I'm in my late twenties and, like several of you, have never been all the way with a girl. Since the onset of puberty I've been severely depressed and hated myself to much to love someone else.
But now I've left my awkward stage and I'm gorgeous (not my words). So, I took a co-worker out on a date a week ago (bad idea, I know.. and she's not even a peer). She's not the youngest or most stunning that I could have had, but she is young and stunning. Despite needing two hands to count how much younger than me she is, I'd run out of fingers and toes before I could tally the experiences she's had (not all of them men). After one and a half dates, we have shared all this with each other, the sordid details of her most shocking sexual encounters and my most personal issues (which I have never shared with anyone). But she appears as ashamed of her sexual history as I am of my lack of one.
Even though I would like nothing more than to get her in my bed, I have not pushed, even though she may expect it and may do so, because I don't want her to think she must or that I'm like all the other men in her life. On top of this, I learned half way through. That's not even the half of it, but I'll stop there. And despite everything she's told me about herself, I like her more.
Can this possibly end well? How?
Am I too respectful of women? Or just this one?
Has anyone been in a more extreme situation?
Any words of encouragement, criticisms of my poor judgment, or similar experiences are welcome.