1. Hilary Duff Babysitting


    Date: 10/16/2015, Categories: Anal Celebrities, Mature Author: scottynrachel781

    ... used to. “Oh shit,” Ben gasped, stopping mid-squeeze on the tube of lube as he watched Hilary go ass-to-mouth with her vibrator. “Huh?” Hilary asked, then looked down at the toy a couple inches into her mouth and remembering where it had been. “That is so fucking hot,” Ben groaned even as Hilary started to blanch. “Really?” Hilary asked, pulling the toy out of her mouth. Actually, outside of the slightly different flavor, it didn’t taste that bad. It didn’t really taste good either, it just tasted different. “Oh yeah,” Ben said, smearing lube along the length of his cock. “Hmm,” Hilary said, dragging her tongue along the shaft of the vibrator. Seeing the effect it had on Ben, and that it really wasn’t that bad, she made a show of cleaning it with her tongue and mouth. “Ready?” Ben asked, finally moving in behind Hilary. When she nodded, he grabbed hold of his cock and pointed it at the center of her gaping asshole. His heart was beating like a jackhammer in his chest as he found himself facing the wide open gates to Hilary’s perfect ass. While he’d fantasized about anal, and soiled more than a few tissues while thinking about fucking Hilary’s ass, he’d never actually done it. As an ass man he’d watched a ton of porn and frequented several of those sex story sites so he knew he needed to be really gentle. But kinda like the first time he ever had sex, he was still really nervous as he pressed the head of his cock against Hilary’s asshole. “Fuuuckkkk,” Hilary grunted, her ...
    ... eyes shooting open wide as the head of Ben’s cock pushed past her sphincter. Her anus hadn’t presented much of an obstacle after the gradual stretching he’d given her with his thumb and then the vibrator, but it still hadn’t quite prepared her for just how thick his cock was. Yet, thanks to that stretching, she wasn’t screaming and howling in pain like she would’ve thought even ten minutes ago. In fact, as he started making teeny tiny thrusts into her ass, pushing just a little more of his cock into her with each thrust, the fire that she’d felt at the initial shocking penetration was slowly being replaced by a sort of tingle that felt sorta good. Feeling the insane tightness of her asshole, unlike anything he’d ever felt before, even compared to when he’d fucked Jayne Schwartz and taken her virginity. He’d thought Jayne was tight, but that was nothing compared to the constriction he was trying to work through. It almost felt like he was slowly feeding his cock to a hungry anaconda or something, feeling it gripping and rhythmically squeezing him as inch after inch slowly disappeared into its mouth. Finally reaching bottom, Ben pressed his pelvis against the firm globes of Hilary’s ass. Hilary groaned, unable to believe that she’d managed to take every inch of him up her ass, but the large throbbing chunk of man meat parked what felt like a mile into her bowels made it clear that she had. Gripping Hilary’s waist and hips, Ben slowly pulled back, watching his cock slide a couple ...