I’m a hetero male in my late 20's. I have a smaller dick. It’s not a micro-penis, as it’s around 5", maybe 6". I honestly don't mind that aspect of it—whatever, it’s “average,” right? The issue for me is that I am 6'5" tall, and thickly framed and naturally muscular. I'm apparently "really hot," as I’ve been told since my teen years, and if girls are interested in me, they are quick to incorporate my height into their flirting, and sometimes taking the innuendo further. Basically, women have a preconceived idea of what they’ll be getting when I drop my pants.

I’m in a long-term relationship of eight years with the girl I love. I’m going to marry her soon, and we’re going to spend our lives together. She loves my dick, she begs for it at times, and she has never made me feel bad about it. I feel...

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...totally comfortable with her—although, it took a few years to get to this point.

A year ago she gave me a few “hall passes,” permission to mess around with other women once in a while, yet my insecurity has led to me not using a single one. It sounds amazing—it sounds thrilling—to experience sex with other girls, after going through my 20's being completely monogamous. But I can't get over my fear that when the pants drop, there’s going to be disappointment, or even worse, mirth, and that it won’t be concealed.

I have the go-ahead to fuck new pussy but my own head is holding me back. This is excruciatingly frustrating. Again, it’s not having an average sized dick that I mind, it's being a giant guy with lots of muscles but an average sized dick that’s frustrating me.

Please Ease Numbskull’s Intense Sensitivities

Your letter brought back fond memories of one of my first boyfriends.

Jonathan was short and slight, with a gorgeous mop of blond hair, a dazzling smile, big blue eyes—and, boy, was I ever surprised when his pants dropped. That boy was hung like the proverbial horse, if you’ll forgive me for mounting a cliché (it's Friday, it's late, I'm zonked). He often joked that the energy and stardust others guys' genes sank into building bones and muscle, his genes sank into building cock.

And you know what he wanted more than anything? To be taller, to be more muscular, to have a bigger frame. Because it was way easier for bigger, taller, more muscly guys to get laid, and to be taken seriously as tops. Guys made assumptions about him based on his short stature and his slight frame—must be bottom, must not have much downstairs—and it drove him nuts. He would’ve gladly sacrificed three inches, or a little less 30% of his dick, to be six inches taller and a lot more muscular.

Anyway, PENIS, I'm not what I can do for you besides... maybe... send you some of the hundreds of letters I've received in the last few months from distraught guys with micro-penises maybe? Reading their letters might help put your "problem" into some sort of perspective.

So you're average in the cock department, dude—at "maybe 6'," you're technically above average—and, yes, you might have to deal with a moment's awkwardness when you drop your pants and it turns out your dick isn't quite to scale. But there's no sex without a little awkwardness. Power through that moment of awkwardness and show all that new pussy what that dick of yours can do. And if the sight of your dick really does disappoint, the sight of your thick frame and all those natural muscles and your height should more than compensate.

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