Hey there, whenever I try to masturbate it doesn't work. I've tried putting my cell on vibrate and holding it against my stuff down there, but that only gives a vaguely pleasant feeling, but when I try to put my fingers inside it just hurts a lot -- I've only ever been able to get my little finger in and it hurts. I have no idea what an orgasm feels like and I don't want to hurt myself down there 'cause based on my experiences I think I must be sensitive down there. So can anyone give me some general tips on how to get two fingers in there and how to (feel good about) masturbating, climaxing, etc...? In case it's not obvious, I'm a virgin and I'm 20 years old, so I'm feeling really helpless about all this.
I think the reason your feeling pain could be you are feeling anxious when you masturbate and that is causing you to tense up causing your tightness.
If you would like more help feel free to msg me :-)
OK, forget about "getting fingers IN there" and start experimenting with "fingers on there", if you want to know how to climax. You really want to play with your clitoris, which by the way is much bigger than the externally visible portion would have you believe. Just rub it with one or more fingers, at different speeds and different ways, and see what gets you aroused. You don't ever have to actually have vaginal penetration to achieve an orgasm, though some women enjoy having something in there even during masturbation. It's all up to you. Just take your time and give yourself the chance to learn what your body likes. :)