The Milking Den Ch. 09: Chase Meets Max

Chase almost weeps in relief as he feels that wave die down within him. Max heaves with a huge breath. He is close, but not dancing on tiptoes to keep it in yet. Reaching over to grab two cocks at once, I pump on both, and both boys moan in swelling bliss, but one of them has much more to lose.

“Argh, fuck, no!” Chase’s voice snaps in desperation, straining up into a strangled scream as he realizes that he’s been cornered. He’s been pushed past the point of no return. And, clench as he might and squeeze all he can, he cannot stop the semen shooting up his hard abused cock.

A spurt of cum jets out of his penis.

Max roars like a football player who’s scored a goal and Chase screams in utter defeat. I let go of his cock so that all he tastes is a whisper of pleasure, just the onset of an orgasm, his long agonizing build-up ruined but wanting more. His face is torn between frustration and fear. He knows that he’s committed an unforgivable sin. He came without permission. Nothing but swift and humbling punishment lies on his horizon.

“Clever boy, Max! And bad, bad boy, Chase. I had one rule and you broke it. And I spent so much time training you.” Chase sniffles as he stares down at his defiant dick, still twitching as a thin stream of cum leaks from it.

“Please, sir… it wasn’t a full orgasm. You ruined it. You let go just as I started to cum. Please, I’ll be good. I’ll dance for you, anything, please!”

Drunk on his abject surrender, I stuff his gag back into his mouth.

“You deserve to be punished. You deserve to be fucked in the ass.”

***

The seat of a man’s soul is in his ass.

Chase’s butt cheeks slap against each other as a robot dildo rams up into him, sending jackhammer pulses through his body, radiating out from his glowing prostate.

“Hnngh… hnggh!”

He’s gagged and leaking from his mouth and cock, and tears well up in his eyes. It’s pleasure so profoundly seismic that it exceeds the container of his body, so strong it’s almost pain.

It’s been ten minutes of watching Chase get his ass rammed inside out with my thrusting toy at full speed.

“That’s what you get for being a bad boy,” I call out over the thrusting and grunts. “But you – you’ve been good, haven’t you, Max? Have you been a good boy for daddy?” I coo as I fan my fingers over Max’s chest silkily. He’s laid out on my lap like a stretching cat, his wrists bound over his head and his cock in my other hand. While Chase is getting pounded fast and painfully, I’m letting Max enjoy my slow, satin strokes. He looks like he’s trying not to sink into a sweet, deep nap; his face is strained in the tension between surrender and containment. He’s also looking over at Chase curiously.

A strained cry interrupts Max’s sweet cooing – Chase is getting another ruined load milked out from his dry but unquenched cock. Thick white cum dribbles out impotently, the ghost of what could’ve been a good, juicy orgasm.

Chase’s face is stricken with panic.

“I’m hawhry!” He cries, leaking even more drool from his gag, as his abs flex and try squeezing out as much pleasure as he can from that sour spurt.

As Chase heaves in exhaustion and shame, I switch off the dildo and stand before him for a bit, admiring the state of this man. I can smell his failure, see his labour dripping off his muscles.

“That’s your punishment for cumming without permission. You wanted to cum, so I made you do it again. Are you going to work hard from now on?”

Chase nods obediently like a schoolboy and I ruffle his messy sweaty hair.

***

GAMES TO PLAY WITH BOUND BOYS: CHICKEN

Since Chase lost the first game, he starts in the receiving position: tied to the bed and blindfolded. Max leans by the side, waiting, drinking in the sight of Chase’s body.

“Next game. Chase: your job is to not moan out loud. Max: your job is to make him moan and beg. Later, we switch. The guy who makes his prisoner chicken out and moan in the shortest time wins.”

Chase squirms helplessly, and Max surveys his prey. Straight as he might say he is, the idea of conquering another man and torturing him with sex makes him feel strong and mighty.

“There’s just one catch, Max.”

Max’s warm eyes tense up. He knew this was too good to be true and bites his lip as I hold out a small cardboard box with a hand-sized slit in its cover.

“Pick a card.”

Max drags himself towards me. I might as well have asked him to pick the dildo I want to fuck him with. Blushing, Max reaches a strong hand into my box and pulls out a white card. His eyes scan it and what he reads makes him squirm:

“You can’t use your hands.”

But is he squirming out of awkwardness or anticipation? Max laughs nervously. I know, from the way he buzzes and from that plumping bulge, that part of that nervousness is glee.

“Go on. You know you want it,” I goad and smack his ass playfully.

Slowly, like Adam and the forbidden fruit, Max approaches Chase’s bound and exposed frame from the side. “I’m sorry, bro,” he whispers into Chase’s ear. “No hard feelings, okay?” Chase laughs resignedly.

And then, Max bends over Chase’s shoulder and nuzzles Chase’s neck.

Chase holds his breath. This is easy.

Max needs to go harder. He needs to break Chase if he wants to cum himself. He needs to let go of his ego, abandon his conformity to straightness. Steeling himself and pushing his own pride out the window, Max grazes Chase’s neck with the tip of his tongue.

Shocked by that warm, wet lick, Chase seizes up and inhales sharply, but he’s still safe; he hasn’t moaned out loud. But Max knows he’s onto something. Climbing onto the bed and perching over Chase on all fours, Max licks downwards, ending in between Chase’s pecs. Chase can’t see, but he knows what’s coming, and his whole body tenses up in anticipation.

“I’m sorry,” Max breathes. Sinfully, degradingly, but so deliciously, Max licks and sucks on Chase’s nipple.

I grope myself over my jeans as I watch Max the “straight” guy get gay out of his own need to cum. Max the fitness coach – Max the straight, married man – is now naked, hunky, nipple-licking Max. Drenched in lube and sweat, bent over another man and thrusting his face into his pecs. Only here, in this safe space, can Max explore these fantasies.

Max licks and sucks like an artist wielding a brush and Chase does a magnificent job holding it in. He squirms and thrashes, making subdued begging sounds, but keeps his lips tightly shut. Max intensifies his efforts, rubbing his chest against Chase’s abs as he swirls and teases. He’s close, he knows it…

“Alright, Max, you can use your hands now.”

Max draws his breath like a thirsty dog at a stream. Taking Chase by total surprise, he leaps onto his sub’s neck. He licks him mercilessly right behind his ears and flicks his wet nipples with his fingers. Totally overwhelmed, Chase finally breaks into a strangled moan, his entire body dancing with painful pleasure. Max presses on, savouring his win, making sure Chase’s moans are real and needy.

“Hahaha, fuck! Get off!” Chase struggles and thrashes. With the triumphant air of a warrior, Max slaps Chase’s tired chest and crawls off him, beaming and satisfied. I stop groping myself and check my watch – four minutes and twenty-five seconds.

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