what happened??

So I lost my virginity to my boyfriend (soon to be fiancé) in June. Before we even had sex, however, we had talked about the risk of pregnancy. we both agreed that pregnancy wouldn't be a problem if it happened, but we used a condom anyway. my boyfriend went out of town after this and when he came back (nearly a month later) we had sex again and we used a condom. there was a lot going on with his family after that and we never really got the chance to be alone and have sex again (because his family were coming in and out of our house on a daily basis) and when we finally got the opportunity again, we decided to try without a condom. he couldn't fit his dick in. like at all. it was uncomfortable and painful for me and he told me that it seemed like I was just way too tight (to the point that it was even hurting him). what happened? was I just not wet enough? should we try lube next time (because the condoms we used were lubed)? or did I just tighten back up?