Obviously bareback is going to feel better & is fine if you are committed to a 1 on 1, trusting relationship. However, if it's just casual sex with someone who you don't have any idea of their sexual history, then not to use a condom is plain irresponsible. As for the question of position, the only position I've found that really works for me is the basic Missionary Position, with the penetratee's legs hooked over the penetrator's shoulders.