For the next month and more, Carolyn was anally trained. Each day brought some sensation, often pain and pleasure combined. She wore plugs to stretch her sphincter, not too far, but a bit; took frequent enemas to keep the area clean; went to class surrounding strings of beads that massaged her when she moved, or gently vibrating eggs. Learned to contract her muscles in sequence, prepared to milk a cock.
She was allowed no vaginal penetration, which necessarily excused her from some of her class work. Those climaxes she was granted-too few by far, for her-all featured anal attentions and discipline. It was part of her tutor's plans for her.
And sometimes, she came without permission. And was punished, often anally.
* * * *
Carolyn pushed back, opening her ass wide for her tutor's inspection. “Relax,” he told her, and she did her best to remain perfectly still. It was hard not to move as his finger broached her sphincter, the feeling as conquering as ever, her body yielding to his will. The breath rushed out of her body; she bit her lip, desperate not to come. She longed to clench tight around his invading digit. But he had told her not to, so she did not.
"Good,” he murmured, and her body broke out in sweat. Her heart pounded, whole body throbbing with her pulse; she was seconds away from coming, but not allowed to come. One word, one touch from him was all that it would take, but he had not given permission, so she tried to resist. His finger retreated, the slow withdrawal a caress, nearly pushing her over. She felt empty without him there, and wished for his return.
He did not leave her vacant for long. Something cool, not too thick; she accepted it easily. He pushed it in, reminding her not to clench. She measured its progress, thrilling to the sensation. It warmed, whatever it was, with her body heat. High and higher it went, its journey easy, reshaping her from the inside out. She panted, body shaking despite her best efforts, stammering out her apologies as she began to come.
And fire bloomed within her as she spasmed. Screaming in pain, she continued to orgasm, white lights behind her eyes beyond pleasure, beyond pain. Sensation, racking her, coursing through her body.
She blacked out from sheer sensation, woke spasming still. Her throat was raw, eyes streaming, bowels burning. “What?” Her voice rasped and tore; she could not go on. Moaning as her body climbed toward yet another climax, she sought her tutor's eyes, locked gazes with him.
He was smiling, laughing gently at her. “I told you not to do that."
She nodded, sighed.
"It's called a fig. That one's essence of ginger. They use it on parade horses, to make them keep their tails up. Looks like it works on you, too.” She waggled her ass helplessly, feeling the burning; he patted the nearest cheek and went on. “Usually they're placed just inside the anus; I thought it might be fun to put yours further up. Tell me, how does it feel?"
She knew what he wanted her to say, and meant to say it. But when she opened her mouth, what came out was thanks. “Thank you, for honoring me with your attention. For thinking of me, teaching me, everything. Thank you for-ooh-this gift of burning. I feel,” her body shaking, heartbeats from coming yet again, “I feel your touch everywhere.” And she collapsed again into orgasm, body sore and yet exultant.
He laughed and shrugged and let her come. Again and again and again until the burning faded. And then he told her she'd be feeling it again. “I think I'll send you to class gingered. The other students should find the lesson interesting.” She shook, sobbing, her body raw and aching and oversensitized. The mere thought of it, of walking into a classroom, sitting down, all those eyes on her … she knew there was no way she'd manage not to transgress multiply.
"Perhaps I'll make it a ceremony. You haven't been on the dining hall stage in weeks. Yes, I think I like that thought. Make you ask for it, tell everyone what you're feeling once it's in.” He watched as her body struggled not to orgasm, too-sensitized flesh red and weeping as she came. Her eyes rolled back and she went limp, not exactly unconscious, but too weak to move.
Distantly, she heard the scratching of pen on paper; she had no strength to wonder what he wrote.
* * * *
One evening, she was summoned from a workshop. Afraid and curious and excited, she followed the attendant to a small receiving room. It looked like the Victorian sitting room she had seen in her history books, all crowded full of tiny bits of furniture. She blinked, trying to pick a clear path through the room, and only belatedly saw the Anatomy and Physiology instructor, Grace.
"You summoned me? Ma'am?"
"Yes."
For a moment there was silence, as Carolyn wondered if she'd missed a punishment-she didn't think she had, but what else could this meeting be?
"Sit down."
Carolyn sat, carefully. She was unplugged, for once, so it wasn't fear of pain that moved her to caution. Half her care was concern for the chair, the other half simple attention to the rules: A student must move gracefully, no matter the strain. She hadn't started dance and movement classes yet, but that was no excuse should an instructor decide her movements were unacceptable.
"Tea?"
"Ah,” something to spill? I'd really rather not. Can I say no to an instructor? Say yes and just put it on the table, that's safest. “Thank you."
"Relax. I'm not going to bite. Tonight.” Grace smiled, and Carolyn was struck once again by just how attractive everyone at the Academy was. The instructor wasn't beautiful, it wasn't that, but she glowed with health and confidence and contentment. Her body was lightly muscled, very toned, and the catsuits and thin wrap dresses she favored showed off what she had every right to be proud of.
Like everyone here. They're not all tiny, like she is, but there's no one gross. Well, except Bertha.
"Would you care to share the joke?"
"Oh, sorry. I was just admiring your dress."
"Yes, the uniforms do get a bit tiresome, don't they? Unless, of course, your tutor is one of those who prefers to see every inch of skin?"
The predictable flush rose.
"Ah, he is. Tell me about him?"
Carolyn opened her mouth, closed it. What do I say? She knew better than to complain, though, honestly, there wasn't much she could have criticized. He humiliated her, often; hurt her, forced her to do things she didn't want to do. Gave her more pleasure than she had ever known. He devised torments and made her cooperate in her own debasement, or ordered her to do impossible things just so she would earn another punishment. Sometimes he punished her without any reason at all.
She loved every minute of it, and yearned for more.
Grace was still waiting.
"He is very…” Sexy. Intelligent. Yummy. “…focused. And very good at what he does."
"And what is his focus?” Judging from her smile, Grace knew full well. Considering the various scenes Carolyn had been made to enact, she would have to have been blind not to-or dumb, and none of the instructors were that.
"He is an ass man."
A peal of laughter was Grace's only reply; Carolyn didn't know why she laughed, but didn't ask. Safer not to. They drank tea, or rather, Grace drank and Carolyn sipped, and talked about classes and homework, and then Grace set her cup down. “How do you feel about what your tutor asks of you?"
Carolyn choked on a laugh of her own. “He doesn't ask.” But that wasn't an answer. She took a breath. “I never knew. All those years, I just never knew it could be like that. He … I didn't want to do what he told me to, but when I did, it felt … even before it stopped feeling bad, it felt so good…"
"Stop. One sentence at a time, please."
She shook her head, feeling the breeze on her overheated cheeks. “I always thought it was disgusting, thought even gays only used their mouths and, and their assholes ‘cause they didn't have anything better.” She stopped to see if that was clear enough; Grace motioned for her to go on. “I was so excited when he chose me, but the very first time I reported to him, he told me to put my finger up my ass. And I just-I was so disappointed he was a pervert.
"But, ‘your place is to obey,’ so I did. Eventually. And it didn't feel like I expected it all. Which kind of figures, because I didn't know anything when I got here! I just thought I did."
"A lesson well learned,” Grace murmured. “Continue."
Carolyn shifted in her seat, caught herself. Just the thought of her tutor made her wet. Wetter. I've been wet since the day I came here. “He taught me to enjoy anal play."
"Is that what you call it? When you're thinking about it?"
"Well, no. But you've said it, in class."
"We aren't in class now. What do you call what he does to you?"
Carolyn sighed, “heaven,” not loudly enough to be heard. In a normal conversational tone, she replied, “Ass-stuffing. Or butt-plugging. Things like that."
"Not terribly elegant terms. Has your tutor started you on language lessons yet?"
"French.” She winced. She wasn't doing very well with that; it seemed sometimes like her tongue just didn't fold the right way. And understanding what other people said was almost as hard as trying to speak, sometimes. She'd catch the meaning more often than the words. Maybe another vocabulary drill before bed. But I can't worry about that right now! What was she talking about? Oh, right, what classes I take.
"And English?"
"You mean, like, literature? Not yet."
"Well, we shall have to speak of that. But for now,” Grace poured more tea, “you and I shall simply talk."
"About what?"
"Oh, sailing ships. Sealing wax.” The smile said it was a joke; Carolyn didn't get it. “Never mind. It's a literary reference, and you said you're not taking that yet. Tell me about your favorite class-other than mine, of course."
Favorite? God, how to choose? Discipline terrified her, but it was fascinating. Law 1 was bizarre, but she “transgressed” quite a bit in that class. History was nothing but stories, sexy and funny and weird … “History,” she said. “I like history. The way they teach it here."
"And what have you learned in history? One example."
"Did you know Cleopatra had a vibrator? All those years before electricity. The Victorians, too. They used water power…"
* * * *
That odd conversation stuck in Carolyn's mind; what had its purpose been? She completed Orientation and was told to report to a different room one day, for lessons in Elocution. Perhaps that had been the reason, to see what she needed to learn.
But there had been something in Grace's eyes, an odd light when she asked what Carolyn called the things her tutor did.
She couldn't have heard what I said, could she? No, of course not. Besides, what does it matter? I came here to experience, and to learn to enjoy. And God knows, I'm doing that.
* * * *
Academy students had no days off, but there were weekends of a sort-workshops and study periods, longer sessions with tutors, even the odd hour free just to rest. Carolyn had been enjoying one such when an attendant came to fetch her; she went eagerly. No matter how sore she was from his attentions, she was always eager to see her tutor.
"You haven't been corked yet,” he said by way of hello.
"No, sir.” Oh, God, please. I've been waiting so long…
Her expression must have shown her hope; he shook his head. “You haven't earned that yet. But I think you're ready to move a step closer. That is, if you don't have anything better to do?"
The tips of her ears burned, so hot was the flush. Someone told on me. Tom. I'd bet anything. She'd said it a few days before, when a teacher was called out of class and left them there nearly the full period.
"No,” he said as she opened her mouth, “don't apologize. You'll report to the instructor you insulted, for whatever punishment she deems appropriate."
"Yes, sir,” she sighed, and turned toward the door.
"Did I tell you to leave?"
She smiled at the tone of his voice. It went velvet-dark when he was about to test her limits; her body reacted to the sound as to his touch. “No, sir. I am sorry, sir. I'll try to do better. I do not ask your forgiveness."
"Mm.” He looked at her for a long minute, then reached into an open desk drawer. His other hand patted the top of the desk in a familiar command. “On your back."
She arranged herself for his pleasure, folding her skirt up so it would not obscure his view, removing her panties, bending her legs and pulling her knees to her breasts, holding them there.
She felt the tip of his finger press against her anus, opened eagerly. Lubed, it slipped in with only the usual reflex resistance; she pushed as best she could to help him. Too soon, he pulled away. A cool something knocked where the finger had just been.
It was much wider, and her position meant that she couldn't help, but only receive. She shivered, feeling the slow, slow increase in pressure. He was teasing her, she knew. It was hard to remain still; she wanted it inside her. “Please!"
"Remind me."
Oh, damn. She knew what he meant; she had just earned a punishment. At least he didn't stop-thought fled as the whatever-it-was broached her sphincter. Very wide; she felt the stretch, the pain so much like pleasure there was no proper word. He left it there for a timeless moment, then pushed in. She felt the snap as her body closed around the shaft, another yielding as he pushed its length home. And then a pause.
"How does it feel?"
"Wonderful,” Carolyn sighed. The molded cock had ridges she had felt as they passed; could feel now if she squeezed. The mushroom head almost too wide but not quite, shaping her from the inside now; shaft hard and slightly yielding, almost like flesh, like his fingers, like she imagined his cock would be. She pushed her ass up as best she could, silently begging for more.
"Are you really saying what I think I just heard?” Mocking tones, but no cruelty; Carolyn didn't even blush. She just nodded, a slow, languorous gesture, and tilted her hips.
"Tell me. Properly."
"Sir, it's wonderful. I am filled, as you have taught me to be. And to enjoy being. I love having things stuck up my ass, I was made to be plugged. You had the wisdom to see that, and to teach me."
"Flattery? How quaint. Do you remember what you first told me, when I had you plugged?” Now she blushed, at that memory. “Tell me again what you said."
"I told you it, the plug, felt like a burning brand."
"So, if I ordered you to take a stick up your ass, would you?"
"Of course, sir. And thank you for it, too."
"And if it were on fire?"
"My place is to obey."
"Very good.” He patted her ass. “You may come.” And just like that, with no other stimulation, no thrusting, no kissing, no writhing, she exploded into ecstasy.
He sent her to class still surrounding the dildo; she went with pride. More than by his latest plug, she was filled with hope.
Will he cork me soon?
* * * *
The teacher she had “insulted” hadn't told her what her punishment was going to be, but some of the students had given her odd looks as she followed the attendant toward her doom. She knew what that meant: someone had indulged in whimsy. It was enough to make her blood run cold-the instructors were not above inflicting a fair amount of pain for the sake of some joke, and they often collaborated. And her tutor had made a point of telling her he knew what she had said.
As scared as she was, she was also so wet she sloshed with every step. He would be so proud. She tried to remember everything he'd said during that session. Nothing seemed like a clue.
"Ooh.” Carolyn stopped in the doorway of the tiled room, shock freezing her in place. She hadn't seen Sherry for a few days, and had wondered what new torments were being visited on her friend, but had never imagined this!
The young woman hung suspended from a sort of hammock made of webbing, tubes hanging from the ceiling, disappearing into her ass. Two of them. Some odd cup-like structures enveloped her breasts; a water bottle was hanging by her head.
Her head hung low, fiery hair veiling her face. Her stomach was distended. And as Carolyn watched, she began to buck. Like a half-broken steed protesting a rider, she threw her body back and forth, but there was no escape. Whirring sounds echoed in the tiled chamber, as did Sherry's sobs and cries.
And then the whirring ceased, and Sherry fell motionless again, and the attendants prodded Carolyn into the room. One bleary red eye crept open, and Sherry bent her lips into a grin. “Hey, kid, what are you in for?"
"The usual, I guess. And you?"
"Definitely not."
An attendant slapped Carolyn, almost gently, on the ass, encouraging her not to dawdle. Obediently, she let herself be strapped onto a slant-board, manipulated and teased almost to orgasm. And then they were alone.
"I was stupid,” Sherry sighed. “My tutor's been working on teaching me milking, but I'm just not much good at it. I was frustrated, and very, very horny, and I made a crack about milking being for cows. So,” she shook in her webbing, “here I am. Behind is some sort of devil's brew of herbs and hormones, and up front we have the twins. Constant suction all over my tits, plus stronger pulls on my nipples a lot of the time.” She stopped for a sip of water from the bottle by her head. Voice shaking a bit, she said, “I think they're going to turn me into a cow. And I think…” She shuddered. “Here it comes again."
Carolyn watched, wide-eyed and fascinated, as the distended belly shrank, then stretched again. Sherry's breasts were completely covered by the contraption, but her shoulders moved back and forth in time with the mechanical whirr. She sobbed and moaned and pled for release, for help, for a break. And then, shuddering, she came. A strange orgasm, slow and strong.
Carolyn felt a rush of jealousy. But when it was over, and Sherry hung limp in her bonds, all Carolyn could do was stare in something approaching awe. Her friend glowed all over, skin as rich as cream, hair shining in the light like copper. She seemed softer somehow, silken.
"Wow."
Sherry opened one eye. “My breasts are filling. I know it, they're turning me into a cow. And, God, I can't wait until they milk me."
An attendant stepped into the room and turned to Carolyn. The gloved hands held a very large enema syringe.
The board to which she was strapped was angled, her head a little below the level of her feet. Recent experience had taught her that meant she'd be there awhile. Breasts bumpy in the chill air, she stared at the approaching figure, wondering what it would be this time.
There'd been heat and cold, something that smelled like fresh grass and left her wired for hours, stinging mint-scented soap and something that blurred the edges of the world for a time. She'd been left lying for what felt like days, might have been hours, been plugged and made to walk around the room, been introduced to a machine that flushed her insides like an internal shower.
But her tutor never let her get bored with repetition. So she shivered as she lay there, open, helpless, afraid. And aroused, as she always seemed to be. In odd quiet moments she marveled that sex had so escaped her notice before, when she'd been a small-town beauty, and then a small-time wife.
If she'd known then what she did now, what would have changed? But those thoughts quickly faded from her mind. Even in the midst of being punished, hurt or humiliated, she was aroused. She didn't want anything to be different, except that she always, always, wanted to be allowed to come. Even now, as she waited for the syringe, wondering what concoction would soon make its way inside.
Sherry began to stir. Carolyn couldn't see her, but the noises were easy enough to understand. The whirring as she was suckled, the soft liquid sounds as she was emptied and refilled, the moans and cries as she came again. The groaning, climax almost more torment than release. And the yearning for more, even so. Always, more.
Carolyn gasped as the nozzle was pushed into her anus, thrust hard. The feeling was always startling, always new. A sudden change, her body adjusting to something, someone, shifting obediently, surrendering.
It pushed in, hard and demanding, a plastic shaft, and she shook, needing to come, bound too tightly to move the slightest bit. It traveled deep into her, defining bits of herself she could only feel when they were being used, and she could do nothing but endure. And smile, and sigh, and revel in the feeling. And try desperately not to spasm, not to climax.
The attendant fucked her with it a few minutes more, then thrust it fully in, to the bottom of the barrel. Her sphincter clamped down, holding it in place. And then the plunger, and fluid heat.
Warm, warmer than her flesh, it crept within. She thought it quite nice for a second, until it started to itch. In a heartbeat, she was shrieking, cries bouncing off the walls. The attendant patted her clit softly and walked away. Leaving her itching, tied too tightly to move, feeling like she had poison ivy on the inside of her skin.
And needing, always, needing to climax again. But the itching distracted her too much even to think, so she didn't consider using the milking techniques she had been taught to give herself some relief. Even if she had, it was doubtful she could have succeeded. Every muscular contraction made the itching that much worse.
The whirring came again, and Sherry, too, began shrieking. A chorus of half-pleasured torment rang from the walls. Sometimes there were words; they begged their tutors for release, for relief, forgiveness for whatever their transgressions. Sometimes there were only cries.
At one point, Carolyn screamed, “Ants!” The answer to the puzzle: Tom again, that bastard, and the tutors with their humor. She even managed to laugh-but the motion made the itching even worse.
* * * *
Sherry appeared for dinner one night; she took a seat near Carolyn and Jack, nodding a silent greeting at the two. Her glow had, if anything, increased, as had her cup size, impressive, as she'd been at least a D before. Now her breasts were massive pillows with thumb-like nipples sticking up, bursting out of her top, too ripe to contain. And halfway through dinner, they began to spurt, first one, then the other, tiny jets like miniature cocks.
Sherry began to cry, as Carolyn sat, staring. A tutor spoke up from her table. “Tom. Suckle Sherry until she's dry."
An aside to someone, “If that's possible.” Tom grinned his jackal grin, bent Sherry back, put his mouth to her nipple and bit down. She screamed, he laughed, and then he began to suck. And the look on his face changed.
Carolyn's clit throbbed. He looks like he's trying to be disgusted but can't pull it off. In fact, he looked like he was enjoying himself a great deal. But perhaps wishing that he wasn't. He spat out her nipple, looked cross-eyed at it, and shook his head. Took the other one in his mouth, gently this time. Laved it with his tongue, then sucked it, drinking her milk down.
Sherry clasped his head to her and shook as she came. Not once, or severally, but seeming constantly, he suckled and she spasmed, on and on.
Carolyn darted a glance at Jack, who seemed spellbound. As did everyone else in the hall. A mother suckling a babe is somehow sweet, a woman suckling a grown man is bizarre. A woman getting off on it … was appropriate for the Academy. As was his reluctant pleasure in feeding from her.
His eyes shone, suspiciously like tears. “She's empty."
"Are you sure? Check the first breast again."
Tom leapt to obey, ignoring the sound of chuckling, cheeks hollow with his efforts as he sucked her dry again. When he thought he was through, he switched, tugging ever harder, then finally took both nipples in his mouth at once.
"She's dry,” he said with confidence.
"Then go finish your dinner."
Sherry collapsed back into her seat. “I'm a cow,” she whispered to Carolyn. “Ain't it great?"
Carolyn could only nod and squirm in her seat, imagining herself in Sherry's position, breasts grown and filled and emptied at another's whim. She wasn't sure there were words for what she felt. But she knew one thing: if her tutor chose that path for her, she'd take it.
She looked up and met his eyes, and, unblinking, came. He watched as she spasmed, holding her with his gaze. When she had finished, he raised one eyebrow; she bit her lip. He reached into a pocket and pulled out something brown. It looked very like a stick. With one hand, he motioned to her; the other brandished a lighter. Blushing, she rose and went to him.
Quivering, already desperate to come again.