From Soccer to Sucker Pt.48

Chapter 61

On Sunday morning Jake woke up to a series of soft kisses on the back of his neck as Valeria gently played with his nipples, while rubbing their nylon clad legs together. It made his attempted morning wood all the more ferocious, struggling hard to breakthrough which in the end only brought him more discomfort as the first thing out of his mouth was a loud groan. "Oh good morning babe, hope you slept well? I most certainly did, although I've grown a little overly horny from the dreams I had in case you couldn't tell. Although I guess that groan tells me I'm not the only one. In either case I could really use a big long morning kiss right about now." Valeria moaned into his ear as she gently pushed down on his head, pushing him all the way down under the sheets as Jake put up no resistance whatsoever. He just dutifully started eating Valeria's pussy like she clearly wanted him to as he had done so many morning before while Valeria in turn gasped in pleasure, loving that amazing tongue of his as much as she always did.

It was very clear that the time for him to get choose what they did was over once more and that Valeria was more than happy to take full charge again. Still while it was a little degrading to be used like this again without any kind of reciprocation Jake had to admit he was quite happy to be eating Valeria's pussy. For one hearing her moan and feeling her play with his hair was shamefully great, even this kind of affection meaning the world to him by now even if it was somewhat demeaning that Valeria was just using him for her pleasure. The affectionate playing with his hair showed that she loved him though. In either case and more importantly he was more than happy to eat Valeria's pussy as it was saving his ass for now. He was very happy to please her as much as she could handle in the hope that she would forget all about fucking him. True he might get off on it, and he could use some relief being shamefully worked up once more, but for now that need didn't outweigh his shame at all.

Once Valeria was finally fully satisfied and overstimulated even she just pushed him away as Jake got in the usual routine of making them breakfast. Valeria didn't even have to command it anymore, all she had to do was make her wishes known when Jake demurely asked what she would like to eat. He had gotten well and truly in the routine of serving his Mistress by now and he took pretty much every point he could get, hoping that now that he had proven that he would suck cock for her his next release from chastity could be for another blowjob, no shameful hand job, nothing up his ass, just a good old blowjob, or better yet maybe he would finally get to actually fuck Valeria, after all she had fucked him so he guessed he had proven that he would do the same for her. Then again hopeful as he was, there was no way he would dare bring that up especially not since he doubted he would last anywhere close to long enough to even get started on getting Valeria worked up. The idea that he would shoot his barely moments after putting it in was horrifying. So horrifying in fact that he was a little apprehensive of the thought of fucking her even. It was what he had desired for so long, and this was not the relationship he had envisioned having with her at all but now that he was closer than ever to potentially earning the privilege of fucking her he was scared, not knowing if he even dared do it, extremely self conscious about his premature ejaculation problem. He could already imagine the kind of mockery he would face if he came right after slipping it in and it was mortifying just thinking about it. It sure was one more reason not to actually bring it up himself.

If anything that whole realisation only made him feel like an even bigger sissy. That soon turned out to be the very least of his worries as after a shower together during which he had only gotten more worked up, and getting dressed in a fresh pair of stockings and a fresh thong. Valeria finally brought up what he had been dreading all this time, her strapon along with a whole new bomb. "Mmm this was an absolute perfect morning babe, I loved it! You really are getting the hang of this pampering thing and you know what? I think its finally time we did away with that whole score list. It was more like a guideline on how you should be treating me with a little incentive to begin with, but now you've clearly learned and I don't think that incentive is needed anymore. I absolutely love the turns our sex life have taken as of recently and from the amount of orgasms you've had it's incredibly clear that you have been loving it as well. We both love it, and I'm not going to deny myself something I love because you haven't earned an orgasm yet. Trust me when I tell you that going forward there will be plenty of orgasms in your future, I just can't resist that cute ass of yours which looks so much cuter with my cock buried deep inside. So I guess that kind of takes away the incentive part which doesn't mean you should slouch on the pampering. I can and I definitely will spank you if you do." Valeria warned as she sounded like she had just broken the greatest news ever.

To Jake it was nothing but horrifying though. His tasks wouldn't change, but the reward he got for completing enough of them would completely vanish. It sounded like he would never be let out of that cage of his again, that his only orgasm would come from getting fucked by Valeria which was both scary and terrifying. He felt bad enough as it was over cumming from getting his ass fucked, but for that to be his only form or relief? It was such a mortifying prospect that Jake couldn't let it pass, not without protest, he might be lacking in courage, especially when it came to standing up to Valeria, but what sounded like permanent chastity was way way too much for him. "Uhm Mistress, I don't mean to be a bother, but what about my cock? I won't deny that I get off on getting my ass played with, but my cock is really important to me as well, clearly I some sexy fun with my cock even more than I love getting my ass toyed with. Maybe we could do away with that chastity cage as well cause I really don't want to be locked up permanently Mistress, please." Jake argued even with what was at stake too cowardly to just call Valeria's new plan out too harshly, fearing to offend her and get in trouble. He couldn't help but feel a little doubtful over if it would work or not, but as he had been making the argument he had thought that there might even be a chance in it to get him out of chastity permanently which would be great even if it just meant he would get to masturbate again, severely lacking the confidence to break up with Valeria or pick up girls behind her back. He had been worked under her thumb so much that those thoughts didn't even occur to him.

"Hmmm I don't know Jane, I don't know if I can trust you. After all you lied to me about how much you loved it up the ass as recently as yesterday, and that while I was starting to feel like we could finally be completely honest with one another. Besides, let me ask you this, why do you even need your cock to be free from that cage? Like what do you plan to do with it? No sleeping around or jerking off to some nasty completely disrespectful porn I hope? The only reasons I ever played with your cock were for you, because I love you and didn't want to completely deny you orgasms. I don't like it all that much while toying with that ass of yours is something we both love, something for us as a couple to really bond over. Is the fun we have together not enough for you that you feel like you need to get out of that cage for whatever reason?" Valeria asked, acting like she was a little hurt by it. Although the idea of keeping Jake in permanent chastity was kind of fun, she didn't really care much for it. Unlike what she had said she had loved toying with his cock, literally holding his pleasure into her hands and getting him hooked on all kinds of fun things like further enforcing his response to the sensual feel of his lingerie because of it. It would be a pit to miss out on that, then again it would also be a pity not to leverage this opportunity to have even more fun.

Jake for his part was absolutely stunned, not knowing what to say without shooting himself in the foot. Getting control over his cock or not shouldn't even be an argument, it shouldn't be locked up in the first place, yet face with a seemingly hurt Valeria he couldn't think of a single argument as to why he needed to be unlocked, not without hurting her even more that was which was doubly bad. On one hand he had really come to deeply care about Valeria who despite everything had become the best thing in his life, and without a decent argument he couldn't help but feel like there was no way she would be unlocking him. Instead he just stood there, mouth agape and lost for words not knowing how to respond. He really didn't want to be in permanent chastity, but then again he was slightly regretting bringing this up as well.

After a few brief moments it was Valeria who ended up coming to his rescue with a proposition. "I'm sorry babe, that might have been a little harsh. I know how much you love having your cock played with so much more than you like having your ass toyed with. I mean it takes some work to get your off when fucking that sexy butt of yours while your cock gets you off nearly instantly even with the best efforts to make it last. It's almost like pulling a trigger. I just don't like it nearly as much as I like fucking that ass of yours and it has been a bit of a chore. Although I guess there was one exception. You made sucking cock look so very good that I was thrilled to give it a go myself and it was somewhat fun for the little while it lasted. Not as much fun as you seemed to have had getting your cock sucked, or sucking that other cock for that matter, and not as much fun as fucking your ass was, but damn I still get all worked up thinking back to how incredibly hot that was, and I would love to do it again! So how about this, for every cock you suck off I'll suck you off, of course if you just want to give a hand job that's also fine in which case I'll be giving you a hand job as well. Of course one doesn't have to immediately follow the other. You can cash them in at a time of your choosing, so like a way simpler and faster way for you to earn yourself an orgasm whenever you want. This way you won't have to miss out on getting to get off through your cock and it's yet another thing the both of us absolutely adore!" Valeria enthusiastically proposed as if it was the best idea ever while Jake just looked at her horrified not really knowing what to say.

He guessed his chastity wouldn't become something permanent which was something, but at what cost. If anything the idea of sucking a cock or jerking one off for every release was even worse than the idea of only getting off through his ass not by a long shot but still. Whatever masculine pride he still had was quickly being pulled away from him and Jake couldn't help but feel utterly powerless to stop it, unable to make a solid acceptable to Valeria argument as to why this was insane, running into the exact same problem as when he had failed to argue how he needed to be released form chastity. It shouldn't even be an argument really, it was his cock and Valeria had no right to own it, but he was so far under her thumb that he didn't dare bring that up. Instead he just silently hung his head in defeat.

Valeria was more than pleased to see him yield though, this was going to be beyond awesome no matter whether Jake chose to earn his way out of his cage for an orgasm or not. She was all for either option so as far as her desires were concerned there was nothing other than winning to be done. Right now it was time to move on from that discussion though, after all she still had plans today. "Great that's settled then, and I would love to fuck that ass of yours to celebrate, and honestly I would have if not for something that has been bothering me since first fucking you yesterday babe. I wanted to bring it up yesterday, but supporting you through a difficult time took priority as it should. You are after all my precious sissy gurlfriend. Now for what was bothering me, fucking that sweet ass of yours was a bit of a mess, too much so for my liking which is about the only part I disliked about fucking your ass. I did some asking around and found out that it's completely preventable and Chelsea you know that hot owner of that sexshop we went to for you to suck your first cock is more than happy to help and help this new step in our relationship become all the more enjoyable for the both of us, so why don't you get dressed and we can get going straight away?" Valeria exclaimed enthusiastically, completely glossing over these major bombs she had just dropped on Jake as if they were nothing.

Jake did not share that enthusiasm at all. He wasn't a fan of things that had anything to do with anal at all, not when it was his ass on the line and especially not things to be found in a sexshop. He didn't really know what to expect, but he doubted he was going to like it much. Just like he didn't like the idea of going back to that sexshop one bit, not with the memory of that huge cock he had sucked surrounding it. Chelsea sure was hot like Valeria claimed but she kind of scared him as well, her dominant demeanour was incredibly intimidating to him. In the past he would have seen it as a fun challenge, but now if anything he was more scared of making a wrong move in front of her and would readily submit if she made a demand that didn't go opposed by Valeria, which once again rubbed in how much he relied on Valeria to stand up for him. On top of that the fact that she had been looking in on the video feed of him sucking that cock only made him all the more embarrassed to see her. Whatever the case may be though, Jake knew protest was futile and so rather than trying to delay, or argue he just put on his clothes like Valeria had asked, a little reluctant at most. This was happening and the best thing for him to do now was to brace himself he figured.

"Oh before I forget, I brought a little surprise for you as well, it just wasn't really appropriated to give it to you before, but from the moment I thought of it, I just had to make it for you and I think it has come out great, perfect to replace your score sheet with now that that's no longer needed." Valeria gushed as she fetched what at first looked like a soft pink thin piece of cardboard, but as she turned it around it was so much worse than that. A crumpled dollar bill was rolled up and stuck to the very top of the sheet with another one stuck a bit lower. In between were the words "For my two dollar whore" printed in a bold cursive with a heart at the end. Meanwhile the empty bottom half of the sheet was filled entirely with one of the many pictures Valeria had taken when she caught him off guard by pulling him back after sucking that cock. It was horrifying. There the cock was clear as day and look absolutely huge next to his face. The dark black flesh was positively littered with hot pink lipstick marks. Two thick lush prints were plainly visible on the scrotum from where Jake had sucked on the guy's balls, further more a thick bright ring of lipstick was surrounding the grith of this cock in various places along the length, it was brightest and thickest around the very base of the cock from where Jake had deepthroated it, and just behind the head to which Jake had retreated to pay some more directed attention to the sensitive knob. Another bright hot pink kiss mark was plainly visible on the tip of the dark purple head from which a string of cum connected to Jake's lips which sported some smeared lipstick of the same colour, his mascara run a little from where his eyes had watered while deepthroating this cock and his cheeks bulged out from all the cum in his mouth which he had yet to swallow in that picture.

It was absolutely horrible, a painfully embarrassing picture to remind him of probably the most painfully embarrassing moment of his life, sucking a real guy's cock still feeling that much worse than any kind of sex with his girlfriend, even the anal. All dolled up in his lingerie, with his hair and makeup done, he also looked so very emasculated compared to that big black cock. It was not something he wanted to remember at all, yet as Valeria put it in the pink frame she had bought for his score sheet right there on his nightstand Jake resigned to the fact that this was happening. Taking it away or hiding it would be rude, and he really didn't want to upset Valeria, mortifying as it may be. He didn't get to ponder on it for long though as right after setting it up just right, Valeria had grabbed his hand and pulled him out of the door that to go to the very place this picture had been taken as if he needed even more reminders. It had only happened two days again, but after everything that had happened after it, it still felt like it had been ages ago. While Jake was absolutely mortified, and defeated on the trip over, Valeria was all over him showering with kisses and sensual touches, which was amazing, but also so inappropriate on the bus. It got people staring and that was the last thing Jake wanted.

Chapter 62

For as awkward as it had been to be stared at on the bus, Jake would have rather been stuck on there with those strangers who had stared than step out at the stop closest to Chelsea's store. Not that he was left a choice that was as Valeria simply pulled him out and of to the store where Chelsea was sitting behind the counter with a strange look of pleasure on her face. The moment they approached she held up a hand. "Just one second, I'll be right with you." She gasped out as Valeria stopped with a curious and amused smile while Jake was fidgeting nervously, just wanting to get this over with, to go buy the things Valeria wanted and leave this place as soon as they possibly could. They didn't need Chelsea's attention or permission to shop here. They could shop just fine on their own but he wouldn't point that out to Chelsea, nor did he dare to tell Valeria that they should get a move on. Instead he just awkwardly stood there doing what both these women wanted.

Over the next few moments him and Valeria were witness to what they could only imagine to be an orgasm. Usually Jake would have loved to see something so spectacular and naughty out in the relative open. Now it just made him uncomfortable, his cock trying to grow hard in its cage while Valeria just looked on fascinated, loving the way Chelsea just oozed dominance and careless kinky fun. She couldn't imagine being quite this confident to make two relative strangers wait on her while she was having an orgasm, but she definitely respected and loved it. While Linda might be her partner in crime having helped her so much with tips and tricks on how to pull Jake into her sissy web, something Valeria had greatly appreciated and admired, Chelsea was quickly becoming her idol. She admired Chelsea all the more when this tough looking sexshop owner looked down. "Alright Rebecca, you may get up now and take over the counter if you will, I have some clients who need my help."

Much to Valeria and Jake's amazement they then saw a much older woman, somewhere in her mid forties if they had to guess pop up from behind the counter, her face bright red and soaking wet. Her once from the looks of it business chic makeup somewhat smeared. Her long brown hair cascaded down in a gentle wave and she was wearing what looked a classy skirt suit which would have looked suitable for a respectable office if not for the fact that one too many buttons on her blouse had been undone revealing too much cleavage and a hint of a lacey bra underneath, that and it left the elegantly woven black leather collar around her neck plainly visible. Rebecca looked like the absolute last person they would expect in a place like this, especially on her knees eating Chelsea's pussy like she had clearly been doing. She looked like the almost perfect picture of a respectable classy mature business woman, the glasses she soon put on again only further helping that look. It only got stranger when the woman answered Chelsea with a quick embarrassed. "Yes Mistress." Only for Chelsea to call her a good girl, pressing something on her phone which instantly had Rebecca startled, growing all flustered while she was clearly stifling some moans. Jake and Valeria could only imagine that it had to be a sex toy of some sort Chelsea had just activated.

Chelsea for her part just casually walked away from the counter like this was a regular workday for her. She was looking as fierce and sexy as ever in a bright pink latex off the shoulder dress with a pleated short skirt matching her hair. A set of sheer black stockings of which the tops were just on display and a pair of hot pink lacquered leather ankle boots completed the look. Seeing both Jake and Valeria stare at Rebecca Chelsea couldn't help but smirk a little. "Don't mind her, she's just one of my toys, and my accountant actually. A much better one than the boring guy who used to be my accountant at that. I spotted her around the office once when I came in to discuss my business, only to spot her around my store nervously looking for her very first toy ever one fateful day and we have had a lot of fun ever since. I showed her that while the type of toy does matter, the secret to a mind blowing orgasm isn't just in the toy, but for a large part also in how you use it. Helpful as I am I of course gave her a demonstration and she was instantly sold, more so on me than on the toy I guess, but well that's just a small detail. Point is we had a ton of fun. I insisted she'd take over my account and got her a few other client and before you know it she had her own office and a promotion over that boring guy I had to deal with before. Can you believe it? Not even I could convince that man to loosen up. In any case as they say the rest is history. Ever since Rebeccas occasionally helps me out around here after hours or on the weekends. The pay isn't great, but the benefits are isn't that right Rebecca?" Chelsea asked with a big smirk as Rebecca replied with a softly moaning embarrassed. "Yes Mistress." Once more, obviously embarrassed to have her life's story told like that, but she didn't complain, Chelsea had opened a whole new world of pleasure for her, beyond anything she could have even imagined and she loved it. It might be embarrassing, but she had to admit it was also kind of hot for her Mistress to so casually reveal her not so secret secret. Chelsea was the best thing that had ever happened to her, her work life, her personal life and especially her sex life had become so much better ever since meeting Chelsea. Who would have thought that buying a first dildo so late in life could have been such a spectacularly life changing event.

"In any case that's not what you're hear for if you want to have a chat with Rebecca you can have just that at one of the parties I often throw. Regardless of that you should really come to one of my parties I promise the two of you will fit right in if what I've seen so far and what I've heard from Jessica are anything to go off of. Now before we get to the matter at hands I have to say that I'm a little bit disappointed. I mean look at you Jane, you look like some kind of boring wannabe jock, where's that outrageously cute sissy from last time. I bet it's hiding somewhere underneath that outfit of yours isn't it? Correct me if I'm wrong but I bet you never leave the house without a pretty pair of panties at the very least. Come now gurl, there's no need to be shy, you can tell me. Are you or are you not hiding a pretty pair of panties under there?" Chelsea asked playfully with a raised eyebrow after she had quickly closed the distance between them to grab a hold of his chin and hold it steady, looking right into his shame filled nervous eyes from only a couple of inches away. It was way too close for Jake's comfort as he couldn't help but squirm even more.

Jake couldn't believe Chelsea's nerve to come at him like this, especially talking as loudly as she did as Rebecca, along with some clients further in the shop had definitely heard what she had just said. It was absolutely mortifying, and while he wanted to shush her he didn't dare to. Instead he found himself forced to answer her to get out of this awkward situation. Besides he felt like that was what Valeria wanted out of him anyways as she was having a good laugh next to him, enjoying the way Chelsea was making him squirm and not at all about to intervene. "Y... Yes Miss Chelsea, I am, and I'm sorry to have disappointed you." Jake admitted, his face turning an even deeper shade of red. He didn't even know where that sorry had come from, it just popped out. Chelsea just made him feel so weak and nervous that it had felt right somehow, like it did whenever he disappointed Valeria. If anything it only made Valeria laugh all the harder only to be scolded by Chelsea herself.

"You really shouldn't be laughing like that Valeria, I'm disappointed in you too, bringing this cutie in here all hidden, that's just cruel. Someone should definitely give you a right good spanking for that, keeping Jane's cuteness all to yourself like this. As her Mistress you should have scolded her before coming here." Chelsea spoke still holding onto Jake's chin as his eyes went wide. He didn't even dare think of saying something like that to Valeria yet here Chelsea was just saying it out loud without hesitation or regret with a confidence Jake could only dream of. A while ago he had had a similar confidence talking to girl, not quite up to Chelsea's level just yet, but he wasn't shy about saying anything. Things had most definitely changed big time in that regard as well though.

"Oh really? I'm almost tempted to let you do just that, I bet that lap of yours is mighty comfy. A bare bottom spanking I hope, but only if you promise to kiss it better afterwards. On the other hand why would I take a spanking when I have Jane here to happily take one for me? Isn't that right Jane? Wouldn't you be happy to take a spanking in your Mistress's stead?" Valeria asked smugly as she threw Chelsea a playful wink, the tough shop owner just breaking out in a huge smile. As Jake just watched on in shock as these two gorgeous women flirted with one another while he was caught in the middle. It was kind of terrifying yet so incredibly hot as his cock gave him plenty of trouble struggling against its cage once more. He couldn't believe that Valeria actually agreed to be potentially spanked, or that she was giving up his ass to someone else to take the punishment. If he had proposed something like that he would probably have gotten a very sound spanking a scolding and a whole lot more than that still yet here Chelsea and Valeria were in a flirty stand off while he knew he would have to submit to whatever they settled on. Valeria was clearly expecting an answer out of him so like Rebecca before him towards Chelsea he answered with an embarrassed. "Yes Mistress" of his own.

"Perfect you've got yourself a deal. I was thinking of twenty spanks, but since your sissy here has offered to take the punishment for you, I'll split it. Fifteen for her and five for you along with a kiss to make it feel better. Of course that's just a punishment, more importantly we need to rectify this mistake, so come on Jane, strip down, show us what cute lingerie you're wearing underneath this cause I am not going to help the two of you out with you looking the way you do now." Chelsea gleefully exclaimed as she looked at Jake expectantly, instantly joined by Valeria who was clearly in agreement, both of them just expecting him to strip down right here in the sex shop where literally every client could see him. He doubted he would be recognised, but the mere idea of being seen in lingerie by so many people was absolutely terrifying.

"Well Jane, what are you waiting for? You heard the lady, strip down to your lingerie right now or do you want to end up over my lap as well?" Valeria pushed sternly when Jake didn't immediately jump into action. The idea of stripping here remained terrifying, but not as terrifying as upsetting Valeria was, especially not as terrifying as upsetting both Valeria and Chelsea was. The last thing he wanted was to show his lingerie in a relatively public place, yet that was exactly what Jake ended up doing and he caved and reluctantly stripped down to reveal a bright pink satin thong along with a pair of sheer white stockings, the women pushing him to continue stripping until that was all he was wearing. It was horrible, and all the more painful as he noticed how a few customers browsing the store had definitely noticed, looking at him amused or downright lustful.

He badly wanted to cover himself back up, but before he could find the courage to do so openly defying both girls, Chelsea reached down to gather his clothes. "There we go, I'll keep these safe until you're ready to leave. You are looking so much cuter now Jane, although I understand how this would be inappropriate to wear on the bus. Still you could have opted for something cute to cover it with rather than these dreadfully boring things. In any case your look could use just a little bit more flair still, we're definitely going to have to find you some shoes to walk through the store, and something to cover you up a bit more. In any case why don't you leave that to me and your Mistress? You can wait with Rebecca behind the counter and she'll be more than happy to do your makeup and hair, isn't that right Rebecca? Now be a good gurl and rush on over." Chelsea snickered as she and a laughing Valeria walked into the store with his clothes in hand, leaving Jake trapped in nothing but his lingerie.

It was terrifying, yet there was nothing he could do about it. There was no way he could leave the store like this and even if he had the courage to demand and take his clothes back, he couldn't help but feel like Valeria and Chelsea wouldn't give them up without a fight. Not that he could even begin to think of snatching them out of their hands. He was utterly doomed and while he didn't want to wear makeup either, he rushed to the middle aged accountant behind the counter. He would have thought of her as a MILF before. Not exactly what he tended to go for, but Rebecca was hot enough that he certainly wouldn't have turned her down if the opportunity had arose. Now he couldn't even stand to meet her eyes though as she was about to put makeup on him. At least the counter offered some modicum of cover which he could use more than ever. Besides it wasn't like he would have been able to refuse his makeover anyways or he would have been in big trouble despite his compliance in having stripped. If he had thought yesterday had been embarrassing, today was somehow shaping up to be even worse.