Description: Oliver Flynn nervously arrives for his massage and is greeted by Adriana Maya, his masseuse for the day. She warmly invites him inside to get started but it's quickly revealed that Oliver is shy about his body. Even so, Adriana assures him that she'll be nothing but professional, so Oliver takes a deep breath and keeps going. As Adriana first gets him through the shower and then leads him to the private massage room, she gently prods to find out why Oliver's shy. Although he's hesitant to admit it at first, Oliver soon shares that he's shy about his body, which has caused problems in his past romantic relationships. It seems like his girlfriends weren't too turned on by his insecurity. So, to gain more confidence and prepare him for the next relationship, he thought getting naked in front of a masseuse was a safe way to practice being nude in front of a girl. Adriana is touched and agrees, then commits to building up Oliver's confidence by making the massage nice and intimate. As Oliver relaxes, he starts to realize that this isn't so bad after all. In fact, he's amazed, and when Adriana finally asks if he'd like a happy ending to REALLY boost his confidence, he's game! Oliver is beyond happy as Adriana sinks her pussy down onto his cock. As she rides him, Oliver starts to believe that maybe there's hope for his confidence yet!