by Trent Evans
“Ready for more then?”
Oh, shit!
I didn’t know what I was supposed to say. Was I supposed to ask for more even as I knew I was already at the very limits of what I could tolerate? Or was this some sort of test of obedience? Maybe if I said yes, she’d spare me, my submission to her confirmed?
I nodded my head.
“Good. I thought so.”
Then the wood pressed to my buttocks again.
Oh, fuck! Please God, no!
The paddle proceeded to drag me down to the darkest depths of hell, the pain worse than anything she’d inflicted to date. My ass wobbled and shook, the wood painting wide swathes of torment across my flesh until I was screaming against my gag. My cheeks were wet though I didn’t know if it was with tears or sweat, my hips writhing. I’d never felt pain like that, not ever, the intensity of it shocking, sickening.
Then something even worse happened.
She caressed my back.
As I pulled at the ropes holding my arms helplessly at my back, she stroked my sweaty, trembling flesh as I breathed like a bellows against my gag, my blindfold soaked.
“It’s okay, just breathe through it now. It’s okay.”
I hated her voice. I needed her voice.
The gag was a blessing, for I feared I might beg her, tell her I was sorry for everything, for anything, if it would only spare me more. Overlaid upon all of that though was something that both shocked and infuriated me deep down inside.
Justice.
I’d deserved this — and more. The pictures of Genna flashed through my mind. I remembered how aroused I’d been handing her over to Brayden yet again to be unharnessed from the trap. Handing her over to smooth the healing cream over her wheals, to soothe her back to normal, to dry the tears that themselves had made my cock hard.
The same cock that had gone soft again under the torture of the paddle.
You deserve more than this, you fucking asshole.
I hated it, hated the truth, the depth of self-loathing I felt at the silent pronouncement.
And yet, somehow, in a twisted, fucked-up sense, I felt gratitude too. She’d shown me. Yes, it had taken my abject degradation, agonizing pain — even the loss of my humanity.
But I could see it now, what I’d become — and what I hoped I might be.
Would she show me that too? Would she help me become someone I didn’t hate? Someone I didn’t feel ashamed to be?
It was insanity — at some level, I knew that. It was likely the Stockholm talking at that point. I was beyond caring. I was beyond feeling sorry for myself. I was at the pure, lowest point a human being could be. I was existing, breathing, hearing, feeling.
Hurting.
I was only sensation then, only experience, merely a living thing. Expecting nothing. Hoping for nothing.
I am nothing.
“Quinton? Can you hear me?” Her voice was like a strong hand reaching down from the darkness descending upon me, my last hope of salvation from the yawning, terrifying void opening up to consume me. “Come back to me, stubborn boy.”
I mumbled something to her, but my powers of speech had apparently fled me.
“You’re okay. I’m here.” She kissed my temple, her hands stroking my shoulders gently. “You’re okay now.”
Slowly, my frantic breathing eased, Anna’s cooing words and soft touch soothing me, bringing me back down. Restoring me.
“Almost lost you there,” she whispered, kissing my ear. “But we’re not quite done, are we?”
My body began to shake, my voice helplessly pleading its nonsense against the remorseless leather of my gag. If only she’d free my mouth, I’d tell her anything she wanted to hear. I’d confess all I’d done wrong, confess how awful I’d been.
Confess that she was the only hope I had left.
But it was at that moment that the final truth revealed itself.
We both already knew she was my final hope.
I’d finally found what it was she’d been trying to show me. It was what I’d been… and how that person was now dead and gone. I’d had to walk through the fire, to burn away the twisted hate, to purge the selfishness, the arrogance.
And left only me.
She’d discovered me. Only this one, humble man.
I can do this. I will do this.
More than anything else in my pitiful existence, I wanted to find out who this man really was.
Chapter 24
He laid upon the mattress, growing so still that she’d thought he’d slipped off to sleep.
The man had been delirious after his paddling, his blindfold soaked with tears, snot running down his face, his cheeks flushed, sweaty hair matted to his skull. She’d put him through the worst trial yet, and was pleased to find he’d had the strength to endure.
Touching him… it held a strange power now, as if they both knew how much he needed her gentleness, especially after she’d tortured him so.
She stood up, leaving him be, his naked, silent submission finally laid bare for her. It was time to do what they both knew was coming, what she knew he’d need to truly understand his new position in life, what she’d made of him out of the ashes of Quinton Trask.
It was selfish of her, but it was time to revel in selfishness. Her throbbing pussy wouldn’t let her consider anything but.
Stripping herself entirely except for her harness and her heels, she fastened the dildo in place. It was a long, broad length of black, the surface smooth. She preferred the phalluses that were anatomically accurate — the flared head and veined shaft added a delicious extra bit of humiliation to stubborn male submissives — but for his first time, the one she’d chosen would do nicely.
She popped open the tube of lubricant, and he stirred, his head moving slightly at the sound of her fist coursing up and down the length of the phallus.
“Yes, that’s right. It’s time, boy. I’ve waited long enough before taking this ass.” She pressed the back of her hand against the crimson, deeply bruised ass. “And the wait is over — for both of us.”
Placing her palms on both his cheeks, he hissed. She yanked them wide, his cringing, tight little hole blatantly exposed. She smeared a glistening slick of lube around the dark opening, testing it with a fingertip.
“I want you to open wide. This is happening, no matter what you think you want — or don’t want. Before you leave this room, you’re taking every inch of me. It won’t be easy. You don’t want it to be easy.” She slipped a finger inside his bottom. “Remember what I told you, Quinton. Never easy.”
He gave her a gag-muffled groan in response. Thankfully, he decided to comply, his anus relaxing.
“Good boy, try not to squeeze. Just let this happen — that’s good.”
Waiting until she was able to get two digits inside, she thrust them deep over and over, until she thought he was ready. His hips began to push back against her as she pressed deep one last time, holding them there, her knuckles hard against the inner curves of his buttocks, scissoring her fingers open inside his body, stretching him just a tiny bit. Though he tensed for a moment, he didn’t protest, his ass cheek remaining relaxed under her palm.
She removed her fingers, and he shuddered. “It’s time, boy.” She couldn’t keep the trembling note from her voice, her sex so wet, a bead of her juices was already coursing down her inner thigh. The phallus swung before her as she stepped close, straddling his thighs. She slapped his hip, admonishing him in a low voice. “Keep those legs together as I penetrate you. If I wanted to see those big balls of yours, I’d tell you.”
His blush was so intense she could see it wrapping around his nape. Quinton’s embarrassment always made her smile.
He made a panicky little sound from behind his gag as she placed the broad black head against the glistening circlet of his anus. It tightened down still further, a last, futile defiance.
“I want you to think of one thing as your ass stretches around me, boy.” She pressed forward slowly, but
steadily. He pulled tight for a moment, then reluctantly, his bottom opened, widening dramatically around the flared head. He groaned, tightening around the phallus.
“Relax that hole. Your ass is taking every inch of this, so you’d better learn how to cooperate with it. I know it’s big. You’re just going to have to get used to that. Learning how to take large toys in your ass is going to be regular part of your life now. Trust me on that.”
His anus seemed to pulse against the dark shaft, once, twice, and with a loud grunt, a third time.
“Quinton… open that ass. Now.”
Then she was able to push further, his opening stretching tight around the stout length. His powerful thighs twitched as she continued deeper, her breath shallow and fast, her arousal so intense she knew it would take only a breath against her clit and she’d explode.
Then, with one last moan from her captive, the phallus disappeared inside his ass entirely, her mound rubbing against the hot, inflamed curves of his buttocks.
“That’s a good boy. Good! Take that cock.” She patted his hip mockingly. “Just relax… relax now. I know you can take this. It’s embarrassing, isn’t it? That you can take something this big so easily?”
He raged against the humiliating gag, but she knew it was just silly male pride. She’d never interrogated him about that particular subject, but she suspected he might be one of those misguided sorts who thought being penetrated anally was somehow “gay” or a diminution of his masculinity.
But in her eyes, it was anything but.
While it was true that there was a sizable cohort of dominant women who reveled in feminizing their men, in emasculating them, she most definitely was not one of them. She loved strong, defiant masculinity… precisely because it was that much sweeter to break, to bend it to her will. The struggle only made those men more attractive to women like her. There was great strength in submitting… especially for a man who wasn’t really a submissive.
“Would you like me to take your gag off? I’d like to hear you.” She palmed both of his hot, bruised buttocks. “Do you think you can thank your Mistress for fucking your ass for you?”
For a long beat, he made not the slightest sound, then he shivered, his legs tightening again, buttocks squeezing together.
“That just makes your asshole ache, Quinton. The more you squeeze, the sorer you’re going to be tomorrow.”
The muscular globes relaxed, his anus coming into view again. His opening was well-stretched around the phallus, rendered into little more than a thin pink ring around the merciless girth of the strap-on. She pushed it still deeper, and his head came up, a squeal muffled by the gag. His hands pulled and twisted at the ropes holding them at the small of his back.
“Ready to answer my question?”
His head nodded quickly.
“Now, if I take your gag off, do you think you can be cooperative and thank Mistress for stretching your ass for you?”
He whimpered, pressing his face to the mattress. She waited patiently on him though, and finally, he nodded miserably.
“Good boy.” She leaned over him, and he groaned as the phallus shifted deep inside his bowels. She quickly unsnapped the gag’s strap, pulling it down and out of his mouth, laying it upon the mattress next to him. She wanted him to be reminded that it could go right back into his mouth if he proved disobedient.
“Oh my fucking God,” he hissed, seemingly to himself.
“Watch your mouth.”
“I… you have to take that out.” He practically panted it.
“I don’t have to do any such thing. Maybe I was wrong to take that gag out after all?”
“No!” He took a quick breath, his hips squirming. “I’m sorry. Just… it’s too… Christ, it’s splitting me in half.”
“Are you hurting?”
“It’s huge! God, I don’t—”
“Is it hurting, boy?”
He cursed under his breath, but gave her a quick shake of his head. “It’s… really uncomfortable.”
“A nice, hard stretch, is it?” She smiled triumphantly. “You’ll have to deal with it then. Poor boy.”
He pressed his face to the mattress again, his arms pulling mightily on the ropes binding them fast.
“Stop that,” she said, laying a hand on one of his wrists. “You keep that up and you’re going to hurt yourself. Your color is good — circulation is fine. Stop resisting.”
“I… can’t!” He practically snarled it.
“Oh, I know you can.” She leaned over him, ruffling his hair. “But you don’t want to. You have to resist. Have to prove your Mistress hasn’t made you less than a man. Is that it?” She pulled about half of the length out to a sharp catch of his breath. Then she pressed forward in one smooth lunge, drawing a reed thin keen from him, punctuated by a deep grunt as she pressed her mons against his ass once again. She rotated her hips slowly, the end of the phallus frictioning directly upon her hood, her clit throbbing anew at the renewed stimulation, her arousal spiraling still higher as she stared at his anus, stretched thin about the black phallus, helplessly quivering, squeezing now and then as if it had a mind of its own.
“Please don’t,” he whispered.
“It’s okay, dear boy. This is happening. It doesn’t make you less in my eyes. Quite the opposite, actually. Only your arrogant disobedience displeases me. And even that can be amusing… every once in a while.” She pushed even deeper to the sweet sounds of his breathless grunting. “But I’m still waiting.”
“W-waiting?” He was clearly panting now.
“Say it, stubborn man.”
He dropped his head a moment, his body seeming to vibrate as if it were staked well upon the huge phallus she’d made his ass swallow, then he ground out the words. “Thank you… Mistress.”
“You’re welcome.” She pulled back, then slid it deep once more, a high-pitched intake of breath torn from Quinton’s lips. “But that’s not exactly what I asked you to do, is it? Say it properly — all of it.”
“Please don’t make me do this.”
“I’m going to be making you do all sorts of things. Your obedience to my orders might make those things considerably less unpleasant.” She slapped his sore bottom. “The choice is yours though — as usual.”
She waited for him in silence, the delicious tension in the shadowed room almost unbearable.
“Thank you for”—Quinton bit off a groan—“fucking my… ass. Mistress.”
She thrust hard, as deep as she could, the phallus rubbing against her clit, making her almost pant herself. He shuddered again, his hips seeming to be trying to writhe away from the strap-on. She took hold of his bound arms, using them as handles to pull him back full upon the thick dildo. “You’re not going anywhere boy. Now, I want you to lie there very still, very obediently, while I fuck this ass of yours.”
Reaching beneath his hips, she took hold of his cock, pleased to find it still erect, despite the way she was reaming his asshole for him. She looked forward to the day when she could take her time taking his ass, feeling for the rise and fall of his cock as she worked him. She loved the way it shamed some males as they were penetrated, that uncomfortable, humiliating stretching of that most private part of their body distracting them from their own arousal — and centering their minds on what was the only thing that mattered as the phallus thrust deeply into their bowels.
Their Mistress’ pleasure.
Quinton, to his credit, stayed quiet as she took up a firm grip on his hips, pulling the strap-on almost all of the way out before storming forward once again. She took up long, firm strokes, each time grinding the pubic hair of her mons against his well-bruised buttocks, the dildo rubbing maddeningly against her clit.
He panted and grunted as she took up faster and faster thrusting, smacking his ass now and then, cursing at him, moaning her own pleasure as her arousal began to build still higher.
“Someday… I’m going to stretch this little ass even more.” She ground deep, to th
e accompaniment of his moaned pleas. “I’ll make you scream… on your Mistress’ cock.”
His hands squeezed his elbows feverishly, the tips of his fingers pressed white.
“Please…” his breathless voice said.
She fucked him brutally then, drawing pained cries from his lips on each downward plunge, his buttocks quivering before her, his anus stretching each time she pulled back the huge dildo. She growled out the words each time her mons slapped against his ass, her breasts moving with each impact against the helpless male, her nipples hard and aching.
“You… are my good boy… don’t… fucking… move… Mistress is… gonna come!”
Her world went white as a last, hard rub of the phallus against her clit made her cry out, her head falling back. She panted out her climax as she thrust hard over and over against him, the sensitivity of her clit almost too much.
“Oh God, please…” he said, his voice strained to little more than a ragged whisper.
At the sweet sound of his surrender, another orgasm overtook her, her throbbing clit exploding with mind-blowing pleasure. “Oh Christ,” she bit out, her eyes squeezed shut as she grunted with each contraction, each incredible pulse of bliss centered at her clit.
Then she found herself laying upon Quinton’s back, his bound arms beneath her belly, her breasts pressed to his sweaty, muscled back. Her breath heaved in and out of her lungs, her own sweat dripping upon his skin.
She purred against him, in no hurry to leave him, loving the way her weight pressed him into the mattress. He was far larger than her, far stronger, but in that moment, that counted for nothing, his body, his mind, his soul conquered. Surrendered.
“Mine,” she whispered.
Chapter 25
“Does he know what’s going to happen?”
The woman was one I hadn’t seen before. Even more petite than Ivy, her black hair was cut short, spiked in a wild, yet oddly appealing, way. A black, strategically torn Misfits T-shirt hung off one shoulder, exposing a white bra strap. Though she had more metal piercing her body than probably any I’d ever encountered — including a ring through her septum — she still managed to be quite attractive. Her sparkling eyes betrayed an interest beyond professional though.