Dylan Hayes and his boyfriend are making out. As things start heating up, his boyfriend wants to go all the way, but Dylan is feeling a bit anxious because he's still a virgin. Michael Boston, the older sibling of Dylan's boyfriend, barges in and offers to help. Dylan's boyfriend is annoyed, but Dylan confesses that he's nervous and is worried that his boyfriend's cock won't fit inside him, so Michael cheerfully offers to give some tips. Michael starts by asking if they have lube, but it turns out that they don't. Michael tells Dylan's boyfriend that it's his duty to provide for his man, so Dylan's boyfriend begrudgingly leaves to buy some lube and other supplies. Now that they're alone, Michael asks Dylan if there's anything else that he's anxious about. Dylan admits that since he's a virgin, he doesn't have ANY idea what to do. Michael gives Dylan some advice to help him feel more prepared, but then starts coming on to Dylan, saying that he can help Dylan get warmed up. Dylan is startled at the idea of betraying his boyfriend, but Michael says this will help make sure Dylan's first time with his boyfriend will be magical, so Dylan agrees to give it a try. They start with some kissing and fondling, and then get undressed. Dylan tries giving Michael a blowjob, and is pleased to find out that he's a natural at sucking cock, and sucking on balls too. Michael rims Dylan and prepares him for penetration, and Dylan eases himself onto Michael's cock for cowboy sex. It ends up feeling much more pleasurable than Dylan was expecting, and Michael eagerly fucks Dylan in various other positions. It's clear that Michael's intentions aren't entirely altruistic, but Dylan is enjoying himself too much to care.