by Pearl Jones
So long! she thought. So thick! She shuddered as she pushed, feeling the flare of the head, the gradual thickening of the shaft, textured bumps and ridges. She wondered if it would ever end, and part of her wished it would not, the intrusion so like intercourse, but more intense. Panting, she spasmed, mini-orgasms presaging ecstasy. She reached the base at last, and stopped, gasping for breath, then began to pull it out, miming the action of a real cock.
In and out she pistoned the tool, pulling out the length of the shaft, pressing it home, faster and faster as her orgasm built. Some students began to egg her on, shouting encouragement, chanting, but she barely heard. She was completely focused on her need. The noises she was making would have embarrassed her if she had noticed them, high-pitched yips and dog-like barks and moaning. Her body thrashed from side to side, ass flying, arousing many in her audience, but she didn't care. All she wanted was to continue.
"Stop,” her tutor said. She froze, unbelieving. “Tell me, are you enjoying yourself?"
"Yes,” she whispered.
"Aloud, please.” She could hear the smile in his voice. Closing her eyes, wishing him to Hell, she repeated herself. And again. “Beg,” he said.
"Please, sir, please. Let me come.” Beyond shame now, hanging seconds away from her pleasure, she pleaded. “Let them see me come.” That might sway him.
He turned to the audience. “This girl, Carolyn, thinks anal penetration is unnatural. A sin, even.” He changed his pose, the tone of his voice, suddenly girlish. “It's disgusting to stick anything up your ass.” Back to himself, all confidence and strength. “Or so she says.” Jeers and laughter met his words, and he held up a hand for silence. “I decided to teach her to enjoy the unnatural. How do you think I did?” He drawled the last sentence, confident in their approval, and they gave it loudly, whistling and clapping and shouting praise. He turned to Carolyn then. “Come, girl. Show them how much you love it.” And she did, frantically moving the dildo in and out, withdrawing it fully and forcing it back inside, orgasms tearing through her, melting one into another. She came to the sounds of the cheers, the laughter, collapsing onto the table at last, still coming, the dildo buried completely within her. Aftershocks moved through her even as dinner was served, and she lay there, naked and quivering and sated at last.
* * * *
"Rise and shine, Carolyn. Your public awaits.” His voice, beautifully deep and dark, woke her from her doze. She blinked, for a moment not knowing where she was. Memory flooded back, and she blushed even before she opened her eyes to see every gaze upon her. She moaned her embarrassment, screwed her eyes shut, turned her face away. “Now, now, Carolyn. You know the rules. Display.” Very quietly he added, “Before you drown us all,” and she flushed to the roots of her hair, feeling the truth of his statement.
What happened to that lovely numb feeling? She struggled to her knees. She kept her eyes closed, but it didn't help. She knew everyone was watching. She posed, ass high, knees spread, feeling cool air and hot gazes and shame and arousal and a dildo buried in her rear.
"Reach back and pull the dildo out, slowly."
She obeyed as if in a dream, slow withdrawal a pleasure and a torment. Gasping softly as the flared head pressed against her sphincter, she sighed as the muscle closed. “Now clean it.” Still refusing to open her eyes, she swallowed and brought the tool to her mouth. Should I be grateful for the enema, she thought wryly, or just disgusted? She concentrated on the dildo, trying unsuccessfully to forget the audience enjoying her shame. “Enough,” he said. “Now say thank you to your fans for their attention."
Her eyes flew open. He couldn't mean ... of course he could. Her chest heaved, body clenched, panic reaction making everything painfully sharp and clear. She could hear the attendant breathing, feel her tutor's exhalation stirring her hair. Her shoulders pulled back, leash jerking her down again. She panted.
"We're waiting,” he said softly, his voice kind. She looked up at him, eyes traveling up from the erection stretching his pants to his face, smiling gently. Her panic faded, replaced by desire and a strange sort of pride, that she could excite him. She locked her gaze with his as she spoke.
"Thank you, sir, for honoring me with your attentions. I hope you shall always make the effort to correct me when I need it. And thank you for allowing my peers to witness the pleasure and the pain you granted me.” She smiled up at him, and turned her face, though not her eyes, toward the audience. “I hope that you enjoyed the show.” Her clit throbbed as she laughed. The audience applauded as the bell rang signaling the end of the dinner hour.
"You enjoyed that, didn't you?” His voice quavered as he tried to stifle his laughter. She nodded, still looking deep into his eyes, smiling. “And when tomorrow I have you placed in stocks by the front door, will you enjoy that as well?"
She considered, shrugged. “Will you be watching?” He didn't answer, just took the dildo from her hand and plunged it home. He twisted as he thrust, and the sensation pushed her to new heights of pleasure. Her tears then owed nothing to shame.
CHAPTER EIGHT
A BURNING BRAND
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 sa
y, 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 stud
y 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!"