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Chapter 30
The remainder of the day had pretty much followed the same pattern. He wasn’t really able to participate in a lot of the conversations as he was slowly getting out of the loop. Then again speaking up meant dragging attention to himself and as self conscious as he was he was happy to avoid that. At least the subject of his retionship didn’t come up all that often any more either after his sheer refusal to give any more details. When it did come up, it was subject to snickering and some jokes, but all in all they were running out. The novelty of it was wavering a little.
For Valeria on the other hand things were not getting old one bit. She still loved taking every opportunity to drive home his embarrassment as much as she could. Even acting slutry around him and teasing him was fun as it never failed to make him struggle with his cage making him more desperate to please her, further breaking down what pride Jake had to make him even easier to control. She had loved pushing him down to his knees again in the bathroom at lunch to get her off to a sneaky orgasm and she had loved commenting on how soft his hair was during it as she ran her fingers through it during the process. Complimenting him on being a good sissy for using her conditioner like she had asked. The evening was once again spent with a movie and plenty of orgasms for Valeria while he remained denied.
Their matchday on Saturday provided another huge blow to Jake’s standing. While they won, they only won barely and that against the absolute worst team in their competition leaving none of them to feel good about it at all. A lot of it had been due to mistakes Jake had made. It had been so bad that the coach had even benched him near the end of the match after which the team had pyed significantly better. With Jake having shown up fully dressed again and with him leaving to get showered and changed at home, none of his teammates had hold back on venting their frustration with how he had nearly screwed them. They wouldn’t have been nearly as harsh if he had been present, but with his performance paired with the fact that he wasn’t even there before or after the match their frustration with him grew. It had been kind of funny at practice, but now that they were all kind of frustrated it was anything but funny to them.
Jake himself felt awful about it. He had never been benched before yet his performance had definitely warranted it and that while he used to pride himself on being the best pyer. He hadn’t liked abandoning his teammates straight after that embarrassing match either, but it was the least worst option to him. Sure they might be mad at him, but it was better than the alternative of them finding out about his painted nails and chastity cage. He just hoped he could make this all right once Valeria granted him some more freedom again, but he knew he would have to earn that which is why he didn’t protest any of her demands to spend time together after the match, giving her plenty of orgasms to celebrate the girls team victory while he would have much rather just spent time alone getting over his shame of failing the team.
Despite the fact that he now had to earn more points to get some relief himself Jake stuck with doing the absolute minimum, nowhere near desperate enough to humiliate himself just to earn a humiliating orgasm. He did oblige with all of Valeria’s rules and demands though not wanting to screw up and lose unnecessary points either, besides he had been putting up with those for a while now and they hadn’t really changed so it wasn’t too hard. At least Valeria didn’t give him any trouble for it, not until he finally did earn his orgasm on Sunday te at night. By that time Jake had really started to need his orgasm, but it simply coincided with getting there doing the bare minimum. Displeased by the ck of initiative he had once again shown Valeria had however pulled up the points he needed for a next orgasm to a whopping fifty.
It made Jake realise that despite his reluctance to work for a next shameful orgasm he would need to do so. Having felt the sexual frustration rise already there was no way he would make it to fifty doing the bare minimum without getting horny out of his mind. Besides that wasn’t the only issue. With that tactic. There was no telling what number Valeria would raise the bar to if he refused to take initiative once again. It was a chance he simply couldn’t take and so from that point forward Jake picked out at least one thing on Valeria’s embarrassing list each and every day, stepping it up after a day or three when the sexual frustration was starting to rise. It took him five days to get to his next embarrassing orgasm while his retionship with his friends was a little strained, especially since he had continued to refuse to get changed with them or go to parties with them for that matter. On Saturday it took another hit when he once again pyed less than stelr, his chastity cage wasn’t helping either.
As the days dragged on Jake’s constant focus on working off of the list Valeria had given him to score points paired with her frequent demands and the fact that his retionship with his friends was further deteriorating was doing a huge number on what remained of his confidence. He had hoped that Valeria would grow more lenient, that their retionship would move on from embarrassing hand jobs, but as he worked hard since his st orgasm Friday night, earning himself another one on Monday after basically doing every chore on the list he could do only to be rewarded by another shameful handjob, Jake realised that Valeria wasn’t inclined to change the status quo, seemingly happy with how the things were going.
He realised then and there that Valeria wasn’t going to take initiative to change the status quo so with that in mind in mind he decided to speak up himself once Valeria finally got off of his face. The weeks of chastity and getting used to living underneath Valeria’s thumb had done a real number on him. The fact that he was currently dealing with his post orgasm shame, another puddle of cum ying on his stomach was giving him some motivation to try and improve his situation, but it wasn’t helping his confidence at all. “Miss Valeria, thank you for pying with my sissy clitty and helping me make cummies.” He spoke utterly embarrassed, but knowing he should thank her because she had demanded it before.
With that out of the way he carried on. “I couldn’t help but wonder if we could maybe talk about stepping up our retionship from hand jobs Miss Valeria. You told me we might have to talk about it if I kept being this good a while ago now. I’ve tried my hardest to be very good so I was wondering if maybe we could have real sex, or maybe a blowjob if that’s still too much. I was also wondering if maybe I could go back to being released from chastity and wearing my white panties before practices and matches. I promise I will never refuse to be put back in my cage.” Jake spoke rather shyly, really hoping to make his orgasms less embarrassing and to be able to regain a sense of normality so he could start fixing things with his friends rather than letting them deteriorate even further.
Valeria for her part was thrilled to finally be having this conversation. She had loved her time with Jake so far and she was in no hurry at all, pleased with how obedient and servile he had become. It had been a long process already, but by now he was a far cry removed from the arrogant womaniser he once was to the point where she doubted he could just go back to his old self. She had basically maniputed him down into a completely different person and she loved it. Her morals regarding Jake had definitely gotten watered down. Where she had started out with the idea of getting some justice, there was no denying anymore that she did what she did simply because she loved it too much by now. All she saw in his question was a new opportunity to step up her control once again. She could have forced it through earlier, she was sure of that, but this was way easier.
“You are right babe, you have been an amazing sissy these past two weeks. I don’t think we are anywhere near ready for real sex just yet, but maybe your next orgasm could be from a blowjob if you are very good. As for your request to go back to just your white panties on match and practice days, I’m afraid I can’t quite trust you yet. I mean you have been doing everything to try and find loopholes in my very reasonable preventative measures like wearing sock and boxers over your stockings and panties. Unless you get rid of those I’m afraid I can’t even begin to go about trusting you. If you want to earn your first step towards earning my trust you can start right away.” Valeria spoke firmly as she helped Jake out of his cuffs only to walk off to a nearby kitchen drawer and return with a pair of scissors she held out for him with a big smirk.
Jake couldn’t help but feel shocked as he took the scissors, Valeria’s intentions being very clear as she watched him amused with her arms crossed over her chest. For a brief moment Jake had started to get his hopes up when Valeria had agreed with the first part of his question, but her mention of trust and what it would take to earn it had instantly crushed that hope. He couldn’t actually go cutting up all his underwear could he? While wearing lingerie for what seemed like forever to him now without getting caught he had started feeling a little less nervous being outside, but the thought of never being able to fully cover his lingerie made him more nervous than ever. Especially since he had burned through pretty much all of his nude coloured stockings, the mat ones first, but also most the slightly shinier ones. They were the least obvious stockings he owned and thus the ones he had worn every chance he got. The cheap stockings didn’t exactly hold up great through multiple wears and washes making them fall out one by one. He only had one pair of the slightly glossy nude coloured nylons left. After his big purchase he still had plenty of stockings to meet the needed five pairs, but they were all way more obvious and thus scary to wear. He dreaded the idea of buying more stockings, and it wasn’t like that was going to solve anything anyways as he was forbidden from buying more of the subtler ones.
It brought him to a to him very tough dilemma. His dread for what this would mean was strong enough to break through the near instinct to follow Valeria’s demands and suggestions that had slowly developed within him. He really didn’t like the idea of risking exposure like that, but at the same time he already new Valeria wouldn’t back track on her demand. If he ever wanted her to trust him enough to finally get out of that cage for soccer and maybe build on that to get out of it permanently then this was a step he would have to take. If not now, he would have to do it in the future, or possibly accept that he wouldn’t be getting out of that cage unless he was securely tied to the bed every time.
After a few long moments of contemption Jake decided it was best to just bite the bullet and get this over with. He tried to tell himself that his frilly thongs didn’t rise high enough to peek above the waistband of his pants and that no one would notice the small peeks that might happen around his ankles. They were under a desk when he was sitting down anyways so pretty well hidden right? The truth was that he felt anything but certain about that he just needed to hold off on the thoughts of what might happen long enough not to panic and get this over with. The fact remained that this was very much necessary as he really wanted to be allowed out of this cage eventually even more than he wanted to earn himself blowjob privileges rather than those embarrassing hand jobs. He wanted to recim his life more than ever, but after spending so much time underneath Valeria’s thumb, his fear of her was bordering on irrational. She had constantly managed to keep him in line through threats and chastity up until now, so long that he had started becoming afraid of the consequences of not doing what she said even without really thinking about those consequences. It was slowly morphing into a reflex to obey.
Reluctantly Jake got up off the bed to quickly clean his stomach with a tissue before approaching his underwear drawers with the scissors and plenty of nerves. He couldn’t believe he was actually doing this, but he needed to, things might be a little harder now, but it was a sacrifice he needed to make for them to get better. Besides he guessed he could always buy new boxers and socks it was a waste, but it wasn’t like he was saying goodbye to boxers and socks forever right? Jake thought as he motivated himself to get this done.
Despite all his attempts to rationalise it and motivate himself, picking up that first pair of boxershorts and running his scissors through it remained incredibly hard. Just the sound of cutting through fabric was nearly physically painful and as the pair finally fell in half, utterly ruined Jake’s heart skipped a beat. He couldn’t believe he had just done this, it was even harder than he had imagined and while he vowed it was only temporary, it still felt like he was cutting up his manhood. The second pair wasn’t any easier, and neither was the third, or the fourth,…
Pair after pair Jake cut up his socks and his boxers into a pile of useless cloth that was quickly growing in front of him. Meanwhile his underwear drawers were looking emptier and emptier much to his dismay. Worse than the empty look however was the fact that his panties and stockings were getting more and more obvious in the drawers as they started slowly dominating the contents. Up until now Jake had always hidden those under his normal underwear but that cover was also quickly disappearing until finally it was completely gone. With a loud groan he realised he really didn’t have any regur underwear left anymore, all his drawers now housed was a mass of sheer nylons and colourful satin, just he way he would look if his pants got pulled down. Hell even just if they lowered a little or the legs rose too high. Looking at the pile of useless cloth Jake couldn’t help but feel a pang of regret. Now that the deed was done he couldn’t help but wonder if it wouldn’t have been best to just deal with his chastity.
As he sat there mourning the loss of whatever masculine underwear he still owned Valeria quickly knelt down and hugged him from behind. “Awww, you did great babe. I know first steps are hard, but I’m very proud of you.” She said only to pnt a kiss at the side of his cheeks after leaning over his shoulder. Although she was hard on him to push him further and further into becoming a submissive sissy, Valeria had also warmed up to him significantly. Her ploy to be his girlfriend might have been one to punish him for his big mouth while making him regret it, but by now she had really warmed up to the idea. She might love embarrassing him, but having him so helpless and vulnerable in her arms also made her feel warm and fuzzy inside. A lot of her hugs were genuinely affectionate rather than the rolepying they had once been.
“Now why don’t you go clean that up and get back in bed with me so we can watch a movie?” Valeria said when she eventually broke the hug after a minute or two. Although Jake was barely over the shock of what he had just done, he quickly complied, happy to shut the drawers holding the evidence of his actions. Throwing away all the scraps of his old underwear was nearly as hard as cutting it had been, but then again, nothing he threw away was salvageable anymore anyways. He had made sure of that with he scissors.
Done with his task he returned to his bed where Valeria was already propped up against the head board of his bed, holding his pink satin sheets up as an invite as she y there with her stocking cd legs wide open. Like a lot of nights these past two weeks Jake sat down between Valeria’s legs, leaning up against her torso, his head resting on her chest. Although being around Valeria often made him nervous, especially when she was making demands, Jake had to admit these moments were nice. With his retionship with his friends somewhat strained and no new girl to spend the night with each and every day, he had been feeling increasingly insecure and a little touch starved. It might be embarrassing to feel his cock react in its cage, to Valeria mindlessly pying with his nipples once he took pce, or to the sensations of her nylons brushing against his while the satin sheets slid over his entire body, but it did make him feel cared for and safe in a strange way. Their night ended like every night where Valeria was up for a movie. A quick movie, followed by a bedtime orgasm for Valeria and ending with Jake taking on the little spoon position as they went to sleep.
Chapter 31
After what was a rather restless night for Jake, worrying about his first day without anything other than his pants to cover his stockings and thong, he got woken up by his arm which he quickly shut off. Without even needing to be told this time he slid under the sheets and brought a moaning Valeria who was slowly stirring awake to a morning orgasm. She always seemed to be in the mood for one, and after having spent multiple mornings with her he had gotten into a kind of routine of what she liked, trying hard to be good for her. Having given her an orgasm he quickly got out of bed and cooked the both of them a small breakfast while Valeria slowly came down from her orgasmic high to the aromatic scent of the coffee he was brewing. It made her feel like a queen and she loved it. She wasn’t the biggest morning person so waking up so slow and nice, not having to take care of anything was great.
While Valeria just slowly enjoyed her meal Jake ended up hurrying a little more himself just so he could rush out to run the shower for them so it would be warm when Valeria arrived just a few moments ter. In the shower they proceeded to wash each other using Valeria’s products, something which occurred way too often for Jake’s liking as it always left him smelling so much stronger of flowers than just the conditioner did. His friends hardly bothered to point it out or ask about it anymore, and it definitely was the st of his worries today. With their shower coming to an end Jake was feeling his heart sink in his chest as the moment he would need to head out with his stockings and thong way too exposed for his liking was drawing ever closer.
Jake was gd that this time Valeria didn’t insist on a specific pair of stockings or panties for him to wear, but then again that was only a very slight relief. The nude nylons with the slight shine to them he chose might kind of pass as just a bare ankle at first gnce, but knowing about it he could only see how painfully obvious it looked to him. It did nothing to hide the soft pink polish his and Valeria’s toenails now sported either, then again those would luckily be in his shoes. Choosing a baby blue rather frilly satin thong didn’t help one bit either. There simply was no thong avaible that wasn’t completely obnoxious each and everyone of the colours was too bright for his comfort and none were even remotely able to be confused with any colour a pair of boxershorts might have.
Putting on a pair of pants with the longest legs and the highest waist he could find in his closet he couldn’t help but be surprised by how alien they felt. Without his boxers it nearly felt like he was going commando. No part of the thong was covering his butt cheeks leaving the denim of his jeans to rub straight over the smooth globes. It was mortifying, a firm reminder of just what he was wearing, or rather what he wasn’t wearing. Just as he was growing a little used to the sensations of his dainty lingerie, no longer worrying about it quite as much anymore, the worry was right back in full swing. Simir to the pants his shoes also felt rather strange, like they were a little bit too rge. The nylons were significantly thinner than any pair of socks he had ever worn with shoes before, and the slipperiness of the material caused his feet to slide a little inside of them.
His clothes felt completely off and while that served as a permanent reminder of this shameful and frightening predicament, it was the least of his worries. After he finished getting dressed Jake couldn’t help but test out some positions to see just how obvious his lingerie was. Standing straight everything was pretty much fine, not a hint of either his stockings or panties were on dispy, but as he walked back and forth a little he swore he could spot to occasional fsh of a stocking cd ankle. It was mortifying, but it got even worse as he took a nearby chair and sat down, a subtle glimpse of his nylon cd legs becoming painfully visible. It wasn’t enough to be instantly obvious, but definitely enough to be visible which was absolutely terrifying all getting caught with his secret would need was someone thinking the bit of skin looked odd before figuring out why it looked odd.
That wasn’t the only problem though, leaning forward caused a glimpse of the baby blue ruffled satin decorating the top of his thong to be visible at the back of his pants telling him he better made sure to sit absolutely straight. When he eventually decided to bend over as if he was picking something up it became even more obvious. Trying to lower himself through his knees instead to prevent having to bend over, revealed way too much of his stockings. No matter how he tried, if he needed to pick something up he would have to choose which part of lingerie he wanted to risk exposing. A problem simir to pulling his pants up a little higher to conceal his thong better only to reveal more stocking. No matter what he tried, without socks and boxers, there was no way for him to completely hide his lingerie making him regret st night’s decision to cut up his underwear even more.
“I have to say babe, that is some odd morning yoga you’re getting up to. In any case I’m afraid we really need to go now, we don’t want to be te now do we?” Valeria chuckled looking great as ever herself, wearing a cute skater skirt and what Jake was certain to be stockings rather than pantyhose. Ever since she had made him go down on her in the school’s bathrooms she had made that switch so she could demand oral whenever the desire struck her. Jake had always been a fan of nice flowy skirts, thinking them to be cute and sexy, yet whenever Valeria wore one he could only think of how easy it would be to force his head under there giving him very mixed feelings as it still looked amazing, troubling his caged cock.
Without leaving Jake much of a choice at all Valeria grabbed his hand and pulled him out, like nearly every morning. Although today it took a little more effort to actually pull him along with Jake shamefully trying to fight her pull. In the end he did end up yielding rather easily. After all he knew full well that he needed to head out as well and there was nothing left to salvage his predicament, he had made sure of that himself with those scissors st night. As Jake walked around campus at Valeria’s hand, he was feeling more nervous than ever before in his life. Walking around only made him even more aware of how different his clothes felt which in turn made him feel like everyone knew exactly what he was wearing. If anything his own strange behaviour was the biggest tell that something had changed in the first pce.
As they walked across campus, they ended up getting a few odd looks only fuelling Jake’s nerves It was impossible for him to tell whether they came from the way he was behaving or from someone who had noticed a glimpse of his lingerie. It was devastating, only a few people needed to figure it out for his secret to start entering gossip around campus. He couldn’t have that, but aside from hoping for the best there was no way to really prevent it. Not any more that was, his only shield was down in rags in the trash.
When they rapidly approached Jake’s first css of the day panic was really starting to set in. Entering the gossip of retive strangers was scary, especially because he wasn’t exactly a low profile here at college, but it wasn’t nearly as scary as one of his friends noticing. His panic was so overwhelming that he couldn’t help but dig in his heels as they approached the css. “Uhm Miss Valeria, why don’t we say goodbye here? I really need to use the bathroom before heading to css and I wouldn’t want to waste your time.” Jake expined nervously, hoping that his Mistress as he was really starting to think of her would agree.
Valeria gave him a slightly quizzical look, but she ended up quickly agreeing. After pulling him in for a quick passionate kiss on her terms like they often greeted and said goodbye, Valeria spoke up. “Alright babe, have a good day, I love you! And rex, you shouldn’t be this tense just because you love your delicates. I love it about you and I’m very gd you’ve decided to embrace it more.” Valeria spoke, conveniently leaving out how she had basically made him embrace it. She really wanted Jake to feel like he was an actual sissy rather than that she had forced him into everything. Besides she was genuinely loving this new him more than she had been able to imagine ever loving Jake. While she did wonder why Jake suddenly made an excuse to part ways already, she didn’t interfere, it wasn’t like there were many options for him aside from powering through it anyways as she quickly went on her way to her own css.
Jake for his part felt more than a bit relieved to see Valeria going. He really wanted to approach his friends on his own terms now that they may potentially spot his lingerie. He wanted to do so as te and as inconspicuous as humanly possible, but as the few minutes until css ticked by and his nerves heightened he wasn’t even sure if he wanted to be around his friends at all. The more he thought about it, in part to his ever rising nerves, the more he couldn’t help but feel that it could only spell trouble.
After all they had very little left to talk about, he was never at any of the parties unless Valeria explicitly demanded it. His date life was something he constantly blocked off discussing with his friends and they had long since stopped asking about it. It had left them with pretty much just sports to talk about but as that usually ended at soccer and their games it was another subject Jake liked to avoid as it put further strain on the retionship with his friends regarding his bad and anti social performances. It usually turned into a berating that he really needed to step up his game. He really tried to at least earn that respect, but with his mind preoccupied with so many things and secrets it was incredibly hard to keep his head in the game.
By the time it was time to head into css Jake’s nerves had gotten the better of him and he had chosen to avoid his friends all together, sneaking into the room and sitting somewhere at the quietest corner of the room he could find, as far from anyone who might notice a piece of his lingerie as possible. It felt awful to isote himself like that, but not as awful as the stress of someone discovering his secret. This was the best thing he could think of doing. Besides having nothing to really talk about he felt rather isoted hanging with his friends anyways. This was most definitely for the best.
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