Unable to have sex /u/ExcitingBus7684 Sex

I’m 21(F) and I’ve never used any sex toys before. My boyfriend and I have tried having sex three times with no success. The first time we did it, barely a portion of his dick could enter before he felt me resisting him. It also started to hurt for me. According to him it felt like I was tightening myself and trapping him so he couldn’t move any further. (Keep in mind I was wet and we used regularly lubricated condoms) The second time, (another day) only half of it entered after which it started hurting for me. Again he felt a sort of resistance as if I were clenching my muscles or there was some barrier. The third time, (another day) after half of it entered it started to hurt again and he felt rhe same resistance from me, even though I was turned on and ready for it. We stopped and after a while I saw there was blood on my underwear. How do we go about this and how do we successfully have sex😭

I’m 21(F) and I’ve never used any sex toys before. My boyfriend and I have tried having sex three times with no success. The first time we did it, barely a portion of his dick could enter before he felt me resisting him. It also started to hurt for me. According to him it felt like I was tightening myself and trapping him so he couldn’t move any further. (Keep in mind I was wet and we used regularly lubricated condoms) The second time, (another day) only half of it entered after which it started hurting for me. Again he felt a sort of resistance as if I were clenching my muscles or there was some barrier. The third time, (another day) after half of it entered it started to hurt again and he felt rhe same resistance from me, even though I was turned on and ready for it. We stopped and after a while I saw there was blood on my underwear. How do we go about this and how do we successfully have sex😭