From Soccer to Sucker Pt.30

Chapter 38

Jake was left to massage Valeria's feet for way longer than he usually did. It was degrading to relax her feet while his suffered so much because of those damn heels. Nevertheless he was pleased that Valeria allowed him to massage her feet for so long, cause it meant a longer rest for his own feet, something Valeria luckily also granted him when it came to giving her her backrub. Rather than making him stand behind her like she often did, she went ahead and laid down on the bed for him as she stripped completely naked, chuckling softly as it got a groan out of Jake, his caged cock obviously struggling with the sexy sight. "Alright Jane, why don't you pick up that rose scented massage oil and give my back your best. You can sit on my ass if you wish, in fact I would quite like that, a perfect position to get to all of my back." Valeria mused as she simply closed her eyes and prepared to fully relax.

Giving massages like that had always been something Jake loved giving as foreplay. It was just so hot, sensual and intimate, yet now he dreaded doing it beyond believe. It still sounded incredible, but with his cage already giving him this much trouble he really wanted to avoid doing anything that might turn him on too much. Something which sadly seemed impossible around Valeria, and even more embarrassing in this outfit with all its sensual sensations. Still with his feet still aching he guessed it was better to do it like this than to have to stand behind her as all he managed to say was a meek. "Yes Miss Valeria."

Without delay Jake got up on his heels, getting an instant reminder that it would indeed be better to sit, even if it was on Valeria's ass which was doomed to be terrible for his locked up cock. With the rudimentary mince he had been taught to use to keep his balance in these heels, he went to fetch the rose scented massage oil and minced straight over to the bed where he hesitated slightly to get down, groaning at the mere thought of doing so. The sight was amazing. Still he knew he probably shouldn't wait too long and he really wanted to get off of these heels as well, so deciding to bite the bullet Jake climbed on, planting one of his stocking clad knees on either side of Valeria's hips before slowly sinking down to get seated. It went accompanies by plenty of grunts especially when he could feel his cage hanging out of the front of his panties make direct contact with Valeria's soft warm ass. It was killing him inside. His cock was so close to where he wanted it to be, yet so far removed at the same time. It only got worse as he fell into a series of pained grunts when Valeria took it upon herself to start shaking her ass below him a little bit.

Under any other circumstance he would have loved this and even encouraged Valeria, but now he just squirted some oil on her back while hoping she would stop as he started firmly working on Valeria's shoulder muscles, leading to a delighted moan on her part. Valeria loved just about every aspect of this, but above all else she loved the feeling of that hard metal cage on her butt cheeks and the way they caused Jake to grunt and groan in discomfort. In the past she would have given him a slap across his face if he had ever dared dance up to her, but now she was rubbing her naked ass right against his nearly exposed cock and she was loving every minute of it. it was especially thrilling to know she could demand him to get between her legs in an instant to relieve her own arousal while still denying him. In fact she was getting so worked up that she might actually need to do that at some point, but for now she just wanted to keep enjoying her back massage to the fullest as Jake's strong touch felt amazing.

The entirety of the back massage was one big torment for Jake's caged cock to the point where he was starting to doubt whether this was really preferable to standing on his sore feet. He knew better than to let that get to him and slack off though, if he did this would only get dragged out even longer and he really wanted to keep this as short as possible as Valeria occasionally kept shaking her bottom against his caged cock, loving the grunts it brought each and every time. After about twenty minutes she finally decided to let him go though, not because she wanted, but because she still had to eat and get ready for a party. For as fun as this was, she was running out of time. Now that Jake had finally given in she was in half a mind to cancel tonight's party, but in the end she decided not to. Tomorrow neither of them had anything to do so she could have all the fun she wanted then. "Alright Jane, that's enough. You may stop now and get started on dinner. I do have a party to get to after all. If you want to you are welcome to tag along of course, but right now I think I'll just relax some more. That massage was great as always, laying down you really manage to get all that tension out so much better, we should do it more often." Valeria casually moaned out as she remained on her stomach with her eyes closed, barely containing a chuckle as Jake got off right away, trying to get away from her naked ass as fast as he possibly could. It was hilarious considering how he must have dreamed about touching back there for ages.

"Yes Miss, right away, and thank you for the invite, but I still have a lot of chores to do so I think I'll pass." He replied feeling utterly pathetic. It was another thing he had never thought would ever happen to him, that he would reject an invite to a party, much less one with a ton of hot women, like a whole team of them, especially not with the excuse of having to do chores. They weren't even his own chores and the fact that he was dressed as some kind of sissy maid only made it feel that much worse. Hell now that he thought about it he would probably be washing the sport socks of the women he could have gone partying with while they had fun together. Still that was exactly what had just happened. For as mortifying as the idea was, it didn't even compare to how scary the thought of going out in public with Valeria was what if her teasing started to become a little too on the nose, what if her friends found out the exact kind of relationship they had? Then soon all his friends would know as well. Now they just thought it was something kinky, something which probably not nearly as bad as this. The idea of anyone seeing him like this was one of the scariest things Jake could imagined, all dressed up and made up like a sissy. It was enough to make him shudder for real.

Of course it was to be expected. Valeria hadn't thought he wanted to go to a part considering his late tendency to pretty much avoid everyone. She loved that he was using his chores to get out of it though. It was hilarious. One of these days she was definitely going to make him tag along with her, but for now she was happy just allowing him to grow a little more comfortable in his new role as her sissy maid. After all it had been quite the leap no matter how one looked at it and she didn't want all that she had built start to crumble by over pushing it. So far she had done a great job sissifying more and more of his life without any too large protests. "That's alright Jane. I can imagine a maid's job is never done, and you are making such a good sissy maid. Still I wanted to ask, because I love having you around." That last bit wasn't even a lie. Butterflies were going wild in her stomach every time she saw Jake and thought about the hold she had on him. Just like her arousal was going crazy over the same thing. If she was ever going to grow tired of this it certainly wasn't any time soon. If anything she was only starting to love it more and more the more ground she won with his continued sissification.

With another shameful "Thank you Miss" Jake went back to work, painfully aware of the loud clicking of his heels and the soreness in his feet and calves. Still he remained glad to be off that gorgeous ass for how it was tormenting his caged cock. Not that it was helping a great deal, cause his stockings brushing over one another and the petticoats brushing over them were still plenty of reason for his cock to try to grow hard in that cage much to his shame. At least standing still in the kitchen as he went about preparing their dinner like he had pretty much been doing every day to earn those points. He used to be a lazy cook, only preparing the easiest things he could imagine and often just popping something into the oven, having a shake, or ordering take out. Ever since he had started cooking for Valeria however he had certainly been learning.

It took him a little over thirty minutes to get a fresh meal on the table he had set while cooking, only to mince over to the bed where Valeria was still laying naked, on her back by now, her breasts and pussy on full display giving rise to another grunt on his part. "Miss, I just wanted to let you know our meal is ready." He spoke, with a bright red face underneath all that makeup. Although he had basically been acting as a maid of sorts for days it felt so much worse now that he was actually dressed like one. Before he could still kind of convince himself that he was just a boyfriend doing something for his girlfriend, but now he really felt like he sissy maid.

"Mmm, thank you very much Jane. You're being a very good maid today. That attitude of yours has really had a major adjustment with just a change of outfit. Hmmm. I love you so very much Jane, you really do make the cutest maid I've ever seen, and good cute maids get rewards. Keep this up and you'll be earning a reward in no time, you know that special kind you love so much." Valeria moaned as she got up from the bed only to pull him down by his collar and plant a kiss right on his painted lips, no longer making an effort to reach up to him which would have been more than necessary now that she made him wear those tall heels. While she kissed her free hand reached down under his short skirt to fondle his caged cock through the hole in his panties, only to break the kiss with a giggle as he started grunting in discomfort.

"I'm glad to hear you are liking being my sissy maid just as much as I am. I told you this was a great investment in our relationship, it sounds like that outfit is just as big a turn on to the both of us, why I could swear that back when you were massaging my back you were even growing wet like a girl. Now let's eat shall we?" Valeria giggled referring to a wet spot she had felt which she swore could only have been because his caged cock had started leaking. She knew his outfit wasn't the only cause for that, but the way she had been training him to respond to all those sensual materials was definitely paying off and she couldn't help but rub in how he seemed to love that dress with every chance she got. Making him look like a sissy was one thing, making him feel like one was working rather well, but making him believe he was nothing but a sissy who should be glad to have such a gorgeous girlfriend now that was real power and would only make him even more obedient and willing to do more for her. With that said she simply kept her finger hooked into his collar to casually lead him off to the table where she finally released him and Jake was all too glad to just take a seat to give his feet some more rest. Some real rest rather than veiled by an embarrassing chore just to get out of standing up. It felt weird to feel the chair's padding on his naked cheeks through the back hole in his panties, but with his skirt so short and him just plopping down it was inevitable.

"No no no Jane, that's not how you sit, especially not when wearing a skirt. You really need to be more careful and take your outfit in account when you move. Now get up again and as you sit down make sure to swipe your hands underneath your butt. Also unless you plan to show everyone your pretty panties I advise you to keep those knees and ankles of yours neatly pressed together." Valeria scolded him, feeling highly amused to see him comply immediately. His obedience was a real delight. Jake for his part just didn't want to screw up over something so silly. After putting on that outfit just sitting down in a specific manner was nothing, although it did make him feel even more effeminate bringing a bright blush to his painted cheeks. One thing he did agree on however was that he didn't want those panties to be on display at all, not even when it was in front of Valeria, so he made sure to keep his legs together, his bare ass now resting on his petticoats rather than the seat. There was such a stack of them that it felt like sitting on a small pillow.

Aside from that small scolding their meal resumed as normal. Feeling constantly embarrassed Jake had grown a lot more quiet, but Valeria had no issues filling that silence. Between bites she praised his meal, his looks, talked about her day and dropped more than a few hints regarding how she was looking forward to him earning their next orgasm, and stepping up their sex life. The majority of the topics were nothing but embarrassing to him, yet at the same time for some reason they also felt great. It was all praise and enthusiasm and given Valeria's cold treatment from the past week, or the fact that his old buddies had been giving him nothing but a hard time he hadn't been getting much of that at all. Plus for what it was worth he was also really looking forward to stepping up their sex life and earning himself that blowjob. For as embarrassing as it was to wear this maid's outfit he guessed it was worth it. After all it made Valeria very happy and she was the only one seeing them.

"Alright Jane, today has been amazing in a big part thanks to you, but it was high time I started getting ready now. So be a good sissy maid and do the dishes will you? Oh and don't even think about taking off those heels. I want to hear them click. Besides you really need the practice. You're doing a lot better already, but you're not quite there yet." Valeria chuckled as she got up only to plant a kiss on Jake's lips, loving the grunt she got when he got another full up close look at her naked body. With that she simply walked off. She was incredibly horny once more, but she wanted to preserve that precious makeup she had painted on his face until she was about ready to leave. Which wasn't long anymore and in a sense an extra motivation to hurry along into the bathroom for a shower.

Jake for his part was in no hurry whatsoever, the night was plenty of long for him to get all chores done and still have time to spare. The biggest one by far was doing the girls team laundry, but he had gotten better at that with practice so it didn't take as much time as it initially did anymore. Besides these dorm rooms weren't all that large so there wasn't a lot to clean. Plus unlike other times there would be no Valeria to distract him by making him get down on his knees ever so often like he had gotten quite used to doing. Aside from the outfit, this was nothing that he hadn't done what felt like a million times by now. Still he knew he shouldn't delay either, cause the sooner he could get this done, the sooner he could get out of this outfit and back to his place to lick his wounds. While it was a huge relief that all was well with Valeria again, this had all been incredibly intense and something he was glad to get a break from. With that in mind he gathered the plates, mincing on his heels and turned to do the dishes.

His cleaning was briefly interrupted by Valeria emerging from the bathroom and walking past him, giving him a playful slap on his skirt clad ass. "Mmm so fucking cute. You're doing well Jane." She chuckled as she headed to her closet to select her outfit for the night leaving him behind with flushed cheeks yet again, just when the shame was becoming a little less intense as he was getting used to being alone. Soon he would really be alone he guessed and while that was a good prospect, one where he would finally be getting a bit of a break where at least no one, not even Valeria would be witnessing his embarrassing outfit. He guessed he could always take it off after she had left, but he was already discarding that idea from before it had fully emerged. After all Valeria did seem to have a knack for finding out if he didn't do what he was told, like when she had caught him not wearing panties to bed, or in all his boasts and lies to his friends. What if she forgot something and returned? Or decided to make a pitstop between locations? No it would be best if he just put up with this outfit for as long as she demanded it. It was the safest bet.

By the time he finished up doing the dishes and turned around Jake was instantly met by the gorgeous sight of Valeria in nothing but a sexy lacy green and black bra, smoothing a pair of sheer black stockings up her legs. It was a sight that made his cock grow, or at least try to which led to a near instant grunt on his part alerting Valeria that he was done with his chore. "I know right? it's hot to see someone put on a pair of stockings right? I just love seeing you smooth a pair up your pretty legs as well." Valeria giggled as she continued with some extra show, getting a few more grunts out of him in the process. Like she often did by now to grant him easy access wherever she planned to make him eat her out, she skipped wearing panties. It was a naughty secret he would have loved to know about a date with a hot girl, and when she was fully dressed and made up Valeria did look spectacularly hot. Right now it caused him nothing but more shame though, knowing why exactly that Valeria wasn't wearing panties. Still he wasn't even going out with her, he had chosen chores as a sissy maid above a party with a stunning looking Valeria. Why she neglected to wear panties now when he wouldn't be around to pleasure her anyways was beyond him, and although he didn't want to admit it, he felt a slight tinge of jealousy creep in, imagining she might use that freedom some other way, or worse with someone else. Jumping from one girl to the next he had never felt jealous before, but with Valeria it was different. His life had really started to revolved around her.

"Alright Jane, you've gotten some time to enjoy the show. Now be a good sissy maid and go kneel next to my shoe rack. You can grab my black pumps, I'll be there in a moment, just need to grab and check my purse." Valeria waved him away, just loving how infatuated he was becoming with her. She had always known he thought she was hot, and while this was nothing like the relationship he would have wanted, it was clearly growing on him. She knew it was bad to manipulate him like this, but it was for the greater good she reminded herself. There had been a lot less heart broken girls since Jake had been put under her thumb, but of course she also just loved having him there. With a big smile and her purse in hand she walked to her small hall right up to her kneeling sissy. Her heart fluttering with joy ass he saw him sitting there, so pretty and obedient. This was most definitely awesome. Valeria simply couldn't help but test out his obedience as she didn't say a thing, instead just holding out one of her nylon clad feet. Given her previous instructions it didn't take a genius to figure out what she wanted and so Jake obediently slid on one of her pumps, followed by the other as she extended that foot.

"Mmm, there's a good sissy. Now why don't you give me a big satisfying goodbye kiss so I can get going." Valeria chuckled as rather than leaning down or beckoning Jake to get up, she simply raised her skirt an revealed her cleanly trimmed, bare pussy to him, right at eye level. This part didn't even surprise or shock Jake anymore. Valeria had put him in a position like this one time and time again. Eating her pussy was one of his most frequent chores. It no longer even warranted any hesitation at all despite him feeling rather mortified with the entire situation. He just leaned in and started pleasuring her the best he possibly could which was great by now. He had gotten more than enough practice after all. Still it did warrant some grunts as his cage was growing awfully tight again.

Valeria for her part was in heaven, just throwing her head back to enjoy the delightful sensations of his tongue. She just threw her head back, and for the first time grabbed him by the base of his ponytail. It felt great to have such a pretty handle to hold onto and she really hoped that Jake would continue to agree with the makeup and hair. A shiver of pure delight coursed through her body as she imagined how smeared his makeup was now becoming. It only made her press his face harder into her pussy. She guessed he would keep on agreeing with wearing makeup every time he wore this outfit, but if not the she was sure to make it a requirement in time.

In the end Valeria kept his head in place until she had had not one, but two more orgasms, after which she finally took a step back and started catching her breath, her skirt finally dropping back down over her pussy. "Mmm, that was delightful Jane, what a kiss. You've gotten so great at eating pussy. I doubt I'll ever find a better cunt muncher than you." Valeria mused with a chuckle as she looked down at the result of her orgasms. It looked hilarious. Jake's face was sopping wet, his makeup, most of all the mascara completely run out. He really did look like a back alley hooker, although the outfit definitely told a different story. It still looked as sweet and sissy as when he had first put it on. She absolutely loved it, everything about this look told only one story, how she completely owned him and it almost made her go in for another round.

"Now be good when I'm gone. No taking off that delicious outfit until you are ready to go to bed. My bed. I really want you to stay the night Jane. You can bet that cute pantied ass of yours that I'll be horny thinking about you cleaning up my place while I'm out partying. So I'll definitely be able to make use of that tongue of yours when I get back. I so love the idea of having myself an obedient sissy waiting in my bed. Of course I do know that you have no panties laying around here, so I guess for one you can sleep naked as I really want you to wash that lingerie before you head to bed so it's fresh and clean for you to wear tomorrow. Oh and if you are done with your chores and feel like it, please do feel free to experiment with my makeup a little. I would be very pleased to see that face of yours repaired a little. Even if you do a very poor job of it. In any case. That's about it Jane. Have a nice evening and I see you later." Valeria happily instructed before simply turning on her heels and walking out of the door, leaving Jake behind, horny, wet faced and stunned, not even giving him the time to form a reply before shutting the door behind her, looking forward to what was bound to be a great victory celebration with a great end diving in bed with her sissy. She doubted he would experiment with makeup, like she had suggested, but just merely planting that seed into his head filled her with great joy. She so loved toying with her sissy creating, and she couldn't wait to teach him makeup for real. All in due time though, she had pushed him enough for now.

Still down on his knees Jake slowly got up. He had wanted nothing more than to just do his chores and go home to finally have some peace and quiet in his relative safe space. Although he guessed with all the pink touches Valeria had snuck in there, it wasn't as safe a space as it used to be anymore. It no longer felt like it was fully his anymore as Valeria dominated his dorm room as well. All in all he guessed he should just be lucky that he could sleep naked for a change, without the panties Valeria usually demanded he wear. It was a small consolation though considering how he was basically bound to get woken up in the middle of the night just to eat pussy, or worse how he was going to end up in this exact outfit again tomorrow with how Valeria had specifically instructed him to make sure to wash the lingerie. With a deep sigh, he just gave into his fate and marched into the bathroom to get started on the girls team laundry like he had done so often by now.

As he was washing a pair of thick pink grass stained sweaty soccer sock, he couldn't help but imagine that Valeria was currently talking to the girl who had worn them. He was involuntarily picking up the awful scent of her feet before he managed to plunge it into the water he had prepared. Right now she probably looked great, dressed to the nines and ready for a party just like Valeria. Most girls on her team were very hot, and he knew what almost all of them looked like naked. His train of thoughts made him grunt as his cock tried to grow hard yet again. His arousal was really proving to be a real downwards spiral, the hornier he got, the more his mind drifted to sexy thoughts and the more bothersome and frustrating his cage became. It was almost painful, but he quickly reminded himself that he was well on his way to earning the points he needed to get a blowjob from Valeria. Plus he was pleasing her which also made him kind of feel good in an odd way.

All those things didn't make his heels more manageable though they kept giving quite painful feet and calves, but Jake kept them on anyways. He didn't even know if it was born out a fear of disappointing Valeria, or a genuine desire to please her, but the end result stayed the same. He dutifully washed the girls teams laundry, dressed like full fledged maid, unable to keep himself from shuddering a little every time he looked up too much. After all the sink was sitting in front of a mirror which gave him a good look at his tied back hair, whorishly ruined makeup, his collar and the top of his outfit. It was a painful reminder of just how big a sissy he was, especially doing the task he did now, but luckily there was no one there to see him. Plus Valeria seemed to love him more than ever dressed like this.

He was nevertheless very glad to get this chore over with and move on to the next one, feeling like more of a maid than ever, his heels giving him more trouble than the cleaning did by now, but he managed. Chore after chore he cleaned up Valeria's apartment just the way she liked it, only to finally move back into that bathroom where he dutifully folded up the freshly washed and now dried uniforms, putting them in the bag ready for Valeria to take with her, only to finally strip out of his outfit and wash his own way more elaborate lingerie.

Putting his heels flat on the ground felt strange to him by now, strange, but like heaven nevertheless, finally his feet and calves were given the rest they had so desperately been craving. He guessed it also meant he could take off this ruined makeup, or take out his ponytail which he didn't hesitate to do. Finally he was feeling more like his old self again, but looking in the mirror as he washed his very frilly and delicate lingerie, Jake couldn't help but feel embarrassed anyways. His hairless chest and that pink collar with his sissy name on it, didn't look manly at all, and then he couldn't even see the chastity cage yet. Hanging up his delicate stocking or mortifyingly frilly and open panties up to dry wasn't doing him any favours regarding making him feel better about himself either. The fact that this was what he considered close to his old self was saying a lot. Either way it was finally time for him to head to Valeria's bed, and try to catch some sleep before he would be woken up rudely once more.