Starring the exquisite Jessa Rhodes; Jessa is the best friend you could ever get. She's smart, fun and her best quality; she listens to your problems when you're in need. Her friend Carson came to her for sexual advice. His girlfriend's bored with the sex they're having and he needs something to juice up their intimacy. After a quick summary of their sexual adventures so far, Jessa understands why his girlfriend is getting disinterested. He's obviously uneducated on the subject and his naïveté will be the death of his relationship. Fortunately for him, he came to the right person. Jessa introduces him to anal sex, but he's just not getting it. So, as any good friend would do, she decides to show him how you should warm up a woman before anal sex. Because you just can't go guns blazing and put your dick right in there without at least relaxing her muscles a little, right? He agrees to be a good student to his teacher and licks his friend's pussy and fingers her ass just like she told him too. He's a natural. Everything's going to work out just fine with his girlfriend. Psych! He fucked up real bad. His girlfriend left screaming after he went balls deep in his girlfriend's ass without even using lube. Carson did everything Jessa told him to do. She must have forgotten to explain that part and that her best friend is a little dim. Does she really have to show him everything step-by-step? Guessing she has no choice, and being the best amiga in the world she gets the lube and lets him fuck her in the ass, the proper way this time.