From Soccer to Sucker Pt. 02

The last 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 explained 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 similarities 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 lace trimming the edges, a white lace 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 lace 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 lace. White net petticoats made the skirt flare 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 lace 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 titillating 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 last 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 flared skirt hid his lack 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.