From Soccer to Sucker Pt. 03

Chapter 3

After finally working up the courage to head out of the bathroom Jake nervously opened the door and tried to take a step only to nearly trip in these very tall heels. A near trip that made him yelp in horror. If he were to roll his ankle in these stupid heels it would be a disaster, both for him and the entire team. They couldn't lose their captain now that the soccer season had well and truly kicked off.

His yelp alerted Valeria who instantly came rushing towards her bathroom only to break into a huge smile as she spotted Jake in the very frilly pink dress. It turned out way better than she had dared dream of as she crossed her arms and drunk in the whole look. "Well well well, don't you make a pretty pink princess? I think you would do great at the side of our field, I'm sure everyone will love you. If you want you can still reconsider. You can forgo all the alternative ways I suggested for honouring our bet if you agree to sign on as out mascot instead. I think everyone should get a chance to see just what a cute princess you make." Valeria offered with a big grin.

Jake was horrified, having someone looking at him. Even if it was just Valerie who had given him the outfit. Was so much more embarrassing than he had anticipated, he felt so degraded getting eyed up like that, and the worst part was that he could do nothing about it. There was no where to run, not that he could even walk in these heels and the outfit was exactly easy to take off right away. He could only really let Valeria have her fun. One thing was more certain than ever though, he really didn't want anyone else, let alone a whole stadium full of people see him like this.

"No fucking way, this is bad enough as it is, I am not wearing this anywhere near a stadium. Now if you'll excuse me, I'm going to change again. You've seen me in this stupid horrid get up so you got what you asked." A beet red Jake spat, as he instantly reached for the door, trying to close it, but Valeria was quick to stop it with her foot before he could, nearly making him trip again as the unexpected stop really affected his balance on these heels.

"I don't think so princess I still haven't gotten a good look from all angles and you still have a confession to make, so out into the room you go, but don't worry you can take all the time you need. After all I imagine for a guy like you any excuse is good enough to keep this pretty dress on for as long as you can. Don't worry though, you are always welcome to come play dress up whenever you wish. I wouldn't want to deny you your fun princess." Valeria taunted having way to much fun with this, probably even more than what was good for her. She just couldn't help it really. It felt so good to finally make Jake feel what it was like on the receiving end of all his inappropriate comments and actions.

"Please Valeria, just let me change first. I really can't get out of the bathroom like this, I mean I literally can't. I almost twisted my ankle when I tried. These stupid heels are way too tall." Jake said, still holding the door handle as he continued to cringe and squirm away in his frilly princess outfit. Valeria's persistent smirk locked on him didn't exactly made things easier as he did everything he could to avoid meeting her eye. Never before in his life had he ever felt this awkward or insecure. Like one of the shy girls he loved to conquer so much.

"No, changing wasn't the deal, you are going to give me a good look from all angles at that outfit and you are going to confess. Of course we wouldn't want our delicate princess to hurt herself, so of course I can help support you a little as you walk in your pretty heels. All you need to do if you want my help is ask nicely. You really should do that more often you know? Being polite and asking nice goes a very long way." Valeria explained as she could see Jake cringe even more. He was going to go through with this and she would make sure of it. After all it was pretty vital to her plan. She had hidden a few camera's in her room to get some back up an insurance in case she would need it.

Realising that she wasn't going to yield Jake gave in with a loud groan. "Alright alright, can you please help me so we can just get this over with?" He reluctantly asked as he awkwardly stood there in the door way of Valeria's bathroom, holding onto the door, but not daring to really move.

"Help with what princess? With walking into your pretty cute heels? Also I really don't like your attitude towards this one bit. You should be happy that you finally get to confess the truth to correct all those bullshit lies you've been spreading around about guys being so superior on all fronts and such." Valeria pressed on, pushing him just a little bit more. It was just too great of an opportunity to pass up on.

Jake felt mortified and hopeless. Did Valeria really have to keep pushing like she did? Fighting it seemed like a completely lost cause though, it only kept him in this dress longer. Given how far he had gotten her extra demands weren't that bad, at least not as bad as this dress. With a sigh he just yielded yet again, really trying to get this over with. "Could you please help me walk in these heels Valeria so I can make my confession for you." He spoke softly, hanging his head in defeat.

"Well of course princess, I would be more than happy to. Here let me help you. Just hold onto my shoulder and remember take small heel to toe steps, one foot in front of the other. It's easier that way." Valeria grinned victoriously as she moved right next to Jake, firmly wrapping a hand around his middle for support as she took a small step forward, maintaining her firm grip forcing Jake to follow.

Valeria's sudden step nearly pulled him off balance as he wasn't ready yet, but her support really helped him not to trip as he took a small step forward as well. It was awkward to move his feet heel to toe, like Valeria had told him to, but paired with her support he had to admit that it really helped. Step by step Valeria guided him deeper and deeper into her dorm room until she let go of him right in the middle, practically getting him stuck as he doubted he could move back to the bathroom without her support. Kicking the heels off wasn't really an option either as he strongly suspected he would fall in the process.

At least the walk here had been a very short one, not that it mattered much as it had really taken a severe blow at his ego. He had often wanted to walk with his arms wrapped around Valeria, but not like this, not to support him in heels. Even though there was no one around to see it, he felt like the one getting paraded around rather than the one doing the parading, showing off his conquests as usual.

Despite all the shame the walk had brought him, it had also provided an even bigger confrontation with just how good these materials felt. If the panties and stocking had felt good sliding into place, moving made them even more weirdly pleasant. He was horrified to realise that the constant movement, making the slick satin panties gently rub over his cock, paired with how the nylons felt sliding over one another and against the stiff netting of his petticoats, had given him an erection. An erection that confronted him with the one upside to this ridiculous outfit. The knee length skirt stood out so far that not even the biggest hardest cock would ever be visible underneath it. It was but a meagre consolation.

Completely mortified Jake just stood there as Valeria eagerly sat down and looked at him expectantly. She had moved him right in the centre of all her camera's making sure she would get plenty of good blackmail material on him. "Alright Jake, I'm waiting. Isn't there something you have been dying to tell me?" She asked with a big shit eating grin. Oh this was simply too precious and she was enjoying every second of it to bits.

"Uhm you are the better soccer player of us two Valeria, you won fair and square." Jake confessed nervously. The stress and the fact that he didn't know what to do with his hands, paired with how far the skirt stood out kind of subconsciously made him fumble with the hem of his skirt like a shy girl. He didn't even fully realise he was doing it until Valeria started laughing at him.

"Oh my god, that's hilarious, so fucking precious! What's the matter princess? Are you a little nervous? A little shy about your pretty little outfit, or having to confess to how you have been wrong all your life when you claimed how you were so superior at sports?" Valeria laughed as Jake noticed his hands and instantly stopped the fumbling, completely horrified of how that must have looked.

"Could you now please help me back to the bathroom so I can get changed, or help me out of these horrid shoes. I'm afraid I'll trip if I try to step out of them." Jake asked with a beet red face as Valeria carried on laughing. At least the worst was behind him now, helping the team out and making an announcement would be peanuts compared to this embarrassment.

His question only made Valeria laugh harder as she instantly crushed his hoped. "Absolutely not princess, your posturing was precious, your confession was completely lacking. You even forgot to mention how it must mean you belong in skirts. Since you obviously aren't very creative let me see if I can think of something for you to recited." Valeria spoke with a grin as she started thinking.

Jake was horrified, he wanted to protest, that he had already done enough, but as soon as he opened his mouth Valeria instantly shushed him. "Unless you are about to blow me away with a spectacular confession I suggest you shut up and let me think." Valeria instantly snapped, giving him a stern look until he backed down and just stood there, his hands going back to fumbling with his skirt for a second before he stopped shocked that he had gone to his skirt again.

For a moment all was quiet as Valeria was clearly thinking only for a big smirk to suddenly spread across her face. Now that she had Jake right where she wanted him, she really wanted to make the most of it, and the growing worry on his face as she smiled was just amazing. It would be good for him to feel worried for a change, finally he would have an idea of how she felt whenever he tried to hit up another girl, worried for the stated he'd leave her in after he had had his fun.

"I know the perfect little confession, it goes as follows. Oh Valeria, I can't believe how good a soccer player you are. You are obviously way better than I am, if not the best I know. Given how I always claimed that guys were so much better that must mean I'm the one who belongs in skirts, and clearly with how much better you are only the frilliest skirts would do. I decided to test my theory and I have to say it makes so much sense, I love my pretty dress. It truly is where I belong, thank you for making me realise by defeating me with such overwhelming results." She spoke as she watched the horror grow on Jake's face with every word. She might have gone a little, or well a lot overboard with this, but now that she had thought it up, Jake would follow through, she'd insist.

"Oh and since you obviously didn't know what to do with your hands and looked rather embarrassed about it, I thought of something for that too. You can just clap them all excitedly. I would say jump up and down while you clap them, but we wouldn't want you to hurt your ankles. Also once you are done I expect a bow of your head while pinching the hem of that skirt and lifting it up nice and high so I can check if you followed through on wearing EVERYTHING." Valeria concluded as Jake only became more horrified.

"Please Valeria, I can't, please don't make me do this, this is way too much." Jake pleaded mortified, just the thought of doing these things was making him shudder with embarrassment, let alone actually doing them. God how would he ever live this moment down? He didn't know if he could even try hitting on Valeria ever again as it would just make him think back to this moment. Sure he had thought that complying might give him a better chance, but he didn't know if he could muster up the courage to hit on her again after this was over.

"Oh really? And what part exactly can't you do? You can obviously talk, and if that's the problem I can show you how to clap your hands and raise your skirt, but I guess you also know how to do those things. In any case that's what I want and nothing short of that confession will do. You can take as many attempts as you want to get it right, and as much time as you'd like to get going. I really don't mind having a pink princess decorating the middle of my room." Valeria said with a big smirk as she just leaned back and relaxed, eyeing the nervous team captain with a self satisfied smile.

Jake didn't know what to do with himself, he really didn't want to say those words Valeria wanted him to repeat, or act like the complete fool she wanted him to act like while doing so. Still what choice did he have? This couldn't all have been for nothing, and they were just words right, not even his words. Reciting a few lines wouldn't make him as big a sissy as he felt like right now right? None of this defined him, he was just honouring a bet, that was all, no more no less.

At least that was how Jake tried to brace himself for what was definitely the worst embarrassment of his life, then again, every minute since Valeria had beaten him could have taken that title only over taken by the minute that came after it. Completely mortified he recited Valeria's words with an enthusiastic clap and a fake smile plastered across his face. When it came to lifting the skirt Jake hesitated, but eventually he slowly lifted it up until his panties and lacy stocking tops were on full display. On one hand he was glad he had decided to wear them as otherwise Valeria would have been mad and undoubtedly make him put them on anyways. On the other hand it was the most horrifying experience ever.

Before this whole thing Jake would have smirked at the thought of being in Valeria's room in nothing but his underwear. At least if that underwear had been his regular boxershorts. Revealing this horribly girly panties on the other hand was down right mortifying beyond anything he had experienced. Each time he thought things couldn't get any worse Valeria proved him wrong.

Even now she proved him wrong yet again as she instantly started laughing loudly, fuelling his shame further. Especially when she called him out for the erection he had already been confused and worried by. "Oh my god, look at you Jake, you really do belong in skirts big time, you're rock hard sporting a real tent in those pretty panties of yours. Haha the head of your cock even looks like it's wearing a matching tiara. God you're such a big sissy, sure you don't want to be a pretty pink princess more often? Your cock seems to disagree with you." Valeria fired a seemingly never ending stream of taunts as Jake lowered the skirt again, not that it helped him in any way by now, the damage had been done.

His erection had been entirely unplanned, but the moment Valeria had seen it she just hadn't been able to help herself but make fun of it. This was just too perfect, so much more perfect than she could have ever dreamed of. She had always liked the sensation of nylons on her legs and she figured that it must be the same for Jake, amplified by the fact that this was his first time experiencing that feeling, still she hadn't thought he would be able to get hard through all this shame.

While Jake might not realise it yet, the damage was so much worse than his bleeding ego. The surprise erection had also been caught right on camera giving Valeria even more fire power to make him walk in line in the future. There was no way he could pass his erection off as honouring a bet if these video's were to ever see the light of day. Especially if the clip was cut to just his confession and this. He would really look like he was having the time of his life and getting off on it all.

Right now though his only worry was Valeria's persistent laughter while he awkwardly stood there, stuck in place due to these horrid heels. When after what felt like ages the laughter finally stopped Jake instantly took the opportunity to try and end this once and for all. "Can you now please help me back to the bathroom and out of these stupid heels? I did everything you asked and this has gone on for long enough." He tried to sound demanding, but it sounded more like a straight up plea.

"Hahaha sure princess, my apologies. Just let me catch my breath first, there's really no need to get your panties in a twist. Although I guess that would be hard considering how your cock makes sure they are held out and stretched." Valeria joked, taking another minute to just laugh at her own joke while Jake remained right in front of her, just standing there beet red faced.

Eventually Valeria did get up though, she had had her fun, at least for now and it had been so much better than she could have ever dreamed of. "Alright princess, lets let you change shall we?" Valeria smirked, drying her tears as she moved right back next to him, wrapping her arm around his waist tightly to support him. It was much needed, but oh so embarrassing as he felt like he was some kind of bride walking down the isle when he was slowly paraded back to the bathroom, taking small heel to toe steps in these tall heels.

It was a huge relief when they finally made it back to the bathroom and by extension his clothes. "Alright Jake, just step out of those heels, now, I got you to maintain your balance. There we go. Now when you strip just neatly put the clothes over the edge of the tub will you? I'll be mad if you ruin that outfit." Valeria said as Jake eagerly stepped out of the heels, even this short wear had his feet aching slightly already.

Once he was out of the shoes Valeria just stepped out and left him alone to change, a welcome relief for Jake who finally had a private moment to lick his wounds. He was still shaking on his legs out of sheer embarrassment as he stripped out of the dress and lingerie as fast as he could possibly manage without damaging them. He really didn't want to make Valeria angry now that he had finally put this horror behind him.

Putting his own clothes back on, something normal felt absolutely great. He felt so much more comfortable now that he could just be himself again. Then again it also made it painfully clear how much rougher and unpleasant his clothes felt compared to the silky soft lingerie that had belonged to the outfit. Not that he minded that at all, the less confrontation he had with getting aroused by clothes the better for him.

Leaving the bathroom all he wanted to do was leave this place as soon as possible so he could try to forget about all of this and carry on as usual. It would take time to really get over it, but one thing was certain, he wouldn't show it as no one could ever know what had gone on in here. The only upside to all of this was that he had been here a long time lending credit to his ruse of trying to conquer Valeria through losing that bet. "I really need to get going now, bye!" He shouted out, as he went for the front door, unable to muster up the courage to appear in front of Valeria right now.

After all this fun Valeria wasn't just going to let him leave quietly though. The moment the door to her bathroom had opened she had jumped up to meet him one last time. "Bye bye Jake, have a nice day, I have to admit, you looked a lot better in that dress and I guess you have to feel the same way as I can't see a tent in those pants of yours. In any case, if you or that cock ever feel the dire need to be pretty again you can always swing by to try on your dress once more." Valeria laughed while Jake ignored her and just rushed out, having no comeback to her taunts. All he wanted to do was get back to his dorm and stay there.