The Schooling of Carolyn

'Still feisty? Perhaps you need another cleansing.'

She gasped, shaking her head frantically, and began to stammer an apology. Not that! He held up a hand, and she ceased. Your place is to obey, she told herself. Do not push him.

'Come here.'

She leapt up and toward him all in a single movement, fear lending her a bit of strength. At his direction, she stood, legs apart, and laboriously raised her bound hands above her head, then pushed them back behind her neck. Losing her balance on the heels, she fell back against the desk, sitting down hard. She whimpered.

'That will do.” He pushed her legs farther apart, forcing more weight down on her ass. The bruised flesh complained, but she was far more disturbed by the shifting of the plug within her. It pushed forward, against the flesh which formed a shared wall with her vagina. Disgusted as she was by the intrusion, still, it felt … good. Better than good.

Her legs were far enough apart now that her newly denuded crotch rubbed against the desk. Cool polished wood caressed her, and she rubbed herself against it, unconscious of the movement. He raised a brow, but did not move to stop her. She ground down; the motion caused the plug to move. She pushed harder.

'What are you doing?” He sounded faintly amused.

She inhaled sharply. “I-I am sorry. I-I don't know what happened. I just … was trying to find my balance.'

'Really? And that's why my desk is slimy now?” He didn't sound amused any longer.

'Please. Please, I can't take any more. Get this thing out of me, please! I'll…” she trailed off. I'll do anything, she had been going to say, but she'd already made that promise, and here she was begging to break it. “I'm sorry, it's just too much.” She hung her head, ashamed. A failure already. Failing him.

'Lie back.” His voice was so soft, it took a moment for her to understand. “Feet on the table, here.” The straps on the heels had a purpose, she realized. He fastened her down, spread wide; arms cuffed behind her head, she was opened to whatever whim might strike him. At least he won't be putting things up my ass. She smiled bleakly.

'Just this once,” he whispered in her ear. He sat in his chair, reached out a single hand, and stroked her clit. Nothing more was needed; she came instantly. The orgasm pulsed through her system, radiating out from her core. She was shocked by its intensity, its duration. Its focus. Her body clenched around the plug, caressing, welcoming.

Disgust, and shame, and pain, and pleasure. All at once. She wept, and begged for more.

'Not now. Go to lunch, go to your classes. I'll see you tomorrow.” He released her, helped her to stand. She walked to the door in a daze. Had an attendant not met her in the hall, she would have gone to lunch still cuffed and dressed in nothing but a cape and heels. And anal plug, of course.

* * * *

Carolyn felt like a stranger in her own body. Stretched around an anal plug-disgusting thing, she thought-newly cleansed by a painful enema session, glowing with aftershocks of a glorious orgasm, and primed for many more. Her ass ached; sitting was torture. The plug shifted with her every moment, and she could not remain still. What was happening to her?

'Punishment drill, eh?” A vaguely familiar-looking student leaned across the table, looked deep into her face, and nodded. She poured a glass of water. “Here, drink this. You probably need it.” Carolyn nodded her thanks, unable to find words. “It gets easier, or you get used to it, or something. Have you eaten today?” Carolyn shook her head, uncertain. What day is it? she wondered, but could not gather the strength to ask. The other woman rose from the table, appearing again in a moment with a mug of creamy soup. “Easier than solids. Go on, take it.” She folded Carolyn's hands around the cup, waiting until Carolyn took a sip to return to her seat.

Carolyn managed to drink the soup, and found the strength thereafter to nibble a bit of bread. Her companion nodded encouragement and introduced herself. Sherry was a redhead with the characteristic peaches and cream complexion of an English countrywoman and breasts like pillows stretching her shirt. A junior, she was eager to be “out in the world,” though she planned to return from time to time. “To keep my hand in, don'cha know,” she laughed. She smiled a lot, and Carolyn found herself grinning in return. Reaching for a roll, Sherry's shirt gapped open, a button slipped free of its buttonhole.

Carolyn gasped in shock at the weights depending from Sherry's nipples. “Doesn't that hurt?'

'Of course. That's the point.” Sherry laughed, unconcerned. “'Pain and pleasure will come to you,'” she quoted. Shaking her shoulders gently to make her breasts jiggle, she continued, “I've got a full pound of weights on today, and they'll probably add another after supper. From my nipples again, or from my labia. Makes a good display, don'cha think?'

Carolyn could only gape. Display! Was that to be her future here? She couldn't imagine the pain, the torment, she would feel in Sherry's place. The humiliation was only too clear. At least the plug is inside, she thought, then castigated herself. There is nothing good about that thing. No matter what you might have felt, things are not supposed to go back there! It's unnatural. Disgusting.

It had felt kind of nice, rubbing against her vaginal wall from the other side. Intense. Remembering, she squirmed in her seat, the ache of her ass and the internal caress combining in an odd sort of pleasure-pain. She pushed down into her chair.

'I'm pretty sure you're not supposed to do that,” Sherry remarked. Carolyn looked up. “They usually tell you outright not to masturbate, but even when they don't, you're not allowed to pleasure yourself. ‘Pleasure and pain,’ remember?'

'I-I wasn't…” Carolyn couldn't continue. Wasn't what? Pleasuring herself? Of course she was. No matter what she might feel about the idea, she was enjoying the way the plug felt. But it's not right!

And the whispered thought came, Says who? Her mouth dropped open.

Sherry smiled, shook her head, and reached for a piece of fruit. The rest of the meal passed in silence. Carolyn spent the time trying to convince herself that the anal plug within her didn't exist-in which case, she wouldn't have to decide how she felt about it. As her body kept repositioning itself to accommodate the object, she didn't have much success.

* * * *

Freshman orientation was taught by a man no more than twenty-one; Carolyn had trouble thinking of him as a teacher when she saw him in the halls, but in his classroom, he was perfectly in control. She wondered about that. Was that something that could be taught? Was it taught at the Academy?

Is it something they teach in the outside world? And why didn't anyone ever teach me?

Not that it mattered anymore, but it bothered her to think of it. Would her life have been different if she'd had the right teachers? Well, I have good ones now. Even if I haven't learned how to masturbate yet. She'd sat in on an evening workshop, but been forbidden to participate.

Orientation was concerned largely with The Rules; regulations, commands, litanies. Obedience. Carolyn had no trouble memorizing the rules, but following them was another matter entirely. And drained by her experiences and the constant stimulation of the plug in her ass, she was having difficulty staying awake.

The teacher decided to make her an object lesson for the rest of the class. “Carolyn, over.” By the hand motion, that meant “bend over the table,” so she did. Her skirt raised above her ass, and gasps from behind her told her that her underwear concealed bruising as poorly as it did anything else. “Plugged, I see,” he mused. “Face the class, and describe your transgression.'

Turning to obey, Carolyn wondered at the phrasing. Was plugging, then, a punishment? Was she not supposed to enjoy it? A secret thrill ran through her. “Another student used her mouth on me while I slept. My transgression was enjoying the attention; you see the attention my tutor gave me.” Too late, she worried how that might sound. “This was fifty strokes.'

'Next time, perhaps you will remember the second rule. Raise your skirt, and display yourself again.'

She did, blushing. The teacher began to discuss technique, using her bruises as a teaching aid. “This pattern