St. Olga's School for Wayward Princesses doors were opened in response to all the young ladies who wished to express their independence. It was presented as a place for parents to leave their children so that they may skip all that hard work of grooming a rebel into a proper heir and instead focus on running their kingdom. Every king and queen considered it a miracle in education, while every princess knew better. "Saint O's" was quickly rumored to be a place of pure terror for any young woman that wished to keep her own identity. Less a school and more an institution of brainwashing. Where you went in a person and came out a perfect doll to be placed on a throne. A "Princess Jail".
Naturally the worst of the worst princesses were the first to end up in such a place. Girls that had more in common with violence and thievery than manners and education. To this day Saint O's was the first solution to the most problematic of princesses. And like any good jail there were girls that ruled over others before they were considered reformed enough to be placed back among society.
One such barbaric young lady was sitting on her bed, chewing on the end of a candy cane and glaring at her cell door. She knew there was fresh meat coming in today and was ready for a new cell mate. A girl she could boss around and make into her little handmaid. Saint O's tried to beat you down and the only outlet for such stress was to beat someone else into submission. She couldn't wait to take the scared little princess under her heel and user her how she saw fit. When the door opened she sat up and gave her new cell mate a good once over; a pretty pink dress, long brown hair tied in a pony tail and a cute face to boot. The kind of girl that enjoyed beautiful things but liked to have it all her own way. Spoiled brats were the most fun to bully.
"So, you're the newbie are ya?" The wild princess said, biting through the hard candy that had been in her mouth and eating it up. "Welcome to your worst nightmare, goody-two-shoes. You're in my world now and everything I say goes." She walked up to the princess in pink and got eye to eye with her. "You following me, Pinky?"
"Star, I feel ridiculous." The princess in pink sighed.
"Marco, you said you'd play along with me!" The once wild princess whined in the most girly of fashions. Marco rubbed his eyes and let out a deeper sigh. It hadn't been that long ago that he and Star had invaded the real St. Olga's School for Wayward Princesses to rescue their friend (well, Star's friend anyway) Princess Ponyhead from the actual brainwashing practices of the facility. To infiltrate the building Star had used her magic to craft two disguises for them. Her own was a black, lacy bodice with matching gloves and a green poofy skirt held up by suspenders. She'd accessorized it with grey striped tights, spiky boots, a demon horned headband and a black eye-patch to pull it all together. Marco's costume was considerably more simple and princess like; a pink poofy dress with his hair extended into a pony tail. Truth be told it looked really cute on him, despite his complaints while wearing it.
"I never should have let you watch those prison break movies with me." Marco groaned, giving into her request. "Fiiiiiine. Let's do this thing. But I don't want to be in this outfit for too long. It's soft but kind of stuffy." After their dramatic jail break at Saint O's Star had requested they have a little fun in their costumes before she used her magic to remove them. Even if Marco seemed reluctant to play along he was still giving into Star's request for her sake. He really was her best-est friend ever. When he agreed again to play along with her Star giggled happily and smiled wide.
"How about this then, we'll put it on a time limit. That way we can play for a bit but we don't have to keep doing it all day. Would that be alright?" Marco thought it over before finally nodding in agreement.
"Okay, just don't make it too long." He replied.
"You'll have so much fun you won't even believe the time has passed." Star said confidently and went over to her desk, grabbing a small hourglass and placing it on the night stand by her bed. "Great! Now that that's out of the way I have to get back into character." Marco rolled his eyes but waited as Star turned around and adjusted her expression. Turning back she had on an arrogant grin and looked him over once more. "Hope you don't mind getting cozy, cause we'll be sharing this cell for a while."
"Yeah, really looks like it's gonna be cramped." Marco said sarcastically, looking around the spacious area that was Star's bedroom. "So what do I call you? Princess Horn Head?"
"That would be insulting to the real Princess Horn Head, don't you think?" Star thought a moment. "You can call me... Princess Badnikki!" She felt pretty proud of herself for coming up with that name on the spot. Had the right amount of naughty mixed with girly. Marco however was covering his mouth and stifling a laugh before it came out to break the mood.
"Princess... Badnikki?"
"Got a problem with it, toots!?" Star asked, poking his chest with her finger and Marco managing to keep from laughing but not from smiling.
"No... no no. It's all good... I mean bad... nikki." Star was glaring at him and Marco realized it wasn't an act so he straightened up. "So uh, what are you in for, Princess Badnikki?"
"I kidnapped a prince and locked him in a tower with a dragon guarding it." Star said with an almost-but-not-quite evil grin. "Then I ransomed his family for enough gold to start my own underground soda bar."
"Wow, you do sound like the baddest of the bad." Marco said, finding some real amusement in Star trying to act like a villain.
"What about you, Pinky? What are you in for?" Marco stopped and tried to ponder a fitting character background while Star waited to see what he could come up with.
"Me, I uh... ran a gang of monsters? Yeah, I ran a gang of monsters! And we uh... robbed other princesses of their treasure! Then I kept it all for myself." Marco said, proud of his last minute improvisation skills.
"Oh, really? A pink powder puff like you lead a gang of monsters?" Star said trying to keep her bad girl persona going despite wanting to laugh in amusement over his story. "And how'd you get them all to follow your lead? Did you karate kick them into obedience?"
"Nope." Marco replied and struck a pose. "I just used my girlish charms to woo them into taking my orders." He then winked and blew a kiss Star's way, the princess feeling a hard thump in her chest when he made the motion towards her. Honestly he was doing that way too well for someone insisting to not look as cute as he did.
"Uh... y-yeah. Those princess charms, they'll get people to do anything for you." Star gulped and tried to get her composure back, feeling silly that he'd caught her off guard like that.
"Exactly, so you don't mind me taking the comfy bed as long as we're in a jail cell together, right?" Marco said and sashayed his way right past Star, sitting on her bed and claiming it for himself.
"Hey! Marco, I was supposed to be the domineering bad girl and you were supposed to be my lackey." Star complained, breaking character for a moment. Though it didn't seem to bother him as Marco picked up the hourglass which while was never specified how much time was set for them to play was far from running out.
"I'm sorry dear, but I don't know who this 'Marco' person is. Last I checked while this was running I was Princess Pinky and you were Princess Badnikki, right?" Star pouted and crossed her arms, annoyed that Marco had turned her game to tease him right around on her. "Now why not ask the guards to bring us some tea and snacks, I'm positively famished." He was falling into this roll well so Star decided to up her game to match him. Marching over to her bed she leaned forward to get eye to eye with him.
"Alright Pinky, we'll play it your way. So this is how it's gonna be; I'm the boss and you'll do whatever I say. Got it?" In reality if Star had really wanted she probably could beat mark to a pulp, but even pretending to be mean to him was more difficult for her than she anticipated. Not that Marco was bothered, instead he turned his head away and mimed a dainty yawn at her threats.
"I'm starting to wonder if you're less of a misunderstood bad girl and more of a proper, safe lady." Marco said teasing her further and grinning wide, really enjoying being able to pull one over on Star like this. She wasn't about to give up though.
"Alright then, if you need convincing then I can provide it to you, Pinky!" Star said through gritted teeth as she cracked her knuckles, not sure what she was planning to do but was determined to get him to cry uncle to her by the end of this. Grabbing the front of Marco's dress she pulled him forward only to have her path interrupted when he reached out and held the small hourglass in front of her.
"Time!" Marco said smugly. "Timer ran out, looks like Princess Pinky and Princess Badnikki are gonna have to tussle another time. Well I'll just be changing into my-" Star snatched up the hourglass from Marco's hand before he could finish, flipping it over and sitting it on the night stand with an audible thunk as the wood collided. "Uh... S-Star?"
"Name's Badnikki... and as far as I can see that hourglass is still running, isn't it?" She kept a tight hold of the front of his dress, Marco sweating now and nodding to her. "That's a good little Princess. You didn't want to get out of that pretty pink dress any time soon anyway, did you?" Marco shook his head. "You like princess outfits, don't you?" Marco glanced downward at his own, and then at Star's. In fact his gaze lingered on her own dress for a while. She noticed his eyes seemed fixated on the black, lacy bodice over her chest. The dress did accent her chest slightly, drawing one's eye to the small curves that just covered her breast. It was a little more daring than the kind of outfit she normally wore and seemed to hold his attention. "Seems you really like mine, don't you Pinky?"
"I... I'm sorry! I didn't mean to stare!" Marco said realizing what he was doing and looked away suddenly.
"What's the matter? You want a peek?" Star said, getting more into her tough girl character as she teased him. Reaching up with her right hand as her left kept a grip on Marco's dress, she pulled at the top of her bodice to almost reveal but not quite show off her chest underneath.
"I wasn't... trying to look at... anything." Marco gulped and his face was blushing now, exactly the kind of position Star had hoped to put him in. She just hadn't expected him to actually stop her earlier with his own looks.
"Oh I can tell what you're all about Pinky. You're the kind of princess that likes to pretend she's all proper and safe, but deep down you're really a misunderstood bad girl."
"Yeah! I mean, no! Not like this, I mean..." Marco's head turned to see Star was still teasing him with pulling at the top of her dress and he turned his head away again. "This can't be what Princess Jail is actually like."
"Oh no?" Star asked and stood up suddenly, using both hands to grab a hold of Marco now. Using her strength she tossed him onto his back on her bed and jumped over top of him, grinning devilishly appropriate for her attire. "You ever heard of girls hitting their Saint O?"
"I... uh... no?" Marco said nervously though it seemed like he had a good idea of what she meant.
"Girls get bored when they're all alone and have nothing to do. So we gotta entertain ourselves somehow." Leaning down on her hands and knees, Star leaned in and pressed her body against Marco's, still smirking confidently. "So like a good cell mate, we help each other hit our 'Saint O'. Get it?" Star said with a wink.
"Are you trying to wink at me? Because that doesn't work too well with an eye patch." Star suddenly realized her mistake, lifted her eye patch so she could wink at him anew, and replaced it over her eye. Marco rolled his eyes. "You gotta be kidding me."
"There a problem with it?" Star asked and grabbed a hold of Marco's wrists, holding him down on the bed. He panicked for a moment and tried to lift his hands but she managed to over power him and keep him pinned. "It's every princess' initiation in here."
"But we're both girls, that's forbidden love!" Marco exclaimed in a panic, then thought it through for a moment. "No wait... no yeah, yeah! That's right."
"Silly girl, we're wayward girls. Forbidden is what it's all about." Keeping him held down Star leaned in and kissed Marco on the lips, freezing him in place before causing his body to relax and kiss her in return. His arms stopped trying to fight back against her grip and he began to accept her over him. It lingered for what felt like a long time before Star pulled her lips back with a seductive smile. "Do you have a problem with it now?"
"No." Marco whispered in return.
"Well... too bad." Star said with a devilish smile and grabbed hold of the small hourglass. "Time's up! Guess our little game is over. I suppose we should change into our normal clothes and head on out of here to-" Marco's hand reached up and gently took the hourglass from her. Flipping it around he placed it back onto the night stand and looked up at Star. "That's my girl."
"This is so embarrassing." Marco said in return, looking away. Star felt that thump against her chest again and leaned in to kiss Marco's neck, the boy tensing up under her. "S-Star!"
"Wrong name." She whispered, keeping him held down and placing light kisses along his neck and up to his ear. Marco squirmed under her from the affection and she enjoyed it immensely. Something about role playing like this was really making her excited.
"I feel silly saying the other one." Marco groaned through her kisses and Star moved her head around to catch his lips, giving him a more aggressive kiss than before. Their mouths opened and tongues slid against one another before she broke it again, keeping him held in her grip all the while.
"Say the right name, Pinky. Or I'll just keep teasing." Marco looked up at her with frustration and Star smiled excitedly.
"Fine... Princess Badnikki." There was annoyance as he said her name but Star didn't mind.
"Now, ask your highness for me to give you your first Saint O." Star said and released his wrists from her grip, slowly sliding off her suspender from her shoulders. Marco was watching her intently and swallowed a lump in his throat before speaking.
"P-please give me... my first Saint O. Your highness." Marco covered his face with his hand and groaned. "I feel so dumb."
"You're about to feel something." Star said confidently and got off of him and then bed. Turning around she backed up to him. "Undo my laces would you, Pinky?" It might of felt silly but being in character was really helping her along and Marco was becoming more accustomed to her as she pushed him into it. Once he had sat up and untied the lacing on her back, Star wiggled her hips and slide her dress down her legs and off of her body. Standing now in just her tights and her gloves Marco blushed as he was fixated on her exposed chest before him. "You look ready for some forbidden love, alright." Star said with a giggle.
"I uh... I'm just... you look really good in that outfit." Marco admitted and Star held down a powerful "Awww!" that wanted to escape her right now. Instead she kept to her character, approaching him and placing her hands on his face to pull his gaze to hers.
"You might be surprised to hear this Pinky, but you do too." Star confessed in return and kissed his lips, enjoying the contact it provided them. When their lips parted again Marco spoke.
"The... the hourglass." He mentioned, pointing to the small glass vial that the sands had already run through. Star reached out for the small time keeper and threw it across the room into a pile of stuffed animals she'd left on the floor.
"Any complaints, Pinky?"
"Not a one, Princess Badnikki." Marco replied, fully committed to whatever she wanted now.
"You'll be calling me your queen by the end of this." Star said with a wicked grin that looked as if it made Marco's chest flutter. She enjoyed having that kind of power over him for once. "Now I'm going to show you what's fun about big gowns like these."
"What do you-" Star suddenly went onto her knees and flipped Marco's dress up where he sat at the edge of the bed. "Whoa! Hey wait a minute, isn't this-" He was stopped short again as he felt something being taken from him and Star tossed aside his boxers from out under his gown. "Aren't we moving kind of faaaaast!?"
"Oh my, look at what you smuggled in, 'Princess'." Star said in amusement as her fingers gripped around Marco's hard cock. The fact he was in this state wasn't too surprising after all of the teasing she'd done to him. "With something like this you're bound to be the most popular girl here."
"St-Star, wait, we've never done-"
"Wrong name, Pinky. Remember?" Her fingers and thumb ran along the length of his cock, making Marco groan in response. It was true she hadn't actually seen THIS much of him before but by now she felt comfortable enough with his body to let herself get close to him. Besides, this wasn't them doing this. It was the seductive Princess Badnikki and the perverted Princess Pinky. At least that made it okay in her mind.
"Y-yeah, okay, I got it. Don't use the wrong names."
"That's a good princess." Star said from under the skirt and stroked Marco's cock further. Her hand went up and down it slowly, feeling his skin and examining it from the dim light she had under the poofy dress. She hadn't known what to expect but it wasn't bad, just different from anything she'd seen before. "Does it... feel good?" She asked, a little unsure with it being her first time.
"Yes! Uh, I mean... it's good. It is." She couldn't see him from her position but could tell from the sound of his voice and the slight twitching of his legs she must have been making him feel great.
"Okay. I'm gonna try something, alright?"
"Y-yeah, whatever you want." Marco said a little breathlessly. Taking his permission Star leaned forward and ran her tongue along the length of Marco's cock. She heard him gasp and decided it must have been the right course of action. Moving her mouth up and down she licked along the length of him, letting her fingers follow after in a slow strokes. "Oh... It's... I feel like I'm going to soon." At first she didn't understand what he meant but it dawned on her that his shaking indicated she really was about to help him hit that Saint O she'd promised before.
"Did you want me to go faster?" Star asked from under the fabric, gripping her fingers around his member firmly. She might have been inexperienced but this made the most sense compared to any other action she could do to get him there.
"Uh huh! You can!" Marco responded eagerly and Star used the slickness she'd built up with her saliva to begin stroking him in a quick pumping motion. Marco began groaning a lot louder now and Star was getting excited seeing how much he reacted while in her grasp.
"C'mon Pinky, don't let me down." Star said gleefully and Marco responded, hitting his climax in her hand. Star nearly jumped back in surprise but found she couldn't escape so easily while caught underneath his dress. Her face and chest were hit by a hot liquid that she'd coerced from his body. Pulling her head up out from under his gown Star noticed how much cooler the air was now and realized she'd gotten sweaty being so close to him. Marco's upper body was laying down now on her bed, panting hard and recovering from his orgasm. While he took a breather Star used her hands to feel the substance on her chest and face. Getting some on one finger she placed it in her mouth to taste.
"Hmm... not the best, but not the worst thing I've tasted." Marco didn't even seem to notice her actions, amusing Star that she managed to rock his world that hard. Getting to her feet Star grabbed some tissues from her vanity and cleaned herself off. Once she was sure the substance was gone she went back to the bed and laid down next to Marco on her stomach, grinning at him wide. "So what'd you think, Pinky?"
"That... that was amazing." Marco said through deep breaths. "I've never felt it that good before." Star smiled proudly to herself.
"Looks like you passed your initiation. Welcome to Princess Jail." The actual princess giggled, happy to have made him feel happy too. After Marco caught his breath he looked over at Star and placed his hand out to her facing upward. She stared at it for a moment before moving her own hand over his, lacing their fingers together. She used her one exposed eye to look at their hands together, and then at Marco staring at her. It made her feel hot inside, and a different kind of warmth deep in her chest. Her hand gripped his and he gripped it in return. There was a fear if this went on much longer she wasn't going to be able to let him go from this room, let him go ever again. Her head was becoming overwhelmed with emotions and she recognized when it was starting to overtake her. "Marco, I-"
"Wrong name, Badnikki." Marco said with a smile. "Now it's your turn."
"What? Wait, I was the one doing the initiation."
"Not anymore. It would be rude to let my queen go without returning the favor." When she called him her queen Star felt the hearts on her cheeks glow in response. She looked away from him, how could he say that so easily to her?
"You big dummy, you can't just... call a princess your queen like that."
"Why not? Your the one that said I'd be calling you that by the end of this." Oh drat! She did say that. But she'd meant that in character, not as in her being... someone's actual queen.
"Well yeah but..."
"Up with you." Marco said and pulled Star up from her laying position. She could have fought him off but there was something comforting about being lifted into his arms. Her body was making her go along with things that her head was telling her she should probably keep from going too far. Either that or she was making up excuses as to why she was letting herself get away with this. "Now lean back." After some work Marco positioned himself with his back against the headboard of her bed, Star leaning against his chest. With her bare back against the soft material and his arms around her it felt really nice.
"I'm comfy." Star declared, settling against him.
"I'll make you feel even better." Marco said with more confidence than she was prepared for. Maybe he was falling into his role as well. His hands slide around over her, stroking her neck and collar bone. Sliding along her skin and slipping down over her chest. Star reached behind herself and adjusted her long blonde hair so it wouldn't get caught where they sat, arching her back. If she was going to give into this then she might as well be comfortable for it.
"Just remember who's in charge... Pinky." It was harder using the character names but she had to. It was the only thing that made them going this far okay.
"Whatever you say, my queen." She felt her heart beat increase when he called her that again.
"I'm not sure that was the best ahh!" Star tried to argue against him continuing to call her that but got distracted when his hands found their way to her breasts. His thumbs and fingers gently rubbed and lightly pulled at the nipples surrounded by the heart shaped areola on her Mewman skin. "N-not too hard!" Star said and found Marco's leg through his dress, squeezing his thigh with her fingers.
"Does it hurt?" Marco asked concerned but Star shook her head. It didn't hurt at all but it was making her very excited. "Okay, I'm glad. Let me know if it does." His head leaned in now to kiss her neck and Star let out a moan in response, unable to speak clearly at the moment as her body was assaulted. As he played at her skin Marco's right hand began to dip further down past her breast, slipping over her thigh. She knew where it was headed and that maybe letting him get that far was a bad idea... but she really wanted to feel his touch.
Spreading her legs apart, Marco's hand moved between her legs and pressed against Star's pussy through her tights. He moved slowly, his hand rubbing in small circles against her as she grit her teeth and closed her one exposed eye tightly. Her other hand that wasn't gripping Marco's leg moved up and gripped onto his hair. He winced a little in complaint but it didn't stop Marco from using his fingers to rub at her sensitive areas. After what felt like an eternity of teasing Marco's hand rose up and touched the waistband of her tights. "Is it okay?" Marco asked her quietly against her ear.
"Yes." Star said without even thinking about it, wanting that touch so badly. Slipping his hand under the thin fabric Marco maneuvered past her panties and pressed his fingers against her now moist pussy. She gasped when she felt his fingers touch her private spot, never having had contact like this before outside of her own hand. "Oh! Oh wow."
"I'm going to, okay?" Star nodded quickly and felt Marco rub against her vagina. Her hips lifted slightly off the bed to his hand, eager to get his attention. Using her left hand she let go of Marco's hair and lifted his left hand to her mouth. Star began to lick and suck at his fingers, just wanting something to let her mouth focus on while she was enjoying the moment. Thankfully Marco didn't fight her for it, letting her have his hand to suck at two of his fingers while his other hand probed her wet folds. Her legs twitched every time he touched at her entrance, making a small whimper around his fingers. After some exploring Marco's finger slipped upwards and rubbed against her clit, making Star moan loud around the fingers in her mouth. "There?"
"Yes! There!" Star ordered, licking his hand and trying hard not to bite into him. Marco did as she instructed and began to rub her clit as his main focus now, his hand moving back and forth rapidly over her sensitive area. Star's legs tightened up and she groaned hard, gripping onto his wet left hand with hers now as she was being pushed harder. "M-Marco!" Star said loudly as she felt herself climax against his hand, her toes curling in her tights and her thighs closing tight around his hand. Even with her body clenching together from the climax Marco's hand continued to rub against her, letting her ride out her orgasm over his dedicated touch. After a while she grabbed his forearm and breathlessly managed to stop him. "Tha-that's good. That's good... you can stop."
"O-okay." Marco said, pulling his hand hesitantly out from inside of Star's tights which were now stained with the efforts of their satisfying one another. Star was leaning against him now, panting hard as she caught her breath. It had felt every bit as good as she'd hoped it would. Possibly more. She took hold now of Marco's left arm, gripping it against her own chest and feeling Marco apply pressure to pull her into a hug.
"Wow... good work Pinky."
"Yeah, that was... really great." Marco said a little distracted, looking at his right hand that was covered in Star's fluids. Flipping up her eye patch and noticing what he was looking at she smirked to herself.
"Wondering what I taste like?" Star asked and Marco blushed bright red.
"I... I wouldn't... I mean..."
"Here." Taking his right hand herself she directed it to his mouth and pressed his fingers to his lips. Marco took a moment to taste what was there before pulling his hand away from his mouth again. "Well?"
"It was... not what I expected. But it wasn't bad." Star giggled.
"So you're saying you'd want to taste it again?"
"Are you asking or Princess Badnikki?"
"Depends on who's offering." Star responded, sitting up to turn and look Marco in the eyes. "We should probably get cleaned up though, huh?"
"Yeah, I guess so." Marco and Star sat there for a moment, as if they were trying to decide what they should say to each other before trying to go about the rest of their day like this didn't happen. As if this really was something that was done by two other characters that weren't themselves.
"I'm sorry I made you wear that dress so long." Star said, not really sure how else to address what she'd made him do. Though Marco wasn't too upset about it.
"Honestly I'm starting to get used to it. It has its advantages, as one princess showed me." Marco slowly got up off the bed, wiping his mouth clean of anything that had been left behind from the kissing and exchanging of other things. "I better get to my room and change though."
"Don't you want me to just magic your clothes back to normal?" Star asked, now laying on the bed and covering her chest with her bed sheets. Even if he'd seen her naked before she still felt shy when exposed for too long.
"I uh... think I'll just keep it. You know, as a reminder of our adventure."
"Really?" Star asked, legitimately surprised. "Do you want me to keep mine too?"
"Yeah! I mean... if you want to, sure. You do look really good in it."
"Okay!" Star responded gleefully, happy as she'd grown fond of this outfit too. "I'll meet you down stairs in a little bit."
"Sure thing. I'll see you soon, my queen." Marco said teasingly and waved to her, checking outside in the hallway to be sure his parents didn't come home suddenly. They were open minded people but Marco didn't want to have to explain this outfit to them if he didn't have to. Once he'd exited Star let out a sigh and pulled her pillow to her chest, hugging it as tight as she could with all her strength.
"You can't just say that to a princess, Marco!" Star complained to no one in particular, her face pressed against the mattress as she spoke. Her body was satisfied and she felt good all over, but that warm tingling in her chest hadn't gone away. In fact his words before leaving seemed to make it grow even further. She ignored it for now though. She had to. It was the only way for them to keep having fun as best friends. But that didn't stop her from responding to no one in particular again. "I'll see you soon... my king."