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Authors: Tony D

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A Thousand Tiny Failures : Memoirs of a Pickup Artist

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A Thousand Tiny Failures

By Tony D

Copyright © 2012 Tony D

Kindle Edition 2013

Table of Contents

Chapter 1 - Child Soldiers

Chapter 2 -Transmogrification

Chapter 3 - Esther

Chapter 4 - Spirituous

Chapter 5 - Luv

Chapter 6 - Montreal 2008

Chapter 7- Rooftop Combat

Chapter 8 -

Chapter 9 - Olivia

Chapter 10 - Factotum

Chapter 11 - Confessions

Chapter 12 -
Sex, Drugs, Rock and Roll

Chapter 13 - The Lair

Chapter 14 - Montana

Chapter 15 - Lara

Chapter 16 - Epiphanies

Chapter 17 - Sarah

Chapter 18 - Orgasms

Chapter 19 - “Good girl?”

Chapter 20 - Abode

Chapter 21 -

Chapter 22 - Les
, Part 1:

Chapter 23 – Les
, Part 2: Liz vs. Dianna

Chapter 24 - Blowjobs and Validation

Chapter 25 - Number Three

Chapter 26 - Two down, one to go

Chapter 27 - Vancouver

Chapter 28 - Rickard Yang

Chapter 29 - The

Chapter 30 - Con men of love

Chapter 31- Sand Pussy

Chapter 32 - She’s Married

Chapter 33 - Madonna Whore Complex

Chapter 34 - Frosted Flakes

Chapter 35 - New Year, New Woman

Chapter 36 - Victoria

Chapter 37 - Beauty is Only Skin Deep

Chapter 38 - Montreal, La

Epilogue :
The Four Thousand Islands, Laos, 2013

Chapter 1

Child Soldiers. (Mommy, Where’s Daddy?)


I tried to shove the kid off my chest, but I’d already given up. His pink fists
my pimpled face but I was too timid… too mentally weak to even try and defend myself. I’d seen fights in movies. I knew how to swing a punch; you just wind up and toss—but nobody ever told me how to think like a fighter. Not yet anyway. Besides, every man should have his ass kicked at least once just for the experience.

! You have tits, you pussy!” His spittle landed on my face.

And I did. I was a skinny boy with perky little man boobs; my genetic curse. I blame milk and power lines and bad luck. I sort of hated myself.

“Hit him back Sebastian!” the other kids screamed. The little bastards wanted blood.

“Yeah hit me… you bitch!” he complained.

But I wouldn’t. I just lay there, eleven years old and as compliant as Rodney King on opium. Fight back? That would hurt. I stared up at my former friend’s face and saw disgust, pity, and disappointment. He would be my friend again tomorrow.

This wasn’t a protest against violence—I just didn’t know what to do. Nobody had ever hit me before. He slapped me once on the cheek and got off. The other kids shook their heads and rode off on their bikes; the warm summer air blowing across their cherubic faces, past their safe, middle class neighborhoods, spitting and laughing and throwing rocks at dogs and cats and each other.

Life is beautiful. Children are great.

I dusted off and went back inside to play with my little sisters.

“What were you doing Sebastian?”

“We were play-fighting.”

“Did you win?”

“… Yes.”

I went into my mom’s room and called my own phone number, waited for my sisters to answer and pretended I was Santa Claus. “Make sure you scratch your brothers back whenever he asks! Ho

“Ok Santa.”

My childhood was mostly nice and safe. I was raised by a single mom; a beautiful, resourceful, sweet and creative woman who, although loved me deeply, was unable to impart one of a boy’s most important lessons… how to be a man.

I don’t remember when I discovered my boy-tits, but one day there they were, the bastards. This horrid conundrum is usually called,
, and affects tens of thousands of broken men worldwide. I was baffled. I mean, whose god did I enrage to be cursed? Fuck my life.

My generation is the divorce generation: Alimony for moms and freedom for dads. When my mother met my father she was deciding on whether to go for food, or play pool. She chose pool and my dad picked her up at the pool hall. If she’d gone left instead of right, I never would have been born, or I’d be a squirrel, or a jade Buddha, or Michael Jackson’s left testicle.

My father was a semi-deadbeat. Not that he didn’t pay child support and spoil me at Christmas. He had us for summer vacations, but generally wasn’t around. I don’t blame him. I like cities too, and I didn’t care at the time. Kids are too interested in swimming and lighting fires and make-believing to wonder where their dad is. Anyway, I had my mom’s boyfriends to learn from, but they were always careful with their wisdom lest they give the wrong advice and piss off Mom.

There would be about one boyfriend every two or four years. That was the cycle. My mom would keep them around until they screwed up, acted possessive, or drank too much. I liked all of them. They taught me cool things like how to shoot guns, ride motorcycles, play guitar, chop wood, slay furry animals… that sort of stuff. She always liked the bad boys. They were long haul truck drivers, Harley Davidson enthusiasts, rodeo cowboys, street fighting champs, big game hunters, and Vietnam war vets. So it’s surprising I ended up so… nice. Remember this when talking to a kid: they watch, they learn, and then they forget. So your words and actions become their minds… their twisted little identities.

When she dumped them, she worried whether we’d be traumatized. I never really cared though. I’d moved around so much at a young age that I’d learned independence. I was somewhat of an introvert already; I didn’t need anyone—except when it came to girls. They were fascinating and terrifying, and I had no clue—which is ironic because I teach men how to pick up girls for a living.

I watched the local kids go swimming, date, play shirts vs. skins soccer games and enjoy the summertime sun on their bare skin. I never took my shirt off—that would be the greatest of horrors. I was a shy, depressed, freak. This made elementary school somewhat horrible, which was nothing compared to high school. Post primary education ensures that the illusion of social equality is rightly crushed. Society has a place for you, whether you like it or not. Luckily, if you’re reading this book you’re one of the smart ones…you read. You can improve things. Well, maybe not if you’re from

I identified with the anger and disillusionment of punk music. I broke from what I considered, “the herd of conformist jocks, sellouts, and hippies.” After hearing Smells like Teen Spirit, by Nirvana, I decided I wanted to be a rock star. One of Mom’s boyfriends bought me an electric guitar for seventy-five dollars, and I practiced obsessively because guys in bands are cool; guys in bands get ass.

I also loved anything escapist and lost myself in books, movies, and video games. This digestion shaped my distaste for group-think. Movies like A Clockwork Orange, Natural Born Killers, and The Matrix. Bands like Minor Threat, The Misfits, Nirvana, The Dead
, and Operation Ivy. Books like 1984, Catcher in The Rye, The
, On the Road, Fear and Loathing in Las Vegas, and Lord of the Rings. Art that cheered for the underdog and thrived on the fringes. Nineties kids were pissed off. Most kids are. But it wasn’t just teen age angst…I had tits. I had teen-age man-
angst, and I wanted to hide inside my imagination where everything was awesome.

Girls tried to flirt with me but I always screwed it up. They thought I was cute; this shy, long-haired teenager with dimples and middle finger fuck
, hand painted onto his jeans. I wondered if they noticed under my incredibly baggy t-shirts that I had boobs. I thought about this obsessively—like a dog that chews one spot until it’s bald. I told myself I didn’t deserve attention; I was a loser and it’s cool to be a loser. I mean, at the time the biggest song on the radio was Loser, by Beck. Negativity was encouraged in the nineties.

I talked to a few girls in my classes but I would get nervous and say dumb shit, like how the world is fucked and everyone’s a stupid sheep, or that we’re all living an Orwellian prophecy come true. Rest assured this strategy failed. I couldn’t hold eye-contact, I slouched, spoke in submissive whispers, and dressed like a grunge hippie. I was waiting for a girl to see me for who I was…on the inside. They did! It’s true what they say… that nobody will love you if you don’t love yourself. Not like your grandma loves you, I mean more like I want your penis in my vagina love you.

The first girlfriend was in eighth grade. She was a busty, dirty blond: a volleyball star. After stalking her from the bleachers for a year, I schemed to make friends with her friends, break into her social circle and get at her boobies. And I did. It was very Machiavellian. I ditched my elementary school crew and started wearing dress shirts and loafers like the rich kids. The rich kids accepted me and introduced me to my volleyball star. Through extreme palpitations I asked, “Do you want to go out with me?”

“Hmm. Ok!” She shrugged.

What luck! Hers were the first breasts I ever touched. Oh joy of joys! I would go to her house and make out with her for hours, until my groin ached so bad I’d want to be sick, then I’d ride my bike home and furiously masturbate as quietly as possible, praying my sisters wouldn’t hear. I probably could have banged her, but I was fourteen and had no clue how to make that miracle happen. Plus, I’d have to take my shirt off.

She dumped me after two months. “Can we be friends?” she asked.

I was jealous, needy, and insecure. I cried a few times, or a few dozen maybe. I called her and begged her to take me back. I left roses on her doorstep at
. I wrote poems about my devotion and taped them to her locker. My reward for this gallantry was having her humiliate me in the school hallway by yelling, “Sebastian, I DON’T LIKE YOU ANYMORE!” To prove it she made out with her new boyfriend—the bloody captain of the rugby team. How cliché is that? He had a, “sorry for you bro,” look on his face. He knew I didn’t get it yet. It’s the same way I’ve looked at other guys when I stole their girls. It feels good to be him, the winner.

I looked her up on Facebook once. She’d gained twenty pounds. Still pretty in her late twenties, but close to hitting the wall. I sent her a message:

“You were my first girlfriend. I still remember. I was pretty pathetic.”

She replied:

“Oh really!? I didn’t think so. I was such a slut back then.”

I sent:

“Wow. That’s funny. I’m such a slut now.”

They say men age like wine, and women age like cheese. Of course, there are specialty cheese shops, but they’re rare and expensive. And most men are more like a box-wine, not a fine
. If it’s war you seek, we’re at the advantage there. Don’t pity them; when they’re sixteen to twenty-five, (if they’re beautiful), they’re spoiled as they want.

Ah misogyny. If you think that’s me, you should be reading Harry Potter, because this book is about reality, not a magic wonderland. But if you still wish to roam Hogwarts, believe in magic. Be positive.
is the universal key. I feel that I’ve been good to people and have little bad karma. This is the story of how I freed myself from the tyranny of the mind: by banging lots of girls. I hope it helps you. But it may do the opposite. Not my fault. Just saying.

One lucky summer I managed to lose my virginity, fairly young at fifteen years old, to a well-endowed blond two years my senior. She pretty much raped me one fine afternoon in my best friend’s grandma’s spare bedroom. She had these enormous, magnificent, seventeen year old breasts that you could just motorboat all night. Angie was my good friend’s very recent ex, and she was already eager for a new dick. I don’t know why, maybe she had daddy issues. I didn’t question it. She approached me while I was sitting at a Dairy Queen, placed her hand under the table, and massaged my boy-shaft. “Take me somewhere we can fuck,” she commanded. Grandma was at a three-day crockery show, we had the keys, so off we went.

When I plunged into her I came in about thirty seconds. “You can go again!” she ordered, and worked her magic. I manned up and gave it to her silently, missionary position, for about forty-five minutes. “Make some noise!” she demanded. So I made a few grunts, and pumped and jabbed and poked and licked until I was drenched and drained. I couldn’t come twice. I didn’t have it in me. She rolled over, turned her back, and refused my adoring, sweaty cuddles. Goodbye virginity.

In the following days, she cut me off. Word around town was that her ex-boyfriend, the town fist-fighting champ, was hunting me. When he finally found me all the menace left him. “Sebastian, I can’t blame you man. You’re too nice, and her tits are too big.” He gave me a hug and we smoked a joint. His entourage was disappointed. She used me for sex. Wasn’t it supposed to be the other way around?

I had one girlfriend for a month in grade ten and managed to have sex four times, which was better than most, but pretty bad. She wasn’t a great catch, so I let her go. I’ve always had standards higher than my ability, and I’ve rejected more than I’ve captured.

After high school, I moved to
to live with and work in my dad’s furnace repair company. He was a failed ladies man, an arrogant charmer, unconscious of the concept of ego and internal chatter—and a closet cocaine addict/manic-depressive. If I learned anything from him, it was masculinity and work ethic. I also learned we weren’t much alike, except for our fondness of beautiful women. We’d spot them from the van like pro birdwatchers.

“Dad, look at that one.”

“Jesus Christ—look at that ass!”

“Hell yeah.”

“Go talk to her.”

“No way.”

And off we’d drive to work and argue for the next eight hours.

He was a funny guy—when he wasn’t being a jerk. He could tease my stepmother to tears of laughter and the next day bring her to tears of rage. He had a mind for seduction too. He’d tease me for not having a girl. I think, as did many, he figured I was a bit queer, ya know, a fag. Not that he was homophobic; he wasn’t.

He was such a proud father when I finally convinced a girl to come over to my house. When I couldn’t make it back from her place one night, so her dad wouldn’t find out, she made me sleep in her walk-in closet. If that happened today, I’d laugh at her, pull out my dick and poke her in the eye with it. I didn’t tell him that she already friend-zoned me.

Chicks dig musicians, and I’m a narcissist, so I started a punk-band. It doesn’t matter if you suck as long as you’re on stage. Even if you look like post-lava Darth Vader, if you’re slightly famous, girls will hook up with you. Even Danny
can pull ass. Take a fat, bald midget, put him on
, and he’ll have beautiful women scratching out each other’s eyes to get at his dick.

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