when will sex stop hurting? I've recently had sex for the first time and we took things nice and slow and his penis is a normal size nothing to big and I get nice and wet but still loosing my virginity hurt. how many more times before it starts to feel pleasurable? like the 5th time or the 10th time maybe??? hes so sweet and trying his best to be careful with me I just want it to stop hurting some. when will that be??? just looking for a round about time it felt BETTER😉