Back in the early days when I was experimenting and trying to discover WHAT I liked, anytime I would bottom it was difficult, and I would bleed for days afterwards which was concerning. I finally decided the prep, aftermath and anxiety was not worth it for me, since I never really ENJOYED bottoming anyway.... but if you enjoy it, there are many bottom afficianados who swear bottoming is the greatest thing, so it might be worth giving it some time ? As your anus stretches over time and gets used to the invasion, it might become more comfortable and less painful in the aftermath....