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Chapter 24
Jake took his time contempting his options. His need for an orgasm was definitely there, but it wasn’t all that urgent yet so he didn’t really need those four extra points. Then again he was still in the negative as far as his score was concerned so if he were to somehow someway earn himself another penalty some extra points could potentially save him from a more severe punishment. Then again, with or without those points he would have a bit of a buffer from the orgasms and pedicure alone, and he really didn’t want to py into this twisted game of Valeria any more than he absolutely had to so in the end he decided to give Valeria nothing and stay silent.
“My nail polish is in the drawer over there sissy, so lets get started on our matching pedicure shall we?” Valeria asked with a big smile that didn’t waiver for a second. It made Jake feel as if he had hurt himself more than he did Valeria. She didn’t seem to care about him not giving her those massages at all. He wished he could also deny her request for a pedicure, but that had been more of an order than a request and she had made it very clear he shouldn’t deny her anything she explicitly asked for.
With a heavy heart he shuffled the short distance towards the drawer she had pointed out only to retrieve the box with various nail polish colours Valeria had collected over the years only to shuffle back to her. Jake did not like what he saw at all, there were a ton of polishes, each one way too colourful for his liking, then again even the clear protective coat he had been wearing for a while now was too much for his liking. The best colour if he had to pick one was the soft pink one. He guessed it was the closest to the natural colour of nails, but that was about it, close or not, he didn’t like it one bit. At least there was no reason anyone should ever see his toes, but it still remained another piece of his masculinity he would have to sacrifice, one of the so many pieces ever since that lost bet which he had come to regret sorely.
Loving the ever present blush on his face Valeria leaned over and casually browsed through her collection throwing Jake subtle gnces ever so often. The way his eyes were nervously following her hand as it moved through the bottles was just pin perfect. Unable to keep herself from teasing him a little she lifted a hot pink bottle out of the box for a closer observation. Panic instantly appeared on Jake’s face as he imagined his toe nails in that colour. It was followed by mild relief when Valeria put it back in the box only to go to panic once more when she picked out a neon green next.
Eventually Valeria picked out a pale vender coloured bottle. “I think this is what I’d like to try out. I haven’t worn it in a while and it’s pretty. It even matches with one of your frilly panties sissy. Now before I make my final decision why don’t you try it on first? You’ll get to have some more practice and I get a preview, after all when you screw up I don’t want it to be on my nails. Now before you start you’ll need to use the acetone to wipe your current polish off. You’ll have to apply two coats, plus a clear one to add some protection and a little extra gloss to it. I do think I will be able to make a final decision after seeing the first coat though. While I check it out to make sure your nails can dry for the second coat. Now get to it sissy, I’m waiting.” Valeria instructed casually as if painting their nails together was the most normal thing in the world.
Jake couldn’t help but shudder thinking about putting this colour on his toenails. It wasn’t as bad as the other colours Valeria had teased, not bright enough to be an instant eye catcher. Yet the colour still was something he would never want to be seen with and no where near subtle enough to pass even a cursory gnce. For as much as he wanted to refuse this he simply couldn’t, his cock remained firmly under lock, and even worse, with all the bckmail material Valeria had on him she pretty much literally owned him. This was no longer about his pride of honouring his bets, this was about protecting his image as well as he possibly could, the damage done to it so far was nothing compared to the damage Valeria’s video could do. He knew if it ever got out it would instantly go viral.
In his shock Jake started peeling off his stockings a little carelessly. His mind was too occupied with other things like how his nails would end up looking, to really pay much attention to handling his stockings with the care they needed. It ended up leading to yet another disaster. He pulled a little too hard to get the fragile material over his heel making it tear instead resulting in quite a noticeable run, one noticed by Valeria who was watching his every move as well. “Oops, it looks like someone is going to need to go to the store for some stocking shopping. Unless of course you’ve already gone that is, but as I recall you didn’t have any spare pairs to speak of. In any case that can wait for now, but the store is open until eight this evening so you still have time. I do want to see that pair repced today though or you will get punished. It comes to show that having some spare pairs isn’t a luxury for a careless sissy, and I guess it also shows you still very much need to wear them as you obviously can’t handle their delicacy just yet.” Valeria grinned, seeing how Jake wanted to reply only to stop himself and hang his head in defeat instead.
Frustrated by all that was happening he just tore off his other stocking as well rather than trying to save that one. If anything it only made Valeria ugh. “Dumb move princess panty lover, if you had saved that one you might have been able to pair it up with another half if you screwed a pair again. Don’t throw those out by the way, don’t throw those away just yet. Nylons are great for buffing up that shine after polishing a pair of shoes and you might as well use a pair that is ruined already anyways. In any case let’s get to that base coat cause I can already feel I’ll need your tongue again before you leave and you still have a store to go to.” Valeria ughed as Jake could only silently curse himself. Why didn’t he think of that? It seemed like just about everything he did only made his situation worse. At least he wouldn’t have to wear these stockings out now that they were ruined he guessed. It was about the only victory he had.
Sighing deeply Jake took a cotton pad out of the box only to drip on some acetone and clean up the near invisible coat of protective polish on his nails. It was hard to tell if he had caught it all, but then again he didn’t really care much. Valeria wouldn’t be able to tell either and she didn’t stop him when he was about to start applying the pale vender polish, so he guessed it was okay enough. That didn’t stop him from shuddering however as he applied a first stroke with the paint brush, leaving behind a yer of that horribly feminine looking polish. It only became worse as he ran the brush over his big toenail again, covering more of it. Brush after brush, nail after nail he applied the polish in a careful fashion not to get anything on his skin. He couldn’t believe just what a huge difference a pretty girly colour made, and he hated it. If anything he wanted to cover it up, instead he was forced to show off his nails as Valeria made a decision about her own. “Hmmm, let’s have a look shall we? Stand up for me sissy, put your hands on your hips and extend one foot forward.” Valeria instructed, having a little fun with making him pose for her.
Jake couldn’t help but feel absolutely ridiculous showing off his painted nails like that to Valeria who was just sitting on the bed enjoying herself. Given how girly it made his toes look he really hoped that Valeria would change her mind about this. Instead she just crushed his hope. “That looks just perfect. I had almost forgotten how pretty that vender can be. Dainty and delicate like yourself, and what kind of supportive girlfriend would I be if I didn’t match my toes to yours? We’re doing this. So go ahead give your toes that second coat then peel of my stockings and give mine a first.” Valeria instructed as she watched on with glee how Jake carried out her orders in defeat. All her leverage was working wonders, she had him all safe and securely trapped underneath her thumb.
With a second coat of polish his nails really looked a solid smooth vender, were bits of nail had been showing through on some pces that was now gone entirely. It looked way neater, but to him neat just meant worse. He really didn’t want his nails to look neat, not in this colour. It was only made worse by the fact that it was something he couldn’t just take off to hide it. The only way to really hide it was to cover it. Hell even if Valeria somehow allowed him to go without stocking an these horribly frilly panties for practice after how he had handled that st time, there was still no way he could get away with changing and showering with the other guys. He already dreaded to think how his teammates or hell even the coach would react when he just came in fully dressed to practice and games and left right after to shower and change alone. It was no way for a captain to behave, he had to be the glue on the team, if anything he should stay the longest, but there was no way that was happening now.
His thoughts were only interrupted when Valeria shoved one of her sneaker cd feet into his hands. There was no need for instructions as Jake instantly knew what he needed to do. With heavy heart he unced her shoe and slowly slid it off, the faint smell of Valeria’s feet rising from her nylon cd toes, bothered him, but not as much as the fact that the key to his cock was so close to him, just around her ankle underneath the nylon. So close yet so far out of reach at the same time. Not that he got any time to linger on that thought as Valeria promptly presented her other shoe only to pce her still damp nylon cd foot right onto his shoulder making their scent all the stronger much to his regret. It gave him a perfect view up her skirt right at her bare pussy which he had already brought to numerous orgasms today alone. It instantly made his cock struggle all the harder in its cage, aching for some release all the more, but not nearly enough to py along with this game any more than he had to.
If it hadn’t been for everything else about this situation it would have been an incredibly hot move for Valeria to show she hadn’t worn panties, but right now he knew he had to focus on the stockings instead. With a soft groan he reached under her skirt only to carefully pull down the top of her stocking. He was a lot more careful than he had been when taking his own off just before, knowing that he would regret it if he ruined Valeria’s stockings. Once her leg was bare Valeria casually switched feet to allow him to roll off her other stocking as well, his fingers inevitably brushing over the key to his cock cage who was giving him so much trouble at the very moment.
“Alright panty lover, time to get my toes cleaned up and repainted. I want you to pay extra attention to detail when you do because I simply won’t accept a half assed job, understood? Now get to it.” Valeria warned as she put her feet in his p only to lift one up and wiggle her neatly white painted toes right in front of his face. Jake couldn’t help but scrunch up his nose a little in response to their scent as he grabbed the foot and lowered it some to be able to clean that white polish off of Valeria’s nails. All in all it was just an excuse to take that foot out of his face.
Valeria didn’t even try to take her foot back up to his face, she perfectly could have, but she had had her fun with that, right now she just enjoyed the special attention he paid to her toes. There was something so intimate, so powerful about him paying such concentrated care to her toes and she loved it. When he had finally cleaned all ten of her nails up and started applying the polish Valeria couldn’t help but snap a picture. She didn’t bother to hide it either as she left her fsh on. The only thing she made sure of was that the brush was lifted off of her nails so he wouldn’t involuntarily ruin them when he got startled by the fsh. Which inevitably happened. It was just hirious to her when he shouted and looked up at her in shock only for her to take another picture, a perfect sequence.
“Miss, can you please delete those? I will behave, I swear, just please don’t take pictures of me like this.” Jake spoke in utter horror, he really didn’t want Valeria to have any more incriminating evidence against him. Then again now that he thought about it, it probably didn’t matter, whether it was this picture, or the video she had of him, he was equally screwed. He really couldn’t believe he had ever let himself end up in this situation, but his ego and his lies towards his friends had all made it seem like he was really into Valeria and the special kind of retion they had going. If she came out with this evidence there was no way any of them would believe his word when he said he was forced.
“Don’t be such a pussy, panty lover. I mean they are just some fun mementos of our fun time together as a couple, a first time getting pedicures together. There is no way I’m going to delete some good memories, besides they are for our eyes only, at least as long as you are a good sissy that is. Now quit bitching and get on with it, there are still several coats to finish and you still have a store to go to for some stockings before it closes. Trust me, you don’t want to potentially miss those.” Valeria ughed as she simply closed her phone and ignored his request.
Jake badly wanted to plead his case, but he knew it was a lost cause before he even started. In the end he just gave up and hung his head in defeat as he carried on with the first coat of polish on Valeria’s nails. While that was drying he followed Valeria’s instructions to apply a clear glossy protective coat to his own nails before turning back to hers. With his nails finished, there was nothing to do but wait for the polish to dry when he finished applying a second coat of polish to Valeria’s nails, or at least he wished there was nothing for him to do.
Valeria clearly had other ideas though, the moment he finished with that second coat she just fixed him with a wide grin and spread her legs even wider. She didn’t say anything at all, all she did was give him a wink. Then again that was all that was needed for Jake to know exactly what she was getting at. While Jake wanted to refuse, not wanting to be used like a mere sextoy again, he knew Valeria would just tell him what she wanted if he didn’t do it. It wasn’t like he could refuse her if it was an order. Besides just sitting here in front of her and waiting was nearly as awkward as occupying himself with eating her pussy so what was even the point of fighting it? He thought as he leaned forward and dove in yet again while his own cock struggled in its cage.
By the time Valeria had her orgasm, her nails were sufficiently dry to apply the final clear glossy protective coat to them. While Valeria could have let him go to the store now she decided to have one more orgasm before he left. It was just too tempting to pass up on, seeing him so completely obedient just did things with her she could hardly describe, it was too hot to put into words and like with every step she had taken to gain more control over him, she just wanted even more. This orgasm was just her basking in her victory because she could.
When she came yet again Valeria didn’t even bother to tell him to stop, or that he could go, she just pushed him back with her foot of which he had just painted the nails while she fell back on the bed completely satisfied. “Mmm that was amazing my sissy panty lover. You’ve been very good today so far, clearly you really needed that wakeup call. In any case, you still have a store to catch before it closes or all your work here will have been for nothing. I can assure you you will lose more points than you’ll gain if you fail to repce your stocking collection, and that would be a real pity as you’ve gained so many points today. If you had just given me those massages you might have even reached enough to earn yourself a well deserved orgasm. As it stands now though you don’t deserve orgasms yet, but who knows, the evening is only just beginning.” Valeria spoke up at the ceiling, not even bothering to look at him as she spoke.
“Oh and sissy, one more rule, since your nails are prettier now, and your panties are prettier, I think your stockings should get prettier as well. I don’t want you ever buying those mate nude ones I gave you as a first pair. Not even the shinier ones you bought next. You cover them up anyways so it isn’t like it matters much. If you want to buy nude ones they have to be sheer and really glossy, I don’t want to see more than two of the same pairs at once in your closet with the exception of what’s already there. All your stockings need to have ce tops, and tonight when I come over to update your score I want to see you wearing sheer white stockings. As always how many you buy is up to you, but you know my requirements. Good luck sissy, and unless you have any more questions, I’ll see you ter.” Valeria spoke casually, her voice still a bit breathy from her recent orgasm.
Jake was mortified, ce tops, prettier stockings? All that said to him were more obnoxious stockings, stockings that would be caught easier if there was an accidental slip. He couldn’t put up with this, he shouldn’t. Weren’t these frilly thongs embarrassing and obnoxious enough yet. “Miss with all due respect, but I feel really uncomfortable with that idea. I will repce my stockings, but I would really appreciate it if you reconsidered and let me buy stockings like the ones you gave me the first time.” Jake tried to desperately plead his case.
“I’m really not in the mood for a discussion about this Jake, either you do as I say, or you don’t and you face the consequences. It is that simple. Just know that my demands won’t change one bit so one of those consequences will be for you to go back to the store and do better. Now leave me alone while I bask in the after math of my orgasm, like I said. I’ll see you ter.” Valeria casually waved him off, still not bothering to get up so she could look at him, another way to make him feel extra vulnerable.
Although he had pretty much been expecting to hear a no, the sheer carelessness with which Valeria gave it to him bothered him to no end. It was so unfair that she shut down each and every one of his points without even considering them. It made him feel so intensely helpless, but it was crystal clear to him that trying to discus it would only work to annoy Valeria which might have consequences of its own. On top of that he was running out of time as well. He doubted Valeria would ever yield on the fact that he needed to have backup stockings even if he could convince her about what kind he was allowed to buy. As it stood now he could still make it to the store deeper in town, but if he wasted a lot more time he would be stuck going to the on campus store and that would be a down right disaster. The chances of not being seen by someone he knew there were pretty slim and given what he had to buy no matter the style of stockings that would be a disaster.
With a deep sigh Jake gave up and headed to the bathroom to quickly wash Valeria’s juices off of his face before getting dressed and leaving, luckily without stockings, although he knew that wouldn’t be for long. Besides the frilly thong was still bugging him plenty. Out of the door Jake strongly considered just refusing to go and buy those stockings like Valeria had cimed he could. Her vague warnings about the consequences bugged him to no end though and so instead of going to his dorm he started heading down to the store in town. He still hadn’t made up his mind about what he was going to do, but he guessed he could at least get himself a little more time to think while keeping his options open. Not going now would mean having to go to the on campus store or face the consequences of disobedience whatever those might be. Given the consequences he had faced up until now those were certainly to be avoided.
The entire road to the store Jake was preoccupied seriously weighing his options. He really didn’t want to take this another step further, but he wasn’t sure he could deal with the consequences either. He wanted to put up a fight so badly, but he was scared, scared of what Valeria would come up with if he did. The more he thought about it the more he felt the desperation set in. What did he even stand to gain if he didn’t buy those stupid stockings? As far as he was aware, a brief good feeling that he had resisted Valeria was all. She had made it very clear that the consequences that would follow wouldn’t change her demands. In other words if he didn’t buy these stockings now he would have to do so tomorrow or face more consequences. While he could deal with another spanking and losing those points he didn’t care about just yet, he couldn’t deal with Valeria revealing his secret which he feared would be an inevitable consequence down the line if he kept on refusing. He knew he couldn’t let things get that far. One thing was for sure, he wasn’t going to buy the nude ones like st time, or the mate nude ones as those wouldn’t do anyways. The choice was whether he would buy the stocking Valeria demanded, or not buy any at all.
By the time the bus finally arrived at the store Jake had reluctantly made up his mind to go ahead and buy some stocking. No matter which ones he wore no one but Valeria would ever get to see them, he wouldn’t even run the risk of showing off those mate nude ones, so what did it matter anyways? He thought, more out of a necessity for him to try and rationalise giving in to Valeria yet again rather than actually believing it. It was the best he could think of doing to make it all at least a little more bearable.
Heading into the store at this time right when everyone got off work it was extremely crowded. It almost made him want to change his mind again, but what point would it serve? He thought all his rationalising having some effect. He had convinced himself that he really didn’t have a choice here and so he walked in, straight to the women’s lingerie aisle where the hosiery was. No guy should know the way to that aisle so well, but in this store it was about the only aisle he knew. After his stressful trip st time he simply couldn’t forget where it was.
At least the lingerie aisle was one of the emptier ones in the store. After all people didn’t need underwear as often as they needed food and no one shopped here looking for a specific set to entice anyone. It was mainly used to pick up some simple every day wear underwear with people picking out their specific brand without looking too much. Jake wanted nothing more than to just snatch a package and run as there were still too many people around even here, but he couldn’t afford to do so, not with Valeria’s added instructions. He had to look for ce tops and white stockings at the least. No simple task in front of the wall full of nylons he was faced with.
Although he was the only one in the aisle who didn’t want to be here, the only one in a hurry to get out of here he inevitably ended up being the one to linger longest. It got him some odd and even some judgemental looks, but luckily no one said anything as he gathered two sets of stockings that fit what Valeria demanded. Then two more, and so on until he found the white ones he had to have of which he also took two before dashing to the register with an arm full of stockings. Just in time it seemed as he saw a rather pretty girl in a store uniform head straight for him, probably to ask if he needed help with how badly he was searching. From the slight amused look on her face, it was clear she was also heading over to poke some fun rather than just helping out. Luckily he dodged that bullet he thought.
With how fragile these stockings were and how he couldn’t see an end to this whole ordeal yet, he figured he might as well grab a lot of spares now that he was here anyways. After all the st thing he wanted was to have to come back here any time soon, and he had a feeling that ruining another pair would happen rather soon. It was inevitable. Looking down into his arms he hadn’t quite pnned on taking so many stockings, but there was no way he would return to put them back. Instead he made his way towards the register getting more strange looks when people caught a glimpse of what he was pnning to purchase. Although that may also have stemmed from the way he was awkwardly trying to hide the many stocking packages.
When he finally got to the registers there were lines at all of them, and while he wanted to get out of here as soon as possible he did opted for a longer line simply because he noticed the cashier ringing up the shortest line was the one that had rung him up st time. He couldn’t help but fear that if he went there she would make some comments about his purchase given how she had lightly teased him st time. He really wanted to avoid that woman at all costs, although he came to doubt if he shouldn’t have gone for her line anyways. After all standing in line was killing him. With nothing else to do but wait a lot of people simply looked around and he definitely caught there attention. There were looks of shock, looks of amusement, and he could swear that there were two women gossiping about him. The line couldn’t go fast enough as Jake was concerned.
It was almost a relief when he finally got to put his stockings down in front of a somewhat tacky cashier in her te twenties. She simply couldn’t stifle a giggle as she ran package after package under the scanner. Two pairs of sheer bck stockings, two pairs in dark grey, two in sun tan, two in dark blue and finally his white stockings which didn’t seem to scan. Much to his horror the cashier cried out in front of her. “Hey Sonja! The sheer white hold ups stockings with ce tops for this handsome d over here don’t seem to scan, do you perhaps know the code?!” It was way too loud and Jake was certain everyone at all the registers had heard. He just wanted the ground to open up and swallow him whole as shocked gasps and giggles alike erupted around him.
Just as he thought things couldn’t get worse, the woman two register’s down turned around, the same middle aged woman from st time who was apparently called Sonja. “Oh it’s you again sweetie, back for more? Those white ones will be a lot prettier than your st purchase. The code is 781678982.” Sonja spoke with a big smirk, happy for the fun distraction in her otherwise boring day.
Jake was absolutely horrified though, not only did everyone hear he was buying stockings, now they also knew it was the second time, but with most of his purchase rung up there was no running now as he tried to hide instead. Not that it was possible at the registers. When the cashier now ringing up his purchases finally managed to ring up this st pair as well with the code, Jake paid by card straight away, then rushed out of that store as fast as his legs could carry him leaving the giggling and the gossiping far behind him.
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