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He's laying on your chest when you bring it up; not with a sense of urgency or desperation, but simple nonchalance. If he denied your proposal, then you'd simply go on with your day- simple as that.

"Are you sure?" he asks, eyes darting around the room looking anywhere but at you.

You nod and gently grab his face, pulling him in for a soft lingering kiss. "I'll be there the entire time guiding you along. Don't worry, if you do something wrong or if you wanna stop just say the word we can stop. Like always, okay?"

He takes his bottom lip between his teeth, eyes still avoiding you.

A moment of contemplation later, he smiles, wrapping his arms around your neck and nods, pressing you further into the couch cushions. "Okay!"

x

A week passes and suddenly you find yourself mostly naked in bed with an equally disrobed and particularly squirmy John Egbert grinding his hips against yours like a horny teenager.

(sheesh who are you even kidding you two are always going to be horny teenagers, just a little older and grumpier in the mornings)

In a feat of self-control that would leave even the gods speechless, you pry John off of you in favor of rolling to the bedside table and grabbing the lube and a condom. John licks his lips obscenely, settling himself on his elbows and knees, spreading his legs as wide as he can as he practically humps the sheets below him. You run a hand along his back and down the curve of his ass, giving it a generous squeeze. As much as you would love to fuck him like this, there's no time like the present to teach him something new.

Yeah. You two are gonna do the thing. This is so going to happen.

You tug John up by the shoulder, having him wait as you lay down on your back and bring your legs up. You motion for him to sit between your legs while you uncap the lube and squeeze an appropriate amount onto your fingers. You can't help but smirk as John leans forward hungrily when you insert a single slick finger, thrusting slowly. Giving him a reassuring smile, you slip your forefinger in along with the middle one, picking up the pace just a bit.. "See? You know it's not that uncomfortable."

John nods, clearly transfixed on your moving hands. You decide it's time to let him try. Slowing to a standstill, you take your fingers out and use your other hand to grab the tube and little rubber foil to toss at John. "Come on your turn."

He nods, quickly rolling on the condom and squeezing some onto his hand as you wipe your slick fingers on the bedsheets. Meh, they're gonna get dirty anyway.

You sit up and turn to give John a deep kiss, hoping to reassure him that yes you're right here and yes you're not going to let either of you get hurt and yes he is going to do good because he always does good. When you pull apart he smiles sheepishly at you and nudges your shoulder. Taking the hint, you lay back down onto your back and John quietly slips a slender finger inside you.

You let out a contented sigh, yes this was definitely a good idea. He gets a second finger in without too much trouble and hooks his fingers up, rubbing right at your prostate. A deep rumble finds its way from your chest and up to your throat, and John smiles nervously.

When he prods a third finger at your entrance, you can tell he's hesitant. "Hey man, just keep going I'm doing fine, and you're doing great."

He rests his cheek on your knee, absently kissing the joint as he slowly adds his ring finger. You can feel the stretch now, and your face must've showed it because John gasps and rips his fingers out of you like he was burnt. His eyes get really wide as he reaches towards you, but doesn't quite touch, as if he's afraid of hurting you. "Dave I'm really really sorry did I hurt you? God I knew this was a bad idea- not that you have bad ideas but I knew I wasn't ready I should've told you but I didn't want to disappoint you and I-"

Instead you meet his hand half way and grip it tight, kissing his forehead. "Hey, hey I'm fine it was just a little uncomfortable. You do the same thing and you're okay, right?"

John nods enthusiastically.

"Wanna try again?"

His eyebrows pinch together, looking up at your for a hint- any hint for what to say. "It's all your choice man. If you don't want to we can stop and try again another day."

"No. I-I wanna do it."

You smile, "So we're gonna do it? We're gonna do the do?"

John rolls his eyes and snorts, anxiety all but gone as he nuzzles his head against yours. "Yeah we're gonna do the do."

With renewed vigor (and a freshly lubed triad of fingers), John begins again with two fingers, setting a pace that's actually worth getting worked up over. You bury your face into a nearby pillow and arch your back, trying to signal him for more, more dammit john! He gets the hint and without (much) hesitation he gets his ring finger in again.

You try to keep your face from contorting into what might look like pain because honestly it's not really painful and more uncomfortable? But then John, bless his soul, moves to straddle your leg and bends so he can reach your dick comfortably as he fingers you.

Licking sloppily at the head of your cock and thrusting up with his fingers with almost no friction at your entrance- it's almost too much. You tug at his hair and he slows his hand and tilts his head up, panting up at you as he continues rutting against the side of your leg. "Wha-"

But you pull him up by the shoulders, wrapping your legs around his waist; "Come on babe fuck me already," you whisper heatedly against his lips.

John makes a choked noise and flails for a second, frantically looking for the tube of lubrication lost in the sea of pillows and sheets that made up your bed. He squeezes some onto his hand and wastes no time in slicking himself up, hissing when the cold liquid makes contact with his skin.

He lines himself up, and with a reassuring squeeze around the waist, pushes in rather quickly. John may have lady fingers, but even his three fingers are a little too much of a stretch. His penis on the other hand isn't too thick- just perfect.

Fuck yes okay wow why didn't you do this earlier yes yes fuck yes. "John keep goi-ing-"

He huffs and complies with your order, ramming into you just a little harder, wrapping his lubed hand around your erection and pumping in time with his thrusts. Your hand twists itself in your slightly damp hair, as the other one pulls at John, trying to get as close to him as possible as you arch your back.

You let out an embarrassingly squeaky sound as you reach your peak, splattering thick white cum onto your chest. John continues riding you through the aftershocks of your orgasm, so intense that you barely realize your arms coming up to hold John close as he shakes like a leaf.

You maneuver a bit, and slip out from under him, gathering the last bits of your strength to scoop him into your lap. He buries his face into your neck and lets out a choked sob as you begin pumping him, squeezing and dragging your thumb across his leaking head. He writhes in your lap, bucking up into your hand , desperate for more.

"Come on baby," you whisper, biting down somewhere on his neck. He whines, still waiting for the command so he can- "Cum for me."

And just like that he squeals, arching his back with a shudder as you continue to milk him for all he's got.

When John starts coming down, you peel off the condom and lay him down under the covers, grabbing a shirt strewn on the floor by the bed to wipe yourselves clean of any stray lube or any other fluid.

Soon you take your place beside John, letting him wrap his arms around your torso and legs around one of yours. You in turn hold him close, rubbing his back and nuzzling into his hair. "You did really good John, really good, fuck you were such a good boy, perfect."

You feel him smile against your chest, and you smile too. "Do you want to do it again sometime?"

He nods and murmurs a quiet, "Maybe," under his breath.

Again you smile, because he rarely speaks after. You're about to point it out when his hold on you loosens and you realize he's fallen asleep. Pressing a kiss to the crown of his head, you sigh happily.

Yeah, this was definitely a good idea.

I'm sure there are errors and I'd really appreciate it if you would point them out thanks pals.