into the condom, during penetration..? yeah. I can't imagine that it'd be particularly pleasant for a guy to stay that way too long... dunno though.
really shouldn't hurt all that badly. Didn't go beyond a mild sort of "ow" discomfort for me. When that happened, he'd stop, let me relax a bit, and tried again, getting a bit further every time. Relaxing is important, otherwise i'd have just got tenser and made it painful and just downright impossible. It shouldn't have to go beyond discomfort and into painfullness, imo.