Wrecking the Homewrecker Pt. 27

Jasmine's new wardrobe

When Jason clumsily minced into the room again he could feel his glasses had lowered once more and instantly corrected them with a push down the middle and a loud snort as demanded. It was more than enough reason for Sally to laugh her ass off once more, the first time Jason had fixed his glasses without needing a reminder. Jason couldn't help but blush beet red, he felt like a complete fool, but then again, even without fixing his glasses he did, the shame was ever lasting given his outfit and room. At least it had saved him from getting his balls zapped.

"Oh god you are such a fucking dork Jasmine, that was so fucking precious and I bet your clitty is loving this as much as I do, after all it can avoid a punishment now so keep that up. In any case why don't you have a seat so I can explain your next task?" Sally grinned as she signalled to the small desk in front of the platform hers was standing on, the one she was resting her shoes on. She followed his mince through the room intensely with a big broad smile plastered all over her face, oh this was just too good.

After a dreadful awkward mince, managing his heels well enough to stay up right but still be in the constant fear of falling Jason finally manage to get over to the small desk. Sliding into the chair was rather difficult as the space was only just big enough for him to sit. He couldn't help but groan a little as he felt his plug slide a little deeper when seated. It didn't escape Sally's attention either as it was once again reason for laughter. "What's the matter Jasmine, not quite used to having your sissy pussy stuffed yet, well don't worry I'm sure you'll get used to it eventually, a few weeks of wearing that plug and you'll feel empty without." Sally grinned as Jason looked up at her in horror made even more precious by his new looks.

He couldn't imagine ever getting used to any of this, especially not to that plug. It was a terrifying prospect and deep down he feared that it would eventually happen. At least if he didn't manage to get out of here real soon that was. While Sally's taunts were embarrassing, so was his position now. Sitting at the small cramped desk he had no other option than to look up at Sally over her legs as he was face to face with he dirty soles of her shoes.

"As you may have noticed sissy your room is currently a bit of a mess, the floor littered with bags upon bags. I can tell you that they contain your new wardrobe, but aside from that I can't tell you a lot more. After all I really don't want to spoil the surprise. Your task for the remainder of the day will be to unpack everything and hang it in your closet, but of course there is no fun in just unloading those bags and jamming everything in the closet. I want you to pull out each piece one by one, hold it up and pay it a compliment followed by paying a compliment to how you think you will look in it. they better be good as I will be your judge and if you don't look happy and gushy enough you will get punished. Glasses!" Sally said, interrupting her explanation with a simple command as she gave her sissy stepbrother a quick zap to the balls for not correcting of his own volition soon enough. The zap was followed by a loud yelp and a snort as Jason hurried to fix his glasses up on his nose.

"Good, as I was saying you will show your gratitude by paying every item you pull out of those bags a nice enthusiastic gushy compliment. That is not all though, you will of course also thank me for providing you with said item. You will do so verbally and with a kiss, a kiss right on my soles as there is no way I'm letting a sissy anywhere close to my face. Of course you'll get the privilege to remove my shoes before you get to that, and because I want a nice memory of your gratitude you'll paint your lips before every kiss so you can leave a nice bright mark." Sally explained to the increasingly horrified Sissy at her feet. As Jason quickly corrected his glasses once again, trying to avoid another zap before Sally would make a remark.

Just as Sally was about to explain how to apply his lipstick Bernice walked in tugging along Madison on a leash. The stunning blonde college girl skilfully walking along in nothing but her ballet boots, stockings, under bust corset and collar. Her perky breasts, neatly shaven pussy and her cute bottom were on full display. Sally instantly broke into a big grin happy to welcome Bernice for the main event, especially since she knew that probably meant her stepsister had already had plenty of fun of her own. Not only that, but this was a further opportunity to crush her stepbrother's ego even more. Just like they had agreed upon before.

Having heard the door open Jason quickly turned around in his chair as well, mortified to be seen like this, but at the same time he was hopeful as well. Having turned around before seeing Sally's grin he hoped that maybe someone had found out what Sally had done to him and was here to save him. Seeing one of their older neighbours, one his sister had often complained about, grinning while she pulled along a gorgeous girl on a leash instantly dashed that hoped though. Jason couldn't help but ogle this girl. She was even more gorgeous than the girl he had kind of started dating during his finals, a friend with benefits he knew wanted to be his girlfriend and she had been nice to have fun with to alleviate some stress. He had even agreed to plan a small vacation with her during the summer break, but he had no intention of letting it become anything serious. This girl however was prettier and dress so much sexier than any girl he had ever fucked.

Ogling Madison Jason couldn't help but groan loudly as his cock instantly struggled to grow rock hard only to be viciously kept limp by the tight cage. Making matters even worse a painful zap to his balls quickly followed as Sally shouted. "Glasses!" Mortified Jason snorted as he once again pushed up his glasses in front of Bernice and this hot girl. It was better than more punishment, but not by a lot as he was deeply mortified. As if having to appear in front of such a hot girl dressed like he was wasn't bad enough yet, he was forced to further humiliate himself like this while Sally and Bernice shared a good laugh at the display.

"Looks like our sissy dork is pretty smitten by your slut Bernice, so much that her glasses slid right off her nose, how cute. Slut, what do you think of our sissy here, doesn't she look pretty?" Sally enquired as Jason once again blushed beet red. He couldn't believe his stepsister was so confidently addressing this hot girl like this, but then again given how she was being led around on a leash by a woman close to triple her age, and what Sally had done to him he shouldn't have been surprised.

What did surprise and shock him however was the disgusted look he got from this girl. "She is pretty, if you mean pretty pathetic that is, I would never want to be seen with such a dorky loser like her. Hell I would much rather spend my day eating either of your asses or rimming a real man while getting my pussy whipped than even considering to let that sissy give me a peck on the cheek." Madison spoke viciously with a bitchy flair that came natural to her, but one that she hadn't used in ages. It was what she had been told to say with the promise of a big reward if she could say it with convincingly sincere disgust.

It worked wonders, just as intended by Sally and Bernice as they could see the devastation on Jason's freckled face, getting rejected so harshly by such a gorgeous girl. He had never been rejected and he couldn't imagine anyone wanting to rim either of these horrid women. Adding insult to injury Sally once again zapped his balls and shouted. "Glasses!" making him respond with a loud snorting correction after just having been called a dorky loser. He really felt just like that right now.

"Oh Sally, I'm sure you must have been mistaken, I don't think this sissy is smitten with my slut like that. I'm sure she's just jealous of my slut's curves wishing she had some like these all of her own so she could attract all the men she wants. Didn't you tell me that Jasmine here love men, and when it came to women only had like a fetish for their feet and nothing more?" Bernice inquired, carrying on their staged embarrassment for Jason. Jason for his part couldn't believe what he was hearing, feet grossed him out and he certainly wasn't even the slightest bit into men, this was just messed up, then again all that had happened here already was just completely messed up.

"You're probably right Bernice and yes, Jasmine has a huge foot fetish but is completely gay otherwise. In fact I imagine she's very excited to unpack the new wardrobe both for all the pretty things she'll have and for how I allowed her to thank me and now by extend you. Why don't you find some place comfortable Bernice? Oh and can I borrow your slut? I think she should put her money where her mouth is and in this case her mouth where my butthole is so she can show off how much more she desires to eat my ass than letting this dork here give her a peck on the cheek." Sally ordered as Bernice happily agreed, releasing the leash and sending Madison on her way with a slap to the girl's bottom. Meanwhile Jason once again corrected his glasses with a snort before he could get zapped.

As Madison reached Sally's side Sally quickly got up and Madison sat down in front of the chair, resting her head back on the seating before Sally took place again, lowering her tights and panties slightly to wiggle her fat ass in place on the hot girl's face only to let out a moan, presumably when this girl's tongue wiggled up her ass. It was devastating for Jason to see her actually put those words into action and prove this hot girl really loved his stepsister he had bullied over her looks her ass more than she did him. Making matters even worse Sally now kept her legs spread slightly as it was more comfortable when sitting on a face. It resulted in Jason having a perfect look of this girl's breasts, proudly stuck out to him underneath Sally's desk making his cage a constant nuisance as his cock struggled to get hard. Bernice for her part had just made herself comfortable on his new bed.

"Alright Jasmine now that's settled let's continue with our explanation shall we? Like I said you will give my feet a big kiss to show your gratitude, and you'll do the same for Bernice. You will clean off and reapply your lipstick before every kiss and I better see you improving with practice. Take your time as we have plenty of that. That delicious pink base coat you are wearing should last a couple of days so that shouldn't wipe of with the rest of it, but it'll show clearly whether or not you did a good job when you trace it over with this fire engine red colour. All the pink should be covered, but you shouldn't cover more than just that pink. To apply it just steadily trace it over your upper lips then your lower lip, then smack them together to smooth things out." Sally instructed as she handed her sissy stepbrother a tube of lipstick, a pink heart shaped compact mirror and a package of makeup wipes that shouldn't smudge or hurt the makeup Suzan had applied.

"Now to get started you may thank us for your brand new look, take off my shoes and give each of my soles a kiss then do the same for Mistress Oakley. Remember apply a new coat of lipstick between each kiss and I want good long pecks, five seconds of contact at least and a deep audible sniff to go with it. Now chop chop, get started sissy because you still have a lot of work to do before bed time." Sally smirked letting out an occasional soft moan as she looked down on him.

Jason was completely mortified, he couldn't imagine thanking either of these horrible women for this, let alone kiss their feet for it. The thought alone disgusted him. "Please Miss Sally, haven't you put me through enough already? Can't you just leave me alone?" Jason lisped trying to get out of this horrible task as he once again corrected his glasses with a snort, trying to please Sally and heighten his chances. He didn't have a lot of hopes, but it was worth a try at least. He might not be able to get out of this horrid situation, but at least he may be allowed to feel sorry for himself in private.

This time Sally didn't react, instead Bernice rose right to the occasion. "Jasmine, you ungrateful little bitch, we won't tolerate back talk. A sissy should only be heard when she is spoken to, and even then she should only say what is expected of her. Right here a yes Miss Sally would have sufficed. Now get your ass off that chair and bend over the desk, you've earned yourself a reminder spanking." Bernice said not showing any patience, or giving any chance to just let this slide with a lecture. Ever since Suzan had made Jason look so good she had wanted to get her hands on him and this was a perfect opportunity.

It took Jason completely off guard though, he was expecting a no, or a threat to obey at most, but not this. "Please Mistress Bernice, it won't happen again I swear. I'll do what I have been told just please don't spank me, I've learned my lesson." Jason quickly lisped, trying to get out of getting a spanking on top of all this other crap.

"You haven't learned shit Jasmine as you just did it again, so your punishment has just gone up from ten to fifteen spanks, now get in position before I make it twenty and keep count while I spank you. I believe I should get a thank you as well for every hit." Bernice sternly spoke as she marched right to the side of the desk. Defeated Jason wormed his way out of the crammed space minced over to the side and bent over the desk, his flimsy skirt rising right up exposing his already slightly reddened cheeks through the hole in his panties. He couldn't believe that after having to deal with his stepsister he would now have to deal with this horrid old woman, but he knew better than to protest again. He couldn't take Sally in his current state, let alone taking Sally and Bernice at the same time. His best and only course of action was to just take this spanking and get it over with.

"Oh my, you clearly haven't learned shit yet Jasmine. I see you already took a spanking, that sissy grade of yours seems to be down to a B- already. In any case, let's not delay now shall we?" Bernice smirked referring to the rosy shade of his buttocks that kind of matched a slightly darker version of the trim corresponding with the letter B next to the opening in the back of his panties. Without delay Bernice landed a harsh slap with her palm on the exposed already slightly tenderised flesh making Jason yelp.

"Ahhh! One thank you Mistress Bernice." He lisped, not wanting to make things worse by disobeying. The slap stung way more than Sally's slaps did, being both harder and on more tender flesh, but it was by far his ego that hurt the most from this assault on his bottom. His balls might not get shocked this time, but that plug pushed into his prostate with every blow. Then there was also the fact that he was now spanked by this horrid old woman much to Sally's obvious amusement rather than just by Sally in somewhat private.

By the time they reached fifteen, Jason's ass had turned several shades darker red and so had his freckled cheeks, completely mortified over the second spanking he had just gotten. "There we go, I hope you learned your lesson now sissy as we wouldn't want to see that D you sport now turn to an F now would we? In any case, I think you know what to do as Miss Sally so eloquently explained it to you. I better see enthusiasm and no more complaints or your next spanking will be with the paddle." Bernice said as she finally stepped and got comfortable on the bed again.

Fearing how bad the paddle would be Jason wasted no more time as he took a spot in the middle of the room, quickly correcting his glasses with a loud snort and lisped with a wide but obviously very forced smile on his beet red face. "Miss Sally and Mistress Bernice, I would like to thank the both of you so much for this wonderful new look. Please allow me to show my gratitude to the both of you."

With that he minced right back over to the desk where he had been handed the makeup wipes, lipstick and compact mirror only to clasp it open and liberally apply the red lipstick as well as he possibly could. With only the use of his thumb and index finger available and these horribly long nails it was very awkward to handle these tools, but he managed. If anything the restricted movement of his manicured hands made the sexy process of putting on lipstick look down right dainty, even though the results were terrible. It wasn't an even coat at all, having gone out of his lip line in some part while not covering enough in other areas. Sally didn't scold him this time though, the first time was a baseline, and she expected to see improvement over time.

Now that his lips were painted Jason moved to the second part of the expectations which was even worse. He didn't want to kiss his bitch of a stepsister's feet at all, the thought alone disgusting him, but he surely didn't want to make it worse by facing the paddle first so reluctantly he started untying her laces which was easy enough despite his restrictions. Sliding off her shoes was another matter though with how little gripping strength just two fingers offered. His only reward for managing this task being a strong waft of Sally's smelly feet slapping him right in the face making him even more reluctant to go through with this.

Nevertheless he did as expected of him. Leaning over the desk to Sally's feet, fully aware that his panty covered ass was on full display, only to then cringe and gag as he planted his freshly painted lips against the damp light grey soles of Sally's socks, forcing out a deep audible sniff in the process. Given the thick tights, the socks and the sneakers in summer it was no surprise that Sally's feet smelled this horrid, and Jason was absolutely certain that Sally had done this deliberately. As bad as this was it was nothing compared to the horror he felt when one of his gags turned into a loud moan.

Without warning the plug in his bottom had started vibrating strongly, pressuring that same spot that had brought him to a near edge during his second enema. He couldn't believe he was actually moaning while doing this, or that it was because of the toy in his ass that he was moaning. He couldn't figure out which part was worse, only the entire situation was completely horrifying.

Sally and Bernice were laughing their asses off however. "See Bernice, I told you this pathetic sissy has a fetish for feet, I mean they are simply rank and she might have play gagged to keep up the appearance, but she simply couldn't contain that moan. In any case refresh that lipstick and kiss the next one you sissy pervert" Sally laughed as Jason pulled away from her foot, leaving behind a bright red stain from his lipstick on her sole.

Jason could only groan as he carried on with the task at hand, while he was loudly mocked for his supposed foot fetish. No matter what he said though there was no way to make these horrid women stop, at least the makeup wipe he moved to remove his now somewhat smeared lipstick smelled way better than Sally's feet did. Much to his horror however the pink lipstick underneath hadn't budged at all upon inspection when he opened the compact mirror. His glasses on the other hand had slid down so he once again fixed them with a loud snort and started on a fresh coat of lipstick to repeat the process on Sally's other foot.

Just like on the first kiss the butt plug kicked off once more as Jason sniffed, and two more times when he did the same with Bernice's sheer nylon covered feet, which smelled bad, but completely different compared to Sally's feet. It was definitely no accident, but he knew better than to complain. Having fixed his lips, kissed feet and corrected his glasses four times in quick succession Jason was finally ready to start unloading the bags.