Hi hi! I was wondering when you come back to writing requests, could I ask for a Pennywise/Bob Gray FanFiction with a Fem reader sharing her first time with him but it’s noncon but he tries to be gentle with her. She knows about him through the town they live in, reader is home from college which thrills him and finds a way to take her. Maybe some chest play from Penny? I really hope this is okay to ask! I love love love your penny stories there so good! Can’t get enough ❤️❤️
You are an angel for waiting so long for this. Thank you for your patience 🙇🏻♀️
Idk if Penny can be considered gentle in this one, but I suppose he’s gentle compared to how I usually write him 😂
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Use
Bob Gray/Pennywise x F Reader (NSFW)
Warnings: Noncon in the back of a van baybeee, social anxiety, age difference, objectification, degradation, supernatural elements, nipple play, fingering, loss of virginity, threats, crying, a little daddy kink, put that reader in a mating press—readers love mating press, creampie, cum eating
It starts with a prickle.
The fine hairs on the back of your neck and along your arms raise as your skin tightens and tingles. In your belly, unease writhes like a thousand snakes. Your shoulders tense as your feet dig into aging tile, ready to flee should your nervous system give the order.
Except…. You’re standing in the middle of the grocery store bakery, a warm loaf of freshly baked French bread clutched in your white knuckled grip, paper cover crinkling against your palm. It’s 1:00PM on a Thursday. Why on earth do you feel like a cornered animal here of all places?
Cautiously, you glance to your right. You find nothing more than muffins, croissants, and danishes all gleaming temptingly from their plastic containers. An employee restocks the organic section, her back to you.
To your left….
Your throat goes dry when you meet the piercing blue gaze of the lanky man hovering at the end of the aisle. Buck teeth peek out between full lips, lips that glisten with spit and curl into an unnerving grin. Long fingers slip from a tattered, tweed pocket and raise to greet you with a cartoonish waggle.
Recognition is instant. Robert Gray is unmistakable, even if the last time you saw him was as a child. Though, why the hell he’s staring so intently is beyond you. You barely know the guy.
And he hasn’t aged a day….
Suddenly, the room tilts and your stomach lurches. Your shoes squeak on tile when your legs flail, as though they’ve come unstuck from the ground beneath you. Wildly, you reach out to grip a shelf when you begin to float right up into the air.
You blink.
The feeling vanishes as quickly as it came. Your feet are flat on the floor. On the shelf, your hand shakes as you hold on for dear life.
Had anything even changed at all?
Mr. Gray still leers at you from the end of the aisle. Gasping, trembling, and not knowing what else to do, you raise your own hand and tentatively wave back. He responds with a titter and a wink before slinking away.
Once more you glance around, wondering if anyone else saw this bizarre exchange or your strange behavior. You’re only a little relieved to find yourself alone. Saved from embarrassment, but not the fear that still clings to the back of your throat.
**
At the checkout sits Marge, as round as ever. You recall the powdery smell of her perfume, unchanged from when you clung to the hem of your mother’s dress as a child. Derry remains as static as ever.
She greets you generically as you set your purchases on the conveyor belt. The beep as your goods are scanned fills the space between the two of you and saves you from conversation. You’re thankful she doesn’t recognize—
“Well, goodness gracious, I hardly recognized you!” You spoke too soon, it seems. Marge says your name like a question and you force a smile and a nod. “Where have you been, missy?”
Awkward chuckle, “Ah, college. Just back for a few weeks, visiting mom.”
“Oh I bet she is loving that.”
“Ha, yeah….”
“You kids just grow up so fast. So, tell me about school! How many boyfriends do you have?” You bite the inside of your cheek when she ends her question with a self-satisfied giggle.
“Oh, no, nothing like that. Just…focusing on school, you know….”
You continue on this like for another agonizing minute or two, forcing out answers to Marge’s barrage of questions until she prattles off your total and hands over your groceries.
“Say hi to your mom for me!”
“Will do, thanks Marge.” The bell above the door jingles as you flee to the parking lot. Afternoon sun catches you full in the face and momentarily blinds you. You manage a scrunched glance left and right before crossing the road to your vehicle.
Strained huffing from somewhere nearby makes you pause. Furiously blinking to adjust to the light, you find Mr. Gray at the rear of the white panel van parked next to your car. The back doors are wide open as he attempts to load what appears to be a folding table all on his own. Attempting, and failing.
You only hesitate for a heartbeat. He’s a weird guy, a bit unnerving with his nineteenth century garb and knowing smile, but he doesn’t deserve to throw his back out.
“Need any help?” you ask, setting your purchases on your trunk and hurrying over to him. Where did he even get this from…?
“What a good girl, gracious little thing, helping old Mr. Gray.” The strange lilt of his voice almost makes you wince. His wide, blue eyes rove over your face and down your neck until the hair on your arms raises in alarm once again. Your own eyes flick down to his wetted bottom lip, so slick it appears drool will spill over any moment. You swallow thickly for him.
“Uh, yeah, let me just, um—
Bob moves to the end of the table still sitting out in the parking lot so you have no choice but to take the other end that is half lodged in the vehicle. It’s awkward, crouching and backing into the van while maneuvering the load, but you manage to shuffle all the way to the front seats until the damn thing comes to rest on the floor of the van. Easy enough—
SLAM.
All at once the sunlight disappears but for the weak imitation trickling in through the windshield. It takes your brain a moment to realize Bob has followed you into the van and slammed the doors shut, though how he managed to move so quickly is beyond you. He now sits between you and the exit, cast in shadow.
“Little treat might be too gracious for her own good, hmm? She makes it too easy for ollllld Mr. Gray.”
‘What are you playing at?!’ The question is there, right on the tip of your tongue, but it freezes and dies when Robert Gray’s eyes glow, glow like golden fire burning unnaturally from the shadowed corner of the van. Terror zips up your spine as you choke on a shout and scramble away, intent on clambering over the center console for the driver’s side door.
Long fingers wrap around your ankle and yank. Your own digits slip on vinyl seats and you crash face first into the accursed table top. Onto your back you roll as Bob slinks over you, wedges his hips between yours, and pins you down with an impossibly strong hand around your neck. Every muscle strains as you try to buck or twist or anything, but he doesn’t even budge, doesn’t even give a millimeter.
How, how…?
Wet warmth splatters onto your cheek. Drool has spilled over his lip, a steady stream of spit that reeks of decay raining down on the side of your face and dripping into your hair. It’s further smeared up to your brow when Bob crushes his lips to the side of your head to noisily inhale. He titters, a little giggle you feel inside your head that rattles your teeth.
“Its fear is unsoiled, yes, fresh like a babe.” Confusion at his words plucks at the back of your mind, but your panic is too intense and overwhelming to spare it full attention.
“What—p-please, please stop, I don’t—
“You don’t, no, no, you haven’t. Have you, little treat?” The deep growl of his voice shakes your own chest. He looks at you expectantly as he speaks, buck teeth on full display, golden eyes wide and staring. One of them drifts to the side and you try your best to melt into the tabletop at your back.
Furiously, you shake your head back and forth and stammer out a, “Bob, please, I d-don’t understand—
“No boyfriends, it says. No fumbling hands that prod and squeeze, no one to use it like the meat it is. Sweet. Untouched. Meat.”
You blink and shake in shock. Your mouth opens but no words escape. Bob laughs, high and piercing and you flinch at the ferocity of it.
How…how could he know that…?
“No hiding from me, little bite. Mr. Gray can see it allllll. Now he has you here, all to himself. And he’s soooo hungry.” The last, rumbled word reverberates around the van and you scream, arch, kick your legs only to freeze in place when Bob ruts against you. The hard girth straining against his trousers slides deliberately along the length of your clothed cunt and, suddenly, the end game becomes frighteningly apparent.
“N-n-no, no, oh god please, don’t—
“Not like you had imagined it, is it, tiny thing? No candlelight. No love. Just old Mr. Gray and his teeth.” He sets them against your cheek, his teeth, as his free hand weasels under your shirt. You loose a protesting grunt when spidery fingers push aside your bra to pinch a nipple between thumb and forefinger. Gently, they tug and, thoughtlessly, you squirm. You tense and fall still when the movement grinds your clit against his bulge, a little zing of pleasure shooting through your belly at the contact.
Bob hums knowingly like he can hear what you’re thinking and twists his fingers ever so slightly. Instead of a grunt, a little whine slips past your quivering lips. More unbidden pleasure, more curling heat where it shouldn’t be.
“Mr. Gray’s good little girl. I can smell it now, needy, needy.” He snuffles along your jaw, and slides his thumb away so he can press slick lips to your fluttering pulse. “You stink like a virgin, too stupid to know what you need, hmm? Let him show you. Let him put your meat to use.”
Again you shake your head and open your mouth to protest, but this time the words are a cry as Bob humps you and tweaks your nipple all at the same time. Your head spins, overwhelmed by new sensation and fear of who…what causes them. Something deep down in your guts knows this is no man hovering over you.
The thing called Bob shifts his hips to the side and you tense to act, to shove, to fight, but he’s so much faster. His hand leaves your breast and burrows into your pants. Tricky fingers find your clit and stroke, perfect pressure that makes your limbs twitch and your lungs gasp. Hands poised to claw just moments ago instead fly to his shoulders and grip on reflex.
His digits sink inside you faster than you can inhale. They curl until they reach some spot you didn’t know existed until now. Even just this stretch is more than you’ve ever experienced, but the surprise comes not in the pain, but the pleasure. It doesn’t hurt, not even a little.
Didn’t they all say it would hurt?
You emit a strangled sound and then, to your dismay, a wanton little mewl follows after as Bob works his hand and rubs euphoric little circles inside you. The nails intent on scratching his eyes out have curled into the fabric of his dingy button-up and your legs fall open like they have a mind of their own. No, no, stop, you’re not enjoying this….
You shouldn’t be enjoying this….
Robert chortles in glee and finger fucks you faster until your eyes go out of focus and you arch—toward, not away this time. Still, your mouth tries to lie about your body’s obvious reaction with a stuttered, “S-Stop, I don’t…want….”
“‘Don’t.’ There’s that silly word again. ‘Don’t!’” He mocks your pathetic timbre. Next, his lips move to yours so he can growl against your panting mouth, “You don’t know what you want. Listen to that slippery little hole, hmm?” He jostles his arm and your cunt squelches in answer. “Desperate for purpose, isn’t it?”
Without warning, he rips his fingers from your channel, grabs hold of the waistband of your pants, and gives three sharp tugs. They’re down and off before you can even think to shriek. Bob grips you behind the knees and shoves, bending you in half and spreading you wide.
Fear returns with the sound of his zipper, trepidation that makes you scramble to grab hold of something and pull yourself away. His iron grip keeps you from budging, however, and you’re helpless when his thick cock lines up with your glistening slit.
“And a one, and a two, and a—
“Wait, wait, wa—
The last ‘wait’ is lost in whatever garbled nonsense escapes your throat when Bob eases forward. Unused muscles part around cock and you experience that foreign stretch and pressure for the very first time. Bob makes an inhuman guttural sound low in his throat when your walls squeeze his girth. It’s a sound that dumps icy terror into your veins, but you think what startles you most is the absence of discomfort.
Maybe it hurts, but the main sensation you feel is…delicious. Blissful. Addictive. You close your eyes to keep them from crossing.
“Useless until I found it,” Bob coos against your lips. Heat jolts in your gut and you can’t help the pitiful moan it brings. Is he the reason you’re reacting this way? Are his horrible words spurring you on? What the hell is wrong with you?
“B-Bob,” you choke out when he bucks his hips. In your shoes, your toes curl. He snickers and does it again, and again, each thrust eliciting more desperate sounds than the last. Moans and cries fill the interior of the vehicle and mingle with the sounds of wet slapping and the harsh grunts escaping from Bob’s throat. Any fight left in your fists is gone, replaced by need that has you gripping his shoulders like you gripped that shelf in the store. You could float away like this….
“Float, yes, that’s right, little girl. You’ll float. But first, you’ll cum on Daddy’s cock.”
“I-I….”
“You want to. Say it.” You shake your head and Bob snarls, “SAY. IT. Or I’ll sink my teeth into that supple little throat and paint us both in pretty red.”
“Iwannacum! I want to, p-please…D-Daddy—
“It’s learning, it’s poliTe.” The “t” sound hurts when it snaps off his tongue and Bob cackles when you jerk and shudder in his grip. Still, you don’t release him. You can’t, the insistent, hot pull in your belly too great to ignore.
Frenzied tears well in your eyes as you beg again, “PLEASE, please, I need…need….”
“Neeeeed, now it knows, now it understands what it NEEDS. Cum for Pennywise, little treat. Give it to Me.”
Pennywise…?
Climax hits you like a runaway train and wipes all sense from your mind. You shake and scream, rippling ecstasy washing over you in wave upon endless wave. Bob follows suit and hilts himself, spilling so deep you feel him twitching behind your navel. There’s so much, too much. It spills over and pools beneath you, a sickly sweet scent filling the air.
Wet fingers prod at your lips and you crack an eyelid open one at a time to find Bob insistently poking at your mouth with slick-covered digits. Not thinking, your lips part and the taste of rancid cotton candy bathes your tongue when the fingers push past your teeth.
You grimace at the flavor. Bob grins, too wide, terrifyingly wide. Fear renews like a bolt of lightening to the heart and rational thought whirs to life in your pleasure-addled brain.
Pennywise…. He’d called himself ‘Pennywise.’ Where had you heard that before?
“Pennywise was right to save you for later, yes, yes he was. Let you marinate. Let your meat age.”
Pennywise…. Pennywise the clown….
Your heart beats so fast you fear it will burst. Bob’s eyes are jaundiced, wide and wild. Familiar.
The clown. The clown from your childhood nightmares. The clown from the house at the end of the street.
Pennywise.
“And now you see it all, don’t you?” Bob’s voice is a warbled whisper, slow and solemn. “Now you know why.”
More tears burn their way down your cheeks.
“Purpose, hmm?” Bob chuckles, light and airy. “You’ll be of good use to IT.”