I have been afflicted with the stupidest insecurity possible, insecurity about my penis size.

Many months ago--in response to my stupid question "Would my penis please you more if it was bigger?"--my very sexually inexperienced girlfriend said, "Maybe, yeah. Why? Can you make it bigger?"

Turns out that when I asked that ridiculously loaded question we were both in the midst of our own insecurity attacks. I was feeling insecure about... penis difficulties, including often being only partially erect due to hormonal issues (fucking thyroid), and she was feeling insecure about her lack of sexual experience and the fact that she's never experienced a full-fledged orgasm.

She said at the time and has said since that her answer came primarily out of insecurity about not cumming. But she's also said that she can tell when I'm not fully hard and, yes, it doesn't feel as good as when I am. Makes sense.

Unfortunately, through these various discussions I've also learned that of the four guys she's slept with in her life, two were evidently quite well hung. One of these well-hung ex's still lives on her street--not sure why that's relevant to me but it is.

So in my mid-30s (gf is close to my age too), I've suddenly developed a preoccupation with penis size. I've measured myself three times (sadly) and each time the measurement is the same: 7 inches length, 5 inches girth.

I admit it, it bothers me that my otherwise okay-sized dick is evidently small in comparison to her ridiculously skewed, er, sample. I don't like hearing the word "fine" used in relation to my dick. And it worries me that she doesn't have enough experience to really know for herself if she needs and wants a huge cock.

But she is inexperienced. She says that this is her first real relationship, and she’s never had a guy ask her what turns her on before or want to talk about sex... or ask her much about anything. She says she feels ashamed that, in her mid-30s, she knows so little about her body and what turns her on.

And, I guess if I put the penis size thing aside for a moment, what’s really bothering me is that I’ve tried really hard (can’t get away from the puns) to coax her into taking a more active role in her own sexuality… and she doesn’t seem to have explored much after nine months. I’m the first guy to encourage her to touch her own clit during sex—she tries it and then stops, saying it feels like too much to focus on. She bought a sex book, told me about it, but I was the one to go find it and remind her we could read it together—I ended up reading it alone. I bought her a vibrator and while she loves it she only uses it when we’re together. I’ve encouraged her to masturbate and she recently revealed that she’s only solo masturbated twice in our nine month relationship.

And her lack of initiative leads me to focus on me and my performance and the few things I have gotten feedback on, such as "your cock is nowhere near as ginormous as the guy who lives next door." Okay, I'm paraphrasing.