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anus does not. Condoms Unprotected anal sex is considered a high-risk activity for spreading sexually-transmitted infections (STIs) and disease 9, more so than vaginal sex 10, because the anus is more delicate that the vagina. Theres no need to stress about it if you dont get much stimulation from. You can check out the instructional Youtube video I made with Sunny Megatron on how to correctly and safely milk a prostate here. This is the easiest and smoothest way to learn how to have pain free anal sex.