Bleeding after sex.

Hello. i am an 18 year old female. i have been masturbating (i've used different things, mainly my fingers) for 14 years, and have used tampons. Three days ago, we tried having sex. He used a lubricated condom, but i was also really wet. He tried penetrating and it wouldn't go in. We tried a few times, but then i realized that i was bleeding everywhere, so we stopped. There was blood all over the outside of the condom (so i know it was me), there was blood on his legs and blood on my legs. i gently wiped myself with toilet paper a few times, and the bleeding lightened up a lot. Then i took a shower and washed myself. After that, i stopped bleeding. i spotted for about 19 hours after that. Last night, we tried to have sex again. He barely put the head in and i started bleeding again. It wasn't near as much as the last time though.
i am wondering why i bled. i had never had vaginal sex before, and neither had my boyfriend. i considered that maybe i broke my hymen, but i have masturbated for so long AND have used tampons, so i don't think that's it. Does anyone have any ideas??...i'm a little worried.