my first time was awful.
I'd been dating the girl for months, and we were both virgins. In the end we'd built it up some much, and we were both nervous as hel. We were going to london, and we decided to do it then - bad idea, i think home comforts would have been a plus. First of all we were both really nervous, and then i couldn't get the condom on (i'm not much longer than average, but a bit thicker), then i couldn't get inside her, it was like a wall, despie the lube. Anytime i stopped holding it in place i slipped right back out, so most of the time i was wanking my hand, with m head banging off her labia. She relaxed enough to let me get a bit further in (only about half way), which was the point that her hymin broke, and blood started pouring out of her. Fortunatly i'd herd of some horror stories, so i'd put a towel under her waiste before we started just incase.
It took several hours before we managed to get going, and then when we started properly it hurt her too much to continue. I felt awful because i knew i'd let her down, and she felt bad because i felt bad. It was a really akward night. Mind you we got to laugh a bit in the morning while i cleaned up all the blood, so that the maids wouldn't have to handle the sheets, or clean the bathroom - it looked like a murder seen.

But, we eventually got it right, and we'd a few great times before the relationship ended. I think we both regret building it up though, and making a big thing about it. We should have started weeks before going away, so we could really enjoy our holiday together.

So my advise for anyone that's waiting for there first time is to do it when it FEELS right, not a pre-set date. There were plenty of times that we were both riled up, ready to go, but decided to wait instead. Also, make sure your condoms fit.