Based on a fic prompt over at Milady/Milord by Hypnotoad76. I am not too familiar with dominatrix's, so I hope I made Annie a somewhat convincing one. And this ends up being a future fic, which hopefully helps explain any OOC behavior from Jeff and Annie.
When Annie stood up for prudes everywhere at the STD Fair years ago, it cemented her sexually prudish reputation. Even after her outfits and demeanor got sexier later, her hang-ups about sex still hung over her. But when she and Jeff finally got their act – and each other – together in their last year at Greendale, Annie found that sex was just like any other subject.
And like every other subject Annie ever had, she wanted to learn more.
On some level, Annie knew she didn't have to try that hard. After all, years of sexual tension – and the first several months of releasing it – taught her that anything she did had the potential to turn Jeff on. And yet the same could easily be said and done when it came to Jeff. In spite of Annie's sometimes-accidental power over Jeff, Jeff had even more intentional power over her in and out of the bedroom.
Given his….experience, Annie wasn't that surprised, but it was annoying sometimes. It gave Annie some of the greatest thrills of her life, of course – but she naturally had to over think what that meant. Jeff always had a hold on Annie, which was why she kept clinging to hope when he kept denying they could be together. It had ultimately paid off, yet not before Annie often hated herself for not being able to resist him, in spite of how he could hurt her.
Now that Jeff wasn't holding back anymore, he could make her weak kneed with just one good touch – although Annie learned how to pay him back when she actually got on her knees. Still, no matter how much power Annie, her body and her newfound sexual skills had over Jeff, he always managed to turn the tables at least once. Despite the…..scorching hot results, it upset the part of Annie that liked to be in control, take charge and still resented Jeff for making her weaker sometimes.
There had to be some kind of sexual act to take care of that problem. And since sex was a legitimate research topic for Annie now, she decided to bone up – to use an unfortunate term – and do some studying. But she couldn't go to a library for once, and since she wasn't a Cosmo reader, it would raise some embarrassing questions from Troy, Abed and Jeff if they found her reading that. So she took the safer route and went on the Internet for some answers.
Then she nearly went to scrub her laptop clean – almost literally before she remembered what soap and water did to laptops – when she stumbled onto a page about being a dominatrix.
Since a dominatrix was known for being sadistic, into bondage, treating sex partners like slaves and wearing uncomfortably tight leather, Annie shielded her eyes before leaving the webpage. She was not that kind of girl, even though she now frequently modified what kind of girl she really was. But she certainly wasn't the girl who would mistreat Jeff in the bedroom, or torture him, or force him to do what she said at all times….
Yet the end of that inner monologue gave Annie pause. Wasn't she looking for something where Jeff wouldn't seize control in bed? A dominatrix certainly never lost control….or let the tables get turned unless she said so….no, no it was still too much for even fancy new Annie to consider!
But as always, whenever the chance to learn something new came about, Annie couldn't ignore it. So after a few weeks, she made herself go back to that page and actually learn more about the dominatrix lifestyle. She kept going back to do research every week or so, once curiosity finally got the better of her. And within a few months of this, she stopped feeling grossed out….as much – then began to wonder how she could put her spin on the genre.
Since Annie was also dealing with graduation, making a relationship with Jeff work, and then going out into the work force, she couldn't devote all her time to this study. Yet over the next two years, Annie periodically went back to it and even started to keep a journal. When she didn't keep it in a very tightly locked box with her old Dildopolis gun, she wrote in it to analyze what she learned – and to write ideas on how she could "perform." For a few months, she even fleshed out potential routines and had started saving up money for….equipment.
And then Annie forgot all about it when Jeff proposed to her.
After over a year of using every idea in her perfect wedding book, Annie actually married Jeff. Once the dust settled from the wedding and everyone got sane again, Jeff and Annie recovered to sail through their first six months of marriage. Despite getting more responsibility in their respective jobs, they still found time for each other – and the sex helped when they had some extra free time too.
Once the six-month barrier passed, Annie did some cleaning around in Jeff's apartment – now their apartment – one afternoon while Jeff was out of town. Eventually she found her old locked box, then remembered she had meant to get rid of the gun after she moved in. It took all afternoon to find a safe place to bury it – then when that heart-attack worthy process ended, Annie went back home to put the box away.
It was only then that she saw her dominatrix note book stashed inside, remembering that project for the first time in ages. Looking back, it seemed silly to Annie that she considered doing that…and yet that seed of knowledge was planted again anyway. A week or so later, she went back and actually reread her notes very quietly, which helped her recall why it was a good idea at the time….maybe not just back then, either.
After this last year-and-a-half of wedding insanity, starting married life and progressing in their jobs, Annie wanted to feel in control again. And she still had that same problem of letting Jeff make her weak kneed – especially since he could now lord the wedding madness over her. Yet Jeff did marry her anyway, and was still so grateful that she made him see the light about marriage, and how this one didn't have to be like his parents.
With that, Annie realized that this wasn't just about control – it was about finding new ways to make the man she loved so much happy. The husband she loved so much. Maybe dominatrix stuff wasn't his thing, and maybe he couldn't deal with not having his own way with Annie at some point – which was somewhat flattering.
Yet dominating Jeff was a two-way street. It may be Annie in control, but it was Jeff who would get the maximum pleasure after being endlessly teased. This was the absolutely perfect outcome for Annie, as she would make Jeff happy and feel powerful by doing it – two of her favorite things to do in the world.
But she still needed time to resume her studies and plan out a routine. However….she did have six months until their one-year anniversary….
So Annie resumed her old study plan whenever she had time – although she had far less of it with both a husband and a job. Nevertheless, she found just enough free moments to fill up her notebook again with ideas, while researching wardrobes and equipment. Then she started planning out exactly how her anniversary surprise would go.
When it came time to actually buy equipment, it was probably the most stressful non-wedding/graduation related day of her life. But after fearing that the cops would pull her over, she got back home, put her purchases in a big brown paper bag, burned the old bag to erase DNA evidence, and hid the new bag deep, deep into the closet. She did have nerves left when Jeff got home, but Jeff was so used to her random freakouts that he barely questioned them. This was another reason why Annie was so glad to live with him – she never would have snuck this past Troy's child-like curiosity or Abed's evil wizard powers.
But at last, the big day finally arrived and Annie had her routine fully memorized. She was certain Jeff would take her out for a big anniversary dinner after work, then she would set everything up when they got home. As such, when she came home and found Jeff there, she worried he had already found the bag – even after she found him cooking in the kitchen next to a fancier than usual dinner table.
Yet Jeff soon set those fears aside, explaining that he took a half-day at work to set up an anniversary dinner at home. He insisted he wasn't being cheap, as he had gone all out to get Annie her favorite foods. Plus the cheap argument was moot when he presented his back-up gift; a new heart locket with both Jeff and Annie's names engraved outside, and a picture from their wedding day inside.
After Annie jumped for joy and kissed him, she felt like taking him then and there in the regular old hot way. But then she remembered their dinner would get cold, then happened to remember the dominatrix stuff. Yet she soon felt guilty that she would put Jeff through all this, even after he went all out for this dinner.
That almost made Annie call it off then and there, but she remembered the years of off and on work she put into this. She was getting something out of this after all she made herself learn – and if it went to plan, Jeff would be repaid and then some. If he made himself go all out for romantic stuff he would normally never do, even as Annie's husband, he would find the energy to endure this. And if Annie couldn't convince herself of that, she was no real dominatrix after all – leaving aside how she was only temping at the job tonight.
Therefore, Annie made herself slip into character, even while the romance and Jeff distracted her. She also hoped that eating so much before show time wouldn't affect her or Jeff's performances. But it was one of the many risks she'd have to take – and now it was finally time to make them pay off.
She started innocently enough by saying, "Jeff? I can't believe you put this much thought into our anniversary….and I'm sure part of you still can't either."
"Yeah, that part thinks I'm either trying to send him to the poorhouse or mental hospital. I can lean either way most days, but the mental hospital has better security. So he can go there and not bother us tonight," Jeff informed.
"Good, I'm glad we're all alone then," Annie said – especially since the front door was locked down tight, she made sure the group couldn't show up, and quadruple checked for any bugs or hidden cameras from Abed. "I'm surprised you wanted us to eat here, but it makes sense. We are the only two people who should see this….celebration." With that, Annie took a breath and left the table, announcing, "I'll be right back with part one of your gift."
Annie went to their bedroom, trudged to the back of the closet and got out the least racy part of her collection – at least on the surface. She then headed back to the table and plopped down her notebook in front of Jeff. "A book? Well, I could say I didn't see this coming, but I'm losing my touch at lying."
"Jeff, the book isn't the gift….it's what's inside it." Annie made Jeff focus on her before he started browsing. "Jeff, I love you so much, and I love what you did for me here. My own way of showing how much I love you tonight will….look even weirder by comparison. But I want you to promise to keep an open mind, don't ask questions, and just trust me. No matter what happens or how you react to it, trust me when I say this is all for you….all for my husband."
Despite how cheesy that ending was, Annie still punctuated it by giving Jeff one of her regular sweet kisses. Since it was the last time she would be sweet tonight, she wanted to get the old Annie out of her system for a while. Although Jeff was still likely confused, he started kissing back and giving Annie the usual butterflies – which erased all of her doubt in going forward.
With that, she made herself sound more commanding, albeit not as much as she would be later. "Now I want you to read this book, but I want you to stay in that chair. You can't ask any questions about it, no matter how puzzled you are. Just read in silence after I leave, and don't do anything else until I talk to you again." Annie almost asked "Okay" to top it off, but she stayed in character and instead said "That's an order," in the regular old formidable tone that Jeff loved.
Jeff ultimately nodded, so Annie took her cue to go. She turned at the door and made sure he hadn't started reading while he could still interrogate her. Finally, she went back into their room and made herself completely transform.
Meanwhile, out of the many things Jeff had no idea about when he read the notebook, one of them was why he wasn't chasing Annie right now for an explanation. The note themselves were straight forward, especially in Annie's distinctive adorable handwriting. But even lamenting how he found her handwriting adorable wasn't enough to distract him – especially with such…..dirty details written in that perfect cursive.
After noting how Annie stopped writing after he proposed, Jeff was shocked anew at how it started again. This had to be a joke….if anyone would be this thorough for a joke like this, it would be Annie. However, the very notion of Annie even joking about being a dominatrix was just…..
Jeff learned the hardest way imaginable that Annie wasn't a kid or sexually naïve anyone. Well, that last one he learned in a more delightfully "hard' way. And right on cue, he noticed that Annie's book was….having an effect. Well, anything Annie did had that effect on him, but this….well, then again, why wouldn't it get him hard?
Yet of course, the new good guy, married version of Jeff just had to nitpick it. It wasn't enough that his sweet, mostly wholesome wife gave him a book of kinky notes and was….oh God, what was she doing in there?
"Annie?" Jeff called out, forgetting her orders for a moment. But he remembered them when he heard Annie state, "No talking!" in her ultra-authoritative voice. God, if she was even making that hotter, then would she really…..wait, she wouldn't! But why else would she give him….and why else was it taking so long for her to emerge? Jeff again came close to getting up….yet if he did, what would Annie do to him? Oh God, what could she do to him?
"All right, Jeff," he heard Annie call out from behind the bedroom. "You're going to close your eyes and keep quiet. And you keep your hands to yourself at all times. Is that understood?"
"Not much of this is….but how am I supposed to fix that if I can't talk?" Jeff got out while he could. "Annie, what-"
"No, Jeff, I'm in control here!" Annie yelled, with enough slight wavering to let Jeff know it was still her….and enough authority to keep him sitting and 'standing at attention.' "You'll get all your answers when you keep quiet, close your eyes, keep your hands away and follow my lead….but only if you behave. And you really, really want to obey me." If he didn't then, he did now.
With no choice and a bit less desire to have a choice, Jeff closed his eyes and kept his hands on his lap. Yet at that moment, he briefly thought this was ridiculous, and that Jeff Winger doesn't take orders in bed. He'd give in to Annie everywhere else and succumb to her Disney-eyed boob power in bed, but not because he was ordered to. And what was his sweetheart of a wife doing with this stuff – and who saw her get close to it? Who did he have to put in a coma for the rest of his anniversary?
But all it took was hearing the door open, and hearing the clanking of high heels, to shut his brain off. Jeff focused on just feeling Annie nearby….or whatever Annie was in her place. "Keep your hands right there," he heard Annie order – before he finally felt a blindfold going around his eyes and head. "Okay, now you can open your eyes," he heard Annie taunt.
"Very funny, Ann-" Jeff's counter-taunt was halted when he felt Annie slap his hand – and it felt like it was covered by a glove. If she had rubber gloves on….and if those hands went lower…."Now that you've got the message, get up and come with me."
Jeff felt Annie's gloved hand grab his wrist, which was enough for him to get up and let her lead him away. He couldn't see much through the blindfold, no matter how he tried to use super vision to see Annie. The fact that slap did hurt a little was the only thing keeping Jeff's free hand still, instead of getting a feel of whatever she was wearing – or wasn't.
After they walked a little more, Jeff felt Annie let go of him and then heard her – and those heels – walking away until he heard a door close. Since they were obviously in the bedroom, Jeff felt relieved that this would go somewhere soon. His relief grew further – and so did his cock, if that was still possible – when he felt Annie's lips connect with his. But just as he started to suckle her lips and finally feel what was on her body, he was pushed back and then forced to get on his knees.
"You don't get to move right now, Jeff….unless I say so," Annie commanded.
"Well, why the hell didn't you say that before?" Jeff blurted before he remembered her silence rule. He waited for a response/scolding, but just heard her walking for a few seconds – then heard the much more unsettling crack of a whip.
"I find that you need to make mistakes first before you learn how to behave. You've made your one allotted mistake, so now you can focus on being better. Whether you're brave enough to do it or not." Jeff really wished this wasn't one giant guilt trip on the past, since several years, a wedding and a new locket should have made them even by now.
"Let's try this again. You don't do anything, or move anything, until I command you to. If you still can't get the hang of it, I'll have to be a….more creative teacher. But if you learn to give up being the leader for one night….I may just have mercy on you. Now say just one word to tell me if you understand….well, do you?" Annie demanded.
If Jeff said no, it was bound to hurt in at least two ways. Considering how regular Annie could make him hurt in many more, he might not want to test dominatrix Annie. But even if he said yes, he'd probably get hurt somehow anyway….yet there might be sex involved at some point. Sex with regular Annie was always her big trump card….but sex with dominatrix Annie….well, maybe some dignity could be sacrificed for that. And if it got out of hand, regular Annie and her normal sugary sweet sexiness would probably make it up to him. Either way…."Yes," Jeff ultimately submitted.
"Good. Now get up, put your arms up and keep them there. Do not move them or anything else no matter what." Jeff obeyed her pretty easily there – but obeying while Annie was kissing him again was another matter. He struggled not to hold her or move his lips and tongue, yet Annie took slight mercy and moved her lips down to his neck. She suckled pretty harshly, making Jeff grit his teeth and wonder if he could at least thrust his hips. Something had to make his pants easier to stay in.
But Jeff kept still anyway, even as he felt Annie grab his shirt. She pulled it over his head and raised arms, then felt her lips get closer to the nipple danger zone. Yet her gloved hands played with them instead, before pinching them a bit as Annie gave them a brief kiss.
"All right, not bad so far. Now to put you to work…..get on your hands and knees." It took everything not to tease that she didn't say "Annie says," yet Jeff followed the orders to the letter. "Bend your head down and kiss the bottom of my leg. You'll know where it is when you feel it."
Jeff went back to feeling ridiculous again, yet bent his head down and moved it around. Ultimately, his lips finally felt something soft and….not entirely naked. So at least Jeff knew Annie had fishnet stockings on now. He kissed a few bare parts of her leg before it was pulled away and Annie warned "Keep your head right where it is."
Jeff growled, yet kept his head in place and kissed Annie's leg again whenever she put it in range. After keeping still when she pulled her leg away the next two times, he heard her say, "Good…now you can move a little higher." It seemed she really was training him and rewarding him for good behavior – but as long as Jeff was being rewarded….
He kissed as far up her leg as he could while staying on his hands and knees. But her leg shifted away anyway – yet he soon felt something else press into his face. Something rather unmistakable. "Just lick and kiss the panties….don't try to wander off behind them." Given that Annie's crotch was clearly in Jeff's face, he really didn't want to stop at the panties. So he figured he'd work his magic and get her too worked up to object when his tongue went deeper.
As Jeff kissed and teased the front of Annie's panties, he savored their pure silk and was certain that her wetness was soaking them somewhere. However, he didn't just want to taste her leftovers. As such, he nibbled on the side of her panties before she pulled herself back, which made Jeff groan in frustration – at least that made up 50% of his groaning. When Annie put herself back in range, Jeff nuzzled into her panties again and then navigated his tongue underneath – until he felt one of Annie's hands slap him on the back of the head. The other seemed to be cracking the whip right next to him.
"What did I tell you? I ordered you not to go that far! Now you don't get anything at all!" Annie called out.
"Come on, is that what you really want?" Jeff pressed while he had an opening. "I doubt that sweet, romantic Annie would let dominatrix Annie really whip me or hurt me. She doesn't want this bod to get a scratch, it's just not sexy to her."
"But it's not sexy to you either!" Annie countered. "I can live with you getting banged up for a little while! I have interests other than your body to keep me busy! But you….with all the time you've spent perfecting that body….all the meals you deny yourself and all those ab crunches…..do you really want a big whip scar to ruin that temple? Can you live with knowing that one little part of your body wasn't perfect anymore, and it was all your fault? I can, but…."
Annie kept punctuating her speech by dragging her whip over Jeff's back. In fact, she even took the tip of it and flicked it against his neck. It didn't hurt, but the sensation and the prospect of even a scratch on Jeff's perfect physique freaked him out.
Under normal circumstances, she would just call Annie's bluff and let her chicken herself out – but this wasn't the normal Annie. Finally he gave in and resigned himself to say, "I'm sorry….mistress Annie. I'll be good, just don't punish my abs for my mouth's mistakes."
"Well, I have to punish you anyway…and I think I know how. Now get on your feet and keep your arms up, that's an order!" Jeff sighed and did what Annie said, then waited for Annie's next move. He had a few theories on what it was – yet her tongue trailing over the front of his pants, and the engorged shape beneath it, was barely outside the top five. Nevertheless, it took the upset win and Jeff couldn't even whip it out to take credit.
"It shouldn't have been that hard to do this stuff….I'm doing it just fine," Annie reminded him as she continued licking his covered bulge. "I might have taken this out before, but now we'll never know." She made this even more tragic by actually suckling on the lump as best she could – which was still pretty good to Jeff regardless. Yet he willed himself to keep his arms up and not rub himself against Annie, since he knew that would make her stop.
"It is a shame…..me on my knees, playing with your cock without actually playing with your cock." God, the dirty words were such a low blow…. "You being blindfolded, not able to see down my boobs….and you would have gotten such a good view of them in this thing." How much lower was she going to get? "And of course, there's no point in even looking up at you like I always do….even in this outfit. Shame…."
Of course, she kept licking and nuzzling the front of his pants in between these dirty sentences. With that and the sexy talk, Jeff was almost too worked up to care about getting whipped. "Not….cool…." he groaned out as he felt Annie's lips on top of his bulge. Once they rubbed against it just right, he thrusted against her twice before he knew what he was doing. "Oh God, oh God I'm sorry, please don't stop!" Jeff called before he knew what he was doing.
He growled over Annie stopping and him being a desperate mess – but maybe that last part would make her keep going. Jeff waited to feel her next move, then his breath caught when he felt Annie lower his zipper with her teeth. He couldn't believe begging her actually worked….although she wasn't doing anything right now. In fact, he heard her taking a deep breath or two, like she usually did when he made herself face a test, a big work project or some other fear.
But ultimately, Jeff felt Annie glide her tongue up the front of the underwear showing from his open zipper. She was still licking a surface over his cock, yet since the underwear was directly on top of it, and it had been a minute since she licked him, it felt extra sensitive. After she did it twice more, Jeff thought she might finally set his cock completely free – then he heard and felt her rezip him up with her teeth.
That little tease….and then she went and licked and suckled the bottom of his bulge – i.e. his covered balls. With that extra buildup, the moans on his covered sack and everything else he'd been through, Jeff couldn't hold back any longer. And then history was made.
Jeff Winger actually came inside his pants – which he never even did as a teenager.
He didn't even move, take his cock out of his pants or have any bare part of it touched by Annie. And yet he lost it like an inexperienced virgin anyway. Granted, there were extenuating circumstances and he'd never been worked like this before….and since it was Annie, it was always a handy excuse. Yet…having that little self control was embarrassing, ego deflating and…..probably the entire point.
Damnit. Even in something as unlikely as this, Annie knew just how to make him suffer. Then again, that book did say she spent a few years working this out. And now Jeff was at his mercy….and fully knew Annie could truly humiliate him if he stepped out of line. As great as it was in the moment, he wanted a fuller treatment – and he wanted to actually feel Annie in some way. If he was going to get that before the end….assuming there was more to come….he had to play ball.
"So now can I take my pants off, or do I need to stew in my juices for a while?" Jeff asked while trying to tone down the sarcasm. "Depends, I guess," Annie said with impressive nonchalance, all things considered. "But you did behave yourself this time, so I guess I owe you one. Put your arms down now."
That really wasn't the break Jeff wanted, yet his arms were getting tired. He put them down and waited for more orders – then felt Annie's arms go around his head. In fact, his blindfold was getting looser. Jeff opened his eyes to Annie-like proportions, only to narrow them when he saw the now blinding light again. But once they readjusted out of the darkness, he opened them immediately.
What he saw trumped even his hottest expectations. Naturally, Annie's leather corset was purple, only went down to her crotch and showed as much of her chest as possible. Jeff also saw fishnet stockings and sheer black panties, after having licked these items earlier. Once he noticed the stiletto heels, he finally looked up to see her gloves, the whip in one hand and the blindfold in another, and the dark red lipstick on her lips.
"Fuck me…." was all that Jeff could really say. "You're not quite there yet, but there's still time," Annie countered. She then turned and walked/swung her hips towards the bed, and Jeff instinctively followed her/leered from behind. Once she stood next to the bed, she kicked her heels off and turned towards him again. "Taking a good look at this should help you get hard again. But you'll need to do better when you do….so are we clear?"
"Yes, Mistress," Jeff agreed, not even caring how he sounded – as long as the sights still turned him on. Unfortunately, she put the whip down and held the blindfold up again. Jeff started to groan, but caught himself before he made it worse somehow, then resigned himself and closed his eyes.
Once he was blindfolded again, Jeff tried to keep Mistress Annie's sexy wardrobe in his head, though it made it harder to listen to her. Yet he did hear her command to go back on his knees. After he did, Annie ordered, "You saw my stockings, now I want you to take them off. Using only your teeth."
Jeff almost questioned how he could do that, yet stopped himself again now that he knew better. He went back to picturing Mistress Annie's legs in his head, while leaning his head forward towards then. He nibbled the top of her left leg before reaching the top of the stocking, then tried to bite enough of the top so he could start pulling it down. It took some effort, yet it did seem to start working, although it was hard to stay on his hands and knees as he sunk lower. Jeff was all but on his stomach at the end, yet he got her stocking down low enough for Mistress Annie's satisfaction.
Once she finished getting the stocking off herself, she ordered Jeff to do the same to the right leg. He did so with slightly less difficulty, then laid on his stomach to await the next order. "Now that your teeth are warmed up, you have permission to pull my panties down with them. Don't you dare do anything with your mouth but pull them."
Jeff still couldn't believe Mistress Annie didn't want him to lick her out – or was disguising her need this well. Nevertheless, he resisted the urge to lick her front again, as his teeth grabbed the top of her panties and started to pull them down. Jeff didn't even risk smelling her arousal on the way down, as he just got her panties down and let Mistress Annie step out of them.
"Very good….you've earned another treat," Mistress Annie praised. "You liked licking the front of my panties before….you'd like to lick them while they're inside out, wouldn't you? You want to lick up all the juices you made me soak my panties with?"
"Only if you want me to, Mistress," Jeff restrained himself enough to say. He waited for a few seconds, then felt Mistress Annie's panties brush against his lips. "Then lick before I change my mind," she ordered, and Jeff eagerly obeyed. This time he could really taste her juices, which were delicious despite being soaked into her panties. Jeff never ate them like this before, yet he knew he should taste them in any way while he had the chance.
Yet Mistress Annie then pulled her panties away, which made Jeff groan in disappointment. "If you still want them, turn to the left and crawl." Jeff wasn't even able to object in his mind, as he just turned to the left and crawled on his hands and knees. After a few steps, Mistress Annie's panties were pressed back on his mouth and he resumed nuzzling against them. "Now crawl to the right," Jeff's mistress ordered and he did that for a while before being rewarded. "Turn to the right again," she commanded and Jeff followed, then once she pulled her panties away again, he heard her climb onto the bed.
Jeff was now on his hands and knees on the left side of the bed, while Mistress Annie was lying at the center. "Crawl into the bed with me," she demanded. Jeff reached out for the bed and then climbed onto it once he found it. He felt around for his mistress, yet he heard her get off the bed just in time, before she ordered, "Lay on the bed."
With that, Jeff put his head on the pillow and laid still on his back, as he could almost guess what was coming now. But instead of being tied up, he finally felt Mistress Annie put her hands on his pants and start unbuckling them. Jeff struggled to contain his joy, not trusting that she would grant mercy on him quite yet. And yet she slid down his pants, then took down his own soaked underwear and left him completely naked at last – while finally freeing his erect cock.
"So this is what I kind of licked up earlier," Mistress Annie teased, with Jeff feeling her breath on his cock. He struggled to make himself not thrust up – which got harder when his mistress licked him slowly from his sack to his tip. But he heard her leave afterward, making Jeff wonder how she had that much self control to take just one lick. At least that was better to wonder than how she might make him prematurely cum twice in one night.
After holding that thought, Jeff heard Mistress Annie return, and was barely surprised that she grabbed his right wrist. He wasn't even surprised that his hand was handcuffed to the bed, since it was either that or be tied down. His left hand was handcuffed soon after, but she then moved to tie Jeff's legs to the bedposts instead of handcuffing them – so she was diversifying.
Now that they finally reached the cliché of being tied to the bed, Jeff hoped this meant Mistress Annie was ready to ride him. Although he couldn't hold her or kiss her or devour every inch of her, he'd take just being inside of her again as a consolation. However, she said "I'm going to take this pillow now," and Jeff assumed that she was indeed taking the other pillow on their bed – though he couldn't assume for what purpose.
But it became clear when he felt the pillow being placed over his cock – and then felt Mistress Annie sitting on top of the pillow. Although Jeff's cock and her pussy were now bare, she had put this big barrier in between them – which hurt even more when she rocked her hips back and forth. Although the sensation was pleasurable on her pussy and his cock, it couldn't substitute for being inside her, especially now. And yet Jeff's mistress was torturing them both anyway.
"This is good….it could be better, though," Mistress Annie stated the obvious. "But I don't know….you didn't fill me with confidence that you could last long filling me."
"I can, you already know that!" Jeff insisted. "I'll last as long as you need me to, okay?"
"Can you?" she asked while dragging her pussy across the pillow. "I'd like to go to sleep soon, so we don't have time for you to go three times in one night. This is your last chance….so if I put you in, are you sure you can cum only when I tell you?"
"I…." Jeff trailed off as Mistress Annie rotated her hips. "I'm sure I'll try really really hard…..you know how big that is for me." Yet it wasn't good enough as Jeff felt her climb off him. "Oh come on! Okay, okay, yes, I won't cum too early! I'll cum only when you tell me, I'll last longer and I won't move an inch! I just….I just want you so bad, mistress…." Jeff admitted, long past caring how pathetic he sounded.
"You've always wanted me so bad," Mistress Annie reminded him. "Even though you spent years pretending you didn't. I suppose if you held back that long….you can use those old skills again. But if you can't….you don't get to cum and I get to leave my mark on you," she punctuated by dragging the whip on his abs. "Are we clear, servant?"
"Very….very clear, mistress," Jeff confessed. "Please just fuck me…." He waited patiently for an answer – as if he could do anything else – then almost gasped when the pillow was taken off his cock. "You just make sure I can stay on there for more than a few minutes. That's a direct order."
Jeff tried to seem less eager so he could sell the idea that this would last long. As such, he clenched his teeth and tried not to groan too loud when Mistress Annie sunk his cock into her. Since he didn't come then and there, Jeff saw that as very promising. He didn't even explode when his mistress started bouncing on his cock, so he was cautiously optimistic. He also refrained from thrusting deeper into her, knowing a few quick thrusts could do too much,
She placed her gloved hands on his chest to steady herself, before moving them up to his mouth and face. A few of her fingers briefly dipped into his mouth, then settled for cupping his face as she bounced harder. Ultimately, Mistress Annie laid right on top of Jeff, placing a hand on the back of his head and all but shoving it into her open cleavage. She was also in position to talk right into his ear while she was at it. "You can either suck my tits or fuck me back….you can't do both," she hotly whispered.
This was a tough choice, but Jeff needed to taste some part of Mistress Annie's bare skin – it might as well be one of the best parts. He kissed her exposed boobs as best he could while keeping his hips still, but his mistress still pulled up and dropped the clothed half of her left tit into Jeff's mouth.
Although the leather covered the soft and supple parts, Jeff still managed to kiss and nibble it. She then dropped her clothed right tit into his mouth, and after he played around with it, Mistress Annie placed his head back into her cleavage again.
She thrust his head deeper into her chest as she fucked his cock deeper as well. After Jeff had his fill of fucking her tits with his tongue, he laid his head back down. If he could eat out her breasts without fucking her, he figured he could fuck her as long as he didn't suckle her boobs. For the first minute, the theory appeared to be working.
"Stop now!" Mistress Annie finally cried out after a few deep moans. On command, Jeff somehow made his hips still again, but didn't bother to work on her tits again. He just pressed his face against her neck while trying to hold out, although her sultry noises in his ear and her sultry hips working on his cock didn't help that much.
"I am glad I fit this in," Mistress Annie admitted in Jeff's ear. "'Even after all these years, this still feels spec….er, really, really hot every time." Jeff barely contained a giggle at how she almost slipped character – then remembered he didn't have to stay in any character. "I know….even our first time was better than all the….hundreds of times I had before."
"Jeff!" he briefly heard his regular sweet wife call out. Now that he had some good graces again, he laid back on the pillow and pushed himself deeper in her. "It's true….and I can make this shoot right up the top right now….along with some other stuff."
Jeff thought he had Annie won over and he could bring this to the finish himself – but then he felt something sharp flick his neck. Once he realized it was the tip of the whip, the voice of Mistress Annie returned. "No! I did this on my terms and I'm going to end this on them too! Stop moving now or I use the rest of this thing, temple be damned!"
After all these threats, Jeff was almost tempted to let her use it, just to see if she would. And maybe because a little part of him would like it either way, temple be damned. But his vanity, body image and desire to avoid angry Annie in bed were too strong, so he froze up again. Yet she still stated, "Just for that, I think I'm going to cum a little early now….but you still can't do it."
"And how am I supposed to avoid that?" Jeff inquired, feeling more like his old sarcastic self than a sex slave. Yet Mistress Annie made sure to fix that. "Then I guess I'll finish myself off on the bed while you're still blindfolded. You won't feel or see a thing after all this….but that's your own fault. You could at least feel me cum all over your cock and get it all nice and drenched….but if following orders is still even harder than your cock…."
"No, nothing is harder than that!" Jeff yelled. "We'll see…." Mistress Annie teased as she began rocking on his cock again. "Mmm, I wanna cum on this thing so bad….and I can cum whenever and wherever I want. As long as you follow orders, I still want to make you as wet as me….don't you dare make me not want it anymore, Jeff…." she cooed right into his ear.
"You are a dirty mistress….not just in the good way," Jeff retorted, if only to do anything other than thrust back.
"Oh, you've been making me this way for years. You've corrupted me after all, but that's not a bad thing. I'm still your sweet girl….but I only want to be a bad girl for you, and your body, and your cock that I want to cum on soooo bad…." she groaned deeply as she rotated her hips. "God, I will put this whip down your throat if you make me get off you!"
Jeff no longer doubted that Mistress Annie could do that – and he really wanted her to cum on him too. So he stayed stiff while his cock was getting even stiffer, but it wasn't on the brink quite yet. Once she did cum, all bets were off, of course – and by the way she was riding him, that wouldn't be long from now.
"Oh, almost there….almost there, don't you dare cum," she still managed to order. "You let me do it….let me do it, let me do it, let me…..fuck, I'm doing it! I'm cumming….!" And indeed she was, as Jeff could feel a virtual geyser of cum leaving her pussy and dripping on his cock. He groaned and clenched himself as hard as he could to avoid thrusting, or doing anything that might make him cum too. If he wasn't blindfolded, Mistress Annie might laugh her ass right off of him if she saw his eyes cross like this.
But she stayed on until all her cum was released, which brought Jeff right to the absolute brink. Yet just as he was about to give up, Mistress Annie rolled off him, got herself off his cock and left it standing erect in the wind. The sudden sensation of not being in Annie anymore, coupled with his unbearable blue balls, may have been the worst torture of the night. Hearing her moan and catch her breath moments later was just the icing on the cake – and then she went and scooped up the "icing" left on his cock and on herself.
Seconds later, Jeff felt several wet fingers touch his lips. "Suck them dry," Mistress Annie directed, still commanding despite her intense orgasm. But as long as he still couldn't cum, Jeff was stuck following orders. Yet although he was licking her leftover cum off rubber gloves, her own taste remained good enough to override it. She made him suckle her gloved digits like a pacifier until her juices were gone – and the distraction did stop Jeff's explosion for now.
"Mistress Annie, you're killing me…." Jeff weakly confessed. For some reason, those were magic words – magic enough to make her take off his blindfold, at least. When Jeff could see again, he saw his wife lying next to him, her corset still on and her pussy wet and bare – and his cock still furiously standing up and unattended. And yet while his mistress's body was next to him, the satisfied, beautiful wide smile and eyes were entirely his wife's. "Oh, like that's not going to make me cum…." Jeff felt safe enough to quip.
"You're fine, Jeff, I knew you would be," Annie responded. "But I could just leave you here...tied up and on the brink all night. I could sleep on the couch for a night, make you finish yourself off tomorrow morning and then send you to work. I am that formidable when I want to be….but fortunately for you, I choose not to be."
Jeff sensed an Edison-Winger speech coming on, even after all this. Only Annie…. "Just like I chose to see who you really were all those years ago, not who you kept saying you were. Like I chose to let you be with me after you came to your senses….like I chose to marry you, and like I chose to forgive you when the wedding didn't turn out like my dream book." But Annie slapped his chest – playfully this time – to signal that the last part was sarcasm….somewhat.
"Now here we are. And even after all these years, we're still finding new ways to have fun." Jeff resisted the urge to scoff at how this was all Annie's idea – especially given the results. "For all those times you worried that I couldn't handle you, or how you'd be too much for me, I can still take control over you. I can stay who I am, be in an equal partnership with you….and dominate you when I really need to. And I can choose to take mercy on you too."
"Meaning….?" Jeff carefully asked. To answer, Annie laid back on top of him, but didn't sink onto him again yet. "Meaning I want you to cum deep inside me….even more than you want it. But I'm not doing this because you overwhelmed me….it's because I gave you permission to cum," Annie said in her mistress tone.
"Can my hands help out?" Jeff asked while he was still able to contain himself. "No, I still like you in this position. You're just lucky I love you in all the others."
Jeff nearly said "I love you, too" yet he figured Annie would actually appreciate him saying "Whatever you command, mistress," more. "Good….now follow your last command and cum in me," Annie insisted, proving Jeff right as she hovered herself an inch above her husband's cock. Jeff nodded and waited anxiously for her to sink lower, then she finally sank all the way down.
Annie resumed riding him slowly, with Jeff unsure whether he could fuck her back, or how much he could. However, things were different now that he could see her. Writhing in her skin tight dominatrix suit, utterly in command of him, her eyes and face looking so….sexual despite still having a trace of that old Annie innocence….
But she wasn't the innocent girl he pushed away years ago, nor was she the ruined girl he thought he would create if they got together. She was so much more and better than what he ever expected. And once again, the fact that he was out of his cool comfort zone didn't matter as much, all because of her.
That was obvious if Mistress Annie was overpowering him with her kisses, as per usual. And that was the final trigger to make him fuck her harder than ever before….. "Oh fuck, I'm…." Jeff trailed off a minute later after they stopped kissing and he bubbled up inside.
"Yes, cum now, cum now!" Annie demanded as she got swept away almost as much as Jeff. But not quite as much, given the massive release pouring into her. She held onto his chest to steady herself, letting Jeff overwhelm her for the first and last time tonight.
Jeff finally stopped cumming many seconds later, and stopped groaning five seconds after that. Meanwhile, Annie's adrenaline was wearing off, so she reached down to untie Jeff's legs while she still had energy. But she still had to get up to clean herself off and find the keys to his handcuffs. By the time she did, Jeff looked like he was badly losing the fight to stay awake.
While she still had time, Annie unlocked Jeff's handcuffs, then collapsed on top of him as exhaust overtook her. After all this time in handcuffs, Jeff could barely move his arms, yet he had just enough left to drop them on top of Annie – then they were both out.
Despite all the dirty action, it made complete sense that Jeff and Annie would end the night in this low key way. Once they got their rest, Jeff would finally fully analyze Annie in her costume, take it off, and make up for losing the reigns tonight. And since Annie had her full night of control and dominance under her belt, she could let Jeff take it back for now.
It was the hottest, non wedding night of both their lives – and both later agreed that they wanted to do it like this on every anniversary.
Yet despite how steamy the night was…..when Annie found out that this was the night she and Jeff conceived, she couldn't live it down for the first several weeks of the pregnancy.
Worse yet, they were ran way too ragged for a repeat performance on their next anniversary. But to their credit, they kept a straight face when they convinced Shirley to babysit on the next one.