Need advice for anal

Soo... Me and my boyfriend want to try anal. I know I like it because he used my dildo up there once. But he really struggles with condoms because he just can't stay hard with them on. And it's not healthy to do anal bare right(I imagine because of the poop, lol?)? Though we have both been tested and have no STD's. Just want to know if any of you do it bare and it's OK and what tips you'd give or whether you really need to use a condom and how we could work on keeping him hard for long enough? I tried putting the condom on myself and trying to make it pleasurable but he just couldn't get into it...