This is based on a fic prompt at the Milady/Milord Jeff/Annie community from a member named teruel_a_witch, who asked for a fic starring "possessive Jeff" after he sees everyone drooling over a sexy Annie at a party – while they are in an actual relationship. That means he can do something about his jealousy, which you will see in smutty detail below – as if I didn't have enough smut in my last story.

When Jeff finally let himself get together with Annie, he thought he was done feeling uncomfortable about ogling her – or feeling anything other than lust when he did. But of course, Annie couldn't even make that easy for him.

Four months into their relationship, Jeff took Annie to a party hosted by his old law firm. With their final year at Greendale almost halfway over, Jeff was planning ahead for once and thinking about where he'd work after graduation. His old firm was certainly an option, but there was no harm in enticing other firms before he decided.

This event would help the process, as guests from those other firms would be there. More personally, it would be the first non-Greendale party he and Annie attended by themselves as a couple. Of course, Annie had dipped her toe in Jeff's lawyer world two years ago, which ended with her going on a chloroform spree. But Jeff made sure she left her chloroform at her apartment, and was confident that his old social circle wouldn't kill a friend's morality this time – especially since Alan was on vacation.

So Jeff was feeling very confident about the evening – until the second he saw Annie in her little blue dress.

While Jeff went with his typical suit/tie combo, Annie had gotten an atypical strapless blue cocktail dress for the occasion. It hugged every delectable part of her body that it could – and there were many of them – while highlighting the delectable parts that weren't covered, like most of her legs and the tops of her breasts. And since it was blue, it did the impossible in making Annie's blue eyes even more enchanting. She didn't even have to put eye shadow on them, although she did touch up her lips and hair to make up for it.

Jeff allowed himself a good 20 seconds of speechless gaping, until it hit her that he wasn't the only man who would see her like this – far from it. Before Jeff could mention it out loud, Annie came out, pecked his lips, complimented his attire and asked to be escorted to the car. With no room to object and with Annie set on leaving now, Jeff gave in and took her out arm-in-arm.

During the drive, Jeff pondered if he could stop at a store to get car clubs, or secret handcuffs, or something else to keep them arm-in-arm and away from grabby lawyers. But since Annie wasn't wearing sleeves – as her arms were one of the delectable bare parts tonight – there'd be no way to hide them. Yet as he dreamed up more stupid ideas to cover up Annie or pluck out everyone's eyes Kill Bill style, he finally realized he had to hide something else – his jealousy.

Before he and Annie got together, Jeff's jealousy was one of the biggest things they argued about. Whenever another man even looked at Annie, Jeff's subsequent comments and actions always seemed to set her off. And now that they were together, Jeff wanted to cut down on things that annoyed Annie all the time. After all, he had three years of annoying her to make up for.

If he even commented on her dress and what it would do to everyone, there was little chance she would take it the right way. She'd probably let out her inner Britta and state he didn't trust her, or thought she was his property, or didn't want her to feel empowered, or some other Britta thing that only made sense with high blood pressure. If he didn't want to turn Annie into Britta – a disturbing prospect on a number of levels –and get into a huge fight, Jeff would have to stay quiet.

After four months of being on his best behavior for Annie, containing jealousy should have been easier for Jeff now. But the theory was shattered in less than a minute – and Jeff still had to endure several more minutes of torture after that.

In that time, he caught virtually every former co-worker, prospective co-worker and man in general checking Annie out. They didn't even give him wiggle room to think it was all in his head, as it was all pretty blatant to him. Unfortunately, they were trained oglers and managed to do it without catching Annie's attention – yet it was much harder to hide it from a pro like Jeff.

By the time Jeff caught a few women eying Annie's curves and cleavage, he wanted to reserve a spot at the open bar for the next four hours. But if he did that, Annie would ask questions, she'd get the truth out of him better than 90 percent of the other lawyers could, and then they'd be fighting all night. And Jeff actually liked not fighting with Annie for the last four months, at least not at an extreme level.

Although he strained to behave himself in certain ways – like not lying as severely and not bragging about his past sex life – it was worth it for Annie. If he slipped up even once, it might open some old pre-relationship wounds and then their honeymoon phase would really be over. Then her old insecurities would return – and so might his old ones that kept him from being with Annie to begin with. So Jeff really had no choice but to clam up, not look at anyone and not encourage the others by ogling Annie himself.

Jeff and Annie talked to guests together for the next half-hour – and by the end of it, Jeff was amazed that all his blood vessels hadn't popped. Some of his old co-workers and guests from other firms weren't as subtle in hiding their lustful gazes at Annie. But through it all, Annie didn't make any comments, or give any hints that she knew what they were doing. Jeff knew Annie could still be naïve sometimes, yet this was pushing it.

He tried to send messages that Annie was his by wrapping an arm around her and rubbing her arms and back. Yet it only made it harder for him to avoid undressing Annie with his eyes. The more he stared, the more he just wanted to escort her out and take her in the nearest empty room. Yet once Annie asked what got into him, he'd probably be too far gone to hide how jealous he was – and how he needed to restake his claim. That would be impossible to come back from, no matter long the fight went on – and one like that could go on for days.

So Jeff headed to the open bar after all, figuring he'd get Annie out of sight and mind until they left. Although this would leave Annie alone and defenseless with the others, he told himself that Annie could handle it and she wasn't a kid anymore. After all, no kid could wear a dress like that, or have a body like that to pull it off – a body that only he had a right to ogle and touch. He went through three years of trying not to touch it, and now that he could, he was supposed to share the splendor with the world?

Jeff then drowned a few shots, in hopes that killing brain cells would make it harder to dream those rants up. When they didn't die as quickly as he wanted, he remembered there were other people besides Annie at this party, so he tried to talk to a few of them. After all, his other goal was to plug himself and plant the seeds for a Jeff Winger bidding war next May.

But plugging himself and planting the seed brought up too many Annie memories, so Jeff tried to use other metaphors in his brain. When he exhausted those, he found some relief in talking to other women and fellow lawyers, despite being rusty at it.

Yet all it took was one boring story for Jeff's eye to wander back to Annie. She was talking to a group of lawyers herself, and when her eye caught Jeff's, she gestured to him and it somehow made her group laugh. She must have been telling them Greendale stories about him, judging by how intense their laughing was. Well, not minding his Greendale shame was one other way to be a better boyfriend, at least.

Still, being embarrassed about Greendale wasn't an easy habit to kick. Not with their insanity, their annoying obliviousness, or their inability to see eyes trailing all over them. Not with how one guy was standing behind Annie just to check out her ass….and how perfectly it stuck out. Not with how a guy in front of her was taking the quickest look at her breasts when she was caught up telling her stories. Not with how those breasts made it oh so hard for guys to take just a quick peek.

Not to mention how those guys were probably dreaming up longer looks then and there. Or their hubris in thinking Annie's imaginary naked boobs could match up to the real thing. Jeff knew they couldn't, not even remotely – and only he got to know that. No matter what dreams they had or scams they might be putting together, only he could know the full glory of Annie's tits without needing his imagination.

They couldn't even make the right eye contact with her when they bothered to. Annie's eyes were too perfect and pure to be met with lustful, dirty gazes. Jeff was the only exception that proved the rule, and that was under special, naughty circumstances only he was qualified for! And he put in a lot of work…..if only at the very end….to meet those qualifications!

Jeff had never worked for anything real in his life, yet he put in three years of toil to be worthy of Annie. These people thought they could just coast in and drown themselves in Annie's eyes, barely contain themselves near her breasts, get dizzy from following her curves, fill their hands up with her round backside, then trail them up and down those soft, velvety legs that wrapped around waists oh so perfectly….

And now they had more hope after Annie actually slapped one of them on the shoulder. Not slapped his face for doing what only Jeff should do. She slapped him playfully – and only Jeff was supposed to receive those slaps.

Now a message needed to be sent.

Before he had the full plan worked out, Jeff stormed over to Annie and put his arm around her. "Excuse me, there's something I need to talk to my girlfriend about," Jeff said with the little diplomacy and subtlety he had left. It didn't completely fool Annie though, as she asked, "Jeff, what was that?" yet he signaled for her to keep it down, since they both didn't want to cause a scene in front of the guests.

Jeff then led them up the stairs, looking for the first office door he could find. It took him three tries to find one that was unlocked, but once he did, he got them inside as soon as possible.

"Okay Jeff, now will you explain this?" Annie asked now that they were all alone. "I was having fun talking to your old friends, and then you….remind them that I'm your girlfriend! Why did you need to remind them, exactly?"

Annie had her hands on her hips while wearing her semi-mad, investigative face – which hardly helped Jeff get any less hot and bothered. But he didn't really want to be, now that they were alone and he could do what everyone at this party was dreaming to do all night – yet only he could do. And he probably needed to start quick before Annie's suspicions killed the mood.

So Jeff wrapped himself around Annie, put her against the wall and then whispered/growled his answer to Annie's question in her ear.

"Because you're mine."

Since that gave away his jealousy, Jeff knew he didn't have long until Annie yelled at him. So he nibbled and kissed all of Annie's hot spots that his mouth could reach, first on her ear and then on the side of her neck. Annie was groaning, but half of her sounds were annoyed ones, as she was clearly still tying to ask what the hell got into Jeff. Yet words were the last things Jeff wanted to use.

The second Annie got a word in, it would trigger a fight in which Jeff couldn't touch her for days – at best. So he wanted to fit in every kiss and maneuver he could beforehand, as he pulled out a few early big guns and devoured the front of her neck. He then got both his hands on Annie's waist and finally caressed every inch of her now infamous dress. By the time he started to dip below that dress, Annie's groans were almost entirely filled with desire.

It appeared Jeff would go all the way one more time before the fight – which made him want to take greater advantage while he could. With that, his lips hotly trailed up her neck and finally reached hers, allowing their tongues to battle each other. After a good minute of battle, Jeff wanted to get his hands, lips and tongue on all parts of Annie that were on display all night.

His hands went back to work all over Annie's little blue dress, while his lips trailed down to her exposed upper chest. While the whole room had gotten a gander at the top half of Annie's boobs, Jeff wanted an even closer view. He didn't even take her dress down to expose all of her chest, as he only planned to kiss, nibble and lather up the exposed half.

Jeff did push Annie's breasts further up, if that was possible, while he buried his face into her cleavage and gobbled it all up. His lips later went down to the clothed half of her breasts, kissing and teasing her nipples although they were covered up. When he gave each a little nibble, Annie groaned and even grunted out her approval as Jeff staked his claim.

But the other guests weren't just drooling over the exposed skin on Annie's top half. They also got quite a view of her silky legs, yet Jeff was going to get much more. He sunk to his knees and began to kiss up Annie's left leg, while his right hand glided up her right leg. He then kissed her upper right leg and rubbed the left, determined to kiss every single inch of Annie's exposed skin.

If Annie still had words to say, they weren't coming out in English, especially by the time Jeff's hands and lips got to the top of her legs. He was severely tempted to kiss what was hidden under her dress – but he only had time to put one big, throbbing part of himself near there.

Jeff got back on his feet and started unbuckling his pants, yet stopped Annie before she could take down her dress. He wanted/needed to finish this off while Annie was wearing this dress, as a final message for the evening. After Annie had tempted him the worst of all with this sexy outfit, he had to see how much sexier it made her look while she was cumming for him – if that could be any sexier.

Once Jeff put his erection on full display, he remembered Annie still had a barrier under her dress. This time he reached down and placed his left hand between her legs, making sure his palm was up against her soaked panties. After rubbing her clothed opening for a few seconds, Jeff got Annie's panties down before she could tell him to hurry up. With that, Annie instinctively wrapped her legs around Jeff as he lifted her up and put her against the wall.

After Annie wrapped her arms around Jeff's neck to steady herself, Jeff was able to keep one hand on her lower back and put the other below her dress. He gathered some of her wetness and then rubbed it over his member, both to lube it up and to mark Annie on him even further. With that task finished, he sunk right into her to punctuate the message.

Jeff knew this wouldn't be their longest time ever – not even close. He wanted to make it last in hopes that Annie would be less mad at him when they got back to normal. But as Annie tightened around him and he got to see her writhing in that dress, he knew he had about a minute tops. Hopefully she was that set to go as well.

If she wasn't, then Jeff made sure she would be, as he performed a series of long, hard thrusts. He pulled out almost all the way a few times only to slam back in completely, causing Annie's screams to echo louder. Remembering that there were still other people in this building, Jeff silenced her with more heated kisses before their grunts got them caught.

As Jeff went faster, Annie moaned directly into his mouth and nearly bit Jeff on his lip. This only inspired him for a final blow, as his hands trailed all over her dress again and stopped on her bouncing, still halfway covered breasts. Once Jeff pushed them up a few more times, he knew this would end any second, so his hands made one more dash for Annie's head. One hand palmed her cheek and the other went directly into her soft hair, helping Jeff pull Annie in for one last kiss and display that she was all his.

The two let out their orgasmic groans into each other's mouths at the same time, with Jeff grasping Annie even tighter as she held onto his neck for dear life. They spent the next several moments feeling the other's release coat their genitals – and not having energy to do much else. But about 90 seconds after they finished cumming, they were able to move a few other muscles again.

Jeff got Annie back on her feet and kept her up until she knew she could stand alone. Yet after he let go, he almost buckled over from exhaust himself. He eventually started to catch his breath, as the fog from his erotic trance was wearing off on cue. And on cue, it was replaced by the rotten memory of how this hot tryst was brought about.

"Well, that should hold me for most of the fight," Jeff muttered before he realized he muttered out loud. "What….was that?" Annie asked, still readjusting her vocal cords.

"It's all right, Annie," Jeff admitted, now wanting to just get the rough aftermath over with. "You know by now why I….did all that. I was jealous of all those men drooling over you who weren't me. I know you really hate that, especially after I used sex to shut you up. But I had to….reestablish you were still mine. Go on and yell at me for being jealous and dishonest, like you usually do. That last little fling should still balance it out for me."

Jeff knew he probably didn't choose his words wisely, yet his brain was still rebooting. Meanwhile, Annie's big brain had likely rebooted and dreamed up a bunch of guilt-inducing lines by now.

Instead, for some reason it was making her laugh.

"Jeff, is that really what you think happened?" Annie chuckled. "You just did exactly what I wanted."

"That's….not enough for me to go on here," Jeff pressed, having little else to say.

"Come on, Jeff, you think I didn't know what….this would do to you when I bought it? Or what it'd do to your friends?" Annie asked while showing off her dress. "I knew you'd get worked up over it, and get worked up about them getting worked up. I just thought you'd wait to….prove I was yours until we got home, that's all!"

Jeff was now getting worked up in a different sense while trying to decipher Annie. But eventually he settled on the theory, "So….you were trying to get me jealous and worked up? How is that….in-character for you? You hated me getting jealous every single time before we got together!"

"Jeff, I didn't get mad at you all those times because you were jealous. I got mad because you wouldn't admit it. And I really got mad because you wouldn't admit why, or let me have any interest in anyone while you strung me along. It was the most aggravating and painful mixed message you ever sent me." Jeff now realized he had left that part out of his past memories….which was a pretty big thing to forget. Yet Annie went on anyway with, "But now that you can admit you're jealous and why, it's easier for me to deal with. Especially now that you can….do something about it other than deny everything in the men's room."

Despite this reminder of the regrettable past, Jeff sensed Annie wasn't scolding him about it. Instead, it seemed that Annie had out-Jeffed Jeff once again and gotten him hot and bothered on purpose. Which meant…."Wait, did you know those guys were checking you out all along?"

"Jeff, come one, even 19-year-old me would have figured it out. She wouldn't have dressed like this either, but that's besides the point," Annie stated.

"Okay then, why did 22-year-old you letthem keep drooling? They could have gotten way too handy before I did anything about it, and you ran that risk on purpose!" Jeff scolded, as his overprotective side was making a comeback.

"Jeff, none of them actually made a pass at me. They just…..window shopped, really. In any case, you forgot a few things while you were getting….bothered. First of all, I can take care of myself, although you still forget that sometimes. Second, you've told me enough…..things about them to help me shut them up if they got grabby. Third, if words didn't work, the techniques from my self-defense classes would have. And even if all that failed, you make a pretty good last resort," Annie reminded.

"Granted, those are some extremely true points," Jeff admitted, suitably flattered by the last reason. "But….but letting them ogle you just to get me extra hard…..isn't new boyfriend me supposed to object to stuff like that?"

"New boyfriend Jeff is still the same as old Jeff in a few ways, so overruled," Annie ruled. "But that's okay. Jeff, you've tried hard to be 'good enough' for me lately, even though you were plenty good before….you just show it more openly now. But we don't need two goody-two-shoes in a relationship, you know." Jeff conceded the point, although he suspected they were closer to zero true goody two shoes these days.

"Anyway, I didn't mind them ogling me that much, because that's all they get to do. I know none of them can really hurt me or steal me from you, and no one ever will. Jeff, I went through Hell and you put yourself through Hell just to get into this relationship. I'm not letting someone who thinks I didn't notice him peeking down my chest ruin all that. And you know I won't let that happen, even though you might forget once in a while. But now that you accept how jealous you can get with me, I can have fun with it on special occasions. At least at the end, anyway," Annie alluded.

Now that Annie's little plan was clearer, Jeff was amazed again at how she had found another new way to surprise him. It was manipulative, a little cruel and made him like a puppet – the student had become the master, indeed. Except Jeff's puppet mastering rarely benefited someone other than himself, unlike Annie's – a typical difference between them.

"Annie….you never fail to surprise me. In the very best way, I mean," was all Jeff could say at the moment. But he then came up with, "You're sure me being jealous and possessive was fun, right?"

"Like I said, it's fun just on certain occasions," Annie repeated. "I know I can't make you flawless, and I don't really need to. I can deal with your flaws in small doses, since you still need them to stay the Jeff Winger I fell in love with. I thought I'd finally make this one sexy instead of frustrating, and I clearly did. I mean, that big performance a few minutes ago was….all Jeff Winger."

Annie chuckled again and Jeff now joined in as she got closer to him. "You know what really almost tripped me up? Me feeling possessive of you too! I mean, I was as affected by your hot outfit as you were with mine….I just tried to be less obvious about it. But when I saw you chat up a few women to distract yourself….I'm glad you broke first or I'd have caused a bigger scene getting you up here than you did!"

"Oh, really?" Jeff asked as his ego got a newfound boost. "So, now you're willing to admit to a jealous side, eh? Well, I can't say it doesn't make sense," he added while showing off his suit and tie.

"I admit you're hot and you're hotter in fancy clothes, that's all," Annie played along. "And that I…..know how hot you are out of them, too. I wanted to….wait and appreciate that back home until we got in here. I mean, I'm still creeped out about doing this while all those creeps are downstairs….but if they haven't heard us so far…."

Annie now glanced downwards, reminding Jeff that during this talk, his pants were still down and his cock remained exposed. But Annie saw that it didn't look as flaccid as it was a few minutes ago. Before Jeff had a retort or a question ready, Annie came up to him and rubbed his chest almost as possessively as he had. And like he had a while earlier, Annie sunk to her knees – but she wasn't planning on kissing his legs.

Jeff was already almost fully erect again by the time Annie gently suckled his cock head. As she slowly took more of him in, she looked up at him and Jeff's knees almost buckled at the sight, like always. As Jeff got harder at seeing Annie's breathtaking eyes gazing up at him during her blowjob, he almost didn't notice her hands unbuttoning his suit. Yet she helped make him notice soon enough as she exposed more of his chest while blowing him.

Her hands got even grabbier as more of his chest was exposed, which in turn made her go down on him more intensely. Now that Jeff had groped and ravished Annie all over like he wanted all night, it seemed it was her turn to do the same. She ogled his chest as Jeff finished removing his suit, then she caressed his upper body all over and never broke her eyes away from Jeff's sight – or let her mouth break away from his cock.

After four months of kissing Jeff whenever she wanted and three months of having sex, Annie's sexual prowess had predictably expanded. This included a perfected method of sucking him off and getting him hard and ready for another round. After taking him all in and then sliding her mouth off his member oh so slowly, Annie drew Jeff's attention to the nearby couch.

Jeff kicked his pants off, helping Annie notice that she was the only one left with clothes. As such, she finally unzipped her little blue dress and uncovered what it was hiding – as if Jeff hadn't memorized it all months ago.

"Even that dress has nothing on what's underneath," Jeff exclaimed, not caring how cheesy he sounded for once – mainly because these cheesy words were at least true. But while Jeff savored seeing Annie's gorgeous, young nude body for the first time tonight, Annie was savoring the sight of Jeff's hot, older nude body as well. Yet she was the first one to do something about it, as she took Jeff's wrist and led him to the couch before she made him sit on his back.

Annie lay on top of Jeff and devoured her neck as much as he devoured hers. Jeff instantly knew he had awakened possessive Annie and he would not be the one in control this time. But as Annie sunk herself back onto him, Jeff knew he wouldn't mind. In fact, Annie was the only woman he didn't mind being overpowered by – she was the only woman he didn't mind doing a lot of things with. And now that he could finally admit it, she was indeed all his.

This had the side effect of re-awakening Jeff's possessive side once again. But with Annie riding him and in complete control, he knew all he could do was match her. So once Annie finished nibbling on his ear, Jeff kissed her deeply as his hands slid down her nude form and deeply rubbed everything they could. They finally stopped on her breasts before Jeff tasted her bare nipples for the first time tonight, stopping just short of leaving a mark.

Annie put a hand on the back of Jeff's head to press him deeper into her chest, while her other hand moved down to her genitals. Although they thrusted against each other quickly and deeply, she still rubbed the bottom of his member and his balls as best she could. In response, Jeff put a hand down there to rub her crotch while thrusting into it.

Jeff finally moved to get Annie onto her back, then thrusted harder into her as their hands got back in place. While each had a hand on each other's groins, Annie put her free hand down Jeff's back until it grabbed his ass. As her hands helped Jeff push in even deeper, he grasped her left tit and rubbed the ample flesh against his sensitive nipple, which made him groan into her neck.

The two traded kissing and nibbling each other's necks and lips for several minutes, as their chests rubbed together and their hands worked in union to help rub each other off. They ravished each other in equal measure, although one wouldn't have imagined Annie keeping up with Jeff in this area months ago. Yet as in other unexpected areas, they balanced each other perfectly.

But with a few final big thrusts and a few "mine"'s into Annie's ear that came out as grunts, Jeff made her explode for the second time. His own explosion came an extremely short time later, leaving them both struggling to catch their breaths all over again. At least this time they were able to lie on a couch.

"Why…do you keep talking me into these things?" Jeff asked after a few full minutes, in a half-kidding tone.

"Because you're mine, silly," Annie somehow said in her usual bright tone before pecking him on the lips with a smile. Only Annie could switch from wild sex kitten back to sweet, loving princess mode in the blink of an eye. Jeff could probably never master that kind of back and forth, and he'd never really wanted to….but life with Annie had proven that things can change.

Nevertheless, now that they could move again, they had to eventually get dressed and get out of this office. There was no point going back to the party, so they decided to just slip out the back, leave and head to Jeff's apartment to relax. Annie didn't mean relax in the sexual fashion – and Jeff found that he didn't either.

There was the real final burn on all those drooling over Annie tonight. Not only could they never get her for sex like Jeff did, they couldn't get her for anything else beyond sex either – and that might be a bigger loss for them.

Jeff reflected on this for a moment before he took his last look at the office. But he stopped thinking about his latest Annie lessons when he finally realized whose office this was. He must have been on a real sexual high not to see it earlier – and he was quite relieved now that he was. Since he figured it out after sex, now he could laugh and wish he could gloat about it later.

"What's so funny?" Annie asked curiously, as if the dirty things she just did never happened.

"Nothing….I just thought about seeing Alan at our next party," Jeff chuckled uncontrollably as he and Annie left Alan's office behind.