Wrecking the Homewrecker

Jasmine's day out

Like what had slowly become habit Jason had gone through his usual morning routine on Sunday, edging himself with the nozzle of his enema bag, which uncomfortably large contents he soon expelled only to plug his now squeaky clean ass back up. Done with that he had taken his morning bath, washed his night time lingerie and hung it up to dry while taking yesterday's lingerie down to put back in his closet, all with perfect mincing steps in his high heeled mules, the bath really the only place he could rest his poor feet a little. By the time he left the bathroom he smelled like a flower shop once more, his skin glistening and baby soft from the daily scrubbing and all the moisturising lotions he rubbed into his skin each night and morning. It was softer than the skin of any of his past girlfriends and while he didn't realise it he was also weaker than all of them by now. Then again his intense time consuming routines were simply unsustainable for anyone who had better things to do than to look pretty for whoever wanted to use them.

Stepping into his room and the only space he had seen ever since coming here, he minced right over to his closet to pick his pink frilly sissy outfit of the day, not really caring beyond the fact that it matched. Dressed in his outfit for the day, Jason then minced to the vanity to slatter on his lip and eye makeup to Sally's standards before finally putting his ginger hair back in pigtails, a slight dirty blonde outgrowth showing by now as he parted it down the middle. After spritzing some perfume all over him, not that he needed it, he was done for the day, checking himself out in the mirror just to make certain of it, just like he had been taught. Even without supervision it was a necessity as Sally did check the camera's and punished him severely for each mistake. It made him fear slipping out of the role of the complete sissy dork even slightly even when she was not around. Yesterday she hadn't found a single issue with him, and he hoped today would be the same. It was impossible to tell if she would actually look today, but it was a chance he wasn't willing to take.

Completely ready Jason minced towards the door and got down on his knees, kneeling to wait for Sally's return for what was sure to be the start of just another day like the ones he had had so far. He could only wonder how many men he would have to entertain this afternoon. As he sat there, he had a moment to think, which given his situation wasn't the best thing really. It was nice to be alone for sure, not to be directly supervised and have Sally there to only add more shame to his predicament, but then again, acting like a huge sissy with no one around only made him feel more pathetic. To think he should be by the pool, a lake, or at the beach, having fun with friends and scoring with hot girls enjoying the summer break's freedoms after an intense finals period. He could hardly remember a thing from his advanced science courses, but he knew full well that the average penis size in Cape Verde was 14.05 CM, he didn't even know Cape Verde was a country before. Likewise there weren't any hot girls around, hell he had hardly even seen people his age, most being significantly older, and while even a middle aged woman sounded like heaven compared to all the cocks and asses he had had to deal with, the only things of them he had really seen were their feet.

This place was anything but a nice beach either. Hell instead of getting a tan he had grown paler, not having seen a ray of sunshine that wasn't filtered through a window. Paler definitely fitted his complexion as a freckled ginger sissy dork better though much to his regret, oh how he wished he was somewhere else, anywhere else than this horrid room, Jason thought, not realising how he would come to regret that wish. In either case he was torn out of his thoughts when the door to his room opened only for a pair of black tights covered feet in a pair of fuzzy slippers to appear in front of his eyes before the door closed again. Instantly Jason reached out to slide one of these slippers off of the feet in front of him and neatly place it aside only to plant a kiss right on the smelly nylon clad foot and repeat it with the other one as he inhaled deeply, correcting his glasses with a snort in between. He definitely recognised the smell of Sally's feet, they positively reeked, yet much to his shame he could feel his butt clench around the base of his plug out of sheer excitement, a shameful conditioned reaction to the smell of feet. "Good morning Miss Sally, there's nothing quite as great as getting to smell your feet in the morning." He gushed, supressing a groan as Sally burst out laughing. He needed to say it, but at the same time it hit all the harder with how his body was actually reacting like it was the truth.

"Hahaha, absolutely pathetic dork. I bet you dreamt of getting to sniff and kiss my feet again didn't you? You really love them don't you? Us women might not have a cock to fuck you with like you so desire, but you love our smelly feet don't you? Luckily it's the only part of a woman that really get you going cause I doubt any woman in her right mind would let such a pathetic sissy dork touch any other part of her. In any case sissy, that's enough indulging of your pathetic fetish, breakfast is ready, so get up on you knees and start eating." Sally taunted, trying to humiliate her sissy stepbrother was never getting old. After hearing those same things over and over, one might think that he could get used to them, but they kept on stinging terribly. Even more so as of late as the words became more and more true each day. In either case he was happy to get his breakfast, not because he liked sucking the huge ten inch cock shaped teat which was by now fastened to the front of his breakfast bottle on Sally's strapon harness, but because he at least didn't have to reply to Sally's horrid taunts. Much to his shame, swallowing all ten inches of that silicone cock was rather easy for him now, even when Sally took charge and used his pigtails to face fuck him.

With his breakfast swallowed from that huge cock Jason was ready to go get on his bed to be tied down and edged into mindless over arousal to get him incredibly horny and eager to please the men who he assumed would come this afternoon. His days filled with edges and orgasms were really rubbing off on him, they left him so much easier to get aroused and having edged himself with that nozzle plus the smell of Sally's feet had only kicked his almost baseline arousal up another notch. At this rate he doubted getting him edged was even necessary. Just the sight of a cock would make his ass clench in anticipation the same as smelling Sally's feet had. Hell, the smell and taste would do so even more. Cocks weren't just the only things giving him orgasms anymore, they were also genuine turn ons in their own right much to his shame. No matter how he wanted to there simply was no denying that.

Much to his surprise Sally didn't tell him to get up on the bed like every morning. Instead she locked a sturdy pink collar around his neck, connected to a chain leash leading to a matching pink handle she was holding. "Alright sissy why don't you help me out of this harness here and into this skirt? We're going for a walk. You can just leave the harness on the floor, no need to take it anywhere." Sally instructed with a grin as she looked down on her surprised stepbrother who was dealing with some very mixed feelings. He could hardly believe that he would finally be allowed out of this room, maybe even beyond this house which was pretty much what he had wished since getting here. Once outside he might finally be able to get away from Sally, alert somebody, but the though of anyone seeing him like this was terrifying at the same time. It would require a lot of courage and his time here had already destroyed a lot of his confidence making it all the harder.

In either case none of that mattered just yet as he wasn't outside yet, locked in his room with Sally he knew better than to show any signs of disobedience, knowing that they would be punished swiftly. So without delay, he helped Sally out of that harness, dropping it and the huge cock which made even the bottle his breakfast came in look small, to the ground only to help her in her skirt instead. It was a simple black skater skirt to go underneath her white t-shirt. He had barely pulled it all the way up to settle on Sally's hips, when she pulled him up with a firm tug on the leash. "Come on dork, time to get a move on or we'll be late." Sally chuckled, barely giving him time to get on his feet before pulling him out the room and into the hallway. It was a struggle for Jason to stay upright, but luckily, or unluckily depending on how you looked at it, he had had more than enough practice on heels not to topple over, although with Sally's rough pulling it was impossible to keep his mincing steps as small as required. On top of that her mention of being late had him worried, late for what? It didn't sound good, and he doubted that wherever they were going would be an escape opportunity, but maybe somewhere along the way.

As Sally marched him towards the front door Jason took in as much of his surrounding as he could, for if it would ever become useful. Soon Sally demanded his attention again though, forcing him to focus back on her. "Alright pervert, time for you to get my shoes on, don't worry, you may kiss them again before you slide them in my sneakers." Sally chuckled as she nodded towards a pair of well worn sneakers. Although he was embarrassed Jason quickly obeyed, kissing Sally's feet knowing full well it hadn't just been a suggestion, and much to his shame feeling his ass clench around that plug again in anticipation. He was glad to get them in those shoes to be done with the confrontation, but the sting of knowing what a pervert he was remained.

With Sally dressed it soon became clear that maybe the way there wouldn't be the opportunity he had hoped for. Instead of out the door where one of his old neighbours might hear him, she led him to the garage where he got stuffed into the back seat with tinted windows, his collar secured to the headrest while Sally got in the driver's seat and took off for what ended up being a decently long drive. This was where this shameful nightmare had begun, in the back of a car, and here he was again, getting transported to god knows where. He tried to look around for opportunities, getting hopeful as they were driving towards the city, but that hope was getting crushed bit by bit as they started entering seedier and seedier neighbourhoods until Sally finally parked in a place where he wouldn't even have felt secure as a guy, let alone as a sissy. One thing was for certain, this was a place where he would sooner find trouble than help, especially dressed and looking like he did. If Sally could manhandle him, then he doubted the few thugs he had so far spotted would have any issue doing so. The thought of what they might do to him was scary, especially what they might do if they found out he wasn't a real girl

Jason had come to realise Sally was complete crazy ever since being forced into sissyhood, but this trip had to mean she had completely lost her mind, to come here with just the two of them was crazy. Yet that seemed to be the exact plan as Sally opened the door, freed him from the headrest and pulled him out of the car by his leash. "Come on dork, time for a little walk. I'd say I'll protect you cause you sure won't do shit, but I value my life you can be perfect bait though. If you keep all those cocks preoccupied for long enough then I can make a clean escape." Sally grinned, knowing it was pretty save, but she so loved to scare her sissy stepbrother, she didn't even have to tell him to act like the scared dork he was, he did so all on his own. It was exactly why she had parked a couple of streets from their destination, so she could really savour his fear.

Despite his hatred for Sally Jason still ended up staying very close behind her once they had made it out of the car. Sally might have said he could just form the perfect bait and he didn't expect her to help him one bit, but staying close to her did make him feel a little safer, which only turned his cheeks red yet again, as he realised just how big a sissy he was, clinging to his younger stepsister for protection. Still noting all the hungry looks he got made him cling to her even closer. At least with the men who came in his room he was certain that they knew he was a sissy and that aside from maybe facing a red ass he was relatively safe.

It was such a scary walk that it was almost a relief to Jason when they made it to a strange very bright and pink salon, only to step right inside. It looked like an overly sissy place which gave him the chills, but his room was even worse and he was so glad to be off the streets. It wasn't long until an older brutish woman in a pink smock and sturdy nude coloured support hose joined them followed closely, but a gorgeous if not overly frilly kind of flat chested Hispanic girl, in a similar colour schemed outfit as the older woman, but way more frilly, elegant and sexy, her legs sparkling in the light, dressed in very glossy nylons while the tall heels made them look all the sexier. Jason didn't know what to do but look down at the floor, it had been an instruction once, but now it was more of a habit as he didn't have the confidence to face anyone like this. With a loud snort he quickly readjusted his glasses, another habit kicking in which made this older woman laugh. "Hahaha, what a fucking dork, it's so great to see my work of art in action and you are right Sally, he was really born for this. So shall we start on the touch up?" Suzan asked with a grin, revealing that it was she who had turned him into this dorky sissy monstrosity. Jason knew he should be mad about it, but instead his blush only deepened as he squirmed a little, lacking the courage to shout at this woman, not that it would have earned him more than a spanking.

Sally was all too happy to agree as she handed the leash over to Suzan claiming he was all hers. She also scolded Jason asking if he wasn't forgetting something, and so mortified as he was, Jason dipped into a deep curtesy. "Hello Ma'am, thank you for making me look so pretty. I do have a confession to make, I have a huge foot fetish." He lisped only to repeat the action towards this pretty Hispanic girl which was even more painful because he was attracted to her unlike to Suzan. If he had looked up further than their feet he might have noticed that the Hispanic girl looked just as embarrassed as he did.

"Hahaha, that's no Ma'am you're talking to sissy, that's another sissy just like you. Now why don't you give my Angela here a proper sissy greeting with a hug and a kiss?" Suzan laughed as Sally had a chuckle of her own. Jason was absolutely mortified though, the only person he was actually attracted to here was in fact a guy, where all those cocks really getting to him that much? He couldn't help but wonder and shudder. Before he could fully gather his senses Suzan gave a strong tug on the leash clipped to his collar gave her own sissy a shove in its back to send them flying into one another's arms. Jason could clearly tell that this wasn't the first time Angel as she was supposedly called had to greet another sissy as she instantly wrapped her arms around him and placed her own plump filled up lips on his, pushing her own pierced tongue into his mouth as they made out. Jason for his part couldn't help but soften up a little, Angel didn't only look nice, she also smelled so nice, giving him some quick trouble with his cage, not because of anything that was conditioned, but because of genuine attraction much to his shame.

"How cute, the sissies are loving one another, in any case that's enough kissing. It's time to get to work so we can get you back to looking like the perfect sissy dork shall we Jasmine?" Suzan grinned as she tugged him along and practically pushed him into one of her salon chairs where she didn't bother to cuff him in place. Between what lay outside her salon and the both of them easily able to man handle him Jason would be crazy to try and escape. That didn't mean he was any less concerned and nervous however when Suzan took the ribbons out of his hair and brushed it out only to wash it, dry it and add a paste in the right by his scalp, a paste to colour the mild outgrowth he had. The only places he had been in to get his hair done so far were barbershops, at least consciously. Then again compared to his room this place wasn't all that bad which didn't mean he wasn't embarrassed by the beauty treatment.

"So Sally have you been happy with the freckles? Should there be more of them? Less maybe? Perhaps in different places?" Suzan asked as she set Angel on the task of doing Jason's nails, fixing the very slight out growth that had happened there as well. Sally gushed that she simply loved it, that the freckles were perfect as they were to which Suzan said something which frightened Jason to his core. "Wonderful, would you like to continue working with this henna or should I just tattoo them on so you won't ever have to worry about them fading?" She suggested and much to his horror Sally laughingly agreed right in front of him. If Suzan hadn't been holding her hand firmly on his shoulder, keeping him pushed down in the chair then he might have actually jumped up, but she was too strong to go against, besides, there truly was no place for him to go much to his horror. This tattoo was going to happen whether he wanted it or not meaning that he would soon have a real permanent freckled face and even if he could escape Sally and this embarrassing sissy life there would be no escaping his freckled face ever again. He badly wanted to prevent it from happening, but Suzan was quick to lock a posture collar around his neck and clip it to the back of the chair really immobilising his head as she got her tattoo pen out and got to work. Even if he had been able to move his head, that would have been a terrible idea by now or he might end up with a line tattooed across his whole face, after all she was using that tattoo pen on it with liberty. The best he could do now was hope for it to be over soon as the needles of the tattoo pen did sting, landing on each and everyone of his many freckles making them permanent fixtures.

By the time Suzan was done jabbing his face neck and shoulders over and over again Angel had finished doing his nails and even retrimmed and coloured his pubic patch, going as far as to help him back into the stockings and socks he had put on that morning. Now that they were both done with him, they simply released him from the posture collar and just the chair. His face was stinging all over from the tattooed on freckles which looked way too dark and unnatural at the moment, something Suzan assured would fix itself when it healed. Jason didn't even get time to process that his whole face was now permanently marked with an over abundance of freckles where it had been blemish free before, so not even a haircut would stop him from looking like a complete dork. Instead he got pulled right out of the chair and got led over to the counter where Suzan informed him that the total cost of his salon visit was 550 bucks.

It sounded ridiculously expensive to Jason, but at the same time insultingly cheap, knowing that with just 550 bucks Sally had just permanently given him freckles. It was no issue for Sally who probably didn't even need to ask her dad the money, having a nice enough allowance to afford it without issue. With just some money she didn't worry about she had ruined his life even more, left an even more permanent mark on him, he thought has he sheepishly stood by, squirming as he tried to come to terms with it while he waited for Sally to pay. That never came however, instead after letting him squirm for a good minute on end Sally gave him a meaningful shove in his side. "Well Sissy, what are you waiting for? Pay the nice lady for your beauty treatment and helping you look like the prettiest dorkiest dork out there." Sally instructed with a grin as Jason looked at her in shock.