Yes - especially getting through the sphincter. I had a considerate, patient, gentle partner who prepared me well and used plenty of lube.
The pain wasn't anywhere near unbearable. I found it to be a psychologically significant part of the experience of being devirginized. My partner had me take it like a woman - especially the way most virgin girls get it - on my back, thighs wide and legs up, face-to-face, body contact, naked genitals, etc.
It hurt in a strangely pleasurable way. When it was over I think I had a MUCH better understanding of how my wife felt, and what she experienced when I took her vaginal virginity and ruptured her hymen - and why she cried through the entire first fuck, but still clasped me to her.