From Soccer to Sucker Pt.33

Chapter 42

It had ended up taking even longer than last time to get Valeria to an orgasm sucking on that strapon which felt and acted surprisingly real. Jake couldn't help but be caught off guard again when Valeria's juices squirted out of the tip of that strapon straight into his mouth like a real ejaculation. Of course it tasted like pussy rather than cum, but it didn't feel any less disturbing. Still Jake was learning so rather than getting to Valeria's nails right away, he got up, walked over to the mirror in a sort of crude mince only to touch up his lipstick and mince back over to Valeria. Heading over to her wasn't a particular boost to his self esteem, but it was way better than facing his mirror image during such an effeminate action.

Having learned from his past mistake Jake dipped into a deep curtesy and asked. "Would it be good if I painted your nails for you now Miss Valeria?" With that he rose again to await her reply, pretty much knowing she would say yes. After all it was nothing but a formality, or at least it had sounded that way, but it was a formality which threatened to bring him a whole heap of trouble if he forgot which was the last thing Jake wanted right now. It made him feel like a complete fool, but after everything he had done so far today what was one more indignity? One thing was for sure this day couldn't end soon enough, but at the same time he still hoped to gather a lot of points as he wasn't quite at earning an orgasm yet.

"I'm glad to hear you are learning my dear sissy Jane. That is a much better attitude towards me already. Keep up that good work. And of course you may paint out nails. I've decided on a hot pink to go with your sissy maid's outfit, isn't that lovely? Oh and Jane please paint your fingernails while you are at it. You look so pretty that it would be a shame to keep your fingernails as boring as they are now. Besides I have everything you need to restore them to their clear protective coat before you leave so I don't see any reason why it should be a problem. Do you?" Valeria casually asked as she handed over the bottle of hot pink nail polish while Jake stood there in stunned disbelief. After everything he had already done for Valeria, she was demanding even more? This was so unfair, and he shouldn't be putting up with this.

Yet in the end Jake caved yet again. He really didn't see any reason why he couldn't wear bright finger nail polish. Well no reason other than that he wasn't a sissy and wanted to maintain some dignity. After everything he couldn't even help but doubt whether he wasn't just a sissy like his collar claimed. Ik either case his dignity wasn't a good enough reason to sway Valeria and get left off the hook without consequences and he guessed it wasn't that different to how he had been maintaining his nails up until now. It was just a bright colour rather than a clear invisible coat and by the time he left here it would be gone again. So with a heavy heart he dipped into another curtesy. "That shouldn't be a problem Miss Valeria, I'll get to it right away." And just like that he sunk down on his knees and dutifully started his next chore.

Between the multiple coats and the drying time, painting nails was always a time consuming chore, but right now it was even more so than usual. After all he did have ten more nails to paint and making matters even worse doing the nails on his hands was always harder given how he had to use his none dominant hand for half of those. He had gotten some practice making it a little easier, or at least a little neater now that he was using a bright colour, but it remained harder to do. On top of that it was mentally challenging as well seeing his hands become girlier and girlier with every coat of glossy hot pink nail polish. The first coat had been by far the worst, but the others just made it that much cleaner, fuller and thus that much more devastating.

By the time he finally finished his fingers sported a solid glossy hot pin colour just like his toenails and those of Valeria. They made his hands look a surprisingly lot more delicate. Especially with those fingerless gloves he was already wearing. "They look so pretty right? Isn't that a lot better than that dull boring clear polish? I certainly think it is, and they came out rather nice as well so if you wouldn't want to clean it off later I would definitely understand. I would even applaud it. In any case, the choice is yours and now that I think of it, I haven't really rechecked your lips just yet. I guess that's a good thing as it means they are passable enough not to immediately bother me, but let's have a better look shall we?" She spoke with a grin as she leaned forward and grabbed onto his chin only to lift it up towards her and carefully study his face making him feel rather nervous.

Valeria caught him completely by surprise when she pulled him in even further only to kiss him full on the lips, keeping him locked into a passionate tongue twisting kiss. When she finally released him again she couldn't help but giggle. "Yes those were very kissable lips indeed. I still can't get over how pretty you have gotten my sweet sissy Jane. Now go put your stockings and heels back on and get on with your other chore, you still have a lot to do don't you sissy?" Valeria giggled as she sat back again, leaving a blushing Jake on his knees at her feet. While her lipstick smeared silicone cock dangled dangerously between her legs, serving as a permanent reminder of the by now two blowjobs he had given her.

He couldn't help but feel so ogled as Valeria clearly lusted over the sight of him carefully rolling those stockings up his legs and fastening them to the garters. He guessed he should feel happy that Valeria was so into him, but if anything it was uncomfortable to the point where he was happy to be back in his heels and up on his feet. Dropping into another curtesy he agreed with Valeria then minced back off, only barely remembering to stop by the mirror to touch up his lipstick again. It was all the more painful holding that tube with his now bright pink fingernails, but he had to keep his lips kissable for Valeria. With that he pretty much went on with his chores as usual, only now dressed and made up like a sissy maid wearing a collar, a reality he just couldn't escape from the sensations down to the sounds his outfit made.

Jake's Sunday ended up being a very long and hard one. He did every chore around Valeria's apartment he hadn't yet done, cooked all her meals, offered her massages, and gave her plenty of orgasms. He ended up sucking her cock two more times throughout the day, but the majority of her orgasms came from his tongue directly on her pussy. The strapon's sensations were great, the sight of Jake sucking it was incredibly empowering, but in the end the sensations weren't as amazing as his tongue was, and as they said, variety is the spice of life. This strapon was a great way to switch things up, to get her thrills in a wildly different way, but there was no need for Valeria to compromise on anything. She could have all the pleasure however she wanted that pleasure and she definitely planned to make more use of both down the line.

As far as Jake was concerned, he could do without that strapon ever again. Eating pussy was messier, but at least it left him feeling like more of a man than sucking on that silicone cock. Despite that he had been putting more and more passion into sucking that cock. Valeria constantly hammering on how it was for his own future good and encouraging him to put more soul into it. It did also just become a little more manageable as he got over the main sting of embarrassment that had accompanied sucking Valeria's strapon the first times. That being said it remained wildly embarrassing no matter how many times he sucked it.

The constant clicking of his heels, his stockings rubbing together causing plenty of trouble in his cage and the fact that he had to touch up his lips more times than he could count served as strong reminders of just how big a sissy he was. Valeria almost always found one reason or another to smudge his lipstick for him forcing him to fix it. And sometimes it was just his own fault. The first time he had drank he couldn't help but blush over the lipstick mark left behind on his glass which pretty much forced him to touch them up again. On the few times Valeria had caught him not immediately touching up his lipstick, walking around with less than kissable lips as she had called it he had gotten a quick spanking which was more embarrassing than painful really. By the end of the day he was really getting the hang off touching up his lips and was even getting in the habit of doing so. Every time they kissed he pretty much instantly went looking for a mirror without even thinking about it anymore.

His legs and feet were sorer than ever, his confidence at an all time low and his shame at an all time high by the time the evening arrived. Nevertheless he felt better than he had in a long time. His week had been nothing but a cold shoulder from Valeria and frustrations and downright anger from his friends. For as embarrassing as his day had been Valeria had showered him with praise, affection and lust. He had been quite used to girls being smitten by him, in what felt like a lifetime ago, none had ever been quite as taken with him as Valeria seemed to be right now and though her compliments or the kind of attention like the pinches to his exposed bottom weren't exactly sources of pride. It felt nice to be this adored again after everything. It made him feel good in a kind of squirmy way.

At least when the time to head home arrived Valeria did keep her word about letting him fix his nails back to the clear polish and allowing him to remove his makeup. His very last chores of the day was performed naked, washing his entire sissy maid's uniform and hanging it to dry so it would be ready for future use. His collar got unlocked and he was allowed to change back into his regular clothes, which sadly still meant wearing a frilly satin thong and sheer stockings with nothing to really cover it up. He was more than eager to finally retreat to the safety of his dorm to finally process all which had happened this weekend. He might have enjoyed Valeria's attention, but he was glad to be done with the shame for now. Not that it would ever really disappear given all he had to adhere to even when he was home alone.

Jake was just about ready to leave when Valeria pulled him into one last passionate kiss. "You've been amazing this weekend babe and you have most definitely earned that blowjob. I promise you'll get the best blowjob of your life come tomorrow after class. In any case, thank you for being my sissy maid this weekend. I've had the time of my life and I hope you enjoyed yourself as well. If not then I'm ever so much more grateful for you to indulge my wishes. Like this I am certain our relationship will have a very bright future." Valeria gushed adding some more sweetness after the intensely embarrassing ordeal, actually feeling rather genuine about it. Even the wanting him to enjoy it to some degree. She might love embarrassing him, but as her sissy he was just so precious that she was actually falling head over heels with this new him. The way he was so shy, squirmy and over the top girly was just so very precious.

Just like that Valeria finally allowed Jake to truly leave, feeling kind of bewildered, confused, and above all embarrassed to have felt the urge to check the lipstick he was luckily no longer wearing after the kiss. The genuine thanks did make him feel kind of good despite how happy he was to finally have this whole embarrassing weekend over with. He guessed in retrospect it wasn't that bad. No one but he and Valeria had picked up any of this and it had made her very happy which was a good thing. Plus it looked like Valeria was looking forward to that blowjob even more than he was for some reason. All in all he had made her happy, earned himself a huge bonus in the sense of him finally getting to go a bit further than just a handjob. Despite all she had put him through Jake was looking forward to seeing Valeria tomorrow.

His weekend may have been hard and embarrassing, but through everything Jake had still grown incredibly turned on. His cage was pretty much permanently giving him trouble by now, making that blowjob for tomorrow sound all the sweeter still. The fact that his bedtime lingerie was only making things worse as he tried to fall asleep dressed like Valeria demanded despite suspecting she wouldn't show up anymore today, only made him feel like a bigger sissy. It wasn't easy, but eventually he managed to drift off to sleep, only to relive the events of the weekend in his dreams, but worse. In those Valeria's way too life like dildo was an actual cock.

Chapter 43

When Monday, the start of a new week arrived, a whole new set of worries also arrived for Jake. His weekend had been so preoccupied being Valeria's sissy maid that he had barely had time to really process what had happened between him and his friends. As he got ready that morning, his worries rose the closer he got to being ready and needing to leave. He guessed he could go on avoiding them like he had done ever since he had sacrificed his socks and boxers, but the sheer idea that they might be mad enough to get confrontational was scary to say the least. He felt like they might be pissed enough to do just that. So when the time came for him to head to class he was worrying more about his friends, or previous friends than he was about his stockings and panties potentially showing, although with how very turned on he was and every step serving as a firm reminder of his situation, they were never far from his mind either.

Much to his relief, his plan on avoiding his friends seemed to work for his morning classes at the very least. For as painful as it was he could only hope his friends wanted to avoid him just as much as he wanted to avoid them. That being said, avoiding everyone did make him feel rather lonely, somehow getting him to look forward even more to seeing Valeria later this evening. The only person who seemed to really care about him right now. He really longed for her intimate touches, kind words and passionate kisses. Just thinking about it gave him trouble with his cage yet again, as well as turn his cheeks bright crimson as he realised those very same intimate touches and sweet words he was dreaming about only really revolved around him as a sissy, her sissy.

Sadly for him his stroke of luck didn't last. He had just about taken place at a table to eat all alone when Tom, his replacement as team captain of all people came over to taunt him a little. All he could think of doing was awkwardly slide a little further under the table, wanting to prevent at least his stocking clad ankles from showing at all costs as they would make things so much worse. He didn't know how he would live down people finding out that he was nothing but a big sissy. "Look who we have here, if it isn't babe. You kick like a girl, and you let a girl walk all over you. No wonder you are keeping us down. Well at least now the team has a real man for a captain once again. Just so you know if it had depended upon me and the guys you would have been kicked off the team. The only reason you're still on the team is because the coach still believes in you based on past performances as far as I can remember those have only been awful. You don't even..." Tom mocked as Jake couldn't help but blush, cast his head down and take it all while feeling increasingly worse about himself. It was awful, especially knowing the guys had wanted to kick them off of the team altogether. He didn't know things had gotten that bad between them. Then again he didn't know much of anything going on among his ex friends anymore given how he had avoided them for so long.

Tom was unable to fully finish his speech however as he got interrupted by Valeria showing up which only made Jake shrink down even further. When it came to him she had constantly taken some jabs at him in public, making him call her Miss and such in public. Right now she was standing up for him though in an odd turn of events. "Oh shut up Tom, the only reason you can't remember is because you have a memory like a sieve, or do you mean to imply that there's something wrong about losing to a girl, or caring about your girlfriend. Does Emily know you think that way? Would you like to face of in a duel for my babe's honour. I bet I'll kick your ass even easier than I did his, he was actually rather good despite what the score told. I doubt you'll do as well, but there's only one way to find out isn't there Mr. big shot captain. Why don't you gather your team at the ring and we'll show them that kicking like a girl is a compliment. Now did you have anything useful to say, like anything at all, or are you just so damn proud to be a second choice captain now that my babe is going through a little bit of a though spell. The only reason you even get a shot is probably because of me, as I might have accidentally distracted Jake's head a little too much with all the crazy fun we're having, things you can't even imagine believe me." She spoke angrily, as she moved in between Tom and Jake. In a sense she was kind of happy that Jake was falling out with his old friends as they were all only feeding one another to be a bigger asshole the way she saw it, plus it made him all hers which is exactly what she wanted. That didn't mean she would let some asshole walk all over her new and improved Jake though.

"Uhm... Eh, that won't be necessary. I'm just going to go over there and sit with my friends." Tom stammered, completely taken a back by Valeria's aggressive stepping in. Her words really did sting cause no matter how he looked at it, he knew she was right, he really was the second choice captain and Jake had once been the best of them, good enough to make facing Valeria be one of the last things he wanted, knowing it could end in ridicule for him like it had for Jake, now that he was the team captain he wasn't about to lose that respect he gained by making the same mistake. He liked to think that he could beat Valeria fairly easy, but he wasn't about to take that gamble, not at all. Plus he really didn't want Valeria to bad mouth him to Emily either. She might not be on the girl's soccer team, being a cheerleader instead, but he knew the girls talked and he wasn't about to lose her and the clout scoring with a cheerleader got him with the guys over this. It just wasn't worth it.

"What an asshole, luckily I was here to protect you my sweet Jake, I'm getting mad just thinking about what other crap might have come out of that guy's mouth had I not stepped in. No one get's to pick on my boyfriend but me, or those with my explicit permission that is, but you do so love to get teased a little don't you Jake? In either case I think I deserve a big thank you for saving your ass don't I?" Valeria teased in a way more playful way than Tom had as she gently tapped her cheek, indicating that she wanted a kiss. Tom's words had been horrifying and hurtful, and while not hurtful, Valeria's brand of teasing was way more embarrassing, that while he was already dealing with the shame of needing his girlfriend to stand up for him rather than doing it himself. Especially as he realised that even if he had known this would happen, the outcome would have been the same. He was simply too embarrassed to stand up for himself, especially in the face of a harsh confrontation. It was embarrassing he had to be saved by Valeria so to speak, but in the end he was happy she had intervened. After all there was no telling what else might have been said and done if she hadn't.

Glad or not, that didn't make thanking Valeria any less embarrassing as he quickly got up from his seat, mortified about his lingerie potentially showing as quite a few people were looking at them since Valeria had grabbed their attention raising her voice towards Tom. An audience was the last thing he wanted right now, but having seen everything play out the people around them were too intrigued to really look away, desperate to see how this would play out, if he would really kiss Valeria on the cheek like she had demanded. Jake wanted to wait until they looked away, but he knew making Valeria wait was a bad idea. He didn't want her to raise her voice to him to force him into obedience and make him seem like an even bigger wimp. Closing his eyes in shame he planted a quick kiss on her cheek right where she had pointed and stammered out. "Thank you for saving me Miss." It made him feel like such a wimp, almost like a damsel in distress thanking her knight in shining armour in some stupid fairytale, an image he was sure a lot of the spectators imagined as well as a lot of chuckles were heard all around. He couldn't really hear exactly what they were saying, but he did hear some words, like wimp, pathetic, and worst of all even sissy.

That last one really got his attention, instantly making him think back to how his weekend had went, and even worse to what he was wearing right now. Had someone noticed? Was that why they chose the term sissy? It was probably just because of how much of a wimp he had just acted like, but still the idea that someone knew was terrifying beyond believe. No matter what the case was however his old reputation had just taken another huge blow in the eyes of the school, that much was undeniable as everyone knew who he was. This was certain to make it into all the gossip. "Hehe, you're most welcome babe. Now why don't you grab your stuff and tag along. You shouldn't be eating all alone, there's always room for one extra at my table and I wouldn't want my boyfriend to be lonely now would I?" Valeria exclaimed as she kept on waiting with her own tray of food, obviously not going anywhere until Jake got up with her.

With a deep sigh Jake eventually got a move on and just like that they were off to a table full of Valeria's friends which meant plenty of his ex-girlfriends. It was awkward to say the least especially with the secret he was hiding under his clothes, a secrets which was way too exposed for his liking. Even back when he had been his old confident self he would have avoided a confrontation like this after all the clubs were better hunting grounds, where he could take someone aside rather than having to constantly deal with them all. At least none of them looked angry or upset. If anything they looked weirdly amused and he wasn't certain how to feel about it, whether he should be relieved, or worried that Valeria had told them something about him and the nature of their relationship. He guessed if that was the case he would already know, but still. "Hello girls, I hope you don't mind Jake sitting with us today? He was sitting all alone and well I thought it was somewhat pitiful so I invited him over. I'm afraid he's had a slight falling out with his friends, so he might be sitting with us more often from now on." Valeria explained, instantly taking charge again while he awkwardly stood by and waited for their approval. The giggling that followed was nothing but painful. Clearly the fact that Valeria was expressly speaking for him wasn't lost on the girls either, or were his stockings showing that much?

"Of course we don't, there's a nice place right here." Stephanie one of his ex-flings spoke as she moved aside on the bench a little, making place for the two of them, a place right in between two exes. No matter where he sat down, he would have to deal with this, and as Valeria was faster only a place between her and Stephanie was left, Stephanie who instantly made use of the occasion by whispering into his ear. "I've heard Tom took over as team captain. Wish him good luck from me will you?" She chuckled while he could do nothing but groan. After the confrontation with Tom there was no way he was going to do that, hell even before he wouldn't have considered it, it was simply too painful, but he guessed that was exactly what Stephanie was after some revenge for ditching her.

It wasn't long before another one of his exes spoke up, this time about him and Valeria specifically. "So Jake, I've got to ask, why her. I mean Valeria is gorgeous kind and amazing, but I've never known you to stay with a girl longer than a night despite making so many of us believe we would be different. I would have hated for Valeria to get hurt like we did now that she's finally opening herself up to a relationship, so I'm happy, truly, yet I can't stop wondering. What makes her so different and why you have dropped the whole macho playboy act since being with her? I mean pardon my saying, but you've become kind of a wimp." She said as the whole table laughed over her calling him that to his face. There was nothing Jake could do about it other than blush, he didn't even know what to say that wouldn't betray his secret.

Luckily Valeria was once again right there to save the day for him as she scolded her friend. "Chloe, that's not nice to say, he's always been way more delicate than he has ever let on. Let's just say that that macho thing was just a front which I managed to see through. All he needed was a strong hand to show him who he truly is and I've managed to do just that, haven't I babe?" Valeria asked as Jake meekly agreed, calling her Miss again much to the hilarity of all her friends. He guessed it was the best explanation to give without giving away his secret, but then again that didn't make it any less painful, especially not since he thought that Valeria might be onto something, maybe he really was a sissy, he most definitely felt like one.

He had barely managed to get over the question and Valeria's reply for that matter when another one of his exes posed another horrid question. "Jake is it true what Valeria claims? That the two of you haven't had actual sex in all this time that you've been together now? I mean you were never even the sex on the first date kind of guy, but the sex right on hook up kind of guy. There's no way that you are in a committed relation without actual sex involved right?" She asked, half in disbelief, half amused as Jake blushed all shades of red being grilled like that.

"Well, you don't need sex to have fun. I mean sex is fun and all, but there are so many other things to explore next to it as well and I kind of want to explore those things first you know, ramping up to it if you will. Sex isn't really the foundation of our relationship, don't you agree babe?" Valeria quickly stated as she along with all her friends looked at a mortified Jake who could do nothing but admit it and back up her story. It was true, although with the amount of time he had spent with his face buried between Valeria's legs he wouldn't really say that sex wasn't a real foundation of their relationship. Valeria's pleasure definitely was, while his needed to be earned, but when you saw sex as pure cock in the pussy then they hadn't even come close to that. Tonight he would get his first blowjob ever since getting together with Valeria. He was glad that Valeria hadn't gone into even more details, but that did little to help with the disbelief and giggles from all the girls around as they made up their own mind about what other things Valeria might mean.

"In any case girls, let's stop grilling Jake and talk about something else shall we?" Valeria asked and much to Jake's relief the other's obliged while he got to eat in relative peace, no longer being really involved in their talks. Still the whole meal ended up being quite embarrassing as they talked about their victory on Saturday, about the clubs, about makeup, about clothes, about pretty much everything even about their boyfriends and sex life like he wasn't even there. It was painful to hear, especially since some of those boyfriends were some of his ex friends who got to do things he could only dream of at this point. It was a huge relief when the lunch break finally ended and he could go back to class. And luckily for a change Valeria hadn't taken him down to the bathrooms for some oral relief. Still he couldn't make up his mind of what was more embarrassing, being used once every lunch break, or spending it here with Valeria at the girl's table, enduring their occasional amused smirks in his direction, and all their to him embarrassing subjects or the way too intrusive, half taunting questions. He didn't like either, but he already knew this was going to happen again as Valeria didn't want him to be lonely despite him wanting nothing but some solitude during these stressful days at class.