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  Chapter 34

  Jake was still incredibly down over the news he had just gotten when Valeria barged in in a victorious mood only adding insult to injury. Clearly she had won her game and she was ready to celebrate. While she was happier than he had seen her the past couple of days, she did still remain rather cold to him although she congratute him on his team’s victory which given the circumstances did nothing but hurt as it hadn’t been thanks to him in the slightest. Other than that she made it very clear that she was here for nothing but a few celebratory orgasms and to get the chore of giving him his out of the way. Jake couldn’t help but feel like their retionship had reached an all time low and while he hadn’t wanted to be in this retionship in the first pce. He now clung to it completely with how isoted he had grown.

  True to her words Valeria did just that, really handling his orgasm like some kind of unwanted chore as well. There ended up being no passion behind it, no sensuality, making it even worse than all the other embarrassing handjobs he had gotten. After how their retionship had cooled he hadn’t been expecting that blowjob anymore, but it still hurt after how he had been longing for it before. His orgasm ended up being a real anti climax after aching for it way too long. All it did was ease up the pressure in his balls and relieve him on that front. While it was much needed relief it made him feel even worse about his current situation. Especially when Valeria said. “Alright princess, I held up my end of the bargain. You’ll need 100 points for your next orgasm.” She said it while unlocking him, clearly intending to go away right after.

  100 points, at the rate at which he had been earning his points as of te that sounded like an insurmountable amount. He would need more than a week to get all of that together, way more unless of course he went for the biggest point taker which was that maid’s uniform. Given how his previous upticks in points had he knew that if he still didn’t give in to wearing that dress his points needed would certainly be doubled again come his next orgasm. Over the past few days he had been leaning more and more towards giving in, but the anticlimactic orgasm and now this ended up being the final straws to break his resolve. He just couldn’t take this any longer as before Valeria even managed to unlock the st of his cuffs, Jake broke out into a desperate plea. “Please Miss Valeria, I am so sorry about stubbornly refusing to invest in our retionship as much as you have and I desperately want to make it up to you. Please let me make it up to you Miss Valeria, please let me be your sissy maid and forgive me for needing this long to get used to the wonderful idea you had.” He whimpered. All the pent up desperation and desire to return things to a somewhat normal state between the two of them found it’s way out in sheer pathetic grovelling.

  He was so desperate that even the huge smile that broke out across Valeria’s face after his grovelling offered him huge relief. It was good to see her feel happy and excited about something he said or did again. It has been way too long since that happened even if he was anything but proud of what he had just blurted out. He was more than a bit nervous as well Realising full well what he had just agreed to, but he would do it again even if he could take back his words. He had been so attention starved and trained on working for Valeria’s pleasure that it was all worth it. After all it was just a stupid outfit behind closed doors right? He might end up feeling ridiculous, but at least Valeria was pleased with him once more.it quickly got even better when she dropped unlocking him for a brief moment just to pull him into a tight hug instead.

  This had gone over even better than Valeria had anticipated. She never thought he would break so spectacurly, but she loved it. Finally she could drop her whole cold shoulder facade and once again show how thrilled she was with the kind of retionship they had going. It was going to be extra thrilling to see Jake in that spectacur maid’s dress serving her while all prettied up. She could hardly wait to see it as she gushed. “Oh Jake, you are most definitely forgiven and I would absolutely love for you to be my sissy maid. You’re going to make such a pretty maid, and trust me you’ll love your uniform just as much if not more so than I do. This is going to be awesome! Now go get cleaned up so we can go back to my dorm.” She spoke enthusiastically as she unlocked the st cuff allowing the once again caged up Jake to get off of the bed with a stomach spttered with cum.

  Jake didn’t really share the enthusiasm of getting into that dress, not one bit. The st thing he wanted to do was hurry to get it done, but he did want to clean the cum off of his stomach. One thing was for certain though, he did love Valeria’s enthusiasm and most of all the hug. It felt even better than he had imagined after all this time of getting pretty much beaten down by everyone. While he guessed he could still refuse to put that dress on, that would put an end to all of this and make Valeria mad all over again. No, now that he had given in he had to go through with it he thought as he quickly moved to get cleaned up and ready to leave Valeria’s smile still huge as she nearly jumped out of sheer anticipation. While she saw he was still very reluctant, that only got her more excited. Plus she had to admit she had also loved seeing how happy he had been with that hug. It was great to see how she was affecting him.

  Stepping out of his bathroom in just his stockings and thong Jake couldn’t help but feel awkward. Then again this lingerie was incredibly basic and not all that bad considering what he would soon be wearing. Valeria’s enthusiasm helped him feel a little better, but not any less nervous. For the first time in a couple of days she pulled him down and into a deep passionate kiss like she had done so many times before things had soured between them. “Go get dressed babe, I can’t wait to see you in that gorgeous dress.” She giggled as she sent him on his way to his closer with a firm pat on his ass. It turned Jake’s cheeks beet red as he put on his jeans and shirt. Still very self conscious about his lingerie and the fact that it wasn’t covered anywhere near as good as he wanted it covered. He wasn’t left with much of an opportunity to ponder about it though as Valeria grabbed his hand and dragged him out the moment he got his shoes on.

  While he did feel loved and cherished once more, Valeria’s first kiss in so many days making his heart flutter, he was still more than a bit nervous as they made their way to her dorm, every step was a step closer to what he could only think of as a disaster. Still braving it was made way more bearable now that he had Valeria’s full loving support again, unlike how he had had to brave his way too exposed for his liking lingerie alone all these days. Then again Valeria might be a great support right now, but not the greatest help. The way she wrapped a hand around his waist or occasionally squeezed his ass through his pants a little, clearly barely able to contain herself, had Jake terrified that his shirt would be riding up a little too much, or his pants legs would, exposing more of his stockings or even worse the colourful thong. Valeria didn’t seem to care at all though, and it seemed like she wouldn’t even care if he was found out as a sissy so he guessed he would at least always have her support to fall back upon which was something. He didn’t even fully realise how it only made him more dependant on Valeria’s support and affection. It had all happened so gradually, but she had become by far the most important person in his life.

  He ended up having very mixed feelings when they finally arrived at Valeria’s dorm. On one hand he couldn’t wait to get out of public, hide where no one but him or Valeria could see him. On the other hand he knew he was only one door removed from that embarrassing dress. Ultimately his feelings regarding the situation didn’t really matter as Valeria was way too enthusiastic to wait for even a moment, this was happening and as soon as possible if it depended on her. She fished out the key to her door in record time only to drag him inside and close right up. “Alright babe, here’s what we’re going to do. You’re going to step into my bathroom and use that depitory cream again and shave your face. I want you as smooth as possible for this. You can use one of my razors. I’ve used it to clean up down under, but I doubt that will be a problem. After all you and my pussy have grown quite close have you not? Now get to it while I put your outfit ready.” She eagerly excimed as she nearly shoved him into the bathroom.

  It was a relief not to be forced into what he remembered as a horrible outfit just yet, but this dey was not nearly close to one he had been hoping for. It would be like thirty minutes at most and showering with Valeria’s products while making sure not a stubble could be felt on his entire body was anything but a favourite pass time of his. It was all he was going to get though as he got right ok with the chore, subtly trying to drag it out for as long as possible. The end ended up coming way too soon still though as he was nowhere near ready yet when he ended up stepping out of that bathroom with just one of Valeria’s pink towels wrapped around his waist.

  The moment he appeared before Valeria he practically got jumped. “Ah finally, there you are. I was starting to worry you were getting second thoughts which would have been a real shame. I don’t know how much longer I could have put up with your ck of investment in this wonderful thing we have going on. For starters you can put this on.” Valeria eagerly excimed as she handed him a very pink very frilly pair of panties. The main body was made out of soft pink satin while the leg holes and waistband were trimmed in thick lush white ce ruffles. While these weren’t thong styled like what he had sadly gotten used to wearing, these were even worse. He had really thought no worse style than thongs existed for him to wear, although he loved seeing it on girls, but he was proven wrong. On top of the regur holes each panty had, these had a big heart shaped hole in the back trimmed equally in white ce and another way smaller one at the centre front for his cage to feed through. A big hot pink bow adorned each hip and another one the top of the heart shaped hole at the back. All the films and bows were terrible, but by far the worst detail to him were the words embroidered on the front. In a half circle above the hole for his cock the highly personalised words “Miss Valeria’s” were embroidered on in a hot pink colour.

  Between all the frills of this outfit when Valeria had first show it to him, Jake hadn’t even noticed the box also contained lingerie, but here he was holding a pair of absolutely devastating panties making him fear the rest of the outfit even more. What other horrid details had he missed? One thing was for certain, he was bound to find out very soon. He was barely allowed time to reluctantly slide on the horrid panties, all the satin and frills teasing his smooth skin giving him some shameful trouble with his cage when Valeria shoved a next item in his hands. Something equally delicate and frilly looking, but way more rigid with stiff bones running from top to bottom. It was a soft pink satin corset trimmed at the top and bottom with a thick yer of white ce. The back ribbon as well as well as the bones of the corset were made out of hot pink satin. The thing had half cups which would lift up his pecs into small subtle mounds. A big hot pink bow sat between the half cups and a small one decorated the end of each garter strap dangling down the bottom of the corset.

  Compared to the panties the corset was very awkward to put once could kind of step into it with the ribbon at the back being pulled as loose as possible, but that was about it. Tightening it behind his back was nearly impossible. He managed to pull it tight enough so it wouldn’t slide back down and to him that was more than fine, but to Valeria it was anything but fine. “Here let me help you tighten those babe.” She helpfully offered, not even waiting for a reply as she stepped around behind his back and started pulling the ribbons tight to the point where they were starting to become uncomfortable. She didn’t stop there either, instead she put a knee in the small of his back and started pulling them even tighter making Jake gasp and feel like he was being pulled in half. Before he knew it the excess ribbon was tied off in a big floppy bow firmly securing the corset this tight. It took a few inches out of his waste and did have the desired effect on his pecks, much to Valeria’s glee it looked like he had small breasts. It was such a hot sight, made even hotter by all the grunts and groans coming out of him. If she wasn’t so eager to see him in the rest of that outfit she would have pulled him down to get her off right then and there, but as it stood she wanted to see him wear more first.

  “Uhm Miss Valeria, don’t you think the corset is a little too tight? I can hardly breath in this thing.” Jake meekly tried to protest, not wanting to upset Valeria, but at the same time this thing was really way too tight to handle. He couldn’t believe Valeri had even managed to pull it this tight and while he could reach behind his back and untie the ribbon he didn’t dare do so without her permission.

  “Nonsense sissy, I want a maid with a pretty nipped in waist so it is perfect. Besides a lot of women have had to endure a lot more in the name of beauty so I am sure a big tough guy like you can handle a corset. Now put these on. Make sure the seams are straight and as far as the garters are concerned it is not rocket science. You’ll figure it out.” Valeria giggled as she stepped back while handing him a pair of stockings and sitting back to enjoy the show. Jake just stood there with a stunned mortified expression, really wanting to further object to the corset, but he couldn’t think of how to do so. Valeria might have just called him a big tough guy, but he hadn’t felt like one in ages wearing lingerie and doing all of her bidding. He felt like a big sissy wimp if anything, but he certainly wasn’t going to argue that. He badly wanted to be a big tough guy again and while wearing a corset wouldn’t help, he really didn’t want to pick that fight.

  Instead Jake decided to focus on the task at hand, these stockings. They were sheer white with soft pink Cuban heel, leading to a back seam which led to equally pink reinforced stocking tops. Overall the material felt even more delicate than the stockings he was used to wearing. It made him extra nervous about putting them on. By now he had had plenty of practice, and his nails were perfectly buffed and painted in that clear colour which would help, but they remained dangerously fragile and he really didn’t want to think about how he would go about repcing these. He did have to put them on though. So with the utmost care he started rolling them up only to slide his brightly pink painted toenails into the reinforced toe before slowly starting to meticulously smooth them up his legs. He moved incredibly careful and slow and the fact that he had to take those back seams into account wasn’t helping him move any faster either. He was so concentrated that he didn’t even see how Valeria was watching it all with an ear to ear grin, loving the way he was so wrapped up in the care for his stockings.

  “Damn babe, has anyone ever told you how sexy it looks when you are smoothing those stockings up your legs. I could watch this all day.” Valeria spoke, her voice dropping with lust as she bit her bottom lip, softly touching herself right in front of him while he struggled to figure out the garter tabs. Jake was absolutely mortified over the compliment however. He had also always found it sexy to see someone smooth stockings up their legs, but it was far from the kind of sexy he wanted to be. Normally when one of his flings would call something he did sexy he would mean into it, but this time he would rather hide even if it was just him and Valeria. There was no where to hide though and with the care he had to pay to these stockings doing it clumsily to hopefully break the appeal wasn’t an option. It just led to a huge relief when he finally did manage to get both stockings on with straight seams after what felt like an eternity.

  “So damn sexy. In any case, let’s continue shall we? You’re still not ready yet so put these on next.” Valeria excitedly spoke as she handed him a stiff white net petticoat followed by a soft pink one and a hot pink one only to be handed three more in the same order. The waistband of the petticoats rested right beneath the narrowest part of his waist pulled in by the corset and ended just about at the height of his stocking tops, constantly threatening to leave them exposed, or worse expose a hint of his panties. The six yers of stiff netting also stood out quite a bit around his bottom, not quite straight out by a long shot, by there was a ton of volume nevertheless.

  With his lingerie on and his petticoats all yered up Jake was finally ready for the dress, or rather Valeria finally deemed him ready as he was no where near ready to actually wear it. Standing there in his awkward state of being half dressed he didn’t have much of a choice though when she handed it to him. The dress really was the embarrassing highlight of this embarrassing outfit. Its main body was made out of soft pink satin. The hem of the skirt and the end of the short puff sleeves wet trimmed in thick white ce ruffles. The colr of the dress was in a cssic peterpan style made out of white and a cy strip with three hot pink buttons ran down the chest merely for decoration purposes. The words “sissy Jane” were embroidered onto the left side of his chest in a near cursive hot pink colour. Large floppy hot pink bows were fastened to the top of the puff sleeves and simir smaller ones were evenly spaced around the white ce hem of the skirt which stood out on top of all the petticoats. Jake was extremely reluctant to step into it, but when he did Valeria quickly and eagerly assisted by zipping up the back, pulling the body of the dress tight making it fit him like a second skin which really accentuated his nipped in waist.

  “Aaaah I knew you would look so gorgeous in this dress, I absolutely love it. Now as you may have noticed the name on it reads Jane. I just thought that a prettier name might be more suited for a prettier outfit so I took the liberty to come up with this. Whenever you are my sissied up boyfriend in a pretty dress or lingerie, you can be my sissy Jane from now on. It’s only one letter different anyways so not that big of a deal. Isn’t that great?” Valeria asked with a big smile before pulling him down a little to initiate another passionate kiss, conveniently preventing him from giving her a shocked outburst to what she had just said.

  Jake couldn’t believe what he had just heard. As if this whole outfit wasn’t ridiculous enough already, he really didn’t want a girls name on top of it, but it was already on the dress so there was no rea getting away from it besides Valeria seemed to really like it, so what harm could it really do? It was but a small indignity compared to this monstrosity of a dress he had just put on. So partly flustered by the kiss and having been able to think it over rather than giving an instinctive outburst of protest, Jake decided to just drop it and resign to his fate as Jane from now on when it was just the two of them. He tried to think of it as just a rolepy, making it a little easier to accept while he actively tried to forget what a big chunk of his life this whole thing was occupying., being with him constantly through his cage and lingerie.

  Very pleased that he seemed to just been dropping it without much of a fuss Valeria handed him the next item, an apron. It was pin white satin trimmed in hot pink ce with a hot pink strap to tie it around his waist with a very big floppy bow in the back. A pair of white ce fingerless gloves with a soft pink bow tied around the wrists followed and a soft pink satin maid’s cap trimmed in white ce. It were all embarrassing accessories, but in the end the worst of the outfit had already Ben put on so Jake simply put each item on as it was given to him feeling like a big fool in the process. It wasn’t until Valeria handed him the four inch tall soft pink cquered open toed stiletto pumps that he tried to mildly object again. “Uhm Miss Valeria, I don’t think those are a good idea. I wouldn’t want to roll an ankle or worse it would ruin my performance for weeks.” He said trying to think of a valid excuse even if at this point being out on an injury would probably help his team as they had pyed better with him on the bench. It was an extremely painful realisation, one he couldn’t quite shake which only made him feel more like the sissy he was currently presenting as rather than the soccer star he wanted to identify with.

  “You won’t my dear sissy Jane, I promise you that. I’ll be here to support you and help teach you to walk in them without issues. I’m sure with your physique and the coordination of a sportsman you’ll get the hang of it in no time, now but slide those dainty feet of yours in there and stand still.” Valeria giggled as she set the heels out right before him. She was already loving the outfit more than she had ever imagined she would and the thought of him in that outfit for her had kept her hot and bothered this past week so that was really saying a lot. Jake really wanted to find another excuse, hell even just repeat what he felt like was a very valid excuse, but instead he just blushed and complied, not wanting to find himself in a simir position as the remainder of the week. The fact that this dress was making him feel so ridiculously pathetic wasn’t helping his courage to stand up for himself one bit either.

  Aside from making him way more insecure on his feet these tall pumps also made him way taller. Not that that was an issue for Valeria at all, she had never had issues dominating Jake despite their already significant height difference. In fact it had only made her hotter to dominate a way taller person as she had found out with Jake, this whole adventure having been a road to self discovery for her as well. Seeing Jake stand there in his full maid’s outfit with his painted toes slightly on dispy through the peep toe of his pumps was just amazing. Only one more thing and it was perfect. “Alright my dear sissy Jane now all that is cking is a pretty colr to make you mine for real, so lean on over will you Jane?” Valeria spoke, giddy with excitement as she held out a thick leather strap with a heart shaped tag dangling off the centre front the words “Sissy Jane” were engraved on one side and “property of Miss Valeria” on the other.

  Mortified and cringing every time he heard the name Jane referring to him, Jake bent over lowering his neck to Valeria. There really was no point in refusing this st indignity if it made her happy. Considering how he was dressed the colr didn’t make that much of a difference anymore, or so he thought until he heard a lock click shut behind his neck, the leather pulled rather tight. He only now realised that the colr didn’t operate with a simple csp, but with a genuine lock, marking him as Jane and Valeria’s property until she decided otherwise. There was no simple walking out of here anymore. This outfit he could strip out off, his own lingerie could be hidden, but there was no hiding this prominent colr around his neck, nor taking it off without Valeria’s help.

  He barely ended up having any time whatsoever to process things as Valeria hooked a finger in the ring on his colr and swiftly pulled him down, nearly pulling him off bance in these tall heels as she made him stoop to her level for another passionate kiss seizing full control over him. The simple action of actually dictating his movements with this colr really ciming him as hers made Valeria giddy all over again. The whole process of seeing him getting dressed with this as the final cherry on top had gotten her hotter than ever before. Especially since she could once again show her excitement rather than giving him the cold shoulder. She was simply beyond herself with lust and even love. Wanting to hug, squeeze, bite, kiss, cuddle, use his oral talents and even fuck Jake all at once. Fire works were going off in her brain as she kept him pulled down with a single finger while forcing her tongue into his mouth in a rather aggressive manner.

  Jake for his part just felt devastatingly embarrassed, nearly paralysed with shame, but even he felt a rush of some kind, dare he say butterflies in hi stomach when Valeria kissed him with a passion like no one had ever done before. It didn’t make him feel any better about how he was dressed, but it definitely made him feel great in another way, especially after such a long time of feeling all alone, like an outcast in every aspect of his life. Valeria was definitely filling a void which had only grown bigger the more isoted he had grown. For as embarrassing as his current predicament was he strangely wasn’t regretting it as he felt better than he had in days. He felt cast out by the team after being rid of his role as captain, but Valeria once again gave him a strong sense of belonging now that she had quite literally cimed ownership over him.

  “Fuck you are so fucking hot MY sissy Jane. Mmm I just love how you are all mine to do with as I please or to instruct you how to please me. Those heel walking lessons can wait a little longer right here and now there is a way more important duty for my sissy maid to attend to. You’ve been getting me all worked up with that sexy outfit of yours and you’ve been getting plenty of kisses as well. It was about time you gave me some in return, you know there where they please me most. So go ahead Jane give me some kisses to grant me some relief for all that arousal you helped built. I think there is no nobler first task as my maid than getting me off.” Valeria grinned once she broke the kiss only to keep tugging down on that colr while Jake shamefully sunk down to his knees. A position he had found himself in a lot. When Valeria gleefully lifted her skirt he just dove right in and started eating her out the way he knew she liked best. Objectively he knew he was still just being used, but after all that affection and the sheer raw desire in Valeria’s voice he felt a lot better about it already.

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