Chapter 21

 

It was around 3 a.m. Jake had been fast asleep for quite some time now when Valeria was on her way home from her celebration. Not that any of her friends knew exactly what she was celebrating. Some had heard from their boyfriends that she and Jake had broken up and that Jake had seemed pretty happy and rude about it having called for a celebration. They were ready to consolidate her, telling her that they were sorry and that that asshole would never change no matter how much it had seemed like it. That it was probably all just an act for him. They were incredibly surprised however when Valeria hadn’t seemed bothered by it at all, telling them they had talked it over and that Jake wouldn’t be ditching her, that if anyone would do the ditching it would be her. Her friends couldn’t help but think that Valeria was a little naïve to think so, but they figured everyone had their way of coping with things so they didn’t bother pointing out that whatever she had promised Jake to extend their relationship probably wouldn’t last. It was not worth upsetting her about so they just all had a fun night together, little did they knew the kind of hard guarantees Valeria had, literally, hard as in steel, like his cage.

 

Valeria’s friends weren’t the only ones who were surprised to see her however. Some of Jake’s friends had also been at the club, having gone out to pick up some chicks alone now that Jake had cancelled on them. They couldn’t help but wonder where the hell Jake was if Valeria was here, didn’t he cancel because the make up sex was so fantastic? This just didn’t make sense? Or had he picked up another chick in the meantime after make up sex with Valeria? Knowing him it wasn’t implausible. They kind of blew up his phone, but there was no response to be had from Jake at all.

 

On her way back from such a fun night Valeria wasn’t ready to just go to bed yet though. She was a little tipsy, and incredibly horny having constantly thought about how Jake must have been laying in bed, frustrated and denied, thinking about the control she had over him. Surely he was thinking about it, she sure was and it didn’t fail to get her all fired up. It might be very late and being stuck alone in his dorm she guessed he was she doubted he was still awake, but she was more than in the mood for another orgasm and given how she had a key, she guessed she could demand some surprise oral at least oral for her performed by him if she wished. It wasn’t like Jake could deny her, hell with her own key he couldn’t even act as if he wouldn’t hear her knock she could let herself in. So with a huge smirk and a tingle of sheer anticipation Valeria made a detour to Jake’s dorm rather than going to her own.

 

She couldn’t help but feel so very naughty and excited, sneaking through the dorm building so late at night with the purpose of some sexy fun times. She could barely contain a giggle, it was just so awesome to be doing this. Surely her boldness had been fuelled a little by her tipsiness, but that hardly took away from the fun at all. Right as the approached Jake’s door she slid out of her heels, continuing on her stocking clad feet as she really wanted this to be a surprise. She was very careful not to make any noise as she opened his door and slid into the dark room, getting out of her dress, panties and bra the moment the door softly closed behind her. Luckily the layouts of the dorm rooms were pretty much the same as she managed to blindly navigate her way to the bed in the dark. It was only there that she turned on the light, and instantly hopped onto the bed, planting a stocking clad knee at both sides of Jake’s head only to promptly sit down, her sopping wet pussy over his mouth, and his nose buried between her cheeks as she sat facing his body. Valeria couldn’t help but let out a laugh and a moan as the startled guy jumped awake, squirming a little underneath her oh so worked up pussy.

 

Jake was downright shocked, getting woken up so roughly in the middle of a very deep sleep. His first instinct to get up was completely mitigated by the heavy weight on his face as he needed a few moments to realise where he was and what was happening. The scent of Valeria’s pussy was strong, especially mixed with a slightly sweaty odour from her night of partying. He couldn’t believe she had really just snuck in here and sat down on his face, but at the moment that was his exact reality as he finally calmed down a little now at least knowing what he was dealing with. He didn’t like it, especially not as Valeria’s scent drove his cock to a near painful attempted erection in the cage that would kept him orgasm free until he earned one according to Valeria’s horrid scoresheet.

 

Just thinking about that scoresheet made him aware of a whole new issue. He had neglected to put on those stupid white panties he was supposed to be wearing to sleep in now, something that would certainly put him in trouble if it was found out. Valeria hadn’t just left him alone like he had expected and with her now sitting on his face the risk of his small sign of protest being discovered was huge. He just hoped that she wouldn’t go looking under his sheets or he was done for. Figuring that she must have come here for an orgasm, and thinking she would leave the moment she got it Jake started licking her pussy with all he had without even needing to be told, the sooner she was gone the better his chance of getting away with this.

 

“Mmm, someone seems to be very eager to please me. What a good sissy you are. I like the initiative sissy, you shouldn’t be told to please me, then again I guess sitting on your face is demand enough isn’t it?” Valeria giggled through moans, loving how this was going way better than she had expected as she started grinding back and forth lightly, to meet his tongue. She had expected there to be more protests, or at least a longer time to get started for Jake, but she didn’t mind this course one bit. Clearly her visit earlier had left an impact as he was doing his best to be ready to please her literally whenever she felt like it give her very late surprise visit. This was perfect, an eager face for her to hop on at any time, just the direction she wanted for Jake, if only his friends or her girlfriends knew just how much in control of the relationship she was. She still couldn’t help but get a chuckle out of the thought that her friends assumed Jake could break up with her. She owned him and it drove her wild with lust. They were right about one thing though, the asshole in him had never changed as it was back at the first chance he got.

 

Mounted high on Jake’s face driven wild with lust Valeria couldn’t help but want to keep her hands occupied as well. They quickly slid down under the sheets, her nails trailing along his skin, slightly digging in with pure lust as he at her out. She couldn’t help but giggle as she could tell he liked that, at least she figured that was what it must be given the muffled groans coming from underneath her. It was the tell tale sign she had come to expect from Jake’s cage growing a little too tight, and she was right as well, Jake had always loved some nails trailing his skin in the heat of the moment, it had always fired him up even more, but now that fire was quickly contained by that horrid cage. Worse than that even was the fact that it got him incredibly nervous. Especially when Valeria threw his covers back a little to see what she was doing, to see the red lines appear on his smooth skin, to expose his nipples which she couldn’t help but toy with a little, pinching them, pulling them a little, twisting them, gently rolling them between her fingers. It felt weird to Jake, sometimes a little painful, but often weirdly pleasant, a pleasantness that only brought him further shame. He wasn’t supposed to enjoy having his nipples played with and he wanted it to stop. Not that he could communicate that and even if he could he doubted Valeria would listen.

 

The only way out he could think of was giving Valeria that orgasm as he ate her pussy with renewed vigour. It was a sign Valeria completely misinterpreted as she laughed from high above him. “Oh my, it looks like someone really loves getting their nipples played with. You really are a sissy aren’t you Jake? Let me tell you a secret though, I also quite love having my nipples played with, maybe one of these days you’ll even get the chance to play with them. In any case, I didn’t think a guy would like something like this, then again I guess you’re not really a guy are you sissy? Let’s have a look at your clitty shall we? I wonder if it is already leaking in anticipation and frustration.” Valeria chuckled, she guessed nipples were a sensitive part for everyone, but she so loved shaming Jake for just about anything whether it was actually shameful or not.

 

As much as Valeria’s words stung to his pride, it was fear that got the upper hand, fear of what Valeria had said about his cock which she called a clitty. One look further down would reveal he had lied to her, but at this point that seemed to be pretty much inevitable. He just hoped that he wouldn’t be in too much trouble over it, that Valeria would be too tipsy and tired, enjoying his tongue too much for her to care. He feared it was an idle hope, but he still had to hope as Valeria started pushing his cover further and further down, firing up his nerves even more than before.

 

When the covers finally got thrown off of his caged cock, revealing the fact that he hadn’t worn his panties to bed his heart skipped a beat. “Uh oh, looks like someone has been a very naughty sissy, defying my rules after I have spelled them out mere hours ago. Panty loving sissies like you should never be without panties unless you’re taking a bath or shower, or you are using the toilet. Otherwise there are no excuses. Well I guess that means you’ve just earned yourself your first negative points. I really hope for your sake that you aren’t too frustrated yet cause at this rate your next orgasm is still a long long way off.” Valeria giggled, too tipsy and excited to actually be mad. If anything she was happy to have found a reason to subtract some points from Jake’s score as she quickly leaned over and changed the plus up front to a minus only to change the one read on his counter to a four. She wondered how long it would take Jake to grow frustrated enough to really try and earn his way to an orgasm, and even better, how much points he would need to collect by them, she doubted this was going to be the last time he would try to secretly defy her.

 

Still laying underneath Valeria Jake actually felt kind of relieved. She didn’t seem mad, she didn’t threaten to expose him or anything, she just took a few of those points away from him which was literally the last of his worries. Sure he would like an orgasm, and he was kind of used to orgasms on a daily basis so going without wasn’t nice, but given the kind of orgasms she gave him he was in no hurry to get one any time soon, not yet at least, especially when he needed to do so many embarrassing things to even earn one. Feeling a lot less nervous already Jake dutifully, continued licking Valeria’s pussy, a lot calmer by now though as he wasn’t in a huge hurry to get her off anymore. Still he knew better than to slack now or he might get himself in real trouble and with her sitting on his face he had no leverage at all.

 

Luckily it didn’t take Valeria all that long there after to tip over the edge, her pussy pulsing over his mouth, forcing him to swallow a mouthful of her juices only for her to get started on a long nice after grind. At least nice to her as Jake could only groan a little having his face used as a toy like that, squashed under Valeria’s weight as she happily ground away. Any part of his face that had remained dry up until now got coated rather quickly as well. Jake’s thoughts couldn’t help but roam to the idea of how well and truly pussy whipped he was right now, as close to the literal sense as one could get. He already dreaded to think of how Valeria would abuse her power at school. He was going to have a hard enough time explaining getting back with Valeria as it was, especially after how she had been treating him up until now. The argument of just how great the sex was, was near exhausted. It wouldn’t be long until his friends considered him truly pussy whipped, but then again, that was better than the alternative. Of being seen as a sissy and all the dreadful assumptions that would come along with that.

 

When Valeria’s after grind finally halted after a few long minutes, she spoke up. “Mmm, that was great princess panty lover. You’ve definitely earned yourself a point for that one which leaves only three points to go for you to reach zero again. Isn’t that great. At least you aren’t in the danger zone of getting a real punishment on a potential next small disobedience which counts for something right? And as you know, if you want to earn that orgasm, there’s a lot more points left for you to score so I suggest you really start looking into that score sheet I gave you, if orgasms are at all important to you that is, I don’t really care as long as I have mine, and that key does look great on my ankle, I’m in no hurry to take it off even for a little while, it’s such a hassle after all.” Valeria mused before leaning over and pushing another button on the scoreboard to change the count to minus three.

 

Only then did Valeria finally slide off of his face only to turn off the light and slide under the covers right behind him. “I know I should be kicking you out of bed right now to put on your pyjama panties, but I guess I can allow it just this once, after all I’m not wearing panties either and I really want to catch some sleep right now. After all it is way too late already and I need to be fresh for classes tomorrow, that and I should rise early, after all I can’t go to class wearing my dress from the clubs now can I? It’s way too sexy and it reeks.” Valeria whispered into his ear from behind as she threw an arms over his chest to absentmindedly toy with one of his nipples while her perky breast pressed into his back and her warm wet pussy into the smooth globes that formed Jake’s firm muscular ass as he was once again forced to be the little spoon.

 

It wouldn’t be an issue if she hadn’t so truly degraded him before, or if his cock could grow hard. All it did now was further establish his submissive role to her while tormenting his cock. For as much as Valeria had degraded him, feeling her hot body press into his still turned him on beyond believe, especially with the scent of her sex strong on every breath. It got him incredibly worked up, but the cage kept a tight lid on his cock, preventing it from growing with the pain and discomfort that came with that. He couldn’t even get up to go wash his face . All Jake could do was lay there and suffer through it as Valeria fell fast asleep. Already quite rested and with all the trouble Valeria’s presence brought along, he needed over an hour, an hour of pondering all that had happened to finally drift off to sleep again himself.

 

Chapter 22

 

The following morning Jake got roughly awoken by the noise of Valeria’s alarm. It was way too early for him to wake up already, but he guessed Valeria kind of had to with how she still needed to go back to her own dorm and get ready. The noise was one thing, but now that he woke up, his cock instantly went back to bothering him. The scent of Valeria’s pussy was still heavy on his face and her hot body still pressing into his back was not helping at all, it instantly put him back in the mood, just like it usually happened with his hook-ups, only now that mood was pretty much squashed by a lot of discomfort coming from that awfully restrictive cage.

 

Jake wasn’t the only one put in the mood by the close body contact and the scent of sex still heavy in the air though, it also had Valeria all worked up, but unlike Jake she had an easy way of dealing with this. “Mmm good morning babe. I’m a little horny, so please be a good sissy and help me out will you.” She softly mused, as she put some pressure on Jake’s shoulders to signal she wanted him to get under the covers and eat her out. She was still a bit sleep groggy, but growing all the hotter being able to demand oral from Jake who’s cock she had under lock first thing in the morning. She loved the control she had over him and while it was still early for her as well after such a long night she was glad she had put her alarm a little earlier than necessary even.

 

As much as Jake hated being used like this while having to deal with all that shame and denial himself, he didn’t put up a protest. All protesting could mean was more trouble, especially now that he stood to lose to very much with Valeria’s reveal of those devastating videos. He just let her push him down underneath the covers and in between her legs which she had spread wide to accommodate him. Her pussy was already sopping wet as he started eating her out to the best of his abilities, taking her to the edge as fast as he could while Valeria just moaned loudly, leaning back and just thoroughly enjoyed herself, absentmindedly massaging his scalp with her long nails. It felt good to him, but it didn’t even begin to make up for the shame and discomfort he was going through to pleasure her.

 

Valeria for her part was having the time of her life. Jake’s tongue was so much gentler, yet so more well aimed than any kind of sex toy she owned. Some of her girlfriends swore by their toys, but she was quite happy with just the toy between her legs for now. She was a huge fan of this gentler pleasure. It was impossible not to smile when thinking about all the fun things she had done to Jake and all the fun plans she still had for him while looking up at his ceiling and simply enjoying the pleasure his tongue gave her.

 

This really was the life and she had no intent of stopping here either, she only wanted to make things better and better, at least for her that was, she doubted Jake would agree that they were better, but then again she didn’t need him to agree to anything, she just needed him to do as she said and she had all the tools she needed to make sure of that. She was probably taking this way too far, this wasn’t right anymore, but then again she was having so much fun and given what Jake wanted to move back to doing she still justified how she was doing everyone a favour by handling Jake the way she did, at least this way he would stop going from girl to girl and breaking many hearts.

 

It didn’t take Valeria all that long to reach the orgasm she had been craving as she had been more than horny enough waking up. The moment she tipped over that edge Valeria’s whole body tensed up and the gentle massaging of his scalp turned to a firm grip on his hair as she pulled him in close to grind out the intense waves of her orgasm all over his face, leaving every inch of it covered in her juices once more. She firmly kept him there as she slowly but surely caught her breath, enjoying the pleasant aftermath of her orgasm for a good while before finally releasing his head only to throw off the covers and get up right away.

 

“Here we go panty lover, one more point for you, now be a good sissy and don’t let me catch you screwing up again. Oh and today I want to see you wear a pair of your more glossy stockings. You can count on it that I will be checking on you sissy so I guess I’ll see you in class, or at lunch then, bye.” Valeria gleefully spoke as she hit the scoreboard again changing the minus three to a minus two before putting her panties back on, followed by her dress and heels at the door only to step out and leave the shocked soccer captain behind reeking of pussy with less progress to an orgasm than he had had when she entered here late at night.

 

Not showered, dressed in last nights clothes which smelled a little, her hair messy, and having just had an orgasm, Valeria was a bit of a mess as she walked back to her dorm in the early hours of the morning. For the very first time Valeria knew what people meant by a walk of shame, she didn’t like this at all, but she guessed it was the price for the amazing night and morning she had had. She wasn’t planning on making this her last surprise or late night visit to Jake either, so she would definitely have to find a solution for this so she wouldn’t have to go on another walk of shame. All in all she didn’t have any regrets though as she thought about what she could do to solve this one issue.

 

While Valeria had a little bit of shame and a small issue to deal with Jake was left deeply embarrassed and with a lot more issues. His cock was uncomfortably restrained. His ego had taken a severe beating as he had literally been used as a sex toy. The fact that Valeria made such free use of that key she had pretty much just demanded was worrisome as well, but it wasn’t nearly as worrisome as having to wear lingerie to class again or even worse having to face his friends after his loud way too early celebration that had been quickly supressed by Valeria. He dreaded having to face them and explain how he didn’t end up breaking up with Valeria anyways, and even worse how he would explain things not having improved at all. Maybe his friends would have bought it if he had gotten Valeria to treat him with more respect while playing the supposed great sex card, making it seem like they had an awesome relationship going, but he had no illusions about that being the last thing Valeria planned on making happen. With the small taste of her new power trip he had already experienced he knew that if anything Valeria would just drive up the embarrassment by a lot. It would soon be impossible to explain why he was putting up with it all, he mournfully thought as he went to take a long shower, taking his time given he had plenty of it having been woken up so early.

 

At least the water had quickly washed away the scent of Valeria which hadn’t been too bad, but still a trigger to give his caged cock a world of trouble. The cold water he aimed at his cage at some point also helped to relieve the pressure his attempted erection was causing him. Taking down last evening’s lingerie and putting it back into his drawers before pulling out a pale blue pastel frilly thong and some stockings with a little too much shine in them for comfort. He could only shudder feeling the slippery soft satin travel up his smooth legs only to cup his caged cock and ride up between his ass cheeks as a permanent reminder to what he was wearing. It was awful, but impossible to pull it out.

 

As awful as those panties were, they weren’t nearly as dreadful as the stockings. He was constantly terrified of tearing them by accident as he smoothed them up his legs with the utmost care, the subtle shine and lace tops making his muscular legs look a lot daintier already. The material was just so very thin and fragile and the last thing he wanted was to go shopping for more of these, something he knew he had to do if he ruined one pair. Given how he would now have to wear them daily until he could find a way out of Valeria’s clutches which seemed further off than ever before. Ruining a pair sooner or later seemed pretty much an inevitability at this point, which didn’t mean he wouldn’t try to delay it as much as possible. Aside from being dreadful to handle, afraid to cause damage they were also dreadful to wear. These shinier nylons were definitely visible and he already dreaded wearing them to school for the first time, if someone would catch a glimpse of them he was done for. Aside from that the stockings also just felt so much more intense than the panties did. It was a sensation over the majority of his legs that constantly gave his caged cock troubles. Hiding them under his pants didn’t help at all either. The denim of his jeans brushed over the material with every move he made, making it a near constant as well.

 

Nevertheless Jake was happy to get the stockings and panties covered. He might still feel them, but at least he had fully covered them beyond the point that anyone might even catch a glimpse of them. It didn’t take away the whole worry, but at least it made it more manageable. He really dreaded to think what the reaction would be if any of them would find out, but it was going to be a whole lot worse than having to tell them he got back with Valeria that much was certain. He doubted he would be left with any more friends  and he could probably kiss his place on the team goodbye as well with how big a taboo being gay, which he supposed would be the assumption, still was. No one might be able to do anything official, but he dreaded to think how much shit he would get from his team mates and the rather old school coach, let alone the players on the other teams when news ended up traveling.

 

After having a quick breakfast and a last check to ensure that really nothing from what he wore underneath his clothes showed Jake went on his way to his first class of the day, deeply embarrassed without even having interacted with someone. Even more than greeting his friends Jake dreaded the thoughts of what a big fool Valeria might decided to make out of him this time. He had no idea what she might be up to and it scared him to no end. Oh how he wished he could just call in sick, but that wouldn’t solve anything at all it would do was delay the inevitable and potentially cause more troubles. He could only hope that Valeria would have some mercy on him and act cool.

 

Where Jake was feeling dreadful of the day ahead, Valeria was feeling absolutely amazing, as she made her way to school? The shame of her morning walk home had long been forgotten as it wasn’t all that bad. Instead she was filled with excitement for another day toying with what had quickly become her favourite project. She was a little tired from the short night she had had, but the thoughts of what she would do and what she could still do on top if she so pleased just gave her energy. She wondered if she would be able to find any more mistakes to subtract some points from Jake and give him a real punishment. That would certainly be fun as she couldn’t help but wonder how long it would take for him to grow really desperate for an orgasm, for him to go from trying not to displease her, to trying to please her. It was definitely a change she was looking forward to seeing.

 

(If you liked this story and would like to read way more along with a ton of other stories then please check out my page on SubscribeStar: https://subscribestar.adult/fibaro I have ran into trouble with Patreon, but since SubscribeStar  doesn’t accept PayPall you can still follow me there, just make sure you connect your discord account to your Patreon account if you do so you don’t miss out on my content. https://www.patreon.com/Fibaro I have also set up a Discord server where all my available free to read work is gathered in case of censorship, so if you are interested, please follow this link: https://discord.gg/CTSErAvp )