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Bent over, wrists tied and ankles spread apart, the Doctor's arse is presented before the Master. Their hole is less a pinprick of a pucker hidden in the valley of their buttocks – tight and virginal – but a visibly flabby slit, whorish and mare-like. In other words, utterly ruined.
The Master makes a noise of anticipation at the sight as they finish pulling the Doctor’s trousers down, pleased that all their work has not been ruined by the renewing properties of regeneration, but eager to wreck it all over again.
Clothes divested, the Master replaces their fine leather gloves for something more suited to dealing with mess before grasping the Doctor’s buttocks and spreading them apart, stroking thumbs over the darkened wrinkled skin. The synthetic rubber of their gloves grabs at the lightly moist rim – it’s too ruined to be dry and smooth but not so destroyed to be messy and leaking mucus and anal juices all over the place.
At least not yet. It needs some maintenance to get the Doctor’s hole to the state the Master intends to keep it in - slack and on the precipice of falling out, ready for cocks or fists as the Master pleases. Always ready for whatever the Master gives them.
The Doctor’s arse is loose enough to take two fingers without any extra lube and the Master spends a moment to do so, digging in deep and twisting back and forth to spread the ass juices just within reach. They add a third finger and then another, until their thumb presses up against the Doctor’s perineum. Even through their glove, the Master can feel assflesh pressing hot and flabby around their hand.
A squirt of lube makes the Doctor’s hole soft and plush, as the Master pushes the wetness around, luxuriating in the way the breadth of their fingers can swivel smoothly in the Doctor’s ass, thumb swiping over the thickened and darkened flesh of the Doctor’s rim. Swapping hands, the Master pulls out for a moment to hook a dry finger past the Doctor’s rim, pleased at the way a small curl of gut falls out as they pull up. They continue to pull with their dry hand, finger hooked in that loose curl of flesh until more of the Doctor’s arse is coaxed out, a lurid tube of ruined rectum.
Letting go, the prolapse mostly retreats into the Doctor’s hole, a small snout of plump and delicious flesh left poking out. If this weren’t a fresh face, a fresh body of the Doctor’s the Master might leave it at that, satisfied at the Doctor being too ruined for polite company. Maybe stretch it out a little more before coming inside the Doctor and pushing that cum deep into their guts with their fist, deep enough that it will trickle out of the Doctor's slack hole as they run with their companions and remind the Doctor who it belongs to.
But this is a new face and a nearly new hole to ruin, so the Master hooks their fingers into that tongue of guts again.
“Push,” the Master orders, reaching around to press against the Doctor’s stomach with their wet hand.
They try to resist of course, a fluttering around the Master’s fingers as they attempt to clench and prevent the inevitable. But they can’t defy pressure against their guts, the weight against their back as the Master leans over them and their hole unspools at the tug of the Master’s fingers, flesh rippling out from their hole. It’s a precise push and pull the Master performs, one hand keeping the slippery tube of the Doctor’s guts from retreating back into their arse, while the other coaxes more length; alternately pressing against the Doctor’s stomach with one hand and pulling at the everted flesh like it’s a cock until it’s the same length as one with the other.
“It’s a shame you can’t see it,” the Master says conversationally once the Doctor has stopped resisting. They’re pulling at the Doctor’s prolapse with both hands now in a milking motion, the dark pink flesh running slickly through their hands like silken hair, the dark pink a stark contrast to the black of the Master’s gloves. The Doctor is groaning softly at the stimulation, an almost whimper each time the Master’s hand closes around the base of their prolapse and tugs, stretching and pulling the assflesh further out of their hole. It’s almost as long as the Master’s forearm now, plump with tension and unwilling flesh. The noise turns to panting when the Master fingers the plump hole at the end of their unspooled guts, the stimulation turning from something unwanted to something desired.
“So won't it be nice to give you a proper tail, long enough for you to see it dangling between your legs, to grasp in your hand and wank like a cock?” the Master asks, letting go of the Doctor’s hole and letting it retract as much as it can. The Doctor keens before gasping at the sudden lack of sensation on the slack flesh left hanging out of their hole. It truly looks ruined, red and baggy like a worn-out sock and almost as long as one. Still not enough for the Master and they lick their lips at the thought of delivering on that promise as they appreciate what they’ve achieved so far, waiting for the Doctor to ask for more.
Only air brushes over the Doctor’s fucked out hole for a long minute, wrinkled crimson flesh pulsing with their heartbeats. The Master takes the opportunity to change their short gloves, pulling up their shirtsleeves out of the way before putting on the elbow-length ones that are more suitable for what they have planned next, allowing the Doctor to hear every rustle of cloth and squeak of synthetic rubber as the Master snaps the cuffs of their gloves into place over their elbows.
“Please.” The word is ragged and breathy, almost inaudible with how desperate it is. The Master silently applies lube to their arms and watches as the Doctor pushes their hole out, flesh rustling, straining until it’s as long and as full as it had been when they’d been milking it. The Master smacks it once it’s fully unfurled, the Doctor breathing in sharply at the sensation.
“Please,” they gasp as their guts spool back inside for a moment before they push out again, hips swaying a little to make their prolapse wiggle, as if enticing a bird with a worm. “Please ruin me.”
The Master runs a hand along the length of it, stopping at the end to hold it, weighing it in their palm before jiggling it like the Doctor had tried to do.
“Since you’ve asked so nicely,” the Master says, smashing the mass of the Doctor’s guts back into their hole, fingers seamlessly curling into a fist as their hand slips into the Doctor’s loose ass. Their knuckles and arm press into the ligaments and intestine yet to be loosened, massaging and stretching them as the Master pushes their fist deep inside the Doctor, “It'll be my pleasure.”