Headmaster Lucas

Headmaster Lucas smiled to himself as he passed the line of young women waiting outside his office. All up bright and early before seven on a Saturday morning, dressed nicely, hair brushed, prepared to have a discussion with their Headmaster about their scholarly progress.

It was not a sight, he fancied, that one would see at many other schools like this one. In fact, not at all what he would have seen on a Saturday morning prior to the changes he'd made at Warrington's Institution for Delinquent Girls. His half of the school—the one containing the girls who were a bit too old to really be called girls any longer, eighteen and older—had been out of control when he'd arrived, full of screeching, giggling harpies who thought they ran the place, terrorizing staff and teachers alike with their poor behavior.

His solution had been expensive, but nobody could argue that it wasn't effective.

The girls all watched him silently as he reached the front of the line, stepped inside his office, and closed the door behind him. Office hours had not quite begun yet. In preparation, he pulled a hand-towel and some sanitizing wipes from the cabinet against the wall and set them on his desk; then he opened the box hanging on the wall behind his desk, displaying rows and rows of gleaming keys, each hanging on a hook labeled with a first initial and last name in his secretary's clear print.

The clock ticked over to seven o'clock. He went and opened the door, and gestured the first girl inside.

"Maya Bradshaw," he said, closing the door behind her as she entered. The girl—only just eighteen, dark-haired and dark-eyed, with a round face framed by her curls—flushed, looking shy that he would remember her name; she was brand new to the school, after all, and they had only met briefly before, during her school tour with her father. He remembered her being much bolder then, glaring and cursing. "I'm glad to see your mood has improved since we last met." She flushed deeper.

"Um. Yes, Sir. I'm sorry for—for my rudeness when we first met."

"Oh, don't worry, I've been called worse," he said, tossing her a casual smile as he stepped behind the desk. Her eyes followed him, then caught on the hanging keys on display. "Theft, wasn't it?"

She didn't answer him right away, blinking in distraction. "I—sorry, Sir, what was that?"

"It was theft that led your father to bring you here, wasn't it? Stealing your stepmother's jewelry and so on?"

"Um, yes, Sir."

"Haven't stolen anything from us, have you?" he asked, then gave her a quick wink to show that he was joking. She flashed him an uncertain smile. "Now, what brings you to my office this morning?"

"Erm. The Matron said that you could...that you might..." she hesitated and chewed her lip, glancing at the hanging keys behind him again and twisting her hands in front of her.

"That I might unlock your purity belt for a time," he supplied for her, when it became clear that she couldn't get the words out. She nodded quickly. He smiled and turned to find her key, then held it out to her. "Here you are. Take it off and set it on that table over there."

Maya hesitated. "T-take it off...here, sir?"

"Oh, yes. Go on."

She hesitated for only another second, then turned away just a bit to preserve her modesty before pulling up her skirt. It was an awkward procedure, especially as she hadn't done it before; she fumbled and wobbled a little as she tried to find the correct angle, and then finally the key clicked in the lock and she let out a quiet little sigh of relief as she pulled the hard metal chastity belt off of her hips. She turned to face him again, chewing her lip, holding the belt and the key uncertainly. "I put it down over here, Sir?"

"Yes, and then come sit down."

"Sit down? I—I thought..."

He smiled. This was his favorite part with new students, teaching them the ropes. "I'm sorry if Matron Fitch didn't explain entirely. Your time with the belt off will be here, in my office. I'm afraid I'm only able to give you fifteen minutes. You did see how many other girls are waiting."

Maya stared at him, her eyes large, for several long seconds.

"Your time is ticking, girl. If you want a chance to satisfy yourself, I suggest you do as I say."

Maya's eyes got, if anything, wider. Then she placed the belt slowly onto the table.

"There you go. Now bring the key over here and take a seat."

She followed his instructions, dropping the key back into his outstretched hand. As he turned to put it away, he heard a quiet gasp as she sat in the seat across from his desk, and smiled to himself. He'd selected that chair very carefully; it looked innocent enough, with two depressions sanded into the wood to cradle one's thighs, as was often done to make a hard wooden chair more comfortable. But the rounded ridge between those depressions was exceptionally steep, and he imagined—from the reactions of many of his students—that it was quite overwhelming to have that ridge pressing up against their bare cunts after a week or more of being locked in chastity.

When he turned back around, he caught Maya shifting in her seat as if trying to get comfortable, her gaze a bit distant. He cleared his throat and she immediately sat up very straight, looking mortified. He sat in his own comfortable, plush chair, pulling it up close behind his desk.

"Now, how have your first couple of weeks been going, Maya?"

The girl blinked at him, clearly struggling to concentrate. "It's...been fine, Sir."

"Fine? Is that so? You certainly didn't seem pleased to be here when I last saw you."

"There were some, um, changes I had to adjust to," she admitted. As she spoke, she forgot herself and began squirming a bit in her seat again, rubbing her thighs together; he thought she might not even be aware that she was doing it, her body simply demanding that she chase whatever stimulation was available to her. "But it hasn't been bad."

"What have the biggest changes been for you?"

Maya blinked at him, then glanced over at the belt sitting on the table before looking at him again. "Um...the strict schedule, Sir."

He smiled and nodded. "I see. And the belt? Was that an adjustment, too?"

The color rose in her cheeks again. "Yes, Sir."

"A very difficult one?" She chewed her lip and shrugged. "How often did you masturbate before you came here, Maya?"

Her eyes went huge. "S-Sir..."

"Perhaps I wasn't clear enough before, in my effort to spare your sensibilities, so let me clarify for you. If you are going to have an orgasm this week, it will be here, in this office, in front of me, within the next—" he glanced at the clock, "—ten minutes. So I suggest you not waste your time on shyness."

Maya's mouth dropped open and she stared at him. Her grip tightened a bit on the arms of the chair and her thighs shifted helplessly at the word 'orgasm'.

"How often?" he prompted her, in case she had forgotten the question.

"E-every night, sir. Sometimes...sometimes more."

"Mm." He nodded. "And what did you use? Toys?"

"Sir..." she protested, then relented. "Just—just my fingers."

"Very good. That's good news, Maya. I've found that girls who are used to toys sometimes struggle more in this environment." He leaned forward. "Now, I've had good reports from Matron Fitch and from your teachers, and good girls do get rewards." She squirmed again. "Stand up, now, and I'll help you."

She blinked at him slowly. "Help me...?"

"With my hand, of course. Come on, you only have seven minutes left."

Maya stared at him for several seconds, and then slowly stood. He stood, as well. "Bend over now, arms on the desk."

She didn't hesitate this time, and she even spread her legs a bit, her back arching with obvious anticipation. As he walked around to stand behind her, he could hear her breathing picking up, though she tried to muffle it in one of her arms. He rolled her skirt up and out of the way, bracketing one of her soft hips with his hand, and the arch in her back deepened.

"Has anyone else ever touched you here before, Maya?"

"N-no, sir," she said shakily. As he tucked her skirt up, he exposed her sex: pink and damp, with just enough soft hair to indicate that she was on the cusp of womanhood. He hummed in consideration, and watched as her cunt clenched on the air.

Five minutes, now. It was difficult to balance with new students; he didn't want to frighten her by diving right in, as it were, but even after two weeks in chastity, five minutes might be a too tight of a time if he didn't get to it.

Of course, with some girls, that was the point, but Maya had truly been quite well-behaved for her first week, and he didn't see any need to be cruel to her.

He reached down and brushed his hand up the inside of her thigh, acclimating her to his touch, and she shivered. Then he brushed his knuckles lightly through the damp wrinkles of her cunny.

Maya muffled a quiet squeak into her arm again, her hips jolting a bit. He smiled and moved his knuckles forward, forward, until he was brushing over her clit. Maya's hips jolted again and she choked back a quiet mewling noise.

"That's alright. No need to be embarrassed. We're simply tending to the needs of your body," he assured her, rubbing his knuckles in slow circles over the erect little nub. "Does this feel good, Maya?" The girl whimpered and nodded her head against the desk. "How close are you?"

"C-close, Sir."

"Give me a number out of ten, assuming that ten is that you're on the edge of finishing."

"Um. Maybe—maybe a seven. Sir." She was making an admirable attempt to speak normally, which made him think she was over-estimating a bit. He pressed more firmly with his knuckles and began to rub back and forth instead, pillowing her clit between the groove of his fingers, and Maya let out a little "oh—" as her knees buckled slightly.

"Getting closer?" he asked.

"Oh—oh, Sir—" she whimpered incoherently, her thighs trembling.

"Only three minutes left now. How close?"

"An eight, sir—please, please—"

"Have you ever put your fingers inside yourself, Maya?" he asked. After several seconds, she shook her head. He shifted the angle of his hand until he could place his thumb at her entrance, rubbing it back and forth across the hole.

The pitch of the helpless little noises spilling out of the girl changed until it sounded like she was asking a question with each one. "Oh? Oh? Oh?"

"It's alright, girl. Here we go," he said, and eased his thumb inside of her slowly. Maya gasped and shuddered, her virgin cunt clenching down on him as if trying to urge him in deeper even as she let out an overwhelmed whimper. Once his thumb was pressed as deeply into her as he could get it, he began rocking his hand, rubbing his knuckles back and forth across her clit again as he shifted his thumb back and forth inside of her.

"Oh, Sir, oh, oh," Maya whined thinly, trying to keep quiet, doubtless very conscious of the other girls lined up outside. "I'm close. I'm close. Uhng. Oh—" her body clenched around him in little fits and starts, like she was teetering on the edge but wasn't quite letting herself fall over.

"That's good, Maya. Go on and come for me now. You've been a very good girl, you deserve it."

"Sir," she gasped, and then whined as her hips snapped and she came, her whole body shaking and curling into the desk, clenching over and over on his thumb. He kept massaging her hole and her clit, bringing her through the orgasm, until she was whimpering and limp, and then he slowly eased his hand back.

"There you are. All finished." He grabbed a handkerchief and dried his hand on it as he glanced at the clock. "And in good time, too. Only thirty seconds left." Maya flushed bright red and tugged her skirt back into place, and he smiled at her. "Well? Did you enjoy yourself or didn't you, Maya?"

"Y-yes, sir," she stuttered, her stare a little dazed.

"Then what do you suppose you should say?"

"Thank you?" she guessed, and he smiled and nodded.

"Very good. Go on and put the belt back on. Hurry up now, other students are waiting to see me."

The next three girls who came in were much the same, though they were all somewhat more familiar with the routine; but they were all doing well enough to have earned their release. Only one of them allowed him to assist her, however. One insisted on rubbing herself to completion in front of him instead, and one—an especially fiery young woman named Bernice—simply started rolling her hips to grind into the chair as soon as she sat down, giving only the barest pretense of listening as he spoke to her until she interrupted him mid-sentence by crying out her climax loudly enough that the sound must have carried out to the other girls waiting.

The next girl who came in, though, was much less happy to be there. Headmaster Lucas tutted at the impassive, haughty stare she directed at him as she walked into the room.

"Delia Winter." He flipped open her folder to review the comments submitted to him by her teachers and her dorm mother. "Caught smoking behind the field house again, it says here? And this is a rather impressive list of abusive language you've used towards your dorm mother this week."

"Impressive, huh?" she said, smirking. Delia knew the routine, too, although hers was different from the other girls; she was already bending over the desk, pulling up her skirt to expose her pale bottom to be caned.

"It says here that you stuck chewing gum in another girl's hair while she was sleeping?"

"Just having a bit of fun," Delia said carelessly.

The Headmaster shook his head at her and tutted. "I wonder about you, Delia. It really seems that nothing we're doing here is making an impression. I've known girls before who are resistant to caning, but do you really have no care at all for your own pleasure?"

She shrugged. "Guess not. Snap snap, Headmaster, wouldn't want to keep the other girls waiting. Some of them out there are dancing around like they've got ants in their pants."

"Hmm." He considered the impertinent girl for a moment, and then shook his head. "We'll try a different method of discipline today. No, no, stay right there," he said as she began to straighten up.

She gave him a bored look as he stood and turned towards his wall. Likely, she simply expected him to paddle or belt her rather than cane her. When he turned back to face her and she saw that he was holding the key to her purity belt, a crease of confusion appeared between her pretty eyebrows.

"I've learned that some women find their need for orgasm dwindles over time if they're receiving no stimulation at all during a period of abstinence," Headmaster Lucas informed her as he walked around his desk. "I wonder if that's where we've gone wrong with you. Two years, hasn't it been, since I spoke to your parents about having you wear the belt between semesters as well?"

"Sounds like a lot of big words to excuse the fact that you're a dirty old man and you want a look at my pussy," Delia fired back, but there was a thread of concern now in her brashness.

The headmaster smiled and placed a hand on the small of her back to keep her still as he unlocked her belt and slid it out from between her legs. As he suspected, her little slit was relatively dry, not damp and swollen the way that many of the other girls would be after so long a period of denial.

Even so, she should still be sensitive to his touch. He ran his thumb back and forth over the lips of her sex, and the girl immediately sucked in a surprised breath. The Headmaster chuckled.

"There. Let's see if this helps things, shall we? Spread your legs a bit more, please." Of course, she wasn't especially inclined to obey him, so he had to gently nudge one of her ankles with his foot until she was forced to listen, spreading her thighs until the lips of her sex opened a bit and exposed the pink, delicate skin inside. It was only just beginning to glisten in response to his careful manipulations. "Ahh, there we are."

He pressed two fingers up against her there, gently capturing her labia between them and massaging in light circles, taking care not to be too rough with her given that she wasn't as wet as the girls he usually attended to. It wasn't long before she began to breath harder, her back arching deeper as the folds of her sex plumped up and her hole began to secrete the evidence of her arousal.

"That's it," he said soothingly. "See, now your body recalls how much it wants attention here. How does it feel, Delia?"

"Uhh," she grunted senselessly in response. The Headmaster smiled and trailed his fingers up to circle around her clit, and she sucked in a shaking breath, then groaned quietly. "Oh. Oh no..."

"What's wrong, Delia?" he asked. The girl just shook her head, hunching forward to press her forehead against the desk, but he could guess from the way her hips were beginning to tremble. "Do you want an orgasm? Are you finally regretting your misbehavior?"

"No," Delia denied, but the lie was clear in her shaking voice. He circled her clit with his fingers again and she gasped. "Oh, fuck."

"Language," he chided her. "Well, if you still don't care about climaxing, maybe the problem is that you've forgotten what it feels like. Perhaps I need to remind you." He felt her body shift and her cunny flutter against his fingers, and he smiled. "Tell me how close you are, Delia, out of ten."

"Don't want to."

"No? I'll guess for you, then." He pressed his fingers in a little bit tighter, feeling the heat of her core and the way her muscles twitched. "Perhaps a six?" He reached up and bracketed her clit with two fingers, rubbing it on both sides, and her hips stuttered, thrusting into the pressure. "Or a seven?"

"Shut up. Nobody cares about your stupid numbers," Delia muttered through grit teeth.

"If you want to remember what it feels like to experience an orgasm, Delia, then I suggest you start to care," he said, drumming his fingers lightly against the sensitive little bud as he glanced at the clock. "You have five minutes left with me. I don't want to misjudge your arousal and accidentally leave you unfinished because we run out of time."

Delia said nothing to that. The Headmaster switched to rubbing the pad of his finger up and down her clit, stroking all the way down through the folds of her labia—which were finally becoming dewy with desire—and back up again to swirl around the tip. She groaned.

"Eight," she admitted finally.

"Very good, Delia. Very helpful," he praised. He continued the up and down motion, slowly increasing the pressure, and the girl's thighs spread wider automatically as her back arched deeper. "Any higher now?"

"Nine," Delia said, her voice shaking as much as her knees. "N...nine. Ohh...nine and a half," as he focused on her clit, rolling it firmly between two of his fingers.

"Tell me when you reach a ten. We only have a couple of minutes left, Delia," he said calmly.

"I...I..." she whispered, then groaned as he switched to a rocking pressure. "Oh, that's almost—ten! Ten! Oh, I'm gonna—no, don't stop!" she gasped in shock as the Headmaster removed his fingers. "I didn't come yet, I didn't come yet!"

"I know," Headmaster Lucas said mildly, taking advantage of her spread thighs to lock the belt back into place around her rocking hips. Delia shrieked as she felt the metal close around her again, reaching down fast, but not fast enough to stop him.

"You said you would make me come! You said!"

"Did I? Just having a bit of fun," he said, throwing her own words back at her.

Delia gaped at him, her hips shuddering and her hand rubbing obscenely against the swell of the chastity belt as her body instinctively tried to find the last bit of stimulation it needed to send her over the edge. The Headmaster tutted and pulled her away from his desk.