Christmas Break 6

Professor Simon Cairn teaches at Sutherland's Private School for Girls and Young Women. One of his favorite students is Angelica, a bright young woman who has chosen to stay at the school over winter break as she prepares to apply to co-ed graduate schools for further education. When Professor Cairn learns that Angelica is struggling with a delicate personal problem, he reaches out to offer some personal assistance. Sensitive content warning, 4k words.

Content Warnings/Tags: power imbalance (professor/young adult student); discussion of a parent using sexual control as punishment; mild fetishization of virginity

As much as Professor Simon Cairn enjoyed teaching at Sutherland's Private School for Girls and Young Women, he couldn't deny that every year he looked forward to the winter break.

Part of it was the view: he had to admit that it was very precious and sentimental, the historic stone buildings of the campus all decked out in green pine boughs and wreaths, covered in snow. The pond on the grounds would freeze over in December, and with fewer students to trample the snow it would remain pristine and sparkling, creating a picturesque vision of winter that he could enjoy from the warmth and comfort of his office.

Fewer students. Never no students. That was another point in favor of the winter break: while most students ran home to their families, to open gifts and spend their parents' money on new wardrobes and everything else that young women of means did at Christmastime, a handful of students remained every year to spend their break in the dormitories.

The younger ones, of course, were typically there for more tragic reasons--girls on scholarship who would survive the winter better at the school than going home to a family with not enough income and too many mouths to feed, or orphaned heiresses who had, through accident, tragedy, or misadventure, been left to navigate the world with money and trust lawyers in lieu of parents.

But most of the older students who remained had chosen to do so. They were studious young women, driven, dedicated to learning, who saw some value in continuing to study through the break. Many were preparing to graduate from Sutherland's, budding young adults on the cusp of breaking into academia themselves, completing the extra courses required to qualify them for entry to a co-ed graduate school.

These were often Simon's favorite students, and he appreciated the chance to spend some time with them individually.

One such student who had caught his attention recently was Angelica. She was in her final year, recently turned nineteen, preparing to apply to a school where she hoped to get a doctorate and eventually become a professor in her own right. She was a very admirable young woman: ambitious, curious, with the follow-through to go far in life. Simon had built a rapport with her, since her self-study course on political history was within his own area of expertise.

Yes, he had developed quite an interest in Angelica. So when he'd heard some rumors from the dorm mother--whispers that Angelica was having some trouble focusing due to a personal problem--he decided to intervene.

He was sitting in his office, staring out the window at the beautiful white landscape, when she knocked on his open door. "Um. Professor Cairn? The dorm mother said you wanted to see me?"

"Angelica." He turned to face her and smiled. "Come in. Close the door behind you, there's a good girl. Take a seat."

Angelica sat, settling her ever-present messenger bag into her lap. She reached into it and began to shuffle through papers. "Is this about yesterday, the question I had about criminal justice systems in the 1600's? Because I found this book in the library, it's meant to be about historic folklore but it has a reproduction of a criminal code from a town dated to 1649--"

"No, no, this isn't about that," he assured her, "though I'd love to take a look at that book some time, that does sound fascinating. No, I wanted to discuss something a little more personal with you."

Angelica paused, her hands still dipped into her bag as she looked at him with wide, uncertain eyes. "Personal?"

"Yes. If that's alright."

"I--well, yes, I suppose that's alright." She frowned. "You aren't going to give me a Christmas gift or something, are you? I just wish you'd warned me, I didn't get you anything."

"No," he said, then reconsidered. "Well, maybe you might consider it a Christmas gift, in a way, but you're certainly under no obligation to reciprocate. Listen, Angelica, the dorm mother mentioned to me that you've been having some trouble...sleeping."

In spite of his delicate choice of language, Angelica's face immediately colored bright red and her hands sprang out of the bag as if it had bitten her. "I--she told you?" she squeaked.

"It's alright, it's nothing to be embarrassed about," Simon assured her, keeping his voice low and soothing. "I spoke with the headmistress as well, but I know second-hand information isn't always accurate, so let me tell you what I know, and you can tell me if it's correct. As I understand it, your father has been requiring you to wear a chastity belt, as a condition of your continuing your studies?"

For a long moment, it seemed as if Angelica was frozen with mortification. Finally, just as Simon was beginning to worry that he'd have to repeat himself, she gave a single, wide-eyed nod.

"Alright. And you've been finding this...a frustration." He thought Angelica wouldn't thank him for repeating exactly what the dorm mother had told him, which was that she had walked in on Angelica crying as she tried fruitlessly to masturbate by pressing on the belt.

The blush in Angelica's face spread down her throat, and she squeezed her bag, lifting it a bit as if she was thinking of hiding behind it. "I--I--I'm fine," she stammered weakly. "Really, I just--it was nothing."

"It's not nothing if it impedes your studies," Simon disagreed. "I can see this is embarrassing for you to talk about, Angelica, but really, it's perfectly normal for a young woman your age to struggle in such a situation. And here you've forgone your winter break at home, which I'm sure would have been a welcome break from wearing the belt--" he paused as Angelica gave a brief shake of her head. "No?"

"I--Father has me wear it at home, too," she admitted, her voice wavering.

"At home? All of the time?" Simon asked, surprised. She nodded. "Then when do you get a chance to--I apologize, this will be an indelicate question--to, ah, reach release?"

"Father doesn't find that...necessary. For women."

"Hm." Simon considered commenting on how Angelica's mother might feel about that attitude, but then realized that that probably wasn't the issue at hand. "Does he disapprove of you pursuing further schooling?" She nodded. "This is his way of punishing you for it, I suppose?"

"I think he hopes I will change my mind," she admitted, then took a breath, her expression setting with determination. "But I don't intend to. And--really, it's fine. So, thank you for your concern, but I have more important things to worry about, and there's nothing to be done for it, so--"

"Nothing to be done?" Simon asked. "Do you know that he gave a copy of the key to the school?"

"Well, he had to, for--for medical concerns," Angelica said, blushing. "I think the headmistress has it."

Simon silently reached into his breast pocket and pulled out the key. He saw in the widening of Angelica's eyes when she recognized it.

"Professor," she breathed. "I--what are you--how did you..."

"I asked her for it. To perform an examination of you, for your health, as the nurse is out for the holidays and the dorm mother has some concerns."

Angelica's face, which had been reducing to a slightly more healthy color, abruptly turned brick-red. "E-examination?"

"Yes. I think a pelvic exam would be prudent, to ensure that everything still...operates as expected in that area." He gave her a significant look. "I will conduct the exam myself. Your father provides a significant source of funding to the school, so I doubt the headmistress would be amenable to the idea of simply giving you free access to the key in flagrant disregard of his wishes; but he can't possibly complain about a medical examination conducted by the school staff."

Angelica stared at him, squirming and clutching her bag still. "But..." she said finally, then hesitated. "By, by examination, Professor, do you mean...?"

Perhaps he was being too delicate. "I will unlock the belt and use my fingers to bring you to orgasm."

The sound Angelica made in response to that was more of a strangled squeak than a word, and she lifted her bag up until it covered her chest and the lower half of her mouth.

This, however, meant her lap was uncovered, and it became much more visibly obvious that she was squirming a little in her seat, squeezing her thighs together.

Angelica followed Simon's gaze down--noticing that he was noticing her--and squeaked again, pulling her bag up further to cover her face entirely.

"Or," he offered, out of consideration for her obvious shyness, "you could perform the...exam...yourself. But I will need to remain in the room. You can also say no, if--"

"You-can-do-it," Angelica blurted, interrupting him. The words were quick and high-pitched, like she was forcing them out.

Simon paused. "You do want me to touch you?" he asked, to be sure.

Angelica nodded. She was still hiding her face behind her bag, so all he saw was her hair bouncing behind it.

"Alright." He waited for her to put the bag down; she did not. "Would this be easier for you if you didn't have to see me?"

"...Maybe," she admitted in a small voice.

"Alright," Simon repeated, and set the key down before opening a drawer in his desk.

"It's not you, Professor!" Angelica hurried to explain, dropping her bag just enough to peek at him over the top. "It's not--you're very--" she stopped, flushing again, then tried a different statement. "It's only, seeing you, knowing you're looking at--at me--"

"It's quite alright, Angelica, I'm not offended at all," he assured her. "I can see that you're embarrassed, and that's only natural, under the circumstances. Here." He pulled out an opaque silk scarf and held it up for her to see. "If I were to tie this around your eyes, would you feel better?"

Angelica stared at the piece of cloth, her eyes growing big and round. After a long moment, she nodded.

Simon stood. "Close your eyes, then, and put down the bag."

Another moment of hesitation, and then she did as she was told.

She placed her bag--with obvious reluctance--on the floor beside her chair, and then screwed her eyes shut, wrapping her arms across her middle.

Simon walked around the desk, making sure to allow his shoes to scuff the floor as he did; it wouldn't do to startle her.

He circled behind Angelica and informed her, "I'm going to tie it on now." She nodded, so he lifted the piece of silk and folded it over itself before tying it carefully around her face, testing the tightness to be sure it wouldn't be uncomfortable for her. "How does that feel?"

"Good, Professor," Angelica murmured. She already sounded a little less strangled, some of the nervous tension leaving her body.

"That's good. I'm going to put my hands on you now," he informed her. Once she nodded again in acknowledgement, he rested his hands on her shoulders, before sliding down to cup her elbows. "Stand up. I'll guide you."

Angelica stood carefully, and--directed by Simon's gentle grip--walked to the small settee positioned against the wall of the office. She sat down at his instruction, and waited patiently while he went to lock the door; the school was mostly empty during the break, but there was no reason to take chances.

"Alright," he said, retrieving the key from his desk before returning to stand in front of Angelica. She looked quite fetching with the ivory silk tied around her face, highlighting the bright blush of her face that spread down her throat, disappearing under the neckline of her dress. "I'm going to unlock the belt now."

Angelica nodded, her hands tangling in the skirt of her dress. Then she took a deep breath and tugged at the ruffled fabric, rolling it up to expose her knees and her thighs and then, hidden between her legs, the glint of metal.

"Very helpful, thank you," Simon said, kneeling down on the carpet in front of her. He had to push her skirt up a bit further, revealing her hips, before he found the padlock that kept the belt in place. He pressed the key in, and then, with a click, unlocked the belt and pulled it open, so that the metal shell opened up in two pieces.

She was wearing no underwear underneath, of course. Her exposed sex, framed in the waves of her skirt like a precious flower buried in lush foliage, was dewy with eagerness.

"How long since your father began requiring you to wear this?" Simon asked as he eased the belt out from under Angelica, setting it aside on the chair she'd been seated in before.

"A--a year and a half," she breathed. "Since I told him I wanted to attend a co-ed graduate school. Um..."

"Yes?" Simon asked as she trailed off. He placed a hand on her knee so that she would know where he was, and heard her inhale quickly through her nose.

"I--just--do I look...normal? Down there? Not, not ugly or anything?" Angelica stammered.

Simon was glad for the blindfold, because if Angelica had seen the smile that her vulnerable, virginal question brought to his face, it likely would have only embarrassed her more. "You have nothing to worry about," he assured her. "You are as well-formed here as you are everywhere else."

"Oh," she said, sounding both abashed and reassured. "Thank you, Professor."

He moved the hand on her knee upwards then, brushing his fingers along her thigh.

When he passed over the barrier of her stockings to her bare skin, she sucked in a breathy gasp and her hips jolted, her sex visibly pulsing. The exhale of the breath came out as a surprised-sounding, stuttering little moan.

Angelica lifted a hand to cover her mouth, then dropped it to speak. "S-sorry!"

"Shh, there's no need to apologize," he assured her. "It's natural for you to be so sensitive, given how long you've been waiting. I'm going to start by taking a closer look at the state of your hymen, alright?"

"My--I'm a virgin, Professor, I promise!" Angelica squeaked, sounding appalled.

"I know," he assured her. "That's not what I'm looking for. Every young woman's hymen grows in a bit differently, and it can be stretched or torn in the process of normal, non-sexual activities in adolescence such as swimming and horse-riding. I just want an idea of what we're working with, as I intend to penetrate you with my fingers, and I don't want to hurt you."

"Oh. Um, okay," Angelica agreed, settling down a bit. She seemed soothed by the instructional cadence of his voice, the same rhythm he had developed for delivering lectures, to overcome his natural tendency to rush through an explanation when he was excited about a topic.

Simon decided to continue speaking as he touched her. "I'll begin with spreading your outer labia," he stated, keeping his voice low and matter-of-fact.

She sucked in a breath as he acted on the words, her sex twitching and pulsing again in response to the gentle pressure of his fingers on the fleshy lips.

With the labia majora pulled out of the way, he could see the movement even more clearly, the evocative flickering of her delicate pink flesh broadcasting her mounting need. Her clit was on the smaller side, a little pin-head just barely visible in the wrinkles of flesh crowning her sex, but the focused twitching there made it more obvious, drawing attention to it. Her body's desperation for touch was palpable.

"Very pretty," he stated, to further address her anxieties about her appearance, and she made a faint noise of embarrassed gratification. "Now I'm going to take a closer look at your vaginal opening. Let me know if you feel any discomfort."

He used his fingers to spread her skin further, gently pressing and rubbing around her untouched hole, both to better identify the structure of the skin there as well as to provide some stimulation.

Angelica breathed in hard and her entrance clenched and then relaxed, a small amount of clear fluid leaking out.

"There," Simon said, eyeing the opening, the obstruction of the hymen along the lower rim. "It is present, but it shouldn't cause us too much trouble. I think you should be able to take two fingers without any pain as long as we move slowly."

"Oh," Angelica gasped quietly. "I...yes, Professor. Please."

"Alright. Then I'll proceed," he said, placing his free hand on her thigh to squeeze gently. "One finger first."

He shifted his grip, no longer spreading her apart, instead running a fingertip along her damp folds. As he slipped it into her at a slow, steady pace, her breathing quickened and her knees jolted, one of her shoes dragging along the carpet.

"That's it," Simon assured her. He pulled his finger out a bit when he reached the second knuckle, then twisted it as he pushed it in again, stretching and loosening her entrance in gentle movements. "You've never done this yourself? Penetrated with fingers, I mean?"

"N-no," she admitted, her voice faint and wobbling. "I only...I only rubbed over my underwear, before."

"And that was enough to bring you to climax?" he asked. She nodded. "So you've always been quite sensitive, hmm?"

"I...yes..." she murmured, then gasped when he twisted his finger again, pushing it in further. Her knees quaked and her flesh squeezed around him. "Professor..."

"Good?" he asked, and she nodded vigorously. "I can feel the tension. You're quite pent-up, aren't you? No, no, there's no need to be embarrassed," he assured her when her face screwed up in some distress. "Anyone would be, after a year and a half. It's perfectly natural. We're going to take care of that now, aren't we?"

"Yes, Professor, please," she begged, a note of desperation in her voice, as if she worried he would go this far to tease her and then deny her the climax that she needed.

"Shh, it's alright, Angelica. I promise, you'll feel better very soon. I'm going to start working on the second finger now."

He eased his first finger out and added a second. He didn't push in right away, as it would be a tight fit; he began with just rubbing and working at her entrance with both fingers, pressing at the sensitive skin there until Angelica was breathing quickly again and visibly struggling to stay still, her thighs trembling and her hips rocking in restrained little movements.

When her entrance was thoroughly soft and slick and as open as it was going to be, he pressed in with both fingers, moving very slowly. He wanted to stretch her hymen, not cause her pain by tearing it.

"Oh," Angelica gasped as his fingers slowly penetrated her. "Oh, Professor, oh, it's, oh--"

"I know. You're doing very well," he assured her. He moved slowly, pausing whenever he felt resistance, backing off and twisting as he pushed in again to slowly work her open.

By the time he was up to his second knuckle again, slowly wiggling the thickest part of his fingers into her, Angelica's breathing was coming in whimpering little pants and he could feel her body pulsing and squeezing around him in a quick, needy rhythm. When the knuckles finally slipped in, allowing him to fully seat his fingers inside her, she let out a little cry.

"Shh. Very good, Angelica. You're doing so well," he murmured, squeezing and rubbing her thigh. "Do you feel close to orgasm?"

"I--I don't know," she admitted. "I want it, Professor, please."

"You'll get it," he promised her. He shifted his fingers inside her gently, pulling out just enough that his knuckles began to stretch her again before pushing them back in, which made her gulp and shudder. Then he curled his fingers carefully, searching for the spot inside her that would best respond to his stimulation.