Tease and Release

Jim sets the belt down and spreads Jack's cheeks apart, examining his tight hole. "I'm going to make you regret begging for this," he says, before spitting on his fingers and pushing one inside Jack.

Jack moans as his father begins to stretch him, adding another finger and then a third. Jim's fingers feel huge inside of him, and Jack can't help but think about how much bigger his cock is going to feel.

"Please, daddy," Jack begs. "I need you inside of me."

Jim removes his fingers and stands up, positioning himself behind Jack. He spits on his cock and rubs it against Jack's hole, teasing him before pushing inside.

Jack gasps as Jim enters him, feeling the stretch and burn of his father's thick cock. Jim starts to move, slowly at first, but then picking up speed as he thrusts deeper and harder.

"Oh god, dad," Jack moans, reaching back to grab onto Jim's thighs. "Fuck me, daddy, fuck me harder."

Jim obliges, grabbing onto Jack's hips and pounding into him. Jack can feel his orgasm building, his cock throbbing against the fabric of his mother's dress.

"Daddy, I'm gonna cum," Jack gasps.

"Not yet," Jim growls, reaching around to grab Jack's cock. He starts to jerk him off as he continues to fuck him, bringing Jack to the brink of orgasm before slowing down.

"Please, daddy," Jack begs. "Please let me cum."

Jim relents, allowing Jack to reach his peak. Jack moans loudly as he comes, his cum soaking the fabric of the dress. Jim continues to fuck him, chasing his own release. Jack can feel his father's cock swell inside of him, and then Jim is groaning loudly as he fills Jack's ass with his hot cum.

Jim collapses on top of Jack, both of them panting and sweating. Jack can feel his father's cock still twitching inside of him, and he can't help but smile.

"Thank you, daddy," Jack whispers, reaching back to rub Jim's thigh.

Jim chuckles and kisses Jack's neck. "Anytime, baby," he says. "Anytime."

The two of them lay there for a few moments, catching their breath before Jim pulls out of Jack and helps him to his feet.

"Let's get you cleaned up," Jim says, leading Jack to the bathroom.

Jim helps Jack out of the dress and panties, gently washing the makeup off of his face. He then leads Jack to the shower, stepping in with him and wrapping his arms around him.

"I love you, Jack," Jim says, kissing the top of his head.