I met this guy a few months ago (well, actually over a year ago, but we didn't realize that until last week) and we started a long-distance relationship. He moved to my city for work and we started real life dating a few weeks ago. I don't find him that physically attractive, but he is nice, we share interests, he is sweet and principled and treats other people with kindness and respect: He's basically an awesome person. He also has personal endorsements from people I respect, is semi-famous in our shared community for his work, and I could go on and on.

But. (And you knew there was a but.)

I had been looking forward to some sexy times with him, but had been taking it slow because I suspected he might be a virgin. Then a couple of dates in he brought up sex and assured me that he was experienced and competent and had done all of the kinky things. Cool! I speed things up. More kissing and clearly stating that I'm ready to go forward. No below the waist stuff though because of many reasons. A couple of dates later we go to his place. He says that it has been a while, so we start slowly. I now (belatedly) ask how long it has been. SEVENTEEN YEARS. Also only two other people and probably only a few times each. Okay, I can work with that. Lots of touching. He is teachable. My hand strays south of his border. At first I can't find his penis. It is flaccid and tiny. Really tiny. Nothing happens. He is apparently terrified of teeth so oral is out. I show him how to get me off manually. His fingernails aren't trimmed.

It wasn't a total disaster, but I feel really deflated. I had a long marriage which included very little sex, but what there was was good. I've had lots of partners. Literally more than ten times more partners than my new beau and hundreds of times more experience. I've had lots of good sex and a little bit of bad sex. But I was really counting on something at least semi-competent with this guy. Or at least some first-time enthusiasm. He is so awesome in every other way, but penetrative sex is important to me, and I can't get around that. I can work with small assuming he is big enough for penetration, and frankly I'm not sure that he is. (Seriously.)

This makes me feel so sad and shallow. Has anyone here managed to make a bad beginning into something sexually awesome? I am going to work at this and see if we can't improve it, but I'm really feeling deflated.