Another double-virgin comedy of errors, I mentioned in detail how everything more or less went wrong in the
sex disasters thread.
Summary: Multiple tries, condom was too small (didnt realise till post-breakup), erection problems, pain, although when we finally got the piston turning in the cylinder properly she said she was enjoying it.
I don't think I'd have a problem really with having sex with a virgin again... as long as I'm wearing the right size condom. Small tight girl plus small tight condom equals zero blood circulation, meaning no sensation beyond "ow".