Almost exactly the same situation with my ex girlfriend I dated for 3 years when I was in college. I was her first and She HATED any contact on her clitoris (I tried it all as gently as humanly possible) but it was very uncomfortable to painful. She enjoyed sex a lot and was amazing, but never could orgasm. I thought maybe it was about endurance so I went 2 hours once thinking maybe 30 min wasn't long enough. But no crossing the finish line. I wasn't sure if It was something physical or just to much pressure but I'm sure she was frustrated. I felt bad for her and did everything I could to be supportive but there is only so much you can do. Sadly, she just accepted it as never going to happen. Now that I am older I think it was more about the abuse (a psychological issue than physical). An adult made her and her male sibling abuse each other around 8-10 years old. To make it worse her parents blamed her and sent her to "confess" at church and then told her she could never talk about it again. Sorry I don't have a solution for you. Just do everything you can to help her enjoy herself and not feel weird about telling you what she wants and enjoys. The stats are like 1 in 3 girls are abused (SHOCKING there are that many sickos out there) so that may play into it also though if that's the case she will tell you when she is ready.
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Use it for a while and while it’s desensitized stimulate it, so that the discomfort can be retrained In her mind as a pleasure like it normally would be.
If it didn’t help my other idea is restrain her. With permission of course. But full bondage. And make her pee. During the process you have to be very well Intune to your partners needs. But I believe from what was described, she needs a release of control to release that orgasm.
My girlfriend finds that it tickles, so she loses her sexual thrill. And squirms and wiggles. It’s like a shock to her nerve system that overwhelms her and makes her feel the need to pee, I held her down forcibly and kept going feeling the convulsions in her body. When she did finally break passed that point, she told me after she never had an orgasm before like that in her life. And she immediately fell asleep. When normally she goes about her evening routine after. I had done it for sure. And I think the part that helped her was that she had no control. And so she finally “ let it go” when I talked with her about it. She was happy about it, but still finds her overly sensitive clit to be very ticklish I’m not hung like a horse and I’m not mega skilled sexually either. But I listened to her body language cuz her words were not clear. And that’s what I got.
Good luck
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It is great that your bf is so caring and wants you to enjoy the sexual arousal. Not many guys do that and guys can be very selfish without being aware of how they only satisfy their own needs without any concern for the girl.
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