One possibility is he was testing you. A guy asking to go without a condom doesn't seem out of the ordinary based on what I read here. A guy asking to go without then also saying he has unprotected sex with others seems like a lot of extra info. It just seems odd to me.

While tests are dumb, I'll be honest and say if it was a test, you did fail. Not a D, not almost passing, but very clear failure. If you do that you will end up with an STD and I hope for your sake it is a temporary one and not a permanent one. Having sex with a stranger (and he is a stranger at this point) without a condom is dumb. Doing it when you know they are also having unprotected sex with others is one of the dumber sexual things you can do. Please, please, please take a break from the bowl and read up on std's, protection, safe sex, all of that. Future you will thank you.

Sorry if this is harsh, but I feel like it needed to be.