I have used condoms and gone bare many times. In many different women. With condoms I learned a couple of simple tricks. First is get the right size. It should fit just snug enough to allow a little shaft and glans movement inside. Too small, no movement. Too large there's a risk of it coming off. Second is lube. Yes, lubing the glans and part of the shaft before putting the condom over it. The lube inside allows cock movement inside the condom increasing sensation. Just lubing half the shaft keeps the condom in place. If you make a game out of putting it on it doesn't take away from the moment. It adds to it and the both of you are more at ease over STI passing. I'd like to be able to use Jiftips but with my subincision they do no good. Great idea for unmodified guys but not for me. So it's lubed up condoms or bare and really, I can't tell the difference.
After taking time off from relationships, I'm ready to start the dance again. I tried several brands out before i found one that fits well. Wow what a difference!