Oliver’s Anal Practice Sessions
by A-boy
Inspired by: https://nearhentai.com/2019/08/07/oliver-townsend-character-ask-1/

Oliver went to his room, and locked the door. He grabs his phone and places the camera facing his bed. He hits the video record button. He reaches to pull off his green t-shirt, and places it on his bed. He runs his hands down his chest to his legs, circling to his crotch. He looks back to the camera, smiling lewdly, as he turns and bends forward while taking off his blue shorts, revealing his pink g-string, and tight pink hole. He pulls a drawer out and picks up a large bottle of lube, and a couple toys. He lays them down on the bed, as he uses one hand to grope his cock, and the other to massage his hole. He opens the bottle of lube, and applies some to his hole, and some on his fingers. He presses his finger into his hole, and starts to fuck himself.

“Ohhhhhhhh, uhhhhhhhh, mmmmmmmmmhhhhh” he moans out slowly, and slips a second finger into his loosened hole.

“AAAAAHHHHHH, yeeeeesssssss,” he moans out louder and lets go of his cock, then reaches for his 5 inch dildo. He struggles to apply the lube to the dildo, and slides it all over and spreads it evenly. He slides his fingers out, and aims the tip of his dildo to the now stretched hole, and slides the tip in, his tip leaking precum and twitching, and tensing.

“OOOOOOHHHHHH FFFFFFFUUUUCCCKKK” he yells and moans. He slides in halfway, before wincing in pain, because of the size. He eases it in slowly, and pushes to the base before stopping.

“MMMM FUCK, I’M SO CLOSE,” he yells as his hole adjusts to accomodate the dildo opening his hole up.

He slides his dildo out and in again, his cock leaking precum like a broken pipe all over his tummy, and rubbing, teasing him even more and pulling him closer to climax. He pushes his dildo all in, one last time before his hole clenches onto the dildo, and unloads, eyes shut and mouth open, cumming half into his mouth. He smiles back to the camera showcasing the cum trail from his cock up his chest to his mouth, tongue sticking out. He snaps a pic and saves it for the studio.