Okay, this is the million dollar question. IF someone here can figure this out, I'd honestly give you a million bucks if I had it! I made a post about this here about 1-2months ago, and tried everything in the replies but still no good, so here is my attempt again. I'll re-explain the whole situation so we don't need to go find that old post again. I've been going out with my current girlfriend for about 10 months now. She has never orgasmed before. We've tried -everything-!!! Oral, Fingers, Rubbing, Vibrators, Sex, Anal Sex, EVERYTHING! It came down to this realization: If she can't orgasm by her own means (masturbation) then chances are I'll never be able to make her orgasm. She's never orgasmed through masturbation. Here's what happens every time: It feels good for a bit, then she says it peaks and it just doesn't feel like anything anymore. She goes until she gets too tired, and then stops. Same thing happened when I tried or went down on her, it feels good for a bit, then she tells me to stop and pulls me away because it doesn't feel good anymore. Then we tried this: Every night before going to bed, we designated a good 20minutes to her masturbating, thinking that it just takes time for her to learn how. We did this every night for about 2 months, and it was the same result each time. Now, she doesn't even want to do it anymore because she's basically given up. I've caught her a few times in our discussions about this saying, very naturally, ".... yeah but i can't orgasm". It feels like it is her default mentality these days. I feel really bad for her because I want her to be able to orgasm! I don't know what else I can do, I have tried everything that has been said online: Give her time, take it slow, make sure she's comfortable, make sure she can bring herself to orgasm, don't pressure her, EVERYTHING! Now we're at the point where even SHE doesn't want to try getting to her 'O'. And that's not the end, recently we've noticed that when I enter her (with my penis or with fingers) it hurts, and I have to stop almost instantly (maybe after a couple of minutes). And it hurts/feels sore afterwards. This never happened before either :S Lastly, the last time we actually had sex, she got embarassed because she got extremely wet (soaked up the whole bed pretty much) so she has been putting that off too, and I of course don't say anything and I support her in every way that I can -- but I think this is becoming a really dangerous issue for her. I complement her in everyway, she knows she has a really great body (she runs 5k every morning on weekdays), and knows she isn't ugly or overweight, etc. The ONE thing she enjoys doing however, is something she says she's been doing since she was really young (~11-12 years old)! She wraps the blanket between her legs, and puts her hand pressing inwards from the outside of the blanket, lies on her stomach, and uses her legs to kind of push and rub herself against her hands through the blankets, and she says she can do that for hours if she could... it totally exhausts her and she moans like theres no tomorrow, and her heartrate goes through the roof. Again, no orgasm comes from this, and she can only do this about 2-3 times before she gets fully exhausted and then goes to bed. At this point, I've exhausted all my options. The only thing I can do is just wait and give her even more time, but how can I do that when even she seems to have given up? -A very saddened Jimmy.