Jill Jills 3: The Jillening (NSFW) (Maybe-Semi-Canon)

AN: Jill meets a stranger while out at the club (Yuri, Femdom, Overstim, Squirting, Analingus, Anal Play, Younger Woman/Older Woman, Squirting, you’ve been warned) 

The ice in her glass had long since melted, leaving behind a sad, watered-down bourbon that tasted more like defeat than alcohol. Jill wasn’t drinking it so much as holding it, a flimsy excuse to stay seated, to pretend she wasn’t just clinging to the illusion of winding down. Her body ached, not from exertion, but from the sheer effort of enduring another night that felt like a rerun of every miserable one before it. Her bones felt heavier than they should, her eyelids dry and gritty from lack of real sleep.

She swirled the pathetic amber liquid, the melted ice barely making a sound. The club’s thumping bass wasn’t energizing or hypnotic; it was a dull, grinding pressure behind her eyes, each beat another reminder of how long she’d been running on fumes. Dry spell didn’t begin to cover it. Her body didn’t just feel neglected, it felt abandoned, left to gather dust and cobwebs while her nerves frayed at the edges. She didn’t need sex. She needed to get her guts rearranged, and her poor pussy was aching for something more than a vibe or her fingers.

Of course it was never that easy. She hadn't been dating in months, and she'd been avoiding the bars because, frankly, she didn't want to think she was that desperate. Which was a total lie, she was that desperate, and honestly she wasn't feeling super picky at this point either. So she threw on her tightest tube top and shortest skirt and decided to hit the clubs, for all the good that did her. It was a Tuesday night for fuck's sake, and this place felt more like a morgue than anything else with how empty it was. Or at least, how empty it had been.

“Tough day at the office?”

The voice was a smooth, low alto that cut through the music without effort. Jill turned her head, her professional assessment kicking in before her personal one. The woman leaning against the bar was young, maybe college-aged, and built like a fucking sin. She had a mane of thick, fiery red hair that cascaded over one shoulder like something out of a shampoo ad, but it was the body that did it... that tight, flawless frame poured into a black tank top that clung to her full, high tits and a waist so trim it made Jill’s mouth go dry. Her jeans were skintight, low-slung, and deliberately shredded to show off creamy, toned thighs that just begged to be straddled. Every inch of her screamed heat, sex, and confidence. Her hips had a sway to them that felt weaponized. Her smile was a slow, wicked tease, lush lips parted just enough to make Jill’s clit throb with interest. It wasn’t just attraction, it was gravity, need, desire, and raw, unrefined lust. And Jill... she was caught up in all of it. She never had a chance.

“Something like that,” Jill muttered, turning back to her drink, though her attention flicked sideways more than once. She could feel the heat radiating off the redhead now beside her, that decadent, wicked body close enough to taste. The scent of her shampoo, coconut and smoke, curled around Jill like a lure.

“Looks like you could use a better drink. And better company.” The redhead’s voice held a teasing lilt, like she already knew Jill wouldn’t say no. She flagged the bartender with two fingers. “Two shots of your top-shelf tequila. None of that well shit.”

She didn’t just sit, she glided onto the stool next to Jill, all smooth hips and deliberate pressure as her thigh pressed in against Jill’s. Not a casual touch. No hesitation. Just bold, hot contact that sent a surge through Jill’s lower belly.

“I’m Claire,” she said, watching Jill’s mouth as she spoke.

“Jill.” The name felt small on her tongue. Claire smiled, slow and approving, and when the tequila arrived, she handed Jill her glass with fingertips that lingered just a little too long.

Claire clinked their shots together, her eyes locked on Jill’s like she was watching her undress with her gaze alone. Jill’s pulse skipped. Whatever this was... it wasn’t one-sided.

“To better company,” Claire said, her green eyes locking onto Jill’s. They downed the shots. The liquor was smooth, a fire that spread through Jill’s chest, so much better than the bourbon. Claire’s hand, cool from her own glass, came to rest on Jill’s knee. Fuck. The simple touch sent a jolt straight to her neglected slit. “You have this… intense energy. Like a storm waiting to break. I’d love to see it.”

“Is that so?” Jill’s voice sounded strained. Honestly, it wasn't the best pickup line, but goddamn did she like watching Claire's lips move when she said it.

“It is. My hotel is around the corner. Infinitely better than this dump. We could have a real drink.” Claire’s fingers trailed a hot, deliberate line up Jill’s inner thigh, her touch featherlight but electric. Each inch she claimed left Jill’s skin tingling, her thighs parting on instinct before she even realized it. She stopped just short of Jill’s soaked panties, fingers brushing the damp heat through the fabric, teasing but not pressing.

Jill’s breath hitched, her pulse thundering in her ears. Her panties clung to her now, sticky and wet with arousal, her slit pulsing with want. She could feel herself leaking, practically drooling for more, the ache in her cunt growing thick and urgent. Claire’s touch had lit her nerves like a fuse, and every second without that pressure was an exquisite torture.

“I have a feeling you’re full of surprises, Jill,” Claire purred, her lips brushing the shell of her ear, voice low and smug. “And I want to uncover every. Single. One.”

The walk to the hotel was a blur of smeared streetlights, the pulse of the city lost beneath the roar in Jill’s ears and the lingering, dizzying scent of Claire’s perfume curling in her lungs like smoke. Her pulse was a runaway drumbeat, her core clenching and throbbing with desire, every step a reminder of how badly she needed to be touched again. Needed to be filled. Claimed.

The hotel room was dim, golden, and barely registered before Jill was slammed against the door with a force that made her gasp. Claire’s grip in her hair yanked her head back just enough to bare her throat, while the other hand palmed her ass in a possessive squeeze that had Jill's hips jerking forward, needy and shameless. Their bodies collided like magnets, hips flush, thighs pressing.

“I’m going to ruin you,” Claire growled against her lips, that voice molten and thick with hunger, a sound that flooded Jill’s brain with static and made her entire body throb. “And you’re going to fucking love it.”

Jill whimpered before she even realized she was making a sound, her whole body going limp against the door like a ragdoll under Claire’s grip. Her knees nearly buckled, every nerve ending a live wire, her brain short-circuiting under the heat of Claire’s touch. She felt like she was melting, her willpower collapsing into a puddle of helpless, horny mush. There was no thought left, no resistance, just raw, aching need and a soaked pair of panties clinging to the mess between her thighs. Claire was taller, stronger, and Jill wanted nothing more than to be manhandled, used, and fucked senseless by this absolute goddess who had her completely under her spell.

Claire’s mouth crashed down on hers, devouring her with a hunger that made Jill whimper. This wasn’t a kiss, it was a claim, a brutal, all-consuming dominance that made her melt against the doorframe. Claire’s tongue shoved deep past Jill’s lips, not asking but taking, tasting of tequila and mint and dripping, raw lust. Jill moaned into it, dizzy from the pressure, her fingers scrabbling at Claire’s back like she needed to hang on or be swept under. Her nails dug into the fabric, desperate and trembling, while her pussy pulsed so hard it was like her whole body beat in rhythm with Claire’s mouth.

Then came the bite. Claire sank her teeth into Jill’s lower lip, not enough to draw blood, but enough to shoot a jagged thrill straight to her clit. Jill gasped, her eyes wide and unfocused, brain already starting to short out from the intensity. Her legs wobbled, and every instinct screamed to open herself up further, to be taken. She was already half gone, and Claire was just getting started.

“Get this off,” Claire growled, not asking but commanding, her voice rough with possession as she grabbed Jill’s shirt and ripped it over her head like it offended her. Her bra was yanked down and off in a blur, exposing flushed, heaving breasts that jiggled slightly from the motion. Then Claire’s mouth latched on with a feral hunger, sucking Jill’s stiff nipple so deep her eyes rolled back. Her tongue lashed and circled, wet and relentless, while her teeth scraped just enough to make Jill cry out.

Jill’s head slammed back against the door, her mouth open in a breathless moan. Her knees gave out completely, and Claire had to keep her upright with one arm while devouring her. “So fucking responsive,” Claire muttered into her skin, voice vibrating against her chest. “Yes. I want to hear you scream.”

Claire hauled her toward the bed like she weighed nothing, her grip bruising and authoritative. Jill stumbled, utterly pliant, caught in a fog of lust and obedience. Claire shoved her onto the bed, and Jill flopped onto the duvet, dazed and wrecked already.

Claire didn’t undress like Jill had, all messy, breathless, scrambling. She stood above her, calm and in control, peeling her top off with deliberate slowness, exposing defined abs and full, perfect tits in a lacy bra that looked expensive and deliberately chosen. Her jeans slid off in one practiced motion, leaving her in nothing but black lace panties that were soaked through with arousal. Her pussy bulged prominently beneath the fabric, lips thick and pressed to the seam, the dark patch obvious and obscene.

Jill stared, mouth open, eyes wide, her thighs pressing together in instinctive need. She wasn’t just turned on... she was completely under, unraveling with every second Claire stayed in control. Her breath caught as Claire smiled down at her, amused and approving.

“Good girl,” Claire said, voice low and indulgent. “Already falling apart and I haven’t even started.”

“Look at you,” Claire murmured, crawling onto the bed like a lioness closing in on her trembling prey, her knees straddling Jill’s hips with deliberate dominance. “All flushed and desperate for me. Practically dripping through your panties like a bitch in heat.” Her voice was syrup-slick and smug, layered with approval. She didn’t wait for permission. Didn’t ask. Her fingers curled into the waistband of Jill’s miniskirt and panties and yanked them down in one swift, practiced motion, stripping her bare without ceremony.

The cool air kissed the wet mess between Jill’s legs, making her flinch. She was soaked, so obscenely soaked, her slit glistening, her inner thighs sticky with need. Claire’s gaze locked onto the sight, feral and unblinking, her lips parting in delight. “Fuck, you’re perfect. Look at this cunt... pink, puffy, and begging. All this mess, just from me looking at you.”

Jill whimpered, cheeks flushed, her hips twitching upward involuntarily. She wanted to close her legs, but Claire’s grip held her open, exposed, trembling, and completely at her mercy. Claire didn’t kiss her lips. She leaned down instead and blew a long, slow stream of air directly onto Jill’s clit, watching with satisfaction as it jumped and twitched under the teasing.

Jill jerked, a desperate sob catching in her throat. Claire just smiled, a wicked, beautiful thing, one hand stroking Jill’s trembling thigh with infuriating calm. “Not yet.”

She shifted, lowering her head between Jill’s legs again, her breath ghosting over slick, swollen folds. Her tongue was flat and firm, dragging another slow, deliberate stripe from Jill’s entrance to her clit. Jill bucked off the bed with a strangled cry, her whole body tensing.

“None of that,” Claire chided, her tone sweet but cutting, breath steaming against Jill’s soaked cunt. “My name. Say it, beg for it, or you get nothing.” Then she dove in.

Her mouth was merciless. She didn’t just eat Jill out, she devoured her, sucked her lips into her mouth and moaned like she was tasting the divine. She circled the rim of Jill’s pussy, tongue teasing without satisfying, keeping her right at the precipice. When she finally moved to her clit, it was with maddening precision, her tongue tracing tight, torturous circles before sucking hard, drawing a scream from Jill’s throat.

But she stopped. Again.

Jill cried out in frustration, hips humping at the air, a sob catching in her chest.

Claire looked up at her, chin wet, eyes gleaming. “You’re going to come when I say. And not a fucking second before.”

The teasing continued. Claire brought her right back up, her mouth relentless, then backed off just as Jill began to tremble. Again. And again. Jill writhed, sobbing now, clenching fistfuls of the sheets like they were the only thing keeping her grounded.

“Claire,” she begged, voice ragged and high. “Please. I can’t-I need to-please!”

Claire’s grin was pure sin. She pressed two fingers to Jill’s dripping entrance and slid in without resistance, curling just so, while her mouth returned to Jill’s clit with a low growl.

“Come,” Claire commanded, her voice dark and electric, vibrating against Jill’s swollen, trembling clit. “Come all over my face, you desperate little thing. Now.”

Jill shattered.

The orgasm ripped through her like a live wire, her body arching with brutal force, a scream torn raw from her throat as her pussy clamped down and gushed in wet, hot release. Claire’s chin, her lips, the sheets... it was everywhere, a flood of soaked lust dragged out of her by pure domination. Jill’s legs kicked, her fingers clawed the bedding, but Claire didn’t let up. Her mouth stayed locked to her clit, tongue dragging through every spasm, drinking her in like she was starving.

And then Claire drove her fingers in, hard. Three now, not two, plunging deep and curling up to wreck her from the inside. Jill’s hips bucked wildly, another wave surging up before she’d even finished the last. Her cries broke into helpless, shattered whimpers, her body locked in place as Claire railed her cunt with practiced brutality.

“Look at you,” Claire growled, lifting her mouth only long enough to speak. “So fucking wet, so ruined, so mine.” Her thrusts didn’t slow, knuckles slapping against Jill’s soaked folds with obscene, wet sounds. “You’re going to come again. You’re going to scream for it. Beg if you want mercy, and I won’t give it.”

Jill was beyond thought. Her mouth worked but no words came. Her cunt was a burning, soaked mess around Claire’s pumping fingers, her thighs trembling uncontrollably. When the next orgasm hit, it was a collapse. A surrender. She screamed herself hoarse, body flailing, soaked again and again, utterly dominated, every ounce of control wrung out of her and fed into Claire’s hands.

As the last shudders wracked Jill’s body, Claire’s tongue went right back to work on her oversensitive clit. Jill screamed, a sound of pure shock and sensation. “No! Too much! Claire, please, it’s too sensitive!”

“I know,” Claire purred, not lifting her head. Her fingers joined her mouth, two slipping easily into Jill’s sopping cunt, crooking against that spongy spot inside. The pleasure was still there, but now edged with a sharp, almost unbearable intensity. Jill thrashed beneath her, overwhelmed, sobbing from the overstimulation. “That’s it. That’s your body learning who’s in charge. You can take it. You’re taking it so fucking well.”

Jill’s protests dissolved into breathless, broken sounds as a second, sharper climax was coaxed out of her with ruthless patience. It left her shaking and open, the last scraps of resistance falling away as she yielded to the hands and voice guiding her.

Before the sensation had fully settled, Claire was already in motion, turning Jill onto her stomach roughly. A pillow slid beneath Jill’s hips, lifting her. The shift felt like an order she was grateful to obey. Cool air skimmed fevered skin while Claire’s gaze swept over her with ravenous focus that promised more. Jill lay bared to that hunger, trembling and ready, surrender shaping her body while Claire’s intent pressed closer to claim every inch.

“What a perfect fucking ass,” Claire groaned, her voice thick with want, as she brought her palm down in a sharp, stinging slap that bloomed into a deep, thrumming heat. Jill moaned into the duvet, the sound needy and helpless. Another slap landed harder on the other cheek, the crack echoing in the quiet room. “Begging for it,” Claire praised, breath quickening as her thumbs spread Jill open, exposing the tight, hidden pucker and the slick sheen below. “And this… fuck, Jill. This pretty little starfish is mine tonight. Present it. Be a good girl and show me.”

Jill felt the hot, wet flat of Claire’s tongue trace a path from her soaked slit up to her asshole, tasting everything in a single, greedy sweep. She flinched, the intimacy filthy and perfect, a lightning jolt ripping through her spent muscles. Claire spit directly on the tight ring of muscle, the cool splash making Jill gasp. “Relax,” Claire ordered, firm and indulgent. “Breathe out for me. Open up for my tongue.” She pressed the tip to the pucker, insistent and steady, and waited for that tiny give, then pushed inside, shallow at first, claiming inch by inch as Jill panted and trembled.

The sensation was bizarre, invasive, and dizzying with heat. Jill buried her face in the mattress and moaned, her hips tilting up in pure submission. Claire ate her with slow, demanding precision, lapping and plunging, circling the rim before spearing her again. She hummed in pleasure at the taste, fingers dimpling Jill’s cheeks as she held her open. “That’s it,” she coaxed, voice rough with hunger. “Take my tongue. Push back for me.” Jill obeyed without thought, rolling into each slick stroke, melting into a puddle of horny need while Claire explored her, tasted her, and made her stay open and wanting for more.

Claire pulled back. Jill heard the snap of a cap and the soft squeeze of a bottle. Lube. A cool, slick bead landed on her tight ring, then a finger circled and pressed. “Now, easy,” Claire instructed, patient and in command. Jill breathed out and opened, and Claire’s finger slid into her ass in one smooth, burning glide. “Perfect... So tight. Taking my finger so good.”

The stretch was so satisfying, a full, aching pressure that made Jill shake. Claire set a steady rhythm, working that finger in and out, owning Jill’s body with calm, unhurried strokes until the burn mellowed into deep, drugging pleasure. Just as Jill started to adjust, a second finger joined, the shock of it a sharp flare that melted into thick heat. Claire’s other hand slipped under her, found Jill’s dripping cunt, and ground firm circles over her clit like she was dialing up a response she already knew by heart.

The double use was too much. Jill broke with a ragged scream, clenching around the fingers in her ass as wet gush soaked Claire’s hand. Claire rode her through it without mercy, pace never wavering, crooning praise into the small of her back.

“Again,” Claire ordered, voice hoarse with hunger. “You’re not done. Come again.” She scissored inside Jill’s ass, stretching her impossibly wider, then drove in deeper, her thumb bearing down hard on Jill’s swollen clit. “Open for me. Take me. Be good and take it.”

Jill’s world narrowed to the pistoning of Claire’s hand and the relentless grind at her clit. Her body was no longer her own. It was an instrument and Claire was playing it, dragging a raw symphony from it, note after filthy note. A second climax tore through her, weaker but just as blinding, leaving her trembling and wet-faced against the sheets, used and grateful.

“Good girl,” Claire breathed, slick fingers never leaving her. “Now give me the rest.” She added another pulse of lube and hammered Jill’s ass in hard, relentless strokes, knuckles meeting slick flesh with obscene sounds while her palm rode Jill’s clit. Jill sobbed and pushed back, helplessly meeting every thrust. Pleasure stacked and tipped, then crashed. She came hard, entire body seizing around Claire’s thrusting fingers while a hot spill soaked her thighs.

Claire eased her down only to wind her back up, using Jill like a toy, taking her ass over and over until Jill’s voice was gone and her legs shook. When the final wave broke, Jill collapsed boneless, whimpering into the duvet, nerves sparking with aftershocks as Claire’s hand gentled and withdrew.

Warm lips pressed to Jill’s ear. “That’s mine now,” Claire whispered, satisfied and possessive. “And we’re not finished.”

The room blurred to heat and shadow, the rhythm of Claire’s breath and the slow rake of her nails the last things Jill felt as the world slid into dark. Somewhere in that fade, Claire’s promise followed, soft and certain, making Jill shiver.

000

The walk of shame fit like an old, hated coat as she slipped out into the gray wash of dawn. Her shoes dangled from two fingers, her stockings rubbed where her thighs still felt tender, and Claire’s shampoo clung to her skin like a ghost. The note on the duvet had been neat and cocky, clean up and call me, punctuated with a red kiss that marked her like a brand. The number burned in her pocket with every step. She told herself it was a mistake, a wet, hot, messy lapse of judgment, then winced at the word because her body did not agree. Her mouth still tingled where teeth had caught her lip, and the ache low in her belly left her quivering when she thought about how it got there.

She kept replaying the parts she shouldn't keep replaying, the way Claire told her to open and she did, the way her praise slid under her skin and unplugged something she had kept sealed for years. She had never thought of herself as submissive because Jill Valentine didn't submit to anyone, not on the job, not in her life, not in her head.

Yeah, right, she thought bitterly. The truth of it left her blushing red when she tried to beat it down, bright as the tender marks on her neck and the stiffness in her thighs. Every few blocks she caught herself squeezing her legs together, as if that would quiet the heat, as if that would stop the memory of a hand directing her and the relief of obeying it.

Fine, she thought, later. Shower first, coffee second, new clothes third, then the small mercy of an afternoon shift where she could hide behind her paperwork. The number stayed where it was because she wasn't stupid enough to throw it out and not honest enough to admit she was looking forward to another... session. She told herself she wouldn't call, then admitted she probably would, then told herself that decision belonged to the version of Jill that lived in the future because Present Jill was too tired to worry about it. For now she walked, shoulders hunched against the tired morning, and promising nothing to anyone but the door of her apartment and the bed waiting on the other side.

Cleaned up and composed as best she could be, Jill made her way into the Raccoon Police Department. The fluorescent lights buzzed, and the lobby coffee smelled burnt. A headache pulsed behind her eyes, and the tender pull in her thighs reminded her of everything she was determined not to think about.

She rounded the corner toward the STARS office and stopped short. The mysterious redhead stood beside her coworker and fellow STARS member, Chris Redfield, looking infuriatingly at ease.

“Oh, cool. I was hoping you’d pop in before I had to take off. This is Claire, my kid sister. She’s visiting from out of town for the week.”

Chris said it cheerfully, oblivious. Jill watched Claire’s eyes light with mischief and recognition and began screaming internally.

“Claire, this is Jill Valentine.”

With a wicked, gleeful smile, the redhead met Jill’s gaze.

“We’ve met.”

AN: Why do I keep doing this to myself? This one super got away from me and basically turned into an all day sort of thing.  Yes I am aware Claire is 18. Fake IDs are a thing and she has that wild child vibe so whatever. This one absolutely was a hell of a ride writing, not gonna lie, because subby Jill seems to be my thing and I’m just gonna roll with it. I also wanted to have the possibility of a sequel because, well, this one managed to stir my creative juices and not like that you perverts. Honestly writing porn is fun sometimes, just as a little departure from the usual deep drama I seem to be hooked on.

I have no regrets, heh.

Come check out my >PATREON!< if you wanna see more TTN stuff, including the next two chapters coming up. Seriously. Please? I need you! I want you! Oh baby, oh baby.