Letter From Milo: A Shameful Episode

September 4th, 2019

The high school I attended was blessed with an abundance of beautiful girls. Everywhere you looked there were long-legged teenage beauties, with angelic faces, fine butts and perky young tits. It was a paradise for an aspiring pussy magnet (see appropriately titled post). I spent most of my high school years walking around with half a hard-on.

The best looking girls in the school were the Anderson sisters. They were every young man’s fantasy, beautiful, poised and shapely. I’m sure they were responsible for the vast majority of soiled sheets in my school district. I know that my laundry bills skyrocketed.

Ordinarily I wouldn’t have hesitated to approach one of the Anderson sisters, maybe invite one of them to see a movie or go to a school dance, then, afterward, hope to get extremely lucky. But, to my eternal regret, I never did ask one of them for a date. In essence, I chickened out.

You see, there was a problem with the Anderson sisters. They were African-American and I was not. And in Gary, Indiana, the racial divide was a wide one.

I was a freshman in 1964, when my high school was integrated. To say the least, it did not go smoothly at first. There were fist fights nearly every day, tough blue collar black kids and tough blue collar white kids beating the shit out of each other to prove, well, who knows what they were trying to prove? There were police cars parked by the school every day to keep the violence from getting out of hand. Not that it mattered. When young men want to fight, they generally find a way.

In time, however, things settled down. After school brawls became rare as the black kids and white kids began to accept each other. Tentative friendships were formed that often turned into genuine friendships. Black and white jocks began hanging out together. Black and white misfits began drinking cheap beer and smoking Lucky Strikes together. And black and white nerds probably got together to practice their slide rule chops.

But the one gap that was never bridged was interracial dating. It was too much to ask in the mid 1960s. I don’t recall ever seeing a black and white couple walking the halls of my school and holding hands. I don’t remember ever seeing a teenaged black and white couple out on a date. It just wasn’t done.

Now, you’d think that a legendary pussy magnet like me would be the one to break the interracial dating taboo, especially with a prize like the Anderson sisters at stake. I mean, let’s face facts, beauty is beauty, no matter what kind of package it comes in.

But no, the great Milo, in his teenage years, didn’t have the balls to do the right thing — the right thing being taking my best shot at the best looking girls in town. I had let down pussy magnets everywhere.

Would Errol Flynn have hesitated? Would the immortal Porfirio Rubirosa have given it a second thought? Would a beautiful woman’s skin color have mattered to Warren Beatty? No! But young Milo couldn’t come up with the goods when the occasion called for greatness.

It is a failure that haunts me to this very day.

Times have changed. We have all moved on, even the Anderson sisters. One of them, with a slight name change, became a well known entertainer. I don’t know what happened to the other sister, but I assume she did well in life, too.

As for me, I became a famous and highly paid blogger here at The Third City. I spend my days thinking deep thoughts and my nights wandering the streets of Chicago. And whenever I see an interracial couple, and I’m glad to say I see them often, I curse myself for being the worst sort of idiot, a disgrace to pussy magnets all over the world.

How did I ever let the Anderson sisters slip through my hands?

Pussy magnet, my ass.

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