Wrecking the Homewrecker

Jasmine gets to cum

Despite the fact that Jason's prospects were to suck yet another one of those horrid bottles empty through those embarrassing teats, and to have his bottom filled until he came, he was really looking forward to Sally's return. His need to get off had only gone up rather than down, it was insane, he could hardly focus on anything else making it a real pain in the ass to do his makeup. Nevertheless he tried his very hardest to apply all he had learned to create the perfect look. After all he badly wanted to do a good enough job to get his reward from Sally even if the reward would be embarrassing.

Even after he was done with his makeup Jason continued primming his look, making sure his ginger pig tails and bangs were in their perfect place, that the bows holding them together remained perfect, that his stocking seams remained straight that his skirt was properly fluffed out. Even after going over it once he went over it again, completely unprompted out of nothing but an intense need for an orgasm. Even though Sally hadn't told him to do this, he didn't want to fail on any part of his look out of a fear that Sally might decide not to give him an orgasm anyways if she noticed anything wrong. He didn't even notice how foolish he looked primming in front of his mirror while occasionally correcting his glasses with a snort. His focus was way too pinned on the details of his look for that.

Sally who was watching him through the camera feed couldn't help but be highly amused, that plug had really done a number on her sissy stepbrother and she loved it to bits. It served as a perfect twisted motivation that would come crashing down hard once she gave him what he was aiming for, it was perfect, even better than the threat of a severe spanking. Those threats would never bring him to do more than what was required, unlike the promise of a reward he desperately needed and depended on her good will.

Enjoying the view too much Sally took her sweet time getting a bottle of sissy formula with a cock shaped teat yet another inch longer ready for him. She was just curious whether or not he would keep up his primming or if he would ever just start waiting for her. The fact that he didn't stop for fifteen minutes straight after redoing his makeup was downright hilarious and basically told Sally that he wouldn't stop until she arrived with his dinner, a dinner she eventually moved up the stairs with once more, very pleased with how sissy stepbrother was acting like the biggest sissy dork she or pretty much anyone else had ever laid eyes on.

Her joy just carried on as she entered the room only to spot her sissy stepbrother mincing right over from behind his mirror. The mince was absolutely perfect and the big simpering smile baring his braces was precious as well, a slight hint of shame was still visible in his eyes but it was pushed way back behind glazed over lust. Upon his arrival before her he instantly dropped into a perfect curtesy, then with a jump and a clap of his hands announced. "Oh Miss Sally, thank you for preparing my diner for me, could I please please please suck my yummy dinner out of your deliciously big cock?" Jason asked, a little scared to see it had grown bigger once more, a nine inch monster dildo sitting on top of that horrible pink bottle, but that didn't stop him from giving this greeting his all. After all failure to act according to whatever standard Sally set could be bad news for him even if his look was perfect. It was the whole reason why he was laying it on so thick, because it was his safest bet.

"Of course you may Jasmine, after all I made it just for you. I can't imagine anyone but a huge cock loving sissy would want to eat like this, much less eat this pink crap from the bottle." Sally spoke, loving how over the top happy her sissy stepbrother acted. She loved how he once again used pretty much the same words from lunch, slightly changed to be even more pathetic, just to ask her to suck this dildo. She hadn't even had to tell him to ask nicely, it was perfect. All she did was taunt him a bit more and stick out her hips with the bottle and large dildo dangling lewdly between her legs, reaching below her knees in an extremely intimidating fashion. After all the monster size of the dildo came on top of the size of the bottle.

She didn't need to do anything anyways as Jasmine despite a slight faltering in her smile out of sheer shame over the taunts Sally had directed at her, taunts that rang all too true. Jason really felt like the sissy Sally called him and his reasons for acting this way didn't make it any better. He still really needed that orgasm though, more than almost anything so he quickly brought the simpering smile back on his face and performed another jump and clap as he spoke. "Thank you so much Miss Sally, you're the best." In his best high pitched lisping voice before getting down on his knees and lifting the bottle up to make that tip of the dildo line up with his swollen perfectly painted lips. Without delay he wrapped his lips around it and started showering the head with attention before sucking his way down the shaft. It was a slight struggle to get all nine inches in his throat, but in the end he managed to get it done and suck a first gulp of his pink formula out of the shaft with well practiced ease.

Sally just watched down on her sissy stepbrother with glee as he gave a porn star worthy performance on the cock shaped teat. With proper motivation and nothing else to do than to practice becoming the biggest possible sissy on all fronts all day long Jasmine was making rapid progressions much to Sally's glee. Controlling the entire environment was definitely a huge plus. Her sissy project was way easier to control than her stepmother with all the restrictions making it way more fun as well, but then again she couldn't complain as she had Rose well under her thumb as well. By the time she came back to perform her slut duties on Tuesday Jasmine and from the looks of it Cunny would be very obedient already. Maybe not genuine obedience just yet, but that coming from a sense of helplessness and a fear of consequences which was close enough for her.

When Jasmine finished her bottle in record time Sally simply pulled the cock shaped teat from between her lips and pulled back. The once again ruined makeup look was simply precious, but she didn't bother staring at it for too long. After all she couldn't wait to relieve Jasmine of her arousal, the third and final phase of the punishment she had put her sissy stepbrother through after his defiance this morning. Despite how much he craved some release, she was certain she would like this more than he did. "You've done a very good job Jasmine, you've looked and acted like the perfect sissy, so now that you've gotten your meal I think it is time that you got your reward as well. Why don't you freshen up while I prepare to give it to you? After all you want to look like the perfect sissy for your reward, don't you Jasmine?" Sally asked with glee already knowing what the answer would be, there really would be only one acceptable answer and she doubted her sissy project would screw up now.

"Yes Miss Sally, thank you so much for the meal. I'll get right to it!" Jason spoke with his ever more natural sounding high pitched lisp, totally ridiculous, but more natural like it was his real voice rather than one he was trying to adopt. With another curtesy Jason minced right back over to his vanity table to touch up his makeup for what felt like the millionth time. Given how it instantly got ruined time and time again it felt like such a pointless task, nevertheless Jason did it once again without complaint. If he looked his best then finally he would get to cum which was all that mattered right now.

This time Sally didn't bother waiting after she saw that her sissy stepbrother was primming in front of the mirror again. While he had touched she had put on her special strapon and cut a hole in the front of her tights to fit it through. She might not want to use his tongue, wanting to make him pussy free even though she knew he wouldn't want to eat her pussy. He didn't have taste buds in his ass though so even though her special dildo would end up squirting his ass full, it would only add to the realism of getting penetrated rather than giving him an actual hint of pussy so it was okay for her continued plans. With her fake cock that perfectly transferred the feelings of the shaft to her own pussy she walked back up to Jasmine's already looking forward to literally fucking her stepbrother up.

Barging into the room she was quickly met by her sissy stepbrother who met her with yet another curtesy and who's eyes went wide as he spotted the silicone cock dangling from her crotch, piecing together that his reward wouldn't just be permission to get himself off with a toy like the day before. "Nice isn't it sissy? You've taken your punishment well and you've definitely earned your reward, I don't think I have ever seen a more pathetic sissy in my life and you've only grown in a bigger sissy throughout the day so I would definitely say you are finally getting in touch with the real you. Now I know you would've been happy with just an orgasm masturbating with one of your toys, but that would have been just a usual night for a sissy dork like you. That wouldn't be a reward now would it? No it wouldn't so I was thinking about a perfect reward and I could only come to this solution, I know it's not a real cock, but there is no better reward for a sissy than a good butt fucking now is there Jasmine? Do you want me to fuck your ass nice and hard with my big cock?" Sally asked with a big grin, really savouring this moment.

Jason really didn't like the look and prospect of this, it was so much worse than masturbating like a girl which had been terrible enough already. He really needed this orgasm though and he had no doubts in his mind that this was the only way he was going to get one. As bad as it looked, his sheer need for that orgasm motivated him to continue to act like the complete sissy he knew Sally wanted him to act. "Oh yes Miss Sally, a sissy like me couldn't wish for a better reward than getting fucked nice and hard, thank you so much Miss Sally to make this happen." He lisp with an excited hand clap and jump. It might be bad, but he had no doubts that that dildo would be able to tip him over that maddening edge he had been on for so long so he may finally enjoy some relief from this tormenting, frustrating, arousal.

"I knew you would be exhilarated at a chance to get that sissy pussy of yours stuffed and used like it is supposed to be used. Now make it alluring for me, go and lay on your bed. You can lay on your back and flip that skirt of yours up for me sissy, show off those pretty panties and that useless locked up clit of yours while I show you what a real cock is like. I know it isn't quite the real thing yet, but it's infinitely more of a cock than that useless thing you have dangling between your legs." Sally savagely spoke, not sparing her stepbrother one bit as she threw every insult she could think off at the overly aroused and mortified yet eager to please for now sissy.

Dipping into another curtesy Jason quickly minced over to the best, trying to brace himself for what was coming. Even in his arousal clouded mind this was more than he had bargained for, but he just couldn't screw his chance for an orgasm, he had come too far for that and the need was just too great. Getting down on his back on the bed only added to his shame as he once again had a perfect view of his sissified body in the mirror above. Even he had to admit that his cock looked utterly useless being nothing but a pink metal nub poking out through a hole in his overly frilly panties as he flipped up the very short skirt that didn't need much raising at all to leave him completely exposed. Sally was painfully right that her toy looked more like a cock than his did, it made her previous words cut all the deeper yet he kept looking forward to finally finding himself the relief he needed so instead of trying to preserve any modesty and dignity however he waited for his stepsister and now Mistress to come and fuck him.

It was a role Sally was all to happy to take on as she eagerly jumped onto the bed only to roughly spread Jasmine's stocking clad legs wide apart and get in between them. With a big grin she promptly rested her silicone cock on the front of Jasmine's panties right next to her cock cage. It put a big emphasis on just how huge her eight inch dildo was compared to Jasmine's cage and she just loved the shame it brought on the sissy's face as Jasmine looked down on herself from the mirror above. "See, so much better than what you have sissy. Now I want to make this reward extra special for you, so I've decided to indulge your little fetish at the same time." Sally taunted with a grin, rubbing Jasmine's worries in even more.

With that said she took off one of her well worn slippers and handed it over to her sissy stepbrother with a big grin. "Here you go Jasmine, a nice stinky slipper for you to smell, I know how much you love feet, so why don't you hold this up to your nose and sniff loud and clearly for me? No sniffing no fucking, and if you screw up you can count on another punishment that will make this last one look as child's play." Sally grinned as she watched her sissy project take it in her hands, the well worn pink slipper failed to look feminine at all clamped between her daintily gloved and manicured hands as Jasmine obeyed, pressing the insole to her nose and sniffing deeply.

The scent of Sally's feet was overwhelming and utterly obnoxious, a mix of stale and fresh foot sweat, but after the morning with her socks taped to his nose Jason managed to keep himself from gagging over it as he gave them a deep sniff. If anything much to his horror he even felt his ass clench over the now silent butt plug as the start of a conditioned reaction to the scent of Sally's feet. It was utterly mortifying, but still the sheer need for an orgasm remained way too great for him to refuse just about anything Sally demanded of him. As scary as that dildo resting on the front of his panties was, he needed it to plunge into his ass so he could finally tip over the edge.

Sally could only grin, her stepbrother looked just too ridiculous with his ginger pigtails, his nerdy glasses and is face half hidden under the insole of her well worn slipper. She just loved the view, and it definitely put her in the mood for some fun, fun she was going to take at the expense of his ass as she dragged out the wait a little longer by casually taking another one of those small pink condoms and securing it right around the tip of Jasmine's cage to catch everything that would inevitably dribble out so she could easily feed it back to him.

With a huge grin she then reached underneath Jasmine and pulled the big butt plug out of her ass with a loud plop. She could only chuckle as her sissy project let out a moan, the simple stroke over her prostate while she was this aroused enough to cause one telling Sally that this would be way too easy. She would have Jasmine filling that tiny condom in no time at all at this rate. Now that the plug was out Sally squeezed a drop of lube onto her silicone cock, before roughly throwing Jasmine's stocking clad legs on her shoulders and lining the tip of the dildo up with the sissy's slightly gaping ass right through the hole at the back of her panties. Hearing Jasmine whimper as she felt the slick cold tip press up against her hungry hole.

It was simply thrilling to Sally that her stepbrother's pleasure was entirely into her hands through a means so embarrassing to him. This was what power felt like, and the more she got to experience it the more addicted she grew to it. Deciding to no longer keep him waiting, she roughly shoved her hips forward, plunging her cock deep into Jasmine's well stretched ass. It got her a quick yelp followed by an involuntary moan that drove Sally wild. Despite her dorkiness Jasmine was a hot sight to behold and the fact that she was moaning underneath her smelly slipper over getting fucked made it all the hotter to her as she pulled out slight only to slam right back in as she started to pick up a pace.

Just like Sally fucked him harder, Jason's moans grew harder as well. Within a few thrusts he could feel, his arousal build up to another edge, one he would finally get to tip over he thought with anticipation. The sight up at Sally looming over him with a big grin and a red face from effort was horrible, but not as bad as the look down upon himself getting fucked like this in the mirror above was. While he could easily take the dildo after being stretched with plugs, the sheer length and grith combined still made him feel absolutely stuffed, especially since it never stayed in long enough for him to really get used to it. Another grievance was the horrid stench of Sally's feet from her slipper, but despite all that, Jason felt overwhelmingly great, he trusted that this cock wouldn't stop right before the point of no return and he really looked forward to his orgasm with huge anticipation.

Only a few minutes in this intense fuck that moment finally approached, he was moaning constantly, his breathing heavy drawing in the scent of Sally's feet with each and every breath as the silicone shaft in his ass kept sliding back and forth over his overstimulated prostate until the pleasure built up and all that pent up frustration escaped in a moment of pure pleasure more intense than any pleasure he had ever felt. He couldn't help but let out a muffled scream while his eyes rolled back into his head and his caged cock despite it's painful situation having continuously struggled to grow hard in its tight prison, shot the small pink condom full of cum. It was so much different than an orgasm achieved through his cock as well, like it came from deeper in a way. Unlike using his cock this pleasure seemed to continue as Sally carried on fucking his ass getting into a moaning fit of her own.

Looking down on her squirming moaning sissy project to wrapped up in the intense orgasmic bliss to think of anything else Sally couldn't help but feel triumphant. The sheer power it made her feel combined with the heavy clamping down of Jasmine's ass transferring so much more pleasure from the shaft to her own pussy got Sally worked up faster than she expected motivating her to pick up the pace even more. She may have accomplished her mission of making Jasmine cum around her cock, but she wasn't finished with the sissy yet, not by a long shot. It wasn't Jasmine's pleasure she was after, it was the shame that would follow and her own pleasure of course. She wouldn't even think of stopping before she had an orgasm, and so she kept on pounding away.

It took Sally a while longer to get to an orgasm than it did her sissy stepbrother, after all, she had been completely satisfied by Cunny earlier so her need wasn't as great as that of Jasmine who had been frustrated all day long Then again unlike Jasmine she loved every aspect of this situation and she wouldn't trade it for the world. Her non stop pounding in the mean time never allowed Jasmine to fully recuperate from her intense orgasm, in fact it eventually even tipped the sissy into a second orgasm, a little before hers started and she drove the dildo all the way up into Jasmine's ass, letting out a loud carnal moan of her own as her orgasm got redirected through the silicone shaft only to squirt deep into Jasmine's ass creating another new and strange feeling within the sissy.

After taking a brief moment to calm down Sally finally pulled out with a loud pop only to pop the plug right back in and take the overly full sissy condom off of Jasmine's cage. With that done she just sat down next to the still breathless sissy who looked totally out of it still, the second orgasm having been nearly as intense as the first. Then again Sally didn't mind watching and waiting at all, especially not since Jasmine still had her slipper clamped to her nose, too out of it to even form any real thoughts or actions. Without any further stimulations that would soon change though.