I think one of the most common misunderstandings related to penis size insecurity is the assumption that it is about whether or not you are physically pleasing a partner. I think more often than not it is not an insecurity based on whether or not you can please someone, it is more about your own sense of masculinity. The penis, unlike any other body part on either sex, is intrinsically associated with a personal sense of masculinity. People can say "it shouldn't be a measure of masculinity;" but it is. Think of all the jokes referring to someone's "shortcomings," (even David Niven Academy Awards comment about streaker recently played in media) or mentions in advertisements or movies/TV shows implying the sports car comments like "I wonder what he is trying to compensate for." Especially if you have a small flaccid penis that even grows average - the teasing you got in junior high shower situations stay with you the rest of your life. Women generally don't tease as much but it is actually becoming more common to equate largeness as sexually more appealing than it used to. Men on this site comment how masculine it makes them feel just to know what is in their pants. Note the recent Details article talks about the confidence gap between those with large penises vs. average/small guys. So again, I don't think it is an issue of pleasing the other - it is more about your own sense of masculinity. No matter how many times someone says "but it doesn't define you so don't worry about it," it is hard or even impossible to turn those thoughts of insecurity off. Not one woman ever complained about my penis. In fact, one even said "what do you call him - Mr. Big?" even though it is only 5.5 inches. Although that has been somewhat re-assuring it really hasn't done much of anything to really affect how I feel about the whole thing because again it is more about the penis being, in effect, a measure of masculinity that has pervaded our collective thought process. There are no easy answers. I think there is some of us that don't want sympathy, easy answers, nor denial - I think we just want to be understood. We have our own reality to deal with and have our own ways to deal with it, but it helps to be listened to and to be understood.