I am 25 years old and just lost my virginity two months ago to my boyfriend of eight months. I expected some bleeding and for it to hurt the first time or first couple of times, as I've read that's fairly normal. However, it's two months later, and we've had sex probably about six times now, and it still hurts, and I still bleed during/afterwards. My boyfriend is very patient and understanding with me, and generally it only hurts when he first penetrates me. Since it was hurting so much in missionary, he suggested trying with me on top so that I could be more in control and "go at my own pace," which actually has worked really well. It still feels like I'm being stabbed in between the legs while I'm guiding him into me, but if I just kind of sit there for a minute or so and "get used to" the feeling of him being inside me (usually he'll touch other areas to help me relax), then it starts to feel okay and we're able to proceed to getting it on (and it feels great and completely painless once I'm at that point, and I'm usually able to orgasm from it fairly quickly).
Then the really unnerving part comes. Once we're finished and he pulls out, there are usually traces of blood on the condom, and once I go to the bathroom I wind up seeing red blood or pink traces on the toilet paper and sometimes in the toilet water. Like I said, I expected blood the first time, but not after two months. I bleed every single time though, even when I am super turned on and lubricated. We always use lube, even when I'm really naturally wet (we usually spend a lot of time on foreplay), so I can't see it being a dryness issue. He seems fairly well-endowed to me, especially girth-wise, although his is the only real live penis I've ever seen in person, so I don't have much to judge it on. Since it only hurts when he first penetrates me, I tend to suspect that maybe he's tearing me at the opening because he's larger and I'm on the smaller side.
Has anybody else had this problem? I don't know if this is something that will go away in time since I'm still kinda new to sex, or if this is something I should really be concerned about. I intend on making a doctor's appointment to get checked out, but I'm really nervous about that because pelvic exams have been notoriously difficult for me in the past, even though my doctor is totally great. I'm just getting really frustrated with this, and any advice or words of wisdom from other people who have experienced this would be great. Thanks, guys!