Okay soooo ...

Ok so like I'm a virgin still and almost out of high school for good. And I've had a crush on this guy (who turns out to have a high sex drive for me like I do for him) and he wants me to send a video of me using a cucumber to fuck myself, however.... I'm still a Virgin.... I know I should tell him and I plan on it. But I've always had this thing where is rather take my own virginity instead of letting someone else do it. Can anyone help? Btw I'm on my period so I thought that if I bleed it would be okay but... Now I don't know if i lost it or not, it stung and I could feel myself stretching. Help!!