What if you fucked Dipper in a dress

God he had such a small body, thin and lean and not even a hint of muscle had begun to form on him. With your large hands on his slim hips, it felt like he would break in two if you actually tried gripping him, and the thought of just how big you were compared to him made your head dizzy. Dipping your head down, you press your lips against his, soft at first and quickly pushing harder until the lipstick you had watched him carefully applied earlier smeared across both your faces. He was just as eager as you, bringing up his hands and gripping at your hair to keep you from pulling away. Dipper is still an inexperienced lover, his kisses sloppy and wet but he’s so enthusiastic you can’t help but enjoy it, biting down on his lower lip and using his surprised gasp to slide your tongue inside his mouth. You let your hands drop down from his hips, instead letting them rise on his bare thighs and slide up his skirt until your fingers brush against the silky fabric of his panties, smiling against his lips when he groans from the contact. The sound makes you lightheaded, the blood rushing from your head south until your hands are shaking and you have to pull back to gasp in air; and you look down and see this squirming, flushed face little boy with huge doe eyes looking up at you. He looks like a short-haired Mabel when he dons that too big sweater and tight skirt, and with the way his lips glisten in the low moonlight streaming in through the attic’s window, you can’t help but crush him to you again. You shift so that you’re the one laying on the bed and he’s straddled above you, his lower half grinding into your lap as you lay one hand on his thigh and use the other to grab him by the face. This time the kiss is gentle, your lips barely touching until you start trailing kisses down his chin, tugging on the collar of his sweater and nipping at the space where he neck and shoulder meet.

He tosses his head back, and you can’t help but cut your eyes upward to ogle the look on his face. His eyes are completely shut; his entire face flushing but his cheeks in particular are an attractive dark red. But when you start to suck and bite on his neck his mouth opens in a tiny ‘o’ and his eyes fly open. Sharp canines digging into sensitive skin, you bite down hard enough to leave a bright red bruise, relishing in the faint whimpers and low moans from the tiny body in your hands. You just can’t keep yourself still, and almost as soon as you pull away from his neck your lips are kissing their way back to his mouth, your hands roaming up under his sweater and feeling on the burning hot chest, ghosting over his small nipples. They harden with little incentive, so you start twisting them between your thumb and index finger, sometimes pinching too hard just to hear Dipper yelp, to feel him bounce on your lap in surprise. You know he can feel your dick straining against your pants, pressing against his rump every time he wiggles his hips, and somehow that thought excites you even more. He breaks your kiss, panting heavily and mumbles as if he’s embarrassed someone else will hear him,

“C-come on man, when are you gonna put it in?” He sighs out, the first time he’s managed to put together a sentence that night, so you kindly oblige and carefully grab him by his sides to place him on his hands and knees on the bed. His petite ass shakes from side to side, the bright pink color of his panties practically a beacon in the night showing you where to go. You only bother sliding the panties off his slender frame, watching in fascination as his ass puckers ahead of you, and you take a moment to just enjoy the hairless crack of his pale ass. You’re both prepared for this situation, and it only takes a minute of fumbling around the massive piles of dirty laundry to find a tube of lube that’s been stashed away. Squeezing a generous amount onto your fingers, you slick yourself up properly and, with one hand spreading his cheeks, work your index finger inside of Dipper. He groans, letting out a shuddering breath, so you pause with your finger barely inserted in his tight hole to give him time to adjust. It takes what feels like ages, working just your forefinger inside, wiggling it and thrusting slowly until you’re able to pull out and introduce your middle finger as well. At this he whines, pushing his body back onto your fingers, haphazardly fucking them.

It’s almost…cute? The way he grunts while taking your fingers, and the squeals he lets out when you curl your digits are both adorable and cause your already hard dick to throb; the implications of getting hard at a willing Dipper ridding your fingers makes you break into a sweat and nervously you pull out of his backside. He groans again, and you can practically hear the disappointment. Swatting his ass, he takes the hint and moves aside so you can once again lie on the bed, letting him straddle you. This time, however, Dipper takes the initiative and unzips your pants, pulling out your dick and waiting for you to coat it in lube. When you’re certain it’s slick enough, you let him take control again. He holds it steady while he positions himself over you, trembling as he slowly lowers himself onto you. Even before he’s reached your tip you can feel the heat of his ass and it takes all your self-control not to plow into him. He obviously can’t take your entire length, but watching his face grow red in frustration as he desperately tries to descend upon your cock makes your heart beat like crazy; you struggle to keep from bucking wildly into him and instead distract yourself by wrapping a hand around his own pre-pubescent dick. Your palm dwarfs him, engulfing him in heat and slowly stroking up and down. He pulses in your palm, nearly in time to the panting from the stress of riding your dick. It really only takes a few loose jerks to get him to cum in your hand, smearing the off-white fluid on the front of his skirt and making a mess. Before you can rub his spunk off on the sheets, his small hands reach for your wrist, and you let him bring your dirty hand up to his lips so he can lick it clean.

Jesus fucking Christ

He gives you that fucking coy look, lowering his lids and letting you see the glittery eye shadow he put on, as if anticipating this exact look, his tongue wrapping around your digits to clean between them and god you thrust suddenly, both your cock and your fingers, jamming into Dipper’s two holes and watching him sputter. Using your clean hand to hold onto his waist, you forcefully bounce him at a faster pace, watching his eyes roll in the back of his head as you pound into his ass. Your stomach gets warm, knotting up as you continue your rapid pace; your entire body feels on fire as you bring yourself to the edge with your young lover. When you feel close, you pull him off and push his face as close to your prick as possible, managing to get him angled right just before you start spurting. Your cum covers his face, landing in his hair and falling down his cheeks in thick drops. Both of you are exhausted, so much so you don’t even mind when Dipper crawls to the top of the bed to snuggle his cum-soaked face into your chest. Ignoring the cooling fluid smeared on your chest, you wrap an arm around Dipper and pull him close, the two of you falling asleep shortly after.