Insecurity regarding (sorry)... penis size... ugh
There is a woman that I'm kinda interested in, and she is constantly flirting with me, hinting that she wants more than to just be friends, and being sexually suggestive. She often brags about her libido, etc, and how she is really good in bed.
Well, I am—or shall I say—WAS, just a stone's throw away from giving a relationship a try (holding hands, cuddling, first kiss, etc), until something happened. I was flirting with her, and pretending to have a condom in my pocket, when in fact it was a poker chip. I just flashed it really quickly and said, "Guess what I got when I was on vacation?" Soon she realized it was just a poker chip, then said, "Wow, if that were a condom, that would be really sad." Now, I know how large a rolled-up condom is, and the average one really is about the size of a poker chip. So I felt badly because I'm not really large (only 4.3" long and 4" around). I quickly said, "Well, if you think that's sad, if it were a condom it would fit me just fine." I said this to kind of break the ice that I'm not big. She just quickly said, "Whoa, TMI."
Then, later that very evening, we were alone talking at her place, and somehow the conversation of "size matters" came up. She said, "Oh, that what guys like to say (referring to 'size doesn't matter'). Girls just say that it doesn't matter to make guys feel good. It matters, honey."
Wow. That certainly took the sails out of my desire to begin an intimate relationship with her...and my self-esteem. She basically, without knowing it, called my size "sad." I have been severely depressed over this for two days. If I ever did get intimate with her, I would feel insecure, like she would laugh at me (at least on the inside).
She cares about me a lot, and we've shared a lot about each others' personal lives. I know she wants to start a relationship. Problem is, she HAS noticed that I've been depressed the past couple of days, and she wants to know why I'm so glum. Gosh, do I tell her? "Hey, when you made those remarks, you made me feel so insecure. Why? Because I really am below average, and you already told me that 'size really does matter' and implied that a regular sized condom is 'sad.'
Here's a shocker: we're both in our late 30's. I know this might seem juvenile for me to be posting this at my age—perhaps you'd expect this from a teenager—but feeling are feelings, and men are insecure about this at any age.
How do I handle this? If I tell her, it will be super-awkward for both of us. If I don't tell that what she said hurt me, I can't clear the air about an issue I am insecure and depressed about.
I welcome all advice, especially from women.
Please...no hurtful posts. Thanks.