Our guy has never had trouble with his self-esteem, but his girlfriend has become bored with their sex routine and wants to try something new. She wants him to stick his penis into her asshole! He is inexperienced with anal sex and wonders how things will turn out since he never did something like that before. He has no one else to discuss things but his stepmom. They have a good relationship; he isn’t shy to ask her, and she isn’t shy to show him what exactly to do! So she offers him to try her ass and learn to do anal properly. Since the girl has to be very horny for anal, he starts with licking and sucking her clit. Then she positions herself on the edge of the bed, spreads her legs and butt, and he slowly starts to probe her asshole with his rock-solid tool. The head of his penis slips into his stepmother’s anus and her sphincter closes around the shaft. He states that he likes it, and she asks him not to hurry since she want to enjoy a long fuck. She instructs him on what to do and how to maintain his tempo. He is on cloud nine but manages to listen to her and do exactly what she tells him to. When they both get close enough to cum, they stop so she can give him a quick blowjob before they continue with anal fuck. The hot naked stepmom then mounts on top of him and takes his massive prick into her ass in a cowgirl style. When she sees that he’s about to cum, she stops since she saved the best for the end. She demands him to hammer her ass in the doggy style since the first anal lesson wouldn’t be complete without this position. Then she stops him again and turns into the reverse cowgirl position, and orders him to pound her as hard as possible until both of them cum.