Why is she crying???

I have a friend whom I've known for 9 years. We've seen each
other through a lot over the years, and although we've never
officially dated, we've often flirted with the idea. The
first time we tried to have sex was about 5 years ago. I was
reluctant because I didn't have a condom and she ended up
crying, saying that I should have known this was going to
happen. We tried but the wasn't loose enough, and we ended
up falling asleep. The next time was last summer, we ended
up drinking together and things got out of hand. I had this
"prolong" condom I friend of mine told me to try but after
I put it on I couldn't stay hard. She took it personally and
though I wasn't into her and she ended up crying. I ended
up rolling off the condom and eventually got to the point
where I could cum. The last experiend happened a few days
ago. We went on a trip together and again had a few drinks.
We ended up messing around and she tried to put it in but she
wasn't wet enough. So I tried to go down on her but she isn't
really comfortable with people doing that so she pulled
me up so she could put it in her. Well we tried but she still
wasn't very moist and sensing that I started to lose my erection.
I pulled out and she said she couldn't do it and started crying.
She said she really wished we could do it but it never works
out. She went on to say that she seriously is attracted to
me and get excited by me, but when it comes time to act on it
her stomach knots up. I want nothing more than to be able
to please her and I'm extremely attracted to her but like
she said, it just never seems to work out. She mentioned
she ends up crying every time and if we kept trying and it
happened again she'd probably want to avoid me out of embarrassment.
I personally think we just want to please each other so bad
we're too self-consious. Does anyone have an opinion?

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