How to figure out what girlfriend likes?

To give a little bit of a context on me: I'm nearly thirty, started dating at around 26 and got into my first (and current) relationship only about two months ago, so I'm a little bit "behind", which sometimes can unfortunately make me feel insecure. Now to the question:

My girlfriend is amazing and I enjoy that we have a very open communication in our relationship. There is unfortunately one exception and that is when it comes to being intimate more specifically to her wants. She's happy to discuss with me what I like, but when I ask her about what she likes, she suddenly becomes very shy and does not share much with me. I usually just do things that I enjoy like very tight hugs, kissing on the neck, sneaking on her and hugging from behind etc... Whenever I ask her what she enjoys, she just goes with the same answer that it's everything I do. It hasn't really been much of a trouble so far and we are both very happy with it, but recently we have gotten to a point of mutual masturbation and well... there her lack of feedback makes things difficult for me. When it was my turn to use fingers/hands to pleasure her she just told me that she never masturbated (which in in on itself I find it difficult to believe) and well that was all I really got out of her. Doing this for a first time it left me clueless: So I started kissing her while doing things I hoped she would like with two of my fingers between her legs. She definitely enjoyed it, but I doubt she was even close to orgasm and well it just feels disappointing as I'd like her to feel as good as I do when I'm with her. Any thoughts on what should I do?

If she doesn't express you need to be mindful of her body language. For example moans, changes in breathing and "wetness" down there. Caressing the clitoris is something many women love, especially in circular movements, but you need to find the right pressure, it can't be too much nor too little. Also she needs to be relaxed and comfortable, but she doesn't seem to be very relaxed when the subject comes to sex. So I'd say watching her body language closely and try to make her comfortable to express herself. This doesn't mean you have to be always asking and pushing for answers.

Is she a virgin?

@Annia. I do not know for sure. She had two boyfriends before me, but does not like to mention them. I would have prefered if she wasn't as at least one of us would have a clue of what we're doing, but it's not exactly something I feel comfortable prying into. I guess you could say we're both kind of shy when it comes to sex. (She's just a more extreme version of me: that's why our personalities fit together. :) ). Also as of right now it doesn't really matter as either of us is far from ready for intercourse. Nevertheless I should probably look at her organ down there next time we end up in another session like that. I've been kind of doing it blindly as I was kissing her at the same time. It just didn't end up as I would have hoped for. I just expected her to show me a little what to do and I'd have taken it from there. Now it puts me in a bit of an awkward position, but considering she already played with my genitals (and frankly was very good at it), I feel like it's something I need to learn to reciprocate somehow.

I think it's good that you are willing to learn--keep that attitude and you can't go wrong. Remember that every woman is different, so figuring them out is not necessarily as straightforward as it can be with men. Many women cannot orgasm through penetration so fingering or intercourse would not be enough anyway to get the kind of reaction you may be looking for... this is why it's important to pay attention to the clitoris. It's homologous to the penis in a male. At the same time, don't take her lack of orgasm as a personal affront. Even if you were the best lover in the world, fingering wouldn't get me there and I know I'm not alone. If she truly hasn't masturbated before, then she doesn't really know what works for her or if she can come that way.

Many women have to be relaxed and in the right mental space in order to orgasm, so know that nervousness can also come into play. As you guys continue to explore and touch one another, she will likely become more comfortable. I do recommend going off her body language if she is not otherwise very expressive. Keep in mind that until you guys do figure out what works for her, she may still really enjoy the closeness of that type of intimacy even if she's not climaxing. Avoid the pitfall of putting pressure on her to O as that can also keep it at bay as well. Definitely find out where her clitoris is and start to concentrate some of your efforts there.

Just keep learning about each other in a comfortable, private, relaxed setting. You are right not to pry about her past. Annia's advice above is excellent with regard to becoming tuned into signs of arousal and enjoyment.

I'm 29 years old and hand on my heart, I never did anything to myself till about a year ago when me and my boyfriend was having intimacy issues. Women aren't the same as men, or most men. Men doesn't care that women know they play with them self or even care to express what they do or don't like. I'm very shy when it comes to the bedroom and I've been with my boyfriend for 12yrs nearly. As stated above already, listen to her breathing, her moans and her body language. Most women comes mainly from stimulating the clit. Again, gentle but not to gentle, circular movements. Try something called a /penis ring. It's a ring that goes around the base of your penis that has a little rubber thing that allows the rub her clit when your moving in and out. Mine is a rabbit o ring.

Your probably doing everything perfectly but some women needs a lil more. I only say probably because I don't know you :-)