From Soccer to Sucker Pt.31

Chapter 39

It was somewhere in the middle of the night when Jake got woken up from a deep sleep by the sound of a door opening rather roughly, followed by the kicking off of heels and some brisk barefooted somewhat unsteady sounding paces. Jake's sleep groggy mind was very slow to process things however and as such it still came as a huge surprise to him when he was greeted with a sopping wet pussy coming down right onto his face to really wake him up. It went accompanied by some light giggling from above as Valeria was apparently horny and impatient enough to start grinding a little nearly straight away. It didn't take long for Jake to realise what was happening and while he couldn't protest to begin with, he knew better than to do so anyways as he instead went straight to eating Valeria's pussy to the best of his abilities as her moans picked up loud and clear high above him.

Jake couldn't help but feel embarrassed over how thoroughly used he was getting once again, but then again this was a lot better than the majority of his day had been. The rejection from the team and wearing that maid's uniform had been way worse. Hell he wasn't even wearing panties or stockings right now for a change which in and of its own was a real win in his book. Even the fact that it once again gave him big trouble with his cage wasn't the worst thing as he knew he was quickly earning points to the best relief ever. It might be just a blowjob instead of the pussy he used to get on a daily basis, but after weeks of nothing but embarrassing hand jobs a blowjob sounded like a dream. He thought as he dutifully ate Valeria's pussy to four consecutive orgasms until she finally collapsed off of him, too overstimulated to take any more.

Valeria needed a few minutes to recuperate enough from her sheer orgasmic high as she lay there catching her breath next to a very sexually frustrated and wet faced Jake, the difference between them couldn't be any larger, but Jake knew that he could do nothing about that. Nothing other than to earn more points that was. His arousal for that matter only climbed as once recuperated, Valeria hugged him tightly from behind, apparently having stripped out of her dress along the way as he could feel her bare breasts press into his back. The only thing she seemed to be wearing where stocking as she pushed a nylon clad leg between his legs, pulling him even closer and really locking him into the little spoon position, her pussy pressing into his smooth butt cheeks. A hand reached over Jake's chest to play with his nipples and while he smelled of pussy, it was very clear that Valeria was a little tipsy, smelling of alcohol instead as she started kissing his neck which soon escalated to some sucking as she left behind a hickey with a loud giggle.

"Mmm, you are the best toy a girl could wish for my sweet pretty Jane. Self cleaning and no hassle with needing to be charged or batteries for that matter, besides that tongue of yours can go for ages or have you simply not ran out of power yet. Hmm I wonder what I would have to do if that tongue of yours fell without power. Do you have a secret charging port after all, maybe a slot to push some power cell into? I guess I would have to find out if my toy ever fell without power cause I would get awfully frustrated awfully quick I imagine and I don't like being frustrated. I'm sure I can find some holes to stuff something into to see if it works or not." Valeria chuckled tipsily as ran a finger through his butt crack, dangerously poking his hole while Jake let out a mortified surprised squeal making her laugh all the harder. He for one never wanted to find out what Valeria planned to try if his tongue started failing. If that were the case it would be out of sheer exhaustion and nothing stuffed anywhere would fix that except for maybe some food in his mouth, but mainly he would need rest. He doubted that sensible logic would stop Valeria from trying though, but luckily she quickly dropped the joke and went on another tipsy ramble instead.

"I had a great time back at the club tonight, but it wasn't the same without you my sweet little Jane. I haven't been able to stop thinking about my sexy pretty sissy maid back home. Some of your friends actually tried hitting on me, they called you a loser if I remember correctly, telling me I shouldn't have to settle for a loser. I told them to fuck right off though my sweet Jane, and if they ever called you that again that they could expect a slap in the face. You're the best boyfriend I could wish for." Valeria whispered into his ear only to giggle again as she gave his nipple a slight pinch, but soon her grip on them loosened as she quickly fell asleep leaving Jake with very mixed feelings, still locked tightly into her arms.

A little more open due to the alcohol Valeria was very genuine and honest. It was mortifying that his friends had called him a loser to his girlfriend's face. Hell usually they wouldn't interfere if he even just mentioned he would try with a specific girl, yet now they were actively trying to steal his actual girlfriend, his first committed relationship away from him. Sure he wasn't committed by choice and he had often wished that Valeria would lose interest so everything could go back to normal, but the utter disrespect from those he had considered friends stung. It really proved that things might be beyond repair at this point. Hell he doubted he could even go back to being the player he once was. He doubted he could find the confidence again after all that had happened and in a way he didn't even know if he wanted this relationship to end anymore.

For all Valeria had put him through his heart warmed with joy hearing how she had stood up to his friends, calling him her perfect boyfriend and even threatening to hit them over it. After all the spankings he had gotten he didn't even doubt that she was capable of slapping him across the face, or that it was an idle threat from her part. The idea of it happening after all their harsh words actually brought a smirk to his face as he imagined Valeria slapping his old friends. Deep down he knew he should be able to stand up for himself, but he was more than happy that Valeria stood up for him. Sure he wanted more freedom again, but not at the cost of turning Valeria cold towards him once again. Despite the trouble it created with his cage it felt great to sleep with her again, to be tightly embraced. It made him feel safe and loved as Jake slowly drifted off to sleep again despite the shame he had suffered at Valeria's hands.

Chapter 40

It was rather late in the morning when Valeria finally woke up, still holding Jake tightly. He had woken up a while ago, not nearly as tired as Valeria had been having gone to bed relatively early. Jake hadn't wanted to wake her up however so instead he had laid awake for what felt like ages. Horny, frustrated with his cage giving him plenty of trouble in Valeria's warm embrace. It gave him plenty of time to think over what Valeria had said last night, yet the mixed feelings remained strong. With how his relationship with his friends had soured he needed Valeria more than ever, but no longer fighting what she was doing to him made him feel like an even bigger sissy than he already was and yet he felt loved and good with her as well. A feeling which only got highlighted when the first thing she did after waking up with a soft groan was kissing his neck again.

"Mmm good morning babe, my head hurts a little, could you be so nice as to get showered, dressed as my pretty maid and bring me breakfast in bed, and maybe an aspirin to go with it. That would be really nice right about now. Oh and don't you worry, I'll keep your breakfast warm and wet underneath the sheets." Valeria groaned only to end with a slight chuckle, in a great mood despite her headache. An orgasm would also definitely help to dull the pain, and while she could have just pushed Jake down under the sheets, she really wanted to be served by her sissy maid, just loving everything about that arrangement. The quick "Yes Miss Valeria" that followed was simply music to her ears, and just like that Jake left the bed, leaving her to turn around and close her eyes for a few brief moments longer.

Jake for his part rushed to the bathroom with a bright red face, kind of encrusted by the juices Valeria had left behind when she had sat on it when coming home. With that he was quite happy to get himself cleaned up. He was way less happy about getting back in that sissy maid's uniform though, Although he guessed it would earn him a nice chunk of points towards his next orgasm again. Despite the huge amount of points he now had to gather he was already looking at a next orgasm possibly tomorrow already. In that regard he didn't really have to fear going longer between orgasms due to this punishment, but there were more things he had to abide by to get them which was just what Valeria wanted. Either he would go deeper into sissyhood, or face very long periods of frustrations.

It took Jake a little while to get clean and into the outfit he had washed last night, and a little while longer to get a simple breakfast ready, but eventually he made it back over to Valeria's bedside with a nice breakfast and an aspirin, his heels clicking loudly throughout the dorm room. A night without heels had given his sore feet and calves a good rest, but now that he was right back into the very same shoes which had caused the aches, he could feel that his feet hadn't fully recovered yet. At least he was already a bit more well adapted to walking in them now that he had worn them for a couple of hours the day before. "Here you go Miss Valeria, your breakfast. Would you like me to go down for mine now?" He dutifully asked, blushing fiercely as he did, especially when Valeria couldn't help but giggle at his submissiveness, simply loving it to bits. It only further drove home Jake's embarrassment, but still this was a lot better than Valeria's previous cold attitude towards him.

He couldn't help but feel taken by surprise when instead of ordering him to go down on her straight away, she hooked a finger into his collar and pulled him towards her for an intimate kiss, nearly making him fall as he had to bow rather deep on these impractically tall heels. "Mmmm, now you may my sweet sissy Jane, shame on you, you hadn't given me my morning kiss yet, but then again I'm happy to see how hungry you are for my pussy. Thank you for breakfast by the way, yours is warm wet and waiting for you as promised." Valeria giggled as she took in his look now that he was back in his uniform, making her all the more aroused, her pussy leaking in anticipation of the great pleasure his tongue was about to provide her. Jake wasn't wearing makeup, and his hair was a bit of a mess again as he clearly hadn't properly brushed it out, but she could take care of that after breakfast and after he had satisfied her. Otherwise she would simply ruin the look straight away as she really needed that tongue of his right now.

For a good long while and a couple of orgasms Valeria enjoyed Jake's tongue while she had breakfast and her aspirin. She happily kept Jake down underneath her sheet until the Aspirin did its work, relieving her headache while his tongue relieved her arousal. Despite paying the price for last night's drinking this morning was turning out to be a perfect morning for Valeria. She didn't bother to tell Jake to stop once she had had enough, instead she just threw the sheets off of the both of them and got up, stepping away from his pussy soaked face in nothing but last night's stockings. It got an instant groan out of Jake as he struggled with his cage. "Mmm, that was wonderful Jane. Now please be a good sissy maid and change my sheets. Oh and do open a window, this room reeks. Once you're done you can gather my laundry and do the dishes. I'll be taking a shower in the meantime." Valeria casually said as she walked off to the bathroom while Jake scrambled to get back up on his high heel clad feet.

While Valeria went on to have a relaxing shower, getting cleaned up for a lazy Sunday at home enjoying her sissy maid to the fullest, Jake rushed to get all his tasks done before she would be getting out of the shower. It was embarrassing to realise how easily he was yielding to this new role, but then again it was a role he had been doing for a while now, the only difference was that he now had an embarrassing uniform to go with the role. The heels did make things a little more complicated, but in the end Jake was still faster at doing these things than he used to be having had plenty of practice by now. He was just in the process of drying the last dishes when Valeria returned to the her room wearing an elegant black silk bathrobe while her damp hair hung loosely behind her back.

Upon passing by him, Valeria just couldn't resist the urge to give him a playful smack on his petticoat protected ass, giggling as she did. "Good job Jane, such a good pretty sissy maid. Once you're done here you may come kneel before me. I would love to do your hair and makeup again if you'll let me. Of course there are some more points in it for you, that goes without saying. Hell at this rate you might find some oral relief of your own come tomorrow evening." Valeria spoke as she gathered her brush a ribbon and her makeup kit while he finished with the last dishes.

Jake wasn't exactly thrilled about wearing makeup again or having his hair done up once more for that matter, but it would earn some good points, that much was definitely true and he really wanted those points. Especially now that Valeria had enthusiastically hinted that he might actually be getting a blowjob for his next orgasm it would fell great after such a long time of only handjobs. Besides he reasoned that makeup or not, his hair done up or not, he looked like a complete sissy anyways so he might as well just submit to those things as well, it would make him look more or less as a sissy he told himself as he knelt in front of Valeria the way he had done so often while she sat on the side of her bed.

Wasting no time Valeria wiped his face clean, then got started on his hair, looking down at her obedient sissy on the floor with love and lust in her eyes. She so loved seeing how obedient he had become as she looked straight into his eyes, chuckling a little at how uncomfortable it seemed to make Jake who tried to avoid her gaze. Whenever he tried to turn his head away, she quickly corrected it with a gentle grip on his chin as she started brushing his hair out, taking her sweet time before putting it in a ponytail. With his hair just how she wanted it, she applied the makeup just the way she had done it the day before.

Ashamed as he was meeting Valeria's eye was hard, but in a sense it was also endearing the way she smiled down on him. It wasn't just a taunting sneer, but an actual genuinely affectionate smile. Plus he had to admit that the brush going over his scalp time and time again did feel kind of great, like a little head massage of sorts. The makeup brushes didn't feel quite as great, but not unpleasant either, what they did to his face however that was another matter entirely. Still Valeria would have to look in it more than he did, and it wasn't like he would be going outside like this so no one would see him. If this look made Valeria happy then he guessed it was worth it.

"There we go Jane, you're looking pretty as ever once again. Mmm you're getting me all worked up again. I have a nice tasty surprise for you. So go ahead and unwrap it, come on!" Valeria cheerfully spoke, pointing down at the rope holding her bathrobe together, already looking forward to seeing his reaction. It was one last thing she had bought along with this outfit and she couldn't wait to put it to good use. Right now was a perfect time for it, especially since she had had an opportunity to wrap it up perfectly. She had been thinking about the best way to give Jake this surprise and she quite liked this method.

Jake couldn't help but wonder why Valeria had bothered doing his makeup when she planned to use his face for pleasure once more anyways. All the work she had put into it would be ruined, but he guessed it was better not to question it as he pulled at the rope, untying the bow, fully expecting to be eating Valeria's pussy once again. He wasn't expecting a surprise and most definitely not the one he got. The moment the rope came loose, a very realistic looking rubber cock matching Valeria's skin tone perfectly fell down through the now open middle of her bathrobe. She had tied it up against her stomach with the rope of her bathrobe, hiding it perfectly until right now with gravity doing its work. She couldn't help but giggle as she saw the look of pure shocked surprise on Jake's prettily made up face. It was just perfect and well worth the wait. She just hoped the would actually get Jake to suck on it like she wanted so soon after making a big leap and getting him into that maid's uniform. The dildo made some bold claims regarding transferring pleasure and she wanted to see if it was true. The quick squeeze she had given it in the bathroom had definitely been promising.

"Well Jane, what are you waiting for? Show it some love, my toys among one another." Valeria giggled, wiggling her hips a little which made the cock sway almost naturally mere inches from Jake's shocked face. He couldn't believe what he was seeing and he couldn't believe Valeria actually wanted him to suck it. The mere thought of it was enough to make him shudder. Yet despite how disturbed he felt, Jake didn't dare jump up and walk away. Not that that would be so easy in his high heels to begin with. The fact that he even looked like someone who sucked cock made it feel all the more damning to Jake. He knew full well that he should be up in arms over this, yet he sat there a while longer in shocked silence while Valeria continued to wag her cock in his face. He might not be doing what Valeria was saying like usual, but her grip on him was so strong that even now he didn't manage to make a firm stance.

"Uhm Miss Valeria, thank you for the surprise, but this is really making me uncomfortable and I beg you to allow me to take care of your needs the way I've always done up until now." Jake blurted out when he eventually got over the shock enough to speak up. He instantly hated how weak he sounded, but after weeks of Valeria's continued manipulations, now on his knees in one of the frilliest dresses he had ever seen, with a freshly made up face and a cock struggling in his cage, he just couldn't manage to really stand up to Valeria and it made him feel like even more of a sissy. Still this was the biggest protest he had given her since putting on this dress and if Valeria's reaction to him refusing to put that dress on had been anything to go off of, he was even afraid of what she would say now, but he couldn't just let this happen, he wasn't a cock sucker.

"Oh come on Jane, don't be such a pussy, you can't honestly expect me to ever suck your cock if you won't suck mine can you? Besides this one is only silicone, and it's just about the same size as yours. Look I'm going to be honest with you. I don't really like the idea of sucking cock, but given your commitment to our relationship that is something I would be willing to do for you because I love you and because I see you're as serious about us as I am. I have never sucked a cock before though, and honestly I don't have the faintest clue on how to go about it which is why I bought this thing. I guess you have plenty of experience with cock sucking, I bet you can't even count the number of blowjobs you've gotten in your life. Some probably better I bet you have to be somewhat of a expert, having seen and felt plenty of examples. I bet you can show me just how you like it. So come on Jane, teach me how I should suck your cock once you've earned it. Do the both of us a favour my pretty sissy maid." Valeria spoke down as she thrust her hips forward just a little, moving her dildo that much closer to a cringing Jake's face.

He felt utterly mortified and shocked. The dildo did in fact look to be roughly the same size as his cock was, a good seven inches although it was hard to tell as he hadn't gotten a proper look at his own cock in what felt like ages. Still It was a scary intimidating size, especially from this perspective, while having to think of how to suck it. He couldn't believe Valeria had never given a blowjob, then again maybe he could given how head strong she was turning down all the guys who had hit on her. He wanted to propose that if she wanted to learn watching some porn might be better, but he feared that might offend Valeria. Eventually he just resorted for what he felt had the best chance and would spell the least trouble. "I could uhm maybe give you some pointers instead once I've earned a blowjob from you. Either way I'm sure that you'll do great Miss Valeria, just the sheer feeling of your mouth and tongue, the fact that you would be doing such a thing for me, will make it amazing." He gushed out trying to praise his way out of this situation. It wasn't even a lie, horny as he was, he wouldn't need that much and a warm wet mouth would be so much better than just a hand which had been giving him his only orgasms as of late. The thought alone was making him grunt as his cage gave him trouble once more, even when faced with this super realistic looking dildo.

"So let me get this straight Jane, you are refusing to suck my cock for me, to show me what you love. Instead you want to order me around when I go to the trouble of going down on you, you want to criticize my actions, and now you are saying that you expect me to do a lousy job but that it will be alright for you? Besides just judging from those grunts I would guess someone is very excited to be sucking my cock." Valeria spoke sternly with a raise eyebrow, loving the look of panic that instantly crossed Jake's face. Oh how she loved this control she had over him, getting him on edge, trying to avoid simply saying no while she was putting him in such a compromising situation. She hadn't expected him to just suck this dildo, in fact she had doubted that she would even manage to get him to suck it at all, but apparently she had even more control over him than she had thought after that week long cold shoulder treatment. She was actually starting to feel as though she might succeed.

"I... Uhm no Miss Valeria, I would never, I was just... I'm sorry Miss Valeria. Sucking on that dildo is just... Well..." He stammered, not really knowing what to say or do, but fearing he had messed up. He wasn't excited about this at all, or was he, one thing was for sure, his cock did try to get hard in the cage, but then again, dildo or no dildo, Valeria looked hot. One thing he was certain of was that he was feeling so awkward stumbling over his own words that he was in half a mind to just wrap his lips around that dildo and get it over with, to make it up to Valeria, to diffuse her sudden sternness. Meek obedience was pretty much becoming his go to response to make Valeria happy. It always seemed to work, just giving in to each and every one of Valeria's wishes, but this one, just looking at that very life like dildo made him reluctant to follow through this once.

"Hush now Jane, there's no need for excuses, just be a good sissy and suck my cock, it won't bite I promise you. Why don't you give it a kiss first and go from there? That would look hot don't you think? Do you like it when someone does that for you? Plus those prettily painted lips are just begging to kiss something. Here let me help you." Valeria said as she gently grabbed a hold of the ponytail she had put his hair in and guided her lips forward a little until the tip of her dildo was resting against Jake's lips. She could see his shame and reluctance, but he wasn't fighting or resisting her in the slightest. Valeria didn't hold onto his ponytail particularly hard, or shoved that thing forward, it was more like a slow gentle guidance leaving him plenty of time to pull away had he wanted, but even the slightest form of charge she took seemed to be enough to get him to comply. With the dildo against his lips, Jake simply gave in, giving it a kiss like Valeria had asked for.

"Mmm, you're doing a great job babe, that does look hot. Now why don't you open those lips of yours just a little and let me push a little bit further? Just look up here, I think I've picked up somewhere that guys love it when you look up in their eyes and seeing you on your knees I can definitely see the appeal." Valeria spoke, biting her bottom lip while getting all worked up, this really was hot and she was loving every minute of it, the sheer power of it was intoxicating, having a cock of her own to use while Jake was all dressed up and made up like a pretty sissy, the school's biggest womanizer and jock about to suck her dildo. With her order she gently pushed the dildo a little harder against his lips.

Down on his knees Jake was still facing the same reluctance as before. He really didn't want to be sucking on anything remotely phallic dress like he was, let alone on such a life like cock sticking from someone's crotch. Everything from the look to the position made it feel so much more real and devastating. It had been enough to allow him to refuse doing as Valeria told him, enough to say so, but not enough to firmly put his foot down and now that Valeria had taken a hold of him, he simply couldn't find it within himself to actually fight it. Instead he resigned to the fact that this was happening even if it felt like he could easily break out of Valeria's grip. She would probably just grab a firmer hold if he tried, he reasoned, more so to come to terms with the fact that he was actually about to suck a very life like dildo than because he actually believed it. Even the feel against his lips was all too real, it was easy enough to feel and smell that it wasn't an actual cock, but it still felt worryingly life like to him.

Having already kissed it, the step to opening his lips to it was considerably smaller, and as Valeria told him to, he actually did open his lips only to be rewarded by the dildo pushing past them and into his mouth. The fact that Valeria seemed to be loving every minute of this only made him have more mixed feelings. He really did want to please her, but this was so devastatingly embarrassing, everything about this situation was, but still he didn't fight it, he just let Valeria push it in deeper, realising that he was well and truly submitting to her. He might have liked to hold on to his masculine identity, but he was feeling more like a sissy than ever before as Valeria kept feeding more of that dildo into his mouth right until it was a little over half way in and pushing against the back of his throat making him gag violently.

Valeria couldn't help but giggle a little, but she instantly pulled out a little, only to release his ponytail with still a few inches of her dildo hanging in his mouth. "I'm sorry babe, I guess I got a little carried away there, but I guess I did learn something, not to take a cock that deep without proper practice. In any case, why don't you continue on your own pace and show me how you like it best?" Valeria laughed as she looked down into Jake's mortified eyes, eagerly awaiting his reply as he looked up at her with the dildo still partially in his mouth. It was picture perfect.