When does sex stop hurting and start feeling good after losing virginity?

Okay so I'm 17 years old and I lost my virginity to my boyfriend. We have had sex about 5 times now and every time I don't feel anything I guess pleasurable from it. Also he hasnt been able to fully go in cause I'm tight I guess. But yeah its just frustrating. So when does sex start to feel good and how can he be able to fully go in and actually be able to feel pleasure?