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  Chapter 37

  Valeria had kept him down on his knees, eating her pussy for ages, not to one, two, but five orgasms. All this time of giving Jake the cold shoulder, partially denying herself in the process, seeing how it affected him only to finally see him give in to her demands and put on that sissy maid uniform to please her. It was so fucking hot and had her nerves firing on all cylinders as she felt horny like never before. More than ever it was a feeling she didn’t want to give up, and she loved Jake, or rather Jane for making her feel this way. His blushing obedience and the adoration in his eyes now that she showered him with affection again were just so very cute. It made her want to eat him up.

  Having had enough and feeling quite overstimuted Valeria had fallen back on her bed with a deep delighted sigh. “Wow Jane that was absolutely amazing. I love you my sweet sissy maid. Now just give me a second because, wow!” Valeria sighed as Jake was left on his knees the pussy having been roughly pulled away from his now sopping wet face. It was embarrassing and yet he couldn’t help but feel butterflies in his stomach for some reason. Valeria just sounded so genuine when she told him she loved him and it was downright amazing to hear after all this time of feeling down and alone. He guessed he loved her too, but it felt so wrong somehow. Wrong but so good to have someone who cared about him like this.

  They both ended up staying in position for a good few minutes, Valeria coming down from her amazing intense series of orgasms while Jake was still trying to wrap his head around this whole situation and how it made him feel. His cock for one was giving him a lot of trouble in the cage. He had never stopped being turned on by the sensations of his panties and stockings. If anything they had only started affecting him more, often giving him trouble with his caged cock although he had always liked to bme that on the denial rather than the lingerie, but deep down he knew that wasn’t true. That much definitely got proven now that he was wearing a whole outfit again. The sensation of all these delicate fabrics all over his body, the petticoats brushing over his sheer nylon cd thighs. It all added up to an uncomfortably attempted erection, blocked by the cage despite the fact that Valeria had helped him get off, only about two hours earlier. The scent of pussy sure wasn’t helping him keep it down either.

  Then there was the matter of Valeria, he still wanted his old life and his freedom back, but now that he had her affection back he realised more than ever that he also cared about her and her affection more than he had imagined. Sure she was the one doing this to him, but she also seemed to be the only one to care deeply about him, especially after losing all his friends. It was really messing with his mind. So far earning Valeria’s trust until she allowed him to be free of that cage was still the only decent pn he had to regain his freedom and at this point he was giving up trying to search for another pn. Partially because he had began losing hope of finding another option, but if he was truly honest with himself, keeping to that pn also meant that he didn’t have to feel bad about going with what Valeria was saying. He didn’t need to feel bad about this retionship that way because it was his best option. The fact that he got to be with Valeria and see her happy was an added bonus.

  Jake was snapped out of those thoughts when Valeria came back to her senses, still kind of orgasmic drunk, her heart once again racing as she saw him in his pretty dress. Then without warning she leaned forward, hooked a finger into his colr and pulled him towards her for a deep passionate kiss, tasting her own pussy from his still wet lips as she looked straight down into his eyes, their entire height difference nullified by him being on his knees. “That was so hot Jane, thank you for agreeing to be my sissy maid. Now I was just thinking about something. You look so very pretty, but that look could use just a little more umph if you know what I mean. Would you let me do your hair and makeup pretty please? I’ll give you an additional five points for it and it would make me very happy.” Valeria spoke, excitedly biting her bottom lips while she awaited his reply, their faces only inches apart while she held his colr while he kneeled between her legs. The shocked, embarrassed, but also hesitant look on his face was great. Unlike with the outfit she wouldn’t be as cold if he disagreed, this outfit being plenty of great, but she really wanted to milk this opportunity for its full potential.

  Five points was a lot, as much as doing the whole team’s undry which was still awaiting him and with no effort for himself. It would also make a dent in those hundred points he needed to earn, paired with wearing this outfit, and all those orgasms he had already given her he would reach twenty points and that this quick. Hell he would easily be able to get to more than thirty today he imagined. If he hadn’t been so stupid as to refuse wearing this outfit for so long, Valeria probably wouldn’t have raised the points, and then he would have definitely earned himself an orgasm and probably even his second blow job tomorrow. Still at this rate of earning points even reaching a hundred would take less time than his previous fifty. Paired with he fact that he was pretty terrified of refusing Valeria again, and the fact that at this point given how he was dressed, makeup or not probably wouldn’t make all that much difference, Jake ended up giving in. “Yes Miss Valeria, you may!” He shamefully said, not even able to look up at her, looking down at her p instead.

  Valeria quickly rectified that though as she put a finger under his dripping wet chin, and lifted it up to force him to meet her eyes. The shame in them was just delicious, making her giddy all over, but for now she was still dealing with being too over stimuted to make use of his skilled tongue again. It was probably a good thing if she wanted the makeup to st any amount of time as she was thrilled that he had agreed. There was still so much more that she wanted to do though so it would be a good thing not to have to constantly retouch his makeup, although she imagined the used whore look would be quite the sight as well. It just wouldn’t really fit with outrageously cute and frilly maid’s outfit. Either way she wanted to show her appreciation and so she leaned down and shared in yet another deep passionate kiss with him. “Thank you so much Jane that’s awesome. You’ll look so fucking hot and pretty once I’m done with you.” Valeria gushed while Jake could only squirm a little, embarrassment stayed reigning supreme, but this overload of affection did feel good. He couldn’t help but worry a little about looking fucking hot and pretty like Valeria had put it though. Maybe this had been a bad idea after all, but it did feel good to see Valeria this over excited about him.

  Leaning off to the side Valeria grabbed her brush and a makeup kit from her nightstand before quickly returning her full attention back to Jake with an excited smile. She just loved looking down on his kneeling form between her legs, even if he wasn’t eating her pussy at the moment. “Hush now babe, just keep still and rex. This is going to feel amazing, I promise.” Valeria spoke softly as she took her hairbrush and started brushing out Jake’s by now shoulder length hair. He hadn’t been to the barber in far too long, having been too anxious about being out in public. Going to his csses had been pretty scary already as sitting down always made his pant legs rise a little, posing a danger to his stockings peeking out. That was with his legs hidden under a desk. At the barber shop he would be stuck in a chair for a while, a chair in the middle of an open room where people could see him from all angles. It simply was a no go for him.

  Sitting there with Valeria brushing his hair Jake had to admit that it did feel really good, almost like a scalp massage, the bristles of the brush running over his scalp, the gentle tugging, and the genuine loving care Valeria was paying to his hair. It was all absolutely amazing, and very rexing. It got better with each brush as well as the bristles were sliding smoother and smoother through his hair. Valeria for her part was loving it as well, like she had her own big doll to py with and while she had never really been into dolls, pying with this jock who she had made into her sissy was very exciting though. She also loved seeing how Jake was genuinely enjoying it, and didn’t mind brushing a little longer than necessary because of it. She genuinely did want him to enjoy being her doll, especially since that embarrassed look never waivered.

  Eventually the hair brushing did come to an end though Valeria ended up collecting all of his hair into a tight high up ponytail. The shoulder length hair was just enough to make it look good rather than awkward. She noticed there were some split ends, but she decided not to mention them just yet. She really like how he had been growing out his hair, probably more out of awkwardness in public than anything, but she badly wanted it to get even longer and she wasn’t quite sure she would manage to get him to a salon to get his hair cared for just yet. Sure she was making big steps, but all of this was private for now and getting him to such a feminine public pce would be too much of an ask. She definitely pnned on making him a bit more comfortable with the idea though. For now she was just happy with her sissy maid, and even more so when she tied that ponytail together with a pink floppy satin bow, making it go together nicely with his outfit. The fact that his hair glistened nicely thanks to the conditioner she insisted he used just made it that much nicer.

  With his hair just the way she wanted it Valeria leaned down for another kiss. “Alright babe, why don’t you close your eyes for now? It’ll be easier that way as I wouldn’t want to accidentally poke your eye with a makeup brush. Thanks again for letting me do this, you’re really stating to shape up nicely.” Valeria spoke softly upon breaking the kiss, loving how her words made him squirm a little. This was just way too great, especially when he did close his eyes, submitting to his makeup session. With his face still glistening with her juices, the first step was cleaning up her canvas a little. Not that she minded as she carefully cleaned him up with some tissues. Sure she loved marking him as hers and the scent of her pussy had always been a delightful way to make that happen, but then again painting his face was a way more clear and visible manner and since it was she doing the painting she guessed it still counted as him carrying her mark.

  While not as pleasant as the hair brushing, getting his makeup done didn’t feel bad either. While he did often comb his own hair, the feeling a little bit simir to the brushing, the feelings of getting his makeup applied were completely alien to him. She could feel some light brushing on his eye lids, on his cheeks, something pulling a little on his eyeshes and some sharper pressure just around his eyes along with something tacky on his lips. It was all so strange and completely embarrassing knowing what he was letting Valeria do, but he reminded himself that it was for the best to make Valeria happy. Besides he was way more embarrassed about the petticoats brushing over his bare ass through the big hole at the back of his panties.

  Unlike his hair, the makeup took a while longer to get completed and when it did Valeria was over the moon with excitement. “Oh Jane you look so fucking incredible right now. I would want to kiss you but I don’t want to smear you lipstick before you’ve had a chance to see it. So lets give you a look at the new and improved you shall we my sexy little sissy.” Valeria giggled while Jake could only blush. He didn’t particurly care to get a good look at himself in this outrageous outfit, with his hair and makeup done. The less of it he saw the more he could ignore it because he really did feel like a sissy, folding so easily and putting on such outrageous things. He wished he could ignore it all, but the sensations of his new lingerie, this outfit, and even his hair and makeup were overwhelming.

  Besides it wasn’t like Valeria gave him much of a choice anyways, getting up and urgently helping him up as well. Sitting on his knees felt a lot safer, especially with these tall heels, but he didn’t want to fight Valeria. If anything his courage to stand up to her had taken another huge blow with his outfit and makeup. Over his week his confidence had slowly been chipped away to the point where he had actually given in to this outfit, but now he didn’t even have the courage to go look in the mirror, let alone stand up to Valeria. “Alright Jane when you walk in heels it is important to take small heel to toe steps. Keep your back straight and neck straight to put your centre of gravity right above your feet, tuck your elbows tight against your waist, but keep your forearms stretched out to the sides to help with your bance. Don’t worry, I’m here for you and I’ve got your back.” Valeria said as she gave the first rudimentary instructions on how to walk in a way that sounded like it made enough sense. For today her main goal was to get Jake to manage his heels without help. She could focus on making his walk more swishy ter, it would be better that way as she didn’t want to over push him either and so far she had heaped a lot upon him in a very short time.

  Scared to twist an ankle, and grateful for Valeria gently holding one of his arms just in case he would fall, Jake tried his best to do as Valeria instructed simply to prevent that. Not only would a twisted ankle be terrible for his soccer career, it would also be a huge pain to expin. How the hell was he going to get away with avoiding the mention that his accident had been caused by him trying to mince around in pretty high heels. There was only one way to prevent all that shame and that hassle and that was to not screw up. He felt like a huge fool taking such small steps with his elbows tucked against his waist like that, but as Valeria guided him forward he just did it, putting all his concentration towards not messing up his walk.

  While the strut looked clumsy at best, Valeria just loved it and she could see Jake was trying really hard. She doubted his reasons were to be able to strut in heels like a perfect sissy, but that didn’t matter much to her, the fact that he was learning and believing that all those steps were absolutely necessary was all that really mattered. She didn’t mind holding his arm either, if anything she quite loved the hands on approach teaching him to walk around in heels. Oh she could already imagine him mincing around to serve her and thinking I taught him that while sipping a gss of wine he had already served her. First she couldn’t wait to see how he would react to his mirror image. When they eventually reached the full length mirror attached to the back of Valeria’s dorm door, she could barely stifle a giggle when she saw his jaw drop. It was even more thrilling than the grunts of discomfort from his cage she had picked up along the way.

  Having seen the outfit Jake knew it would be bad, but the image reflected to him, actually seeing that outfit on himself made it so much worse. With how over frilled and puffed up in strategic pces the dress was, it negated a lot of his athletic frame from standing out. Still with how much of his arms and legs were still on dispy there would be no doubt in anyone’s mind that he was a guy wearing such a frilly sissy up do. Simirly his face was significantly softened by the expertly applied makeup. It didn’t completely conceal his jaw, or the bushier brows, but it was shocking how drastically it had altered his face either way. Matching the outfit Valeria had mainly used a mix of pinks. A slightly too pale foundation, giving his face a smooth more doll like complexion. His blue eyes were really made to pop out with wing tipped bck liquid eyeliner and plenty of mascara to give his shes extra length and volume. His eyelids were painted in a blend of dark pinks that grew lighter the higher up it went. The pink blush was expertly applied to give him a permanently flustered look as well as highlight his cheekbones, but the most worrying by far were his lips. He could only describe them as cock sucker lips and given Valeria’s earlier teases about trio’s he couldn’t help but shudder all the more thinking about them like that. The looked both bigger and fuller, in a bright hot pink colour finished with a wet looking lip gloss. With use of some strategic contouring his nose was made to look a little smaller, and his chin more rounded. Finishing everything up, his hair tied into that ponytail with a big pink bow looked cute if anything and it only made him shudder all the more.

  Jake was left utterly speechless, what was he even supposed to say to this? Hell even his blush didn’t make it through the heavy makeup and it sure was bright enough underneath. Apparently the answer was nothing at all as Valeria was all too happy just soaking in his shocked embarrassed silence for a little bit as he kept on giving himself once overs until she took charge to get him away from the mirror once more. “Alright Jane, you’ve admired yourself enough for now. It’s time you got the hang of those heels so you can do your chores without help my pretty little sissy maid.” Valeria giggled as she guided him away from the mirror again to walk him around her room for practice, clearly in the lead while Jake did his best to follow and carry himself the way he had been told to do so by Valeria. The fact that it seemed to work to some degree only further convincing him that it was necessary to do so. He didn’t really stop to think how much more ridiculous his walk was compared to that of a number of his flings who had worn heels.

  For the next ten minutes Valeria stayed right at his side, keeping a firm hold of his arm so he had the necessary security to keep on practicing while she walked him across the small room, his heels clicking loudly on the floors. With his arm sticking out and putting no conscious effort to keeping his hands extended, his wrists automatically hung limp making his strut look all the more prissy it was the very least of his worries though to the point where he didn’t even realise it. All he paid attention to was staying up right and getting through this. Plus the attention his outfit forcefully demanded, for as much as this whole outfit embarrassed him, it also really turned him on, making him struggle hard with his cage. It was awful making him feel like such a big sissy. The stockings and thongs he wore on the daily already served as turn-ons, but this was a whole new level.

  The stockings felt so much more delicate still than what he was used to wearing and the way they brushed over one another with his small heel to toe steps, rather than brushing over the rougher jeans like what usually happened was a complete different sensation, one like Valeria gave him when she worked up to finally giving him some relief when he earned his orgasm. The huge yers of net petticoats swishing around, lightly and teasingly brushing over his stocking cd thighs and exposed ass gave an even more intense sensation. One he was trained to connect with pleasure even if he didn’t really realise that connection was building, his body was certainly reacting to the sensations and stimutions of his outfit, something that was bound to become ever more pronounced the longer he remained denied.

  “Alright my pretty sissy Jane, I think you are getting the hang of it a little so why don’t you go and do a first simple job and pour me a gss of white wine, then carry on practicing some more?” Valeria chuckled as she took a seat on her desk chair. She could instantly see Jake grow a lot more nervous now that he was left out on his heels without the support of her arm to back him up. The nervous “Yes Miss” he replied with was just too cute. It mean so much more to her now that she actually had him colred, she still couldn’t get over how awesome this was.

  Jake on the other hand thought that it was anything but awesome. He had just been starting to feel a little more confident on his heels, feeling like he would get through this without seriously injuring himself with Valeria’s support, but now that that support was taken away, he was right back to worrying he would sprain an ankle at any point. It was scary and embarrassing, but at least Valeria was happy again. Plus it would be a step closer to gaining her trust enough to hopefully get rid of this cage permanently. He reasoned, trying to make himself feel a little bit better about giving into her this easily. It didn’t make gathering his courage to actually walk around without support any easier though, but after a bit of bracing himself Jake did take his first scary steps alone. He just had to keep in mind what Valeria had taught him, keep walking the way he had for the st ten minutes. He would be fine he hadn’t actually had to rely on Valeria’s support to catch him at any point so this wouldn’t be that much different.

  It took a few moments, but eventually Jake did build up the courage to walk off on his own, straight to the very basic kitchen a pce he embarrassingly had to admit he knew very well. Having been cooking all of their meals either at her pce of his Jake had come to know both their kitchens inside and out. He didn’t have to look for the wine gsses at all as he took one out and poured Valeria a gss. While it was something he had done rather often, he couldn’t help but feel more embarrassed about it now that he was wearing this eborate overly frilly pink maid’s uniform. Somehow it felt like he belonged more in the role he had taken on for some time now. The role of doing all the chores and serving Valeria. Aside from his outfit, not much had changed, but that was more than enough to leave him cringing harder at everything he did. The sensations of this outfit turning him on big time didn’t help one bit either.

  “Here’s your gss Miss.” Jake spoke, his face burning red under his makeup when he walked his way back to Valeria feeling like the biggest fool around. Valeria wasn’t helping one bit as she took it with a huge smile, swirled it around and smelled it as if she was at a fancy restaurant. Taking a small sip she nodded her head. “Mmmm, it’s an excellent wine Jane. Thank you very much. I have to say the service in this establishment has definitely improved big time, and I love the new uniforms. Now hold on a second such great service deserves a tip.” She smirked as she fished out a one dolr bill, flipped up his skirt and slid it right into his stocking top at his inner thigh, giving it a soft pat before bursting out in giggles. She just loved the mortified look crossing Jack’s face just like she loved the grunt her action got out of him, not one of shame, but that tell tale sign of his cage giving him trouble yet again.

  Stunned Jake didn’t really know what to do or how to react other than giving her another. “Thank you Miss.” Did he take that bill out now, or did he just continue walking like nothing had happened? Should he wait for Valeria’s permission to start walking again? He really didn’t know, and he felt more than a bit embarrassed about it. Here he was standing at attention like a maid waiting for her instructions. Taking that bill out would probably mean exposing his panties again which he really didn’t want to do, but walking in heels was another thing he really didn’t want to do. He was equally uncomfortable just standing there in absolute silence, with Valeria eyeing him up while quietly sipping her wine. The stares and silence made him incredibly nervous to the point where he couldn’t help but squirm a little, shifting on his high heeled feet, fumbling with the trim of his skirt a little. Eventually he just had to break the silence. “Uhm Miss Valeria, I’ll go practice on these a little more if you don’t mind.” He said before walking off to the far side of her room just to have something to do as he tried to keep his mind on moving exactly like she had told him he should.

  For Valeria it had all just been a fun little game to see how he would react, and she just loved it. After all she had put him through and in this outfit Jake couldn’t be further removed from the assertive confident asshole he had once been. He really looked like the shy embarrassed maid and she loved it. “Sure thing my sweet sissy Jane, that’s a great idea, you can really use the practice.” She giggled as she took another sip from her wine, simply crossing her legs and leaning back while she rexed and followed the nervous dolled up soccer star mincing about her room. It made her feel so incredibly powerful. This was most definitely the life and she loved seeing how Jake was slowly but surely gaining a little bit of confidence on those heels, transting into a more gracious walk. It wasn’t the silly sissy mince she wanted him to adopt just yet, but it certainly wasn’t a gracious sexy walk like most women in heels either.

  Without Valeria giving any other instructions Jake just kept walking up and down the room, the uncomfortably tall heels really doing a number on his feet and calves. Sure his legs were about the most well trained part of his body but still this completely unnatural and new to him four inch tall elevation under his heel was just too much for him to handle, putting a completely different strain on his legs and feet than what he was used to, and it only got gradually worse the longer it went on. After close to an hour of walking around in the small room his legs were really killing him. The only change he had gotten in the boring, harsh and embarrassing walking routine was when Valeria had asked him to pour her a gss of water. This time luckily without giving him a tip as she sent him right back to walking while she followed everything in detail, sprinkling in the occasional compliment, or a slight remark to turn his walk into a bit more of a sissy mince.

  Jake’s legs and feet could really use a break by now, but he didn’t know how to ask for one until it all got too much and he simply decided to come up with an excuse to get himself that break. “Uhm Miss Valeria. I think I’m slowly getting the hang of these so I was wondering if I could perhaps get to my chores now? Starting by giving you a rexing foot massage?” Jake asked nervously as she stopped before her. It was mortifying to ask to give her a foot rub while it were his feet which were suffering so much, but it was just about the only chore for which he could stay off of his feet for a good while. A pedicure was also an option, but that had pretty much become a Sunday ritual.

  “Sure thing Jane, you go right ahead. You’ve made some great improvements already and I too think you’re ready to get on with business as usual. A foot rub would be great and maybe a back rub afterwards, get all that match tension out of my body so I’m ready to go celebrate our victory with the girls tonight.” Valeria grinned as she leaned back a little further in her chair, uncrossed her legs and extended her feet out towards Jake who looked mighty embarrassed. Still he didn’t hesitate to perform, getting down on his knees near instantly and took Valeria’s feet upon his apron and skirt cd p to start the massage.

  It felt great to be off of those damn heels for a little bit. After what Valeria had told him about her going out tonight he couldn’t help but think back to his own team though. They were bound to have a party as well and while he could guess where and when it would be he had no actual clue about it having skipped going to the locker room entirely. It stung, not that he would have wanted to go out given his ck of socks or boxers to hide his lingerie. Plus with how the retionship with his friends had soured he didn’t really want to hand with them anyways. That didn’t make him feel any less excluded though, at least Valeria seemed head over heels with him again and her affection really did feel good despite the shame. He thought as he massaged her feet the way he knew she liked it best.

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