Intro

 

Jake had always been a player at heart and he was blessed with everything he needed to get every girl he set his mind to. At 6’2” he was really tall, his chin length wild dirty blond hair and deep grey eyes had something mesmerising to them. On top of all that he was built rather athletically, lean muscle was visible all over his body. Having entered college on a sports scholarship and having made it all the way to team captain Jake had quite the position to woo the girls with as well.

 

He loved girls and they loved them. At least most of them did and usually not for a very long time. Jake just loved the hunt, he loved to sweep girls off their feet and bed them just because he could. It was always a thrill and a boost to his already massive ego, and although the girls knew him as a huge player many still fell for him, thinking they would be the one he’d settle for only to be proven wrong and be left with a broken heart. It was well known that he scored more off the field than on it which was saying a lot as the goal getter on his team. Both titles he was very proud of. He didn’t really care all that much about all the broken hearts as as far as he was concerned all girls knew what they were getting into.

 

While he was often charming to the girls who’s panties he was trying to get into, those who didn’t fall him could only see them as an asshole. Aside from his overinflated ego thinking he could score any girl, he was actually quite dismissive of women in general. He often preached how men where superior which was extra maddening to those women who already disliked him.

 

One of those who hated him most of all was Valeria, the captain of the girls soccer team. She had had to console way too many of her teammates who had much to her frustration fallen for Jake’s looks and charm. She had warned them all plenty of times and still it happened while all she could do was damage control. After all the last thing her teammates who had fallen for Jake needed was a scolding “I told you so.”

 

The fact that after having had to provide a shoulder to cry on for so many girls he had hurt, he still dared hit on her only made it more infuriating. Especially since she was openly bi leaning more towards women and she had heard rumours of Jake bragging that he would set her straight. Even if she dated a guy that still didn’t mean she suddenly wasn’t bi anymore and if she were to date someone Jake would be at the very bottom of her list.

 

It also really didn’t sit right with her how he preached his male superiority. She firmly believed in equality and while everyone had things they excelled in compared to others that didn’t mean one was superior or anything. She often complained that it wasn’t fair how only a fraction of the budget for scholarships, material and just about everything went to the girls soccer team compared to the guys team, that while they were higher in their leagues ranking than the guys team was.

 

Jake always loved to counter her complaints by pointing out how that was just because unlike them they played in a real competition, denying that the girls prestation were in any way comparable to the superior male competition. A point Valeria heavily opposed, but when he pointed out how they also drew 80 percent of the crowds to their college soccer field she hated that she had to agree with him. At least on that very hard to deny fact. It was something that had always bothered Valeria especially since a big part of the crowds they drew were only there to ogle them in ways that made her uneasy. She did maintain her point that their team deserved just as much respect and budget though, but she did in the end decide to just stop complaining. It didn’t accomplish anything except for causing her to grow frustrated. For her own well being she chose to just ignore Jake as much as she possibly could while being there for the girls he screwed over.

 

Valeria’s trick of dealing with all this was to straight up ignore Jake as much as she possibly could, but considering they used the same field, had some of the same classes and the fact that Jake always tried to hit on her made that really difficult most times. She was quite used to getting hit on and didn’t blame her for trying once. After all she was considered gorgeous by many.

 

At 5’1” she was rather small and overall petite, her figure more athletic than curvy. Still she did have nice well proportioned curves relative to her body, modest but firm breasts and a bottom. She had long black hair, so long that it nearly reached her bottom, a pair of magical hazel eyes and a blemish free tanned skin thanks to her southern European heritage. Most people luckily accepted her rejection rather quickly, it did help that she was always nice about it, but Jake was on a whole other level. Trying to be nice once hadn’t worked at all, he just kept on trying. She couldn’t believe Jake still thought he made a chance with her especially not since she had made it clear countless of times that she wasn’t interested and that she thought he was an asshole.

 

For better or for worse ignoring Jake was a relatively good tactic, until one day she picked up a rumour that really made her blood boil. Apparently Jake had a “to do” list of women, one literally hanging out in the open in the guy’s locker room. A list of special “prizes” he had his eyes on and each time he conquered someone from the list he treated the guys to a beer. The whole idea of such a list was the most unrespectful thing she had ever heard, but the worst part about it was that she was on it, and not just on it, but right at the top with a crown above her name. Apparently Jake had promised the guys multiple rounds at the bar if he could bed her.

 

She wanted to do so many unspeakable things to him and she wanted to do them so badly, but of course that wasn’t an option. For one it was illegal and she definitely didn’t want to go to jail over such an asshole and secondly he was way stronger than she was, there was no denying that. Men just had more muscle and he towered over her which didn’t do her any favours either. It was a fact she wouldn’t deny, but that didn’t mean or prove anything as far as superiority was concerned, a realisation that sparked an idea.

 

Shouting about his list or complaining wouldn’t help at all, he would probably even admit it and laugh it off before trying to hit on her right away. She could already imagine how he’d smugly state that she was welcome at the party he’d throw over it as well. She really didn’t even want to give him that opportunity. Instead a plan slowly formed to let his ego screw him over only to then crush said ego. The idea was delicious, and knowing how big his ego was it probably wouldn’t even be that hard to trick him into following her plan.

 

Chapter 1

 

Valeria had spent nearly a week thinking about and training for her plan. It was quite genius if she said so herself. All she really needed to do was trick Jake in a bet of her design, a bet she was nearly certain she would win, one Jake would think he would win for certain. The sweet loss would already be a great hit to his ego, but it were the stakes she was looking forward to the most. Stakes that would ensure that she could well and truly take down his ego on a more permanent basis. An idea that had formed thanks to the newest sorority on campus, Sigma’s CC’s. All she needed now was an opportunity to strike and she didn’t have to wait long for one to present itself.

 

Tuesday like always it was practice time for both teams. Each got one half of the field to do their training on, but like often times before Jake came over to the girls side about thirty minutes before the training ended. “Hey Valeria, if you wouldn’t mind, me and the guys want to play a small match on the full field to end our practice, so if you would be so kind to move the girl’s to the side lines that would be great. You girls can cheer or whatever, in any case I’m sure that you can learn a lot from how we play. I would dare say it can be as valuable as practice. I know you don’t like giving up your side, but you can go on a date with me for compensation? So what do you say? If you want more compensation we can even have some fun after our date, or I could go and ask the coach.” Jake smirked down on the way smaller girl. He knew she was unlikely to give in to a date, but he could always try just in case right? It was more of a demand for the field than a request anyways as the coach was pretty much always on their side.

 

Much to his surprise Valeria didn’t give him a whole lecture on how their practice was just as valuable as his was. Instead she just gave him a sweet smile. “Well I don’t know Jake, we are still higher in the standings than you guys, so maybe you and your boys should watch us play. I know what you are going to say, that the competition level is a whole lot higher where you guys are at, but humour me and let me doubt that. I would say there is only one way to find out who is the superior soccer player and that’s to test it out. What do you say? A duel between you and me to determine which gender is superior at soccer? Winner gets the whole field while the loser get’s to watch and learn. Let’s sweeten the deal. If you win I’ll go on a date with you, if I win you’ll come over to my place and help me give the female soccer team the viewership and respect we deserve. So what do you say?” Valeria asked loud enough for half the field to hear.

 

In no time at all, people on both teams standing closest to them, having overheard their conversation. Seeing the commotion more and more people joined until they were surrounded by both teams, the earliest ones explaining what had been said to those who joined last. “Deal! I hope you have a pretty dress ready for our date, unless you still want to back out and just give us the field that is, I mean I would feel bad humiliating you before we go out.” Jake smugly and confidently stated.

 

He didn’t look nervous at all, and even if he was he would never show it in front of this many people. After all he needed to put his money where his mouth was and after all his bragging about sports he couldn’t back down for a girl, not that he thought it was necessary. He was pretty convinced he could just take the ball and out run Valeria with it to the other side of the field. He really believed everything he preached including that Valeria would be lucky to get a date with him.

 

“Alright then that’s settled, let’s take this to the panna cage the first to 5 goals wins. After all you can’t just play with 2 on a field meant for 22 right? The panna cage is way more suited for a duel. Don’t worry though, we won’t have to go out on date so you better start worrying about your own humiliation as I certainly don’t mind making you bite the dust.” Valeria smirked, up until now everything had gone as expected and she was pretty certain that she could and would win. After all the panna cage was a rather small surface which would cut away his height advantage bending it to a disadvantage. Jake might be could with his game insights and running away with the ball, but her strengths were agility, she was very quick on her feet, directing the ball between just like she wanted. Her strength had always been out duelling to work herself out of a tight spot. The hardest part for now was biting her tongue not to tell him that she did have a pretty dress ready, only not for herself. That would just spoil the fun.

 

Suddenly Jake wasn’t as certain as he was before, the panna cage really wasn’t his strong suit. “Well we don’t have to play on the whole field, we can get one of those small goals from storage and play on half the field. It will be a way more genuine experience and test, besides it will be better practice than the panna cage.” He tried to haggle his way out casually under a ruse in order not to show his reluctance.

 

Valeria was having none of it though. The fact that Jake was trying to weasel his way out of this was perfect, it just proved that suggesting the panna cage according to her plan was the best thing she could have gone for. “What’s the matter Jake? Is my offer not good enough? The panna cage is perfect for a duel as I pointed out, this is of course unless you are scared of losing to a girl, but I bet mister hot shot would never fear such a thing right after all men are so vastly superior at sports aren’t they? In case you want to save yourself the embarrassment you can always yield the field to us and see me at my place so we can discuss how you’ll give us the viewership we deserve.” She happily retorted, not even hiding the mockery in her voice. Getting a good laugh out of the whole crowd.

 

It made it impossible for Jake to pull out despite his slight reluctance. His honour about all his claims was put on the line and he simply couldn’t let all these people just laugh at him, no he was going to show them how it was done and shut up all the laughter. Determined not to show he ever doubted himself in this he replied. “I just wanted you to get as much good practice out it as possible considering how you’ll miss so much when we’ll take the field, but sure, lets go to the panna cage.”

 

His statement was received by lots of cheering from both the guys and the girls side after all this show was way more fun than practice. Seeing these two who seemed to always go head to head battle it out was sure to be a spectacle no matter who would win. To them it was just a game while Jake felt the pressure to defend his honour while Valeria mainly cared about her plan who was going as smooth as she had hoped and predicted. Jake really couldn’t help himself when his ego was on the line and it was a joy to see how he was preparing for his own doom.

 

The moment they arrived at the cage Valeria was straight on the case to provide herself with yet another advantage. “ You know Jake, since I am a girl I’m already at a disadvantage aren’t I? I think it would be only fair if you would let me start no?” Asked innocently as she got into the ring and put the ball down at her feet. She could see it in his eyes that Jake really didn’t want to give over any more privileges in this area he felt less certain in, but feeling the pressure of the crowd he simply nodded.

 

Much to both their surprise the entire crowd except for one of Jake’s closest friends started cheering for Valeria. Her team would have obviously backed her up, but she guessed at least some guys were also fed up with Jake’s cocky attitude, or they were cheering for the underdog, in either case it was exhilarating to have so much support and she quickly made the crowd erupt in loud applause and whistling as she put the ball down and caught Jake completely off guard with the speed at which she acted, scoring one of the five points she needed within seconds. “Oops, looks like girls can be good at sport don’t you agree Luke? In any case, from now on it’s loser gets to start.” She laughed making the crowd laugh with her.

 

Jake didn’t handle the embarrassment well, he wanted to tell them all to shut up, but that would only making him look like a bigger fool. No he needed to show them who was boss, it was the only way to shut them up. Putting down the ball he tried catching Valeria off guard while she was enjoying the cheers and laughter, but she was quick to block his attempt, elegantly snatching away the ball when he tried to outmanoeuvre her only to score yet again.

 

“I’m just giving you a nice head start, after all it has to be a bit challenging right?” Jake retorted, trying to save some of his honour by playing it off like that, but it didn’t appease the crowd at all, in fact it only made them cheer and laugh even harder when the exact same thing happened again and Valeria made her third goal. On the fourth try Luke came close, but hit the side of the goal allowing Valeria to recuperate the ball and score yet again. His fifth attempt was one out of sheer desperation and frustration as he just shot at the goal as hard as he possibly could, hoping the quick shot would catch Valeria off guard, but she blocked it and darted her way to his goal again for her fifth and final goal. It had hurt a little, but the pain was well worth the result as the crowd went insane while Luke’s face went beet red, the horror written all over it.

 

“Well I guess that means the field is ours for a practice match, I prefer playing eleven to eleven though so we could still use a few guys to help reinforce our non starters. As for you Jake, feel welcome to tag along and watch from the side line, it can be good practice and god knows you can really use some good practice, I almost felt bad making that last shot… almost!” Valeria laughed triumphantly, using Jake’s own words against him as she simply couldn’t resist rubbing more salt into the wound. She picked only the guys who had cheered for her to reinforce the team leaving just Jake and his closest buddies to spectate. This couldn’t have gone any better. Valeria Had thought she would win, but not in such spectacular fashion as she made her way back to the field under loud cheering and praises.

 

The girls were already playing in two mixed gendered teams by the time Jake made it to the side of the field, completely dejected and humiliated. The fact that his buddies who weren’t allowed to play either were poking fun at him didn’t help one bit either, and while he much rather would have gone home and soak in his misery alone, he only feared that doing so would lead to more teasing as it would show he was a sore loser.

 

He was only half paying attention to the match though, what they were doing didn’t interest him in the slightest as even after his harsh defeat he maintained his view that guys were just better at soccer. All he really did was try to think of a way to save his reputation while his buddies kept on teasing. Jake was getting really frustrated and angry with his buddies, but then all of a sudden a bright idea popped into his head, a perfect explanation for all that had happened.

 

“Shut the fuck up guys, I’m just playing the long con, I don’t care that Valeria gets to play now. She wants my help to plan a way to get a viewership which given how they play will be very hard, meaning I’ll get to spend a lot of time with her. Even if we went on a date she would have probably done it to honour the bet, but no way that I would have had a chance. Like this I’ll have all the chance to work her over and finally bed her, you’ll see.” He said confidently, even believing his own plan. This might in fact make a great opportunity even if it hadn’t been intended, and he could even use to claim he had let her win. After all the shame a smug smile finally reappeared on Jake’s face.

 

Jake’s buddies still gave him grief that if that was the case, then he wouldn’t have had to let her win without scoring a single time, but he simply claimed it was all part of the plan to make her feel as good as possible. The better she felt the bigger his chances would be he explained. It was something he sorely wanted to believe himself as despite the façade, his ego was still badly hurting. No matter what he claimed he still knew that he had lost spectacularly, fair and square. Nothing would change that, but as long as others believed that had been his plan at least his reputation was saved.

 

Eventually the match the girls played came to an end and Jake who had been pretty much ignored for the duration got greeted by Valeria and the entire girl’s team along with the remainder of his team behind her. “So Jake, I hope that was useful for you, I hope you learned a lot so next time you can maybe score once. In any case, that was only part of the bet. Since neither of us have class tomorrow afternoon I’ll expect you over at my dorm so we can discus a plan to boost our viewership numbers as agreed by our deal. It would be a shame if everyone were to find out you were a sore loser who didn’t follow through on the bets he lost now wouldn’t it Jake? I mean I have plenty of witnesses so you better show up, isn’t that right everyone?” Valeria smugly asked, putting on a slight show for the audience around her just to drive Jake’s shame home a little further. It worked wonders as everyone laughed and cheered, agreeing with her as Jake’s face turned bright red once more.

 

“Tomorrow afternoon it is, I am not a sore loser at all, no need to worry about it. In any case I really need to get going right now. I still have things to take care off after practice.” Jake replied shortly, wanting to get away from this situation as fast as possible. Claiming that letting Valeria win to eventually get into her panties was his plan all along probably wouldn’t work out all that well for him right now, if she demanded a rematch where he did give all his effort it would probably have the same result. No his excuse was a perfect way to secure his reputation among the guys. Just going away now would avoid another humiliation that would render his excuse useless.

 

Valeria saw his excuse exactly for what it was, an attempt to flee this embarrassing situation. It was tempting to find an excuse to prolong his torment a little longer, but she decided just to let it rest instead. After all she had achieved everything she had hoped for today and more, she had never dared dream that she would actually beat him  five to zero, but it was delicious. “Bye bye then Jake, if we have some spare time I might even give you some soccer lessons if you ask nicely.” Valeria taunted as Jake made his retreat to the locker room.

 

Soon after he was gone the remainder of the crowd disbanded as well, after the intense training despite the fun they could all use a shower. In the girls locker room Valeria was a hero for defeating Jake, the guy that had hurt so many of them and of course for showing a guy his real place. Jake in the meanwhile was the object of ridicule when the remaining guys arrived in their locker room . He managed to quiet them down a little when telling them it had been his plan to get into Valeria’s panties all along, but they were only half buying it. just like his closest friends they couldn’t help but snicker a little pointing out that he didn’t have to let her score five times in order to lose.

 

Despite the taunting going down eventually, Jake was happy once he was showered and dressed so he could finally go home after this horrible evening. He may have brought it upon himself by underestimating Valeria and foolishly agreeing to her bet and her terms, then again what could he have done, it wasn’t like there had been any good other options as crawling back would have ended in just as much ridicule and that without the ruse he had now.

 

A ruse he now realised posed new troubles, in order for it to be believable he’d better manage to either actually bed Valeria, or at least spend enough time with her that it really looked like he was building up to something. It was the main worry when he thought of what tomorrow would bring, how he would bed Valeria or at least make it look like he had come close to getting a chance with his “plan” to lose to her. It wouldn’t quite rectify today’s embarrassment, but at least it would allow him to push it away with what he did best, bragging.

 

If Jake knew what Valeria had in mind for the long run he would have eagerly gone back on his word and just not show up, breaking the terms of their bet right then and there. As far as he knew no plan to boost the girl’s viewership could be that bad, it wasn’t even anything he thought about as it was something he thought they’d figure out together tomorrow. Let alone that it might fit into a bigger more elaborate plan Valeria had for him.

 

Back at her dorm however Valeria was filled with excitement as she made sure everything was ready for tomorrow afternoon. Jake’s shame today would be nothing compared to what she had planned out for him. It had been amazing already, taking him down more than a few pegs in front of everyone, but if she had her way it would only get better. Valeria thought as she looked upon the outfit she had gotten him, her plan “to boost their viewership”.

 

It was just perfect, pink, frilly and dainty. Something she guessed Jake wouldn’t want to be caught dead in which was exactly what she was betting on. Following the trail of the Sigma CC’s sorority to their main sponsor the CC boutique, Valeria had found a world of inspiration and resources for her plan to get rid of Jake’s huge ego by taking him down multiple pegs. It had simply been eye opening and down right delicious to see that odd store who had been way too over the top for her tastes was in fact a boutique for effeminate boys and sissies. Linda and her sissy stepson had been a delight.

 

The main downside was that the clothes were way too expensive to afford on her student budget. Just the lingerie would have made her burn through her entire party budget for the coming months, and that while she didn’t even know his proper sizes. Luckily Linda had eagerly stepped in to help. She had been most helpful eager to hear out her plan and make some suggestions. She had seemingly loved her plans for Jake and generously donated a complete outfit down to the panties and shoes to her cause With the promise to support her wherever and with whatever she could on the condition that once she had progress far enough with Jake she would take him right to her, a deal Valeria was all too happy to make as she had been planning to take Jake her down the line the moment she had seen what the store was actually for.

 

While Valeria considered herself a good person she couldn’t help but get a little excited at the thought of taking Jake down and getting him all sissied up, his huge ego crushed under layers of frills and bows. It would be justice for all the shame and hurt he had caused so many girls even those who he hadn’t bedded and ditched, just by spewing all his misogynistic bullshit all the time.

 

She guessed she had always loved being in control, which is one of the things that triggered her so much about Jake and all his bullshit. He seemed to take away the agency of women, denying them to be their own person as he basically condemned them to living in the shadow of a man. Oh she would love to turn the tables on him although she guessed that he would very much shine as his own person rather than being able to hide in any shadow at all. She guessed she would also be lying if she claimed that getting to play with a sissy wasn’t a turn on either. She had never really considered anything of the like, but the incredibly demure and pretty Stephanie had definitely awoken something in her she couldn’t wait to explore.

 

Not that she would have to wait much longer, she thought as she started stuffing the outfit in her closet for now, hiding it from view for the time being. With that she decided to call it a night as she slowly sunk into a deep sleep, dreaming of how Jake would react when she showed him the outfit. Tomorrow was bound to be such fun.

 

(If you liked this story and would like to read way more along with a ton of other stories then please check out my page on SubscribeStar: https://subscribestar.adult/fibaro I have ran into trouble with Patreon, but since SubscribeStar  doesn’t accept PayPall you can still follow me there, just make sure you connect your discord account to your Patreon account if you do so you don’t miss out on my content. https://www.patreon.com/Fibaro )