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You never liked to be classified as a mean girl, but you could admit that this was definitely mean girl behavior. It was one thing to talk about someone, but to go as far as make bets on them. Especially regarding the size of their you know what. Either way, a bet was a bet, and something told you that you would be the one taking all the money home tonight.
“I didn't really think you were a party guy.” You told Jonathan as you applied a fresh layer of lip gloss before rubbing your lips together.
“Oh, I promise you, I’m not.” He says, eyes flickering between yours and your lips. “I just uh- I guess I wanted to try to get out of my shell a bit.”
He gives you a soft nervous smile, clearly unsure where to keep his gaze. He says something else, but his words drown in the roar of the party. Leaning in, you brought your hand to his shoulder, allowing him to instead say it into your ear. Before he spoke, you heard his breath hitch and heard him gulp. Hook, line and sinker.
“W-what about you?” Jonathan asks, not wanting the conversation to end.
Carefully your hand moves to the back of his neck, he allows you to bring his head lower, so you could easily speak into his ear. You take the opportunity to let your fingers comb into the hairs at the back of Jonathan's head. The feeling drags a noise out of him before it's quickly covered with a cough.
“I guess you could say I’m the same way. My friends are the real party girls, and sometimes I just tag along.” You told him, fingers playing in his short hair. “Can I ask you something? It's like really loud in here, and you seem ten times more interesting than anyone here. Do you mind if we find a quiet place to talk?”
Jonathan looks at you for a moment before responding. He was unsure if you were being serious or not. It wouldn't be the first time a pretty girl had teased him in this way. Narrowing your eyes, you scanned his indecisive expression before leaving him to think about your question. He watched you as you made your way to your friends. Once you did, they all looked to Johnathan, and the nerves in his body turned his stomach. In worry? In excitement?
Either way, when Jonathan saw you making your way back to him, he swallowed his nerves and bit the bullet. The two of you searched the crowded house for an empty room, and the nerves Johnathan had tried to suppress were quickly rising. He couldn't tell if it was all the people, their comments, their crude facial expressions. Or if it was you. Eventually an empty room was found and the two of you were finally alone.
Of course, before anything could happen, you needed to ease Jonathan into it. You knew boys like him, the silent sweet type, probably definitely inexperienced. Most people think they shy away from sex, but you knew it was the opposite. All that lack of attention would build and build, so the moment they had a chance to let it out they'd take it. Thankfully, talking with Jonathan was actually somewhat fun, and what came after was surprisingly incredible.
“And the underdeveloped film can't be exposed to light”
“Uh huh.” You nodded, clearly not paying attention.
Or at least not paying attention to what he was talking about and more so the way he was talking about it. He spoke so passionately and intensely about his interest. Even going as far as to set his drink aside when the muscle memory in his hands started to kick in, mirroring what you could only assume was him holding film or his camera. He continued to talk, not yet noticing the way you were inching closer to him.
“because it ruins the pictures.”
“Uh huh.” You tilted your head to the side. “Of course it does.”
“And it uh almost ruins the possibility of it developing c-correctly.”
The realization slowly creeps up on him and Jonathan's eyes are back flickering between yours and your lips. Your deep brown eyes and long lashes. Your beautiful brown and pink lips shining with gloss and shimmering with glitter. He bet they were soft, very soft and tasted like whatever flavor gloss you were wearing. God, he couldn't wait to know what they tasted like.
“Can I ask you something?”
He nods eagerly.
“Can I kis-”
Jonathan waste no time, his lips crashed into yours, and it's clear now how pent-up he really his. He kisses you anxiously yet desperately. Desperate to feel your touch. Yet nervous to feel you. He forces his hands to stay on his knees balled into fist, daring to break free.
Poor thing, god, he really had no idea what he was doing
Thankfully, though, you did. Taking his hands into yours you guided them to your side erasing whatever space was left between the two of you. He quickly adapts to the feeling, gently squeezing and massaging your body. His fingers press into your skin, daring to pull you even closer before hesitating and pushing you back. His desperation and nervousness fighting back and forth.
Wrapping your arms around his neck before swiftly climbing on top of him, Jonathan's mouth clung to yours. His hands slid to your hips and Jonathan's grip tightened. He pulls you into his lap, squirming at the pressure your body brought. A muffled sound leaving him as your body meets his. A moan ? A whimper ?
Regardless of what it was, it wouldn't be the last sound to leave the very needy boy. Soon both of your clothes were discarded on the floor, leaving the two of you in your underwear and Jonathan with a new-found confidence. He roamed around your body more freely. His eyes, his lips, his hands. Venturing over your chest, neck, collarbones and clothed clit, taking in all and every inch of you.
“F-fuck, Jonathan, just like that.”
The palm of his hand slides up and down against your aching clit. He teases you the same way he'd tease himself. Deep and rough. You shudder at his touch, chuckling through shaking gasps and moans.
“Do you like that?” Jonathan asks between deep breaths hoping, praying that you did.
Your teeth sunk into your bottom lip, and quickly you nodded. Jonathan's eyebrows pinch together, and he holds himself back, copying your actions as little sounds slipped from both of your lips. Jonathan continues his actions focusing solely on you and your pleasure, his middle, and index fingers pull the fabric of your underwear aside. He presses his palm harder against your clit, moving in tight close circles as his fingers dip inside of you. You gasp and move your hips forward, pushing them deeper inside of you.
“Fuck.” You moaned body buzzing.
Rocking back and forth you rode Jonathan's hand. Losing yourself in the combined pleasure of his palm and fingers. You were close and even he could feel it. The way you tighten and soaked his fingers. The way it ran down his hand he could cum just from seeing you be this undone. You were unraveling right before his eyes and Jonathan was loving every second of it.
Your climax came and went taking all your energy and restarting your stamina. With shaky legs you climbed off Jonathan and planted your self on the bed. You expected him to join you immediately to finish what the two of you had started. But instead Jonathan found himself a bit preoccupied cleaning his fingers of your cum.
You chuckled to yourself at the realization before pushing off the bed. You wrapped your arms around him, you rested your head on his shoulder feeling a bit sentimental. Knowing that although you were doing this with ulterior motives Jonathan wasnt. You pressed to his jaw whispering sweet nothing's to him. Hoping that he’ll remember your words and remember this moment as something sweet.
“I want you.” You said softly. “I want you to fuck me Jonathan.”
He gasped under his breath, and you smiled a mischievous grin. Slowly you brought your hand to his lap teasing Jonathan over the fabric of his boxers. Focusing entirely on the dark spot his pre-cum had created. Circling the damp area in tight slow motions. He squirms from your touch little whimpers leaving him as he shifted.
He nodded immediately, and his lips desperately found yours. You were both swift. Removing the few pieces of clothing still left on your bodies and laying on the bed. From there things went on how they always did until they didnt. It happened so quick you almost didnt notice the change at first. One moment Jonathan was praising you and your body and the next he was doing the opposite to himself.
“Oh god you feel so fucking good.” He moaned. “am I as clueless as you were hoping?”
The words slipped through the cracks of your mind. You were too overwhelmed with the creeping feeling of over stimulation. Your last orgasm mixing with the one that was now quickly building.
“Huh is it as small as you expected?” Jonathan spoke again with steady thrust yet this time you caught it.
“Wha-?” You questioned him mind hazy.
“This is what you wanted right? To see what the weirdo had in his pants to see how little he really was just say it.” Jonathan persisted voice shaking. “Say it just say it please.” He begged dropping his steady pace for a speedier sloppier one. “Please just say it.” He whimpered your name.
His hips snapped against yours deeper and faster Jonathan worked you both. Again and again he continued building and building your climax while holding his back. A familiar feeling spread across the bottom of your stomach and as your second orgasm took over your body Jonathan quickly pulled out. His hand met his shaft furious pumps of his fist spray thick white ropes across your skin. He moans weakly prolonging his climax until it was too much for him to handle. Jonathan collapses atop you and his knowledge of you and your friend's antics becomes crystal clear.
“I hope the moneys worth it.” He huffed pushing himself off of you to instead lay beside you. “What did you bet huh my dick was small or that I’d last three seconds.”
You laugh at the accusation.
“Nope I bet the opposite." You smirked. "It's always the silent ones who surprise you.”
Jonathan looked at you softly, surprised.
“Yea… I guess so."