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This story contains bondage, punishment, crossdressing, and forced feminization

When Owen woke up, he quickly realized two things. First, this wasn't the room that he had fallen asleep in, it was quite fancy any seemed to be in a mansion, or possibly a penthouse suit, judging by the view out the window. Second, he certainly hadn't been wearing a pink frilly dress when he had gone to bed... After a look in a nearby mirror, a third thing could be added to his realizations: His hair had been lengthened, and he was also wearing makeup, which meant that his mind's eye wouldn't be of any help at the moment.

He hopped out of the bed and nearly fell over, as apparently the dress had a hidden internal hobble skirt, then there was the high heels that had been applied to his feet. He reached behind himself to try to take the dress off, but while he was easily able to find the zipper, it refused to budge no matter how hard he tugged at it, and an attempt to take off the gloves was similarly futile, as they seemed to be glued to his hands.

"Do you like it?" A feminine voice asked.
"Who are you?!" Owen yelled back, trying to find where the speaker was.
"Well, due to a misunderstanding, my name is Ryouko. However, I asked you a question," the voice replied, as a short girl with pink hair and wearing a blue dress appeared behind Owen.
"No? Well, in that cause, I suppose you're just going to have to wear it until you do like it!"
"And if I did like it?"
"If that was the case, well, I'm sure I could come up with something even more impractical... But don't worry about that! I'll be sure to make the one you're currently wearing more impractical as time goes on, and you'll ask for it, as well!"
"Yeah, right..."
"Maybe not now, but you will. Anyway, this is your new home for the future... Eventually you'll be able to leave, but first, you'll need to get some guy to come rescue you!"
"You see, this place is located at the top of a very tall dungeon... wait, is it even a dungeon if it's above ground? Anyway, there's monsters and traps and stuff hidden all over the place, and anyone who wants to rescue you will have to make it through all of that first! Also, it does a very good job of keeping you from running off, as there's no way you'll be able to do a dungeon crawl in that outfit, with no weapons... especially considering the monsters and stuff up here at the top are the hardest ones, and any death will cause you to respawn back here, as the checkpoints are for the dungeoneers only, not the prize."
"This is a video game, and it's not a roguelike. Though then again, maybe it should be, at least for the dungeoneers, then it will take longer for them to make it to the end... Nah, there's plenty of challenge as it is, and they'll still need to restart from the beginning if they run out of lives. Also, you can take a look out the window if you like, though there isn't much to see out there, no point in coming up with a background for a game that takes place only within the dungeon part. The player won't even be able to tell that they are even above ground at all! Especially as the stairs to go up a level appear to go down instead, so they'll think that they're getting deeper and deeper..."

After slowly walking over to the window, Owen saw that the surrounding land appeared to be a mostly featureless desert, while the lower levels of the building had stone walls with no visible windows.

"Now, I'm also sure you'll want to know a bit more about the clothes that you'll be wearing during your stay here," Ryouko said.
"Why can't I take anything off?"
"Because it's smart enough to know just who's trying to take it off, and if its you who's trying it, the clothes will refuse to budge. Observe," Ryouko said, before grabbing one of Owen's gloves and pulling it off without any problem.

"Oh, that reminds me of something Wait here, I'll be right back!" Ryouko said.

Ryouko didn't even go anywhere, she simply flickered and was now holding a set of pink fake nails.

After pulling off Owen's other glove, Ryouko asked, "Now, do you want to wear these?"
"Oh, so you'd rather have your hair dyed pink?"
"If you want to wear the nails, please say 'Please Ryouko, let me wear the false nails.' Otherwise, I'll dye your hair... and then put the fake nails on you anyway."

Owen sighed.

"Well? I'm waiting."
"Fine... Please, let me wear the false nails..." Owen said.
"Ehh... close enough. Now, hold out your hands."

Owen slowly did so, and then Ryouko applied all of the fake nails before handing him his gloves again.

"See? I told you that you'd be asking for things. Now, I trust that you know what to do with those?"

Owen glared at Ryouko, before putting the gloves back on.

"Also, there's just one more thing before I'll let you get rescued. You'll need to be properly trained to act like a proper damsel, one of those things you need training in is how to walk properly! Whenever you're moving around, unless otherwise specified, make sure to have your elbows at your side, and your hands up in the air and out to the sides! Also, there's some special features of your outfit, such as a shock bit, which I'm activating now, it'll zap you whenever you aren't walking properly!" Ryouko said.
"Go on, move!" Ryouko said a little bit later after Owen simply stood there.

Feeling quite silly, Owen took a few steps, walking as Ryouko asked him to, before stopping again.

"Well, good enough. Just remember that you'll be needing to walk like that until you get out of the outfit, though it will remind you of that in case you happen to forget. Also, before I forget, you won't need to worry about going to the bathroom at all, the outfits specially designed to keep you clean if necessary, as well as to get rid of any pesky things that would otherwise need a toilet! So therefore, there's no reason as to why you can't wear it continuously!"
"Yay..." Owen muttered.
"Come on, you've got to be more excited about these sorts of things! Now, stay there for a bit, there's something else that I have for you, this time you don't need to wear it at all!" Ryouko said.

Once again, Ryouko didn't appear to go anywhere, instead a couple books appeared in her hands.

"Just in case you're wondering, they aren't for reading, instead they're for training," she said.

Ryouko then set one of the books on top of Owen's head, before it slid off and bounced off of his dress before hitting the floor with a thud.

"Gagh!" Owen exclaimed as his panties and bra suddenly zapped him.
"You have to balance it, not just stand there," Ryouko said, placing the book back on his head.

Owen grabbed it to hold it steady.

"You do know that that isn't going to work in the long run, right? How are you supposed to walk with your hands in the proper position when you're too busy holding the book? And you will need to learn how to walk without dropping it in the future. For now, I'll just settle for trying to get you to balance it while you're just standing, there's plenty of days left for the rest of your training."

After getting Owen to let go of the book and just simply balance it, he was able to balance it for at least a minute or so, at least when Ryouko wasn't pinching his butt, or poking at his breasts, both of which felt far too real to simply be padding. However, trying to balance the book while walking wasn't going very well at all, which resulted in quite a few zaps.

Several hours of training later, Ryouko finally got bored.

"Okay, that's probably enough of that for today, though of course you're free to train yourself as much as you want, otherwise I'll be back for more training tomorrow. However, before I go, there's just a short quiz I'd like to give you," Ryouko said. "Also, do please give your actual answers, not what you think that I want to hear."
"If you had a choice, would you rather wear this, or this?" Ryouko asked, holding up a pair of jeans in one hand, and a short pink skirt in the other.
"Uh, that?" Owen said, pointing at the jeans.
"Okay, next question. Same as the first, but with shoes instead."

Ryouko now was holding a pair of sneakers in one hand, and a pair of high heels in the other. Owen pointed at the sneakers right away, now that we wasn't quite as afraid that he would get zapped again.

"Third question. If you could take your clothes off an actually use to toilet normally, and assuming that you didn't need to poop, would you use the toilet standing up, or sitting down?"
"Fourth question. Do you want your breasts to be bigger, or smaller? Base your answer off of their current size."
"And finally, do you want to have longer or shorter hair?"
"Now at the end of each day's training, I'll be asking you the same questions, and just like now, I'll want you to give your true responses... that way I can tell just how well the training is going for you. Now, here's some food for your trouble," Ryouko said, before teleporting to the other side of the room and setting a fancy meal down on the table.

"How?" Owen asked, confused. "You've done that several times now... appearing, disappearing, and such..."
"Eh, I'm just stopping time so that I can go do something else, don't worry about it. Now, eat up, you don't want your food to get cold, now do you? Also, I didn't poison it or anything like that, what point would there bin in training you if I just ended up killing you later? Oh! The first challengers to the dungeon have arrived! However it will be a while before they can make it here, from there perspective they're just playing an ordinary videogame, but from our perspective, they're doing an actual dungeon crawl... or at least it seems real, if you ignore the whole magic and logistics stuff... Now, go on and eat, unless you'd rather go hungry?"

As Owen started to eat, Ryouko said, "Oh, by the way, tomorrow will mainly be bimbo training, or at least as much as I can do given the current situation. Have an enjoyable meal!"


Nearly a month later, after Ryouko had finally gotten bored of the various training, and after the first group was finally able to make it to the top/bottom of the dungeon, Ryouko came to give some final preparations to Owen, er, Rowena. While still technically male, several additional changes have been made to him over the month, such as giving him somewhat bigger breasts, earrings and other jewelery, and Ryouko had finally found an excuse to dye his hair pink. Additionally, the training... and Ryouko's shock pads, had their effect as well.

"Okay, it's almost time for you to go! Well, assuming that the dungeoneers can beat the final boss..." Ryouko told him.
"Oh, who are they?"
"Looks to be some nice muscular knights... and a not so muscular witch, though it's up to them as to who gets you in the end. Also, don't forget your standard damsel in distress equipment!"

Before Rowena could even move, he was fitted with a bunch of tape that both gagged him and prevented the use of his arms, along with adding a tape rope to him as well.

"Got to have some way of leading you out, after tall! Don't worry, you won't be zapped for not walking properly here... unless you want to be?"

Ryouko grabbed the rope, and led him into a room that he hadn't seen before that appeared to be a large arena, before pushing him over to a large, fancy throne, where Ryouko sat down in and waited, holding onto Rowena's "leash". They didn't have long to wait, as the knights and witch arrived almost right away... possibly due to Ryouko messing with time to speed things up.

"Congratulations, now here's your prize!" Ryouko said. "Also, there's no need to fight me, you've done well enough already. The elevator to get back to the entrance is right through those doors over there."

After leading Rowena over to the crew, Ryouko vanished. One of the knights carefully unwrapped the tape from around Rowena, while the witch magically checked the area for any traps.

"So, what's your name?" one of the knights asked after ungagging Rowena.
"Owh, uh, Rowena. Thank you for rescuing me from her!" Rowena said, before giving the knight a big kiss as soon as they were able to.
"It was my pleasure," the knight replied.
"We're clear in her, so let's get going, there doesn't appear to be any hidden treasure here, anyway," the witch said.
"Aside from Gorgeous here," the first knight said, causing Rowena to giggle.

Now the question is... just how long will Ryouko's training last?
While the food is safe to eat, there might be other things mixed in...

Now updated with an ending!

Also, the 2nd knight and the witch are partners, in case you're wondering.

:icononemesseduphero:'s reward from Leaci's Costume Contest

Owen belongs to :icononemesseduphero:
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TerraZero20 Featured By Owner Mar 16, 2017  Hobbyist General Artist
Quite an interesting story :3 Will there be more to this?
Lyhoko Featured By Owner Mar 21, 2017  Hobbyist
A bit more has been added at the end. (below the "----------")
TerraZero20 Featured By Owner Mar 22, 2017  Hobbyist General Artist
Nice touch :3
Lyhoko Featured By Owner Mar 16, 2017  Hobbyist
Probably not unless they ask for more. Also, right now I'm not sure of how to continue without it ending up feeling repetitive after awhile...
OneMessedUpHero Featured By Owner Mar 16, 2017  Professional General Artist
Owen: Oddly not the weirdest situation I've been in.
Soma: Personally I can't wait to see how she plans on changing your answers to those questions. If she plans on changing the way you think it could have unusual physical effects on us.
Owen: I wish I didn't have to deal with you when my minds eye is sealed.
Soma: Oh please, you'd be lost with out me.

OOC: Not bad, I wonder who'll reach the top first.
Lyhoko Featured By Owner Mar 16, 2017  Hobbyist
Likely someone who Ryouko feels is fitting and deserving of receiving a sissy as a prize... she does have control over the dungeon, after all...
OneMessedUpHero Featured By Owner Mar 16, 2017  Professional General Artist
I'd personally like to see where this ends up.
Lyhoko Featured By Owner Mar 21, 2017  Hobbyist
A bit more has been added at the end. (below the "----------")
OneMessedUpHero Featured By Owner Mar 22, 2017  Professional General Artist
A... relatively simplistic ending.

In answer to the final question, until a few aspects have been summoned and remerged, that should shake loose the programming, but that makeup's gotta come off first.
Lyhoko Featured By Owner Mar 22, 2017  Hobbyist
I wasn't really sure of how to end it, which is why I left it open to begin with. Also, it's a bit harder for me to write stuff involving other people's characters in detail...
OneMessedUpHero Featured By Owner Mar 22, 2017  Professional General Artist
Owen's personality is... highly prone to change, he was made that way so others could more easily write him, without worrying about getting his personality right.
Lyhoko Featured By Owner Mar 16, 2017  Hobbyist
An ending I can do...
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