Earning His Orgasm

"Making him validate his obedience to earn an orgasm"

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John swallowed again, his mouth dry as he forced the words out. “Rule number two: I must eat all of my own ejaculate or never be allowed to cross-dress again.” His voice trembled, humiliation and arousal mingling in a way that made his cheeks burn. Amanda’s lips curled into a satisfied smile, her eyes narrowing with pleasure at his discomfort.

Good, she thought, leaning back in her chair. He needs to feel this. She crossed her legs slowly, the movement deliberate, knowing how much it affected him. The soft swish of her skirt brushing against her thighs was enough to make John’s breath hitch. She could see the strain in his posture, the way his hands clenched at his sides, trying to resist the urge to touch himself.

“And what happens if you don’t comply?” she asked, her voice low and teasing.

“I…” John stammered, his gaze dropping to the floor. “I lose the privilege of dressing up.”

Amanda chuckled, a deep, throaty sound that sent shivers down his spine. “That’s right. So you better be very careful, darling. Or else your little frilly dresses will stay locked away forever.” She tilted her head, studying him like a predator sizing up its prey. “Wouldn’t that be a shame?”

John’s throat tightened, his heart racing. The thought of losing that part of himself, even temporarily, was unbearable. “Yes, ma’am,” he whispered, his voice barely audible.

“Louder,” Amanda commanded, her tone sharp. She wasn’t about to let him off easy. Not today.

“Yes, ma’am!” he repeated, louder this time, though his voice still wavered.

“Better,” she said, nodding slightly. Her foot, still bare from her earlier pedicure, brushed against his knee again, the contact sending a jolt through him. “Now, rule three.”

John took a deep breath, forcing himself to focus. “Rule three: when I… when I ejaculate, I must eat it off your feet or a plate while kneeling in front of you.” His face burned hotter with each word, the humiliation almost too much to bear. Yet, despite it all, he couldn’t deny the twisted thrill it gave him—the surrender, the submission, the way her dominance made him feel completely hers.

Amanda’s smile widened, her satisfaction palpable. “Very good, darling. And why is that important?”

John hesitated, his mind struggling to find the words. “Because… because it reminds me of my place,” he finally said, his voice trembling. “It reminds me that I belong to you.”

“Exactly,” she purred, her foot sliding higher up his thigh now, her toes grazing the edge of his panties. He tensed, his breath catching in his throat. “You belong to me, John. Every part of you. And don’t you ever forget that.”

He nodded quickly, his body trembling under her touch. “I won’t, ma’am. I promise.”

Her foot moved away, and she leaned forward, resting her elbows on her knees as she studied him intently. “Rule four,” she prompted, her voice firm but not unkind. There was a method to her cruelty, a purpose behind every word, every touch. This wasn’t just about control—it was about shaping him, molding him into exactly who she wanted him to be.

John swallowed hard, his voice shaky but determined. “Rule four: when I’m allowed to cum, I must do so wearing lingerie and with my ass plugged.” He paused, his cheeks flushing even deeper. “And… and I must beg to continue being your weekly maid before being allowed to finish.”

Amanda’s eyes gleamed with approval. She loved this part—loved watching him squirm, loved hearing him recite the rules that bound him so tightly to her. “And why is that necessary?” she asked, her tone light, almost playful.

“Because…” John hesitated, his heart pounding in his chest. “Because it reinforces my obedience. It reminds me that my desires are secondary to yours.”

She smiled, a slow, predatory smile that made his stomach flip. “Perfect. You’re learning, darling. Slowly, but surely.” She reached out, her fingers trailing along his jawline in a gesture that was almost affectionate. Almost. There was still an edge to it, a reminder of who held the power here.

John’s breath hitched, his body aching for more, for any kind of release. But he knew better than to ask. He knew better than to expect anything but what she chose to give him.

“Now,” Amanda said, leaning back again, her expression shifting to something more serious. “Today is your day, isn’t it?”

He nodded eagerly, hope flickering in his eyes. “Yes, ma’am.”

“Then let’s get started.” She stood, smoothing down her skirt before walking over to the kitchen counter. From the cupboard, she pulled out a small, white plate and set it down on the table. “Kneel,” she commanded, her voice leaving no room for hesitation.

John obeyed immediately, lowering himself to his knees in front of her. The cold hardwood floor pressed against his skin, a stark contrast to the heat coursing through his body. He kept his hands at his sides, his head bowed respectfully as he waited for her next command.

Amanda strolled over to him, her heels clicking softly against the floor. She stopped in front of him, her presence towering over him in a way that made him feel impossibly small. “Look at me,” she said, her voice calm but firm.

He raised his head, his eyes meeting hers. The intensity of her gaze made his breath catch, his heart pounding in his chest.

“Do you remember what happens if you don’t follow the rules today?” she asked, her tone casual, as if they were discussing something mundane.

“Yes, ma’am,” John whispered, his voice trembling. “I lose the privilege of cross-dressing.”

She nodded slowly, her expression unreadable. “Good. Then let’s make sure you don’t mess this up.” She stepped closer, her foot brushing against his thigh again, this time with more pressure. “Ready?”

John’s entire body quivered with anticipation, his need for release growing by the second. “Yes, ma’am,” he breathed, his voice barely above a whisper.

Amanda smirked, clearly enjoying the effect she had on him. “Then let’s begin.” She tapped his shoulder lightly, signaling for him to start. “Remember, darling—every drop counts.”

He nodded, his hands shaking as he reached between his legs, his fingers brushing against the lace of his panties. The plug inside him shifted slightly, a constant reminder of her control over him. He closed his eyes, focusing on the sensation, on the overwhelming need building inside him. When he finally came undone, it was with a shuddering gasp, his release spilling onto the plate in front of him.

Amanda watched with a satisfied smile, her arms crossed over her chest. “Good boy,” she murmured, her voice thick with praise. “Now, let’s see if you can follow through on the rest.”

John’s breath was ragged, his body still trembling as he stared at the plate in front of him. He knew what came next—what she expected of him. Swallowing hard, he leaned forward, his tongue darting out to taste the first drop. The flavor was bitter, acrid, but he forced himself to keep going, his movements slow and deliberate.

Amanda’s foot brushed against his shoulder, a silent encouragement—or perhaps a reminder of what was at stake. “Every drop,” she repeated, her voice firm. “Don’t forget.”

He nodded, his tongue lapping at the plate with renewed determination. As he worked, his mind drifted, the humiliation mixing with a strange sense of fulfillment. This was what she wanted—what she needed. And in that moment, he realized there was nothing he wouldn’t do to make her happy.

“That’s it,” Amanda cooed, her voice softening just slightly. “You’re doing so well, darling. Just a little more.”

John’s movements slowed as he neared the last few drops, his breath coming in shallow gasps. He could feel her eyes on him, watching his every move, and it only fueled his determination. When he finally finished, the plate clean, he leaned back on his heels, his body sagging with relief.

“Well done,” Amanda said, her voice dripping with approval. She knelt down in front of him, her hand cupping his chin as she forced him to look at her. “You’ve earned your reward, darling. But remember—this is a privilege, not a right. Don’t make me regret giving it to you.”

John nodded quickly, his eyes wide with gratitude. “Thank you, ma’am. I won’t.”

She smiled, a genuine warmth creeping into her expression. She knew his state of mind after an orgasm would not be very sexual. Making him submit further without being so aroused would be the ultimate show of ownership. “Good. Now, go get dressed Sissy. Remember I own you.” This is a privilege. You have a house to clean.”

Published 2 months ago

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