by Trent Evans
“You know you’re going to have to be punished. Care to tell me why?”
“Don’t you think I’ve maybe had enough for the time being?” My jaw ached, but I knew it was my pride talking more than any actual injury.
Anna crouched down before me, taking my sore chin between finger and thumb. “Your smart-assed tongue isn’t doing you any favors right now, boy. Wanna try again?”
I kept silent, knowing better than to say anything.
“No? I thought so.” She hooked a finger in one of the steel rings that adorned my collar, yanking it. “You sat here and cussed at Brayden — when you should’ve been apologizing to him too. Why did you do that?”
Just the thought of Brayden had me seething all over again. But why?
“Shock… I guess. He did screw me over… but I don’t think that’s what made me say it. I don’t know why I said it.”
It was a lie. It was my pride talking. The pride I’d thought Anna had extinguished altogether, the same pride that too often had clouded my vision, blinded me to the difference between right and wrong.
Was what he’d done really that wrong? I really didn’t think so now. He’d done the right thing… something I didn’t know how to do. Not then, anyway.
Not the old me.
Yes, he’d betrayed me, and it did sting. In the past, I’d have been murderously enraged. Now? What did I have left to be pissed about?
That life was dead and buried. What Brayden had been in relation to me was ancient history now, betrayal or not.
It burned within me, that I would still be entertaining thoughts this selfish, even now, after everything that had happened.
“Give me one reason not to whip your fucking ass right now, Quinton.” Her eyes were stormy, her mouth tight, even cruel. “I saw that old you, that selfishness when you cursed at him — and I didn’t like it. Do you have anything to say for yourself?”
“No, Mistress. You’re right about that.”
A part of me felt the justness of it, the need to do something, anything, to help purge myself of the guilt, the self-loathing, the sorrow that threatened to overwhelm me at that moment. I’d been presented a chance, a precious opportunity to start doing things the right way. To give myself some hope that somewhere inside me was a person who could look himself in the mirror.
Someone who could truthfully call himself a good man.
And I’d failed. Worse, I’d failed her.
I looked up at my Mistress then, my body already beginning to tremble, knowing that what was to come was going to be terrible indeed. “It was the old pride, the old me. And I deserve to be punished for it.”
* * *
She led him down the hall with a thumb hooked in one of the rings at his collar. It was the one drawback to his little cage — she couldn’t lead him around by his rampant erection anymore.
It was a drawback she was more than prepared to live with.
He didn’t resist at all as she led him to the bed.
She’d laid out the wedge and the under-mattress restraints for him before coming back to retrieve her captive from the living room.
The level of anger she felt at his response to Brayden was surprising to her. She really did want him to behave well, to face his meeting with the two people with humility, with dignity. He hadn’t been able to resist his old habits, if only for a moment.
You think that’s all this is about? Why do you keep kidding yourself?
Ignoring it, she snapped her fingers. “Over the pillow. Don’t make a fucking sound. Hands and feet toward the corners of the mattress.”
Was she angry because the old Quinton reared his selfish, callous head? Or was it because her vaunted training hadn’t yet broken him of his old ways.
There was more to it though… and it brought her back to that day in the interrogation room, Quinton’s father watching them through the one-way glass. Watching as his son cursed her with every foul word she’d ever heard in her life, watched as Quinton’s face turned red with rage. Even then, in the depths of his blue eyes, she saw it.
The scared boy.
What if the reason she was so angry now was because of what she’d seen for just an instant as Quinton stared up at Brayden. She’d seen it again.
That scared little boy.
It was his bluster, his anger that tried to hide it. At that moment of betrayal, Quinton had realized it was a man who was part of his inner circle who was the one responsible for beginning the process of destroying the life Quinton thought he knew, thought he loved.
It was something she’d so rarely seen in her charge, and something she craved, desired — and coveted — more than anything else about it.
Vulnerability.
As sweet as it was to see it in him — to know he was even capable of it — was one thing. But what his vulnerability engendered within her was something else entirely.
At first, it had been a distant echo, a hint, a whisper. But it had been growing. And in the past few days, its presence had been the elephant in the room when it came to the dynamic between she and her slave. Its presence was undeniable now.
It was perhaps the most dangerous thing she could possibly feel in their current situation.
Affection.
What was she going to do about it? What could she do about it?
Ignoring it was her go-to solution. It had happened only once before, and she’d spent months successfully denying it then. But eventually, it had worn her down. Eventually, she could resist its pull no longer.
Yes, it had happened once before — with Greg.
You’re in trouble here.
Wordlessly, her stubborn slave obeyed her commands, draping himself over the wedge pillow, his gorgeous ass high, his head low. He didn’t bury his face in the blankets though. This time, he stared straight ahead. This time, he wasn’t trying to hide from what was coming.
Good.
He said nothing as she cinched the cuffs around his wrists, and she bound his ankles tight. Hauling them toward each corner, he was stretched taut before she returned to the implements laid out on the mattress beside him. She’d wanted him to see them as he climbed up into position, to know what might be painting agony upon his helpless flesh in the next few minutes.
He’d shown not even the slightest reaction.
Plucking the heavy wooden paddle from the bed, she stood behind him, clasping her arms under her breasts. “Somehow, you’ve gone off track, boy. My job is to get you back on track.” She tapped the wood against the lower curve of his ass, the heavy paddle spanning both cheeks. “No matter how much I have to hurt you to do it.”
Her panties were already sticking to her pussy at the thought of what was about to come. With his legs so widely spread, his genitals were clearly visible between his legs, looking so vulnerable, his helpless exposure shaming him well.
It only fired her sadistic arousal higher.
The first crack of the wood drew a satisfying grunt from the stoic man, but nothing else, his flesh rippling with the hard impact. Laying the wood just below the rapidly darkening mark, she snapped it home again. The pain made his buttocks flex and squeeze, then he was still, knowing she expected strict obedience during any punishment, no matter how agonizing.
“Good boy,” she murmured, lining up the third stroke. Smacking home with a loud splat, the merciless implement flattened his buttocks, his flesh bouncing back to the sound of his sharp intake of breath. The strong muscles of his lower back stood rigid as he dealt with the pain, his ass quivering.
A fourth and fifth blow ensured his entire backside was now covered in pink and red bars of woe. His hips wagged side to side on the sixth stroke, only stopping when she barked a warning to him to stay still.
“What are you being punished for, slave?”
“For… cursing. Mistress.”
“Wrong.” She slammed the paddle home against the lowest curve of his cheeks, and he bit off a cry, his thighs beginning to quiver now. “You’re being punished bec
ause you failed me. The old you — the vile, hateful, selfish you — is gone. We’ve worked hard to drive him away. And so help me, if I have to whip your ass bloody, Quinton Trask, that you is never — ever — coming back.”
The words poured forth almost of their own volition, as if they’d been hiding in her subconscious, waiting for the perfect moment to dash forth, to break free and proclaim their truths to the world.
To the both of them.
Five more hard, merciless blows of the wood left him crying out at each one, his stoicism breaking under the paddle’s irresistible power, the pain too much for even the most hardened soul.
He was writhing continuously over his pillow when she set down the paddle, breathing hard.
Caressing his agonized, swelling flesh with her hand, she loved the heat she felt there, his pain, his humiliation making her clit throb, her sex a molten furnace between her thighs.
His entire ass fairly glowed red. A good base for what came next.
But first, he needed something else. Another lesson in humility.
Flipping open the top of the lube bottle, she coated the thick, shiny steel plug, slicking the lube all around it with her fingers, then setting it aside. Using her free hand, she spread his cheeks further apart, his position already partially exposing his vulnerable hole to whatever she decided to do to it. He jerked as she circled her fingertips around his vulnerable opening, leaving it glistening.
“I want you to relax for this, boy. This is the biggest plug you’ve had yet. It’s not going to be easy. I need to get you nice and primed for it. Relax now, just Mistress touching you.”
Her finger slipped in easily, and she plunged it deep, all the way to the last knuckle, loving the way he shivered as she wiggled it inside him.
“You like that, don’t you? Is your little cock aching against its cage? Tell me.”
“Yes, Mistress,” he whispered.
It was a pleasure she savored showing males, that dark forbidden shameful pleasure of being penetrated deeply, of having that most private of places invaded, their Mistress heedless of their embarrassment, their reluctance only arousing her still more.
Making these recalcitrant males face these shattering discoveries was perhaps one of the sweetest parts of bending them to her will. A quiet pleasure she still savored, replayed in her mind, long after the act itself was done.
Taking up a firm thrusting, the deep, sure strokes stoking the arousal of both of them, she soon presented a second finger, each pass of her knuckles against that secret spot within him making him gasp and shudder. The knowledge that the steel prison around his cock prevented even partial erection, only further tormenting him, made her grin. There was a unique sadistic pleasure in denying him, in simply taking his penis completely out of the equation until she required its involvement again. Nothing else so focused a male slave’s mind, as the knowledge that his Mistress held such a visceral, primitive power over him. Nothing else humbled him so — and nothing else was as effective as encouraging him to be as obedient and docile a slave as he possibly could be. The faint, tiny hope that his penis might eventually be released from its exile was the most powerful incentive on this Earth for a desperate male submissive, even as he knew that it was a fool’s hope. She’d keep him locked up, far past the point he thought he could endure.
But he would endure it nonetheless — because it was what she’d decreed for him.
“One more now,” she murmured, folding her three fingers into a tight cone and pressing them slowly inside. He’d never taken that many before, but he did, even as his body shuddered, letting out a long, lost groan as she slipped fully inside him.
“That’s my good boy,” she said, patting his ass as she took up a gentle plunge and retreat inside his tight opening. After a minute or two, when he’d relaxed around her, she pulled them free, loving the way his anus gaped wide for a moment. It pulled closed again when she tapped it with a gleaming fingertip.
She recharged the steel with more of the cold gel, then presented it to his ass. “Push now. You’re ready for this.”
His hole visibly slackened, and she was able to advance the tip of the steel inside.
“Good boy. More now, push back. Open… open.”
Then she met more resistance, and he groaned. “Too big…”
“No, it’s not. Relax and push.” She fondled his big balls in her palm, so blatantly presented by the cage’s ring holding them tight. “This plug is going inside this ass, no matter how long we need to take to do it.”
He managed to open further, and she took advantage of it, pushing still more of the hard steel inside him. His anus was already spread wider than even her strap-on had forced it — and he still had a fair bit of the plug to take, including the very widest part.
“Bear down on it, boy.”
“I can’t!” He bit out, his voice tight.
“You can and you will.”
She pressed still more, and he shuddered, the steel advancing a tiny bit more, Quinton taking several deep breaths. She relented, then applied more pressure, fondling his balls as she did, hoping it would distract him from the relentless plug insisting upon entry. After two more tries, she pulled the plug back, setting it down on the cloth she’d set aside for this endeavor.
“You’re not cooperating, boy. Let’s see if we can give you a little incentive to obey your Mistress.”
Taking up the small rubber whip, she opened him up again, taking aim. The tip snapped down just above his anus with a wet smack, Quinton’s entire body going rigid, and drawing a confused sound from him.
“You will open your ass for your Mistress, boy. Or you’ll be punished for disobedience.”
Three more times she whipped into his cleft, the tip of the whip landing directly on his asshole for the last two strokes, drawing a harsh cry, and hissed curses from the bound male.
She menaced the helplessly vulnerable scrotum with the tip of the rubber whip. “Feel like doing what you’re told now, or do you need more encouragement?”
Her pussy was a flowing river as she watched the marks upon his anus swell and redden. They would be distinctly uncomfortable tomorrow morning.
“No! Try it — I’ll try again. Please don’t, Mistress! I’m sorry!”
“That’s better.”
The plug once more presented to his ass, he pressed back upon it, breathing out slowly, his anus swallowing more and more of it as she pushed.
“That’s it, slave. Take that plug.”
He moaned, his thighs going taut as she met more resistance.
“I know it’s uncomfortable, but you’ve got to learn to take this. Your Mistress wants this. You want to please me, don’t you?”
He said nothing, gasping as she pushed the plug still further into him.
“Don’t you?”
“Yes… Mistress. Oh, fuck, it’s—!”
“Almost there. Just a little more.” He was stretching dramatically now, just on the edge of what she thought he could take before real pain would be involved. “Almost…”
He let out a harsh exhale as the widest part disappeared, the hard stretched anus clamping down around the narrow neck of the plug. She pressed a little further, making him shake and protest, until only the smooth steel O of the plug’s pull ring was visible, protruding from his opening.
“There! I knew you could take it.” She patted his bottom. “Squeeze gently on it now. Get used to the stretch.”
“It aches…”
“I know it does. It’s supposed to. Give it a minute and it will fade a little. Be strong!”
Taking up the cane, she stood at his side, tapping the rattan against the crease at thigh and buttock.
He turned his head, his eyes wide, desperate. “Jesus Christ! Please!”
“Your punishment isn’t done yet, boy.” She scowled at him. “You’ll face forward and take your punishment quietly, or we’ll be adding a gag and ten more with the paddle. Would you like that instead?”
His hea
d snapped forward, his cheeks blushing bright. “No… Mistress,” he ground out.
“Then be a good boy and take your punishment quietly.”
Taking careful aim, she kept the cane pressed to his flesh, drawing out that moment of dread, noting with pleasure the way he seemed to be holding his breath, the utter stillness of his body as he awaited still more agonizing discipline from his implacable, cruel Mistress.
Slicing down the first stripe, hard, he hissed, his bottom trying to clench, his position and the thick plug preventing his buttocks from doing much more than tremble and shake.
The mark immediately began to fill in, and she laid down another, even stiffer this time, approximately two inches below that, drawing a gasp from him, the tender flesh of his upper thighs far more sensitive than his ass. Then she striped him quickly, using those two swelling welts as the boundary within which to lay down his punishment.
Within a minute he was yelling and pleading with each stroke, his ass waving frantically over the cushion. She snapped the cane across the middle of his cheeks, the rattan impacting against the steel pull ring, and he howled, the vibration no doubt traveling down the plug and into his tender rectum.
“Keep that ass still, or you’ll get another just like that. We’re almost done, boy.”
Her nipples ached, her mouth dry, her pussy seeming to have concentrated every ounce of liquid in her body between her impossibly slippery, swollen labia. Her clit throbbed angrily, fair screaming at her to provide it relief.
Aiming carefully, despite her increasingly desperate arousal, she laid down three more wickedly harsh cane strokes within that empurpled band of anguish lacing the crease of his buttocks and thighs. He screamed at the last one, his lips babbling desperate gibberish, his speech faculties seeming to be short-circuited by the agony of the cane’s aftermath. She bent close, touching him, feeling the swollen, inflamed, scorched flesh. She’d whipped the skin raw in places, a pair of the marks oozing a tiny bit of red.
It was one of the hardest canings she’d ever administered, and part of her was shocked she’d had the fortitude to go through with it.