Hello hello.
I'm a 23 year old male dating a 27 year old female. We have been a couple for 3 months and dated for a while longer.
In the beginning it was apparent that she was not going to orgasm easily. She told me that it was because she needed to get to know me better and trust me. I, of course, accepted this.
Now, 3 months later, we are madly in love and it has become apparent that having feelings are not the issue as she still has severe problems having an orgasm. When I brought it up, she told me that the issue lies in the fact that she is obsessed with her looks and how I view her etc. I can understand that and so I do what I can do improve her self-confidence and assure her that I find her very sexy in any situation.
But her vagina is what puzzles me. I've been with my share of women both in and out of relationships and I consider myself to know how to please a woman. As a matter of fact, pleasing the woman is my #1 priority in sex (as it should be).
Now, first of all what does work: She enjoys dry-humping the comforter. This is her #1 way of masturbating. She can sometimes reach an orgasm this way on top of me, with or without penetration, using the comforter to stimulate her clitoris.
However, there is not way to actually touch her clitoris for stimulation. I've tried warming her up thoroughly, but she simply does not enjoy being touched or pleased that way. It seems that the only thing that does the trick is a comforter around the area. I can touch her clitoris if I keep her labia over the clitoris (vagina completely 'shut'), but this does not bring her anywhere close to an orgasm.
She absolutely loathes being fingered. I've tried to stimulate her g-spot but she just hates being fingered so it's pretty much just off the table (I did heat her up beforehand in all of the cases where I attempted this).
Now another thing that confuses me is whether or not she enjoys being touched around the anus.
My experience is that a lot of women enjoy being gently touched and even fingered lightly in the anus during intercourse. I would gently work my way towards her anus and she would take my hand away so I didn't think no further of it...Then we both got drunk and I decided to try again and she moaned at me to finger her anus which I did and it gave her immense pleasure. When I do work around her anus she starts to orgasm but stops and takes my hand away so I'm thinking that the problem is, again, her self-confidence and not the fact that she does not enjoy it. I did ask directly and she claimed not to enjoy it..
Is this woman having such self-esteem issues that it is preventing her from having an orgasm all-together? All my ex-girlfriends have been very orgasm-friendly so I'm very new to this type of situation. How do I help her achieve an orgasm? I'm reading up on kama-sutra but most of the stuff there is pretty routine for my sex-life (didn't know that before I read it, though).