Levi Jackson has accomplished quite a few scenes with other dudes here on Broke Straight Boys, but this sexy red head has yet to bottom in any of those scenes. So since he needs some help getting comfortable opening that ass up for us, we’ve decided to let him ease himself into it with some sex toys. We’ve given him three different size dildos to work with and when he takes off his boxers and lies back on the bed, he lubes up the smallest of the three and very slowly eases it into his hole.
He spends some time fucking his ass with the dildo while he strokes his own dick, moaning as his ass accepts the toy. When he’s feeling brave he grabs the next dildo, a size up from the one he was using, and pushes it into his ass despite a little resistance from his tight hole. When he’s stretched his ass with that one he tries the last dildo we’ve provided but that one is just too big to even get inside his newly penetrated ass. He goes back to the middle sized dildo and as he pushes it inside he finds that magic spot and cums hard, ready to try the real thing next!