Sex w/o a condom hurts my bf?

This is a wee bit long, but please help!
My boyfriend is uncircumcised, and I'm the first person he has had sex with. We've always used a condom even though I'm on the pill (just to be extra safe), and the sex is great. 
When we tried to have unprotected sex (the only time we've tried that so far), he had to pull out within seconds because he said it hurt, since his foreskin had never gone back completely before. 
Fast forward to a couple weeks later: while having sex with a condom on, his foreskin ended up rolling back painlessly. He realised this once we finished and he took off the condom. 
Now, he says his foreskin's been acting a bit "weird" ever since. It still rolls back now, ever since that day, but doesn't go back over the tip of his penis properly.  
Should he get circumcised? I'm a little worried!
Edit (8th Jan): He went to a doctor and addressed the problem! Turns out he doesn't need a circumcision, just some meds. He should be fine in a few days. :)