First time went bad

Me [16F] and my bf [17M] agreed to have sex for the first time. But, when he tried to go in for the first time it hurt, a lot. He only got half way in, he couldn’t go further because I would be in pain. We laughed about it but we’re frustrated about it too.

Also, the condom didn’t fit him properly, he said it felt a bit tight around his penis. When he went in it he said it felt like his foreskin was getting pulled all the way back to a point it started to hurt a little bit. Maybe we weren’t lubed up enough?

Any advice on how we can have sex more smoothly next time?