I very much enjoy anal sex, and have for years. However, my first experience was like many women; unprepared, no lube and no patience, and. 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? And, is it. “Our first anal sex experience was a mistake. We were trying the rear entry or doggy style and both of us were drunk. He accidentally inserted.