P.S. I did just go to the doctor to have them check for signs of any infection, however, I did not mention the pain.
Answer: I am not sure what is the cause of your pain, but I suspect something is putting tension on the ligaments that attach to your clitoris. The round ligaments connect to your uterus on one end, and to your vulva on the other, passing over the pubic bone and under the pubic mound in the process. The clitoral suspensory ligament has two layers, an outer that extends from the fatty tissue of the pubic mound to the clitoris, and an inner one that attaches to the clitoris and pubic bone, at the base of the clitoral body. Several muscles anchor to the clitoris. Look at the illustrations in the first book listed in the Anatomy section, A New View of a Woman's Body.
Something to consider is whether body position affects things. Do you require a lot of thigh tension to experience orgasm? What happens if you masturbate and experience orgasm with legs together versus apart? What is the state of your pelvic muscles? Can you insert something into your vagina? Perhaps a massage or physical therapist could help out. Your pelvic muscles could be strained or things could be out of alignment.
I highly recommend you talk to your doctor about the pain. I would hope they are professional when dealing with sexual issues.