The Milking Den Ch. 11: Kaizer

Story Info
A brazen stud wants to join the milking club. Can he?
5.8k words
4.77
3.4k
10

Part 11 of the 11 part series

Updated 02/10/2024
Created 08/20/2021
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Kaizer's muscles coil and struggle. He sputters a mix of grunts and whimpers, trying his best to hold the heat in. His brows clench tight at the point where fortitude frays into frenzy. Mentally, he refuses to be broken - and it's my pleasure to defy his sanity.

I shake a fist as Kaizer watches doggedly, and I drink in the way his eyes widen in hard anticipation of what's inside. He's been driven so close to becoming painfully, rapturously insane - all by one single toy.

I release my fingers, and a die - a tiny red cube - tumbles across his wet tortured abs. Its impact sends thrills across Kaizer's chest. He strains his neck trying to peer down at what he has to endure next.

"No, no, no, puppy. What did we say? No peeking." A blindfold slides across his sweaty brow, and tremors seize his body.

"You don't need to know. You just need to take it."

And then, the screaming begins.

But if it's truly suffering, why did Kaizer's cock harden even more?

--

I thought torturing guys with pleasure was a niche kink, but you all proved me wrong! I'm amazed by how many of you have followed me throughout my journey. Many of you have written in to say that you feel like my stories transport you right there to the scene itself; you can almost see my boys writhing, taste their sweat, feel the oil gliding over their chests. Just as I wanted.

And of course, some of you have also written in to ask me to reveal more about the life that I lead. How do I meet these boys? Where do I live? And can you meet me one day too?

Sadly, out of secrecy, I can't answer a few of these questions. But I can tell you one thing:

I'm not the only one.

Across the region, there are many of us, and we form something of a cabal, a secret gentlemen's club of pleasure. Happy, well-adjusted men who provide an outlet - in more than one sense of the word - for like-minded guys to release tension.

Some of you might want to sign up for a milking. Well, the line is long... and be careful what you wish for.

But apart from signing up as a boy toy, there's an even more secret and exclusive path that only the most seasoned can take. Men who, like me, have been primed through the experience of life and sexual tribulations.

Some men sign up to become masters too.

And the process is simple. To join our ranks, pledges have to be trialed by the other masters in their region.

There are three of us in my area and each of us have a specialty. Nick has the sharp sense of a bloodhound and stops his strokes at the pinprick point before orgasm. Rai is a man of endurance who keeps his boys' engines at their biting points for as long as it takes to make them beg. I know their expertise firsthand. We are not strangers to each other's gifts.

You might be wondering - what's my specialty? Might you have deduced it by now, going back through my stories? Look at how I wring the bodies, cocks and minds of my boys. How I make them beg for it, make them want to be tortured.

My gift is in digging my fingers into my boys' minds.

Make them want it so badly they'll do anything.

So why am I telling you this?

Someone is coming by for his trial with me later, and I'm the final one on his roster.

--

The trials are tough. Each one is a full day, and the master gets to use the pledge however he wants. Of course, that's bearing in mind common sense, good humour and that we're all just here to have a good time. Yet, the trials are trials. They are meant to stretch the guy all the way to his breaking point and go beyond it in a hot explosion of pain and pleasure. After all, you can only give what you can take. So we are going to make him take, take and take.

Me: how's Kaizer?

Nick: solid guy. he lasted all the way and didn't shoot until the end. some near misses but he held on through - wish I could have punished him, haha!

Me: sounds like a challenge for me ;)

Nick: yeah, he's the strong type - just the kind you enjoy!

Me: hahahaha, you know it ;)

Rai: bro he stayed on the edge for six hours straight - didn't quit, ask for permission, just stuck through! really earned his load at the end - and it was big!

Nick: whaaaaat!

Rai: ya ikr

Me: thanks guys. now I know what I'm up against

Nick: do your worst!

Rai: ya, do it for all of us

Me: ;)

--

Fuck, Kaizer is hot.

"You know why I'm here, bro." Kaizer's voice is a deep chocolate flow. Self assured, with a gravity field of his own, he walks into my house as if he's the one who's going to do the milking. He knows he's sexy, and getting two trials under his sleeve has added a cockiness to his charm, his slight swagger.

"Just one more to go, and you become one of us. Ready for the final showdown? The den is down the hallway."

As Kaizer walks past me, his eyes brush past me like a soft warm tail of a cat.

"You call yours a den? Cool. Nick calls his a torture chamber. Rai, a parlor of pleasure." Kaizer looks around the room like he's browsing through a bookstore. His brazen, charmingly careless attitude is practically begging to be taken to task.

Why did he have to come in as my potential equal, and not one of my boys?

"I haven't seen you around before." I responded. Both of us stood on opposite sides of the black milking bed.

"Oh, yeah. Moved here for work. I was pretty active back where I came from. Gotten milked a few times myself, then I decided I wanted to be on the other end of things."

"You want to become the predator, not the prey. Get to jerk off the hottest guys in town."

Kaizer's palm smoothed over the bed's black skin. This tempting image - a dignified gentleman of a stud, dressed in business formal, perfumed with cologne and liquor and rubbing his bravado against me like a fox - made me weak for him. He knew the sort of appeal he had, and he was using it.

"Actually, I'm straight. No, really. I'm just a connoisseur of pleasure and strength. I love women, but my own appetites are intense. Rough. Lust only another man can... endure."

Kaizer savored that word. He relished the exquisite tenderness that budded in suffering.

I already knew that he would be a top class master. I even found myself wondering, fantasizing, what he'd look like in leather...

But he's not there yet. Kaizer has to go through me first.

"Oh, pardon me. I'm here to be milked. Please, sir, go ahead. You'll find I'm ready for inspection." He sidled up onto the bed with a flourish and coy grin, leaning back, sliding his thighs open.

Oh fucking god.

I need a shot of vodka.

"Strip."

"My pleasure." Kaizer undoes his cufflinks and unbuttons his crisp shirt, revealing deeply carved pecs and clean cut abs. I can already imagine myself nuzzling downwards, taking in their warm contours and scent. As Kaizer continues his sleek strip show, he gets harder on the attention. He steps out of his trousers, revealing his thick thighs, and peels off his black cotton socks. Now, he's just standing there, built like a demigod, the prize wrapped in tight black luxury briefs.

He's rock hard already, his cock surging with bravado.

I'm just staring at his bulge. I want to look at all of him at once. Feel, taste all of him.

"Want to do the honors?" Kaizer taunts.

It's suddenly really warm in the room.

"Get on the bed. Hands above your head, feet apart."

--

Kaizer is really hard to milk.

The thing about a good milking is slowly undoing the layers of your man, peeling back his restraint and warming him up with pleasure until he's a grovelling, begging wet mess. Loosen him up - make him desperate to be worshipped, give him over to his fantasies of being a stud.

But Kaizer already knows he's a god. He knows that I want to worship him. Even though he's strapped down to the bed in his underwear, he's the one in power. Cocky confidence shines in his eyes - my fingers tingle with anticipation, and he sees them dancing.

Two of my comrades couldn't break him. It was down to me.

"I'm your final trial. Simple - if you make it through three stages, you become one of us."

"And if not?" Kaizer asks, a taunt dancing in his voice. My cock throbs as his does at the thought of putting him through unbridled punishment. For me, it's getting to do what I want with his body. For him, it's knowing he has this power over me - that I want him, and he knows he can wrestle me into his mercy.

"Worry about that when we get there. Today, we'll be playing a game."

I pull out a little red dice from my pocket and bring it up to his eyes.

"Each number will tell us what to do to your body for ten minutes.

One - stroking.

Two - vibrator.

Three - nipples.

Four - anal.

Five - rubber pussy.

Six - move on to Stage 2.

I'm sure you know what the number one rule is by now, right?"

Kaizer smirks. As I read out my list of torture, I could feel heat pulsing from his body. Lapping up each word, imagining my hands spreading across his skin. Kaizer wanted to drink up his destruction.

"Yeah."

And we say at the same time -

"Don't cum without permission."

I let go of the die, tossing it across his chest.

"Five."

Since a good toy is a lubed up toy, I waste no time at all. I squeeze a thick long drizzle of lube all over Kaizer's body, thighs and crotch, drenching his briefs in sex syrup. As I spread the slippery stuff over his body, taking a tour of his delicious chest, abs and thighs, my fingers tingle, and Kaizer's body arches upwards in craving, a cat nuzzling cream. I tug his soaked briefs down, releasing his hard cock like a jack-in-the-box. Shaved, thick and huge, it's the perfect sex toy, attached to a life-sized smirking Ken doll.

"I hope you're ready for your milking."

Kaizer sighs in heat. "Bring it on."

Kaizer's cock is hot and throbs in my hands. I warm it up with a few strokes, just to enjoy the feeling of his thick hardness, and then ease him slowly into a ribbed Tenga. Kaizer lets out a dark, juicy moan. "Oh, baby." I work up a slow rhythm, and he starts thrusting into it, and we get to a pulse that's fast enough to stoke a fire but not enough to make him overflow; just enough to make a man go a bit crazy. Any of my other boys would have started panting, sighing by now - but Kaizer fucks the rubber pussy with long, delicious strokes.

"Don't get too comfortable. You gotta last ten minutes inside."

Masterfully, Kaizer regulates himself. His thrusts are deep and strong, but at a pace measured enough to keep him just beneath boiling point. As he fucks the Tenga, he hypnotizes me with the rocking of his hips, the slow juicy contractions of his abs. His face warms up with pleasure. Eager to taste him, I nuzzle his inner thighs as I pick up the pace, and Kaizer moans as I rub my snout into his muscular legs.

Somehow, with superhero stamina, Kaizer lasts all ten minutes even though the rubber pussy sucked on him with a tightness and pulse that would have made any other boy whimper and weep. He's lightly dusted with sweat, mixing in with the lube plastered over his body to intensify the shine on his muscles like a visual man feast.

Damn. He's good.

Kaizer grins and exhales in relief as the Tenga releases his cock. He's still hard and ready to go.

"How was that?" I ask. I know how it was for me - delicious. Kaizer chuckles with a smirk.

"It was awesome. Did you like it too?"

I have to break him, or I'll look bad.

Another roll of the dice...

"Four. Oh, you're gonna hate this."

I feel my own cock twitch with excitement as I pulled out a dildo - one manageable enough to start, but sizeable enough to provoke a whimper. Kaizer might have held on to his dignity while he got serviced by the Tenga, but surely he wouldn't be able to take getting fucked in the ass.

"I know what you're thinking."

Kaizer taunts me as I bring my dildo, arched to provoke maximum prostate stimulation, to his anus.

"I know you're trying to make me sorry I signed up. Make me beggggg." His voice is smoky like a bar at midnight. He arches his lower back, giving me his ass, almost eager to take in his anal trial.

"But trust me... I know I'm good. You'll be begging me by the end of the night."

As much as he knew he was hot, and that I was getting weaker and weaker for him as we progressed through his trial, I was getting competitive too. My own reputation was on the line - it was me or him. With a bit more force than needed, I drove the dildo up into his ass, hard enough to make him gasp a bit.

I whisper into his ear. "We'll see about that."

And then, I thrust into Kaizer like waves rubbing up against the shore. My rhythm ebbs and flows, with rushes and slow lulls. As Kaizer's body loosens, opening up to take in more and more pleasure in, I start rubbing the toy's arched bulbed tip left and right inside him. It doesn't just go upwards into his prostate; it kneads it from the sides, all around like a fugue of deep sweet agony.

I see a bit of what I want; Kaizer's brow knots, and his wrists tug against its black leather restraints ever so slightly. Precum starts pooling where his cock head bounces against his abs.

"Four more minutes."

As the timer ticks down, my thrusts get stronger and harder. I want to hear Kaizer more than moan; I want him to keen and whimper. But my technique is as useful as a candle against steel. Kaizer is hot and bothered, but his willpower is strong. He bites his lip and scrunches his brows, but he's holding on tight, riding the wave, refusing to drown. He arches his back, taking in my dildo-fucking like a slutty cowboy, but his abs are clenched tight, holding his churning cum in.

3, 2, 1...

"Time. Damn, you're good."

Kaizer releases his breath and swears as I pull out my dildo from inside him.

"I know."

Kaizer is still determined to push through, but I can see that my wiles are wearing him down. He's panting heavier than before, and his cock looks redder and hungrier. Soon, in a matter of time, he will be mine.

The red die tumbles across his abs again.

"Three."

I crawl up onto him and nuzzle my face into his pecs, sniffing his manly exertion as my tongue finds its way to his nipples. This round is easy. It's not so much for him as it is for me, to curl up beside him and enjoy his body. Nipple play won't make him cum, but it will torture him; it drives his libido straight down to his cock, makes it thirst and demand to be touched. But I won't do that. I will deny him and make him beg me to stroke him again.

As I feast on his nipples, I can hear his breath start to crack.

***

After a break, we're back for Round Two. Now, Kaizer is strapped down to a reclined chair, freshly oiled, blindfolded so he can't see the clock.

"Same set-up: each number is its own challenge, and you have to endure until you roll a 6 and move on to the last stage.

In case you forgot:

One - stroking.

Two - vibrator.

Three - nipples.

Four - anal.

Five - rubber pussy.

Six - move on to Stage 3.

But things are different now -" for dramatic effect, I lick him in that part of his neck that I've discovered sends a shiver down his body - "you get to tell me when to stop."

"What does that mean?" Kaizer asks. The way he holds his body is softer now. It's more pliant and open to pleasure.

"That means you have to keep your timing in your head. If you tell me to stop after ten minutes are over, you're safe. But if you ask to stop before ten minutes are up... we'll add one full orgasm to your punishment milking."

I feel Kaizer's body tense up. He knows this will be hard; it's dawning on him that he's not coming out of this unscathed. But if he's really scared, why did his cock get harder?

"One. Good old stroking."

Kaizer moans as my palms clasp around his cock, and honestly, I do too. His cock is an instrument of delight. It's big enough for both my fists, and its gentle upward curve makes it the perfect weapon for taming his sexual partners. Reducing them to mindless, begging slaves asking for more.

"Oh, fuck..."

Round One has softened him up. He's been fucked, sucked and stroked for more than an hour. I've only been jerking him off for about three minutes, and I can see the word "stop" dancing on his lips. I can almost see his thoughts knotting, unknotting and wringing themselves out in his head. Has it been ten minutes? Can he tell? Is he still keeping count in his head - or has the warmth of my hands and that slow build inside his loins, simmering at the base of his cock, melted away his willpower? Kaizer's body trembles and so does his mind.

I love it. I was always in it for the mind.

"St... stop."

I let go of his cock and chuckle.

"Kaizer, Kaizer, Kaizer."

Kaizer's jaw shakes.

"It's only been four minutes. You know what that means."

"Fuck!"

"That's one orgasm added to your punishment count. And trust me, there's more coming on the way. You're leaving my den a broken man."

As Kaizer curses and tests his bonds, the little red die dances along his thighs, landing on...

"One. Looks like it's stroking for you again..."

"God damn it!" Kaizer knows he's done for. He can already feel the draining happening... and it's making him get harder and harder.

Wickedly, I pick up his cock again, stroking its length with one hand and polishing his head with another. Kaizer writhes and squirms. Can he take this for ten minutes?

And also - does he know that I actually rolled a six?

Behind his blindfold, Kaizer doesn't know anything. His mind is being drained out of his cock. How can he count and think when there's an atomic bomb at the base of his being and I'm pressing on its buttons?

Resigned, Kaizer realizes his role - to sit there and take the pleasure as it comes.

But it's not a role he easily accepts.

Kaizer buckles down and clenches his core, making his abs pop in the oiled light even more. This time, he's determined to wait it out, but his mind is slipping. I can feel it in the pulse in his cock. He's getting desperate - and the part I savor the most is when willpower and lust rub against each other to spark a flame.

"Oh, god, I'm getting close."

I change my strokes - now, my hands form a tunnel that spiral up smoothly into a vortex over his cock head.

"Are you asking me to stop?"

Kaizer grunts as his abs crunch so beautifully that I can't resist rubbing my face in them, licking their tight carved contours.

"N-no!"

"But you know what will happen if you cum without permission, right?"

Kaizer lets out a strangled cry. "But I don't think it's been ten minutes yet!"

I pick up the pace on his juicy cock. My plan is working.

"That's your call, Kaizer. You're gonna get punished either way. Which one do you want?"

I can't resist anymore. I slide my fists down to the base of his cock and lean forward, taking his thick shaft in my mouth. Kaizer roars like a suffering beast as I suck and lick on his perfect penis, feeling it swell warmly against my tongue. Kaizer wants to thrust, give in, tug painfully against the leash of his mind.

"Oh, fuck, I'm so close!"

"Mmhmm."

How will this end...?

"Okay, fuck, stop, stop!"

I stop licking and thrusting, but I keep him in my mouth just so I can feel every single twitch and struggle as he fights his hardest to hold his cum in. Kaizer keels forward, his face totally contorted in infernal concentration, his cock a pinprick away from exploding.

And finally, he wins. The urge dies down. I release his cock from my mouth and let him sink back into the chair.

"Do you think you made it past ten minutes?"

Kaizer doesn't dare to answer.

"I asked you a question." My hands pick up the strokes again, sending fresh waves of pleasure coursing through Kaizer's wrecked body. Kaizer seizes up into attention.

"I think so? I don't know!"

"No, you didn't. That was only seven minutes."

"Dammit! Fuck!"

I slide a vibrating cock ring onto him and let it hum away at mid speed, letting it keep him warm and bothered. As he curses and moans, I walk around him, my hands trailing up against his slippery chest, and play with his nipples as I whisper into his ear.

12