Hi chirochiro, and welcome to the boards
I’m sorry to hear you’ve had these painful experiences when trying vaginal entry and that it’s been a source of stress for you.
When you’re experiencing continued pain with insertion like this, it’s really helpful to consult with a gynecologist. Conditions like vaginismus can make the pelvic muscles tighten involuntarily and cause pain and difficulty with insertion, and can be helped with gentle exercises and pelvic floor physical therapy; too, a micro perforated hymen (where it covers more of the vaginal opening) can also cause difficulty and pain with insertion. In these cases of continued pain, a gynecologist will be the next step forward.
I would also not attempt vaginal entry anymore before seeing a gynecologist. We don’t want to keep trying something when it’s painful each time, as our brains can start to associate vaginal entry with pain. Know what I mean?
When you saw your doctor and they said you may have PCOS, did they advise you on anything regarding any symptoms you’re having, or refer you to a gynecologist?
My main recommendation is, if you’re concerned about pain with insertion, to consult with a gynecologist. I would tell them everything you’ve told us, including your medical history and possible PCOS diagnosis. They can help you with any symptoms you’re having surrounding periods that may be uncomfortable, as well as pain with insertion. Is that something you’re able to do?