(I have set up a Discord server where all my avaible free to read work is gathered in case of censorship, so if you are interested, please follow this link: https://discord.gg/v8n3fpkFma )

  Chapter 33

  Jake never ended up finding out what Valeria’s errands had been about as when she returned she had avoided the subject saying it was a surprise whenever he tried asking about it. It made it all the more worrisome for him as his current situation was built out of surprises by Valeria. He really didn’t want to find out what surprise she had in store for him this time, but then again it didn’t matter, like all those before he would just have to deal with it and take it in stride as well as he really wanted to earn himself that blowjob, making his retionship with Valeria progress, a first step in finally making her trust him hopefully to the point where he could finally go without that cage at the very least.

  Since Valeria clearly hadn’t wanted to tell, he hadn’t pressed her too much and in a sense it was maybe a relief that it was just an issue for the future and that he didn’t have to find out and deal with it right away. Not that that helped ease his worries one bit. Concentrating on serving Valeria didn’t exactly help him put his mind off of things either, but at least he had gotten quite a bit of points between the undry, dinner, the massages and the plenty of orgasm he had given Valeria before and after she had decided to get in bed for the night, business as usual for him as of te. It was plenty of embarrassing, but at least a lot more rexed than his day had been worrying about his lingerie maybe getting on dispy at each and every moment.

  The day that followed was much the same in that regard, a constant worry about part of his stockings being on dispy, even more so than the day before as these stockings were sheer bck, while he could only hope that no one would notice. At least with this being a Wednesday, not a practice day he didn’t have to worry about facing his friends, especially not after what had happened the day before. Rationally he knew that that would only make things worse, but right now he didn’t have the energy to face them, and above all else, he was still way too terrified of them finding out. At least rumours hadn’t spread about him which was a good thing, but then again it was only the second day he had his lingerie way too exposed for his liking.

  When the evening finally arrived he was way too gd to finally return to some retive peace out of the public eye even if he knew an evening of serving Valeria awaited him. It was an evening Valeria couldn’t seem to wait to get started as she had texted him to come over to her dorm as fast as possible. Usually she wasn’t this pressed about seeing him straight away and it worried him. To him it sounded like she was up to something and he had a bad feeling about it, then again, bad feeling or not he knew he couldn’t afford to refuse showing up or everything he had built towards, finally earning some more trust would be out of the window.

  As it turned out his worries were more than warranted as the thing Valeria was in such a hurry to show him turned out to be her surprise for him which she had fetched the day before. When he had knocked at the door it had almost instantly swung open. Valeria looked a lot more excited than usual as well and as it turned out that made her a lot more aggressive as well. Before Jake had even fully realised what was happening he got pulled in by his shirt and smmed against the door to shut it while Valeria pulled him down a little, simultaneously rising up to her toes to pull him into a deep passionate kiss. The element of surprise combined with the obedience she had trained into him made it quite easy for Valeria to manhandle him despite their sheer size difference. It was something she had always loved showing off, making Jake feel weak in her presence.

  “Mmm, it’s so good of you to come sissy, I’ve been dying to give you your surprise ever since I picked it up, but yesterday it was a bit te already. Now follow me, you have a present to open.” Valeria spoke enthusiastically as she grabbed Jake’s hand and pulled him deeper into her room around the corner to her bed. She didn’t even give him the opportunity to say a word or strip down to his lingerie like he was supposed to do whenever he entered his or her dorm. Once in front of the bed Jake’s worry only rose to a new height as he saw the very rge rather ft bright pink box id out on the bed for him. It was tied together with a wide pink satin ribbon and a card was tied to it reading “From CC’s with Love” A bright lipstick mark decorating one corner of the card.

  Although Jake hadn’t seen what was inside the fancy looking box, he already dreaded what he would find inside. The box looked like it came from some kind of ultra feminine boutique, a cheeky one at that given that lipstick mark. That alone didn’t bode well for him as he really really didn’t want even more lingerie. Especially not lingerie that looked like it had been very expensive and would thus probably be rather delicate judging from the packaging alone. Not only that, but judging from the size of the box it looked like it wouldn’t even all fit in one drawer in his closet. Still this had to have cost Valeria a fortune and she was so very excited about it that he just knew he couldn’t be ungrateful or he might live to regret it. What was the worst that could happen right? Like his lingerie could get much worse.

  “T…thank you very much Miss, you really shouldn’t have.” Jake stammered, trying his best to at least look a little happy and grateful. He wasn’t just being polite though, he really wished that Valeria wouldn’t have brought him this, but here he was, trying to avoid seeing what was inside as he just squirmed a little at the side of the bed as if that would make his problems go away.

  “Oh nonsense sissy, I really wanted to get you something I know you’re just going to love. Something perfect to help step up our retionship. Something that just reminded me of you the moment I saw it and I knew I had to have it, for you, for us. It’s going to be so much fun. It cost me an arm and a leg, but I think it’s so very worth it besides I love investing in this special thing we have going, both time and money. Now don’t dawdle open it up, I really want to see your reaction.” Valeria excitedly nudged him, upping the pressure for him to act happy. She knew very well that he wasn’t happy about this at all, but the prospect of seeing Jake in what she had gotten him was a major turn on. The more she could pressure him the better, even if the cost was a complete lie. Linda had been all too happy to give it to her, for the potential return on investment and if not that for the vanity project of turning the local college’s Soccer star and huge pyboy into a CC’s sissy. Valeria certainly appreciated all the help and she sure pnned on making Jake pay Linda back in time.

  Jake’s nerves in the meantime had only continued to rise. On one hand he was more sure than ever he wasn’t going to like what he found in that box, on the other it seemed like he would upset Valeria even more than he had anticipated if she really paid that much for this gift and if she saw it as a huge investment in their to him embarrassing retionship. Denying this gift would not only upset her it would now also imply that unlike her he didn’t want to invest into this retionship and he couldn’t help but fear how Valeria would interpret that and what consequences it would bring. One thing was certain, he didn’t want to find that out, but he also wasn’t confident he could deal with whatever he found in that box. He did however know that he shouldn’t dawdle like Valeria had ordered him, it wouldn’t change anything and it could only serve to piss Valeria off, so with a shaking hand he untied the ribbons and lifted the lit off the box only for his breath to stock in his throat.

  What he found inside wasn’t just bad, it was so much worse than he had ever imagined. Here he was thinking that he would get a box full of even more frilly lingerie, tons of it, but instead the box contained a full outfit, one which from the looks of it was a sort of maid’s outfit judging by the apron. A very frilly very pink outfit containing everything down to lingerie and even heels. “It’s gorgeous isn’t it? And so very you as well, pretty, pink and frilly. Seeing you prance around in your lingerie has been fun and all, I mean it does look pretty on you and I love seeing and hearing how much you enjoy yourself, but it just isn’t the same as that gorgeous princess outfit that sparked your excitement isn’t it sissy? Come now there’s no denying it. Don’t think I don’t hear those cute grunt of yours whenever your cage gives you troubled because you get a little too excited about your lingerie. “Valeria informed him, only to unch an immediate counter to the denial she could see form on his lips already. She never gave him the chance to verbally deny it, and to prove her point she hugged him from behind and gently ran her hands up his inner thighs, brushing his pants over the sheer stockings he was wearing underneath.

  It almost instantly got some light grunts out of Jake who’s cock was giving him trouble in his cage much like Valeria had pointed out as a sign of him loving his lingerie. Valeria for her part couldn’t help but chuckle adding insult to injury. He couldn’t believe his cock was so fast to react to such mild touches, and while it wasn’t exactly fair to feel Valeria’s breasts press into his back when she touched his already sensitive smooth inner thighs, it made it hard to deny what Valeria had just said. He couldn’t help but feel like the sissy she was calling him when his body betrayed him like this, but the fact remained that that outfit was the st thing he wanted to wear. He really didn’t want to wear more girly things, let alone a complete outfit especially one as frilly as that one. When he had wished he could hide his embarrassing lingerie at home as well, he really hadn’t meant with a skirt. He already felt like nothing but a weak sissy, especially in Valeria’s presence and this outfit certainly wouldn’t help. Part of him was also just afraid that his cock would actually respond in the same way as it had to that horrible princess dress and he really didn’t want to deal with that confrontation. He was having more than enough trouble with processing his reactions to his lingerie as it was.

  Valeria for her part was more than pleased with his reaction, the denial and pent up pleasure caused by his cage paired with the fact that she had been conditioning him to respond more and more to the sensations of his lingerie were definitely paying off. As of right now she really wanted to continue to up the pleasure, badly wanting to see Jake in that outfit. Still she didn’t pn to straight up force him into it. She wanted him to put it on himself so he would have a harder time distancing himself from it. “See, it seems like something down there’s already aching to get into that pretty outfit. In any case, while I still have that princess dress for you to try on whenever you want, I didn’t think it was very suitable right now. Princesses don’t work and serve like you do, but as my sissy maid you can have the best of both worlds, you can still earn yourself those precious points by completing your tasks and you get to dress up in this amazing outfit which looks like it was made for you! So what do you say Jake? Are you just as eager to get into that outfit as I am to see you in it? Do you want to step up our retionship and take it to the next level as much as I do? Will you be my sissy maid whenever we find ourselves in the privacy of our dorms?” Valeria bombarded him with eager questions which only made it sound all the more official and embarrassing to Jake. A sissy maid was the st thing he wanted to be, it was infinitely worse than just doing chores in his thong and stockings, But Valeria seemed so extremely set on the idea.

  “Uhm, it really is gorgeous Miss, and I really appreciate the gift. I truly do, but I don’t know. Those heels, I wouldn’t want to break an ankle. I think all those frills might also end up getting in the way of properly serving you Miss. It’s also just a bit much I think.” Jake carefully weighed his words, trying to get out of wearing this outfit in the politest way he could come up with. Even with something so over the top as this new outfit lined up, defying Valeria was still a scary nerve wrecking thing to do. A few weeks back he would have outright refused, questioned her sanity even. Trying on that princess dress for a bet was one thing, but agreeing to be a full time sissy maid when he wasn’t at css or practice was way too much. Yet with how beaten down he was now firmly putting his foot down was just something he couldn’t work up the courage of doing. His cock and reputation were quite literally in Valeria’s hands, he couldn’t upset her or he would literally lose his orgasms and whatever respect he still had. He could at least still come back from this low if people didn’t start seeing him as a huge sissy he thought.

  “Don’t you worry sissy, I can definitely teach you to walk in heels so you won’t twist or break an ankle. I’m also more than happy to be very patient with you and give you all the time you need to properly serve me while tending to your gorgeous outfit. I also don’t see why it would be too much, it’s just the two of us and you really enjoy your delicates, that much is certain. Unless of course you are afraid you would erupt in a spontaneous orgasm over wearing this outfit and be unable to function wearing so many frillies. Is it that which you mean by too much? That would be highly amusing and I would love to see you so happy. The choice is yours of course. The choice of whether or not you want to be my sissy maid, make me happy, invest in this retionship and help bring it to the next level. Plus since I really want to see this outfit put to good use there are some points to earn as well. Let’s say ten points for every day you wear your pretty new outfit.” Valeria excitedly expined giving him all the more reason to agree to being her sissy maid. The idea of him having an accident wearing his dress really sparked her arousal, she really hoped she could at some point get him conditioned enough to the sensations to make that happen. Right now she doubted it would though, not while locked up at least.

  Jake for his part really didn’t want to learn how to walk in heels. It was definitely a skill he could do without. Valeria’s patience was just a counter to an issue that he had made up, an issue she put a way more embarrassing spin on by assuming he wouldn’t be able to contain himself when wearing that outfit. He doubted that would be an issue, but paired with his shameful reactions he had been made to acknowledge multiple times by now, a part of him couldn’t help but worry that he would actually react the way Valeria had described. If that happened how could he ever look at himself in the mirror again? He had to admit that ten points he could earn on a daily basis was a great perk considering how many things he had to do to earn himself that many points, but then again this really wasn’t worth more frequent orgasms. It was a relief that Valeria wasn’t outright telling him to put this outfit on though. It offered him an out of this horribly embarrassing predicament. An out he desperately clung on to. He knew Valeria wouldn’t like it, but then again considering what she was asking of him that was a risk he was willing to take. He had to draw the line somewhere right? Even if it was scary.

  “Thank you very much Miss, that’s all wonderful and I’m very grateful, but I fear I’m really not ready yet and I feel like that means I should decline for now at least.” Jake spoke with a shudder as he looked back down at that horrid outfit. He wasn’t ready for that at all and he never would be. It was outrageous yet he didn’t dare say how he actually felt about it, instead going for the least committing way possible. He wanted to say no, never, but he didn’t dare. All he could do was hope that Valeria would keep buying that excuse so maybe he could avoid this outfit indefinitely. He knew he should make a bigger stance, making his real feelings clear since the choice was his according to Valeria, but he simply didn’t have that courage anymore after weeks of being pushed deeper and deeper into sissy submission.

  “Alright if that’s how you feel about it. Then I guess you can just close that lid again, strip down and give me at least an orgasm for all the trouble I went through trying to get the both of us something fun.” Valeria said her tone instantly changing to a cold ft one as she broke the hug she had been giving him from behind and simply sat down. Her disappointment was palpable and it made Jake feel awful somehow. He couldn’t help but think that he shouldn’t care that much for all that Valeria had put him through, but he did. On top of that he couldn’t help but worry what that disappointment might lead to for him. He already doubted that he would still get that blowjob and it was devastating, all he had worked towards ruined by a simple no thank you. Still he just couldn’t justify putting that dress on even if he had to admit he was tempted just for a brief moment to resolve how Valeria currently made him feel.

  Nevertheless Jake felt a certain amount of relief when he put that lid back on the box, removing that awful outfit from view. It most definitely felt like the right choice as just thinking about putting it on made him shudder yet again. With that box closed and put away Jake quickly stripped down like his lingerie as had become a daily habit by now. He tried very hard to be on his very best behaviour to hopefully cheer Valeria up and let her forget about that horrid outfit and how he had refused to put it on, so without dey he moved in under her skirt and started working on giving her that orgasm. In a way he was also kind of relieved that he could hide from Valeria at least a little so he didn’t have to see her rather sour look. Not that under her skirt was his preferred hiding pce.

  Just like that things were back to the way they had been for the past two weeks. A worse version of it that was as he just did his chores, to earn his points, alongside giving Valeria orgasms on demand. She on the other hand remained rather cold and distance towards him and it was agonising in a way he hadn’t been expecting. He shouldn’t care so much about how Valeria felt but he did. After putting her happiness above everything else for so long it was an almost natural response he couldn’t just turn off. It just made him try even harder to please her in other ways, but it didn’t work. Throughout the evening Valeria remained as cold as she had been after the initial refusal. After she had gotten her massages, her diner and a couple of orgasms she even ended up just kicking him out to go back to his own dorm for the night. He hadn’t been made to sleep alone for quite some time now and although sleeping with Valeria, having their stocking cd legs intertwined was awkward, it did feel strange and lonely even. Plus it did make him miss out on quite a few points earned towards his orgasm by providing Valeria with orgasms as well as she usually wanted a few just before going to sleep and a few more when waking up. There was an easy fix for it all, but it was one he just wasn’t ready to make.

  Meanwhile Valeria had gone straight to her magic wand the moment he had left. While it was a little disappointing that she didn’t get to see him in that outfit she had gotten, it was fully expected. The way Jake had tried his hardest to make it up to her in other ways, looking nervous and concerned throughout it all was just too precious. All her efforts were clearly paying off as she had a real genuine grip on him. This had actually come to prove that her happiness was central to him and it drove her wild with excitement. Sure part of it still relied on his need for orgasms, but clearly it was way deeper ingrained than just that. She was so excited to see that in action that she actually had a hard time to keep giving him the cold shoulder, but she was very motivated to keep it up as she was certain it would pay off.

  The day that followed ended up going much the same. Valeria while still making use of his tongue at lunch remained cold and distant towards him as things were looking worse for him than they had in a long time. After all he had sacrificed his male underwear for Valeria, but it seemed like their retionship had taken a huge step back. He still avoided his friends, or now old friends he guessed at all times making Valeria pretty much his whole world. Practice much like the one on Tuesday only left him feeling worse as well. It made him feel so bad that he actually considered putting on that uniform just to see Valeria happy so things could at least go back to normal, or better than normal in their retionship, but just thinking back to how it had looked made him shudder and reconsider making his Thursday pretty much a repeat from Wednesday, only with a load of undry for the girl’s soccer team on top.

  Friday which followed was more of the same, but at least it announced the start of the weekend. Something which he had very mixed feelings about. It meant that he could spend most of his time inside, taking away the worries about getting discovered each and every time he appeared in public with his lingerie less than adequately concealed. At the same time it meant he had a match coming up which considering how the practices had gone and the fall out with his friends was a terrifying prospect. There was way more on the line than just a good or a bad practice and the biggest pilr of his public identity revolved around just that, his role as soccer captain. He had never felt as nervous about a match as he did right now and he just couldn’t get over with.

  Being overly aroused and in desperate need of an orgasm wasn’t helping him one bit either. He had never been without an orgasm for this long and the constant sensations of his lingerie and sleeping in satin sheet were only making things worse especially with how they had started to affect him more. Normally he would have gotten an orgasm today, on Thursday even with a bit of luck, or most definitely when he had worn that sissy maid uniform Valeria had gotten him. With her severely cooled attitude towards him he hadn’t been able to get together the necessary points though and when he was sent home that night to sleep alone yet again, he knew he would only get his orgasm after the match.

  When the match arrived on Saturday he hadn’t yet seen Valeria that day, his balls were hurting and he was overly nervous facing the guys yet again. The scoffs he gotten when meeting with them only made it all the more painful. There was nothing to be done about it but try to give the match his all in order not to piss them off even more. With all that was on his mind and the discomfort of his aching balls that was easier said than done however, as had been a trend for a while now, his performance just kept on deteriorating. His head just wasn’t in the game, with serving Valeria all of his free time and his sheer nervousness to head out, there had been no real time or opportunity to workout out side his practices, and the tension between him and his friends which had grown way worse since he had started avoiding them all contributed to that. It was so bad that he was benched in the second half, and much to his shame the team pyed better and actually pulled out the victory where they had gotten behind when he was on the field. There was a big team wide celebration on the field when one of his ex buddies scored to get ahead, one where all but he joined in.

  It was good that they had puled out the win, great even, but it only deepened his shame as he had clearly been what was holding them back. He hated that feeling, but there was nothing to be done about it now, he was just gd that his ex friends were too busy celebrating to really care or point fingers at him at the moment. It was something he could really do without. He couldn’t believe he couldn’t even feel happy that they were winning yet here he was, mortified while his friends and the crowd were going wild. Rushing home right after the match had never felt this necessary before, but he knew for sure that in the locker room he wouldn’t get away from the scorn of nearly losing them the match before one of his ex buddies had saved it. It didn’t feel good at all to run from them yet again, but it sure didn’t make him feel even worse like going to the locker room most certainly would. Besides it wasn’t like he could change or shower there anyways.

  Instead he was left to the retive silence of his own dorm while he had a nice long shower, taking care of the slight stubble that had grown back on his body like Valeria demanded only to chance back into his shameful lingerie and nothing but his lingerie. While it was good to be away from other people it didn’t help him process his shame at all. Without any distractions he just kept on mulling it over in his head, how he could ever manage to salvage things with his friends and how he could get back on top of his game so they wouldn’t be able to avoid further bme for bad performances. It all seemed impossible to manage, for that he would need to get out of his cage and out of his lingerie, but that meant earning enough of Valeria’s trust to earn that privilege again as he couldn’t let anyone find out he was a sissy. Earning that trust seemed further removed than ever though.

  On top of all of that came the ever growing need for some positive social interactions. Since he had been avoiding his friends and upset Valeria, a cold distant Valeria was the only kind of social interaction he had had this past week. It made him feel incredibly lonely and unappreciated. Still just the idea of that outfit she had gotten him sent chills up his spine. Looking down at his current smooth body cd in a frilly vender thong and a pair of white sheer stockings dispying the hot pink nail polish on his toes which he had applied to both Valeria and his nails was more than devastatingly feminine already. The bulge his chastity made underneath only made it worse as well. No he really didn’t want to go further down the sissy path, but at the same time he was leaning more and more towards trying to justify wearing it as well. After all no one would see it and his only social contact Valeria would be extremely happy with it, or that’s what it had looked like when she had introduced him to it.

  Adding insult to injury Jake was pushed even deeper as standing there in nothing but his lingerie looking for something to distract him with, a text came in, one from his coach. “Hello Jake, it pains me to do this, especially over text, but I saw no other option given how you weren’t there to address in person. After careful consideration and evaluation over the past few weeks as well as a discussion with the team, I have come to the conclusion that it would be best if you took a step back from being the captain. Effective immediately Tom will be taking over that role. Don’t let this get you down, I hope a relief from those responsibilities will give you the time and space to get back on top of your game. The team needs you!” The message read and while it was definitely understandable given all that had happened it was devastating nonetheless as Jake ended up staring at the wall in utter shock, trying to process what he had just read. His biggest pride gone just like that.

  (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:///Fibaro )