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Ruby's Lesson


Journey into Submission: The Failure

“Did you complete your task, sweetheart?”

Ruby froze, “I did, sir. But-“

“But?” AJ tilted her chin so he could watch her face and candid gray eyes.

She quivered just a little, took a deep breath and confessed in a rush, “I walked a complete circuit of the mall with the egg..in…in…as directed, Master. But I had it turned to low instead of high.”

His increased tension did not escape her and when he frowned down at her, Ruby’s heart thumped hard in her breast.

In a voice so quiet that it made the hairs on her arms stand up, he said only, “Explain.”

A sick sense of failure welled bitterly in the back of her throat and she shivered as though suddenly cold. “The egg was too loud, Sir, too noticeable. And I did not have permission to cum. When the egg is on high in my…in my pussy, I nearly always cum, M..M…Master.”

By the end of her explanation, as AJ’s frown deepened, Ruby was hiccoughing with anxiety. In all their time together, she had never before seen in him this profound disappointment.

It had seemed such a small transgression. And AJ had heretofore been an indulgent and understanding Master. It had not occurred to her that she would face his displeasure over it.

Her heart hammered heavily behind her ribs: a knell, a portent. Oh god. Oh god, she had failed. It hurt to breathe. She had failed her Master and the enormity of it took her far past tears to a trembling, quivering mass of apprehension.

She sank to her knees before him and whispered brokenly over and over, “I am sorry.” And then, “Master forgive me. I didn’t think it mattered so-“

“You will not always know my purpose, Ruby.” And his voice was so cold, so displeased, that his words fell in an icy shower over her huddled form. She flinched and shook so hard that her teeth chattered.

“Do you consider then that you need only obey those commands that you think matter?”

“N…no-“ she breathed it thickly, anguished.

“Did you think I had forgotten how often you cum when the egg is turned to high?”

“I…” didn’t think I could cum without permission…thought it the lesser of two bad choices…Ruby drew a shuddering breath and settled for, “I don’t know, Sir.”

Her throat ached, her lungs ached, her heart ached and in her misery it was physically painful to speak. She was suffused with a bone-deep sense of panic. She had failed her Master. She would be released. The prospect devastated her.

She gulped air, dragged it audibly into lungs that refused to function properly and whimpered in her pain. “Please, Sir.”

“Please what?” he prompted. Then before she could answer, added, “Look at me when you speak.”

Obediently she lifted her face, shivering. “Please forgive me, Sir.” Had she but known it, her blonde hair held more color than her cheeks.

“Oh Ruby-mine-“ he sighed.

She blinked, uncomprehending, as AJ abruptly gathered her in his arms and strode to the couch where he sat holding her trembling body. He rocked her gently against his broad chest, pressed her face over his heart and chafed warmth back into her quivering form.

“Sweetheart, I will always forgive you.”

And there was such warm ardor in his voice that Ruby began to weep uncontrollably. She wept out her sorrow, her self-disappointment, her relief. Throughout the storm of emotion, AJ kept her wrapped in his arms and murmured soothingly into her hair.

A century or so later, when her tears had dried to faint hiccoughs, he tenderly dried her eyes and kissed her forehead.

“Ready to talk?”

Ruby nodded, blowing her nose into the tissue he handed her.

“You were instructed to dress in your blue suit, put the vibrating egg in your pussy, turn it to high and walk one complete circuit of the mall. Tell me why you did not follow my instructions.”

She took a deep shaky breath and plunged ahead, “Even with the egg deep inside me, Sir, I could hear it and thought others could, too. And I knew that if I left it on high that I would cum and I did not have your permission. So I…I turned it down. To low. Oh Master, I am sooo sorry.”

“I know you are, baby. Did you have reservations about this task before you left to carry it out?”

“Yes, Sir.” She admitted forlornly.

He tilted her chin. “This was a test, Ruby. I expected you to tell me that the egg would be too loud and if you did not think it was so, then I expected you to ask for permission to cum while carrying out this task. Yet you did neither.”

Her eyes widened and she felt her jaw drop. Embarrassed color flooded her wan face. Her Master had given her a task that he never expected her to carry out! Her Master had tested her willingness to point out her own reservations. And she had failed. In her own arrogance and pride, she had seen fit to alter his directions rather than speak up and in so doing she had failed him utterly.

It had never occurred to her that he would test her this way. In a rush, Ruby realized that in failing to comply with his instructions, in failing to divulge her reservations, she had been guilty of topping from the bottom. She had threatened the trust between them – AJ’s trust that she would follow his commands implicitly. And she had no real excuse. AJ always listened to her and sometimes even changed his directions. No, her folly had been in believing that she knew her Master’s goal and therefore thinking that there would be no harm in altering her compliance as long as that goal was met.

She was devastated all over again. Fresh tears welled at the depths of her failure.

“Enough tears, darling girl.” AJ said bracingly, hugging her close. “Have you understood this lesson?”

She nodded, sniffling and wiping at her eyes. “I will carry out your directions exactly as you have delineated them and if I have reservations or questions, I will make them known to you before-hand. To do otherwise,” she added tearfully, “would break your trust in me and would be topping from the bottom.”

He smiled at her with pride. “Exactly. You understand that - even knowing your reservations - my commands may not change?”

“Yes, Sir.” She answered, and then asked with a catch in her voice, “Will you really forgive me? Always?”

Absolutely.” He smiled tenderly at her and stroked his thumb across her damp cheek.

Ruby hugged him hard as her heart leapt. “Oh, Master! Though I had to displease you to learn it, this is a wonderful loving gift you have given me! Knowing that you will forgive me my failures is…is-” she started to cry again in her relief.

“It does not mean that I will forgo punishing you however.”

“P..punish me?” her tears dried magically at this even as her pulse sped to a gallop.

“Yes, lover. You did not obey my command, for this you will be punished. You did not tell me what was in your heart when you were given this command, for this you will be punished.

“The truth is, lover, it delights me to give you pleasure and the thought of you cumming - perhaps even moaning softly – while touring the mall in your prim teacher’s clothes gave me a huge erotic charge. Your actions denied us both. For this you will be punished.”

She stared intently into his beloved face, took a couple of deep breaths and tilted her trembling chin.

“I understand, Sir. I am proud to be yours.”

“I love you, my jewel.”

She caught her breath on a low moan as an orgasm rolled over her in a cresting wave of exquisite release. AJ had confirmed for her weeks ago that ‘jewel’ when spoken by him did indeed trigger her climax although he had long since removed the hypnotic post-suggestion that originally accompanied the word. She had been conditioned to the trigger long enough that it worked without hypnosis.

AJ held her close and murmured; “You please me well, darling Ruby.”

Journey Into Submission: The Punishment

That evening, Ruby presented herself to AJ wearing only her basic attire: her collar engraved with Celtic knots and adorned with two rubies, 3-tiered nipple chain hooked through nipple rings, black lace silk stockings and tiny garter belt. She wore her hair loose about her shoulders and went shoeless at his orders.

“I am ready, Sir.”

She trembled a little before him, unable to look away from the leather crop lying upon the table. Next to it was something floating in a bowl of water. Ginger, she thought, with a sniff. Gingerroot that had been peeled and shaped…shaped like…Ruby swallowed hard.

“Come here, baby.” He patted his lap and smiled warmly.

With a sigh of relief, she sat in his lap and curled into him. AJ put one arm around her shoulders and cupped her hip with his other hand. His breath stirred the hair at her temple. She licked and kissed his neck; quick flicking licks and sucking kisses.

“Did you see what’s in the bowl, baby?”

“Ginger, Sir?”

“Correct. What shape would you say it is?”

She shivered, “It is shaped like a small ass plug.”

“Yes.” He rewarded her with a claiming kiss and Ruby melted into him with a murmur of joy. He stroked his tongue along hers, nibbled on her full lower lip, sank his heated claim deep into her moist receptive mouth.

When he at last lifted his head, she gasped for air while he asked, “Have you heard of ‘figging’ Ruby?”

She wrinkled her brow in thought. “An old English custom wasn’t it? Something to do with anal play, ginger, and spanking or c..caning.” She stuttered as she recalled the crop.

“Exactly. I’m impressed, love. You have been doing your homework.”

Her blush spread upwards from the tops of her breasts to her entire face at his praise. It was a ceaseless joy, that mere words from this man could give her such physical pleasure.

“Figging refers to the practice of inserting gingerroot into the ass of one about to be caned. The ginger…heats up and prevents the disobedient one from clenching their ass.”

‘Disobedient’ echoed over and over in her brain and locked up her throat.

“There will be no damage to you from the ginger. Do you trust me, Ruby?”

“I do, AJ-sir.” And as she spoke this affirmation, she relaxed.

“Good girl.”

He grinned at her and tugged the nipple chain taut; teased and pinched her nipples, drawing his fingernails over the hardened flushed rosebuds. Ruby whimpered at the loss when he detached the chain and dropped it in his pocket. Her nipples ached with need but she understood that this was deliberate and part of her punishment.

“Bend belly down over the arm of the couch, Ruby.”

Ruby shook with a mixture of emotions as she moved to obey; she was mortified, embarrassed, saddened. Pride had led her to this. She thought she could interpret her Master’s commands to suit herself. She had indeed earned this punishment.

AJ stood to the right of her, his hand resting on the naked curve of her luscious bottom as she settled face down on the couch, ass propped high by the couch arm, her toes just touching the floor.

He unhooked her garters and fondled her, his big fingers stroking her ass, exploring the texture of her skin, delving into the heated crack. All of her attention riveted there where he fondled and caressed and invaded.

“Spread your ass for me.”

Heat rolled over Ruby as she complied. Anticipation, fright, shame combined to keep her heart tripping and stumbling in her breast. Remorse that she had brought them both to this kept her flushed with unnaturally bright color and on the verge of tears.

“Good girl,” AJ said quietly and she heard him dip his fingers in the bowl of water. Something wet, cold, and smooth touched her asshole and though she had been expecting it, she flinched nonetheless.

“Bear down.”

As the pressure increased, she bore down and the ginger plug slid easily inside her. It was smaller, cooler than the ass plug AJ usually used. Her anus clamped around the carved indentation and AJ held the plug there a moment, to be certain it was properly positioned.

“Ruby-mine, place your hands palms down on the cushion above your head.”

Ruby obeyed, utterly conscious of the cool firm ginger plug in her ass. Her long blonde hair glowed richly in the soft light and partially obscured the flaming curve of her cheek.

“Will there be a safeword, Ruby?” AJ’s voice was cool, dispassionate.

“No, Sir.” Ruby’s voice was muffled in the curve of her arm. She shivered, “There is no safeword during punishment.”

They had discussed this months ago. Then she had believed she would never find herself in this predicament, in her arrogance and pride she had believed that she would always please AJ.

“You are not to move your hands,” he told her firmly as he cupped her ass. “If you do, you will receive 5 additional strokes.”

“I understand.”

“You are to count each stroke. If you forget, you will be given 5 additional strokes for each miss. You are to thank me for each stroke. You will be given 5 additional strokes each time you forget. Do you understand?”

“Yes Sir.” She quivered.

“Your punishment is 30 strokes of the crop.”


“Yes, Ruby.”

“Thank you for this punishment I am about to receive.” Her breath hitched and her voice was thin, thready yet sincerity shone in her.

“Good girl.” AJ fondled her ass lovingly. “And baby-“

“Yes Sir?”

“With each stroke, you will give up your doubts, shame, and guilt and replace them with…”

“The pain, Master.” She finished for him when he deliberately trailed off. Her voice was thick with tears. Almost as an aside, she noticed that the ginger now glowed warmly in her ass.

“Ruby, I love you.”

AJ brought the crop down sharply on her ass.

Her whole body shuddered with the bite of the crop and she drew a hissing breath at the hot line of pain. It triggered her tears.

“One. Thank you, Sir.”

The crop whistled briefly and she heard the impact almost before she felt the stinging pain.

“Two. Thank you, Sir. “Three. Thank you, Sir. “Four. Thank you, Sir.”

Ruby closed her eyes as the heat built with each stroke. Sometimes AJ paused to stroke his palm over her soft skin. Sometimes he brought the crop down in quick succession. Her body vibrated with each blow, her breath caught in her throat but she kept her palms down as though glued to the cushion and she kept track of the strokes though her eyes blurred with a thick rain of tears. She needed this…expiation, this way to exchange a lasting guilt and shame for transitory pain.

At ten strokes, AJ paused a long moment.


A brief hesitation and then a hitched, “Ye-hess Sir?”

“You are doing beautifully. I love the way your ass jiggles with each stroke of the crop and the heat is delicious.” He traced a finger along one red welt and Ruby shivered. “Tell me about the ginger.”

“Burning heat,” she whispered.

He chuckled, removed his hands from her heated ass and resumed. He had placed the first ten strokes evenly over her ass. Now he began to vary both intensity and placement.

“Eleven. Tha-hank you, Sir.”

The next stroke landed precisely over the previous one and the pain of it strangled her voice in her throat.

“T..t..twelve. Thank y-hou, Sir.”

Heat. Burning Heat. When she inadvertently, instinctively tried to clench her buttocks the ginger flared white-hot and she relaxed her muscles with a hiss. Fighting the kiss of the crop resulted in a sharper pain. She forced herself to embrace it.

Ruby imagined that each stroke of the crop, as it lay briefly against her flesh, soaked up her doubts, shame, and guilt, and lifted them away even as her Master lifted the crop for a fresh stroke. Each heated brand became a cathartic agent, welcomed, needed, sought. She relaxed into each blow, letting her breath go in a long slow release.

“Twenty. Thank you, Sir.”

Ruby lay breathing deeply, her body soft and pliant beneath AJ’s hands as he paused again. Her ass hot and red, his palms a cool soothing caress.

“Ruby.” And then sharper, “Ruby.”

She drifted on sensation…on the heated sting of her ass, on the glowing heat of the ginger inside her. AJ gave her this pain as an avenue to grace, she thought gratefully. She felt hollowed out, cleansed, remade.


“Tell me about the ginger.”

“White hot, Sir.” She shifted her hips as she spoke. “May I move, please, Sir?”


The question stumped her. “Because I need to move, Sir. The ginger wants me to move.”

He chuckled softly “Stay still, lover. How many strokes are left?”

“Ten, Sir?”

“Correct. I am so proud of you, sweetheart. You may stop counting at 25.”

AJ stroked his palm over her glowing bottom in a loving caress. When he resumed her punishment, it seemed to Ruby that the pain had faded into the background and what the crop delivered now was pure heat. Purifying heat.

“Twenty-one. Thank you, Sir.”

He administered this punishment out of his love for her, she realized dreamily, as the blows flowed one into the other. Her hips lifted slightly with each stroke…an unconscious welcoming gesture. Her voice, while unwavering, held a soft otherworldly quality.

“Twenty-five. Thank you, Sir.”

“Tell me about the ginger, darling girl.”

“White heat,” she whispered, “It makes me want to move. Please sir, let me move.”

“Show me how you want to move.”

Ruby rolled her hips into the couch arm in a languid imitation of sex. AJ let his breath go in an explosive rush that was not -–quite – a triumphant laugh.

“Soon,” he said. “You may move when I fuck you, not before.” He brought the crop down again.

She gave herself completely to the crop, to the heat, to the man who mastered her with skill and thought and love. Ruby slid farther into sub-space and floated there.

She came to herself slowly, a piece at a time: aware first that her cheek rested on nubby-rough carpet. Her wrists were cuffed and she was face down on the padded carpeted bench. Her legs were spread wide and AJ stood between them.

She felt the heat of his legs against her thighs, the hair-roughened caress of them as they stroked against her. On-off, on-off, heat-cool rush of air. There was sound too, she realized…a liquid slide and muffled thump, the sound of flesh on flesh. Her body moved rhythmically. The friction-full stroking of hot cock into her body, into her pussy, gradually matched the sound of it.

Her ass was afire. AJ’s hands curled over her hips tightly, holding her just so, pulling her just so, just so…

“Oh,” she said.

“The heat is delicious, love.” AJ crooned, pressing his groin against the flaming curve of her ass.

An electric jolt surged through her as he buried his cock deeper inside her and her hips lifted in welcome.

“Oh, god.” She said on a long moaning breath.

“I claim you,” he said, fucking her so strongly that her body slid against the rough weave of the carpet until halted by the restraints. “You belong to me.”

“Yours,” she sighed, eyes closed in rapture. “I submit. I submit, always.”

His cock took her in long hard strokes, faster and faster, driving the heat up inside her so that Ruby felt as though she were melting from her pussy outward. AJ, her lover and Master, melded them into one entity. Erasing boundaries, erasing limits he took her over, he took them both to completion.

“Cum now, Ruby.” He said and Ruby came so hard that her pussy locked tight as her body shuddered under wave after wave of bliss. Her cheeks tingled with it.

“God, that’s it.” AJ moaned, pressing his chest to her back. “Oh baby, I love the feel of you when you cum on my cock.”

He bit her on the back of her neck and her body bucked as another sharper wave of pleasure surged through her. He kept fucking her through her climax, his hips slapping against her burning ass, his cock a hot flame.

“Mine,” he said minutes? hours? later and then he thrust deep and came, his moans of pleasure music to her ears.

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