I'm a virgin and the last two times that my boyfriend has masturbated me I've bled. The first time that he did it I didn't feel the blood at all, I felt werid a little bit later and when I went to the bathroom and there was a lot of blood and I knew it wasn't my period. I thought that he broke my hymen, don't know if I'm right obviously. Also, that are hurt like for two days after, then it went away. After that, I thought that I wouldn't bleed anymore because well, he broke my hymen. But, yesterday he did it again and when I got home there was blood but, very little in comparison to the last time and it hurts a little too now, less that the last time. What's happening?
He can be scratching you or just causing damage due to friction. It can also bleed a few times as he breaks your hymen with his finger. Next time take a mirror and look if you see anything. If it is your hymen, you should be able to see the tear and the bleeding.
He should groom his fingers and make sure there is nothing edgy or sharp. He should also not be fingering you rough. Your sexual pleasure comes from your clitoris. That is where he should concentrate most of his effort. Tell or show him how you do it yourself. That way he will know.