Marco Diaz had always been considered the 'safe kid'. He always aired on the side of caution, he always came prepared, and he always went with the most logical route. He was also a very great student, holding mostly straight A's with the occasional B+ every now and then. With a such spotless behavioral record and academic background, it was little wonder he had been offered to be the first one to attend such a prestigious academy like St. Olga's, even if he hadn't really wanted to at the time.

You see, St. Olga's had been an all-girls academy for years. It had a history of being a go to for young ladies who were considered discipline problems. Girls walked in as trouble making delinquents, and walked out as reformed and properly behaved young ladies. It had produced many well off members of society, and girls who graduated found many opportunities opening up for them. So when they had finally decided that they were offering spots to boys, Marco's parents figured he was a shoe in. And they were right. The school had a very strict standard when it came to taking in male students. So strict Marco had been only one in three to make it.

And while most boys would be happy to end up in a school full of delinquent girls who had been denied years of experience with the opposite sex, Marco hadn't wanted anything to do with it. He had never had the best luck with girls, and he couldn't see himself thriving in a school full of them. When he had first arrived he found that he was the only boy in his grade, and thus had the eyes of pretty much every girl in his class. It was more than a little overwhelming. But, he kept focusing on his studies and kept himself out of trouble. And eventually, his efforts had been rewarded with the position of Head Student.

The entire school had been in an uproar about a boy getting the position. Not because he wasn't qualified. Nobody would even try arguing that. But because one of the many perks that came with the title of Head Student was being able to deal out punishments to your peers.

St. Olga's was a very old fashion and strict place, and corporal punishment was alive and well inside of it. Margo still remembered his first day when the teacher called some girl to the front of the class, made her lift her skirt, and deliver a dozen hard whacks of the ruler on her bottom. It was both shocking, and... sort of arousing. With his behavior he never had to worry about being on the receiving end of it, and he'd try to keep his head down with punishment were dolled out. He didn't want everyone thinking he was a leering pervert after all.

But around mid year the headmistress had called him to his office, told him just what an impeccable job and impression he'd made on her as well as the rest of the staff, and awarded him the new position as well as a shiny badge and cane to go with it.

Needless to say, Marco had been very shocked. He didn't think he was fit for a job like this. He didn't have it in him to go around and whack girls butts. It'd be too awkward. And it was... at first. But after the first few times he had quickly gotten the swing of things, and found that he enjoyed his new position very much. He never abused his authority, but he did carry it out with well hidden glee.

And how could he not when he had opportunities like these?

"Hello ladies, shouldn't you be in class?"

Janna and Star both whipped their heads towards the boy as he made his way onto the roof of the school. Students weren't supposed to be allowed on the roof, and while Marco was allowed to check for any rule breakers when he did his daily rounds through the halls, he rarely did so. He figured every now and then was good enough. Most times it was clear, but every now and then he caught a few students hanging out there, just like today.

"Aw man, it's the fun police..." Janna muttered.

Star stood up and smiled nervously. "Hey Marco, we were just-"

"Skipping class and going into a restricted area?" he finished for her.

Star opened her mouth again, but Janna cut her off. "Save it Star. Diaz is going to whack us either way so might as well not dig the hole any deeper," she said rolling her eyes. Janna had been one of the girls Marco enjoyed punishing the most. Not just because she was pretty... which she was, but because she had enjoyed teasing and messing with him so much. When he'd first gotten here she had almost drove him insane with just how weird and devious she was. Taking his keys, snooping through his wallet, cracking his locker combination. Once he had gotten the Head Student position however Marco made sure to blister her butt for each and every one of her little pranks, forcing her to back off a bit. She had obviously been bitter about it, but there was little she could do.

Star sighed and hung her head. "Fine, but can you let us off easy? We already got the slipper last night and I'm still sore." Star was another girl who Marco was pretty familiar with. She was a fairly nice girl with a knack for landing herself in trouble. Not a bad person by any means, just a little too adventurous for her own good. Hanging out with Janna didn't help either. Marco tended to crack down on her a bit hard in the hopes she'd straighten up, but so far it didn't seem to stick.

"Sorry girls, but rules are rules. Three for skipping class, and three for being on the roof. Now skirts up and hands on the wall," Marco said pointing to the nearby wall with the cane.

Star groaned out while Janna clicked her tongue. "You know Marco, if you're that desperate to see us in out underwear, all you have to do is ask," she said.

"I am, right now. Now hurry it up before I give you extras."

The girls uniform's consisted of a white blouse, a plated blue mini skirt, and knee high socks. Some teachers would make them tuck their skirt into the back of their waistband, while others just made them remove them completely. Marco preferred the ladder, just to make sure their wiggling didn't shake their skirts loose mid punishment. The two girls both unbuttoned their skirts and put them off to the side, now standing in their blue regulation kickers.

Marco pointed again, and the two made their way over to the wall and bent over slightly, placing their hands on it and spreading their legs. They had been in this position more than enough times to knock how to do it properly, and just wanted to get their punishment over with. "Okay," Marco walking behind them and taking in the sight of the two lovely bottoms. Their knickers both hugged their rears tightly, showing every curve. "Six strokes each. If you break position or reach back before I tell you, it won't count. Got it?"

"Yeah, just get on with it," Janna complained.

Marco tapped her bottom with the cane. "Hey, don't be cheeky. Unless you want extras."

"Sorry..."

Marco nodded and then tapped her bottom a few more times, lining up his swing. Janna held her breath and braced herself. After a few moments, Marco brought the cane back, and then swung. It swished through the air and landed with a CRACK! Janna winced and grit her teeth at the sharp pain in her bottom. Marco could already see a red line starting to form on her cheeks.

He smirked to himself as he tapped her bottom again, this time aiming a bit higher. Janna had always been a bit of a tough cookie, so he never gave her any less than six. Sometimes she took them in silence, and other times he'd managed to get a bit of squirming out of her. With her getting slippered last night he was sure he could really take it to her this time.

CRACK!

Janna winced once again, letting out a small gasp. Yeah, she was definitely still sore from last night. He was going to take full advantage of this. He swung again, this time hitting right between the two lines he had made earlier. He'd made this a particularly crisp one, and even Star jumped when the cane cut into Janna's frump with a loud CRACK. This time Janna let out a yelp. "AH! Christ Diaz! Ease up on me!" she whined shaking her rear back and forth, as if it would shake out the string.

"Settle down Janna. You have only have three more," he said tapping the cane against her again. Janna grew wide eyed when she felt where he was aiming. The cane had touched right between the curve of her bottoms and the top of her thighs. It was what the teachers and students deemed the 'sit spot'. Not only did the strokes hurt worst there, but it made sitting down later extremely difficult. Not to mention that along with their mini skirts it let all the others girls know you were sporting a freshly caned bottom. He really wasn't cutting her any slack today.

CRACK!

"OUCH!"

Marco smiled, as he watched Janna hope from foot to foot. It was a very rare sight to see her so jumpy like this. He enjoyed the show for a bit before tapping her bottom, signaling for her to settle down. She reluctantly did so, only to gasp again when she felt him tap the exact same spot. He was doubling up stroke on her! Before she could even think about speaking out, the cane swished through the air and cut into her sit spot once more, landing right where the previous stroke had.

CRACK!

"YEOW!"

Janna took her hands on the wall for only half a second, nearly jumping out of position to grab her poor bottom. But somehow she had caught herself and snapped right back in place. She stomped her foot down angrily as she tried to take her mind off of the throbbing pain she was feeling. Marco looked genuinely impressed. He'd really thought he'd had her with that one. But maybe the last one would be the tipping point. Once again, he aimed for the exact same spot he had before. Piling on strokes was something he usually didn't do unless he really wanted to send a message, and even then three in one spot was rare. He really was trying to get her to break this time around.

CRACK!

"GAH!"

Janna's knees nearly buckled as the cane cut into her. She struggled to keep herself in position, but after a few moments managed to steady herself. She panted as she kept leaning up against the wall, knowing that moving before Marco gave the word was ground for extra strokes. Marco nodded. A bit disappointed she managed to hold out, but also pretty impressed. Janna really was a tough girl. Now it was time to see if Star could hold out as well. Judging from the way she was already shaking, he had his doubts.

He moved over a bit towards her and then tapped her bottom with the cane. "Ready Star?"

"No..." she answered bitterly. He chuckled and tapped her butt a few more times, then brought the cane back and swung. CRACK! Unlike Janna, Star didn't bother trying to act tough. She let out loud girlish "EEP!" before she began furiously shaking her bottom. "OW! OW! OW! Not so hard! I told you I'm already sore!"

"If Janna could take it, so can you," Marco said giving her a few warning taps. He waited for her to settle down before bringing the cane back again. Star sucked in a breath and squeezed her eyes shut as the cane cut through the air and sliced into her bottom once more.

CRACK!

"OUCH!"

The blonde danced from foot to foot, giving Marco quite the pleasant view of her pert rear wiggling back and forth. He didn't even wait for her to settle down before giving the next stroke, swinging and hitting his intended spot with pinpoint precision. CRACK! This one had clearly caught Star off guard, and her knees nearly buckled. She groaned through her gritted teeth as she struggled to stay in position and keep her hands on the wall.

"That was a dirty one Diaz," Janna commented from beside her friend.

Marco ignored her and tapped Star's bottom. "Okay, let's get that bottom up Star. You have three more coming."

Star groaned miserably, knowing that he'd likely pile them on her sit spot just like he did with Janna. But there was nothing she could do but grit her teeth and try to keep still. She straightened legs back out, once against offering her bottom up for another stroke. Sure enough, he tapped the cane against her sit spot.

CRACK!

"AAAHHH!"

Star threw her head back, her blonde hair being tossed up into the air. She kept her hands on the wall, but hopped up and down before shaking her bottom from side to side. Marco watched in amusement as she let out a string of 'oh's and 'ow's. This time he took his time and waited for her to get it out of her system. She wasn't as tough as Janna so it only seemed fair to give her a bit more time to ready herself.

When she finally did settle back down he tapped again, on the exact same spot, just as Star feared. She whined and once again tried to brace herself. But when the crisp stroke came slicing into her bottom with a CRACK, she found herself doing another dance of pain. "OW! OUCH! God that stings! Not there! Not again!" she whined.

"Just one more Star," Marco said tapping the cane against her.

She let out a whimper as she felt it touch the same spot for a third time. This was it. If she could take this she could get away with no extra strokes. It didn't have to be pretty, she just had to hold on.

CRACK!

"AH! Oh God! OW! OW! OW!"

That had been the hardest stroke yet, and Star had jumped up for a moment before immediately slapping her hands back onto the wall. She once again danced about, her bottom throbbing and her heart was racing fast. Technically she had broken position, even if only for a second. Was Marco going to hold it against her?

The boy had honestly considered it for a few moments, but decided to let her off the hook. Star wasn't really deserving of a severe punishment. She was a good person for the most part. So he didn't want or see the need to keep piling it on. He looked over the two backsides before him. Both had three red lines forming across their cheeks, along with a forth crimson line across each of their sit spots where he had piled it on. He nodded in approval. "Alright ladies, you can stand up now. But don't rub," he warned.

Star and Janna both stood up straight, discomfort clear on their faces and their body language. They both looked like they wanted to reach back and start rubbing their poor bottoms, but knew better than do try it before he gave them the green light. "Can we go now?" Janna asked wincing. She needed to get somewhere and start rubbing her stinging rear.

Marco smiled and held up the cane. "Not yet. I don't want you two trying to rub those marks away so quickly," he ordered. The two girls looked confused, while Marco had to hold back a laugh. Yes, being 'safe kid' had certainly paid off.

Star and Janna both groaned as they walked through the hall stiffly. Not only were their bottoms on fire, but they couldn't even rub them down now. Marco had made their hold their hands out and delivered three crisp strokes of the cane to the palms of their hands, making trying to rub their sore rears a doubly painful experience. He'd then sent them off with a promise of a baker's dozen the next time he saw them. They had quickly hurried off, not wanting to give him anymore excuses to bend them back over.

"I've gotta stop hanging out with you..." Star whined blowing on her stinging hands.

Janna somehow managed to find it in her to smirk. "Yeah right. You know I'm too much fun to be around," she said confidently. "Besides, it's not so bad."

Star pouted. "Maybe not for you, but my butt is killing me. I won't be able to sit down right for a week."

Janna shrugged. "I mean, yeah. But it's still kind of exciting right?" she asked raising her eyebrows.

Star blushed slightly. "What do you mean?"

"I mean Marco being all assertive. He was such nerd when he first got here. Now he's being all bossy. Ordering us to take our skirts off and spanking us and stuff. He's super commanding. It's kind of hot."

Star looked down, her blush growing deeper. It was true. She hated having to get the cane. It was painful, and the fact that there was a boy doing it made it even more embarrassing than it already was. But, there was also something... wild, about being bossed around and punished by a boy her own age. "Yeah, I guess..." she muttered. Her eyes then widened. "Wait, Janna. Do you like Marco?" she asked.

The girl smirked back at her in response. "Maybe. Maybe not. Do you?"

Star thought for a moment. "Huh... I don't know. I do think he's kind of cute."

"Maybe we can tell him that next time he's caning us. He might go a little easier."

"Or a little harder..."