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He is unsure how this happened.
One minute, he's complaining to Jessie, the next, she's on top of him, kissing him nonetheless, in his bed.
It makes him feel lightheaded. The weight of her against him, the feel of her hands in his hair, her.
Romeo can't help but wonder what it'd be like to feel her, like really feel her. She could be riding him, or maybe... she could be under him with her nails scratching against his skin as he plows into her... (Fuck she'd look so pretty like that...)
He then thinks about what she'd like. Should he be big? Or maybe average? Should he be thick or thin?
As he fantasizes, Jessie surprises him by putting her hand in his pants and feeling around.
"Bloody hell! Could you at least give me a warning before- nhh~" She rubs circles against his clit through his underwear, making him shudder. (Pussy it is, then...)
"Ffffine! Just-... Just be gentle...!"
"Didn't expect someone like you to say that~" she teases.
"Shut up...! Just keep going...! Mmh...~" He rolls his hips up into her hand, starting to grow impatient with how slow she's going.
After a moment of teasing him, she takes her hand out, instead deciding to unbutton his pants. "You're such a bloody tease..." Romeo growls, but his voice is shaky, betraying his need.
"I know...~" Jessie responds as she slides his pants off along with his underwear.
She drags a finger through his folds, feeling the wetness accumulated there.
He whines, "Hurry up..."
"You're always so impatient..."
He huffs and take off the rest of his clothes if she isn't going to do it, and she begins to take off her own.
As her naked body is revealed, his heart jumps and his hands go to hold her hips, looking at her as if she is a work of art.
(She's so perfect...) "... My champion..."
Jessie kisses him again and Romeo responds back eagerly.
He whines as she roughly grinds their clits together. "I-I said be gentle! Mmnh Jessie!~"
She listens and he mutters coldly, "Thank you."
"You know I can go rougher, right?" He grows wetter (if he wasn't wet enough already) at the threat, but he doesn't say anything.
As if taking his silence as ignoring her, she does indeed go rougher and he gasps.
"Say you're sorry," she demands.
(Too much... Too much...!) "I-I... Mhhh Jessieee~"
"Did you hear me?" She tugs his hair and forces him to look at her. "Say you're sorry."
"I'm sorry! I'm sorry! Please, please be more gentle! Please!~" (I am definitely going to regret that later...)
"There we go." Instead of slowing down, she stops entirely and gets off of him. "Wh-why'd you stop...?" he whines.
He looks over to see her rummaging through the nightstand and pulling out-... a strap-on?! (Since when was that there?!)
He couldn't help but feel a little nervous, considering this is his first time with a pussy during sex. "You're gonna fuck me with that...? W-why not... Why not let me fuck you? I mean, I can be as big as you want and so much more! Don't you want that, champion?"
"... Tempting, but why are you so nervous about this? You're never nervous."
"N-nervous? Ha! I'm not nervous! I'm just..." he trails off, unable to make up a good excuse, "Fine! I never had anyone fuck me before."
"So you're a virgin."
"I'm not a bloody virgin! I just never fucked anyone with my cunt specifically!"
"... So you're a virgin..."
"Forget it! Just... be gentle putting it in... okay...?"
"Okay." She gets back on top of him, now with the strap-on jutting out from between her legs.
(It's kind of more intimidating now that it's up close... How am I gonna fit that thing...?!)
"I'm just gonna prep you first, okay?" she says, opening his legs to make room for her.
He tries not to care, but he'd be lying if he said he didn't want this.
She slowly pushes a finger in him and he inhales in response.
"How does it feel...?"
"... W-weird... but not bad..."
After a few seconds of pushing her finger in and out, she carefully adds a second one.
He feels a slight pain as she pushes in, whimpering softly.
"Just breathe."
"I'm fine!" he bites back.
As time goes on, the pain fades into pleasure.
"Aah...~ Jessie...~"
She begins to widen him by making a scissoring motion inside him, making him squeak.
"... This is... mnhh... so weird..."
He grinds his hips against her touch, already wanting more, but she pulls away.
"I'm gonna put it in now," she says, already lining up the strap-on with his entrance.
He bites his lip as he feels the blunt tip nudge against him.
She grabs his hand and kisses him as she starts to push in.
Romeo winces, "J-Jessie...~" It's way bigger than he thought.
He grips the sheets beneath him as the strap on is pushed deeper and deeper into him.
Soon she bottoms out and he shivers, whimpering through the pain.
"Are you alright?"
"... I have... a dildo inside of me... what do you think." He pauses before responding honestly, "... It's... hh... still a bit painful, but... yes... I-I am alright..."
"Good... Just tell me when you're ready..." Her thumb caresses the outside of his palm and his heart swells. (She loves me...)
This time, he kisses her first. (I love her...)
She holds his face. (We love each other...)
He let's go of the sheets to tangle his hand into her long hair, sighing, "... I love you, my champion..."
She pulls back from the kiss a little to respond, "I love you too, Romeo..." Just the loving tone in her voice makes him want this to last forever.
"... I think I'm ready..."
"Okay, just let me know if it's too much and I'll stop..." She squeezes his hand, and with that, she begins to pull away, slowly as to not hurt him more.
He whimpers, already missing the fullness, but then she begins to fill him again, this time less painful.
"Ah- Jessiee...~"
He clings to her, his legs wrapping around her waist as she slowly thrusts into him.
He moans when he feels her bottom out again, and the cycle repeats: she pulls out almost all the way, and then slowly pushes back in, over and over.
Soon, the pain is all gone, replaced by an almost overwhelming pleasure.
"J-Jessie- ah!~ Faster...~"
She obeys and he moans louder, his cunt quivering desperately around the strap-on.
Suddenly, she hits a bundle of nerves deep inside him and he cries out, "Fuck!~ R-right there! Right there...!"
She stops thrusting to grind against his g-spot, making him whine.
"Jessieee...!~ Please...~" His head falls back against the pillows and his hand squeezes hers tightly. "... I'm not gonna last long...! Aaah...!~"
But she doesn't listen to his warning. She pulls out and he sobs, desperately wanting more, but not wanting to cum so fast.
She plunges back in, making a scream tear from his throat. He's so glad no one can hear this.
"Jessie- Jessie!- I-I'm gonna-... You're gonna make me-...!"
She continues to thrust hard and deep into his trembling body.
He desperately tries to cling on, not wanting this to end so quick, but the pleasure is too great and he finally let's go.
He cums with her name on his lips and his mind blanks, his body arching into hers.
She pulls out, letting him relax as they cuddle each other.
As he comes down from his high, Romeo asks, "... What about you...?"
"Hm?"
"... You still didn't cum..."
"I know, I'll deal with myself later."
"... Thank you for... for that experience..." he hesitantly admits.
"You're welcome..."
Silence.
"Also, you're welcome for taking your virginity," she says with a smirk.
"Oh, fuck off!"