I am just curious about how long it takes some women to let a man have anal sex with them. Do any of you have a first date anal story? What is. The Debrief: Anal sex is on the rise. Yet having it on a first date is still considered a taboo, apparently. Why? Picture the scene: I meet a friend. Backdoor entry is now so mainstream, some guys request it on the first date. So, what's your take on the once-taboo act? Open up and give us.