<human>: So, I have 2 pretty bad first time stories...(Yes, 2 first times...)

So, First time 1: Almost there!
So, I had been dating this girl for about a year, we were 17, seniors in high school, she was my first girlfriend, I, her first boyfriend.  So, after a few months of fooling around, we decided we were tired of just taking turns, and decided to just bang already!  so, we start out with foreplay and all, and once she is sufficiently wet, I go to put it in, and just can't.  shes so tight it just won't go in.  My fingers went in no problem...  So, I got all excited to finally fuck her, and boom, no go.  We tried several more times throughout the 2 more years that relationship lasted, and it never worked, it hurt her too much.

Now, first time number 2: this time we got there!
So, broke up with that girl in a huge mess after spending 2 years long distance.  Dating this new girl for a few weeks, and we'd been having some great sexy times.  (God damn she was hot....  way out of my league hot...)  and in the heat of the moment, we just slid it in.  I proceed to fuck the shit out of her, and a minute later, she's done...  She reached the peak, got tired and rolled off...  Isn't it the guy that usually ruins the first time prematurely?

Can you condense the text into a few key points?
<bot>: First time I was going to have sex, it didn't fit, first time I had sex, she prematurely came...