The Schooling of Carolyn [Academy for Discipline #1]

by Pearl Jones

  "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.

  CHAPTER NINE

  A CANDLE IN THE WIND

  Carolyn sat by Jack, eating her dinner, and grinding discreetly in her seat, enjoying the way she felt. She was double-stuffed that day, vaginal and anal, and though she'd been numbed inside and out to prevent climax, the cream was wearing off.

  Jack, beside her, offered a knowing smile. Carolyn shrugged, unconcerned, and watched as the older woman's smile faded into a pensive frown. “What gives?"

  "It's that girl in the corner, Jennifer. She reminds me of someone...” Jack trailed off.

  Carolyn took one look and had to laugh. “Yeah, Norma Jean. My God, the tutors must be in Heaven! How much would you bet she looks just like her when she comes?"

  "Norma Jean? And, by the way, that's phrased wrong. It should be ‘what’ would you bet; we don't wager money here.” The lascivious grin left no doubt about what was wagered.

  Carolyn felt a small thrill shiver through her just at the thought. There was a certain dream she'd had, once, where she was a flower ... “Norma Jean. Better known to her admiring millions as Marilyn Monroe. The face isn't perfect, but the body is, and the lips. I can just imagine what my tutor would do with her.” She shivered again, jealousy and something darker turning, a strange desire to be the one to command this weeping girl.

  For Jennifer was weeping, soundless but shaking, tears pouring from her eyes like streams in springtime, too full to be contained. Her shirt was wet, translucent, clinging softly, and Jack was not the only one in the room intent on the display.

  "We could find out, you and I,” Jack said, barely more than a whisper. “If she does look like Marilyn then, I mean. When she comes."

  "How?"

  "How do you think, silly freshman?"

  "But, that's not allowed!"

  "So, ask yourself if the game is worth the candle.” A secretive small smile played over Jack's lips then, but Carolyn was too busy thinking to wonder what prompted it.

  "If we did...” Her eyes glazed as she imagined the scene. Blinking at last, she saw Jack rising from the table.

  "Well, come on, then."

  Carolyn stood, and they walked to the corner, other students watching suspiciously. It was obvious that they were up to something. When they sat down by Jennifer, brows raised and whispers began.

  Jack ignored them all. “Hi, Jennifer. I'm Jack; I'm a senior. This is Carolyn; she joined the same week you came here.” Carolyn added her greetings. Jennifer just nodded, not even sniffling though tears still flowed down her face. To Carolyn's darker desires a match was set: Her nose doesn't even redden when she cries.

  There was no thought of obedience in her mind.

  "Listen, some people just take longer to settle in than others. Don't give it a thought. I'm sure you'll get the hang of it here in just a few days.” Jennifer just blinked eyes starred ‘round by wet lashes. “It'll get easier soon; just give it a chance."

  Carolyn felt no least impulse to be conciliatory. She wanted Jennifer to run screaming from the room. Partly so they could follow, partly just for the sight. “How do you get on with your tutor?"

  It half-worked: Jennifer screamed. “Don't talk to me about that ... pervert! The questions, the commands, the ... beatings. My God, you're all insane!” Now she started sniveling, and Carolyn exulted. Trading a glance with Jack, she saw triumph there as well.

  "Sh,” Jack offered, smiling gently at Jennifer all the while. “The bell's about to ring; let's get out of here. I know a place we can talk. A quiet room.” Jennifer nodded, and the three rushed out of the hall before any protest could be made.

  Though the whispers continued.

  By the time they reached their destination, Carolyn could barely contain herself. Simply watching Jennifer walk filled her with ideas—things she never would have thought before the Academy.

  "Dear God, is this how the tutors feel about us?” Carolyn whimpered as Jack physically held her back. Jennifer was curled up on a couch in the corner of the room, seemingly unaware of the spotlight gilding her. Jack laughed softly, hugging Carolyn from behind, half caress and half containment until Carolyn regained her control.

  It wasn't easy. Images of this modern Marilyn half-naked and subdued, not submissive but defeated, glowed before Carolyn's eyes. It had nothing in common with the feelings she'd had in the outside world, and little for what she felt with her tutor, or the various instructors. Even when she was in pain, she never felt any desire for revenge—but this woman she wanted to hurt. And force to enjoy that pain. “What's happening to me?"

  "You're learning, silly freshman,” Jac
k purred into her ear, and followed her words with a half-gentle bite. Carolyn's eyes widened, but Jack gave her no time to truly wonder. “Good cop and bad, and you, my bad girl, had better be bad indeed. It's show time!” And she stepped forward, throwing her shoulders back, leading with her breasts.

  Carolyn heard the murmurs of the other students as they crept into the darkened audience section. Poor Jennifer hadn't realized she'd been taken to a stage.

  "It might help if you talk about it. We've been through it, too, you know. And maybe there's something we could do?"

  "I just ... I just want to go home. I didn't think it would be like this, you know?” Starred eyes wide and hopeful, she curled into Jack's offered arm, sobbing prettily. “I thought it'd be fun, like going to boarding school. Parties in the dorms, and dances, and the stuff the sorority girls do, but organized. It looked nice enough, all upper-class and shiny, but the teachers are all monsters and perverts! And I just want to get out of here."

  Carolyn shook her hair back as she stalked onto the stage. For once, she wasn't embarrassed at the thought of the eyes upon her. Short skirt, sheer blouse, shiny shoes—who cared? She felt like a jungle cat, intent upon her prey.

  Jack looked up with an inquiring raised eyebrow; Jennifer tried to hide behind the older woman. Carolyn smiled. “You did agree to be here, didn't you? The standard two years, like the rest of us?"

  "Yes,” the sobbing, little-girl voice answered, “but I didn't know!"

  "Didn't you? Really?” Carolyn loomed over the seated girl, admiring the heaving, jiggling breasts. Not lust, but something darker, moved in her. “You expect us to believe that you came through those gates, toured the hall, read ‘Your Place Is To Obey,’ and didn't know? Little girl, lie to yourself all you wish, but do not lie to us.” She was hissing by the end, her face inches from Jennifer's, watching the blood fade from her cheeks. She looked so fragile, so delicate. Carolyn was tempted to bite her, to watch her bleed. Red blood over that white skin; she shivered.