He sucked in a breath as her hisp drove forward. She was telling him to go forth, but how fair was it that he was the only one feeling anything pleasurable? She was in pain and trying to hold on...
Was it supposed to be like this? Was he doing something wrong?

It would likely only be found afterwards either way, since they -were- going through with this. There was a flash of pained expression for her sake as light gasps escaped him as he pushed in more and more, stopping at intervals so her body could adjust.
meanwhile he was stroking her breasts again, hoping that some pleasure could take away a chunk of pain...