Quora User, been having sex with guys for over 25 years a lot of pain even though your anus may be in pain for a couple of weeks afterwards. Apr 2, This skanky chick knows what double anal penetration is all about. Painful bloody anal sex in missionary pose with my petite Latina GF. Has anyone every received, or been a part of giving double anal (two dicks in one asshole at the same time)? How ridiculously painful is it to.