First time??????

Soooo, Im actually kind of embarrassed to say this buttttt... okay so I was with a guy for like 4 years, both our “first time” (keep in mind I was with him since I was 14 all the way to 18) and in all honesty, I don’t think his penis ever actually went in me. I felt it rub against me, but not in me if that makes sense. I never told him because I didn’t want to make him feel bad and I felt like I wasn’t really ready for it. Moving forward, tonight, I kinda did it again for the first time in a long time I guess? And I don’t know if it’s because I’m “tight” or because it would be my “actual first time” but the pain was horrific! I would say it was like lots of pressure. I couldn’t take it and simply asked the guy to go slow to see if that would help but it didn’t. He was super respectful about it and just said okay. I told him about my past and he had that in minds, I really like him and want to take the next step. Any advice to help the pain be less painful? Thanks ladies 🥺🥰

(Sorry if it’s all over the place)