From Soccer to Sucker Pt.32

Chapter 41

On his knees with a way too realistic dildo in his mouth Jake didn't have to think very long about what to do. After what had just happened he didn't even consider pulling off of Valeria's cock to be an option. The way he saw it, it was either decide his own pace or have Valeria take charge again, and with her trying to push too far, doing it himself was definitely the safest bet. That didn't stop it from feeling deeply embarrassing though as he slid his painted lips back down the shaft, as deep as he could somewhat comfortably take it, before going back up to the tip and down again.

As he was sucking on that dildo Jake didn't know if this was really better. It certainly was less uncomfortable not having that dildo forced in too deep, but at the same time, actually actively sucking cock on his own felt so much more embarrassing than just giving in to Valeria's forceful hand. Giving in to Valeria he could at least dissociated from the action a little, but now it was he who needed to take action. Valeria on the other hand really seemed to love the view down between her legs, his head bobbing up and down her cock. So much that she was even moaning over it, almost like she could actually feel what he was doing, which was in fact somewhat the case. She might not be able to feel the subtleties of Jake's mouth and tongue, but she could most definitely feel the bulb inside of her swell and shrink as his lips massaged the shaft. It felt amazing, especially paired with the power she felt seeing those lips go up and down that shaft, really enhancing the sensation.

"Mmmm you're doing such a good job sissy. I never really got why guys seem to enjoy blowjobs so much, but this feels and looks absolutely amazing. I have to be honest, I was a little sceptical about this dildo transferring actual feelings from the shaft to my pussy, but it works so much better than I could have dared hoped for. Hell I might actually orgasm from this. Tell you what my sweet little Jane, if you can give me an orgasm sucking my cock you get another five points. Either way you are helping yourself out big time, cause I'm learning a whole lot from you sucking on my cock." Valeria cooed, shocking Jake who couldn't believe she could in fact feel it. Not only that, but she also wanted an orgasm out of this. It made this horrid blowjob feel all the more real to him as he was no longer just sucking on some dildo, he was effectively sucking Valeria off.

If anything it only made things more embarrassing, but that didn't stop Jake from continuing. He had gotten this far so he might as well grab his points for the effort he had already put in. Five points were a lot for him after all. Besides he still wasn't sure if he could even quit. If he tried then would Valeria demand he'd continue anyways? Would she take back control and make things more uncomfortable? He was so far under her thumb that he didn't even really consider quitting without her express permission, no matter how embarrassing it got. He pretty much just resigned to his fate, the way he had been taught to do with Valeria now that he had gotten over the first hurdle of getting started.

Valeria for her part was extremely pleased with herself and most of all her project which was Jake. She could see the shame and the reluctance in his eyes, but he kept on bobbing his head up and down her silicone cock. It was a very telling sign of just how far down the sissy rabbit hole she had managed to push him. It had taken a little bit of force at first for sure, but now that he was going he kept going and she was definitely planning on making this a regular thing. Valeria couldn't help but shudder a loud moan escaping her lips as a surge of pleasure coursed through her, the sensations, the view, the feelings of control and accomplishment paired with future plans, plans which seemed more promising than ever coursing through her head, all coming together to make her feel amazing.

Despite how thrilled Valeria was feeling, getting her off only through sucking on that dildo still took quite some time, something Valeria didn't mind at all, but Jake was just hoping for it to be over with at every turn. It had made him feel so very odd to hear Valeria's moans rise, grow louder and more frequent while sucking on that hump of silicone, a hump which he simply couldn't stop identifying as a cock much to his shame. The feelings that this was all too real weren't helped at all when he ended up being caught completely off guard when Valeria finally did have her orgasm. Her whole body tensed up as her moans reached a climax and she threw her head back after looking down at him all this time. Valeria resisted the urge to grab back onto his ponytail and drive her cock as deep into his throat as she could. After all she did promise to let him go at his own pace. Jake on his end still ended up gagging and coughing around the cock as much to his shocked surprise it actually ejaculated into his mouth. It was clear that it had to be a result of Valeria's orgasm, and nothing but that as it tasted exactly like her pussy, which he had tasted more than enough to know by now. That and it actually coincided with how her body tensed in waves during her orgasm. Still that didn't negate the fact that this all too real cock had just came into his mouth.

Not really knowing what to do Jake just swallowed like he had done to plenty of Valeria's juices as he remained on his knees with her cock buried into his mouth. Just kind of keeping it there because he didn't know if he was allowed to pull off just yet. It took a few moments for Valeria to come down from her orgasmic high, which wasn't as explosive as the orgasms Jake provided directly with his tongue, but all things combined just as intense with the aspect of actually seeing him suck on her cock. Sitting back up right she couldn't help but giggle seeing him still holding her cock in his mouth. "Mmmm, that's wonderful babe, and so fucking hot, although I couldn't quite escape the feeling that it was a rather boring blowjob. I mean don't get me wrong, seeing your lips wrapped around my cock, and all was hot, but to me it looked like you were just bobbing up and down, plain an simple. I mean if that is how you like your cock sucked then I don't judge, but well I can imagine if I had had a real cock I would have loved to see some more passion and some different techniques. I also seem to remember about hearing guys talk on and on about the wonders of deep throating, and you only took a little more than half. Then again I'm no expert." Valeria said mildly criticising the blowjob she had just gotten only to see Jake's shame deepen even further. She couldn't help but love it.

Jake had to admit that as far as blowjobs went the one he had just given Valeria would rank near the lowest he would have ever received. It was plain boring that was definitely a right assessment, just some quick bobbing to get it over with. Having a partner who treated your fun as something to just get done with as soon as possible was horrible, but he didn't regret it at all as he was more than embarrassed enough having just gotten it over with. The last thing he wanted was to suck that cock like he loved it. He thought as Valeria grabbed the back of his ponytail and dragged him away from her cock. Jake couldn't help but notice the bright pink ring of lipstick formed around the shaft down at the deepest point he had been able to reach, about an inch past the half way mark. He couldn't hep but feel mortified seeing the very clear evidence of how he had sucked Valeria's cock. That and the almost as embarrassing evidence of how much makeup he was wearing for her. Trying to deep throat that cock would have been very difficult and he was glad he hadn't even tried, just like he was glad it was finally out of his mouth now, but that didn't help with the shame of it all one bit. He couldn't believe he really was dressed like a sissy only to have sucked cock like one as well.

"Don't you worry though Jane, you'll get a chance to do better later, but first let's go have a look in the mirror. Your makeup might be completely ruined, but I think it looks kind of cute." Valeria giggled, only to catch him completely off guard again when she clipped a matching leash to his collar and got up. She waited a few brief moments for Jake to get back onto his high heels as well, but after that she nearly instantly tugged him along to the mirror. It wasn't very far, or necessary at all to use this leash, but Valeria had wanted to lead him by a leash for a while now and it was every bit as good as she had imagined it to be, her very own devoted sissy pet, what was there not to love?

Jake for his part could think of countless of things not to love about his current situation as he couldn't help but feel deeply embarrassed getting led around by Valeria like this. It got even worse when he caught a glimpse of just how it looked when the neared the mirror. Valeria looked magnificent as always, sexy, yet scarier than ever. She hadn't bothered to close her bathrobe back up, giving him a great look at her breasts. At the same time it didn't cover her strapon either, leaving it on full display and bobbing around all to naturally in its permanent erect state, the lipstick mark all too clear as she casually strolled on bare feet. It made Jake tower over her in his tall heels, but with the leash leading down from his neck into her hand and the look of shame on his face compared with the amused confidence on Valeria's it was very clear who was in control here. He was barely in control of his own footing, still struggling with the very tall heels and he was completely over dressed in this way too frilly outfit.

When they finally approached the mirror Valeria pulled him out in front of her, making him see himself in his full sissy glory as she smirked. "See, I told you you looked incredibly cute. It's a pity we can't take little Jane out to play just yet." Valeria giggled as she flipped up the front of his skirt and started fondling his caged cock, driving her nails gently over his exposed balls in a way that made Jake shiver with pleasure only to end up groaning loudly as his cock tried to grow hard in response, the cage instantly punishing it which only caused Valeria to giggle more. It stung especially cause Valeria could actually take his cock out to play whenever she wished, that power was entirely hers, he could clearly see the key around her ankle, but he knew that wasn't going to happen. Instead he had to deal with his mirror image which was more awful than ever, a combination between a sissy and a back alley hooker. The outfit screaming sissy while his face screamed whore. That deepthroat attempt from earlier when Valeria had been in control had brought tears to his eyes making his mascara run, and the dildo had done a good job at smearing his lipstick completely. He wouldn't really describe it as cute, but he did understand Valeria's excitement. He had to admit he always loved when a girl looked ravaged after they had had a wild time. Now he was the girl and Valeria had the cock much to his shame.

"I particularly love the eyes Jane, the lips are definitely fun as well knowing why they look that way, but I'm a sucker for kissable lips and you do like kissing me don't you babe?" Valeria asked innocently, a tone which told him that there was something coming he probably wouldn't like. Then again what was the worst it could be? Surely this outfit and sucking on that horribly realistic dildo were way worse, he thought as he answered with a near standard simpering. "Yes Miss." Which made Valeria smile big time. At least that was something, at least Valeria was truly enjoying herself.

"Good, I'm glad we're on the same page Jane. Now since I can't take care of those pretty lips of yours every time I want to kiss you, that will be your job from now on. Don't worry, I'll teach you, but then I expect you to keep your lips pretty and kissable at all times where you are acting as my sissy maid Jane, after all it shouldn't only be my maid's duty to make my dorm room look as good as possible at all times, my maid should also put effort into making herself look as pretty as possible at all times. Now stay right here a second, I'll be back shortly." Valeria eagerly exclaimed before rushing off as Jake could only groan, it looked like he would really need to learn how to use makeup after all, or at least lipstick that was.

When Valeria returned a few brief moments later she was carrying a box of tissues and the tube of bubble-gum pink lipstick, the same one she had used on his lips a little earlier this morning. "Alright Jane look closely, I'm going to show you how to use this, then it is your turn." Valeria spoke loving the squirmy embarrassed look in his eyes as he turned his attention towards her. With that Valeria slowly and carefully started applying the lipstick, smoothly tracing it over her upper and lower lips before smacking them together to smooth the lipstick out. It lead to some uncomfortable groaning on Jake's part as seeing her put on that lipstick was awfully sexy, giving his cock a hard time in that infernal cage. At least he was earning good points now so he would soon find some relief from this cage, and way better relief than a mere handjob at that, so he guessed it was worth it. It was the best he could really hope for in his situation with Valeria as his only remaining friend.

"Now of course you will have to wipe your lips clean first, and if you're careful you can just wipe away small smudges around the edges, but if it's too smudged, it's best to just start over. Here have a go at it Jane, I think it's best if you look in the mirror for now, in time it becomes muscle memory, but even I tend to look in the mirror just to be sure it's nice and even." Valeria enthusiastically spoke as she shoved the lipstick and the box of tissues in his hands while Jake looked down on them a little uneasy. He didn't like the idea of wearing makeup, but he did so for Valeria, he liked it even less now that he was supposed to apply it himself, but in the end it was just a minor detail compared to his outfit and the cock he had just sucked, not worth the effort of protesting.

A little hesitantly Jake grabbed the lipstick and tissues. He was more than glad to wipe the smudged lipstick off, but not at all to apply a fresh coat. With Valeria watching closely however he didn't hesitate for very long. Utterly embarrassed he twisted the tube to force the pink stick out then touched it to his lips with a slightly opened mouth. He tried to gently brush it from the right to the left, then do it again from the left to the right on his bottom lip. It felt even weirder than when Valeria had applied it for him, especially to see himself doing it. With his racoon eyes and the outfit's frills hiding the majority of his most masculine features he might actually pass as a girl on first glance, an overly tall girl, but a girl none the less. A closer look would most definitely give him away as a sissy tough.

After he closed his lips and smacked them together like Valeria had shown he couldn't help but groan, he looked more like a clown than anything else. It was just a blob of pink in and around his lips in no particularly appealing shape. Valeria thought it was hilarious though as she laughed her ass off at him. "Aww poor Jane, you have to go a bit lighter on the corners of your mouth, your lips aren't as thick there as they are on the centre. They do look hilarious, but not kissable as my sissy's lips should be so try again." She giggled as she hugged him from behind, driving her dildo between his stocking clad legs as she carefully watched his second attempt, ready to give pointers where needed.

Jake did not like the feeling of that cock between his legs at all, but there was no getting it away unless he were to push Valeria away and he obviously couldn't do that, so instead he just focused on his own lips again. It looked so damning to perform such a sexy action while facing the mirror dressed like he was, yet Jake cleaned his lips and tried to reapply the lipstick to the best of his capabilities. It took multiple attempts, and multiple pointers by Valeria, but after trying for a while he did manage to apply his lipstick more or less to Valeria's satisfaction. It looked good, unless you looked really closely, but that was more than good enough for now. "Mmm, that's what I mean by kissable lips!" Valeria exclaimed enthusiastically, grabbing a hold of his leash and pulling him down for an immediate passionate kiss which lasted for a good while. It caught Jake by surprise, but he quickly surrendered, letting Valeria kiss him however she liked. Like with everything it was very clear who was in charge.

When she finally broke the kiss, she broke out in a hearty chuckle. "It looks like your lipstick is smeared Jane, fix that will you? I'll leave the tube and the tissues here by the mirror. In fact that is an order Jane, since you now know how to take care of your lips I want to see them kissable at all times, safe from some time after they got ruined of course to give a you a chance to touch them up. Outside that you can expect a spanking if I ever catch you with less than kissable lips, so I advice you to frequently check on them in the mirror like a good sissy. Now once you're done, I think it's about time you took care of our nails. You can join me at the table shortly." Valeria giggled as she left her stunned sissy maid alone in front of the mirror.

Mortified Jake couldn't help but hesitate a little, the idea of keeping his lips kissable at all times, touching them up frequently, and checking on them even more frequently, like some genuinely makeup addicted sissy sounded devastating to him. It was something he was forced to be so much more actively aware of than any other part of his outfit. Although the sensations of his outfit, and discomfort of his heels and cage also reminded him of his predicament at all times. Still Valeria had made herself very clear and he really didn't want to upset her, remembering full well how coldly he had been treated last time. He really wanted to avoid that from happening, so he wiped his lips clean yet again and carefully reapplied the way too pink lipstick. He felt like such a big sissy as he smacked his lips together to smooth it out, almost like throwing his mirror image a kiss.

One thing was for certain, he was glad to get away from that mirror, even if it meant going to Valeria to give the both of them a pedicure. He couldn't help but wonder what colour their nails would be now, and when he saw the bubble gum pink nail polish bottle in her hands he couldn't help but groan. It was a shade almost perfectly matching his currently lipstick. The way she was sitting there with that way too real looking dildo, still carrying his lipstick marks only made him feel even worse. Nevertheless Jake knelt down to get started on her nails like he had done once a week for a while now. Much to his surprise however Valeria stopped him in his tracks. "Hold on one second Jane, if you are going to be my maid, I really think you should learn some proper etiquette as well and to do so let us start with the basics, a curtesy. A good sissy and a good maid should both know how to curtesy so it goes without saying that it's double true for a sissy maid. Now that you can handle those heels moderately well I think you're ready to learn." Valeria informed him with a big smile.

Jake could feel his cheeks flush beet red at even the mere thought of performing a curtsy, but Valeria didn't seem to be bothered by it at all, just carrying with her instructions straight away. "Good so here is how you perform a proper curtsy. You place one foot behind the other, lift the hem of your skirt by pinching it between your thumb and index fingers, then lower your head and bow through your legs a little. Now give it a try!" Valeria instructed with a big smile, feeling her pussy clench around the large bulb of that strapless strapon in pure excitement. There was just something about a curtsy that got her so thrilled thinking about it, even more so when she actually saw it in practice as Jake clearly tried his best. It was very clumsy, but that didn't take away from the thrill. Here he was, the over confident jock, trying to curtsy for her in an overly frilly dress right after touching up his lipstick. She couldn't help but squeeze the shaft of her dildo, letting out a soft as the bulb inside her swelled and squeezed her clit just right, it felt so naughty, but amazing nonetheless.

Just like with the lipstick Valeria gave him some quick pointers to learn to curtsy just right as she had Jake trying again and again, giving her dildo a few more squeezes in the process, she just couldn't help herself. For Jake that made things extra horrible though, not only did he feel like a complete fool trying to perform a perfect dainty curtesy, he also couldn't help but notice how Valeria was practically masturbating to it, like actually jerking a cock. If she had been rubbing her pussy, or even been pounding it with a dildo or a vibrator he wouldn't have minded as much, but seeing her squeeze that all too life like cock which did give her pleasure, was just too odd and embarrassing, looking all too much like how a guy would be jerking off. It didn't even matter much that he knew it was fake, it somehow just made him feel all the more objectified.

"Mmm, that was hot Jane, and that curtsy was good enough, now as for how to properly use those curtsies. When I give an order a simple yes Miss with a curtsy before carrying it out will suffice. When you leave my presence a simple Miss with a curtsy will do nicely unless of course when you're going off to do something then you'll inform me about why you are leaving for a moment. If I give you something, even just a compliment, a thank you Miss, with once again a curtsy is in order. If you have a question you may ask Miss? With you've guessed it a curtsy. When you've come to do something for me not immediately following a command you inform me with a curtsy, asking me if it is still okay. Much like just now you've spend some more time before the mirror, touching up your makeup rather than coming right over for that pedicure so the correct thing to do would have been to ask. May I take care of your nails now Miss? With a curtsy the moment you arrived before me. I will be lenient at first, but if you keep messing up you will eventually find yourself over my lap again Jane. Now was all of that clear?" Valeria explained with big grin, looking expectantly at the sissified jock before her, giving the dildo between her legs another squeeze of pure excitement.

Standing there in his sissy maid's uniform Jake was shocked all over again, it would have been easier if Valeria had just told him when not to curtsy he imagined, then again she had just listed a whole new set of expectation on how to converse with one another, a way more formal way, treating him more like an actual maid than her boyfriend. It was embarrassing, yet also kind of good to see how thrilled and happy Valeria was. It was way better at least than seeing her cold and distance and it did make his heart leap a little bit as well for some odd reason. She had however been pushing things way passed his slowly ingrained instinct to just obey and yield. She was expecting so much that he now had to think on it, but all in all he guessed a curtsy wasn't the worst of the changes which had happened this weekend, so after thinking on it, he yielded again and simply dipped into a curtsy saying. "Yes Miss Valeria." He felt deeply embarrassed, yet good to see her smile grow even further. All in all she had been really kind and loving to him this weekend which had been exceedingly nice after the extremely lonely and hard week he had had.

"Great sissy, I'm glad to see you are learning. Now all this curtsying has made me kind of horny as I'm sure you've noticed. Don't think I haven't seen you ogling my cock throughout this fun new lesson. Why I would almost expect you were developing a taste for it, a preference even. Or is it that you just want another chance to show me what you like for that blowjob you seem to be well on your way to earn by tomorrow at this rate. I know last time was a bit of a false start, and I'm sure you want to do better so I can see what a proper blowjob is like. Either way, whatever the reason you were so hungrily eyeing my cock it's your lucky day Jane. I'm definitely in the mood for some relief again and those lips of yours look perfect to give it, so get down on your knees and suck me off will you? And don't forget about some certain new things you might have to do." Valeria spoke with a giggle as she opened her legs wide and wagged her cock a little. She was kind of curious about what he would do. Last time he had been kind of tricked into it, so this would be the first time he would get down on his knees just to suck on her lifelike dildo. Of course he had already sucked on it for quite some time so that should make it somewhat easier. She had gotten him past those first steps with a little force and now she wanted to solidify them as part of a new normal.

Jake for his part couldn't help but stand there shifting awkwardly on his high heels. He knew what was expected of him, but the mere thought of doing those things was awful. Yet he really didn't want to give up on that potential blowjob he was going to get and he knew very well that it solely depended on Valeria's discretion. She could make up her mind at any point and no matter how unfair he thought that was, it wouldn't change the fact that he would have his orgasm on her terms. Besides was it really worth it to upset Valeria, to risk ruining how happy, excited and loving she had been this weekend by refusing to do all kind of things he had already done anyways? Probably not, so he did the only thing he thought he could do and did as he was told. Despite telling himself that this was nothing he hadn't done before, Jake couldn't help but feel way more embarrassed about it as he actually dipped into a curtsy and said. "Yes Miss Valeria." Only to get down on his knees and after a little hesitation took that dildo back in his mouth.

Bobbing his head up and down while attempting to make it look a little sexier, Jake did remind himself that this was just a hunk of silicone in a certain shape, that this was just some naughty fun with a hot girl and that this didn't mean anything. Still no matter what he told himself, he couldn't help but feel like a sissy cock sucker, even if the view up was of Valeria looking down on him with lust filled eyes while playing with her perfect breasts. A view which sadly only gave him trouble with his own locked up cock which tried to grow hard in its cage. It was wildly unfair, he had been in the mood for some relief since yesterday, mere hours after his orgasm, yet he remained denied, while he was pretty much told to scratch Valeria's itch the moment it appeared.

Then again maybe this was what being in a relationship was like as despite everything he had started to care way more about Valeria than any girl he had ever been with. His flings had always been fun, but selfish, mainly catered towards his pleasure. Sure he prided himself on giving his dates orgasms, but maybe more for his own pride and conquest than their actual pleasure. Maybe it was a good thing he was in that cage so he could learn to focus on other's pleasure as well, like he guessed it should be in a long relationship. Jake thought as he kept on sucking that cock. The longer he was under Valeria's thumb and the more isolated he became the more he tried to rationalise his situation only to start relying further on Valeria who remained in full control.