Letter From Milo: Mickey Came Home…

September 6th, 2020

Mickey came home from Vietnam in February of 1970, just a few days short of his 21st birthday. He had been an infantryman, a rifle-toting grunt who had slogged through mountains and swamps, bombed out rice paddies and impenetrable jungles. He had seen and done things that no person should ever see or do. Some of the memories would never leave him.

Back home, Mickey was at loose ends. He didn’t know what to do. He was lost and confused. His old friends, high school buddies, seemed like childish strangers to him. He wasn’t sleeping well and was eating poorly. Even his mother’s cooking, which he had always relished, was tasteless to him.

Mickey spent most of his time in his car, driving aimlessly, listening to the radio and smoking lots of marijuana. Sometimes he’d pick up a six-pack or a pint of whiskey and drive out to the beach, where he’d find an isolated spot near the shore of Lake Michigan, park his car, and watch the waves roll in and out for hours at a time. The sound of waves lapping at the shoreline soothed him and often he would fall asleep, lulled by the rhythmic play of the waters.

Mickey knew there was something wrong with him but he couldn’t quite put his finger on the problem. The term Post-Traumatic Stress Disorder hadn’t been coined yet. If he had known about PTSD he might have tried to get some help, although Mickey was by nature a self-contained type and probably wouldn’t have asked for help even if he knew he needed it.

After being home for a few months, the time had come for Mickey to make a decision. He could either get a job in one of the local factories or do something else. He opted for something else. He decided to take advantage of the GI Bill and go to college for a year or so, just to clear his head. Maybe he would get a new perspective on things. Maybe his demons wouldn’t follow him to southern Indiana. Maybe he could outrun his past. Maybe.

His first months at college were not much different from the life he had been living in his hometown. Mickey wandered around in a daze, keeping his head down, unable to reach out to people, unwilling to expose himself more than absolutely necessary. He attended classes sporadically, spent time drinking alone in the local taverns and smoked pot to take his mind off of, well, who knows what. He may as well have been a ghost, his presence unnoticed except for those whose senses were attuned to the high and lonesome end of the misery spectrum.

And then Mickey met Bonnie.

She was a beautiful, long-legged art student, a farm girl from southern Indiana. She saw something in Mickey that he thought had been lost and gone forever. She saw a spark of intelligence, a glimmer of humanity that he thought no longer existed. For some reason she decided that he was someone worthwhile, someone she wanted to know better.

Bonnie took Mickey under her lovely wing. They became friends, and then they became more than friends. She had a kind and generous nature and, more than that, she seemed to have an intuitive sense of how to deal with Mickey’s damaged psyche. When he went into one of his funks, she knew how to lift his spirits. When he woke up in the middle of the night, drenched in sweat and gasping for breath, she soothed him with hugs and kisses and gentle words until he was able to fall asleep again. She was comfortable with his silences and listened patiently when he felt like talking. Although Mickey didn’t realize it at the time, Bonnie was exactly what he needed at that point in his life.

When Bonnie brought Mickey into her life she also introduced him to her world. As an art student, Bonnie’s social circle included other artists – actors, writers, dancers and musicians. Mickey, who was used to the rough world of soldiers and working men, found himself enjoying the company of his witty and creative new friends. They made him laugh and think and look at the world differently. He was changing.

Slowly, Mickey began to come out of his shell. He felt healthy again. He was sleeping better, too, his dreams less vivid and frightening. He took pleasure in good conversation, good music and even began enjoying some of his classes, although it must be said that Mickey had a low opinion of organized education. He no longer had a sense of dread when he woke up in the morning. He had the odd but welcome sensation that he was becoming a human being again, reconnecting to the person he once was and seeing intimations of the person he might become.

Mickey understood that none of this would have been possible without Bonnie. She had literally saved his sanity and, possibly, his life. She had lifted the darkness from his soul and replaced it with dawning hope. Mickey knew that he could never explain to Bonnie what she had done for him. He could not find words that adequately expressed what she meant to him. In fact, he doubted that the proper words of thanks existed in the English language. The only thing he knew for certain was that without her he might have remained a ghost, a blue-collar Flying Dutchman, doomed to spend eternity wandering. He would never forget what she had done for him.

All stories have a beginning and, sadly, an end. When she finished school, Bonnie decided to move to New York City to pursue her artistic dreams. Mickey’s future lay elsewhere. They went their separate ways, but Mickey always kept Bonnie in his heart, safely tucked away in a place where a person’s most precious treasures are kept. He thought of her often, wondering where she was and what she was doing. Always, when he thought of her, he wished her peace, love and happiness. There was nobody more deserving.

And there was absolutely no doubt in Mickey’s mind that when Bonnie thought of him, she wished him the same.

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Letter From Milo: Chainsaw Man

April 28th, 2020

A few years ago some rotten bastard broke into my garage and stole my chainsaw. It was a loss of staggering proportions. I have yet to recover.

Now, losing a chainsaw may not seem like much of a problem to the sissified, cheese-eating, ballet-going, opera-loving, Prius-driving readers of The Third City, but any real man will tell you that, next to castration, losing a chainsaw is about the worst thing that can happen to a guy. It’s like a Hell’s Angel losing his Harley or a bluesman losing his Mojo – the symbol of his manliness, the totem of his tribe is gone and a vital part of his spirit has vanished with it.

You see, over the decades and centuries, symbols of manliness are slowly being erased from human society. Trophy scalps are frowned upon, high noon shoot-outs on Main Streets are illegal in many municipalities, dueling scars are relics of another era, Detroit has not made a decent piece of iron since the GTO and high stakes poker is played by nerds on the internet. Even tattoos, which were once the province of sailors, circus freaks and wild South Sea Islanders, are as common as braces at Chicago’s Latin School.

In my opinion, the only remaining symbols of masculinity are power tools.

And the unrivaled king of power tools, the epitome of macho-osity, the defining symbol of manhood, is the almighty chainsaw.

Some of you may say, “As usual, Milo, you don’t know what the fuck you’re talking about. A gun is much more of a masculine symbol than a chainsaw.”

Bullshit! The only thing a gun is good for is killing people and animals. You can’t cut down a tree with a gun. You can’t clear brush with a gun. Plus, has there ever been a better horror movie prop than a chainsaw? There is absolutely nothing better than the sound of a chainsaw sputtering into action for scaring the shit out of a bunch of horny teenagers camping in an isolated spot in the north woods.

Back in the days when I was still a proud chainsaw owner I would look for any excuse to use it. If there was no reason to use it I would take it out of the garage and mess with it – clean it, change the oil, check the spark plug. The smell of the chainsaw, a combination of oil, gas, grease and sawdust, was intoxicating. It sent my testosterone levels soaring.

Then when I was satisfied that it was in top condition, I would pull the ripcord and start the bad motherfucker. When it roared to life, the vibration of it ran up my arm, through my shoulder, down my side and settled in my nuts. It was beautiful.

I was a wreck in the days and weeks after my beloved chainsaw was stolen. I couldn’t sleep, I couldn’t eat, and my already considerable consumption of alcohol and drugs tripled. The lovely Mrs. Milo, always sensitive to my every mood, and tenderly solicitous of my well-being, was worried.

“What the hell is wrong with you!”

“You wouldn’t understand.”

“Is this about that stupid chainsaw?”

“It’s more than a chainsaw, honey. It’s a symbol of…”

“Quit acting like an idiot. Just go out and buy a new one.”

“I don’t know. Maybe I’m just not meant to have a chainsaw. Maybe this is a sign from…”

“Oh, my God! You need serious help. Have you been drinking already?”

“I may have had a smidgeon of vodka with my bacon and eggs this morning.”

As the years passed I thought I had recovered from the emasculating loss of my chainsaw. But, then, something happened a few days ago that sent me back into the depths of despair.

An uncommonly violent storm hit Chicago, heavy rains, rumbling claps of thunder, lightning flashing as often as a disco strobe light, and winds that gusted to 70 miles per hour. Power went out in many parts of the City. Downtown office buildings had windows blown out. And trees were knocked down by the fierce winds.

On the block where I live, large branches were torn from the trees that line the street. It seemed that every yard was littered by broken branches, including mine.

Then, the morning after the storm, I heard sounds that opened a wound that I thought had healed. It was the sound of chainsaws roaring to life. It seemed that all the manly men on block — the accountants, the insurance agents, the lawyers, the hair dresser, and the restaurant owner – had pulled out their chain saws and were preparing to clean the debris from their yards. They were doing what men do best, fiddling with power tools and cutting wood.

And what was I doing? I didn’t have a chainsaw. There was nothing I could do.

I pulled the drapes, turned off the lights and retreated to the basement to lick my wounds and try to salvage the ragged remnants of my self esteem. That’s where the lovely Mrs. Milo found me, all alone, sitting in the dark, feeling extremely sorry for myself. She took one look at me, nodded knowingly, and patted me gently on my receding hairline.

“It’s the chainsaw thing, isn’t it?”

I didn’t bother answering. Who cares what a broken and defeated man has to say?

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Letter From Milo: Lawn Mowing Man

April 22nd, 2020

“Milo, honey, are you going to mow the lawn today?”

“Hadn’t planned on it.”

“The lawn looks pretty bad. The grass is almost knee high. You haven’t mowed it in a month.”

“Fuck the lawn. I’ve got more important things to do than worry about some goddamn lawn.”

“Like what?”

“For one thing, I’ve got finish my blog piece for Monday. People are counting on me.”

“You can’t be serious! You been writing for that stupid blog site for a year and a half and you’ve got, like, 12 readers.”

“Yeah, but they’re discriminating readers, people who appreciate fine writing and lofty thinking.”

“No they’re not! They’re just a bunch of idiots who like those dumb dick jokes you always put in your blogs. Be a sweetheart and mow the lawn today, okay.”

I hate mowing the lawn. I hate yard work of any kind. As a matter of fact, I hate all forms of work. Whoever the cocksucker was that coined the term “Protestant work ethic” should be working in the PR department of BP. The slick bastard could probably convince the world that dumping millions of barrels of oil in the Gulf of Mexico was a fantastic public relations stunt. You simply cannot buy that kind of publicity.

I briefly played with the idea of NOT mowing the lawn, but decided against it. The lovely Mrs. Milo had THAT look in her eye, which meant she was not to be trifled with on this day. She grew up in the Dakotas and has a rustic’s easy familiarity with weapons and violence that I wish I would have known about before I married her.

Anyway, I spent about 45 minutes mowing the front and back lawns then went back into the house to work on my blog piece. I just started getting into a good rhythm of character assassination, slander, vile language and outright lies, when I was interrupted by a phone call from Benny Jay, another of the scabby, talentless halfwits who toil at The Third City.

“Hey, Milo, I need a title for this blog I’m writing.”

“What’s it about?”

“The Blackhawks.”

“I thought you hated the Blackhawks?”

“I do. I’m writing about how much I hate them.”

“I’ve got an idea. Call it ‘Fuck the Blackhawks.’”

There was a slight pause at Benny’s end of the line, as I knew there would be. You see, folks, the great Benny Jay is still a bit uncomfortable with profanity. Don’t get me wrong, Benny loves a good dick joke and laughs his ass off at some of the creative ways I try to use foul language in my blogs. It’s just that he’s hesitant to use curse words himself, both in conversation and in his writing. On the rare occasions when he does resort to profanity in his blogs, he usually quotes someone else spewing the filth.

In my opinion, Benny’s lack of cursing skills is due entirely to the fact that he was raised in Evanston, where, I believe, there is still a statute on the books prohibiting cursing within 50 feet of a church, school or North Shore matron.

“Heh, heh, that’s a great title, Milo, but I don’t know if it’s, ah, right for this piece.”

“Benny, it’s perfect. It’s got attitude, it’s got punch, and it leaves no doubt about your feelings for the Blackhawks.”

“Yeah, I see your point but…”

“Don’t wimp out on me, man. This could be your moment of greatness. This could be the time when you leave your footprint on the blogging world.”

“Jeez, I don’t know…”

“C’mon, Benny, be a man, act like you’ve got a pair.”

“Okay, I’ll do it. You’re absolutely right, Milo. This is no time for half measures. You can count on me.”

“I have all the faith in the world in you, Benny.”

Of course, Benny chickened out, just like I knew he would. He posted the blog piece the next day and it was called “Gulp – Congratulations, Blackhawks.” I was disappointed but not surprised. If anything, Benny is always true to his character. Still, I had to call him on it.

“Great piece you posted today on the Blackhawks.”

“You liked it, huh?”

“Oh yeah, great writing, nice concept. It was fine, everything except the title.”

“Heh, heh, I was going use your headline, had it in the draft and was going to hit the publish button when my wife came by and saw it. She didn’t like the title.”

“Your wife didn’t like it. What’s the fuck’s wrong with you. Our wives are not supposed to like anything we write. If my wife likes anything I write I immediately erase it and start all over.”

“Well, there were other considerations…”

“Like the fact that you’re a disgrace to the blogging community. You’re lucky the Barn Boss doesn’t take back your company car and toss you out on your ear.”

“It’s not that bad, is it?”

“Benny, let’s you and I get together this afternoon, have a few drinks, smoke a joint and discuss your wimpiness. You’re starting to give The Third City a bad name.”

”That sounds great, Milo. I’d love to, but my wife wants me to mow the lawn today.”

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Letter From Milo: Ratso

March 19th, 2020

In the steel mills of Gary, Indiana, the old-timers liked to tell stories about factory rats that were bigger, meaner and more resourceful than North Woods wolverines.

These factory rats were said to be super rats, superior in size, strength, cunning and savagery to their milder-natured street rat cousins. Some steelworkers believed that they were actually mutant rats, whose DNA had been rearranged by the toxic by-products of the steel industry – grease, oil, abrasive chemicals, acids and noxious fumes. Others believed it was simply the tough industrial environment that bred a hardier strain of rat.

In other words, it was the old “heredity versus environment” argument, which I thought had been settled, once and for all, by Moe Howard, back in the 1930s, in a Columbia film short called “Hoi Polloi.”

I worked in Gary’s steel mills for several summers while attending college. I worked in U.S. Steel’s Sheet & Tin Mill for a total of eight or nine months and probably heard a factory rat story every day that I worked in that steel mill.

“Old man Popovich nearly got attacked by a pack of rats. Good thing he had his welding torch handy. Used it to scare the bastards off.”

“They found some bones down by 6-Stand yesterday.”

“Human bones?”

“Hard to say. They could be human remains or leftover baby back ribs. Either way, they were picked clean.”


Although the term “Urban Legend” had not been coined yet, it didn’t take me long to figure out that the rat stories were bullshit. There were no factory super rats.

In all the months I worked for U.S. Steel, I never saw a fucking rat.

About 25 years later I bought a home in Chicago’s Lincoln Square neighborhood. It was a nice old house, solid brick construction on a wide lot. The only problem was that the garage was in terrible shape. The walls were leaning and the roof was sagging. It looked like it might collapse at any moment.

The lovely Mrs. Milo was concerned. “We’ve got to have the garage taken down. It’s dangerous.”

“It’ll probably cost a thousand dollars to have it torn down. I don’t want to spend the money.”

“There are a lot of kids in this neighborhood. What if one of them gets hurt?

“Serve the little bastard right. Teach him a good lesson about playing around in other peoples’ garages.”

“Quit being an idiot. Just call the city and explain the situation. They’ll probably take it down and it won’t cost a cent.”

The next day I called the City and got someone from the Department of Streets and Sanitation on the line. I explained the situation, told him the garage was a hazard and asked if the City would tear it down.

“No way, man.”

“The garage is dangerous. Somebody could get hurt. There are a lot of kids in the area.”

“That’s no skin off my ass.”

“I think you should be more concerned about the welfare of the citizens of this fine town.”

“I don’t believe that’s part of my job description.”

“Thanks for nothing, you worthless fuck.”

“Up yours, asshole.”

Later that day I was chatting with one of my new neighbors, complaining about the callousness of City employees and their use of vile language. It just so happened that the person I was talking with worked for the City. He explained that I had gone about this garage business the wrong way.

“Milo, you dumbass, what makes you think the City cares about anyone’s safety?

“I just assumed…”

“Well, you were wrong. What the City cares about is rats.”


“Yeah, tell them your garage is infested with rats and they’ll tear it down before you get off the phone.”

The next morning I called Streets and Sanitation again. Thankfully, I didn’t end up talking to the same asshole I spoke to before. This guy was a real gentleman.

“Whaddya want?”

“I got a problem with my garage. The damn thing is infested with rats.”

“Shit, that’s too fucking bad.”

“Yeah, they’re huge rats, man, like steel mill rats.”

“I’ve heard stories about steel mill rats. They’re supposed to be real nasty fuckers.”

“Plus, these rats look sick. I hope they’re not carrying the Bubonic Plague or something.”

“What the hell is that?”

“It’s a disease that wiped out most of Europe about 600 years ago.”

“Jesus fucking Christ! That garage needs to be torn down.”

“That’s what I was thinking, too.”

Two days later a City crew came out to my house, knocked down the garage and hauled away the debris. They even cleaned up afterwards.

I recall one of the workmen asking me, “Where’s all the rats?”

“They must have heard you were coming.”

He nodded in understanding, like it made all the sense in the world.

In our continuing efforts to improve service to the faithful readers of The Third City, we have recently upgraded our telephone system. Here are the new menu options:

For updates on outstanding warrants and lawsuits, press 1.
For information on current cease-and-desist orders and restraining orders, press 2.
To check the status of pending paternity suits, press 3.
For accounts receivable, press 4 (there is no accounts payable).
For donations to Milo’s favorite charity, press 5, (have your credit cards handy).
For directions to whorehouses, taverns, pool rooms, racetracks or Nickel Bag Bernie’s house, press 6.

All other inquiries should be directed to our attorneys.

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Letter From Milo: Ladies Man

March 8th, 2020

I hate to brag, but I’m a real pussy magnet. Even though I’m past middle age, balding, cranky and prone to farting at inappropriate times, I still have equipment that Man ‘o War would envy. Other than that, I’m just a regular guy.

Now, a lot of you may think that being a pussy magnet is all fun and games — lolling around on an oversize bed, wearing silk pajamas, sipping fine brandy, surrounded by adoring women eager to satisfy your every whim. Although in many cases – including mine – that is absolutely true, sometimes being a pussy magnet is just plain hard work.

Take a former acquaintance of mine named Charles. I used to run into him on the North Side Gigolo Circuit. I didn’t know him well. In fact, the only thing I knew about him was that he was the hardest working pussy magnet I ever met. He was the James Brown of pussy magnets. When Charles wanted to get laid he would walk into a bar and hit on every woman in the place. He had no shame, no technique and no taste. If there were a hundred women in the joint he would approach them all and ask each one if they wanted to go home with him. It didn’t matter how often he was turned down, laughed at, ignored or had drinks thrown in his face. His skin was as thick as a water buffalo’s hide. He was as single minded as a junkie, moving from woman to woman until, invariably, he found one who said “Yes.”

Admittedly, it wasn’t the approach that legendary pussy magnets like Errol Flynn, Warren Beatty or the immortal Porfirio Rubirosa would have used, but it worked for Charles. I haven’t seen Charles in more than 20 years. Word on the street is that he found Jesus and now chases salvation with the same fervor he once chased pussy.

I never had a problem hooking up, as the young ‘uns say. I would stroll into a fine watering hole and in 15 minutes I would walk out with two or three of the best looking women in the place. We would then retire to my bachelor pad where we would frolic on an epic scale, engaging in debauchery that would have boggled the mind of the Marquis De Sade.

People often confuse pussy magnets and gigolos. The simplest way to explain it is that pussy magnets fuck for fun, gigolos fuck for money.

I once considered becoming a gigolo. With my devastatingly good looks and awesome God-given physical attributes I would have been a natural. Women would have lined up to have mind-blowing sex with me. As a young man growing up in Gary, Indiana, I knew that I would eventually be an extremely handsome man. I also knew that my looks would be my ticket to fame and fortune. After considering my career options at the time – grave digger, washroom attendant, school janitor, ice cream truck driver or gigolo – I decided the latter was the way to go.

I had always imagined gigolos to be glamorous, suave, polished men who escorted wealthy, older, but still attractive women to theaters, fine restaurants and glittering social events. And after the play, restaurant or party these graceful, refined men would take their escorts to a luxurious penthouse or fine hotel and give them a thorough, professional-grade fucking, leaving them limp and exhausted, with barely enough energy left to write out a handsome check. Sounded real good to me.

As soon as I had settled on my life’s work, I decided I needed to get in a little practice. Unfortunately, there was a severe shortage of wealthy, older, but still attractive women in Gary at that time. In fact, I doubt there was a woman in the entire county who fit that description. I had no choice but to put my gigolo aspirations on indefinite hold.

Like most kids who never realize their childhood dreams of becoming cops, firemen, or cowboys, I never became a gigolo. Life intervened. Something always got in the way. There was the military and college. Later, there were drugs, booze and rock ‘n roll. I was always a lazy bastard (see my earlier post about the Bum Gene), and, from what I understand, being a gigolo can be time-consuming.

Still, even though I never became a gigolo, I became a first class pussy magnet. I cut a swath through the North Side that made General Sherman’s march through Georgia seem like a stroll through the Botanic Garden. Wilt Chamberlain had nothing on me. Even the great Bruce Diksas, a legendary pussy magnet in his own right, was envious of my skill with the ladies. I became so well known for my amorous exploits that aspiring young pussy magnets would come to me for advice.

“Milo, why do women fake orgasms?”

“Because they think men care.”

Once a pussy magnet always a pussy magnet. Even though I’ve been married for more than 25 years and not quite the #2 pencil I was in my heyday, women still find me irresistable. They know that when they have the great fortune to find themselves in bed with me that they are in the hands of a master.

Like I mentioned earlier, I’m not the active pussy magnet I used to be, but I still like to keep my hand in. Every one in a while I’ll sneak out, visit a night spot, pick up a couple of the finest women in the place and proceed to satisfy their wildest…

HOLD IT! I’m Mrs. Milo. I saw what my husband was writing and chased him away from the computer with a can of pepper spray. The whole blog is nothing but a pack of lies. To be honest, he’s not even close to the stud he claims to be. In fact, he’s a pretty much of a dud in bed. He knows as much about sex as he does about quantum physics. The only reason I married him was because I felt sorry for him. And that nonsense about his “God-given attributes” is just pathetic. At best, he’s below average in that department, even on the rare occasions when he’s sober.

I’ve already made an appointment with a marriage counselor and I’m checking into some sort of therapy. Rehab is not out of the question, either. Plus, I’m considering talking to a lawyer, just to see what my options are. Believe me, if I had known what I was getting into when I married him I would have stuck my head in an oven a long time ago. God, what a loser he turned out to be.

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Letter From Milo: Great Thoughts

March 1st, 2020

Recently the editors at The Third City hired a research company to figure out the demographics of our readers. Big Mike, the Barn Boss of this scabby crew of talentless hacks, said it was something we had to do for fiduciary reasons.

“The more we know about our readers, the better off we’ll be,” he said. “Once we know who they are, where they live and their income levels, we can increase our advertising and subscription rates and squeeze even more money out of the dumb bastards. All of the big boys do it — Guns & Ammo, Hustler, The Daily Racing Form, Minnesota Swingers Magazine. We’ve got to do it, too.”

Well, I have to admit that I was astonished by the results of the survey. A surprising number of our faithful readers have been short-listed for the Nobel and Pulitzer prizes. More than 70% have advanced degrees from Ivy League schools. 81% of our readers are independently wealthy or employed at the highest levels of government. We attract more MENSA readers than any other blog, by a margin of more than three to one. And more than 90% of our female readers have big tits.

With such a literate, civilized and genteel readership, I feel an obligation to our fans to let them have their say. That’s why I occasionally turn this column over to our loyal supporters. Here, then, are a few letters from the distinguished followers of The Third City.


Motherfucker! Where’s my money!


Nickel Bag Bernie! Is that you? You rotten bastard, you’ve got a lot of nerve asking me to pay for that bag of lawn clippings you sold me. You’re a disgrace to the pot dealing profession. I could have had FTD deliver something that would have gotten me higher than that shit you foisted on me. As soon as your mom, Dime Bag Betty, gets out of jail I’m taking my business to her.


Milo, I’m in a terrible situation at work and don’t know where else to turn for advice. I’ve got a new supervisor and he’s making my life a living hell. He’s the worst sort of bully. He yells at me constantly and calls me all sorts of names. He blames me for everything that goes wrong in the office. He threatens to fire me three or four times a day. Things are so bad that sometimes I go into the executive bathroom and cry like a baby. I can’t eat, I can’t sleep and I dread coming to work. Milo, I can’t afford to lose this job. It’s too important to me. I’ve got three little children and a very sickly wife. What can I do? Please help me.


Man, I hate assholes like that. He sounds like a rough piece of work. But, here’s a surefire way to end his reign of terror. It’s always worked for me when I’ve had the misfortune of finding myself in an untenable situation. Get yourself a gun and shoot the cocksucker. Make sure you shoot him a couple of times. You don’t want the bastard to recover. He sounds like a vindictive brute. If he survives he may try to sue you.


Hey, Milo, what makes you such an expert on sex? It seems like all you write about is booze, drugs, gambling and sex. Personally, I find your blogs extremely offensive. I caught my wife sneaking a peek at your blogs the other night and immediately made an appointment for counseling with my minister at the Lutheran church.


I am a humble man, modest to a fault. I would be the last person to blow my own horn. I prefer to let others blow it for me. That said, there are few men better equipped or as well endowed with the knowledge and experience that is needed to be able to offer advice to the fornicationally challenged. The great ones – Casanova, Don Juan, Sir Walter Raleigh, Porfirio Rubirosa, Catherine the Great’s horse, Errol Flynn, and the immortal Wayne Gray — made it a point of honor to pass on their knowledge of the studly arts to those who followed in their footsteps. Although I am too humble to put myself in their exalted company, I would be doing a grave disservice to aspiring Pussy Magnets everywhere if I failed to do the same. The letter below, from a young man floundering in the sexual widerness, is a perfect example of why it’s important to pass on traditional manly lore.


Hey, Milo, it’s me, Benny Jay. This question is not from me, honest. It’s for a friend of mine. Is it true that size doesn’t matter when it comes to sex? Like I said before, this question is not from me. My friend would appreciate an answer ASAP.


Benny, let me put your, ah, friend’s mind at ease. Size has absolutely nothing to do with sexual pleasure. The truth is, you can have just as much fun with a fat woman as a skinny woman.


Milo, I’ve decided to start my own blog site and get rich and famous like you guys at The Third City. It’s going to be a Christian blog site, dedicated to Christian ideals. I’ll post notices of good, clean, family activities, like hayrides, all-you-can-eat fish fries, spelling bees, corn shucking contests and church outings to Six Flags. What do you think? Any advice would be appreciated. Bless you.


Eh, great idea, kid. Add a little good Christian porn, strictly missionary position stuff, of course, and you’ve got a real winner on your hands.


What ever happened to your friend Teddy, the bank robber, who spent 22 years in a Mississippi prison?


Teddy turned up about a week ago. It seems that he had spent the last four months in the McHenry County Jail on a forgery charge. Teddy assured me it was a bum rap, a simple misunderstanding, something about a questionable signature on a check. That’s what happens when you rob banks. You get on all the authorities’ shit lists. Make the smallest mistake and they come after you. It doesn’t seem fair. A man robs a few banks and he’s considered a criminal. Yet, when the banks rob us, the bank executives end up getting a free trip to Washington, D.C. so they can spend a pleasant afternoon amiably chatting with Senators in an air-conditioned room. What they should do is take the motherfuckers outside, put them up against a wall and…

Note from the Editors:

Due to the flood of angry calls, letters and emails to The Third City, we are suspending Milo without pay indefinitely. He will not be allowed to write for us again unless he agrees, in the presence of witnesses, not do any more letters or advice columns. We want to assure our loyal readers that The Third City does not officially endorse or condone drug use or drug trafficking, indiscriminate sexual activity, pornography, bank robbery or armed violence of any kind. On the advice of our attorneys, we can say no more.

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Letter From Milo: Big Feller

February 24th, 2020

Every man wishes he had a bigger dick. No man is satisfied with the load he carries. Every man would like his log to be longer, thicker and more imposing. Even the late, great Johnny Wadd, the gold standard of big dicks, probably wished he had an extra inch or two, just to be on the safe side.

Now, a few of you might say, “Milo, how can you say that ALL men want bigger dicks? That’s a pretty broad generalization.”

Okay, I’ll give you that much. Maybe not every man is obsessed with the size of his dick. Perhaps there’s a religious hermit living in a cave in the Alps who never gives his dick a second thought. There could be a junkie somewhere who’s so degraded by heroin that the only time he considers his dick is when he wonders how much he can get for it on the black market. There may even be a Talmudic scholar somewhere who considers his dick a nuisance, because every time he gets up to piss it takes precious time away from his studies.

Here’s a simple test that will prove my point. Go up to a man, any man, a friend, relative or stranger in a bar, and ask him this question.

“Dude, how would you like to have a smaller dick?”

If you don’t get beaten up, stabbed or shot, I guarantee you won’t find a single person who’ll say, “Now that you mention it, I think I would like to have a smaller dick.”

Recently, I had a few drinks and smoked a joint with my good friend, Professor Wang, who’s head of the Anthropology Department (Online Division) at the Triple A College of Nutrition and Cosmetology in Gary, Indiana. He explained to me that men have been concerned about dick size ever since the first half-monkey crawled out of the mire and discovered that standing on two legs gave him a better view of his dick.

According to Professor Wang, the earliest cave art ever found, in a cavern near the Quad Cities, was a crude painting of a group of naked Neandertals comparing their dick sizes. Coincidentally, right next to that drawing is another one of a group of Neandertal women laughing their asses off.

john c. holmesThe Gold Standard….

For as long as man has been aware of his, ah, shortcomings, he has taken steps to remedy the situation. Mankind’s very first invention, pre-dating the discovery of fire by more than a million years, was a primitive dick extension contraption. It was made of mammoth hide, pine cones, pieces of flint and a rabbit’s foot.

There is no record of its effectiveness.

Throughout history great minds have spent countless years and untold millions of dollars trying to come up with a mechanical solution to man’s most vexing problem. Aristotle, Pythagoras, Leonardo Da Vinci and Thomas Edison all tried to come up with a male enhancement device — and all failed miserably. Rumor has it that Bill Gates squandered half of his Microsoft fortune in a fruitless search for the Holy Grail of manhood.

In all of recorded history there is only one penis enlargement device that has proven successful. In fact, it works spectacularly well. It was invented a Swede named Sven Loewhangen and he called it, “The Fabulous Swedish Dick Extender.”

Due to Mr. Leowhangen’s untimely passing, something about ingesting some spoiled lutefisk, less than a dozen of his marvelous inventions were ever manufactured. And they are now nearly impossible to find.

I, however, was determined to find one. Not that I need one, you understand. As far as male attributes go, I’ve been truly blessed. No, my interest in “The Fabulous Swedish Dick Extender” was purely academic. One day I may even submit a paper on the subject to Reader’s Digest.

After years of the most arduous research, I finally tracked down the legendary contraptions. Most of them were in the hands of the Saudi royal family, who refused to part with them under any circumstances. Another belonged to a Chinese soy sauce tycoon who refused to admit he owned it. Yet another one belonged to the estate of the late sportsman, Porfirio Rubirosa, but his heirs claim to have misplaced it.

Just when I had given up hope of ever finding one of the elusive machines, I got extremely lucky. I made the acquaintance of a woman named Ruth Madoff, whose husband, Bernie, seemed to be experiencing some financial problems. She agreed to sell me her husband’s “The Fabulous Swedish Dick Extender,” but the price was steep.

To raise the money I had to take out second and third mortgages on my home, sell my sure-fire horse betting system to Bruce Diksas for a pretty penny, and transfer my interest in The Third City blog site to the Tribune company.

Well, I sent the check off to Mrs. Madoff and now I’m waiting for the FedEx man to arrive. I’ll let you know if my search for “The Fabulous Swedish Dick Extender” was worth all of the aggravation and expense. I sure hope it was.

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