Wrecking the Homewrecker

Jasmine's punishment ends

Jason's rational mind was completely gone as he lay there cuffed spread eagle on the bed still inhaling Sally's foot scent and tasting it with every breath he took. The butt plug had worked him through more edges than he was able to count and as a result he was just an over aroused sexually frustrated mess in dire need of some relief above all else. What had been hours so far felt like days to Jason as the buzzing plug stimulating his overly sensitise prostate didn't relent in the slightest. It hadn't for all this time and no matter how hard he had squirmed he hadn't been able to dislodge anything. The condom dangling off the tip of his chastity cage was pretty much full from leakage alone.

At the start Jason had tried to resist the vibrations of the plug, he had tried to deny those awful claims Sally made over the speakers as she mocked him in his current predicament, but it was hard. He had struggled denying that he was nothing but a pathetic sissy dork from the start. After all he had just taken a spanking from Sally only to get go through his horribly embarrassing morning routine and to get into a corset only to let Sally put him into this predicament. Despite the fact that it wasn't really a free choice on his part it was hard to deny the fact that it had been pathetic. All the mincing, lisping and giving himself that horrid enema definitely had him feeling even more pathetic and like a complete sissy. He also looked like a dork so arguing that part was hard as well.

He had tried to keep on denying that he was pathetic for the things Sally claimed in her mockery though. He detested the smell of her feet and he really didn't like the vibrating plug despite how physically pleasurable the sensation was as it pressed into his g-spot. Denying it through the constant repetition and laughter was devastating, but as the plug moved him to a first edge it had become even harder to do. A couple of edges in he needed the release bad enough to hope that the sensors in the plug would fail to notice his on coming edge and tip him over that edge he had been on. It was so bad that he really hoped for it making it impossible to deny that he got off on having his sissy pussy as Sally called it in her taunt, toyed with. After all he was hoping to derive even more pleasure from the toy stuffed back there.

The only thing he could still deny was getting off on the scent of Sally's smelly feet, but as his sexual frustration kept on going even that was getting harder. He had sniffed those socks so extensively that the smell had become pretty normal to him. Not only that, but with them not putting even the slightest damper on his arousal, his horny mind couldn't help but wonder whether or not they might be a contributing factor. Especially with Sally's voice saying it over and over again which became harder and harder to ignore the less he could think for himself.

All those worries and attempts to deny things had been gradually pushed to the back of his mind only to vanish completely at the point where all he could think about was a release from his sexual frustration. He had been in this state for what felt like an eternity when sally entered again and it had gotten so bad that the only thing he felt upon seeing her was relief. Relief that he might finally get off, after all there was no way the plug was going to screw up after so many times, that hope had long gone, but Sally might finally change that. Even if she would let him play with that vibrator like he had shamefully done the day before, he would instantly take that opportunity and even beg for it in the state he was now.

Sally felt incredibly pleased seeing the overly horny squirming tied up mess that was her sissified stepbrother. Smiling broadly she finally turned off her voice recording as she closed the door behind her only to walk up to the bed and look down into his frustrated eyes, his lunch dangling between her legs with an even bigger cock shaped teat. His heavily made up freckled face partially hidden underneath her smelly socks. "Hello there Jasmine, I really hope you learned your lesson this time because I won't be pleased if I have to teach you another one. Now whether you can earn yourself a sissygasm this evening or not will depend entirely on your behaviour this afternoon so why don't you stay still for the moment and let me get you out of those cuffs?" Sally offered with a smirk as she shut off the vibrating function on his plug after all this time and started opening the cuffs as well as taking her socks off his face and out of his mouth.

As much as those vibrations had tormented him, Jason still couldn't help but whimper when they came to an end. Right now he didn't want them to end, all he wanted was more, more stimulation so he could finally get off. All he could think off was an orgasm and he wanted it now, not potentially this evening if he had been good enough in Sally's eyes. Having to wait this long in his current state only felt like it was adding to his punishment despite it having been declared over. Then again he knew better than to try and protest it if he wanted an orgasm to finally relief all that built up sexual frustration at all, he knew way better than to try Sally's patience by now and he realised full well that he would need to earn this orgasm no matter the cost, it was the best he could hope to do, his best chance at some release.

"Alright Jasmine, why don't' you get out of bed and tell me exactly what you are?" Sally asked as she crossed her arms with a big smirk anticipating the sheer obedience she hoped her stepbrother would display all for the chance of a sissygasm. It definitely seemed like that would be the case as the first thing he did was correct his glasses with a loud snort right before swinging his legs over the edge of the bed only to make sure to slip his feet into the high heeled slippers, not making that mistake again. She could hardly wait to give him that sissygasm just to see his face when the realisation that he had been motivated by getting his ass fucked dawned on him when he came back to his senses, first she needed to give him something to be embarrassed about though and an afternoon would certainly cut it.

"Hello Miss Sally, I'm just a pathetic sissy dork." Jason spoke as he dipped into a curtesy grabbing onto an imaginary skirt he didn't have in an attempt to act as perfect as he possibly could. He even made an effort to put on his best high pitched voice, the piercing in his tongue causing him to lisp during it. Like Sally had ordered before he kept his eyes glued onto her feet in their worn slippers, the supposed object of his desire which only made his glasses lower even faster, forcing him to correct them that much more. The whole act and every single word of it was devasting, but at this moment Jason didn't care, all he cared about was earning himself that orgasm even if it was still hours away. He just hoped that this was what Sally wanted to hear as her instructions hadn't been extremely clear. He just figured it was as it was what had been repeated time and time again. For as much as it added to his embarrassment, he was glad when Sally started laughing loudly instead of looking displeased.

"Hahaha, that's damn right, you really are a pathetic sissy dork Jasmine. And what is it pathetic sissy dorks like you get off on?" Sally laughed as she eyed up her nervous over aroused stepbrother while he dipped in another curtesy just to repeat Sally's claim about smelly socks and having his sissy pussy toyed with. It only brought on another bout of laughter for Sally who loved his eagerness to humiliate himself just so he could stay in her good graces. This was the exact kind of attitude she wanted from him towards pretty much everyone that was, and not only when he was horny to the point where he would do anything, it was a good start though.

"Good, very good dork. Now why don't you mince on over to your bathroom and put this plug up that sissy pussy of yours, given how you love having it toyed with, I'm sure you'll adore having another toy stuffed up there as well. When you come out I want you to get fully dressed. Make sure to pick out the lingerie matching that corset you picked out, fix your lipstick then come over here and ask me nicely if you may suck your lunch out of my big cock." Sally instructed with a big grin as she grabbed the bottle of specially formulated diet for Sissy's she had ordered from CC's all while she handed him the final biggest plug in his set, one he wouldn't even have dared to think would fit just a day ago. It was going to be the only plug Jasmine would wear from here on out though.

"Yes Miss Sally, right away." Jason spoke as he dipped in yet another curtesy where he raised an imaginary skirt only to come up and snort up his glasses before mincing off with the plug in hand. Even now it felt huge to the point where he thought there was no way it could fit up his bottom, but he knew he had to try, just like he would have to try and take all of that new larger teat, an eight inch one, a silicone cock bigger than his own. It was down right scary, but disappointing Sally now simply wasn't an option, not with an orgasm at stake.

Jason couldn't help but whimper loudly as he pulled the plug that had been tormenting him all morning out of his bottom making it brush over his prostate again. He guessed he would be able to get himself off within a few moments with the help of just one finger. He was so incredibly horny that he didn't even care that it would actually mean fingering his sissy pussy as Sally called it as long as he would get rid of this mind wrecking horniness. The only thing stopping him was the fear of what Sally would do if she caught him which she was sure to do if he suddenly looked a lot less horny. No matter how he thought about it, he knew it could only end in more punishment. He had no doubt that Sally could just tie him up again to subject him to an afternoon of edging as well, if she wouldn't make things even worse that was. No anything but earning his orgasm would just end in disaster he thought as he lubed the new plug up and forced it up his bottom with a moan as it got seated against his prostate.

He couldn't help but need a brief moment to recover once it slipped past it's widest point which brought him a ton of discomfort, but much to his shock no real pain or resistance to the huge size of that thing. As scary big as it had been, it had slipped in with way more ease than he had ever imagined which told him a lot about the state of his bottom. It was shocking, but he had no time to waste as he quickly minced out to his closet to put on the matching lingerie to his corset, another small variation on his sissy school girl uniform.

They all looked so much a like yet slightly different. The panties mainly made out of white satin with pink lace surrounding the hole for his cage and bottom, the stockings were sheer pink with white tops and a back seam as he couldn't help but struggle a little with the garters and getting the seams straight which remained a real pain. The ankle socks were made out of pink nylon with a white lace trim an bow, and the very high heeled Mary Jane styled shoes were made out of white patent leather. This time his skirt was mainly white with a pink tartan pattern, and his silk blouse was a solid pink yet thin enough to be mildly see through. The bow tie he wore matched the pattern of his skirt and his fingerless gloves were made out of pink lace with a white bow to tie it off at the wrists.

Fully dressed Jason minced to his vanity table and sat down delicately the way he had been taught to do. His lipstick was awfully smeared from being stuck under Sally's socks all morning so it definitely needed fixing. It was hard to do with how horny he was, but he managed to paint his lips perfectly having had plenty of practice at that over his short time here. It was a motion by now so ingrained that it almost went automatically. He quickly smoothed his it out by smacking his swollen lips together. Done with his lips he brushed out his ginger hair and put it in two neat ponytails tied off with a white satin ribbon.

Now that he had completely readied himself to Sally's expectations, he got up and minced right over to his smirking stepsister. "Miss Sally, may I please suck my delicious lunch out of your big cock?" He asked in his high pitched voice while dipping in a perfectly executed curtesy, the short skirt rising enough to expose his chastity cage poking through the hole at the front of his panties. He didn't really feel like sucking that huge cock shaped teat again, but he was desperate not to screw up and lose his opportunity for an orgasm, or worse risk another punishment as he pretty much accepted by now that Sally was way stronger than him.

"Yes you may Jasmine, what excellent behaviour of yours. I'm very pleased. That punishment definitely did you very good. Now before you get down on your knees why don't you lift your skirt for me again, don't drop it until you have permission sissy!" Sally spoke with a huge grin as she watched her stepbrother comply in an instant, lifting his skirt daintily as if for a curtesy only to keep it high rather than dropping it down again leaving his cage in full view.

Without delay Sally reached under his skirt only to grab onto his caged cock and finally slip off that pink condom filled with all the precum that had leaked out during his very long drawn out edging session. Smirking broadly she held it up so he could get a better look at it and just how incredibly full it was. "Oh my Jasmine, you really are an even more pathetic sissy dork than I realise, just look at how much you loved getting your sissy pussy toyed with. Most guys wouldn't even be able to produce that much cum in a big pent up load, yet you leaked it all out of that clitty of yours without ever getting off you sopping wet slut." Sally taunted, loving how red his face turned as she laid it on thick.

Very pleased with the intense shame making it through the abject horniness on the sissy's face Sally finally decided to go ahead with his lunch. "Alright Jasmine, you may lower your skirt and get on your knees. Let's just add a little more flavour to your lunch shall we my pathetic sissy dork?" Sally grinned as she waited for him to kneel only to move the cock shaped teat right up to his face before slowly emptying the filled condom over it, glazing it with all that had leaked out of his cage. It was enough to spread a glistening coat over the entire length of the eight inch silicone shaft as she gave him the go ahead to start sucking before it would drip off.

Jason was mortified just looking at the large cock coated in pre cum even if it was his own. Yet he knew he didn't have a choice, he needed that orgasm and so he grabbed the bottle of fluid to support it before wrapping his plump lips around the way too realistic looking cock. It was something he had done way too often for his liking, but it had never been more devasting than now. The taste of precum was like that of a watered down version of the load he had had to swallow the day before, but it was plenty of bad, then again, it wasn't worse than the nasty taste of Sally's worn socks which it replaced though, still the implication of sucking cum off a rather life like cock was so much worse.

Opposed to other times where he sucked his lunch out of these rather sophisticated cock shaped teats Jason didn't bother to prime the ring just behind the head five times. Instead he went in for the deepthroat right after priming it once in order to slobber all the precum off the shaft straight away so he could drown out the taste with that of his specialised formula rather quickly. Swallowing all eight inches of this even larger silicone cock proved to be a real challenge though. Once again he really had to force himself beyond his gag reflex to get it all down, but luckily with all the training he had already had with previous sizes that had challenged his gag reflex he could manage it after trying hard. Sealing his lips around the shaft while sucking his way back up gathered all that pre cum which he was forced to swallow only to drown out the taste with that of his formula.

With the cock now pretty much just saliva coated Jason went on to suck it like he had so many times before, spending ample time massaging the head to prime it only to go down it's length a few times and repeat. He had no trouble at all with moving that ring behind the head anymore, his tongue had grown skilful enough to manipulate it with ease. He never failed to make it full circle anymore making the whole ordeal that much faster, but not any less shameful as he realised it just meant he was becoming a perfect cock sucker.

Over the course of about ten minutes Jason managed to dutifully suck all of his sissy formula out of that horrible silicone cock. The trouble deepthroating the large shaft had pretty much disappeared by that point making him blush over the thought of being able to easily take cocks bigger than his own that while his past girlfriends had had trouble with his without gagging. He was a better cock sucker than any of his past girlfriends and it stung like hell.

Sally for her part was very pleased while Jason wouldn't be able to suck the biggest cocks out there yet, he was well trained enough by now to be able to handle over ninety percent of all cocks which was getting pretty close to being able to suck every cock with ease. The smeared lipstick and the pink ring at the base of this cock shaped teat were just precious to her. "Alright Jasmine, time to get up and mince on over to your vanity table. I think it's time you learned full makeup rather than just lipstick." Sally grinned as she pulled out of her stepbrother's mouth.

When he finally made it back to the vanity table with a perfect mince and delicately took a seat, Sally was right there with some of the specialised wipes to clean off the makeup Suzan had used at the salon. It was one thing Jason was all too eager to do. Finally he would have a completely clean face again, finally he would see a part of himself again he imagined as he quickly started wiping his face clean only to be horrified when he rubbed on the freckles time and time again only for them to stay right where they were. Even with a completely clean face he still looked like a sissy dork. The thinned ginger brows, the extended lashes, the many freckles and plump lips made his face look terribly feminine making it almost impossible to pass as a guy much to his horror.

Standing back Sally loved the look of horror on his face when he realised it wasn't just the makeup making him look like a sissy. She didn't even give him a chance to recover as she just placed a laptop on the table next to him before taking out his whole makeup kit and stalling it out as well. "Alright Jasmine, here is a video to teach you to replicate a perfect makeup look like you had just moments ago safe for the ravaged lipstick. Be a good dork and follow every step as closely as you possibly can. I don't expect perfection, but I expect progression every time you reapply it. Now I'll got for just a brief moment, but I expect to see you busy with nothing but your makeup upon my return." Sally instructed with a grin before turning around and leaving the room while Jason nervously turned to the laptop screen.

Jason couldn't help but sit there mortified as he watched a pretty petite red head with a bad lisp give him a rundown of the various makeup products displayed before him. A rather complete set including blusher not that he needed it at this point Jason thought. The only thing that was lacking was any kind of foundation. After all Sally didn't want him to cover up his freckles under any circumstances. Sighing deeply he got started together with the redhead on the screen to apply his makeup once she had given the rundown.