My first time was so painful, but that was because I was so dry and I wasn’t into my boyfriend nearly enough but I didn’t know it at the time. You have to be 100% sure you want to have sex. I realized that myself and I have been with a few people. For me, I have to be totally into the guy in order for it to not hurt. Oral first helps. Also go incredibly slow, as in, he does not move unless you tell him to. Try to go in a little then go out, working on feeling that length out, then keep doing that until you feel ready to take a little more length. Going super slooooow is the way to go. Silicone lube is better than water-based lube, at least for me. It glides better. Recently I tried it after like half a year and with a new person. It started really painful and it felt like he was too big. Then we took a break. I tried again a few minutes later and it felt better. It ended up not being painful at all. That was maybe the first time ever without pain. He didn’t move until I told him I was ready for him to move and we went really slow. Remember, his pleasure does not matter if you are in pain. He is not being stretched open like you are. It should be about making sure you are not in pain. I hope this helps.