Does it hurt being devirginized

Answer 1

Typically, it hurts females their first time, and guys having anal sex for the first time.

Just go slow and make sure there's plenty of lubrication. If it's a female, foreplay foreplay foreplay to make sure she has plenty of her own lubrication. For guys having anal sex for the first time (and also could be for women), generously spread KY Jelly or Vaseline on/in the hole and on the "offending member."