I recently lost my virginity and well the first time doing it, it hurt but the pain wasn't unbearable mind you i was slightly inebriated. The first time having sex I bled quite a bit so I'm guessing it meant my hymen was broken. However me and boyfriend went to have sex again the next day and I did want to. There was foreplay and lubrication but when he put his finger in, it hurt a LOT. He couldn't get it in more then maybe and inch and a half. So he tried again this time with more lubrication and he got in and stayed there for a minute or so but the pain was still there. I was really frustrated because I did want to do it so we kept trying when he finally made enough to room to penetrate me the pain again was almost unbearable. He stayed in me for me a few a minutes and the pain was fading however it felt nothing like the first time and I kept getting really tense. We tried different positions but nothing really worked. I guess I felt guilty cause I didn't wanted to disapoint him which added more to my tension. I'm worried there's something wrong down there because even now it feels uncomfortable and painful to put a finger in. I was also diagnosed with PCOS a year ago and I'm taking Novo-Spiroton as well as birth control. I don't know if the PCOS is relevant to the problem.