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Jason doesn't think anyone else has noticed the holes in Dick's trunks yet or if they have, they haven't said anything so they can also enjoy the show. Dick hasn't noticed. He's running around and showing off and occasionally giving a glimpse of his pretty boy pussy to anyone who's looking. Maybe other people haven't noticed because they're well behaved enough not to be eyeing a teenager’s bottom half but Jason isn't.
He doesn't let on to Dick about the problem either. He just drinks his beer and enjoys the occasional lewd peek. It almost seems like Dick is trying to flash him specifically.
Eventually Jason does get up to do something about this. Dick is sat at the bar that's been set up for their pool party with his butt not properly on the seat. Every time he leans over the bar too much, he shows off his pussy more. Jason comes up behind him to block the view and Dick grins up at him.
Jason takes his empty beer bottle and slips it through the hole in Dick's trunks and shoves the tip into his cute little pussy. Dick gasps loudly before quickly covering his mouth.
“Shh. You don't want anyone to notice, right?” Jason says quietly. Dick pouts at him but just bites his lip and tries to stay quiet. Jason thrusts the bottle into his tight little pussy until he starts to get wet and squirms. He whines quietly but again tries to keep silent. Jason shoves the bottle in deeper.
“Jason,” Dick whines.
“Don't complain. You're the one running around showing your pussy off to anyone and everyone. Of course I'm gonna stuff something in there,” Jason says. Dick's slick is beginning to run down the bottle and even as he tries to lift higher up, Jason pushes it deeper until the entire neck is inside him.
“Someone's gonna see,” Dick says. Jason doesn't really care. No one's watching right now, anyways. If Dick didn't want to give free shows, he wouldn't be running around flashing his pussy. Jason grabs Dick's hips and pulls him back to make him sit on the bottle now. Dick gasps as he feels it inside him. The neck isn't very big but the rest of it is.
“It's too big,” Dick says. Jason pushes his hips down roughly until the thicker part of the bottle starts to slip inside, stretching Dick's pretty pussy. He whines.
“You've taken bigger,” Jason says. Dick squirms as it goes deeper. It's so hard and stiff inside him. He bites his lip.
“Is it almost in?” he asks. Jason gives him another shove down and Dick gasps as he feels the opening bump against his cervix. He covers his mouth again to stop from crying out. He's so wet that Jason isn't having trouble shoving even something this size inside him. His cervix is giving him some trouble though. Jason shoves and pushes to try to force it in and Dick just whines more and more.
“Come on, Dickie. The sooner it's in, the sooner this is over,” he says.
“It's too big, Jayjay,” Dick whines. Jason lets go of his waist and Dick briefly takes a breath. Then Jason grabs his shoulders and shoves him down roughly. The bottle slips into his womb suddenly and Dick cums harshly. Jason just keeps shoving him down until he's sitting completely on the bottle and there's a cute little bump in his belly. It's hard and he can't clench down without whining.
“Looks like it fits just fine,” Jason says. He reaches down to stroke Dick's belly bulge and Dick drools. He always takes big objects so beautifully. With Dick's pussy nice and stuffed, Jason grabs a new beer and returns to where he was lounging. Dick is a lot more careful to not flash anyone now and he stops showing off so much to just sit around and try not to drool.
After a while, he comes over to Jason and Jason looks at him with a smirk.
“Did you get too horny?” he asks. Dick doesn't say anything he just pouts. Jason gestures for him to come closer and when he does, he turns Dick around. He puts his fingers in the hole in Dick's trunks and rubs his dripping pussy and feels the hard beer bottle holding him open. He hasn't let it slip out at all.
Jason pushes a pair of fingers into his soft pussy and Dick whimpers but stays still as Jason begins to wiggle it free. He pulls it out a little before fucking Dick with it slow and hard. Dick struggles to keep his balance. Jason's hand is dripping with his slick now and he pulls the bottle out slowly. It's also drenched with his sweet boy slick.
Damn, Jason can't believe that was inside him. Dick sighs when it's finally out. Jason pulls him over by the waistband of his trunks and Dick fidgets nervously as Jason pulls his cock out. Not wanting anyone else to see, Dick comes to sit on Jason's rock hard cock. It's a little thicker than the beer bottle but he's been stretched by it now.
He still isn't fast enough though and Jason grabs him to shove his cock into his wet hole all at once. Dick covers his gasp. It feels better than the beer bottle. His tight little womb squeezes the head of Jason's cock snuggly.
Jason loves fucking Dick in front of strangers. Some of the family might notice but no one else does. Dick bounces on his lap discreetly as he tries to make himself cum again with Jason's cock. Jason grabs him suddenly to hold him still and stuff his womb with cum which makes Dick cum, too.
He just sits there for a bit and warms Jason's cock.