hi everyone, i'm 21F. there are two main issues i'm dealing with. not sure how to organize my questions, so forgive me.
so firstly, i've been masturbating for probably 11 years at this point, tried all manner of things. i took a break from masturbating for a few years due to finding it a little boring. started again within the past year due to starting testosterone and also getting a partner. it's fun, but doesn't really end in anything satisfying. i get a warm and tight feeling in my clitoris, and then it just kind of goes away. it's always been like this. is this normal? is it supposed to feel better than that? anyway, as i mentioned, i got a partner, and i was a virgin until two months ago. they have a lot more experience than me, but weren't able to make me orgasm, at least not in a normal way. just "that feels good -> oh ok done now". i don't know that it's a technique issue as nothing happens when i'm alone either no matter what i try. i can't shake the feeling that i'm disappointing them or ruining their self confidence, even though they claim otherwise. do you think i'll be able to fix this in the future?
secondly, the first time we had sex, i bled all over the bed for the whole night, but it went away by the morning. pretty light, but enough to mess up the sheets. we used lube, and stretching with fingers beforehand as well. when we had sex again, i bled again. same deal, lube and stretching, but i still bled. we've had sex a few times now and i still bleed every time. i don't know if they're going super rough or something, because i guess i don't have that much stimulation down there? but it doesn't hurt or seem particularly rough. oh, and i bleed from just finger fucking too. and i bleed whenever i decide to insert something while masturbating. i use lube every time and i really don't think i'm being rough. i don't even do it for longer than 5 minutes when i'm alone.
tldr; i don't think i can orgasm, and i bleed every time i have sex or masturbate vaginally. help?