Condensed Milker 9000
The ultimate male-milking rig for interrogation… or simply for breaking them beautifully.
Two naked males are bound to the padded plank. The bottom one lies supine, wrists and ankles already locked wide. The top one is lowered belly-to-belly, navel kissing navel, warm skin pressed flush. His arms are wrenched behind him in a tight strappado, elbows nearly touching, forcing his chest down until both sets of nipples brush and stiffen.
Thin titanium rings are pierced through each sensitive bud in a single, practiced motion. A short chain links the four rings together. When the winch hauls the top boy’s wrists higher, the chain goes taut and their nipples are dragged toward each other in one slow, exquisite pull. A low whine escapes both gagged mouths. Ball-gags are buckled deep. Drool already beads at the corners.
Their rigid cocks are aligned side by side. A single, thick onahole sleeve, custom-molded for dual occupancy, is rolled down over both shafts at once. The inner walls ripple and squeeze, milking them together. From the tip of the sleeve protrudes a double-headed catheter: two slender silicone tubes joined at a Y. Both urethras are penetrated by the twin heads inch by inch, until the boys’ eyes roll back and their hips jerk helplessly.
A wide silicone band at the base of the sleeve is stretched beneath both scrotums and snapped tight, locking their balls together in a single swollen sack. The collection tube dangling from the catheter is clamped shut (for now).
Ankles are forced into the wooden stocks behind them, legs bent and spread. A buzzing vibrator rod is wedged between their trapped balls, set to a low, cruel hum. Two thick piston dildos (slick, ridged, and already warm) are fed into waiting holes and angled precisely against each prostate.
The rear panel slides open with a hiss. A dozen slick, feathery tentacles slither out, programmed to the victims’ exact ticklish weaknesses: paw-pads, armpits, ribs. They wait, coiled, patient.
Everything is ready.
The machine wakes.
Vibrators thrum. Pistons begin their relentless thrust, battering both prostates in perfect sync. The shared onahole strokes and squeezes, the catheter tubes teasing the sensitive insides from within. Every twitch, every shudder travels through the nipple chain, yanking tender flesh, keeping them on a knife-edge of pain and pleasure.
The tentacles strike the moment climax crests (feathers dragging across paw-pads, tips jabbing under arms, wriggling along ribs). Laughter and screams mash together behind the gags, bodies arching, muscles locked rigid. They are not allowed to come. Not yet.
Saliva pours. Sweat slicks their pressed bellies. Cocks throb violently inside the sleeve.
Again and again the machine edges them, reading every tremor, backing off at the perfect second. Minutes stretch into a small eternity.
Finally the tentacles retreat. The pistons hammer home one last time.
Both boys come at once. Thick ropes of semen surge through the catheters… but the clamp holds. Their own release has nowhere to go except the other's body, flooding directly into each other’s bladders in a hot, forbidden exchange. The machine keeps stroking, milking every drop, forcing the swapped loads deeper until both bellies begin to swell faintly with the warm weight.
Hydration tubes snake through the ball-gags. Cool sports drink trickles down their throats drop by drop; they have to swallow or choke. They will need the fluid. They are going to produce a lot more milk tonight.
When the bladders are drum-tight and the boys are trembling on the verge of delirium, the clamp is released. Pure white streams gush into chilled glass bottles. Not a single drop is wasted; the Condensed Milker never spills.
Occasionally the winch lowers the top boy’s wrists a fraction, easing the pull on their chained nipples. The sudden relief makes both victims gasp… only to moan as their raw, ringed nipples rub helplessly together with every heaving breath, keeping their spent cocks from softening inside the sleeve.
The pistons never stop.
The tentacles wait patiently for the next edge.
The bottles slowly fill.
And the Condensed Milker 9000 continues its slow, thorough work until both subjects are empty, overflowing, and utterly, beautifully broken.

-- Draft by Hoya82, Edited by Grok.