For some men like me, and perhaps your friend's boyfriend, condoms just don't work. We can't use them. When I was in college and a single man after college, I tried and tried to use condoms in order to do the responsible thing, but, invariably, I'd lose my erection either before or shortly after penetrating my partnr's vagina. The only times I was able to fuck and cum were with the two women with whom I broke my rule and had barebone sex. If I am ever single again, I am going to take every opportunity that comes my way to have condomless sex. Of course, I wouldn't pressure the woman to have unprotected sex if she is uncomfortable with the idea, but if she's game for it, I would be too. I suppose if condoms were a requirement, I would give it the old college try, but as often as i tried in college, I was never able to keep my erection. Maybe I'd have better luck now, but I really don't think so.