That Was Not A Try | Regina George x Reader
Smut: kinda overstim, dubcon if you squint, multiple orgasms, seven minutes in heaven, alluded bullying, hair pulling, gp reader
The party buzzed with loud music and laughter, but Regina’s sharp gaze cut through the crowd the moment she spotted you. She had invited you specifically for this, her favorite nerd to pick on, the quiet girl who always flushed under her bullying.
Your casual pants and shirt felt out of place among the party outfits, and Regina’s short skirt swayed as she approached with that mocking smirk.
"Look who showed up. The little bookworm. Hope you’re ready to get humiliated tonight, nerd," she sneered, giving your shoulder a shove before spinning away to join the circle.
Everyone gathered for spin the bottle. Your hands shook as you reached for the bottle, heart hammering. It spun wildly before slowing and stopping dead on Regina. The room erupted in whoops and whistles. Regina’s eyes narrowed, but her lips curled into a cruel grin.
"Let’s go, loser," she ordered, grabbing your wrist and yanking you toward the small room.
The door clicked shut behind you both, plunging everything into near-darkness lit only by a thin strip of light under the door.
Regina leaned back against the wall, hiking her skirt up slightly with one hand. "Fuck me," she commanded right away, voice low and demanding. "Right now. Don’t be fucking useless."
You froze, cheeks burning. "N-no, I can’t. I don’t know how. I’ve never… I’m sorry, I just—"
"Fuck me," she repeated, stepping closer and pressing her body against yours. Her hand slid down to cup the front of your pants, feeling the growing hardness there. "Don’t play shy. I know you want it. Take your clothes off and fuck me."
"I really wouldn’t know what I’m doing," you whispered, voice trembling. "I’ve never done it before."
"Then learn fast," Regina snapped, tugging at your waistband. "Fuck me, nerd. Now."
Her relentless commands wore you down. After two minutes of her hissing the same order while grinding against you, your shyness cracked.
You fumbled with your pants, freeing your cock. Regina hiked her skirt higher and shoved her panties aside, exposing her pussy. You lined up awkwardly, pushing in with a shaky thrust.
"That’s it," Regina hissed, gripping your hips. "Fuck me harder."
You moved, inexperienced and clumsy at first, but the tight heat around your cock overwhelmed you fast. Within moments you gasped and came, pulsing deep inside her with a soft moan.
Regina smirked, expecting exactly that. "Figures. Quick shot nerd."
But you didn’t pull out. "I… I have to go again," you said quietly, already starting to thrust once more. "You didn’t cum. I need to make you feel good too."
"No—wait," Regina started, surprised as your renewed movements hit deeper, rubbing spots that made her breath hitch. Her hands pushed at your shoulders at first, but the sensation built fast. She stopped resisting, legs wrapping around you. "Fuck… keep going."
You kept thrusting without pause, your cock still hard inside her. Regina’s breathing turned ragged right after her first climax, her thighs twitching around your waist as the aftershocks rolled through her. You slowed just enough to let her catch a breath, then angled deeper again, grinding against the spot that made her hips jerk.
Her hands slid up your back, fingers curling into your shirt as the pressure built once more. Little gasps escaped her with every thrust, her pussy growing slicker and tighter around you.
The second orgasm crept up gradually—her moans turning into a broken whimper, her legs locking tighter, until her whole body seized and she came again, walls pulsing hard.
You didn’t give her time to recover. You kept moving, slower at first so she could feel every inch sliding in and out, then picking up speed when her breathing evened out.
Regina’s head tipped back against the wall, mouth open, eyes half-lidded. Sweat beaded on her neck.
You shifted your angle again, hitting a new spot that made her breath hitch sharply. Her fingers dug into your shoulders as the tension coiled tighter inside her. She tried to speak, but only a shaky moan came out.
The third orgasm built over the next minute, her hips rolling to meet your thrusts, her pussy fluttering around your cock before she suddenly clenched and came hard, her body shaking as pleasure crashed through her.
Still buried deep, you kept a steady rhythm, letting her ride the afterglow before pushing her higher again. Regina’s legs trembled around you. Her skirt was bunched up between your bodies, her panties stretched aside.
You could feel her getting wetter with every stroke, the wet sounds filling the small space. Her hands moved to your hair, tugging lightly as the next wave started to rise. She bit her lip, trying to stay quiet, but soft whimpers slipped out anyway.
The fourth climax took longer to build—her breathing growing faster, her thighs squeezing you, her pussy gripping tighter and tighter until she finally broke, coming with a choked cry, her body going limp against the wall as the orgasm left her panting and spent.
The door rattled. Time was up. You both scrambled to fix your clothes. Regina smoothed her skirt and hair, face flushed and speechless for once. Beside her, you tugged your pants up, rambling nervously.
"I’m sorry if I didn’t make you cum, I—I really tried my best, but I didn’t know what I was doing. Maybe I can find books or watch something to learn better positions or—"
"Whatever," Regina cut in, voice still shaky. "Meet me in my room after the party, nerd."
The party continued in full swing once the seven minutes ended. Music thumped through the house while people laughed and drank in every room.
Regina stepped out first, her cheeks still flushed, skirt smoothed down and hair quickly fixed. She gave the group a sharp look that dared anyone to comment, then headed straight for the kitchen to grab another drink.
You followed a moment later, heart still racing, trying to act normal as the circle of players teased about the closet time. Someone spun the bottle again and the game moved on without either of you.
Regina stayed on the opposite side of the room for a while, talking loudly with her friends, but her eyes kept flicking toward you.
Every time your gazes met she looked away fast, sipping her drink like nothing had happened.
Later you spotted her near the stairs, leaning against the wall while two guys tried to flirt. She laughed at something one of them said, but her posture stayed stiff.
When you passed by to get more snacks she reached out and caught your wrist for half a second.
"Meet me upstairs in ten minutes," she muttered under her breath, voice low so no one else heard. Then she let go and turned back to the guys like the exchange never occurred.
The rest of the night blurred with loud music and constant movement. You caught glimpses of Regina circulating through the crowd, always surrounded by people, yet she never stayed in one spot long.
Around midnight she disappeared up the stairs without looking back. A few minutes later your phone buzzed with a single text from her, "My room. Now."
By the time the party started winding down, most guests were either passed out on couches or still dancing in the living room. Regina's bedroom door stayed closed upstairs, the light visible under the crack, while the noise downstairs slowly faded into background chatter.
The bedroom door clicked shut behind you, muffling the distant thrum of the party downstairs. Regina stood by her dresser, arms folded, her skirt still hiked up from your earlier encounter. She looked you over with a sharp, predatory expression that made your stomach flip.
"Took your time," she said flatly. "Get over here and fuck me again. Now."
She turned without waiting, bending over the dresser edge and lifting her skirt to expose her wet, waiting heat. She glanced back over her shoulder, her eyes narrowing. "Pants down, nerd. Hurry up."
You stepped up behind her, still unsure of what you’re doing really, hands trembling as you freed your cock and pushed inside her pussy. The immediate heat and tightness made your breath catch in your throat.
You started thrusting, gripping her waist for balance, but as the friction built, your fingers slid up and tangled in her hair. You gave a quick, instinctive tug before yanking your hand away as if you'd been burned.
"Shit, sorry!" you blurted, your voice shaky. "I didn't mean to pull your hair, I just—"
"God, shut up," Regina snapped, though her fingers dug violently into the wood of the dresser. Her pussy clenched around you in a rhythmic squeeze. "Stop flopping around back there. Do better."
You adjusted your angle, driving deeper and trying to find a steady rhythm. Your hands wandered again, unsure where to rest, eventually pressing down on her lower back to hold her steady.
As your hips snapped forward, Regina’s body jolted. She bit her lip hard, a muffled “Mmph!” escaping her nose as she fought to keep her composure.
You whimpered, pressing a little firmer. "I just... I don't know where to put my hands."
"Pathetic," she muttered, though her voice was tight and strained. She swallowed a gasp as your cock dragged along her sensitive walls.
The challenge sparked something in you. You pulled out and guided her onto the bed, rolling her onto her side with one leg lifted. You slid back inside from behind, holding her close. Your hand drifted up again, catching her hair in another light tug. You froze, immediately letting go.
"F-fuck, Regina... I'm sorry. You feel so good, I can't help it," you murmured, your cheeks burning.
"Useless nerd," she hissed, though her thighs were visibly trembling. "You call this fucking? Put some effort into it."
Your thrusts grew more insistent, more desperate. When Regina tried to shift forward to escape the intensity, you pressed your hand firmly between her shoulder blades, pinning her to the mattress. She squirmed, but the pressure only seemed to drive you deeper.
You gasped, easing the pressure slightly. "I wanna make you cum."
"Shit... that's... not terrible," Regina forced out. Her voice cracked, and a sharp, airy moan slipped past her lips—“Ah!”—before she quickly clamped her mouth shut, looking horrified that she'd made a sound.
You flipped her onto her back, spreading her legs wide and plunging back in. Your hand landed on her stomach, pinning her down as your pace accelerated.
Regina's back arched, her chest heaving. Every time you hit the sweet spot, her composure fractured further. A low, guttural hum vibrated in her throat, and a soft, broken whimper escaped her.
"Fuck, I-," you murmured, pressing down firmer when her hips bucked. "I'm trying to be careful. 'M sorry."
"Deeper," she ordered through clenched teeth, her eyes fluttering. "God, you're so... nggh... clumsy."
The friction was becoming unbearable. You felt the pressure building, a sudden, violent surge that you couldn't control. With one deep, heavy thrust, you groaned and came hard, filling her pussy with a hot load of your cum.
"Oh god, fuck! I didn't mean to—I'm so sorry, oh, you feel...so good!" you gasped, your heart racing.
Regina stiffened, her eyes widening as she felt the warmth flooding her. She let out a sharp, strangled gasp that she couldn't catch in time. "You... fucking shut up... you just—" She stopped, her breath hitching. "Don't stop. Just keep going."
You didn't have time to recover before you were moving again, the lubrication of your own cum making the sliding sensation even more intense.
You bent her back over the edge of the bed, fucking into her from behind. Your fingers found her hair again, tugging firmly this time, now not letting go.
"I'm trying to hold back, but you're so tight..." you panted.
Regina was losing the battle.
The sharp-tongue was being eroded by raw pleasure. As you fucked into her, a loud, unrestrained moan ripped from her throat—“Oh god, yes!”—followed immediately by a frantic, "fuck, fuck, fuck, fuck—like that!"
The sound of her breaking only made you push harder. You were blinded by the sensation, your movements becoming rough and primal.
Another surge hit you, unexpected and overwhelming. You bucked against her, spilling inside her for the umpteenth time, the force of it making you shudder. "I'm sorry—I'm so sorry, I can't help it!" you cried out, breathless and panicked.
Regina didn't snap back this time. She couldn't. She was shaking, her face pressed into the sheets, her voice breaking into short, desperate exhales. "Just... fuck... just keep... nnngh!"
You didn't stop. You kept thrusting through the climax you don't even realize she's having, your cock sliding through the mixture of her juices and your cum.
Regina came hard, her whole frame shuddering under your grip. She let out a long, high-pitched wail of pleasure that echoed through the room, her composure completely shattered.
As the waves of her orgasm subsided, you felt one final, lingering pulse of pleasure. You groaned, coming inside her a third time, your body collapsing against her back.
"Did... did you cum?" you whispered into her neck, exhausted and still trembling.
Regina lay there, breathing hard, her skirt rumpled and her face flushed. She didn't call you pathetic this time. She just let out a shaky, exhausted sigh, her body still twitching from the intensity of the encounter.
As you received no response, you took it upon yourself to obscenely take a look for yourself. You flip Regina onto her back and lift her leg up as she pants above you, observing how her pussy and leaking mainly of your cum.
Guilt swallowed you. It was as if you'd only used Regina to get off and didn't even bother to make her feel good and return the favor. You simply could not let it stand.
"You didn't cum, " you thought out loud. "I—I can try again, Reg— I'll do better, hold on."
You stroke your cock twice and line up your cock to her pussy again before slipping in. The heat of her pretty pussy envelopes and overwhelms you. You will yourself not to cum so soon, but like all the other times before, you can't help it.
Regina groans, her brows knitting together as she squirms under you and grabs onto you as she bucks her hips up to take more of you.
"Shit, I'm sorry...I—I'm so bad at this." You shudder and press into Regina deeper as your load shoots into her. You pant above her and hold onto her shoulder
You stayed locked inside her, hips driving forward without pause as your cock kept pulsing thick spurts of cum deep into Regina's pussy. The desperate need to push her over the edge again fueled every thrust, your body pressing down harder to keep her exactly where you wanted.
You shifted her onto her side first, one leg hooked over your arm to spread her open, then rolled her fully onto her stomach again. Your full weight came down across her back, pinning her flat to the mattress while your knees kept her thighs apart.
Your hands caught both her wrists and yanked them up above her head, holding them tight against the sheets so she couldn't push back or twist away.
Your cock never stopped moving, slamming into her soaked cunt from behind with wet, sloppy sounds as more cum flooded out around your shaft.
Every thrust forced another heavy spurt from you, soaking her insides and leaking down her thighs in messy trails. Regina's body jolted under you with each impact, but she stayed trapped, face buried in the bedding, ass raised just enough for you to keep pounding into her.
"Sorry," you gasped, voice shaky from the constant release pouring out of you. "Oh my god, Regina, you feel so fucking good. I want you to cum, please."
Your grip on her wrists tightened as another wave of cum erupted inside her, yet your hips never slowed. You kept driving deeper, grinding against her most sensitive spots while your body stayed flush against hers, refusing to let her shift even an inch.
Regina's breathing turned ragged fast. At first she tried to bite back any sound, but the relentless pace wore her down. A sharp moan slipped out, then another, louder.
"Fuck—ahh, shit!" Her voice cracked open completely as your cock dragged against her walls with every stroke. "Jesus Christ—don't stop, fuck!"
The moans poured out now, raw and unrestrained while her body shook under your pinning weight. She couldn't hold anything back anymore.
You kept thrusting through it all, cum still spurting in thick ropes as you chased her pleasure. "Fuck, okay." you moaned when her voice pitched higher, hips snapping harder.
"A—are you cumming?" Regina's moans turned into broken shouts, her pussy clenching tight around your still-ejaculating cock as another orgasm ripped through her.
You don't register it, just kept fucking her relentlessly, driving her straight toward the next one while your cum kept leaking out around your shaft.
"Fuck yes—ahh, god!" Regina cried out, voice hoarse from how loud she had become. Her body jerked helplessly but stayed completely immobilized under you.
You pressed down firmer on her wrists, legs spreading hers wider, your cock buried deep and pulsing nonstop as you refused to ease up even for a second.
You kept pounding into her, grinding deep with every stroke while your body stayed flush against hers, refusing to let her shift even an inch.
Regina's breathing turned ragged fast. The pressure built quick under your pinning weight. Another climax hit hard—she clenched tight around your cock, her whole frame shaking as pleasure ripped through her.
Another followed close behind. Her body seized under you again, legs trembling helplessly as another wave crashed through her.
"Ahh—god, fuck yes!" Regina cried out, voice hoarse now, completely lost in it.
You didn't register either one. You just kept fucking her, driven by that desperate need, your cum still spurting thick and hot with every thrust.
You stayed locked in that pinned position, body pressing her flat, wrists held tight, cock slamming deep over and over.
Her cunt pulsed hard around your shaft, juices mixing with all the cum leaking out of her. "Nngh—shit, fuck!" She couldn't hold anything back anymore, body jerking under your weight.
The fourth climax hit her even harder—her voice broke into frantic moans, curses pouring out between gasps as her pussy clenched and fluttered around your cock.
"Fuck—ahh, don't stop!" She moaned out, loud and desperate, completely overwhelmed.
You kept going, hips driving forward relentlessly, another thick spurt of cum flooding her as you chased her pleasure without pause.
Regina's body shook under you, pinned and trapped, her moans turning into broken shouts with every thrust.
The fifth orgasm built fast—she clenched tight again, her voice cracking into a raw scream of pleasure as it hit her. "Jes—fuck, yes!"
You didn't ease up. You kept pounding into her, your cum still pouring out in heavy spurts, your body locked on top of hers with no room for her to move.
Then the tension snapped for both of you at once—your cock erupted harder than before, thick ropes of cum blasting deep inside her while her pussy clamped down in a powerful sixth climax.
Regina's whole frame convulsed under you, a loud, cursing moan tearing out of her as pleasure crashed through both of you together. "Fu—ahh, god!"
You stayed buried deep, hips still twitching with aftershocks, your cock pulsing out the last of your release. But the drive didn't fade. You started moving again, slow at first then picking up speed, already chasing another one for her.
Regina's voice came out frantic, shaky and breathless. "Wait—stop, I already came! Fuck, I came so many times already—I'm overstimulated, please!"
She tried to twist under your pinning weight but couldn't move much, her wrists still trapped above her head. "I already came—multiple times! You don't have to keep going!"
You freeze instantly at her frantic words, hips stuttering to a halt while your cock stays buried deep inside her cum-soaked pussy. Your body stays pressed flat over her back, pinning her wrists above her head, but the relentless thrusting stops cold.
"Wha—wait, really? Fuck, okay—I'm sorry...I— Did I hurt you?" Your voice comes out shaky and confused, breath hot against her ear as you hold completely still.
Regina pants hard underneath you, her body still twitching from the overload. "No, you didn't hurt me, you idiot. I came. Multiple times. I'm overstimulated as hell and you wouldn't stop."
You slowly ease your weight off her, releasing her wrists and rolling to the side so she can breathe easier. Your cock slips out of her with a wet sound, thick cum leaking from her pussy and dripping down her thighs onto the sheets.
"Oh my god, I'm so sorry. I didn't realize—I just wanted to make sure you felt good. You were so loud and I thought..."
She pushes up onto her elbows, skirt still bunched around her waist, hair messy and face flushed. "You kept going even after I came the first time. Then the second. Third. I lost count after that."
"I really didn't know," you mumble, sitting up and fidgeting with your hands. "I was trying so hard to get you there. You feel amazing and I just... kept cumming and wanted you to cum too."
Regina sits up fully, adjusting her skirt with shaky hands. "Look, nerd, it was fine. You're okay. But we're done now."
"Did you... did you actually enjoy it?" you ask quietly, voice small. "I mean, I know I was pulling your hair a lot and holding you down, and the that might not be something you're into, but—"
"It was good...or whatever," she admits, voice tight. "It's fine for someone like you."
Her expression shifts fast—embarrassment flashing across her face before anger takes over. She stands up abruptly, smoothing her clothes and pointing at the door. "Get out. Now. The party's over for you."
"Regina, I—"
"Out," she snaps, cheeks burning red. "Before I change my mind about how good that actually was."
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I feel like this doesn't make sense
