I'm going through the same thing so I asked my Muy Thai master (at the time he was kicking an Iron post with his shins, no lie). He said it always hurts (this after 30yrs boy to man). He also said that u learn to ignore the pain and also that u don't usually feel the pain during a fight ( u shure as heck feel it after the fight). But most importantly don't train to get hit, train to attack and win. Don't try to condition parts of your body to take punishment, condition your body to fight (heavy bag, thai pads and lot s and lots of sparring and I do mean full contact and light).