From Soccer to Sucker Pt.49

Chapter 63

While Jake was mortified and incredibly nervous about this whole thing, he had to admit that Rebecca was very sweet and sympathetic. "Relax sweetie, you have nothing to be embarrassed about, in fact I think you look incredibly cute. Now let me just get to work and I'll make you look as pretty as I can. You know I really do hope your Mistress takes Mistress Cheslea up on that offer. I would love to see you around at one of her parties and looking like you do I'm sure you'll fit right in, everyone will just love you. Now try to take a deep breath as this might sting a little, but trust me you're going to love the results." Rebecca gushed as she eyed him up, drinking in his look and most obviously checking him out. In his old life he would have most definitely been up for a flirt with this hot MILF if she checked him out like this, but now it just further fuelled his shame and discomfort. He already felt self conscious enough about being a big sissy that he could really do without being called cute or pretty. Rebecca clearly meant well but she wasn't helping, and neither was the fact that the strong scent of Chelsea's pussy was heavy on her face and breath.

He had been so wrapped up in his shameful thoughts that he hadn't even really paid much attention to the mention of a sting, or the fact that makeup shouldn't sting at all, leading him to be caught completely off guard when something painfully pulled at his eyebrows. His initial reaction was a loud yelp which gave Rebecca time to get in two more quick pulls before he was able to stammer out. "Wh... what are you doing?" In shock, somewhere deep down knowing the answer to that question, but still he was in such disbelief over this happening that he asked anyways which was a terrible idea as it allowed Rebecca to get in a few more pulls. He should have slapped her hand away and he would have if he hadn't felt so incredibly self conscious sitting here in the relatively public place in just his thong and stockings. It prevented him from finding the confidence to take any immediate and thorough actions.

"I'm just tidying up your brows a little bit. It'll help your look out so much so Mistress Chelsea will be very pleased. I bet your Mistress will be pretty pleased as well, now relax and let me continue. I'm not doing anything drastic, just plucking a few stray hairs so they don't look too bushy and unkept. It'll be hardly noticeable, I assure you, but at least it won't distract from your pretty look like your current brows would. In either case I'm afraid it's a little too late to stop now or it will show, one half finished brow and a messy somewhat bushy one are just a bad look. If you want I could shape them a little rather than just cleaning them up though, it would definitely help turn your look more spectacular, but that's up to you. I can do anything from giving them a nicer arch to really thinning them out." Rebecca offered as she continued to pluck away on his brows, cleaning them up like she had just explained, although Jake had no idea of just how much damage she might be doing to them as there was nothing around him to allow him to have a peek at himself.

Jake was absolutely lost for words, stunned by Rebecca's explanation. What could he even say or do about that other than hoping that Rebecca's efforts would actually be nearly unnoticeable? He believed her that stopping now was bound to be more noticeable than if she finished, but that still didn't make any of this any more okay. He couldn't believe this was happening to him, and he couldn't even really blame Rebecca as this was well within the realm of a makeover and after stripping down to this lingerie in a store, agreeing to get his makeup done, it really wasn't that far fetched to assume he would be okay with some mild work on his brows as well. If anything he was a victim of his own spinelessness and Rebecca's eagerness to please her Mistress. It was all the more proof to him that he was little more than a sissy and that felt all the more true as he awkwardly stammered that just cleaning them up like she was doing would be more than enough, hoping to do as much damage control as he could possibly manage.

It took a little longer a couple more painful pinches to his brows, but eventually Rebecca did move on to the actual makeup. Much like with his eyebrows, she was working hard to do the best possible job on him that she could, applying a full, heavy and meticulous look, more than anything he had ever put on his own face. It made him rather nervous to feel her applying so many products to his face, but by now Jake just resigned to his fate so he didn't utter any protest or make a fuss at all. Besides, it might actually be beneficial to wear so much makeup as it might make him a little less recognisable and the damage was already done anyways, unlike his brows this would come right back off he thought as Rebecca went to town on his face with product after product before combing back his hair and gathering it all in playful high ponytail high upon his head which she tied off with a simple black hair tie fished from her purse before finally fishing out a tiny pocket mirror to show off his new look. "Tada! What do you think Jane?" She asked with a big excited smile as Jake's jaw simply dropped.

Valeria had made him look embarrassingly pretty in the past, and he was getting shamefully good at doing his own makeup, or at least parts of it by now, but this was on a whole new level. Plenty of foundation had been used to smooth out his complexion only for strategically placed highlighter to make his nose look smaller and his jaw line softer. He was sporting a real pair of fuck me lips, looking thicker and fuller than how he managed to get them, not only that, they were painted a bright hot pink with a glossy wet looking finish, looking almost as if they were inviting a cock to work its way between them. His cheekbones had been highlighted with plenty of rosy pink blusher, his eyelashes meanwhile were made to look long and full while perfect wing tipped eyeliner surrounded his eyes. His eye lids now sported a blend of different pinks going form bold bright pink closest to his eyes to a more mellowed out softer shade higher up. The part which he had been most afraid of, his brows, still looked very full, darker than usual and with a subtle arch. They sure looked clean, but it was impossible to tell for Jake if the arch came from Rebecca plucking a little more than she had let on, or if it was a result of some crafty work with the eyebrow pencil Rebecca had clearly used. He really hoped it was the latter, but it didn't exactly put him at ease at all.

Jake barely had time to process his makeup look before Valeria and Chelsea arrived back from their little trip into the store to find something more for him to wear, or supposedly so as they weren't exactly carrying much at all. They did both break out in huge smiles though as they laid eyes upon his made up face. "Oh my that's so much better don't you agree? You look a lot prettier already Jane and Rebecca, you've most definitely outdone yourself once more. She's a real artist that one. She always loves dolling up a sissy and she's great at it as well. Rebecca always manages to get the best possible look out of any face she lays her brushes on. You've really made your Mistress proud!" Chelsea gushed as Rebecca beamed, thanking her profusely while Jake just blushed heavily underneath the thick mask of makeup.

"I wholeheartedly agree, my sweet sissy is looking prettier than ever. You really do have a talent for makeup Rebecca, do you perchance give lessons? Jane here has recently quit one of her hobbies and she could definitely pick up something else to fill up all that extra free time she now has. Learning how to do her makeup this spectacularly would be great, an amazing skill to pick up, it makes me want to fuck that cute tush of hers all the more, or ravage those pretty lips with my strapon, its hard to choose really, but I do love what I'm seeing and it would almost be a shame to ravage that look when she can't touch it up. I'm sure we could come to an arrangement to make it rewarding for you as well!" Valeria gushed as Jake looked at her stunned while Rebecca giggled and thanked her as well. The last thing Jake wanted was to look like this on a regular basis which was the whole pointed of learning to replicated this look or one like it himself he guessed. Learning as much about makeup as this look required was another thing he really didn't want to do and the fact that he would according to Valeria's proposition have to do it instead of soccer practice only made it all the more painful, as was the fact that she had called that just a hobby like it had been nothing. It had been a huge part of his life and looking to become even pretty decent as a career instead here he was potentially about to learn how to do his makeup instead while Rebecca gushed that she would love to if she could and Chelsea quickly added that she would love to figure something out to make it work. Jake hadn't even said a word, yet it was already looking like he would have a new thing to do on his newly freed up evenings.

"In any case, that's not what we're here for, we can figure that out later, but first we have some shopping to get done and we found you the perfect shopping outfit!" Valeria gushed as she revealed what they had brought along which turned out to be very little much like he had feared. The largest item they had brought along was a pair of what he could only describe as stripper heels, bright pink lacquered leather ankle boots with a three inch platform in the front and an eight inch heel in the back. Other than that there were only three more items starting with a set of bright pink heart shaped pasties to go over his nipples, a pink leather collar and a chain link leash to go with it. If anything it would only make his whole get up that much more mortifying rather than actually providing him with some decent kind of cover. His nipples would be the only thing actually getting covered and these heart shaped pasties would arguably make them look worse instead of better.

With so little to put on Jake was dressed in no time at all, standing way too tall in these very high heels. He towered over everyone yet that didn't give him even a shred of confidence. On the contrary, it made him all the more nervous as his height alone was bound to draw looks. Dressed as he was right now in nothing but lingerie, heels and leash with a heavily made up face every bit of attention was too much attention. It might not be in public public and given what they had walked in on, it was acceptable and maybe even a regular occurrence here at Cheslea's store, but that didn't make Jake feel anymore at ease and neither did the gushing of all three women about how much better he looked than when he had walked in. Valeria while now a ton smaller than him was clearly still in full control as she with a big smile and a strong tug on the leash brought him down to her eye level while Jake struggled to keep his balance as she did. "You look so incredibly hot my sweet sissy Jane, you can't believe how excited you have me right now. I love you so god damn much like you wouldn't believe it. You're the best boyfriend I could ever wish for and more and I can't wait to make you feel incredible, first lets get a bit of shopping done shall we?" She whispered into his ear, softly biting his earlobe as she finished her sentence before finally giving the leash some slack again to allow Jake to get upright once more.

It was nice to hear how madly in love with him Valeria was, but that didn't ease his nerves right now at all. Still Jake couldn't imagine putting up an actual protest, instead he just tried to brace himself to make it through this. It honestly made him feel so pathetic, but he couldn't muster up the confidence to make a stand, especially not against two to him incredibly intimidating women while he was feeling so incredibly vulnerable dressed as he was. Hell he hadn't even been able to stand up against Rebecca, Chelsea's sub, so the idea that he could stand up to them was too ridiculous to even consider. Instead he shamefully allowed himself to be tugged along by his leash as Chelsea and Valeria walked back into the store, now with him in tow. It almost felt as though he was being paraded around and Rebecca for one was sure as hell checking him out as he left. A hot woman checking him out used to give him such a cocky rush of confidence, but now it just made him feel all the more self conscious.

While the store wasn't crowded by a long shot they did drag the attention of every single person in the store. Or rather Jake did. Both women walking in front of him might have been gorgeous in their own right and especially Chelsea was wearing an eye catching outfit of her own, but that simply paled compared to the way he was dressed, or rather undressed. Despite their presence all eyes were on him and on him alone, the people spotting them weren't shy of a little staring either making him Jake all the more uncomfortable. Especially the way the men stared at him and doubly so when eh could see them popping a tent. It gave him some shudder inducing flashbacks to the club where cock after cock had popped through the glory hole Jessica had been taking full advantage of with him, or worse to the cock he had practically worshipped right here in the very store. It gave him a pretty good idea of what was hiding in those pants, what those erections would look, smell and even taste like leaving Jake utterly disturbed. He couldn't believe he was thinking about cock with two such hot women walking in front of him, but it almost naturally flowed from all his worrying about his surroundings and the people seeing him like this.

Pretty soon he had a whole new thing to worry and blush about though as they finally came to a stop in front of a shelf stacked full of about every kind of anal product he could imagine going from dedicated lubes, to enema bags, and mostly butt plugs. This shelf held about every butt plug he could imagine and a whole lot more that he wouldn't have even been able to imagine. They went from shocking shapes to even more shocking sizes and pretty much everything in between. "See something you like my sweet sissy? I bet you would love to be wearing one of those right now wouldn't you? To have your ass stuffed even when I'm not actively fucking it you little butt slut. Which one would you like best? A classic like that one over there, or better yet, I bet you would just love that one, shaped like my cock you loved some much." Valeria chuckled as she saw him staring at the wall of plugs, thoroughly enjoying his discomfort and while it wasn't the initial plan she was quite liking the idea of Jake being stuffed for her at all times another naughty secret to hide under his clothes for her amusement, plus she just loved the idea of his ass being full of something so a plug would really be perfect.

Jake on the other hand was horrified by the idea, not only that but Valeria was being way too loud. Well she was speaking normally. He really wished she would keep her voice down especially regarding such a mortifying topic and he desperately wanted to dispel her assumption, but Chelsea spoke before he could even think of what to say and how to say it. "That is a great idea and something I actually wanted to bring up when you asked me to make this anal adventure as fun as possible for the both of you. Plugs are not only a fun naughty secret to share, they can also offer so very much in the way of play, just think of the possibilities with a nice vibrating plug. In either case, training that ass is also a great way to heighten the fun when you do fuck his ass. A well trained well prepared butt can offer so much fun right from the first stroke as it skips right past the potentially lightly uncomfortable warm up phase where his ass needs to get used to that starpon again. In any case lets have a look at your options regarding the first issue you brought up first shall we? If you want to eliminate the part that can be a little messy then a good enema kit is your best friend. Now I for one always love to use one with a fun shaped nozzle as it makes the whole enema experience a little more fun and a nice form of foreplay for me at least. All that water can tend to cause a bit of cramping, but I just love to see some of my subs squirm as I tell them to hold it for a little while." Chelsea said as she carried on taking about all the different options, nozzle shapes, and even soap scents before carrying on with some instructions about how to use an enema kit. Just like with Valeria Jake just wished that she would keep her voice down while he listened on in horror to what he was about to be put through, especially judging from how excited Valeria seemed to be. He really felt like he should say or do something, anything really, but seeing how Valeria had clearly made up her mind he simply braced himself to accept yet another embarrassment into his life.

After everything was explained Valeria eagerly made her pick settling on a rather scarily large pink rubber enema bag, joking how pink was so his colour which Chelsea was all too happy to confirm. The bag had a rather long rubber hose coming out of the bottom which ended in a four inch long and relatively gritty pink cock shaped nozzle. It wasn't as big as her strapon was, not in any sense of the word, but that didn't make it any less scary to Jake especially not after Chelsea's recommendation of two enema's a day to stay squeaky clean at all times. The idea of putting that thing up his ass twice a day was utterly mortifying, especially since there was no other reason to it than to be ready to get fucked by Valeria without making a mess. The cherry scented soap Valeria had selected to go with it only added insult to injury as the only thing it was good for was making his ass even more attractive to get fucked which was the last thing he wanted especially when Valeria had claimed she loved that scent so she could somewhat feel as though she was popping his cherry all over again. Still be that as it may, Jake couldn't bring himself to actually pick a fight over it and it only made him feel so much more pathetic. Valeria for her part was incredibly enthusiastic over it all. "Mmm I can't wait to get to fuck that ass of yours once it's properly cleaned up Jane. Of course keeping it clean will be your job and you better make sure it is at all times as I don't want any dirt on my strapon ever again understand? Now that you'll have the right tools there's no reason why that should ever happen again. I'll be happy to help you get cleaned up whenever I'm around, but when I'm not I expect you to take care of business as you never know when I might be in the mood." Valeria teasingly yet sternly spoke as Jake was left to utter a meek "Yes Mistress" much to her delight.

From the enema bags they moved on to the butt plug display as Chelsea delighted in telling them all about the collection she had for sale, the upsides and draw backs of every plug or set while Jake couldn't help but wonder if this was his fault for staring at them earlier. Would they still be shopping for plugs if he hadn't been caught looking at them a little too hard? The answer was most likely yes, still Jake couldn't help but blame and curse himself at least a little over it. As Chelsea explained everything it was starting to look more and more likely that he would be getting his filled pretty much 24/7 going forward, whether it was with the nozzle from the enema, Valeria's strapon, or one of these plugs. It was looking more and more like the question wasn't if he was going to be wearing a plug, but rather which plug he would be wearing.

At the moment he guessed he should be counting himself lucky that soccer was a thing of the past for him. Sure a plug was probably the easiest thing to hide considering how it would mostly be up inside of him, but the mere idea of being in close contact with his old friends while a fat plug was filling his ass was downright mortifying. Hell even worse actually playing soccer, running around was bound to be a real pain if he had something large stuffed up his ass. It might be the most hidden aspect of these embarrassing things Valeria made him wear yet at the same time Jake feared it was the first thing that would be noticed. The plug itself might not be visible until it was way too late to get away with anything, but Jake couldn't help but dread the idea that his gait might be affected by it and with it he dreaded to think that people might notice and get suspicious. While he could try to walk normal, it was plenty cause for worry for him. He guessed the best he could hope for was that people wouldn't connect the dots, but it was bound to draw a lot of suspicion he could miss more than anything.

While Cheslea continued her explanation Valeria caught him off guard when she suddenly pulled him down by his leash once more. "Hey Jane, would you like to suck a cock right now? Cause that guy over there is has been checking you out and lurking around us for a while now. I bet he would be more than up for it if you are, and he's rather handsome as well. I think it would be hot if you wrapped your pretty lips around that cock he's hiding. Of course I would be more than happy to return the favour and suck you off at a time of your choosing in return. So what do you say Jane, are you up for it or not right now?" Valeria whispered in his ear, luckily keeping her voice down this time but that didn't make her statement any less shocking. Sucking cock through a hole in the wall had been bad enough, dropping down on his knees for a guy who had been staring at him for a while was a whole other matter.

"N... no thank you Mistress, I'll pass." Jake stammered out not really knowing what else to say. He felt so stupid for actually saying thank you over such a horrid proposition, but then again nothing good come from upsetting Valeria he figured, barely even realising how very conditioned to pleasing her he had gotten. Being at his utmost polite, near grovelling levels towards her had almost become second nature to him now. In fact he had gotten so used to doing everything he was told that he was relieved that Valeria had only suggested it rather than instructed it. He would have protested if it had been a demand, but it was a relief that he didn't have to defy Valeria as he was terrified of the consequences if he kept his ground and flat out refused. Still while he had avoided that mortifying blowjob Valeria's playful suggestion did have other mortifying consequences. He had inadvertedly looked over to where Valeria had nodded only to accidentally briefly lock eyes with the guy who had been ogling him, and opportunity that guy had instantly taken to throw him a wink. Jake had quickly looked away again, but he had been let mortified nonetheless.

While a little bit better than being on the guy who Valeria had suggested he'd suck off, turning his attention back to Chelsea who happily rambled on about all the different plugs, one of which was bound to end up his ass wasn't exactly helping him put his shame behind him. It was still mortifying, just to a slightly lesser degree and whether he tried to focus on what Cheslea was saying, he just couldn't stop himself from thinking back to that guy and Valeria's suggestion. The fact that he had been called handsome while Jake constantly had to hear how pretty he was, really stung, but not nearly as bad as the fact that he was tightly locked up while that other guy had easily popped a hardon by ogling him. He might have avoided sucking that cock off, but that also meant that for the foreseeable future his cock would remain tightly locked up as well, his only orgasms coming form Valeria's strapon. Up until now he had always kind of known when he would get released, but right no he didn't have a single prospect of release and it made his chastity sentence all the harder. While he could technically get released way more often now, there was no way he was going to suck another cock if he could help it and with that being the only option for release as of now, there was no telling if or when he would get out again.

It was something he kept on pondering as Chelsea talked, there was no way he was going to ask to suck a cock or simply agree to it unless he was absolutely desperate which might just happen given the circumstances. Still Jake's main hope was that Valeria might just take pity on him at some point and decide to let him out anyways. He couldn't escape the thought that it was a vain hope, but still it was better than just preparing himself for the prospect of inevitably sucking another cock. Right now however he was snapped out of his train of thoughts when Valeria finally came to a decision about what he was going to have to put up his ass for the foreseeable future. The plug might be his to wear, but as the leash indicated it was very much Valeria who was in charge and so the decision did end up falling on her, and that choice ended up being worse than he had anticipated. For starters it was relatively large, way larger than he had hoped it would be. Not only that, but it was a little oddly shaped as well with a slightly curved tip. Further more the plug was hot pink coming with a heart shaped crystal base that would obnoxiously decorate his butthole. Perhaps most worrying of all however was the fact that this plug seemed to come with a vibration function and he dreaded the prospect of finding out why that was. After all he doubted Valeria would go for this specific plug if she didn't plan to use that function.

"Excellent choice! Perfect for keeping that sweet ass pretty and ready at all times, plus it really does open up for a lot of fun possibilities. With that curved tip it'll pressure his prostate just right so if anything Jane here will be loving this new addition to your sex life even more than you will. In any case if that's all I'd be more than happy to invite the two upstairs for a little demonstration, and of course for that well earned spanking." Chelsea said with a playful yet meaningful wink leaving Jake in shock. The more he learned about this new plug the worse it had gotten. On top of that he had almost forgotten about the spanking. A spanking which might not be the worst thing in the world, but he couldn't help but that demonstration Chelsea had just suggested did worry him a lot. The later he had to deal with all of this the better, yet when Valeria eagerly agreed he guessed he wasn't even going to get to wait until they got home. Regardless of what he thought, they were soon back on their way to the register to pay for everything while Rebecca made a few remarks about how much fun they were bound to have with their new purchases. With everything paid for Chelsea instructed Rebecca to watch the store a little longer while she led an eager Valeria and a reluctant mortified Jake through a door labelled "private" to have some real fun with these two.