Lol what.
You said the condom sex isn't about pleasure, when it is! You personally can't have sex with a condom on, because you can't stay hard, which is why you can't use a condom... and what is the reason for sex? Pleasure!
Have you tried going up a size? Apparently that can help. Otherwise id look into toys and other ways to get off when not in a monogamous relationship.
Serious questions, if you were to have unprotected sex (like a ONS) with someone whilst single, would you get tested after, and then wait 6 months after testing to have sex again, to ensure there are no STDs? I mean, in a committed relationship it doesn't matter, but if you are single...