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Chapter 28
“Alright princess, you can stop hiding under mommy’s skirt now. Why don’t you go and make yourself pretty? Put on some panties and stockings for me will you? You can put on your bed time panties though, I don’t mind.” Valeria spoke with a smirk as she looked down, unable to keep herself from chuckling when Jake pulled his sopping wet face out from under her skirt, he may have just showered, but once again he was smelling like her pussy. She couldn’t make him anymore literally pussy-whipped if she tried. This was great, and it only got better when Jake actually scurried off to his closet to put on the panties and stockings she asked him to wear.
Jake on the other hand was just pin embarrassed about it all, but he wasn’t going to lose out his chance for an orgasm and probably set himself back a great deal of points by refusing. He had been wearing stockings and panties all the time, and the white satin panties were nowhere near as horrible as the frilly colourful thongs were. It was kind of scary how normal the idea of wearing them seemed to him, so much so that thinking about refusing to wear them for just a hand job didn’t even really occur to him. Sliding on the white satin panties, and even more so with the sheer bck stockings he opted to wear, Jake couldn’t help but feel his aching cock throb in its cage in response to the tantalising feelings of the delicate fabrics on his smooth skin. Any concerns about how these fabrics were seemingly affecting him more and more were quickly pushed back by the simple assumption that it was because he was way too horny having gone without an orgasm longer than ever. That while constantly being reminded of sex by the way Valeria used him.
“There we go, that’s so much better already. Now why don’t you get down on the bed so we can get started.” Valeria grinned as she proceeded to pull her cuffs from her bag and dangled them out to show Jake exactly how it was going to be. Given the video Valeria had shown him st time, he doubted that those cuffs were really necessary. There was no way he was going to refuse putting that cage back on with the threat of that video being made public hanging over his head. He simply couldn’t afford it, not with how low his image had already sunken. If that video ever came out his whole reputation would be permanently be destroyed. There was no way his friends were ever going to accept that with how the idea that he had some fun submissive kinky thing going with Valeria was already cause for plenty of ridicule and jokes. Luckily they could at least seem to accept that on some level.
Whether it was necessary or not didn’t really matter though, he knew full well that he couldn’t just say no to Valeria due to the same threat plus right now the way more direct threat of losing out on his much needed relief. If Valeria wanted to use those cuffs then he would have no choice but to let her so with a sigh Jake got down on the bed only to let out a surprised yelp as Valeria nearly instantly jumped him, straddling his chest only to pin his hands above his head and pce an aggressive kiss on his lips for over a minute before she finally pulled back. “Mmm, fuck Jake, you’re so hot when your obedient you know that?” She asked rhetorically as she looked into his eyes with lust. Jake might not like being submissive, but getting to dominate him sure turned Valeria on more than she had ever imagined. The more comfortable she got with herself in this role the bigger the turn on seemed to get.
Although Jake wasn’t really submissive, there was something incredibly hot about the wild, somewhat scary lust filled look in Valeria’s eyes as she looked down on him keeping his hands pinned above him while her luscious brown hair fell down at both sides of her head, framing his face in the process as it created an illusion of being in a very small intimate pce with her. He was unable to see anything but her smiling face as she licked her own juices from her lips. There was definitely nothing prudish about her now, if anything he would describe her as ravishing, scary but oh so sexy. It made his cock strain hard within his cage, hard enough for him to groan in pain which only made Valeria chuckle.
Then before he could even react, she scooted forward and sat her sopping wet pussy right down on his face, pnting her legs onto his biceps. “Now lets get this show under way so we can finally release that poor cock of yours from that cage shall we babe? I mean you clearly need it if that’s how you react to a simple kiss you overly horny sissy.” Valeria teased as she proceeded to cuff his hands to the headboard of his bed. When Valeria had jumped up to kiss him, he could have easily thrown him off. With her legs pinning his biceps and her weight onto his face it would have been way harder, but with the cuffs locked in pce it became impossible as she found himself completely at Valeria’s mercy once more. Now he couldn’t even stand up for himself if he wanted to, and it only became worse as she got off of his face only to cuff his ankles to the bed as well.
“There we go, all nice and secure.” Valeria grinned giving one of his restraints a firm tug as if to test whether her statement held true. Now pleased that Jake couldn’t do much more than wiggle around a little she started stripping, not bothering to go out of her way to be sexy. She simply pulled off her dress, her bra, and kicked off her shoes. Nevertheless it got more than a few groans out of Jake as her nice tight body and perfect breasts came into full view when she was left wearing nothing but stockings. Aroused as he already was the sexy sight only added fuel to the fire.
Smirking widely Valeria proceeded to pnt her foot high up on Jakes chest. “You know the drill babe, if you want to cum, you have to kiss the key and ask me nicely to unlock your for a quick handjob. It isn’t because you’ve earned your orgasm that you no longer need to be polite about it.” Valeria smirked, clearly enjoying herself way too much with this while Jake didn’t like the slight smell or the feel of her damp warm nylon cd foot on his chest at all. It was not only slightly gross, but also just pin embarrassing to him.
Nevertheless Jake gave in without much hesitation at all as he pnted that kiss on Valeria’s feet. It was hard to tell why he even did it, was it because he really was craving that relief so much? Was it because he wanted that foot away from his face? Was it because refusing was pretty much pointless? Or was it because he was growing so used to doing whatever Valeria ordered him to do? It hardly mattered as he simply did it. “Miss Valeria, could you please unlock my cock and give me one of your amazing quick handjobs?” He asked horny enough to y it on thick as Valeria couldn’t help but chuckle in reply.
“Of course Babe, because you asked so nicely. I didn’t know you thought my handjobs were amazing though, but I guess for a sissy any type of attention to their clitty is amazing right?” She chuckled as she leaned forward to take off her anklet with the key, keeping her foot pnted on his chest as she just loved the way he blushed in response to her teasing. Then without further ado she hoped back onto his face, squirming a little until she was nice and comfortable with pussy directly over his mouth, then leaned forward to take off the pretty pink chastity cage. She didn’t even mind the confrontation with his cock which instantly jumped out to greet her, growing into a full erection rapidly.
“Oh my, turns out you weren’t lying at all. You look incredibly excited about my handjobs. I’ve never seen a cock rise this fast except for maybe the st time I offer you a handjob that is.” Valeria chuckled, just driving his shame in deeper as she grabbed two more accessories she had brough along, gloves to be more precise, one in satin and the other in nylon to lend her the full flexibility of her hands while definitely upping the sensation of her teasing game. Plus she figured it could train Jake to react even stronger to the sensations his new lingerie brought him. Her excitement only further fuelled by that Idea Valeria went to work with a big smile on her face, gently stroking her gloved hands over his torso, from his nipples all the way down to his nylon cd knees over his inner thighs and back.
She was incredibly pleased to feel Jake squirm underneath her. She could swear she had even felt what she thought was a moan muffled by her pussy covering his mouth, and that straight off the bat. This was going great. Her efforts from st times, paired with the fact that his arousal was higher than ever having been denied and teased for so long were clearly having a good effect on what she was trying to accomplish. It only made Valeria more excited, her pussy growing wetter on his face as she spoke up. “By the way sissy it isn’t because I’m working to make you cum that you should ignore my pussy which I’ve so graciously offered to you. You aren’t cumming before I do. Look at it as a couples goal, a mutual orgasm, and since you’re orgasms are so much more rare than mine we have to grab that chance now that it presents itself.” Valeria spoke with a big grin as she continued her gentle teasing, letting out a satisfied moan as she could feel Jake’s tongue wiggle its way back up her pussy like that of the obedient sissy he was rapidly becoming.
Stuck underneath Valeria Jake couldn’t believe this was happening. He couldn’t believe how effective the gentle caresses of those gloved hands he had never seen coming were, but they most definitely did things to him. They made his cock throb violently, especially when that nylon glove ran across his nylon cd inner thigh. The feeling was simply intense, intense and embarrassing. He couldn’t believe he was actually getting off on just some delicate fabrics like the ones of his lingerie rubbing across his body. What guy got off on that? He couldn’t help but worry, and the fact that Valeria’s occasional rubbing of his nipples felt nearly as intense as those inner thigh strokes did nothing to help him feel better about what he was getting off on. If anything it all helped him feel like an even bigger sissy and for as much as he wanted and needed that relief, he wanted this embarrassing ordeal to be over with even more. It was why he gave Valeria’s pussy his all like he had done multiple times now. It was unbelievable, amazing oral, in exchange for an embarrassing handjob, but that was the best he could hope for at the moment. It was either this, or total denial which was not something he could deal with going off the pressure in his balls.
Valeria had never thought she would ever like seeing Jake’s cock let alone touch it, but here she was, actually excited to give Jake his orgasm. If she was honest, she was probably even more excited about giving Jake his orgasm than he himself was. Seeing him react so intensely to all of her touches while she was in full control and getting all the attention she could want was incredibly hot and fascinating. Just like Jake was learning what spots to hit while eating her out, Valeria was rapidly learning what spots to touch got the most intense reaction out of him. Touching his nipples seemed to work best with the satin, while his thighs definitely got the biggest reaction out of the nylon glove. It wasn’t all too long before she had his cock twisting and leaking, his moans pretty much constant and hers didn’t stay out for all that long either.
By the time Valeria was approaching her orgasm Jake had been on edge for over a minute, the intense sensations of Valeria’s touches getting him incredibly worked up, but just short of being enough to actually get him off. That all changed however when Valeria tipped over the edge, squirting down on his face out of sheer excitement only to directly touch his cock for the first time during what was supposed to be a handjob. She didn’t grip it hard at all. She just closed her satin covered hand around it, touching it ever so lightly on all sides while her nylon gloved hand continued stroking his inner thigh. Three light strokes with her hand like that were enough to tip Jake over the edge as he once again ended up cumming all over his stomach in what was a rather violent orgasm.
Due to the intense shame of how he had just came, Jake came down from his orgasmic high faster than Valeria did. He couldn’t help but feel mortified by how easily he had came with barely any touches to his cock at all. Hell now that the post orgasm crity hit him he could hardly believe how eager he had been not to miss out on this. It was horrible, but there was no way of taking it back, and tied down with Valeria still sitting on his face there was nothing he could say or do about it but wait until she released him. Even his release wasn’t going to bring much relief however as before Valeria even attempted to get up, she took it upon herself to lock his now limp cock back up in it’s cage that had pretty much been it’s prison for what felt like an eternity. Even with all the orgasms he had had since Valeria had locked his cock up, her sheer avoidance of actually touching his cock when she helped him get off resulted in less strokes than even a one orgasm jerk off sessions would have given him in the past when he could still jerk off, not that that was needed much with his sexual prowess.
“Phew, that was fun! And you have been quite well-behaved ever since we had that serious talk. Who knows if you keep being that good we might even have to talk about taking our retionship to the next level, maybe do something more than just a quick handjob. You still have a long way to go before you get anywhere close to my pussy though. Even if you do earn that privilege I might have to look into finding a third, a real cock, cause honestly babe, that one pump chump isn’t going to please anyone.” Valeria smirked as she slowly started to put her dress back on. Unable to stop herself from rubbing in her accomplishments. While she had initially intended to just take him down a few pegs, his over infted ego being in a huge need of some trimming, embarrassing Jake and making him feel like a sissy was just too much fun.
When Jake appeared to want to give her a reply she quickly interrupted him. “I know technically there were three pumps, I have to give you that, but I didn’t exactly grip you hard. My pussy would grip that cock of yours way harder.” Valeria countered a potential argument before it had even formed. She knew she hadn’t exactly been fair, denying him for a long time, and working him up like that. It basically forced him into that premature orgasm once she finally touched his cock, but she didn’t really care about being fair and considering all the facts. It was incredibly successful at making Jake swallow his words as his wet face just turned beet red.
As much as Jake had wanted to point out that it wasn’t fair, that he usually had way better endurance, his embarrassment shut him down completely. The fact that it was near constant, having sapped away a lot of his confidence over time, didn’t do him any favours. Valeria’s facts were undeniable he had came from three strokes and a rather light grip and the fact that having his nipples toyed with or his nylon legs caressed had worked him up so much wasn’t really an argument he wanted to bring up. Having been denied too long was probably the argument he was most comfortable using, but even that was weak as it hadn’t been that long, only two days. So he just shut up instead, patiently waiting for Valeria to untie him.
“Now before I untie you I want to hear a big thank you for pying with your sissy clitty and helping you make cummies. Use those exact terms or you’ll start of on minus ten rather than the point you just earned getting me off again.” Valeria grinned with a big smile. With his post orgasmic crity in full swing and his shame looking more intense than before the handjob she had given him, she couldn’t help but want to double down on it. Hell she loved it so much that she nearly felt the urge to jump onto his face again.
After all the shame he had just suffered that was about the st thing Jake wanted to say yet with his face sopping wet from Valeria’s multiple orgasms and a substantial pool of his cum ying on his stomach, he fully realised it was his only way out of his current position. Freshly relieved he couldn’t care less about the points, but he did fear the spanking that would follow if he reached minus ten. It was more than he could handle after everything that had happened so Jake ended up reluctantly giving in. “Thank you Miss for pying with my sissy clitty and helping me make cummies.” He said absolutely mortified as his face turned an even deeper shade of red.
“There’s a good boy.” Valeria chuckled as she gave him a degrading pat on the head only to carry on. “Now while you did earn this orgasm, I have to say I’m a little disappointed. The only reason you earned it was because I was horny and not at all because you have become more attentive. I think I was just a little too easy on you and honestly that’s on me, so for your next orgasm you’ll need twenty points to earn it. Maybe that will help. In any case I’m going out tonight, if you want to join feel free, if not then I don’t want you to wash your face, something to keep me with you through the night.” Valeria expined as she quickly gathered her cuffs back up finally releasing a shocked Jake from his bed.
“See you ter babe, have a good night no matter what you decide.” Valeria chuckled as she gathered her things reset the counter to one and walked straight out of the room not allowing Jake the chance to give her much of a reply at all. She simply didn’t care about what excuses he might have for her. Her rules were her rules and she wasn’t going to change them no matter what Jake said it was one of the perks of holding all the cards. She was already curious to see what influence her new goal would have for Jake, would he start showing some more initiative?
Although Jake wasn’t all too worried about those points just yet, it did sting that he would have to work twice as hard now just to relive this incredibly embarrassing experience. He had no doubts that his next orgasm would be made just as bad as this one had been, mentally that was, cause although he was ashamed to admit it for as embarrassing as it had been, this st orgasm had been one of the most intense ones of his life so far. The denial and all the build up had made sure of that. Luckily that was something Valeria couldn’t know or he was sure she would have teased him mercilessly about it. Or rather she would have yet another thing to tease him mercilessly about as she had plenty of ammunition when it came to that.
Already resigning to his fate Jake got up from the bed with a deep sigh to clean the cum off his stomach. He badly wanted to clean Valeria’s pussy from his face as well, but he knew he couldn’t, not unless he wanted to find himself subjected to a spanking and needing to earn thirty more point until his next orgasm. The only reason he could have to clean her scent off his face was to go out with her and there was no way in hell he was going to do that. The st thing he wanted right now was to make a public appearance, with or without Valeria. He guessed that since she would be going out she wouldn’t notice him having cleaned off his face, but after her previous surprise visit in the middle of the night he didn’t want to take that chance, after all she had said she would see him ter and it worried him.
With nothing better to do than to try and put his shame out of his mind before going for an early night, Jake slid under the covers with his ptop to watch some series. The silk of his new bed covers sliding over his smooth skin and nylon cd legs was enough to make him shudder, almost reminding him of Valeria’s soft caressing touches by the way it slid over him. He couldn’t help but worry slightly what sleeping in them all night would do for his caged cock, that or the constant strong scent of Valeria’s pussy, but like it or not, he was stuck dealing with it as he tried his hardest to just forget until he went to sleep.
Chapter 29
The following morning Jake woke up with a loud groan. His cage was giving him trouble once again as his morning erection tried to form only to be denied by the unyielding metal. In the meantime he was surprisingly horny again considering he had just came the evening before. It was probably to be bmed on the rather vivid dream he had had, one where Valeria was sitting on his face and constantly caressing his body in the most sensual ways, never even once touching his cock. A dream that was certainly to be bmed on the strong scent of her pussy that stayed with him even now and the feeling of his silk sheets all over his body. Even his dream had been an embarrassment yet one with an undeniable to him shameful effect of turning him on. What the hell was wrong with him to even have sex dreams of literally being treated like a sissy underneath Valeria rather than ones where he was with one of his hot conquests.
Not even wanting to let his mind go there Jake got out of bed and went out to the shower, gathering his clean dry lingerie only to put his night time lingerie by the sink for washing. Pretty much everywhere he went he was reminded of his new sissy life and it was devastating. At least Valeria hadn’t shown up in the middle of the night again, although now that he thought about it, that meant he shouldn’t have had to keep the smell of her pussy onto his face. She would have never noticed if he had washed his face the day before. Still it had been a risk he hadn’t been able to take at that moment, which didn’t make him feel like any less of a fool.
Sighing deeply he hopped into the shower only to be confronted by another horrible choice. His regur bodywash and shampoo was right there, but so was Valeria’s and most dreadfully so was her conditioner which she insisted he used from now on. He really didn’t want to, especially seeing how it was pretty much the st step in getting washed and how it reeked of flowers, a scent he would be able to wash away with his own product anymore. Then again he really did believe Valeria when she said she would notice if he hadn’t used it, and he really didn’t want to find out the consequences. So for the umpteenth time Jake yielded to Valeria’s will and showered only to finish by using her conditioner creating an awkward mix of smells of his own bodywash and shampoo, with a strong hint of sweet flowers. Awkward as it was, he guessed it was better than the all over powering smell of Valeria’s products combined which only seemed to enhance one another. Still he was anything but thrilled to head to css with even a hint of flowers hanging around him.
After cleaning his night time lingerie and hanging it up to dry, keeping his bathroom looking nice and feminine, Jake walked back out in his room to get dressed for css. He didn’t care much for which thong he picked out of his drawer, nding on a pastel yellow one, after all they were all terribly colourful and frilly. What he was more picky about however were the stockings he was supposed to wear. They were all terrible, but the mat nude ones were avaible again so he ended up going for those. After all it was the st day of css for the week and he guessed that during the weekend except for the game on Saturday he could just keep to himself in his dorm room leaving today as the st big chance to get his secret discovered. The most subtle stockings were bad enough already for the occasion he figured as she carefully rolled them up his legs, trying hard not to damage them, this was a pair he really didn’t want to lose out on.
Subtle or not Jake Still couldn’t help but feel like a fool, once again as he stood there in nothing but frilly lingerie, the stockings although pretty much invisible on his skin were still very noticeable with the tops on dispy, or the toes for that matter. The sheer material did nothing to hide his vender painted toenails at all. It made him more than happy to cover it all up with a pair of his regur socks, pants and underwear. Only when he was absolutely certain that not a shred of his lingerie was on dispy did he leave his dorm out to his first css, dreading a confrontation with his friends after how he had left them in the locker room the day before. There were sure to be many questions and he didn’t feel like answering them at all. In fact he dreaded the confrontation so much that for a brief moment he considered trying to avoid them altogether, but he knew that wasn’t an option. If anything avoiding them would only make things worse as being stuck in plenty of csses with some of them and only so much room there was no way he could successfully avoid them for long. So with a heavy heart and some mild arousal as his pants brushed over his nylon cd legs, Jake headed off to css.
Much like he had feared he was instantly bombarded with questions as to why he had refused to get changed in the locker room with them before and after practice as he met up with his friends. When he refused to answer they bombarded him with their theories of what he hadn’t wanted them to see. Theories that basically boiled down to a collection of marks left behind by spankings, floggings, ropes or canings. Given how Valeria had in fact spanked him already it was mortifying to listen to as he couldn’t help but think back to that moment and shudder. Nevertheless he just kept on repeating that he didn’t want to talk about it simply because he didn’t want to get into trouble with another lie, and telling the truth was definitely out of the question.
It resulted in his friends calling him out for being no fun at all, but they did eventually drop the questions much to Jake’s relief. Then again, it hadn’t exactly made his standing with his friends any better as they talked about the party they had gone to st night and how epic it had been. A subject he couldn’t even talk about. All Jake could do was sit by awkwardly and realise that he was completely out of the loop when it came to the social life of he and his friends.
It was painful to hear about that party, especially since he hadn’t even been invited. He hadn’t known about it. Then again he had painstakingly avoided his phone, but as he checked, he realised that there had been no invite anywhere in his phone to begin with. Could he really bme them though? He had shot down all their previous attempts to invite him along to a party, besides they probably hadn’t really texted about it to begin with. The party had probably just been arranged when everyone had been gathered in the locker room. Everyone except for him that was. It wasn’t like he would have went even if he had known, but it did sting not to get an invite from his friends. He was almost happy when the prof started his lecture so their talk about that stupid party came to a slow end.
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