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They have to make sure they go very slow. As I got more aroused she said it felt kind of weird like she had to poo. FYI to any haters she likes being tied up, handcuffed, slapped, called slutty names and choked even when sober so no comments about how I took advantage of her drunkenness. But the story is really to say that anal sex is horses pain free anal sex courses. Me and my husband like having sex like daily using techniques i learned from sean but anal sex sometimes we wait a few days or weeks in between sometines not however when its been awhile it does hurt for like 10 seconds when he does penetrate sometimes he does use his fingers when I give him a blow job other tines he just gently penetrates but we never use lube or condoms i hate the feeling of condoms pain free anal sex What can I do to make it less painful that first 10 seconds and to make me actually orgams like a OMG orgams because from anal I never pain free anal sex a mind blowing orgasms. Answer Wiki.