It's very varied to say the least. But it won't be so easy.

Emily had gathered 5 piles of items that could technically be considered outfits and had laid them out for K-T to pick from them. He honestly couldn't believe his eyes, looking at the eclectic pick ranging from reasonable to horrifying, while passing through ridiculous.

The most normal looking one was the t-shirt he had picked and a pair of yoga pants, which while technically being made for women wouldn't look that weird on him the pile looked too big though and K-T wondered why his sister had even offered the other options if this one was available.

The second option was something K-T had only seen in old western or period movies or shows. It was this very old looking washed out, red full body, long sleeved underwear one could see in cowboy movies, with buttoned up flaps on the front and back to use the bathroom without having to remove it. Not only was it ridiculous, it looked way too hot for summertime and it was meant to keep someone warm under other clothes, not worn as is.

The third option was a gay pride crop top, pink with a rainbow on it and cut off to leave all the midsection visible. With it was a pair of neon green mesh short shorts, with no underwear, the fabric would stretch if worn and his nothing of his butt nor the prison constraining his cock.

The fourth one was the one with the most items and K-T would bet that his sister had probably gone over budget on this one. There was some sort of black corset with built in padding to the bra that would make him look like he had tits, a gold micro skirt with sequins and a red g-string. The part that convinced K-T that his sister went overboard was that there was also a pair of high heels in a size that looked like it could fit him.

The fifth and last outfit like the second was a single item but this one could barely be called an outfit. From part of the clientele and what he saw on the racks a good chunk of the inventory of this store seemed to be used stripper clothes or stuff cheap prostitutes would wear, because he couldn't imagine anyone else wear or buying new most of what he was seeing. The offending item was some sort of modified leotard like those worn by female gymnasts. Except for the fact that the cleavage was cut so low it stopped an inch above the crotch area, the back would go right between his buttcheeks and leave his back bare except for a strip of fabric, the side were missing as well up to leaving the armpits bare. The end result almost looked like someone had added long sleeves to that ridiculous swimsuit from the Borat movie and somehow it was the exact same color as his cock cage, which would pretty much be the only part of him it would cover except for his arms.

"OK Emily, why even bother? It's pretty obvious that I will pick the first one. You didn't have to bother looking for the rest of the stuff." he told his sister.

"Not so fast dear brother. There are conditions attached to each outfit."

"What do you mean? You said I could just choose one."

"Yes and you owe me a favor, so I'm making the choice more interesting using it. Do you want to hear the conditions?"

"Yeah, yeah, go on. It was stupid of me to think you'd act like a nice sister for once. What did you come up with?"

"Let's start from the end. This one is almost a freebie, no strings attached, one item, you choose to wear or not wear it whenever you want. You just can't try to get any other clothes until you get your uniform and go to college, but it's true for all outfits." She explained.

" I wasn't going to pick that one anyway, next! "

"Next one is pretty complete but you have to let me pick how you do your hair and wear the make up I will choose for you, as well as wax your whole body except for your head. You got to look the part if you wear that." She taunted him. After all that hub hub about him being forbidden to crossdress at his new school ending up with his dick locked, his sister now wanted him to live as a girl before joining.

"Not really what I was going to go for anyway, what with the next one?"

"This one is pretty easy. If you wear that you can't deny being gay and have to actually say that you are if asked. And you have to come with me to any outings or party I want until we go to college." She replied. K-T wasn't really sold on that one, not only did it hide pretty much nothing, he didn't know where she had planned to drag him to humiliate him further.

"Very funny, must have been hard coming up with that shit. What about that? I want to get to the one I want before more people see that I'm naked." he told her pointing to the old cowboy underwear, knowing that she would keep the more reasonable outfit for last.

"This one is so easy even you can't mess it up. Once you put it on, you can't remove it, not until you get your uniform and go to college. There are flaps for easy access, but if you want to clean it or yourself you will have to do it wearing it. But at least you will be perfectly covered at all times, isn't it what you want? " she asked with a smile. Wearing this thing day and night for weeks in the summer heat would be **** and was sure that he wouldn't be allowed to just find a cool spot and laze all day for weeks. It would be very awkward to go do anything outside wearing a ridiculous, smelly and sweaty outfit.

"Out with it. What do I have to do to wear the real outfit?"

"I'm pretty sure that you thought those two items were the best of the lineup, but I'm not sure you will like the third item I bought from Hope. It goes with the yoga pants, it's a spiritual item that will open your Chakras through the power of crystals. You will have to wear it or it's replacement I will choose until I think that your attitude improved enough for me to disolve this." She said, pointing at her necklace in which the key to his cock was trapped. She lifted the clothes and K-T discovered what the bump that made the pile too big was.

There was a clear resin butt plug under it, with weird metal marbles and crystals set inside of it. His sister sealing away the key was proof enough that she had no intention to free him anytime soon, but her wording meant that she expected him to wear the plug maybe even beyond them joining the school.

"You can't be serious, I can't wear that in public!" he protested.

"Says the naked dude in a cock cage. And you would be wearing nice covering yoga pants over it, silly boy." She corrected him. "So, now that you know everything you are free to choose. What will it be?"

K-T soon realized that there was no clear. better choice. The ridiculous last one that he had ruled out from the start was almost looking like the least worst one due to its lack of further traps.