Message: How to Prepare for Double Anal

Anonymous: I’ve read your post about dp. My boyfriend, his buddy and me want to try double anal. But it sounds dangerous. What should I consider and how do I properly prepare for it?

Presumably you already engage in anal sex regularly and can comfortably get fucked in the ass with a single dick. That’s an important first step. Then you should use a dildo larger than your boyfriend’s penis, but not yet twice the diameter. Work up to being able to comfortably fit that in, and then try either two penis-sized dildos or your boyfriend and a dildo. Have him fuck you for a few minutes until you’re loosened up a bit and then add more lube to the area around your anus, to his penis, and to the dildo, and press the dildo up against your anus either forward or backwards of his penis, gently increasing pressure until the head starts to pop inside. You should take things slowly here and stop if it really hurts, but otherwise keep slowly increasing the depth until it’s inside. Then have him continue fucking you, very slowly at first and increasing as you can take it.

Once you can do that for a while and have done so multiple times, consider trying double anal with two guys.

It’s no more dangerous than any other semi-large anal play: you can hurt yourself if you’re not careful, but if you take things slowly and work your way up to being able to fit that much inside it’s totally harmless.

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