by Trent Evans
“I can’t… Mistress.”
Her smile was cool, her eyes glinting. “You can, because your Mistress told you to do it.” She leaned forward, elbows on the table, her fingers laced at her elbows, her breasts pressed together in the snug top. My cock was already stirring at the sight, and I was very grateful the table at least sheltered it from view.
“I was wrong — I told you that. Why make me look at them?”
Darynn sighed, walking back toward the oven. “I told you he wouldn’t do it. He’s not ready yet.”
Anna flicked a pointed glance at her companion. “We’re not done, yet.” Anna’s feline eyes fixed upon me once more. “Now, open the envelope and do what you’re told. Your only job here for the foreseeable future is to do as you’re told, whatever it is. Don’t do it, and it’s back in your little hole you go, more pain, more misery, more isolation. Is that what you want?”
“No.”
My heart was already jackhammering at the thought of spending even one more minute in that cell. The sweetness of being anywhere but there was something I didn’t even know how to express in words. Perhaps it was the feeling a prisoner had that first moment he walked out the front gate of prison on the day of his release.
“That’s ‘No, Mistress.’ If I have to remind you again, you’re going to be punished.” Anna’s nostrils flared for a moment. “Now, open that envelope, or I’m going to start thinking you don’t want to do as you’re told.”
I shook my head slowly, knowing I would pay dearly for it. I wanted to plead with her, to beg her not to make me do it. Instead, I stayed silent — and had no idea why. Perhaps it was the last dying vestiges of my humanity, the fading memory of what it meant to be in control of even the smallest aspect of my life.
The life I already knew inside was dead and gone.
“I see,” Anna said. She looked over at Darynn. “Bring me the strap, will you? The thick one with the split.”
“Gladly.”
Darynn was gone with a whisper of air against my naked — and suddenly sweating — back.
“Please… I don’t want to anger you, but I can’t look at those. Please.”
I didn’t know why I said it. I feared the strap, the pain I knew was coming — but I feared confronting my actions even more. Was I really choosing agony over facing the consequences of my own stupid decisions?
“This isn’t about what you want, Quinton.” Anna stood, the tips of her fingers posed on the table top as she leaned over it slightly, looming over me. “Your existence, from this point forward, is about doing what I want. Eventually, you might understand that — given enough incentive.” She walked around the table toward me, the upper curves of her breasts stirring appealingly as she moved. “How much pain you need to ensure before that understanding is reached is entirely up to you.”
She sat on the table, dangling one leg down toward the floor, lacing her fingers around her knee. “I’d much rather begin your training today than deal with this ridiculous — and completely futile — defiance. But as I said, you always will have a choice.”
My cock was up fully, though it should have been terrified at what I knew was about to happen. Her proximity, her scent, the way those luscious breasts moved — that seemed to be the only thing my heedless penis seemed to care about, not the fact I was about to get my ass beat within an inch of my life.
“There we go,” Anna said, taking the chocolate-colored length of leather from Darynn.
“You need me to prepare him?” Darynn said it from behind me. She was very close indeed.
“Let’s see if he wants to make things even worse for himself.” Anna looked down at me. “Now, I want you to get up and lay yourself over the table, hips against the edge. You’ll grasp the far edge with those hands, and you won’t let go until I tell you — no matter what. Do you understand?”
I nodded, swallowing, my mouth hopelessly dry.
“Then get into position, my stubborn boy.” Anna’s lips quirked into something resembling a sly smile.
That she was enjoying this was clear — but there was almost an element of playfulness in her expression. Somehow, that knowledge that she wasn’t completely enraged with me, despite my refusal, allowed me the courage to rise.
Darynn’s chuckle made me want to sit right back down. “His cock is practically exploding. Must like pain.”
“I—”
“You keep your mouth shut,” Anna said, touching my chest with the leather. Though she did glance down at my shameful display of arousal, she jerked her head toward the table. “Lay over it before I add strokes for delaying.”
I did, somehow grateful for at least being able to not have to look at either woman, even as I assumed the extremely vulnerable position. The wood was frigid against my sweaty skin, and I squeezed the far edge of the table frantically, trying to concentrate on simply holding on, hoping it might distract me from the pain about to be laid across my cringing flesh.
The leather touched my ass, rubbing circles into it. “We’re not starting until you unclench those cheeks. This is one of your rules — and it will always apply. You will always, always, keep that ass loose, soft. The punishment does its best work when you accept it fully. Willingly.”
Oh Jesus, I can’t do this!
“It hurts too much. I don’t think… I can.”
“Yes, you can — and you will. I want the pain to sink in fully, boy.” The leather snapped at me. “Now, do as you’re told.”
Just do it, dammit.
The room was silent as they waited for me to fully cooperate with my debasement. I pressed my hot, blushing cheek to the table, shutting my eyes, waiting for the inevitable.
When it came, the stroke felt like it drove my hips into the wood, the sound cracking through the air as the dull burn sank into my buttocks. It was a different pain from the cane or the crop, a sort of tearing burn that seemed - -in the first instant — easier to endure, but instantly began to intensify. The sound of the stroke was almost as shocking as the pain.
Another blow fell, this time high up toward the beginning of the cleft of my buttocks, and I grunted, the pain digging in much more, clawing into my flesh. I couldn’t help but wag my hips, wanting desperately — already — to reach back and rub the pain away.
“I can hold him, if you want.” Darynn’s voice was pure avaricious anticipation.
“I want him to stay down for this. If we can get him to follow directions when he’s getting his little ass beat, maybe there’s some hope for him after all.”
I wasn’t quite able to suppress an angry sound from slipping from my lips.
The strap slammed into the backs of my thighs, fire flaring across my flesh, and I cried out. “I don’t believe I asked for any editorial from you.” Anna said, her voice calm, almost soft. “I was about to tell Darynn she could go outside and take a break. But since you decided to offer your little editorial, I’m going to have her stay here and watch your disobedient bottom turn a nice shade of red.” The leather rested on my cringing buttocks, and my breath hitched in my chest. “Which do you think is better, boy? Resting quietly in position, waiting for your richly deserved punishment — or running that smart mouth?”
I didn’t say anything, my eyes closed so tightly, they hurt. Every muscle in my body was tense, my breath quick and shallow.
“I expect an answer to any question I pose to you, boy.” The strap landed across my thighs again, this time almost behind my knees, the pain blooming bright. I stamped my feet against the floor, but managed to stay still.
“I’m sorry!” The words humiliated me even more than my aching ass, my exposed position.
The edge of the strap prodded my hanging scrotum. “Get those legs together. If I want to see those big balls swinging around, I’ll tell you.”
“I think he likes showing them to you,” Darynn said, the smile plain in her voice. “He may be a piece of shit, but he’s got a nice set of balls on him.”
“Nice or not”—she
slapped my ass with the strap almost peevishly—“I don’t want him waving them in my face unless I tell him to.”
“Bad boy,” Darynn mocked in a sing-song tone.
I slammed my thighs shut instantly, the shame so overwhelming I thought I’d drown in it. I thought I’d experienced humiliation in my cell before.
This made that seem like child’s play.
So why is your cock still hard as a rock? What the fuck does that say, Quinton?
I hoped they couldn’t see that, but I was certain they could see everything, that knowledge only making my embarrassment worse.
“Ready?” Anna tapped the strap against my ass lightly, as if to check her aim.
“Yes.” It was a lie.
The strap caught me diagonally across my left buttock, the tip wrapping up over my hip and biting there fiercely, my groan stifled against my arm.
“Try again.”
“Yes, Mistress!”
Rather than respond, the strap began falling remorselessly, a storm of heat and pain across every inch of my ass. Like a metronome, another stroke would land every second or two. I lost count after twenty, the pain building to a pulsing, agonizing heat, punctuated by the searing, tearing pain of the strap biting in yet harder, the tip catching me low on the thigh or wrapping around my hip. Despite my misery, I was glad she’d had me close my legs, the thought of that tip striking my scrotum enough to have my stomach roiling.
“Loosen that bottom, boy.” The tip of the strap prodded my seething buttock.
I managed to obey her, my breathing coming in great gusts, my sweat dripping from my brow to pool on the table.
“Oh Christ,” I ground out as another hard stripe slammed into me, the tip clawing into the tender flesh just above my knee.
“Good shot,” Darynn said, relish in her tone. “He’s gonna feel that one for a few days.”
A hand brushed the outside curve of my ass, a hard, sharp nail prodding my aching flesh in spots. “I want to see if I can link these wheals. I’d like a nice thick band low across here. Should make sitting unpleasant for him for a bit.”
I hissed as that nail scratched inflamed, welted skin.
“Nice and red, but no bruising yet. I say go for it.” Darynn laughed softly. “Starting to see the error of your ways, Quinton? Maybe next time your Mistress tells you to do something you’ll remember this little ass whipping. Silly boy.”
I clamped my tongue painfully between my teeth as Anna strapped me three times, rapidly, the leather landing upon the same spot. I rose up onto my elbows at the third one, my head thrown back as I yelled out my anguish.
“Settle down, boy,” Anna said, warmth in her voice rather than the anger I expected. A hand touched my shoulder. “Back down now. You’re not done… come on. There you go.” The hand touched my sweat-soaked hair, the fingers stroking through the locks. “Be a good boy for me and stay still for your strapping.”
I almost said the words, the response becoming uncomfortably natural, but instead I bit into my tongue once more, the harsh leather cracking across my ass over and over. Rapid fire, the strokes came, until my groans were continuous and I thrashed against the table, my fingers holding so tight to the edge that they felt as if I might drill them into the wood itself.
Then it was over, and I laid there, my chest heaving, a bead of stinging sweat running into the corner of my eye, my ass a fiery mass of anguish.
Anna stood behind me, her hands caressing and kneading my buttocks. “There’s a good boy. I know that hurt, but it’s the only thing that gets through to you, isn’t it? Besides, I don’t think you have any idea how cute this little ass looks all red and bruised.”
“It’s good work,” Darynn sniffed. “But I think you’re still going way too easy on him.”
Easy! What the fuck is she talking about?
My ass hurt so bad it felt like it might just fall off. And yet, my cock was still raging hard.
“Now, up with you,” Anna said, her hands pulling at my shoulders. “You’ll take your seat again, and we’ll see if you still feel like defying me.”
I rose, my ass feeling heavy, congested, throbbing.
“His cock is still up.” Darynn strolled back into the kitchen. “Very interesting.”
Still behind me, Anna clamped a hand upon my shoulder, a signal to be still. Her other hand eased across my hip and took hold of my cock. She squeezed it firmly, and I took my lower lip between my teeth. It would take one stroke, maybe two, and I knew I’d go off like a fucking fountain.
Please, God.
“This wants to come so badly, doesn’t it?” She pumped me slowly, squeezing tight the whole time, the harsh grip keeping my orgasm just out of reach. “Do you think you deserve to come, stubborn boy?”
“I know you’re not going to let me.”
That seemed to set her back on her heels — but only for a moment. With a last parting squeeze upon the head of my cock, she slapped my hip.
“You’re right, I’m not. Now, have a seat. I want your mind on something other than your penis for a change.”
I bitterly swallowed down my retort, even as I knew the torture she was intentionally inflicting upon me was likely nowhere near at an end. I didn’t know when she’d let me come, but I knew it wasn’t going to be anytime soon. My balls throbbed, feeling heavy between my thighs as I pressed my welted ass against the cold, hard wood of the seat.
I drew a harsh breath through gritted teeth as I tried to find a position that didn’t reawaken the stinging ache of the stripes the strap had left behind.
“Sitting a little gingerly, it would seem,” Darynn said from the kitchen.
There were several windows that surrounded the dining area of the kitchen on three sides, and the light that poured through them was even brighter now. All the easier to see what lurked inside the manila envelope Anna’s long fingernail tapped.
Don’t fucking do it.
But I knew that this time, the choice was theoretical only. There was no longer any way to avoid it.
“Time to open it, Quinton.” She laid the hardened leather strap on the table next to the envelope. “Or you’ll be paying the piper again.”
Chapter 15
She still wasn’t certain he’d do it — and she wasn’t certain if she wanted him to do it.
Her sex was absolutely soaked as she replayed the way the leather strap worked over those muscled buttocks, the way his cries had been bit off with each merciless stroke of leather across strap-scorched flesh, that masculine pride dying to prevent that last humiliation, keeping him from begging for mercy they both knew she had no intention of granting.
No, she’d have been perfectly satisfied to bend him over that table once more, and take that strap once again to her stubborn boy’s already bruised bottom.
He’s not yours, Anna.
But wasn’t he? In his mind, she could tell he’d already begun to make peace with it, to accept the reality she’d imposed upon him. She’d reduced his world, stripped it down every bit as much as she’d stripped his body.
His world was only her now. Obedience. Pleasing her.
Perhaps he was still fighting it — and maybe always would — but she’d expect nothing else. And if she were honest with herself, she wouldn’t want it any other way. There was a satisfaction in conquering a recalcitrant male, in showing him the truth, opening his eyes to the reality that he was nowhere near as strong as he thought.
And that by no means were women the “weaker” sex.
She subtly shifted her thighs, her sodden panties sticking uncomfortably to the lips of her pussy. She’d need to change them soon.
But that would wait. What was about to happen was far more important — for all of them.
He looked at her finally, his blue eyes almost flat, a lost note to them. Was it resignation, a surrender to something he knew he could no longer fight? Or fear?
“I don’t know… why you’re making me do this.”
She touched the strap, and
his eyes unerringly followed the movement of her fingers. “You don’t have to know. You just have to do. You just have to obey me.”
At the moment when she suspected his nerve would break, when he’d flee from the truth yet again, his trembling fingers — his hands still bound together — unwound the tiny little string that held the envelope closed.
He upended the envelope, the pictures scattering across the varnished wood.
“Now, look at them,” Anna murmured. “And tell me what you feel.”
His fingers gently spread the photos apart, his face paling as he reviewed each one. He closed his eyes tight when his fingers turned over the image of Genna’s bleeding wheals. But he pressed on, finally looking upon them again for a long moment. His throat worked repeatedly as he gazed upon the evidence of his wrongdoing, of his stupidity, of his cruelty.
It was in there though, perhaps stronger than ever, as she looked upon him. That scared little boy she got the tantalizing glimpse of in that interrogation room all those many days ago. That little boy was the real reason she’d agreed to take the contract, though she’d never have admitted to it at the time.
That boy could be rescued, even if the man he’d become was irredeemable.
“Tell me, Quinton. There’s no hiding here — from anything.” She tapped the strap with the tip of her finger. “No hiding from me.”
“I wish I’d have known.”
She didn’t have any idea what he meant, but she stayed very still, very quiet. Maybe he was sorting it out for the first time. Right there, as he sat there.
“That’s wrong though — I think I did know. Somehow, even though I enjoyed it. Even when I wanted more.” He dropped his head for a second, and she thought he might actually begin to weep. She hoped he didn’t though; if her pussy got any wetter, it was going to start soaking her pant leg. Even so, she’d have welcomed his tears — and not just because they’d make her clit hard, to just because it made her want to devour him. No, those tears — if and when they ever really came — would be a concrete sign that there was hope for Quinton Trask, that that little boy somewhere inside did indeed have a chance. Tears would be a sign of what he should have been feeling from the first moment he brutalized those women.