These are anonymous prompts that were filled over at the community_tv kink meme, with four ultra kinky ones in this section and four more romantic kinks over in chapter 2.
Disney Weekend: Jeff has always had a fantasy about fucking a Disney princess, Annie dresses up for him
Jeff knocked on the Troanniebed apartment door more eagerly than he would have liked. Still, with Troy and Abed gone for the weekend, and with Annie wanting him to stay over and 'keep her company' he had to let some eagerness out. Better than being too 'eager' later on that night, if he got the chance.
Once he got those thoughts out of his head – for now – he noticed no one was answering. Jeff turned the knob and saw it was unlocked, then opened up to see Annie wasn't there. He closed the door behind him and called out "Annie?" wondering if he was too early.
Instead of hearing Annie respond, he heard a lovely voice singing a few high notes. It sounded like Annie's, but with no visual confirmation, he didn't know what was happening. "Annie? Did you invite a guest or something? Because I could have used a heads…."
Before Jeff said the word "up," every part of him stood at attention – every part – when a girl emerged from Annie's room. Her face looked like Annie's, but he'd never seen Annie wearing a pink gown and flowers in her hair – or rather, flowers in a red wig. "Whaaaat?" Jeff asked, ignoring the déjà vu that swept over him.
"Jeff, let me cut to the chase, so we can cut to the good stuff. You remember a few weeks back, when the group played 'I Never'?" Annie tried to remind him.
"I thought we agreed I wouldn't have to, remember?" Jeff vainly tried to argue.
"You drank when Pierce said 'I never dreamed about porking cartoon characters.' And you were drunk enough to admit your cartoon fantasies were about Disney princesses. Just because I made sure the group never talked about it….well, that doesn't mean they forgot it. Well, I didn't anyway," Annie pointed out. "So, here I am. Or rather, here Giselle is."
As if Jeff needed Annie to say she was dressed up as Giselle from 'Enchanted' – at least the pre-Amy Adams animated version. On the one hand, since Giselle was mostly human and never technically became a princess, this might have been cheating – and resembled more of a fantasy about a human Amy Adams. On the other hand….it was Annie in a red wig as a Disney princess.
"I figured we'd get started with a redhead for the opening act," Annie overwhelmed Jeff again.
"Opening what?" Jeff all but coughed out.
"I have Belle, Jasmine, Esmeralda, Rapunzel and Ariel costumes and wigs in the closet. And I have the whole weekend to myself to try them on," Annie teased. "Or off, if it comes to that."
Jeff was beyond mortified to have his Disney princess fetish exposed, even while drunk – especially in front of Annie. Now he wanted to take back every rotten thing he ever said or did to Pierce – at least the things he did after the 'I Never game.' No sense going completely crazy.
"Well, um, if it comes to that, you might need the help of a strapping prince, wouldn't you?" Jeff tried to get in character. But then he remembered, "Oh, fuck, Giselle doesn't end up with the prince! Damn it, now I have to play Patrick Dempsey and block out those Grey's Anatomy marathon nightmares!"
"Well, we can't have that, can we, Disney nerd?" Annie chimed, as she hummed her high notes like Giselle and skipped over to Jeff. "Oh Edward, I'm so happy you found me in this scary human world! We haven't gone to any balls and I haven't bitten any poison apples, so I'm still so happy to be with you!"
"Oh. Um, well, so am I. You wouldn't believe what I've been through with that chipmunk of yours! My hair nearly lost its luster, if that's possible!" Jeff attempted to play along while he still had patience for the good stuff.
"Oh, my dear prince. You know, I learned about the most exhilarating things in this world!" Annie said as happy and perky as ever, even for her. "There are these….things we have that I've never seen in our world before! Let me see if you have one here!" With that, Annie dropped to her knees and almost made Jeff's weaker, as she instantly pulled his zipper down and pulled out his erect human cock.
"Oh my," Annie exclaimed, wide eyed even by Disney and Annie standards. "What a shame we don't seem to have those back home. I guess I'd better use those tricks I read about on that magic box while I can!"
Wasting no time, Annie wrapped her lips halfway down Jeff's cock, gazing up at him and fluttering her eyes in true Disney princess form. That alone was almost enough to finish him right there – but then she started humming. From what Jeff could gather in his haze, Annie was humming Giselle's "True Love's Kiss" song at the beginning of the movie – and humming it while sucking him off.
"Oh fucking hell….oh, I have been dreaming about this," Jeff admitted. Yet a red headed Princess Annie humming a Disney song, suckling his cock and displaying her best Disney eyes could not be matched in any dream. The humming was even pretty clear – maybe Annie had been practicing on bananas or something. And just as those images got in his head, he was ready to get really animated.
"Okay, don't want the lessons to end too soon!" Jeff called before he very reluctantly pulled out of Annie's humming mouth. Despite where it had just been, Jeff bent down and kissed it hard and fast, with Annie getting up and following suit. "Oh God, Princess….you know, I read a few things on this world's magic boxes too," Jeff hinted.
"Show me, my prince," Annie insisted. So in a princely manner, Jeff picked Annie up and carried her over to the bedroom. But unlike Disney princes – at least on screen – Jeff dipped a hand under his princess's skirt. When he laid her down, reached in further and felt nothing underneath, he laid down and put his head into her skirt for a better look.
"Oh my Walt, I've never seen this drawn so well in our world! Looks like it's far from dry, though," Jeff noted. He then performed orally with the same zeal that Annie did, only without humming a song against her. Although he couldn't see the rest of Annie, he could hear her moan and eventually turn those moans into more high notes.
"I've been dreaming about true love's kiss….but never a kiss quite like this!" Annie actually sung – though she made up the second lyric herself. She must have been practicing that too – she really had learned a lot about acting from Troy and Abed. Who really didn't need to be thought of again in this fantasy.
But this fantasy might end too soon if he didn't get to the main event. So he reluctantly licked out Annie just one last time and let his head emerge from her skirt. "Why did you stop?" Annie asked, in a more frustrated fashion instead of a princess one.
Jeff said and did nothing, waiting to see if Annie had something scripted out for this. Finally, Annie just pouted in her most adorable fashion, then tried to look angry although she was doing a poor job of it. "Good heavens, you make me so…sometimes I just want to…..but right now I just want you to, to, to….fuck me!"
Annie giggled hysterically at her dirty words, still doing her best adorable Giselle impression. To that end, she happily cried out. "Yes, that's it! I want you to fuck me! Fuck me so hard that a cartoon flood of cum comes out! Oh, what fun!"
She kept laughing cartoonishly, but she seemed to sense she was a bit too in character right now. So she stopped laughing, gazed down at Jeff's erection that was still hanging out, and pulled him down right on top of her.
"Ooh, I thought princesses were supposed to be more….submissive," Jeff voiced, more as himself at the moment.
"I'm a new kind of princess. In the flesh, as it were," Annie satirized. "So, is my prince going to fuck me royally or not?" Jeff was more than willing to do what his highness commanded, as he pushed himself into her very animated pussy.
After the first several thrusts, the buildup so far and seeing Annie laid out below him in that outfit, Jeff suspected this wouldn't take much longer. But they had all weekend – and apparently a lot more princesses to go. If it would be like this for his fourth favorite Disney princess, what would the others do to him?
Those thoughts nearly ended it then and there, so Jeff tried to just focus on Giselle. But she and her thrusts, her coos, her crumbling face and her red hair were bringing this too close to the end too. However, Jeff was losing the edge to care right now. "Oh, Giselle….oh, princess…." Jeff had to get in.
"Oh Robert….no, wait, Edward, right! You're Edward, not…." Annie slipped back into character, since she did set this scene before Giselle completely fell for Patrick Dempsey. Yet with that in mind, she seemed to be working on and grinding against Jeff even faster.
If the real Annie was thinking of another man during sex, Jeff would have more reason to freak out and question his bedroom powers. But since Annie was playing a character who was fantasizing about someone else besides Jeff's character, it somehow still made it hot. Especially when Annie/Giselle went even faster against Jeff/Edward.
"Oh, fuck me!" Annie sang out. "Oh Robert – dah, Edward! Oh….oh Jeff!" she finally broke character as she tightened and came around Jeff.
"Giseell….Annie!" Jeff gave up and went back to acting as Jeff, calling his real girlfriend's name just as he came inside her. He collapsed onto her as he finished, looking up at Annie's face and how flustered it was, in a definitively non-cartoonish fashion. Yet when she opened her eyes, they still looked Disney like, especially in that Giselle wig.
"So, is that how the fantasies worked in your head?" Annie questioned when they caught their breath.
"I don't know, it's too early to compare them," Jeff played back. "I'm not sure if I need one more round with Giselle to be sure, or if I should start off with Belle."
"Give Belle more time. She's a bookworm, so you know she studied the most….detailed how to books on this subject," Annie made Jeff tingle anew. "Trust me, she has some special stuff planned. But she should wait until dinner so she can get properly dressed up in her….dinner wear."
The thought of Annie in Belle's golden gown – if only for a little while before he got it off somehow – made Jeff even more ready for another round with Giselle. Perhaps he could even stomach the idea of playing McDreamy's part next time – since he did get the kind of happy ending Jeff was enjoying in spades right now.
People Pleaser: Annie likes it when Jeff tells her what to do during sex (very very slight D/s, nothing demeaning, Annie just likes when he takes control)
Annie had become a strong, take charge woman over the years, who would fight for herself and her friends every chance she got. But by nature, she was more of a people pleaser – someone who often towed the line to please her parents, teachers, and the few friends she was lucky to have in high school. And part of her was still scared of losing the true friends she had now – especially with graduation so close – so she did what she could to make them happy and remind them of her value.
But her need to please was used for other extremes elsewhere. Specifically by her boyfriend, Jeff.
With their emotional and sexual relationship firmly established by spring of their final year at Greendale, Jeff and Annie had moved to the more creative aspects of their sex life. And it didn't take long for Jeff to find other….creative ways for Annie to do what she was told.
On this particular night, after they'd had dinner and were watching TV in Jeff's apartment, Jeff broke the quiet, peaceful mood by saying, "Go to bed, Annie."
"What?" Annie asked, having been lulled to distraction by dinner and clips of bad reality shows.
"You heard me. I want you in bed, now. It would make me very happy," Jeff informed, hoping Annie would take it the right way. But she usually did, as Annie got up from the couch and headed over to the bedroom.
Annie knew she wouldn't let Jeff boss her around when they were in Greendale, or around their friends. That made it easier to justify letting him be the boss in bed, at least some of the time. It seemed he wanted tonight to be one of those times, so who was she to deny him? No one, really – at least for the next hour or even more.
"You want to please me? You want to be little miss goody goody, does whatever she's told Annie?" Jeff set up.
"I do. Not everyone likes me, so I want those who do to still want me around," Annie admitted. "Do you want me around, Jeff?"
"Maybe if you lie down and put your hands in your panties," Jeff commanded. Months ago when they were just starting, Annie might have balked and gotten nervous at that order. But now, she knew it was part of the game and that she really did like playing it.
"Like this, Jeff?" Annie asked before lying down and slowly slipping both her hands into her skirt.
"Arch your back when you get to your pussy," Jeff explained further. Annie knew what that would show off, and she only blushed a little as she arched herself and put her breasts on display. "Excellent. Now show me what happens when those fingers go inside you. Show me what I'm in for if I put something else in there."
To give him that idea, Annie slid her panties down so she could put her hands on herself. She dipped a finger into her wet folds, then when it was comfortably inside, she thrust her hips back against it. After fucking herself against that finger, she took it out and put in a finger from her other hand, then made a show of thrusting against it. As she went back and forth with these fingers, she arched her chest out and made her tits sway while making a show of fucking herself for Jeff.
"Do you want to do that against my cock?" Jeff asked a bit horsely, trying not to convey how affected he was. However, Annie knew anyway, and felt more emboldened to follow orders so he'd get even hotter – which made her hotter and vice versa.
"Yes. Tell me what I have to do so you'll do that. Please, Jeff," Annie said with a minimum of begging. Best to save the good stuff for later – though she hoped Jeff didn't agree.
"Good. Start by taking off my shirt. I need to rest my hands for later," Jeff decreed. Annie almost rolled her eyes at his laziness, even in bed. But while he was awake, bed was one of the few places he didn't laze around in. So if this helped him prove it faster….
In any case, as Annie unbuttoned Jeff's shirt and felt what was underneath, she appreciated this job a lot more. But after feeling up his chest and abs, Annie was stopped when Jeff pointed out, "I told you to undress me, not feel me up. You didn't do as you were told. I guess I should go, then."
"No, please! Don't go!" Annie pleaded, half for show and half for real. Inside, she did kind of hate when Jeff made her plead like this, even though they both knew he wasn't going anywhere. Yet her fear of abandonment sometimes made her forget that, even here – and Annie wasn't always fond of when Jeff exploited that.
But then he just had to say stuff like, "Then get naked and show me how much you want me," to get her wet and going. At that point, she couldn't take her shirt, bra and panties off fast enough. Meanwhile, Jeff made a show of huffing and puffing while taking his shirt off by himself. Yet Annie noticed how his breathing stopped when he saw her fully naked.
Knowing she had that power over Jeff – and yet chose not to use it for now – also helped her feel emboldened enough to turn him on further. She did it when Jeff told her to get on her knees and fondle her breasts, then when he told her to finger herself and rub those wet fingers on her nipples.
When she finished, Jeff had his erect cock out and told her to put her hands behind her back. "Go down all the way," Jeff commanded, his slight reluctance balanced out by past knowledge that she could take it.
Although her eyes watered a bit, Annie indeed took all of Jeff's cock in her mouth, even without using her hands. She stayed on him until he had to pull back and breathe again, then when she was all right, Jeff demanded, "Again" and she sunk her mouth back on him. She sucked on him and used her tongue as much as possible, but didn't move her head or lips.
Annie kept popping off him before suckling him all the way down for several moments. Eventually, Jeff took pity and told her, "I think I can let your hands join in. But you have to use them on your tits first." Obediently, Annie put her mouth back on Jeff while her hands played with her breasts and nipples. She made a show of pushing her tits up and squeezing them together, which made Jeff thrust even deeper into Annie's mouth.
Once he pulled out, he noticed her glistening wetness down below and noted, "All this really turns you on, doesn't it? Doing what I say, going all out for me, no matter what I ask….it's as much fun for you as it is for me. I knew you were just a bit too repressed."
"Yes, uptight bossy Annie likes being bossed around, okay?" Annie said, half with her more typical defiance and half out of frustration for not being touched. The mix made Jeff twitch and order Annie back onto the bed.
"All right, you've earned a treat. Touch yourself until you cum. Use me for inspiration, like you always do. Even before we were together," Jeff pointed out, as he lowered his pants and got completely naked, posing and showing off his body to help Annie along.
As much as she often hated to fuel Jeff's dangerous ego, Annie's body betrayed how much his body did 'inspire' her. She eyed his abs and hips and throbbing cock and got intolerably wet, then looked up at his intolerably hot face, lips and hair as she worked on herself.
"I thought you promised you'd fill me up if I behaved," Annie remembered.
"You question my plans again, I might remember my habit of breaking promises. Get me?" Jeff asked in a low tone – just low enough to make Annie's hips thrust harder against her fingers. After that, she was too busy trying to finish herself off to question him anymore. Yet she did notice that Jeff wasn't even touching himself or moving at all.
"Spread your legs wider and tell me when you're gonna cum," Jeff insisted. Not long after Annie spread her legs, and let him see her bury another finger inside her, she felt pretty close indeed.
"Oh God….Jeff, please don't tell me to stop, I'm so close…." Annie all but begged. "Jeff, God, damn it….I'm, I'm right there, oh God!"
But just as she broke through, Jeff took her hands off her pussy – and when she began to cum, Jeff inserted himself right inside her. The double sensation of cumming and having Jeff inside her left Annie both speechless and thoughtless.
She just let herself go and tighten around him, with her moans echoed by Jeff's own cries of pleasure. He didn't cum or even thrust in her, as he only buried himself all the way inside her while she came.
Once Annie was finally finished, she was promptly left empty again as Jeff took himself out of her. She got up to protest, but Jeff drew her attention to how hard and wet his cock was now. "Suck it off. Suck yourself off me now," Jeff nearly pleaded.
Jeff's voice and her own post-orgasm high left Annie unable to refuse. So she went back down on him and tasted her own juices on his cock, eagerly licking it all up. When she was done licking, she sucked him twice more for good measure, just in case.
"Oh, you are a good girl," Jeff praised. "There's still a few more naughty things you need to do, though."
"What now? I mean, yes, whatever you need," Annie corrected herself to be more obedient – for the role play.
"Turn around and bend that pretty ass of yours over," Jeff told her. Annie did what she was told and arched her backside up just for him. With Jeff behind her, she couldn't see what he was doing or admiring – but she did feel his cock being slapped against her still wet pussy.
"You like that?" Jeff actually asked for the first time. "You like being slapped around by my hard cock?" Perhaps he could have used a better term, but the cock slapping was doing too much for Annie to care, as she was getting worked up all over again.
"Yes! You do whatever you want with it! I'll do anything to make it go off, please!" Annie conveyed, burying her face into Jeff's mattress while his tip cruelly rubbed against her pussy.
"Then push back and start fucking it. You're going to have to do all the work, so fuck it real good now," Jeff warned. As always, Annie followed instructions to the letter, pushing her ass back until Jeff's cock was buried into her pussy again. And although he didn't thrust back, Annie fucked herself on his cock hard enough for him to moan anyway.
"Fucking hell, you're too good….this won't last much longer. But keep going anyway," Jeff called out.
"You're not going to fuck me back?" Annie couldn't stop herself from asking. If he was, it seemed like he'd have to do it very soon.
"Do you think you've earned it?" she heard Jeff ask. To start her answer, she squeezed extra tightly around Jeff's cock and wiggled her ass enticingly.
"I hope so," she teased. "I've been a good girl for so long….please fuck me like a bad girl, while you still can. I'll do anything….oh God, anything!" she cried as she felt herself getting close again. "Just fuck me hard already, I'm begging you!"
"Well…." Jeff left hanging, so Annie turned her head and resorted to using the Disney eyes. Of course, she was fucking herself so rapidly on Jeff's cock, it was hard to do both things at once – and her Disney eyes were more flustered than usual. Yet she still wanted them innocent – and submissive – enough to make Jeff finish the job himself.
It must have worked, given that Jeff wrapped his arms around her waist, pulled her up and fucked her at breakneck speed.
"Yes, thank you, fuck me, fuck me, fuck me!" Annie laid on extra thick as she laid back against Jeff's body. After a few more fuck me's and several more thrusts, Annie came onto Jeff's shaft for the second time – and this time, Jeff poured his release into her as well.
The two stood in place as they rode out their orgasms, then kept standing as they caught their breath and relaxed against each other. Finally they gave out and relaxed on the bed, as Annie stayed in a spoon position in front of Jeff.
"Did I do good?" Annie wondered. "Are you glad you kept me around?"
"You….have no idea," Jeff panted. "God, Annie….you do so much for me, you should never have to ask that question. Not for real." Perhaps that was the post sex brain talking, yet Annie still believed Jeff wasn't just talking about what she did in bed for him. He even went on with, "Now, after I stop feeling like jelly….I can return the favor."
Annie was a natural born people pleaser, while Jeff rarely ever wanted to do something for someone else. But it seemed she was so good at it – out of and now behind closed doors – that Jeff was starting to learn from her example. Seeing it in public was one thing that made her so proud of him – but seeing him return the favor in private was mind blowing.
That was more than worth being the submissive one to start off. At least it gave her bossy side time to rest before Annie let her loose on Jeff again.
An Oral Presentation: Jeff gets Annie off just by talking dirty to her (established relationship, not on the phone)
Jeff was woken up in the best possible way. Well, technically, the best way would have been to have his girlfriend Annie wake him up and ride him. But being woken up by Annie's filthy words while she was having a sex dream about them was a close second.
"Oh, fuck me, Jeff…..come on, make me cum…..oh, that cock feels so good," Annie moaned in her sleep. Jeff was beyond stunned and almost convinced this was his own sex dream. He knew Annie was more comfortable with naughty words since they got together, but not like this. How much of Annie's sleep dirty talk had he slept through? Well, he wasn't sleeping through this round.
"Oh, cum inside me, please…..then let me suck all our cum off your cock. Fill my pussy up with that tasty cock," Annie further made Jeff slack jawed – and more than a little hard. After a few more moans, Jeff decided to do something about it. But before he could reach for his cock, Annie woke up from her dream about it.
"Well, don't stop on my account," Jeff somehow recovered enough to joke. Annie gasped, now fully awake after seeing Jeff watch her.
"Jeff! Um, uh, good morning!" Annie tried to act normal. But since she still remembered her dream, it was a little difficult to face him after dreaming that….thoroughly about him.
"Ah, so we're back to PG-13 language, eh?" Jeff teased again.
"Huh? Sorry Jeff, I'm a little groggy. Maybe I didn't get enough sleep," Annie answered all too truthfully.
"No, I suppose not. I mean, since you didn't suck all our cum off of dream me yet," Jeff got to the point. But since she was awake now, Annie blushed and gave her typical scandalized gasp – yet Jeff wasn't fooled. "Oh come on, my image of prim and proper Annie died a long time ago. Now we're just putting her a few more feet under."
"Fine! I dreamed….sexy stuff about you and me! We do it enough in real life, but I've got to have you in dreams too! Happy now?" Annie huffed a bit, embarrassed – and maybe a tiny bit excited – to let Jeff know he had that much power over her.
"Oh, it's a given you'd want me in dream land. I mean, this body was made by dream makers," Jeff bragged. "The dirty mouth, now that's a new twist."
"Oh. Well, um, technically….I think dream you used the most bad words. I was just keeping up," Annie filled in.
"Ah, now I see. My mouth gets too busy tasting you to talk dirty, so you correct my mistakes in your dreams, eh?" Jeff pressed, still more teasing than offended, although Annie feared otherwise.
"No, I love everything your mouth does, really! I love it when it tastes me and it talks to me!" Annie promised. "I guess the dream me likes when it talks a bit more."
"I don't think she's the only one," Jeff zeroed in. "You gave birth to dream you, so she must have gotten her love for dirty talk somewhere. And lo and behold, the girl who couldn't even say penis three years ago is the prime suspect."
"Come on, you knew I could say more in our Dungeons and Dragons game two years ago!" Annie reminded. "Maybe I wanted to break us in before we did the heavier stuff."
"Stuff like what?" Jeff closed in. "Like me fucking you with my big erect cock? We've had a lot of practice with that by now." Annie had no answer, yet the brief fluster on her face was more than enough of one for Jeff. So he continued with, "Or me licking out your hot, delicious young pussy? Oh, we took care of that right from the start, remember?"
"Uh huh," was all Annie had. Jeff saw the outline of her legs clenching from underneath the sheets, so he pulled them back to confirm it. She was probably wet already from the dream, which meant Jeff would have to pace himself to make this last.
"I should have known there was a dirty, naughty girl behind all those cardigans. I knew it already, before we dated or even kissed. But it's nice to know just how right I was," Jeff gloated. "Right about sweet, wholesome Annie wanting to suck and fuck cock like any other girl. Well, since you do it so well, why shouldn't you be proud of it?"
Jeff saw Annie trying in vain to respond with words, but the way she squeezed her legs together was all the response he needed – for now. "Yeah, you are a quick learner, all right. The way your tongue digs into my slit, or the way you wrap your lips and teeth around my big, throbbing little head. And when you gargle my cock down your throat and suck all my cum out of it like a hose….fuck, that's just art."
So was Annie reaching into her bed panties and starting to work herself over.
Jeff knew if he let up, he'd jack himself off from this and never help Annie finish. He just had to keep talking and get her off with his wonderful filthy words, then he'd take care of himself – if he wasn't taken care of by then anyway. "That's why I always give as good as I get, you know that. And eating out every fucking yummy part of you is the best meal of my day. Your lips for breakfast, your tits for lunch, your pussy for dinner, and the entire package for dessert."
"Sometime you need more than one dessert, you know. And in so many different places," Annie chimed in while rubbing herself.
"Don't remind me, I do that enough on my own," Jeff added. "Every time we go to a new room at Greendale, or anywhere else, I imagine the best places to fuck you in," he confessed. "Where I can bend you over and eat you from behind, where you can kneel down and suck me off, where I can fuck you against the wall…..it all blends together after a while."
"Oh, really?" Annie challenged as she dug further into herself.
"Yeah, because it has the same old results no matter what," Jeff set up. "I always end up making you cum so hard all over my face anyway. And then I let you make me cum into your face. Or all over it on special occasions."
Jeff then reached down deep into one of his favorite moments – with Annie and with anyone. "I mean, that time in the shower? I thought your face was even more fucking gorgeous when water made it wet! But seeing my cum next to those beautiful, sexy as fuck Disney eyes, dripping down to those soft, perfect cocksucking lips….don't you know why I stayed in the shower so long by myself that week?"
"Because….because you jacked yourself off to me!" Annie guessed.
"Well, I do that all the time anyway. Those memories made me want to do it twice in one shower. And I usually did," Jeff revealed. "You do those things to me, Annie. You and your hot, tight, wet, perfect body and lips and boobs and everything. You think your sex dreams are filthy? I have a whole sex gutter named after me somewhere! Maybe you'll have one next to mine someday!"
"I hope so," Annie moaned, getting too far gone to control herself more.
"I know so. We're just getting started on the dirty, naughty, hot things we're gonna do together," Jeff promised. "For three years, I dreamed about fucking you….devouring those juicy pink lips, worshipping those big perfect tits, that poor neglected pussy, those long creamy legs and that round, peachy ass of yours. I think it'll take a lot more than three years to act those dreams out. At least, I hope it does."
Jeff was too far gone to notice how serious he sounded, and how much he revealed about his hopes for the future – not just the sexy ones. But Annie was too busy working to the finish to notice, so it balanced out. What's more, now she wanted to keep up like she did in the dream.
"Fuck me, Jeff, please….do it before I cum…..let me cum all over that beautiful cock for real," Annie lost it.
"It's Sunday morning, we've got all day for that," Jeff barely held out enough to say. "You think I won't do all those things to that fucking hot body today? You underestimate the work ethic you gave me."
"Then keep talking so we can fuck early!" Annie demanded. "Tell me….tell me everything, Jeff! I've never had anyone want me the way you do….I've never had anyone want me in any way! That's why this turns me on so much! To have someone want me that bad!"
"Well, that's me! God, all those times I imagined fucking you after the debate and the dance…..and all those complicated maneuvers I wanted to try in the men's room! Or in the storage closet or paintball or the fucking housewarming party or in Glee! And all the ways I wanted to rip that lawyer suit off you and bend you over the bench! Oh, fuck me, Annie!" Jeff snapped.
Although those weren't his dirtiest words, just the memories of his old fantasies made Jeff desperate to finish. Fortunately, Annie was just about done herself, and her calls of, "Yes, fuck, I'm cumming so hard for you, Jeff!" provided the final push for both of them. Annie went off then and there, while Jeff just stroked himself a few more time to her cries before he followed her.
When they finished and made a total mess on both their groins – and parts of their clothes and the sheets – Jeff commented, "I'll say this for dreams. You usually wake up before you have to clean all this cum off."
"Well, let's clean ourselves off and then save your precious sheets," Annie offered. "I could use a shower to finish waking up. Somehow, just doing it myself didn't quite work, even with your words."
"My actions usually mean more when it comes to us, anyway," Jeff admitted. "And I've got ideas for a few new actions now. Maybe a few old ones too?"
"Fine, but don't get it in my eye, you barely missed last time!" Annie warned/teased, as they got back to using their words for banter, playfulness and companionship – all the things that made them work with their clothes on. But their words would be a bit less….playful as the day progressed.
Begging For It: Jeff begs for sexual release
Jeff got into bed with Annie feeling a bit relieved. True, today's study group adventure got him in huge trouble, and got him more than a few lectures about his selfishness – from his friends and his four-month long girlfriend. But as usual, a last minute save and a Winger speech saved the day and bailed him out – plus Annie was still sleeping over instead of going home. So she couldn't be too mad at him anymore.
And when she pulled off the covers and reached into his pajama pants, Jeff truly felt off the hook.
"Ah, perfect reward for a day well saved," Jeff bragged. That might have been too much bragging, given how badly the day started thanks to Jeff. Yet Annie wasn't pulling away. In fact, she stroked him for a few more minutes, although she barely looked at him.
Jeff would insist on eye contact if she was sucking him off, but he could let it go for this. Actually, he would let go regardless in a few more minutes. Or he would have if Annie didn't pull her hand back from him.
Jeff figured she was getting ready for the next step, but she didn't remove any clothing – on her or him. In fact, she went back to her side of the bed and started reading, of all things. "Um, Annie, you kind of skipped a few steps over here," Jeff reminded. "Do you mind?"
"I will. As soon as you beg for it," Annie blandly said.
"Come again? I thought I heard crazy talk, but that's not your style anymore," Jeff commented.
"It's clear in English too. If you want to climax, you have to beg for it. Otherwise I won't do it. And if you try to do it yourself, then no sex of any kind for a week," Annie informed. Now instead of trying not to cum, Jeff was trying not to laugh – and was barely succeeding.
"Annie, I already know you're funny. There's no need for that kind of comedy hail mary!" Jeff chuckled. "Fine, if you're still mad at me for some reason, I'll just finish somewhere else and call it a night."
"No!" Annie commanded. "Jeff, you've got to learn your lesson! And after four months in here, I know sex is the best way to get through to you. Or a lack of sex."
"Annie, I just did what I always do. I do something stupid, you all yell at me, I redeem myself and barely have to apologize, then rinse and repeat next week. Why make a big comedy show of punishing me now?" Jeff inquired.
"Because we're leaving Greendale soon, and that formula won't work in the real world! It might have worked when you were a lawyer last time, but times are different now! You're different now! If you're going to do this crap anyway, you have to learn there are consequences. Like having to beg and embarrass yourself before the next time you get off," Annie informed. "So are you going to learn your lesson early or not?"
"I think I'm going to sleep. I'm sure I can study my lessons in dream world. Good night," Jeff huffed, turning his back to Annie and shutting his eyes.
Unfortunately, his back was still exposed to Annie, who took advantage by rubbing it and kissing his neck. Jeff then rolled on his other side to face Annie, but still closed his eyes and folded his arms. Yet this left his pants perfectly vulnerable as she reached into them again. Jeff thought of rolling back, but a few good tugs by Annie kept him still.
Jeff's next idea was to stay quiet, so Annie wouldn't know when he was on the brink until it was too late. But Annie just had to glide her finger up and down his shaft – and she just had to palm his balls like that too. God, why did he teach her that trick? Because he wanted her to make him cum hard, of course – and she pulled her hand away again before that could happen.
"Annie, come on, this doesn't work as a running gag," Jeff insisted.
"It isn't a gag. Beg me to make you cum or you don't get to. You do it yourself or leave this bed, then no sex for a week," Annie repeated.
"Damn it Annie, you know Jeff Winger doesn't beg in bed! He causes begging, he doesn't do it, and you know that all too well!" Jeff recalled, then got another idea. "And you know it. That's why you won't follow through. You can't survive sex without me for that long, so this is just an empty threat! As empty as my balls will be in a few minutes, so hah!"
"I survived sex without you for three years," Annie reminded. "Even after getting it, I know I can still last without it if I have to. I don't know about you, though." Before Jeff could insist otherwise or demean her plan again, she pulled the front of his pants down and sucked him off – for only seven seconds before she tucked him back in.
"Okay, now this really isn't funny!" Jeff yelled, his newfound frustration building. "Fine, if I can't leave the room, I'll sleep on the floor!" He went to do just that, but the minute he laid down, Annie laid on top of him and grinded down on him as deeply as possible. As angry as he was getting, Jeff just couldn't get Annie off him when she did that.
So he played dirty by grinding back, hoping to get Annie off and make her forget about not getting him off. Yet that failed too, as Annie got up and jumped back on the bed before Jeff could stop her. But with her up on the bed and Jeff still on the floor, he might be able to tug himself a few times – and it might be enough after that grind.
However, Annie came back and caught him right as he put his hand in his pants. "That's a week and a half of no sex if you go further, Jeff!"
"Oh, come on, seriously?!" Jeff growled.
"That's growling, not begging. You're getting warmer, though," Annie all but teased.
"Damn it, fine! I'll just wait until you go to sleep, you can't stop me then!" Jeff gloated.
"Really, Jeff? Me going to sleep before you? Especially when I have all these great books to reread? You must be too worked up to think straight," Annie certainly teased that time. With that, she grabbed her Greendale backpack from the floor and took out one of her books to read – while keeping an eye on Jeff every few seconds.
Jeff groaned and went back to bed, his back turned to Annie again. But after only a minute – not long enough for Jeff's hard on to go away – Annie put down the book and reached over to pinch his ass. This made Jeff get up again, but Annie was too quick and actually pulled down his pants.
In his shock, he couldn't stop Annie from getting his cock and sucking him off again – for longer than seven seconds. As much as Jeff wanted to fight it, that mouth was too strong. So were those eyes when they looked up at him extra wide, and so was that cleavage when Annie pushed it up. That head then bobbed extra hard and fast on him, which almost made Jeff's knees buckle.
Jeff again tried to keep quiet so he wouldn't tip Annie off. But that became impossible when Annie's tongue used that special trick on his tip. Why the fuck did he teach the super student of Greendale things?!
And how the fuck could she pop off his cock and go back to bed without sucking him dry?! Did she forget whose cock this was?! But with the way she brought him to the brink and left him hanging, he almost forgot too.
Jeff grabbed himself out of desperation, but Annie then decreed, "Two weeks, Jeff!" which made him stomp his feet like a child. Annie chuckled at the irony and went back to reading, then noticed Jeff trying to reach the bathroom and corrected, "Three weeks!"
"Come on, can't I pee this out?!" Jeff spat out.
"Not unless you leave the door open. If you don't, it's three and a half weeks," Annie shut him down. Now Jeff was losing it like he was on monkey gas. He stomped around, almost reached for himself again before stopping himself, and kept groaning from the buildup in his balls until he sat back down.
"Annie, you're starting to kill me here! Please – I mean, uh, just finish me off!" he backtracked.
"Well, you started to say please that time. So I suppose…" Annie left hanging until she climbed onto Jeff's lap and inserted him into her.
Jeff threw his head back and groaned in relief, especially when Annie started riding him. He was so blissed out and ready to go, he kept his hands to his side and didn't try to embrace Annie. And by the time he was coherent enough to try, Annie climbed off him and rolled over to Jeff's side of the bed.
"SON OF A BITCH!" Jeff cried out at this latest blow – or lack there of. "Annie, I swear to God I'll, I'll…." But he was too horny and backed up to think of any good threats. None would be good enough to top this torture anyway.
"You know, since you won't beg and take care of things, I guess I should take care of myself," Annie offered, before placing her hand on her wet opening. As she inserted a finger and made it wetter, Jeff groaned some more and reached for her. But he stopped himself and growled again, not knowing what he was allowed to do – and not willing to risk four weeks or another way too short fuck.
Jeff tried to at least ignore Annie touching herself. But he couldn't ignore her moans, even when he covered his ears. He couldn't ignore her when she kept moving around to stay in his sight. And when she pulled her wet finger out of her pussy, trailed it up and down his cock and then sucked her finger dry, it was close to a breaking point.
"God! You dirty, precocious…..gah! I just want to cum already!" Jeff yelled, lying on his stomach and banging his fists against the mattress.
"Well, that's a good start," Annie said while inserting her finger all the way inside her. Out of sheer madness at this point, Jeff resorted to humping the mattress – until Annie announced, "And that's a month, Jeff, congratulations."
Now utterly broken, Jeff practically screamed into the mattress and slumped in defeat. "Okay, okay…." he finally muttered, then lifted his head up. "Annie….please let me cum."
"Not quite, but you're getting there," Annie noted. Jeff didn't even have any energy to nitpick anymore.
"Please, please let me cum. Get me off however you want, I don't care! I'm at your mercy, just let me have my release! Please, please, please," Jeff tried again.
"Closer….in more ways than one," Annie answered while getting herself off deeper. And now that there was a race against time, Jeff finally didn't care how he got it right.
"Okay, I'm begging now! I'm begging you to get me off, happy?!" Jeff spat, but instantly knew he'd have to sound less angry. "I need you to make me cum, I'm begging you….and I'm sorry. Don't make my dick suffer because I'm such a dick, please!"
He saw he was on the right track when Annie's face softened, so he finished with, "I know you feel like you haven't changed me at all when I do this crap! But you have, you fucking have! I would have just left anyone else by now, both tonight and for good! But you're still here, and I want you here, and I want you to get me off….because no one can get me off like you! I don't want anyone else to! Please, I'm begging you to prove it one more time…."
This was by far Jeff's most emotional Winger speech of the day. Something told him it wasn't completely because he needed release. But he just tried to focus on Annie's face and how it reacted, instead of watching her finger. When he couldn't take the waiting, he laid on his back and sunk into sexual misery again.
That is, until he felt Annie climb on top of him and sink onto him again. Yet even that didn't relieve Jeff, since she'd probably just climb off in no time. Yet when she kissed him, squeezed her thighs on him and didn't move when his arms went around her, it hit him that it actually worked.
And when Annie broke and whispered, "You can cum for me now," something else hit Jeff.
Normally, he would still try to hold off until Annie came. But after a few very hard thrusts, enough was enough. Yet midway through the most powerful orgasm in recent memory, Annie released herself and made him go off even harder. They both groaned at the top of their lungs and rode their long overdue relief out together, even after fighting all this time.
By the time it was finally over and Jeff was utterly drained of everything, he found himself admitting, "Maybe I should beg more often." This also let him realize, "I guess it's not a punishment anymore, then. You'll need another way to teach me a lesson in here."
"I'll think of one," Annie muttered, somehow sleepier than Jeff was.
"You would, wouldn't you?" Jeff let wash over him. Annie was diabolical like that – 80s cartoon supervillain diabolical, even. This seemingly sweet young lady was probably the most sadistic, vengeful person he knew when she was crossed. She was torturous, she was an evil genius, she was….a woman after his own cold heart.
Only she made it less cold and more gooey when she wasn't being evil. Like when she just laid on top of him and gave him warm feelings he'd never had in bed before – even after losing this epic game of sexual wits. Even with the loss, he didn't want it to turn out any other way, because then it might not end like this.
It's a wonder why he let himself disappoint her the way he did to start today. Maybe not doing that as much would be a decent way to pay her back. He wouldn't do that for anyone else, but…. "That's why I love you."
He wasn't too sleepy to realize he said that out loud – for the first time. But he was too sleepy to jump up and draw attention it. So he just gave in, went to sleep, and hoped Annie didn't hear him and torture him with that too.
Unfortunately, he was wrong on both counts. But Annie decided to go to sleep with a smile and save the torture for tomorrow.