And for a lot of couples, the discomfort—or even severe pain—associated with their first try at anal sex scares them away from any follow-up experimentation. Here are some of the important questions— and answers! If today is not the day, fine, you can try again another day. You can tear your anus if you use a certain position that allows for more penetration before you're ready, and Taormino points out that the missionary position allows for the least clitoral stimulation and suggests receiver-on-top for beginners. At that point I was able to slowly position myself so I could come down on my knees while straddling him and then when ready, I could easily slide down onto more of him.