If it hurts, your doing it wrong. start with lube and fingers, slow. Then introduce a set of comfortable butt plugs, start small, and be relaxed. Keep at it daily and you will start to enjoy the feeling more. Then after plugs go to small toys then gradually larger. Once you are stretched and ready after a month or so of prep, you will be squirting all over the bed from good dick in your ass if your anything like me.