Wrecking the Homewrecker Pt. 38

Bedtime for Jasmine

By the time Jason had worked his way through all the papers Sally had put in front of him, he was a wreck. His legs and feet were aching real bad from being on these horribly tall heels all day, that and having to adopt this horrible ridiculous mince. His throat hurt a little from forcing himself to talk in this ridiculous voice, that and trying to swallow the whole eight inch length of that horrible dildo he had constantly called Daddy throughout this horrible routine Sally had put him through. Whatever pride he might have started his day with had been entirely crushed, something he would have minded a whole lot more if he wasn't so incredibly aroused.

He could hardly think clearly anymore, his caged cock constantly struggling to get hard, leaking profusely as his balls hurt something fierce. It was a very bad case of blue balls like he had only once had on a camping trip with friends without the opportunity to get himself off for a week. This felt so much more intense though, and it had only been a little over a day since his last orgasm, having jerked off just before leaving to catch his flight the day before. Then again, his plug that by now no longer felt way too large had pushed him to more edges today than he had had orgasms this past month. Despite his horribly shameful circumstances he was dying for an orgasm more than ever before as he stood before the empty basket nor really knowing what to do now.

Sally for her part was extremely pleased with the way things had gone down today. Jason had only been under her control for one full day and he had already radically improved, at least toward her goal of making him the biggest most pathetic sissy in existence. His voice for as ridiculous as it was sounded a lot more natural already to the point where people would notice the ridiculousness of it before they would notice it was fake. His mincing, curtseying, gesturing and sitting in the meantime had grown a lot more natural looking as well, there was a little more perfecting to do, but those slight details that needed to get worked out were hardly noticeable by now. His handwriting, much like the rest of the changes had grown more fluid and natural as well, and she could see how horny he was, ready for the next step in doubling down on his shame. Oh she so loved seeing him constantly embarrassed and with the routine she had put him through that had worked wonderfully. It was getting late now, but her once jock of a stepbrother was acting more or less as dainty, pathetic and submissive as he looked.

Getting the last details worked out and more importantly, getting everything to become pretty much second nature to him to the point where he would have trouble walking without an exaggerated mince, or even just meeting people's eyes would take a lot more time. Just like changing his body would take time. Despite the muscle relaxant making him weak, and his outfit more or less hiding his muscles, his body wasn't looking as delicate as his outfits yet. There was a lot of slimming down to do when it came to his muscle mass and his waist, but with his sissy formula that would happen in due time as well and luckily time was something Sally had plenty of.

"Alright Jasmine, it's dinner time. Now go and be a good sissy and pick out your bedtime outfit while I go fetch your dinner." Sally grinned, loving how her sissy stepbrother dipped into a proper fluent curtesy and gave her a proper "Yes Miss Sally" in her improved sissy lisping voice without even needing to be told. This was perfect. As Sally spun around to head to the door, Jason minced his way over to his closet filled with offensively feminine outfits. They were all so bad that it hardly mattered what choice he made making it surprisingly easier to pick something out. All he had to take in account was that it needed to be a matching outfit as he picked out the first nightie he saw and put it over his arm while searching for the matching lingerie and shoes to go with it.

By the time Sally returned to the room she found her sissy stepbrother sitting on the edge of the bed, legs perfectly kept together and his gloved hands neatly folded in his lap, only shooting up every once in a while to fix his glasses back up with a loud snort. It was perfect, as was the worry and shame on his face as he eyed the big pink bottle of formula and the by now six inch teat, the teats rapidly growing bigger as Sally wanted to make sure that Jasmine would be able to deep throat any cock she was faced with. One look at the very pink bunch of clothes laid out next to Jason only made Sally smirk even wider. Obviously the sissy knew that there was no choice other than perfect obedience. "What a good sissy you are Jasmine, so neatly waiting for me, I guess I won't need to spank that tush of yours then. Now be a good sissy, come over here and ask nicely for your delicious sissy dinner from your favourite shaped object." Sally spoke with glee, chuckling as the sissy got up quickly and minced right over to her.

Jason was mortified seeing Sally with that by now rather large cock shaped teat, one he would have to take down entirely to eat. The mention of the spanking however brought the fear right into his horny mind, he just had to suck it up, literally. He was no match for Sally maybe tonight when she left him alone he would be able to escape he thought as he whimpered slightly raising back off the bed. So far for sitting down to let his very sore feet catch a break. Dipping in a deep curtesy and once again fixing those horrible glasses that just kept on sliding off Jason spoke up in that horrible lisping voice. "Miss Sally, may I please have my delicious sissy lunch from that delicious looking cock shaped teat?" He lisped in his high pitched sing song voice, the shame burning bright even through the horniness.

"Of course you may Jasmine, after all I brought it up just for you, so please by all means go ahead, knock yourself out. There is no way I can deny such a pathetic dork who asks so nicely." Sally grinned adding insult to injury yet despite that getting a curtesy and a thank you from her sissy stepbrother who was hilariously obedient. She just loved it, especially when Jason then got down on his knees, not wasting any time as he grabbed the bottle with his daintily manicured and gloved hands to support the weight only to wrap his perfectly painted plump cock sucking lips around the head of the teat, instantly circling his tongue around it to wind up the mechanism. It was clear that Jason was getting very well practiced at this as he quickly wound up the mechanism the maximum of five times without letting it slide.

Sally just loved it, she loved how quickly Jason had knelt before her and how he was starting to suck 'her cock' like a pro. This harness mount for the bottle gave her such a fantastic point of view. Looking down there was barely any identifiable trace of the straight jock he had been just yesterday left, the ginger hair, the glasses, the heavy makeup, the freckled face and the seemingly skilled eagerness with which Jason was sucking was just amazing. She knew full well that this was the last thing Jason wanted to be doing, but he had clearly yielded to her control not that she hadn't given him enough reasons to do so.

Jason's perspective in the meantime was nothing more than embarrassing as he couldn't believe the ease he was starting to have with handling that cock shaped teat, or at least the head of it. Nevertheless despite the shame he gave it his all, wanting to get this over with as soon as humanely possible and preferably before Sally would get it in her head to start face fucking him cause that would make things a whole lot more difficult and he knew that his stepsister was anything but patient, hell she was unreasonably impatient, but there was nothing he could do about that but deal with it as he didn't realise his fresh bottle of formulate was the big reason why he was so weak compared to her, if he did, he would have tried fighting it off more, hoping his strength would return and he could get to her before she could zap his cock. Not knowing just made him assume that Sally had just grown much stronger since he had last seen her.

While Jason managed to handle the head of that horrible silicon teat just fine, taking the length proved to be a whole lot more difficult for him though. In order to take the six inches of the silicone cock, he had to allow it to push through to the back of his throat just past his gag reflex making him gag violently with his lips sealed around the grith. It took a little effort, but it wasn't that long that he had real trouble pressing that release button at the base allowing him to suck back to the tip rather quickly, gobbling up a mouth full of his sissy formula before sucking back down and repeating the process. The loud laugh from above and the shaking of the silicone cock in his mouth that followed as a consequence of Sally laughing over his loud gagging didn't help at all.

At least this time Sally did fully let him do his thing without taking control and fucking his face. Over time the length got easier to deal with as well as near the end of the bottle he was able to take the silicone cock without gagging. It was nothing to be proud of at all, at least not for him, but it did make things a little easier as he finally pulled off of the teat, having finished the bottle. His lipstick was sure to be ruined and he knew Sally required him to keep it in top shape at all time, only he didn't know what to do now. He doubted Sally would appreciate it if he just rushed off to his vanity table to fix it, but then again he might get in trouble if he didn't do it and the last thing he wanted right now was more trouble than he was already in. This was all terrible enough without another spanking.

In the end he decided that maybe it was best to just ask. Getting up from his knees he dipped into another deep curtesy, quickly fixing his glassed near the end before speaking up in his badly lisping sing song voice. "Thank you for my sissy dinner Miss Sally, may I please be excused to go and take care of my makeup?" He asked hating how he had to grovel for something so horrible, but it was the least confrontational thing he could think of doing and avoiding confrontation with Sally was a top priority.

Nevertheless he couldn't help but cringe as Sally was very quick to laugh with him straight away, he felt about as dorky as he looked, standing there squirming while looking down at Sally's feet, waiting for permission for something he didn't want to do in the first place as Sally seemed to be in no rush at all, happy to just let all her laughter out for a good full minute. "I'm sorry Jasmine, but that is just so fucking precious. Of course you may go and fix your lipstick, after all if another cock for you to suck were to appear those lips of yours must look as inviting as they did before you started sucking mine." Sally laughed, laughing even harder when Jason dipped into another curtesy and thanked her before mincing over to his vanity table and getting to work on repairing his smeared makeup. Little did he know she hadn't been planning on making him do that again before bed, but since he offered, there was no way she was going to say no. She just loved how terrified he was of her.

Well practiced as her sissy brother was by now Sally watched on in glee, his mince, the way he sat down, it all looked so ridiculously pathetic, she loved it. She could see the shame over her look and her by now very smeared lips reflected right back at her by the mirror. It was delicious, as was the fact that despite that shame he quickly got to work on fixing his makeup. With a bit of makeup remover he quickly cleaned his plump lips up, then carefully outlined them with some lip liner before applying a heavy coat of lipstick and eventually some gloss to finish things up into a pair of perfect cock sucking lips that seemed unspoiled. Without even being told to Jason then stepped over to his full length mirror, fixed his hair a little, straightened his stockings and brushed down his skirt, making sure his look was picture perfect again, like he had done all afternoon. He just assumed it was his safest bet despite the huge shame it brought him. It wasn't like he hadn't done this all afternoon, but doing it on his own initiative just made it that much more painful.

"I'm very pleased to see that you have taken all my lessons to heart Jasmine. In fact, I'm so proud of you that I think you deserve a real good reward, you see, I can be a benevolent teacher for a good sissy dork, but first why don't you get ready for bed? Go and grab that outfit you laid out for yourself, then mince along into the bathroom. Your bed time routine is pretty much the same as your morning routine plus hand laundering the outfit you wore during the day, then again your morning routine will feature hand laundering your night time outfit from now on so remember that well Jasmine one more thing you will do every night is remove all your makeup and apply a hydrating facial cream to keep that skin of yours silky soft. I'll give you the special remover to get rid of all your makeup this time so you can practice full looks tomorrow. I'll supervise just to see you are doing everything right this time, but starting tomorrow I'll expect you to do everything on your own the moment your alarm wakes you at 6 a.m. So you can be ready for me by 8 a.m. Fully dressed, fully cleaned, your bed made up and the clothes you've worn today neatly put back in your dresser. For tomorrow just doing your lips will suffice for the morning, but once you learn to do your full makeup, that will be another requirement, after all a sissy shouldn't be seen without a full face of perfect makeup, unless by someone who has just ruined said makeup." Sally rambled off instructions as Jason just looked at her in utter horror, it felt like his head was going to explode from all the information as he had had to fix his glasses two times during her speech, it was really becoming a force of habit by now.

"Yes Miss Sally, I understand." He eventually meekly spoke as he dropped into another deep curtesy, then minced over to his bed to fetch the nightie, lingerie and high heeled mules. He couldn't believe he had just fixed his makeup and outfit for nothing as he was supposed to undo it all now. It wasn't that he wasn't happy to get rid of his current makeup and outfit, it just stung that he had put himself through such humiliation without there being any need at all, then again it wasn't a relief either as what he was going to wear now was hardly an improvement on his current outfit. As much as he despised these elaborate morning and night time routines, Jason was actually looking forward to soaking in the tub for a good long while. With how sore his body was laying down in the warm water, despite its fragrance was bound to feel great.

There was a lot more to be done than soaking in the tub though as he quickly put his night time outfit aside and started by running his bath, adding in beads, oil and some foam to make it smell like a damn flower shop only to then interrupt the flow of water by filling up his dreaded enema bag. Hanging that up on the hook Jason minced over to the sink where he cleaned off his full face of makeup with the specialised remover Sally had handed him. It should have been a relief to see his face again, but it was anything but a relief. Even without makeup he looked like a huge sissy dork. His plump lips were no longer as vibrant, but their pillowy shape definitely seemed inviting. Her thin arched ginger brows feminised her upper face a great deal, especially combined with the eyelash extensions that stayed on, making it look like he was wearing a ton of mascara. Most worrying of all maybe was the vast amount of freckles that stayed on his face no matter how much makeup remover he rubbed over it. It made him fear that they had tattooed them on or something. They were only semi permanent for now, but there was no way for him to know that. All it did was make him realise that if he finally managed to escape, just a change of clothes and a haircut wouldn't cut it to make him look like himself again. He was so screwed.

Urged by a cough from Sally to make him move on from staring he finally started to strip under Sally's gleeful supervision. It was horrible to get naked in front of his stepsister, but after everything she had put him through so far it wasn't the worst. In the end all he was left with was his long ginger hair, his embarrassing pink cock cage, his long pained nails, his plug and deep red lines from where his corset had dug into his waist all day. With an embarrassed whimper he moved out in front of the enema bag, pulled out his butt plug and grabbed the nozzle. It was mortifying to stick something up his own ass, yet with how horny he was from the constant buzzing against his prostate all day, sending him to edge after edge there was also an urge to just use the nozzle to get him over the edge to finally give him that orgasm he craved so much, the orgasm that would hopefully relief the pressure in his balls.

"Don't you dare fuck yourself to an orgasm with that nozzle like the cock hungry sissy you are, just let the water flow and rinse out that sissy pussy of yours. Here, this is your new plug to put in once you've emptied yourself. Open up so you can lubricate it a little." Sally grinned as she offered the new, even bigger plug, the middle one of the five decorating Jasmine's nightstand up to the sissy's lips with a big grin. She could see the terror and shame in Jason's eyes as he slowly obliged, and opened his lips to accept the plug that felt way too large to ever fit into his ass, he doubted he would get use lube so getting it soaked with saliva was absolutely crucial.

Jason was mortified kneeling there on the floor with a plug in one end, and the nozzle in the other as he quickly let the water flow just to get this over with. As horny as he was he wasn't horny enough to actually fuck himself to an orgasm. It was just too embarrassing, but the fact that Sally had seen through him, known what he was thinking if only for a brief moment was down right devastating. Could he even deny being the cock hungry sissy Sally claimed he was when the thought of fucking himself with the long rigid thing had actually crossed his mind? It was another huge blow to his beaten self image, at least the horrid cramps that soon set in started to take his mind off of his thoughts. The moment the bag drained completely he pulled the nozzle out and rushed to the toilet to relief himself.

Done emptying himself completely Jason mournfully shoved the new spit lubed plug back up his slightly gaping ass. While being without something in his ass had felt strangely empty this plug once again left him feeling uncomfortably full and stretched out, his ass despite having fully adapted to the last size not at all ready to deal with this size yet. Not that Sally left him with much of a choice. At least the remainder of his time in the bathroom was less awful than it had been up until now. The warm bubble bath he slid into felt as amazing as he had imagined, despite the awfully strong floral scent. It was good to be without heels even if just for a little while as he washed and scrubbed his body.

As soon as he got out of the bath however it was right back down to business, he only got a few brief moments to dry himself before Sally insisted he'd get dressed in the outfit he had picked out. She hadn't said much all this time, but her mere presence put enough stress on Jason as it was. The outfit like pretty much all of his night time wear was made to get fucked in. It consisted of a soft pink satin coset with a red lace heart stitched on the cups right over where his nipples were. The back was laced up with a wide red satin ribbon, one that Sally stepped in to tie of extra had before letting him carry on getting dressed. The four garters hanging down form the bottom of the corset ended in red heart shaped tabs, tabs to which Jason soon clipped a pair of sheer soft pink stockings with a back seam consisting of red hearts stacked upon red hearts and ending in red stocking tops.