The Milking Den Ch. 04: Max

Max finishes his routine and stands up even shinier than before. I give his hot shoulders a nice pat and rub down his sweaty, oily front. His flanks and torso heave in rhythm to the pulse of his cock. He looks at me with equal parts gaze and glare, like he's daring me to do my worst.

"Nicely done, Max! Now that you're all warmed up, let's work on... resistance training." Max quakes as I guide him by the shoulders to a choice between the inclined bench and milking bed.

"You get to design your own workout. But choose carefully. Inclined bench-" I wiggle his left nipple- "or bed?" And I flick his right. Spoilt for choice, or rather too afraid to make a choice, he does a bit of a nervous dance as his mind flings wildly between the two. My fingers pinch in on his nipples slowly, increasing in force.

"Choose quickly before I punish you again."

Max stammers and gasps before pointing to the incline.

"Ah, good. The anal bench."

Max blanches. "The what?"

"Yep, now get on the bench," I state as I pull out a decently girthed anal prostate toy from my pocket. Max looks almost like he's about to faint.

"Then why is this called resistance training?" Totally flabbergasted, Max's entire body looks deflated and lost.

"Because you have to resist the urge to cum as the toy fucks your ass. Now get on it in 3, 2, 1 - good!" Once bitten, twice shy; Max assumes his position without a second thought. His hands are above his head, his feet spread apart on both sides of the bench, his face white with worry. Before I start strapping his wrists beside his ears, I spend a bit of time soothing his chest.

"Deep breaths. Don't be afraid, buddy. This will feel great. And if you really need to pull out, the safe word is...?"

"Smith machine." Max closes his eyes and braces himself.

"Good boy. Now get ready. And remember - don't cum."

As if he wasn't already oiled enough, I take out another bottle of baby oil and cover him with fresh shiny streaks. Max grunts, deeply and obscenely, as I polish him dazzlingly bright. Oil is such a powerful tool when it comes to objectifying men. It's what we see on magazines and shows; it's our society's mark of a fuckable stud.

All of Max's limbs are firmly locked in place. Sitting in front of his crotch, I look up at him, this god I have enslaved. He is, in a word, fuckable. Max looks down at me with a face so meek and dependent, a body fighting for its pride and a cock popping out from behind that wet red bulge.

"Now, remember how you made me go through HIIT this morning?" I teased as I finally, finally lay my fingers on his cock. I squeeze it softly through the cloth, but Max roars so loudly it sounds like he just came. "That's what we're gonna do. Forty seconds of stroking, twenty seconds rest. You are absolutely, totally not allowed to cum. Once you're settled in, I'll insert the plug."

I rip Max's soaked briefs apart and toss them aside, letting his hungry cock and balls swing out like a giant trunk. Max pleads with me to have mercy on him, but he didn't go easy on me either, did he?

"Ten minutes starts now."

I go down hard and strong. Max howls, he hoots and his body thrashes about as I manhandle his dick like I'm squeezing juice from an orange. Each stroke slides down across his entire length, spinning across every inch of his rod. He barely, barely makes it to the first rest period, and he gasps for air as though he just came back from a lap around a stadium.

"Nicely done. Time to add the resistance." I lube up the black plug with a good handful of slick gel.

"Oh fuck. Coach, please, I really can't." Max whimpers and begs, thrashing lamely at his bonds. Grinning at him like a cat cornering its prey, I wave the plug in front of his desperate pleading face.

"What is it you said this morning, Max? Oh, yeah. 'You can do it - keep your core tight and legs strong!'" Max throws his head back into the bench and sobs as he splashes about limply, hearing his own silly motivational speech thrown back at him, but he knows it's no use. I'm the PT now. His job is to take it and suffer.

"Slowly, slowly," I cajole. Max winces as I guide the plug in, and then moans like a dirty hound once the bulb on its tip finds his prostate.

"Good boy... now sit back down again." With a surprised and defenceless moan, Max realizes why this is called the anal bench. At this angle, his own body weight becomes his own tormentor; it presses his prostate right down onto the pressure point of the plug. I haven't even touched him, but a stream of precum leaks out of him just from gravity doing its job. Max winces. He tries shifting about to relieve himself of that sweet throb but simply ends up leaning into his prostate from different angles. As I watch him struggle, it dawns on me I could actually just sit back and watch him adjust himself into an orgasm.

"Let's finish up our sets!" I say again in my sexy PT voice. Max screams and begs before I even start, but I ignore him and continue pounding away at his slippery dick. I'm trying a different grip; my hands slide down from his head to his base like a neverending tunnel. Max's abs tighten even more than I thought possible, so much that they look like firmly packed nuggets of gold.

"Fuck, no, Coach - I really need to cum!" Max's face is twisted tight like the fulcrum of an impossible moment. I don't lighten up my stroke in the least. He squeezes every last bit of strength he has to gird his loins against me and he does it amazingly, even as each clench pushes his anal plug even more snugly up into his ass. Max's voice chokes. It's hell one way or another; his body is breaking, and his last defence is his willpower.

"It's all in your mind! The only easy day was yesterday!" I shout slogan after mind-numbing slogan as Max's abs and thighs clench in with all the force of a barbell squat.

Finally - somehow - Max survives the round. Once I let go of his cock for the final time, he releases a breath he's been holding for the longest time, unbuckling the unbelievable pressure he was locking within his loins. Max leans back defeated.

"Well done, Max. That was truly impressive. I guess your muscles aren't just for show." Once he's unshackled, Max rolls off the bench and crumbles onto the floor in a slippery heap. Looking up in between his deep labored pants, Max sits up and asks me a question.

"What's the bed about?" He looks up at my other station of torture, wondering if life would've been less painful that way.

"Oh, that's the nipple bed. Clamps and suction cups. Would you have preferred that?"

Max sinks back onto his puddle in bitter laughter.

"Time for our next round - endurance training. Since you chose to be on Team Red, you have to do the red exercise. Look behind you." Max spins about, giving me a good chance to admire his shining globed butt, as he discovers two boxes, one red and one blue, along the wall behind him.

"Go on, look inside." Gingerly, Max unclasps the cover and lifts it up. Inside, he finds a tight red Tenga. Extra snug, ribbed texture.

"Endurance training. Your job is to stay inside the Tenga for ten minutes and not cum. Simple?"

Max breaks into laughter.

"Are you fucking serious, dude? I've been on the edge the entire fucking day and you want me to stay inside a fake pussy and not cum?" Max is delirious. His brain is fried through with a day-long mindfuck and his ass is still aglow with that dull deep ache.

Unfazed, I charge up to him and slap his ass hard, driving the plug an inch deeper. Max roars and crumbles onto me for support.

"Listen to Coach; I know what your body needs. Now, get onto the bed while I figure out how to punish you."

Tamed and subdued, and secretly looking forward to what I have to dish out, Max wheezes out his final laughs before climbing onto the milking bed on all fours. Through one of the contraptions I've modded onto the frame, I'm able to mount the Tenga onto the bed itself. Max marvels at the technical ingenuity, but not at the torture he has to endure.

"Fuck it."

Hesitantly, Max thrusts as slowly as he can so that he won't discharge his load by accident. I stare at him, transfixed by the hypnotic sight of his abs tightening and rocking as he pleasures himself on my table. His face loosens up as he bites his lower lip, nursing a little supernova glowing at the base of his cock. All of this... a show just for me.

And as he edges himself at my command, taking it both ways while he holds his cum back like a real trooper, I walk over to the closed blue box.

"I wasn't going to use this, but you were quite rude just now, and so I have to punish you." I saunter around to the front brandishing a blue-handled flog. Shocked beyond speech, Max thrusts a bit too forcefully and screams as terror and pleasure collide.

"No, no, Coach... I'm sorry, I won't be bad, I'll do your exercises from now on - ARGH!" I shut Max up with a smart strike across his pecs.

"It's not called endurance training for nothing, Max. If you keep on arguing, I'm going to put on the nipple clamps as well. You wouldn't like that - or would you?" I pull the thin leather straps of my flog against his chin and he trembles in silent fear at its coolness. Satisfied with his obedience, I return to his rear and crack the whip across his fleshy peachy ass. Max howls. It's a sting, but I calibrate my force to make sure it's just a teasing slap.

"Good boy, Max. Now, I want you to talk dirty like it's your girlfriend."

Max spits loudly. I whip his ass again, this time hard enough to burn. Max curses and grunts like a hog in heat.

"Wow. That's good. Fuck me, baby. Take it. Yeah." Max grits his teeth reluctantly.

Seems like Max needs a reminder that I'm in charge, not him and his ego. I pull out his plug halfway before ramming it in again, and fuck him a good dozen times with it as he whimpers and roars with each plunge. A minute of rough and intense fucking later, he seems to have gotten the lesson.

"I'm doing this for your own good, Max. I'm training you to be a good stud for her. Can you see that?" Almost looking like he's holding back tears, Max nods delicately, his little chin quivering.

"Fuck and talk. Now."

Soon, Max's thrusts and my spanks meld together to form a rhythm of pain and ecstasy. "Fuck, babe, your pussy's so tight. Argh... dammit - take my cum and call me daddy, babe! Argh, ARGH!" Max grunts, roars and snivels as his face glows bright red. His pelvis rocks between the soft, warm rubber pussy hugging his aching cock and the sharp cracks on his ass, driving him totally broken and insane. He's confused; his body is traumatized into bliss. Soon, he gives up on speech altogether, sinking his teeth into the bed itself as he tries holding that nuclear bomb in his loins back. From behind, watching him rock his body like a circus lion subdued, I rub myself between each spank until I reach my own fevered orgasmic peak too. I'm drunk on authority and sizzling with the rush that only a good power trip can bring.

Finally, once I see that Max is totally wrecked, I guide him slowly out of the Tenga. His whole body is limp and his eyes are glazed over like he's been transported out of this world.

"You've done so well, Max. I'm honestly impressed. Still doing okay?" Max is tired and his spirit is fractured, but he nods slowly and nuzzles up against my neck for support. We share a small tender moment just like that, cuddling each other on the milking bed as his soul sinks slowly back into his body. His breathing steadies again and his shoulders stop quaking.

"I'm good, Coach." He smiles up at me, his eyes twinkling amidst the dark storm whirling around his face, and I ruffle his hair softly.

Slowly, slowly. Deep breaths. Preparing himself for the finisher.

"Pushups. Go." Max tumbles back onto the exercise mat, which is now slick with oil, sweat and precum, and puts on another show of shiny pumping muscle. While he warms himself up, I marvel at the little setup I own and wonder how I've done so well to have created a little infernal room for myself and my boys. Max finishes up his little circuit and looks back up at me. His face is flushed and so is the rest of his beefy body, and he beams like he wants a reward, so I give him a good strum on his nipples until precum leaks afresh. It's time to bring our boy to a rousing finish.

"Final exercise: burpees. Keep going until I'm happy, and make sure you don't cum." Finally, a smidgen of confidence shines through on Max's exhausted face. After so many hellish obstacles, this is one he stands a better chance of surviving.

But there's a twist.

I take off the red whistle hanging over my chest. Hidden behind the whistle, concealed from view, is a cock ring.

"Let me fit this on for you." I drizzle a totally unnecessary slog of oil onto Max's front and slide that black rubber ring onto the base of his cock. By now, Max knows me well. This is too good to be true. It's too easy.

"Go on. Gotta tone you up for your first night with the wife!" Both of us chuckle. As if he needed any help at all; as if his wife would demand anything close to the ordeal he's been through today.

Max dives down to the floor for his first pushup, and suddenly convulses as he groans in fatal agony.

He just found out that both the ring and the plug vibrate.

Max glares up at me with fierce defiance, his entire body trembling. He knows, I know, he knows I know - I'd set him up to fail. Each squat deepens the plunge of his plug and hastens his orgasm along with the vibrating bliss in front. Max is going to lose, and fast.

"Coach, I'm not gonna make it." Trapped at the bottom of his squat, Max can't even get up off the floor without busting the best load of his life. I grope myself as I stare brazenly down at the quivering man before me. He is so plainly ruined, crushed and humbled at my feet - but I'm not done yet.

"Don't rest when you're tired, Max. Rest when you're done." There's no way Max is emerging from this in one piece.

Gritting his teeth and bracing himself to take whatever punishment will come his way, Max launches himself off the floor with a deep and powerful squat, plunging the plug in good with the force of his massive glutes. Max makes a heinous, animal sound; a cry of total depraved defeat, loss and surrender. A hot thick load sprays like a bursting dam from his tired cock, covering the floor with his long-stewed suffering. More spurts, each as juicy and bountiful as the last, paint the floor as Max's legs give way under the primal chaos of the deepest pleasure he's ever known. Finally, Max is brought to cum by his own body rebelling against his will. Max crashes down hard. He starts crying for real, lost in the dissociation of release. His body is gratified - far more than gratified, but in total ecstasy - but his mind is terrorized by regret and panic. He knows that a sin this big must carry repentance even bigger.

I tower over him, my face twisted like the visage of a sadistic god.

"I said not to cum, boy. I must punish you now."

I dial up the vibration to the max and Max squeals, his pleasure zones attacked on all sides as his sex is forced into total overdrive. He writhes in a pool of his own cum, coating himself with his own seed, but all he knows is that he needs to get these relentless machines off his body and fast. But he's so broken, his reasoning powers ground to dust, that all he manages is to roll about and scream. I feel myself leaking at the sight of this proud boy reduced to this.

But that's not enough. I don't just want the submission of his mind but the total ripping apart of his soul. Entering the fray myself, I dive down onto his cock, polishing it with my palms.

"Fuck! Stop it, bastard! You fucking son of a bitch!" Max roars and thrashes about, but his body is so tired that I wrestle him into my grip like the little pup that he is. As he's pounded both ways by my toys, I swivel and palm his weeping cock head as his futile anger melts into suffering. I lick his neck like a vampire and strum his sore and sensitive nipples. All of his erogenous zones are hot on hellfire. Max cries and taps lamely at my forearms. "Please, Coach - have mercy!" But I continue digging, sucking, pumping, until his sobbing reaches a deep bellowing roll.

"As you say - you're in for a good one. Welcome to the milking den."

Right in that position, with me grappling Max's destroyed body in front of me on the floor, I milk another two loads out of him until he's dry. By the final load, he's given up all hope of resisting. Barely twitching, even as the vibrators grind mercilessly against his cock and ass and as my hands roam shamelessly about his body, he submits thoughtlessly and surrenders the final drops of his manhood for me. The only sign of his sentience is a soft but persistent whimper.

Once I'm done with Max's body, I wipe my hands on his chest and push him over as I tend to my own unmet need. I jerk myself off to the sight and smell of this boy thoroughly owned, knowing that every night he has with his future wife will never compare to the past two hours of sheer torture he had with me.

I wipe myself off quietly as he stirs back to life, reborn from the pits of hell, looking like he's been baptized anew.

"Hey, buddy. How are you?"

I offer Max a clean fresh towel. Now, the music is off and the mood lighting is down. Everything is back to normal. The milking den is just a room, and we are just two internet friends.

"Dude." Max sniffles. I can see the horizons of his mind slowly reforming themselves, drawing in close and wrapping him in a cocoon. His eyes look like distant stars zooming back into orbit. "Just... dude. I need a hug." And I'm happy to oblige. Max was brave enough to endure an experience that brought him not just to the heights of sexual pleasure, but to the furthest extent of consciousness possible. I rub his head as I rock him slowly, gently, like a big brother. For a moment, we are the sun and moon.

"You did so well, Max. I am so proud of you."

***

"Inviting me to your wedding?" I ask mischievously as I guide Max to the door. Even after an hour, his insides have been so pummelled that he still can't walk straight without help.

Max laughs weakly. "I think I'd like to keep this a secret. Thanks again, man. Are you sure I can't do something for you at all?"

I pat Max's back reassuringly. "I'm just glad you enjoyed yourself. I like it when I can help guys reconnect with themselves, you know? It's so hard for men to find spaces in society that allow us to be vulnerable."

Max nods solemnly. He understands; this is a chapter he'll have to leave behind now that he's becoming a husband.

"It doesn't have to be this way, you know."

"Yeah."

"I'm always a text away if you want."

Our eyes shine naughtily, with a secret understanding, as we hug for a final time. Something tells me I might see Max again.

***

Hey! Sorry for keeping you on edge for so long, but I hope Max's taming made up for it. Thank you so much for all your love and support! Your glowing kind words make me feel so appreciated, validated and loved - and it keeps me going for real. I love engaging with my readers and hearing your thoughts on what you enjoyed, what you think can be improved and what more you want to see in my stories. I can't wait to meet you all in my milking den again. Till next time!

And to those of you who couldn't hold it in until the end of Max's story: you're one of my boys now. ;)