I've mentioned this in other threads before, but my first time didn't hurt me at all. In fact, I really didn't feel much of anything
- the guy was on the small side, I think, and inexperienced too...he was 18 years old. He was pretty good at foreplay though, and actually a good kisser (the only good kisser I've ever kissed!)
There was a big difference in feeling between him and the second guy I was with, who was considerably larger, or felt that way anyway. It didn't hurt with him either, but he was terrible at foreplay and I was not lubed, and I remained dry the entire time, so I did get a little sore and had problems with infections throughout the 8 months or so that we were together. The actual sex did feel good though - I like it intense, but I prefer not to get infections! (This was due to our body chemistries being incompatible - later on I was with a guy of similar size and had no problems with any of this at all.)