Sex with boyfriend

My boyfriend and I are long distance and see each other once or twice a month. We’re both virgins but we always mess around a little. I’ve given him blow jobs and hand jobs and he’s fingered me and played with my tits and clit. Last time, things got heated and I asked if he wanted to have sex. He said yes so we waited until nighttime but just when we were about to, he asked if we could wait. I want him to feel comfortable and enjoy it so I’m okay with waiting. He felt really insecure about it and asked if I wanted to break up and promised he’d be ready next time I came to visit (to which I replied that he doesn’t need to be). I just figured I’d wait until he initiated things. In the week leading up to the next visit, he sent me pictures of him being hard through his boxers and he sent me texts like “what I want to do to you” and “I want you so bad” so it got me excited for what might happen next visit. Well my next visit came and there wasn’t any mention of sex. I did give him a hand job and he let me touch his dick while cuddling and I let him play with my tits. But I was a little disappointed after all the build up. The nextttt time we see each other, should I ask him if he’s ready or should I just wait until he initiates things?