I think it is wholeheartedly better without a condom but the risk isn't worth it, esp as a gay guy. Whilst I was with my ex, he found out he was HIV positive after a year of being with each other. We had regular unprotected sex and luckily he never passed it on to me; even after we didn't use protection all the time.. But he had several VD/STIs previously which made me think less of him before of his careless attitude towards sex. As he was certain he knew the guy who he slept with. It was a one-time meet, without a condom and boom it only takes a one time sex for a devastating, life-changing illness to become present.
Imo, it's not worth it, esp having anonymous anal sex. It might feel good in the moment, but weeks or months or in his case a year down the life, you'll have to live with the regret.
And now that we've broken up (a few months ago), I can't help but think how hard it's going to be for him to find a relationship with a guy who can love him for him and not be afraid of his illness. In the gay community you basically have to find a guy who is also positive as the safe ones would never have unprotected sex with a positive guy. But unfortunately, most positive men have the illness due to being purposely reckless and having an unhealthy affliction towards unprotected sex.