After a few weeks of busty show offs, we’ve taken a step back with a shy first timer named Hilary. She’s got a tight little athlete’s body and, it turns out, a pussy as grippy as a brand new Fleshlight lubricated with honey. From the minute the cameras start rolling for a little behind the scenes talk two things are apparent: 20 year old Hilary is a true first timer and she’s pretty shy about it; and for some reason this really gets Jay excited and he takes a liking to her from the start. As Hilary talks with Jay, you will notice that she’s hardly wearing anything at all. Jay certainly notices and gets some great shots of her pert, pokey nipples tenting her shirt. Jay is yanked out of his distraction when Hilary mentions that she almost never has an orgasm during sex. You can practically hear Jay shout “Challenge Accepted!” from behind the camera. After getting prettied up, Hilary gets settled on the bed for a few more questions and then Jay goes to work with his fingers and then a vibrator where he soon discovers that Hilary wasn’t lying about how tight her pussy is. After a nice deep throat beej, Jay lubes up his cock and eventually manages to fill Hilary’s incredibly tight box. If there were such a thing as a sex detective…a dick dick, if you will, he might determine that the reason that Hilary has never been fucked to orgasm is that her previous lovers have been working with say dime rolls rather than quarter rolls because as soon as Jay fills her up, he manages to fuck her to orgasm in a matter of minutes. Or maybe he’s just got a magic dong. There aren’t any girls in the office here, so we’ll never REALLY know. After getting drilled in doggy, fucked from the side and pounded in reverse cowgirl Jay can’t hold back the tide any longer and unleashes another fantastic, splashy facial across Hilary’s cute smile. You know, with an attitude as positive and up for anything as Hilary’s and as much as Jay obviously likes her we might just see her again and when a girl comes back a second time, well…you know what that usually means.