Chapter 2
When Wednesday morning arrived it started out as a day like any other for both Jake and Valeria. Only today Valeria was more excited than she had ever been to head to css, The second of her two morning csses was shared with Jake and after that it was time for a brief lunch before the real fun could begin. After all the preparations she had made she couldn’t wait to put them into practice, luckily csses provided enough distraction for time to fly by for her. She had always been a good student and so paying attention wasn’t an issue.
Jake on the other hand while being none too worried had a much harder time than she did. His day like hers followed pretty much the same routine, but unlike Valeria he had to put up with some more teasing wherever he went. It made him think all the harder on how he might get lucky with Valeria which made his morning pass terribly slow. Obviously his usual strategies didn’t work on Valeria in specific so he needed a new pn to seduce her and repair the embarrassment of his loss. Every taunt and tease made him all the more eager to succeed, keeping him constantly distracted from css. Not that it was uncommon for him to be distracted.
Eventually the final css of the morning ended and Valeria escorted by some of her closest friends made her way up to where Jake was sitting at the back of the room. “Hey Jake, I’m going off to lunch now, so lets meet up at my pce in an hour? I hope you have managed to come up with a ton of ideas as I’ve been struggling a little, I have one idea that will just be perfect and a great success though. In any case. I look forward to hearing you out.” Valeria teased before walking right past him to go to the cafeteria with her friends, not even waiting for his reply.
The moment she was out of earshot his buddies instantly started snickering. “Yeah Jake I hope you have plenty of ideas as none of your previous ones worked to get Valeria in your bed. Surely this time it’ll be different though won’t it. I have to give it to you that she seemed in a way better mood than I’ve ever seen her in around you so at least you have that going for you.”
“Of course she does, I told you losing to her spectacurly was the pn all along, I think the trick to Valeria is just making her thing she’s better than you. You know like letting her ride that victory wave before letting her ride your dick. Once she’s on there I’ll just know she’ll be sold and never look at another woman ever again.” Jake cockily replied, he wasn’t so sure of himself, but his friends needed to believe he was, that his pn was working so they could accept it as a trick by him rather than an excuse for a catastrophic defeat.
Valeria had seemed way happier, so they guessed Jake’s pn had some merit to it at least. Not that that saved him from any further teasing as they too went to lunch. Jake made it a very quick short one as with an hour to go he really wanted to pass by his own dorm first. Once there he took a quick shower, shaved away his beard, put on a bck shirt with his jeans rather than a t-shirt and even some perfume. It was a look that had always worked well for him and if anything it might heighten his chances with Valeria a little more he guessed. Checking his look a st time and with only a few minutes to spare Jake left for Valeria’s dorm a couple of buildings over. He knew how Valeria was always rather strict and pnned so not being te was part of the good impression he wanted to make.
Jake was right on time as he knocked at Valeria’s door, putting up a bright smile in the hope it would impress her. In no time at all the door flung open to reveal the girl soccer captain, still wearing the same outfit she had worn for css, simple but beautiful, a pair of bck opaque pantyhose, bck knee high boots, a bck and whit checkered pencil skirt that reached her mid thigh and a form fitting white woollen sweater. “As promised I’m here as I don’t back down from bets and deals, I’m a man of my word. Can I also just say that you look magnificent?” Jake spoke confidently, trying to charm Valeria. He usually didn’t even have to bring out the compliments as he considered his attention a big enough compliment, as did many of the girls he slept with. For Valeria he wanted to go the extra mile though, not only had he been wanting her for a long time, his reputation now depended on it as well.
His attempt at charming her didn’t really seem to work all that well as Valeria instantly rolled her eyes. Eventually she stepped aside though to let him pas through. “Well I guess it’s a good thing that you don’t back down from a bet, and at least you are on time. In any case, come on in and make yourself comfortable.” Valeria dryly spoke, not even commenting on his compliment, let alone thank him. It made Jake slightly nervous as Valeria really seemed immune to his charm. Shit this better work or he’d remain a ughing stock.
Stepping inside he noticed that just like him Valeria occupied one of the best dorms the college itself had on offer outside of the privately rented out ones. It was a small studio with a double bed, a simple yet personal bathroom, a basic kitchen, a table and a desk. Not a lot, but definitely better than the ones which were just a bed and desk with a shared bathroom and kitchen. Aside from some plush carpets and lots of pictures with friends and family hanging all over the room was identical to his which he hadn’t bothered to decorate at all. It was also kept a lot cleaner at that. It smelled sweet and flowery, a sharp contrast to his room which smelled like stale beer and cheap deodorant, a remnant of the multiple small get togethers he hosted with his friends before they went out clubbing. Without exception there were open beers left behind sometimes longer than a day.
Despite the identical yout of their rooms Jake couldn’t help but feel somewhat awkward and out of pce anyways as he hesitantly sat down at the table. Valeria’s less than warm welcome definitely hadn’t helped at all and she remained all business as she took a seat opposite of him. “So Jake, I believe you have some ideas for me so we can boost our viewership? I have only one, but let’s hear you out first as I’m really curious to hear what you’ve come up with.” She instantly said putting him on the spot, not that she was pnning to ever consider his ideas, but she wanted to give him a chance at least.
For a moment Jake was a little lost for words, he hadn’t actually thought of that at all, having been too busy thinking about how to get into Valeria’s panties. He really didn’t want to look like a fool though and so he just spewed out the first thing that came to mind, guessing Valeria wouldn’t be happy if he had no ideas at all. “Uhm, well I was thinking that maybe if you went for another uniform, maybe something tighter, with smaller spandex shorts you would get a lot more viewers. I mean women’s volleyball is popur for a reason right?”
The words had barely left his mouth as he realised it was a bad idea the way Valeria instantly stared daggers at him. “Not a chance, we’re not some kind of eye candy. Neither me or any of the women on the team will sell their body for view, views from perverts no less. Besides I don’t even think such a uniform would be in accordance to the rules. I can’t believe you actually suggested such a gross thing.” She replied appalled and disgusted making Jake all the more desperate, this was not going the way he wanted at all.
“Uhm, well maybe you can buy little gadgets or trinkets with the team and distribute them among the crowds, people love gifts. I bet you’d have a decent crowd after some matches where the word gets spread.” Jake offered, trying to rectify his screw up, but given how Valeria was still looking at him he doubted it was working as intended.
“Nope, that won’t do at all, our budget is already too little to get everything the team needs in the first pce. There is no chance I’ll waste money on such silly things let alone that fact that I’m really opposed to buying viewers, we should make revenue out of them so hopefully our team can get some badly needed new equipment.” Valeria firmly stated, pushing Jake’s second pn right into the ground.
Fuelled by desperation Jake came with a third idea right as it popped into his mind. He really hope that this one would pass Valeria’s stern judgement, but he had little hope given her reaction to his previous two ideas. “What about some side line entertainment? I mean we have a mascot which works really well to rile up the crowd and create a good atmosphere, which in turn convinces more people to come to our matches? I can always try to ask him if he wants to do you girls a favour and provide some side line entertainment during a couple of matches.” Jake offered, hoping that Valeria would approve, and seeing how a big smile burst out across her face his hope only grew.
“You are definitely onto something there Jake, you see I pretty much had the same thought of you. Someone to rile up crowds and keep them entertained during breaks would be amazing. That hideous mascot you guys have going won’t do though, besides it’s not in our teams colours anyways so that really wouldn’t work. No I think it’s best for our team identity that we have our own mascot, something to recognise us by and I think I have just the thing.” Valeria said, jumping up as she headed for her closet.
A few seconds ter she emerged carrying the huge frilly pink monstrosity of a dress that she had gotten from CC’s. “I think this would make a perfect outfit for a mascot, I’ve always kind of hated how we have to py in pink. You can’t believe how many times we have been taunted with names like the pink princesses and such. Then again as much as I hate it, pink has kind of always defined our team so I thought why not just embrace it? Stick it to those who taunt us and make a very pink princess our mascot?” Valeria asked with a big smile, holding out the dress in front of her. Jake just looked at her in disbelief.
“You have to be kidding right Valeria? There is no way our mascot guy will ever agree to wearing that monstrosity. Hell the only pink thing he might be willing to put on is a pink panther costume for the joke of it, but this won’t work by a long shot. There isn’t even a big head piece to hide his identity, not that it would help. I don’t even know if I could convince a girl to put on such a monstrosity for the cause of our deal.” Jake instantly blurted out.
“Well Jake you were the one to agree to the deal and you basically agreed that this is a good way to get more viewers, hell you even partially suggested it yourself and I whole heartedly agree, some side line entertainment with a mascot will be a game changer when it comes to collecting a crowd. If you can’t think of anyone to put this on then that isn’t my problem at all. You were the one to agree to help us get a bigger crowd so I think it would be fitting if YOU helped us. I bet this dress suits you just fine and I’m simply sure that we’ll pull in big crowds if we were to advertise that you will py our Pink Princess mascot. Hell I bet our stadium wouldn’t even be big enough to fit the crowds, so unless you have a better idea, I expect you at our side line wearing this dress and the accessories for our game on Saturday.” Valeria bluntly stated as the shock on Jake’s face only grew.
“No way, you’re crazy if you think I would ever put that thing on. There is no way in hell, especially not if you expect me to prance on the field with it. I won’t embarrass myself like that, and least of all publicly. You can shove this idea of yours.” Jake replied strongly even a little angrily. Not that it impressed Valeria at all. She hadn’t expected him to just agree to wear this dress. In fact she had very much expected him not to want to wear it in the slightest, she didn’t mind, if anything it meant it was ready for the fun to start.
“Oh, okay, if that is how you feel about honouring your deals then so be it, I would happily listen to any idea that would be equally successful, but so far you have given me nothing to work with except for this very idea you now refuse to help out with. For once I don’t like to be right, but I predicted in our locker room that you are just a big pussy hiding behind an even bigger mouth. I can’t believe some of the girls even had faith in you, even some of those you hurt. Well I guess you’ll be disappointing them yet again, not that they aren’t used to it. You better get used to going down in our college’s history as the biggest pussy and coward that ever studied here though as plenty of people witnessed our bet, and I’m sure they will realise sooner rather than ter than nothing has changed and that you weaselled your way out.” Valeria stated with pyed disappointment.
Her words triggered Jake big time though as he could already see his now dented image after his loss to her fall apart completely. He’d be the ughing stock for the remainder of his college life and he sincerely doubted that with such a track record he would be appointed team captain again. Not only that, but his whole excuse of losing to Valeria on purpose would be destroyed as well. There was no way anyone would believe that he had seriously tried or achieved anything if he left her dorm not even an hour after first arriving. Shit he was so screwed, the prospect of going from the hero to the ughing stock in a matter of days being a prospect he truly feared.
Then again, if he put on this dress he would be a ughing stock as well, no matter what he did he would get screwed big time, it felt hopeless. He could very well imagine the stadium being packed to the brim and then some if Valeria were to advertise he was going to wear this dress. Every pyer on every team in their competition would certainly attend even if it meant they had to drive hours. Hell he was sure it would draw in way bigger crowds than even their highest anticipated matches so thinking of something that would rival those kind of crowds was nearly impossible.
Eventually he was just reduced to begging, hoping that would solve his problem, it might be a massive loss of face in front of Valeria. Then again Valeria wasn’t the whole school and competition, he really didn’t mind losing face in the privacy of her dorm if it could safe face everywhere else. “Come on Valeria, please be reasonable, I beg you. I’ll never hear the end of it if I appear at the side of the field in a dress, let alone a dress like that. There has to be another way in which I can honour our deal, please help me out here.” He pleaded desperately.
“But Jake, I think this is perfectly reasonable. You made a deal, this or something like this seemed like a good idea to both of us so that’s how you’ll honour our deal. Besides I bet one of my girls probably filmed our match. I’m sure that if we were to show everyone a video of how you lost and create a poll whether or not that means you belong in skirts rather than football shorts I bet everyone would agree. What do you think?” Valeria grinningly asked as Jake’s face dropped all over again.
He already knew what the results of that poll would be, making his predicament if he refused here that much worse. Not only would they tease him about being a sore loser and a coward for chickening out, if Valeria were to spread the idea of him in a dress then he wouldn’t hear the end about dresses whether he put one on or not. She really had him by the balls and judging from the grin on her face she knew it. This had all been one huge mistake, he should have never agreed to Valeria’s bet or her conditions, he should have just sucked it up and cut his losses, but then again he had really thought he would win.
“Unlike you Jake I’m not a complete bitch though, you see I am willing to compromise and save you from another public embarrassment even though you really brought it upon yourself and should live up to it. I am sure that we would have filled a whole stadium and then some if you were our mascot, but since you want to pussy out so badly I might be inclined to make a deal. It will take a lot of time to make up for such a loss of public we could have had and I guess it means we’ll have to spend a lot of time together, but I think I know a way you could make it up to the team more privately.” Valeria offered, acting a little reluctant which worked like a charm as Jake lit right up.
Jake couldn’t have hoped for a better offer, a solution that would save him from further shame, but not only that, spending time with Valeria in private would give his statements about trying to get in her panties so much validity. It was a way out of this horrid deal and a way to confirm his bull shit excuse to his buddies. Yet despite all that Jake remained a little hesitant. Knowing where these deals with Valeria had nded him he want to know just a little more. “That would be wonderful, but just how do you suggest I make it up to the team?” He asked a little suspicious.
Valeria couldn’t help but smirk, Jake was clearly learning, not that it mattered at this point. With his ego she was quite sure it would be an offer he couldn’t resist. “For starters you will make an announcement at the start of every game to consider watching the girl soccer team as well. I’ll be nice so I won’t require you to tell it is very worth it and that we are obviously a lot better than you guys as I beat you five to zero. If you want you can give them that bit of info though. I mean I won’t mind people coming to watch us because I am obviously the superior soccer pyer.” Valeria taunted.
“Secondly you’ll help us maintain our material and chip in with the guy’s budget where it is really needed I’m sure a little less bravado and spectacle won’t hurt too much compared to some of the things we have to make due with. Maintaining our material includes washing our uniforms unlike you guys we don’t have anyone to take care of that, we have to do it ourselves, for budget reasons and because the coach is an asshole who thinks that girls should know how to under and get used to doing it.” Valeria firmly stated as a smile broke out on her face as she was about to make her st demand.
“And st but not least I still want you to get into that outfit while you confess that I am the better soccer pyer and that you obviously belong in skirts. I got to enjoy my sweet victory somehow don’t I and this will just be the perfect celebration. Besides I do want some return on my investment in this outfit, I found it at a cheap costume shop and thought it would be perfect for a mascot. I just couldn’t pass it up the thing is we just never found a potential mascot, at least not until now. I wouldn’t want it to just wither away in my closet. Now these three things are the alternative and I won’t budge on any of the points. Either you give me all three, you py our mascot at one of our games, or I’ll have to make sure everyone knows what a cowardly loser you are.” Valeria concluded obviously the cheap part was a lie, but it made more sense than buying something outrageously expensive because it looked perfect for something even without an immediate use yet.
Advertising for the girl soccer team wouldn’t be too bad Jake thought, in fact it might even get him some sympathy from all the girls attending their matches, giving him even more easy pickings. Doing undry was a bigger issue, for one he didn’t know how to do undry himself and secondly he really wasn’t all that excited about having to do such dirty work. The fact that it would take up a lot of his time wasn’t anything he was looking forward to either. Then again to the outside world it would probably look like time he spent with Valeria which would be very beneficial to maintaining his excuse for losing. Maybe just maybe with some time to work her over he might even stand a chance. After all if he did all these things Valeria was sure to be impressed right?
The st part of her deal was what eventually bothered him the most. He really didn’t want to come even close to that stupid dress, let alone wear it. It was the only real issue he had with her deal, but since it would be here in the privacy of her dorm he guessed it would be the lesser of three evils. Wearing a dress for a minute sure beat the alternative of having to wear it at the side line of an overcrowded stadium or getting the reputation of the biggest coward there was along with teasing about how he belonged in skirts. It took him a moment to think over whether or not it was really better, but eventually he did speak up. “Alright, I’ll take your deal. Now can I get that stupid dress so I can get this over with?” He sighed preparing for the humiliation that was sure to come. It was a good way to show he was a good sport though which may in and of itself make Valeria warm up to him.
“Well well, colour me surprised, maybe you aren’t such a huge wuss as I made you out to be after all, maybe you do have a spine and can at least somewhat be trusted on your word. In any case, just let me grab that dress and the accessories. You can get changed in the bathroom, if any bit gives you trouble don’t hesitate to call for me.” Valeria eagerly spoke as she not only dug the dress back out of her closet, she also pulled out a whole matching set of lingerie, a pair of high heels, gloves and a tiara much to Jake’s shock.
“They came in a package, it was either buy the whole deal or nothing at all and I do expect you to wear every single item. I paid for the whole package, I want to see the whole package.” Valeria quickly expined as she shoved everything into his arms and pushed him out to the bathroom before he could put up too much of a fuss. It might be stretching the believable part of the excuses a little. Especially since the package contained panties as well and that the shoes would fit, the one thing she did know, for the other bits she would just have to rely on Linda’s guesses based on some pictures and his height. Still at this point Jake was probably shocked enough to have other things to worry about than questioning the details of the logic she was selling him.
In no time at all Jake found himself stuffed in the overly feminine bathroom, with his even more feminine outfit. Just like the simirities in their dorms the bathroom was identical, save from the fact that some pantyhose were hanging out to dry while the sink was littered with all kinds of beauty products? Not that either of those things bothered him as much as the current outfit he was left to deal with. Then again, it was either face this huge embarrassment in front of Valeria to please her or face way worse in front of everyone. It was just a piece of fabric, no one had to know and this would all be over shortly, he just had to push through this one for a brief moment.
A task that sounded a lot easier than it was especially when he noticed there were panties among the clothes as well, just as ridiculously frilly as the rest of the dress. Sighing deeply Jake started stripping out of his clothes, discarding them over Valeria’s bathroom floor before picking up the panties and cringing instantly. They looked god awful, made out of solid bright pink satin, with white ce trimming the edges, a white ce tiara shape sitting in the centre of the panty’s front and a big white satin bow fixed at the centre top in the back. For a moment he considered just discarding them, after all they wouldn’t be visible underneath the dress anyways, it wouldn’t hurt if he just put on his boxers.
Then again, if Valeria found out she would probably get mad and since they wouldn’t be visible anyways what was the harm in just sucking it up and wearing them? Jake thought as he stepped into the offensively girly garment. Much to his surprise the panties actually felt quite good, erotic in a way even. Their fabric was a lot smoother and pleasant to the touch compared to his boxers and it fit snuggly, rubbing against him in a sensual way. Then again, any positives there might be to these panties were overruled and destroyed by the sheer embarrassment they caused. Looking down Jake couldn’t help but blush beet red as he once again questioned what he had gotten himself into.
His shame only got worse as well as he moved onto the stockings. They were made out of solid white opaque nylon, with pink ce stay up tops. The thicker less refined nylons would look just as girly as any, only they were a lot sturdier so perfect for him to put on unsupervised. The opaque material would also hide all of his leg hair, and added bonus as Valeria didn’t quite feel like she could just tell him to shave.
Just like the panties Jake couldn’t help but admit that the nylons actually did feel rather good on his legs, a thought he instantly shrugged off as he just got himself in the main piece, the dress. It was a quite modest affair at least to CC standards, featuring a little bit of stretch in the material for ease of putting it on and adapting to an estimated size. At just above the knees, the skirt wasn’t too short and the rounded neck at didn’t have any cut-outs or cheeky revealing details. A dress perfect for the job it needed to do.
Despite all that the dress was still a height of girly delight. It was made out of solid pink satin, the hems trimmed with a wide border of white ce. White net petticoats made the skirt fre out dramatically while a broad white ribbon tied off in the back with a big floppy bow with long streamers decorated the waist. It’s balloon sleeves were ridiculously puffy ending just where his shoulders went over in his arms. The front of his skirt sported a big white ce tiara, one matching the one on his panties and the one that came with the outfit as an accessory.
Jake couldn’t help but feel like a complete fool dressed as he was. The titilting brushing of the petticoats over his nylon covered legs, feeling somewhat good and sensual wasn’t helping in the slightest either. He couldn’t help but feel like a pervert, liking the feel of these ridiculously girly clothes as much as he did, it was honestly worrisome for him as he simply couldn’t wrap his head around why he would like this in the slightest. In fact he firmly believed he shouldn’t.
Nearly fully dressed Jake only had a st few accessories to put on. First he slid on the gloves, like the dress they were made out of solid pink satin, reaching up to the middle of his upper arm where a white ribbon tied off in a floppy bow wrapped all around the top.. The tiara looked very delicate and bright with pink stones decorating the silver frame. Last but not least came the shoes. They were made out of patent pink leather with a five inch tall block heel that made him stand ridiculously tall. Two neat white leather bows decorated the tips of the shoes.
One look in the bathroom mirror confirmed to Jake that her looked as ridiculous as he felt. More worrisome however was the fact that between the gloves, the dress and the opaque stockings hiding his lean muscles, one could even mistake his body for that of a girl, at least if they didn’t see his head or height. The fred skirt hid his ck of hips, the ribbon in the middle created the illusion of a slender waist and the balloon sleeves completely negated his broad shoulders. It was shocking without a doubt. He dreaded letting Valeria see him like this, but then again he had gone through all this trouble and it was just the two of them. He might as well suck it up and push through now, hoping to score some points with her and above all avoid more public embarrassment, he thought giving himself a pep talk as he braced himself to go out of the bathroom.
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