He decided to take a day off (Sam made him) after tearing a muscle on the last hunt. He treats himself a little, soaks in a hot bath, beer in hand. He only gets out when he thinks he’ll accidentally fall asleep. He steps out and wraps a towel around his hips and walks to his room. He stops in the doorway when he sees Jack sitting on the bed. “H-hey kid.” He blushed a little. Jack stands. “Hi. Um... sorry,” He noticed Dean’s cheeks flush. “I don’t mean to make you uncomfortable.” (Cont.)
Dean shakes his head. “No, no. I just didn’t know anyone would be in here.” He walks to his drawer and pulls out some pajamas. “I’ll just change real quick.” Jack stops him. “Maybe you don’t need to…” He looks at Dean. Dean sighs and puts the pjs back. “I’ve been wanting to… have sex again. I-if you’re okay with that.” Dean doesn’t wanna look too eager but he smirks a little. “Come here.” And Jack lets him kiss him. “You’re adorable you know that?” Jack smiles softly. (Cont.)
Dean drops his towel and sits. He watches Jack undress as he gets comfortable at the headboard. He reaches over to his end table and pulls out some lube as Jack carefully climbs onto his thighs. Jack takes it. “Let me.” Dean smiles and hands it over. “Do you’ remember how?” Jack opens the cap and pours a little too much onto Dean’s hardening dick. Dean chuckles and takes it away then kisses Jack again. Jack waddles into position, stroking Dean into complete hardness as he sinks down. (Cont.)
He winces a little. It has been a while since they’ve been able to do this, or since he’s asked. He never wants to intrude with the subject. He hisses a little trying to fast to sit all the way. Dean groans and holds his hips. “Take you’re time kid, don’t want you hurt. We’ve got all night okay?” Jack nods. He breathes and tries to focus on the moment. He kisses Dean again, lets Dean’s tongue slide over his own. Before he knows it he’s moving slightly. Dean smiles into the kiss. (Cont.)
Jack braces himself on Dean’s shoulders and finally sinks all the way onto Dean’s dick. He bites back a moan and smiles as Dean moans for him softly. Dean sighs and kisses Jack’s neck and collar. He hugs Jack close as Jack starts to bounce. He nips the kids shoulder and Jack raises a hand to Dean’s hair and tugs a little. Dean’s smiles wide and quickly shifts down the bed. Jack watches him confused. “Hold on kid.” Dean says gruffly and holds Jack’s hips up and starts pistoning into him. (Cont.)
Jack moans loudly and almost collapsing. “A-ah! Dean!” He gasps and throws his head back. “Fuck… Jack.” He grunts through gritted teeth and pants when he stops his hips. He laughs a little. “Never doubt that I know what you’ll like.” Jack pants with him. “I never did,” He leans over and kisses Dean sloppy. “Do it again.” Dean smirks and pounds into Jack again, his cock twitching as Jack moans into his mouth. Dean goes for less than a minute until he can’t anymore. (Cont.)
“Shit, ‘m gonna come faster’n I thought.” Jack laughs softly and shakes his head. “Whenever you want.” He continues to ride Dean, going faster as Dean grips his thighs. Dean reaches between them and jerks Jack, twisting his wrist. Jack’s hips thrust into Dean’s hand and he’s a whimpering mess. Dean is panting and cursing quietly and soon comes inside Jack, his head pressing into the bed, moaning “Son of a bitch” a couple times. Jack finally comes over Dean’s hand and onto his chest. (Cont.)
Jack falls forward and buries his face in Dean’s neck as he finishes, moaning and twitching and panting. Dean stops when Jack grabs his wrist. Dean wipes his hand on the bed, he’ll do the laundry tomorrow. He holds Jack and lets him calm down, ends up holding him all night. (End.)
