What Does Anal Sex Really Feel Like? If you're curious about anal sex and have never done it before, you probably have two burning questions: Will it feel like I'm pooping? . How I Deal With Jealousy As A Single Woman. The unedited truth about anal sex as told by various men and women. . “When we do anal, I can finger her and feel my own cock, which is a really interesting. A clinical sexologist explains why some people may not like anal sex, plus offers tips to make anal more pleasurable.