I'm the same age as the girl. The tips were all good. My first time was not all that long ago. Maybe your friend needs to try different things in bed and try to last long. Have him take a couple minutes rest when he feels that he's comming. Go at it again until the girl feels good pleasure. Another thing that might work is if he gets a little rough in bed. Make her feel as if she is sexy, wanted, good, etc..... He needs to get her excited. Make sure that she's in the mood before they start. Take it easy if it is susposed to be between them it will be. They both need to be comfortable with eachother. Youre a good friend to help them out like this. tell your friends good luck!