and pleasing each other in equal measure.
Annie was now moving her hips up and down Jeff's shaft instead of just clenching around it, and even pushed her chest forward and pushed his face in deeper when he went back to work on her cleavage. Jeff did his share of groping her ass before his hands started to work with his shaft in getting Annie going again down below. They also spent a fair amount of time navigating her waist, back, hair and breasts before Jeff was finally ready to change positions and lay Annie on her back again.
With the two back into missionary position and ready to near the finish, Jeff was able to pump into Annie without worrying about her nerves, how long he would last and whether he would say the wrong thing. He was now able to just focus on bringing his girlfriend overboard before he was ready to shoot again.
But he wasn't just trying to bring his girlfriend off; he was also bringing off his partner-in-crime, his best friend, his conscience, his role model, his worthy adversary, the kindest, bravest person he'd ever met, and sometimes the most painfully flawed as well. All of these Annie's made the months and years of waiting for this night go down so much easier; and now they were making the wait more than worth it.
"Oh, fuck me, Annie…." Jeff wound up saying after she gave him a particularly deep suckle on his earlobe.
"You need only to ask, milord," Annie answered back, now that she was having fun with this.
Jeff renewed his quest to get Annie off before he did this time, or at least bring her overboard before he got too soft. He got his hands back into the mix by dipping one down to her filled opening, while the other lightly trailed up her hip and all the way up her body. Yet while Annie was appropriately flustered, she still had enough to raise her hips back up and thrust against him rapidly.
The two went back and forth like this for a few more minutes, as they started kissing again, traded taking command and were in sync with what would bring them over the edge. Considering how overdue they were to finally be in perfect sync, this was a good time to actually get it right. But now that Jeff was fully back in his sexual element, he would be the one to take Annie over first this time.
With a few final little pinches down below, Jeff just waited patiently for Annie to tighten up and give another long, loud final scream. She started it by trying to yell his name, but it eventually devolved into a regular yell as she let herself go. Jeff temporarily stopped thrusting to savor Annie's tight grip, then as he watched her face start to relax a little bit and savor her orgasm, he went back into action once again.
By focusing just on Annie's post-orgasmic face, her even warmer and wetter opening and how he was already close to finishing as it was, it was the right combination for Jeff to fill up his second condom of the night.
But after this longer and exhausting session – and how it had actually gone just right – Jeff immediately knew he wouldn't have enough strength to fill a third. All he could do was finally fill up to the brink, collapse against Annie's chest, pull out of her and wonder if her boobs really could be used as pillows.
The next time he had a thought was the next morning when he finally woke up. His temporary pillows were gone – and so was the rest of Annie.
Jeff looked around and made sure he was alone, then when he confirmed it, he saw that he was naked and that his condom was off. For a minute, he was groggy enough to think he had dreamed it all in his most extensive Annie dream to date. He certainly didn't put it past him to have gotten himself naked to heighten the experience.
Not being sure what was real at the moment, Jeff willed himself to get up and try to search for clues outside the bed. He went into his closet and got one of his robes on, as putting on his clothes from last night, or any regular bed clothes, seemed too hard and time consuming at the moment. With the extra time, Jeff was able to leave his room about 25 seconds earlier – right on time to see Annie sitting on his couch in her clothes from last night, bright and awake already, of course.
"Good morning, Jeff," Annie greeted, which temporarily gave Jeff his own flashbacks from his morning after with Carol Edison – although at least Annie didn't call him Jeffrey. "Sorry I didn't get you up. I spent so much time washing my hands after getting your condom off, I just wanted to get dressed and get out of there. I would have taken one of your robes, but I figured that might be too creepy."
That was too creepy, yet removing a full condom for him while he was sleeping and then likely scrubbing her hands into oblivion was fine. But that kind of over commitment, attempts to be considerate and ability to still be grossed out was pure Annie; so sex hadn't changed everything.
"How long ago did you decide that, exactly?" Jeff asked. "Probably about 20 minutes ago. I lost track of time looking through some of your pictures," Annie explained, holding up some photos Jeff had lying around of him, the study group and Annie. She knew full well that her mother found these pictures the night after being with Jeff, then tricked him into giving up information about Annie and was inspired to try and force her out of Greendale over 24 hours later.
But after the milestones Annie reached last night, she was more ready to make fun of what happened than be screwed up by it any more. Besides, there were some new pictures of Jeff and Annie from the last several months that she could savor as well.
"One of these days I'll learn how to reorganize those," Jeff commented, carefully playing along. "Those are my friends, all right….would you like to know more about the sexy brunette first?"
"Nah, I'm not in that much of a nosy mood…..kind of wore myself out too much last night. I'd rather find out if my sexy boyfriend has any plans for today so far," Annie inquired.
"Okay….usually after nights like this, I find ways to be alone or I get myself up for round two. Or three in this case. But I'm still a little tired and I'm kind of co-dependent at the moment…..so maybe morning-after breakfast would be a nice change of pace," Jeff pretend to concede.
"Great! Let me find some cereal or eggs, or some other third thing, and I'll be set for that too!" Annie perked up, getting up and pecking Jeff before heading into the kitchen.
Annie expected to find eggs quicker than any cereal, but the search also gave her an excuse to gaze at Jeff as he sat on the couch and struggled not to fall back to sleep. She was still amazed that she was here, looking to see if Jeff would fall back asleep before breakfast. Looking to see if her boyfriend, whom she spent the night with after having exhausting sex, would go back to sleep.
Jeff had been her boyfriend for months, but now there was no asterisk to it anymore. Now that their final obstacle had been overcome, he wasn't just her boyfriend who once had sex with her mother. He wasn't just an older man who fought being attracted to her tooth and nail for two years. He wasn't the jackass who was too afraid and slightly self-loathing to accept being in love with her either. And she wasn't Little Annie Adderall, a child with a schoolgirl crush, an inexperienced seductress or someone ill-equipped to handle a real, adult relationship.
All they were was Annie Edison and Jeff Winger – no more, no less, and all the amazing things that entailed. Of course, she knew they were still that regardless of whether they had sex or not, but now there were no more asterisks. And as Jeff just illuminated, sex wouldn't be the defining aspect of their relationship even now – just one more additional perk along with all the other things that made them love each other.
As much as Annie might hate to admit it, none of this would have been possible if Jeff hadn't hooked up with her mom, or if she didn't try to ruin Annie's life two days later. Without that, Jeff might have stayed in denial about how he felt up to graduation or beyond, and Annie would not have learned how to make a true relationship with him work. By those revelations, Jeff sleeping with Carol Edison was the greatest thing that ever happened to Annie.
But it wasn't like Annie was going to call Carol and tell her about that – not even to gloat. Since they didn't bite each other's heads off after their last meeting, Annie didn't feel like ruining that by gloating how she landed Jeff anyway, how Jeff came to deserve her, and how unlike her mother, Annie was getting to stay at Jeff's the morning after and probably many many more after that.
Well, she would be lying if she didn't feel like it a little.