My partner recently asked me to try anal sex. But my logic is simple: If a guy wants to get all up in my business, then I want to be sure he's OK. Ask around and see if a guy wants to do anal EVERY time. .. “Once I was having sex with my boyfriend of two years and he tried to slip it in the back door and. A few things: First, it helps (you) to have some alcohol beforehand. Get a buzz, and it'll help you relax. Second, it does NOT help for your boyfriend to have.