First, I think it’s safe to assume that Molly Triffin is really a woman, and Jason Torchinsky is really a man. They have a lot in common: an easy-breezy magazine-y tone, and they want to make their audiences laugh. The Jalopnik article wants to inform as well as entertain. On the surface, the Cosmo article also wants to inform, but the writer’s main focus is humor – and most people who have read more than three Cosmo issues recognize that the sex tips are really kind of a joke.
The Cosmo article makes a lot of assumptions about their readers, and role that gender plays in the minds of the readers. It recognizes that a lot of women’s sexual pleasure comes from titillating the partner. But they make the assumption that 1) the man is just happy to have sex, and 2) there is no chance of failure because even if a sex tip doesn’t work, the guy is still ecstatic that he got some.