This flies into a lot of popular thinking that the more a guy thinks about his penis, the more he will develop insecurities around it. I disagree.
Fear and insecurity doesn't come so much out of a believe of inadequacy...it comes out of a belief that you might be inadequate and that being so would be difficult a reality to suffer. Fear is always proportional to the gravity of what there is to lose. That's why the scariest thing to happen is someone to threaten your life. Similarly, the fear that you might be inadequate and that you couldn't handle it is in someway akin to fearing you'd die and so you grow more and more anxious about it.
But what if you just accepted that whatever the outcome you could handle it? You wouldn't be worried...you would just know. And if the answer wasn't what you wanted...well, at least you could make progress towards acceptance, rather than continuously fearing the thought.
Yes, I know that it doesn't actually matter past a certain point how big it is. That has nothing to do with what this is about. This is about a man's insecurity that his symbol of masculinity pales into comparison of what he'd like it to be. This is about not introducing fear to an act that should be all about pleasure and love.
Another reason it's important for a guy to measure is because it's honestly one of the things that can easily appear as optical illusion. By this I mean, for instance, if it's fat it will look smaller from a distance than the same lengthed but skinny one would look like much like a tall thin man will appear taller than a tall fata man at first glance. Also, if you work out a lot and have big muscles it will look bigger. If you manscape it will look bigger than if you are really hairy for obvious reasons. The point though is that once you measure optical illusions no longer matter because you know the truth.
And to share my own personal story...I always thought I was average until I was 17 and finally measured and found that I was really big compared to 6 inch average. We always assume things will be worse once we find the truth, but often it's better than we imagined.
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