27 Mar I'm a virgin, and the first time my boyfriend inserted his fingers in my vagina, it hurt a lot, and I got sore down there. I didn't reach an orgasm, but faked it so he would stop. I didn't enjoy it at all and I was wondering is this going to happen when I have sex? Is it going to be as disappointing? — Touched by a. 29 Mar Is it normal to have extreme pain when a penis is entering but not yet completely penetrating a vagina? I tried to lose my virginity twice in my life and both times this happened. The first time I had a very small amount of blood (this was last year) although I thought because it hurt extremely bad maybe he just. The “pain of virginity” is largely a myth, almost as much as virginity itself. You are very likely not to feel pain at all while having penetrative sex for the first time. First of all, you need to understand what is the hymen. During foetal devel.