“Come on cupcake, don’t be a little pillow princess, Timmy.”
Timothy’s eyes open, bleary and full of tears. The overwhelming stretch of Jack, slipping inside him and nudging his way into an experienced hole makes him whimper, hips shuffling further apart. It didn’t hurt as much as Timmy expected, it just-- was so damn thick, and Timmy always cried even when jerking off: it was just a weird side effect of pleasure.
The younger man buries his face into his arms, sucking in sharp, shaking breaths as Jack above him chuckles. One hand rests on his back, the other spreading open his cheeks so the egotistical dick can get a good view of his cock being enveloped by such a cute, flushed hole. Perfect.
“Never thought fucking myself would be so damn cute~” Jack purrs, and Timothy is mortified, wishing he could just melt and not think. Jack promised he’d ease up on the dirty talk; Timmy knew agreeing to sex with Jack was like playing with a lit match, but fuck, he just had an itch he needed scratched and currently, the fat cock spearing him open is beginning to help with that.
The over-sensitivity and burn melts into something simmering beneath his skin. The soft groan that leaves Jack’s doppelganger has him reeling, his own mind becoming cloudy at the idea of fucking into such a treat. Timmy was a virgin when it came to this-- he knew because Timmy confided in him with flushed cheeks after Moxxi tried flirting with him, and God, didn’t Jack’s cock get nice and full after that? The idea of popping this one’s cherry, making him cum untouched on his dick, fucking his tight hole into something nice and easy to use daily? How could Jack ever refuse!
Speaking of, Timmy’s just making little uncomfortable noises, knees shifting further apart, his body just tingling with the slightest bit of pain. He’s sure it’s supposed to feel better than just this; other than the near impossible initial stretch of Jack-- who’s well gifted in that department-- Timmy feels a bit let-down by the lack of stimulation.
“Hey, I’m talking to you.” Jack smacks Timothy’s plush little bottom, and the younger man yelps softly, shuffling a bit as he tries to steady himself, pushing up to be in an adorable doggy position that really makes Jack’s cock throb insistently. But some little thing in his chest is telling him to be patient, that it’ll all be worth it in the end. He tilts his head to one side, some greying locks falling in front of his mismatched eyes. “You deaf, princess?”
“I- I d-don’t know what to do, Jack,” Timmy admits, and god, he flutters his pretty lashes that Jack didn’t realize he had. Looking into a mirror like this, it makes his cock ache all the more. He’s only halfway sheathed inside Timmy, stopped by his lack of mutual action, but hey, the idea of Timmy being such a naive virgin makes him grin and chuckle, smoothing his hand over that soft ass.
“Never seen any porn, kitten?” Jack coos, continuing to push inside. Timmy shudders, gasping quietly as the fire reignites beneath his skin. His fingers tangle into the sheets, and he hangs his head, bleary eyes catching sight of his own cock hanging plump and heavy between his legs. There was only so many things the doctors could alter to make them mirror images, and once the bikini line came up, nothing was touched.
His curls trailing down his navel, framing a chubby freckled cock, darker than his altered skin tone. Revealing hints of the man he once was. Jack held their cocks together at the start, cooing at the differences-- the short and plump cock next to a fat and long one. The teasing only made Timmy harder. “N-not really,” he admits, closing his eyes. “I d-don’t like how m-mean they are.”
“Ohhh baby.” Jack’s voice is only slightly taunting, settling closer until his hips are flush with Timmy’s ass. The younger man hiccups a bit, tears continuing to slowly roll down his cheeks, sucking in a sharp breath once Jack bottoms out. It all hits him at once; the stretch, the beautiful feeling of being so damn full. Timmy whines, dropping down to bury his face into the pillow again.
God, is this how Wilhelm feels when Nisha was fucking him over their car for a quick session? Timmy tried to avert his eyes then, to give them some sort of privacy. After all, Athena and Claptrap could ignore it just fine, but Timmy? His eyes kept jerking back to the sight of the two, watching as Nisha’s bright purple strap plowed into Wilhelm, making him utter all kinds of sounds. Timmy used that as jerk-off material until Jack got to him.
And now, his mind is fixated on the feeling of being stuffed full, tucking away this memory for later use. Jack begins to pull out with a soft chuckle, purring, “Don’t worry kitten, Papa’s gonna do all the work, mhm~ You just lay there for tonight, let me teach that pretty cunt how a real cock feels.”
Timmy feels a jolt under his skin, and his breath hitches, the idea of his tight hole, squeezing desperately around Jack’s retreating cock, being called something so vulgar makes him whine. He tries to reach one hand back, to stop Jack with protesting whimpers, but the older man grabs his wrist and pins it, growling, “Oh no no, sweetheart, you’re gonna let me do the work, hm~? Just lay there and look pretty, Jack, you little slut. You’re gonna let me fuck you, and you’re gonna take it like a bitch.”
God, that shouldn’t turn him on, but it does, and Timmy feels fresh tears spilling from his eyes. He’s such a crybaby, but being degraded makes his cock jerk and spill more pre, and all Timmy is hiccup, softly mumbling, “Yes sir.”
Jack feels like a heavy stone settles in his gut, but he doesn’t know why. Seeing Timmy cry has his own dick pulsing with need, but also makes him feel-- weird. No matter. He pulls out the very tip, watching Timmy spasm for him and whine like a practiced slut already, before he thrusts back in sharply, laughing and moaning at once when Timmy yelps.
The younger man wants to bite down on something or cover his mouth. Hearing himself make such submissive noises in Jack’s voice is making his cock throb all the more, and he definitely notes to start moaning a little more while masturbating for some fuel, but right now, Jack’s started up a even, slow pace. Dragging his cock out slowly, before thrusting back in sharply, his hands resting on Timmy’s hips now. It makes his stomach flutter, the pleasure floating over him with the barest brushes.
Timmy wonders why he doesn’t feel as overwhelmed as he expected. He’s sufficiently aroused, definitely; his cock is rock hard, and aching to be touched, but Jack’s not brushing his prostate yet, and he’s about to shuffle and whine.
But the other reads his mind, shifting his angle and suddenly his cock finds the target. Timmy’s whole body jerks, and he cries out in surprise, burying his face into the pillow and mewling. “Oh-- Jack, Jack-- Fuck, right there, please!?” He feels so dirty, calling out almost loud enough for someone in the facility to hear. He shifts to cover his mouth--
“No ya don’t, kitten~!” Jack grips a fistful of his hair, yanking Timmy up. The way the younger’s back arches like a bow, so beautiful and toned, makes Jack growl, sinking his teeth into the other’s neck. Timmy sobs out suddenly, more tears springing to his eyes and cascading down his flushed cheeks. The sharp pleasure is making his cock flex, oozing pre against his thigh. So damn aroused and flushed, drooping down by its own weight.
“You’re gonna moan like a porn star, cuz that’s what Jack does.” The older man moves his free hand to cup one of those plush pecs, softened by the months of break, good food and wine. He takes a nipple between two fingers, pinching and tugging, and Timmy cries, yowling like a cat in heat. “You’re my little whore, and I want all of fucking Hyperion to hear. Come on Jack, louder.”
Timmy’s sniffling, eyes blurred by his tears, his whole body burning in arousal. Jack has a mirror on the headboard-- because he likes to watch himself jerk off, Jack once told him-- and Timmy catches sight of his face. His pink lips are rounded into a cute ‘O’-shape, panting, nearly drooling. His cheeks are dark, flushed, wet with sweat, and a steady stream of tears spills from his pretty mismatched eyes. His perfect hair is tousled, and he’s got a couple marks from their make-out session earlier, darkening into hickies.
Jack catches his eyes in the mirror, and his cock jumps at the sight. Jack is looking at him like he’s so goddamn beautiful, and some sappy part of Tim wants to believe the older man isn’t looking at his doppelganger, that he’s looking at Timothy. His heart aches a little, but he won’t let it interrupt this, head dropping to his chest. Not when Jack’s thrusts become just that bit sharper, faster, harder. Timmy moans out for him, the pleasure sweeping over him in waves. He feels so oversensitive, so good and used, and he wants more.
“Look at us, kiddo.” Jack coos, taking Timmy by the jaw and forcing their eyes to meet again in the mirror. His hand moves from the younger’s nipple, to run over his soft belly and stroke the soft skin. Timmy was adorable, so soft in all the perfect places. This warm feeling in Jack’s chest slows his thrusts to a steady, leisurely pace, stuttered by how fast emotion begins to fill him. His eyes never leave Timmy’s, locked together in the mirror.
“We’re a goddamn masterpiece.” Jack nips his ear, making Timmy shudder. He slips his hand down to cup that pretty cock, squeezing it and shuddering when the younger man whines softly. His hips buck forward at the noise, and he’s not sure how much longer he’s going to last. Not when Timmy’s pretty lashes flutter, when those tears continually spill, when his cock is a goddamn treasure.
He rolls his hips, grinding firmly against Timmy’s prostate, watching his eyes roll up as a soft whine leaves him. They refocus on Jack’s again, and he whispers, “Please... I want-- I want....” But the coiling feeling in his gut makes it hard to vocalize his wants. But they’re nearly in sync, Jack suckling another bite into his neck, his hips speeding up.
Each thrust alights Timmy with a new round of arousal, panting sharply and whining. His hole spasms and squeezes around Jack’s dick, begging, “Please-- fuck-- Jack!”
He doesn’t need to be told twice.
Jack pulls out, throwing Timmy down onto his back. He takes one leg and yanks it over his shoulder, shoving his other leg wide open so his cock can plunge right back into his slick, tight little cunt. Timmy sobs, his back arching, mismatched eyes looking up at Jack with this simmering expression that makes Jack’s brain short-circuit. But a cute, impatient roll of his hips, and Jack goes back to work.
He hunches over Timmy, sharp bucks of his hips pounding away. The slap of their skin, the wet noise of lube and Jack’s cock fucking his pretty hole into a soft, clenching smoothness-- it’s all so much, making Timmy hiccup and cry, trying to cover his face. But Jack won’t have that.
“No no, kitten.” He slaps Timmy’s thigh, pounding into him harder and growling, “No, don’t hide-- come on, play with yourself, Timmy. I wanna make you cum on my cock, wanna feel your greedy cunt, can you do that~?”
Timothy’s eyes widen, and god, hearing his own name uttered in such a filthy voice makes his whole body shudder. He obeys like a good pet, one hand cupping his soft chest and squeezing, the other shoving two fingers in his mouth.
Jack groans, dropping Timmy’s leg and planting both hands firmly on the bed. Now he’s grunt-fucking him like his life depends on it, snarling out husky praises, dirty degrading names, and Timmy nearly chokes himself with how eagerly he thrusts three fingers into his mouth, gaze on Jack; trying to show him how eagerly he would suck his cock, how messy he could be.
Jack feels that heavy, warm feeling again, ontop of the fucking burning arousal making his cock harder than a diamond. He growls, eyes closing briefly, slamming in quicker, chasing his release.
“Oh fuckin’ christ Timmy, you’re so fucking sexy-! Your fucking cunt is so tight and wet for me, I’m gonna make sure I fill you up, pumpkin, you’re gonna be bred like the little slut you are--!” Jack’s hissing filth, and Timmy can’t last like this; not when he’s being wracked by waves of pleasure, fucked within an inch of his life.
His orgasm hits him like a freight train, and he yanks his hand out of his mouth, screaming out and babbling nonsense as he rides the rolling pleasure, sobbing, “Jackjackjackjackjack fuck me fuck fuck me--!! Please please oh god please fuck me, god, I love you I love you, cum inside, pleasepleaseplease cum inside me--!!”
Jack yanks Timmy up, smashing their lips together and gasping into his kiss when he cums, cock pulsing and spilling heavy into Timmy’s spasming hole. He feels tears on his own cheeks, and he isn’t sure if it’s Timmy’s or his own, but all he can think of his holding the fucking doppelganger to his chest and never letting go.
They shiver under the final throbs of their climax, Timmy going limp and Jack’s arms. The older man struggles not to just collapse on top of the younger man, carefully pulling out and laying down, keeping Timmy just against his chest. He blinks rapidly, his eyes bleary with tears.
They don’t say much after that. They don’t need to. They just know.