When did anal become standard issue? No Seriously? WARNING: This article deals with descriptions of sex, and some of the comments are. What Does Double Penetration Feel Like? How To Or even safer for woman is to try it first with the dildo and butt plug by herself . As far as what it feels like, it's basically like having anal and vaginal sex at the same time. There are stigmas associated with men who have anal sex with other be commonly seen as the female role in a heterosexual intercourse.