The background: I'm 22 and I've never had very successful PIV sex, or a lot of experience with it. My first time was my ex's first as well. He was pretty big and didn't manage to get in all the way. It was really painful. I was trying to kind of grit my teeth and bear it to get it over with, but he just couldn't get in and I had to tell him to stop. There was some bleeding, and I continued to spot for the rest of the day, which was also a little scary to me. We attempted penetration about two months after that but again he couldn't get in and we didn't have any lube, and I just really didn't feel like trying after a few attempts. This was during a visit, we were long-distance. We broke up a few months after that, for unrelated reasons. That was over a year ago.
Recently I've started a new relationship-type thing with a friend of mine (which is again long-distance, I don't know why I always do this to myself, haha). When we were together last we came close to PIV once but I got really nervous about his not being able to fit and bleeding and pain and general uncomfortableness, so he couldn't get in :\ One of his fingers can go in pretty comfortably, two begins to push it. We didn't go to the point where it became painful for me. When he tried to get in and couldn't just told him it wasn't happening, and we moved on. We've been really good about communicating about sex so far, and he knows it's going to require some preparation for me. (Side note: I can use tampons without issue, although the last time I tried to put one in, I couldn't, but I'm assuming that's a fluke because I've been using them for nearly two years without problems). I won't be seeing him again until summer or possibly April, and I would really, really like to be able to have PIV sex when we do see each other. I know it's not the end-all, be-all of sex and there are plenty of other things that we can - and do - do, but I'm just afraid that maybe because of my first painful experiences I may have developed vaginismus and won't be able to have PIV at all.
So basically I am asking - what can I do in the next few months in order to become more comfortable with having PIV? I know It's something that I want but thinking about the pain is an instant turn-off. When he can't get in I just get more nervous and frustrated and feel sort of broken :( I know that I'm not, but it's frustrating! And I don't really touch myself very often, I find masturbation kind of pointless at times because I don't orgasm. If I've ever had an orgasm I didn't notice! So any advice on that would also be good, if you have any to offer!
Thank you very much for reading.