A Thousand Tiny Failures : Memoirs of a Pickup Artist (17 page)

Women need to trust you, so I built trust. It can’t be all Santa and Unicorns. It’s risky to leave the role-playing and come back to reality, because the girl might realize you’re not that interesting. She was from
Halifax
, visiting her parents for Christmas. She liked skiing and drinking. She had a fun and bubbly personality, small breasts, green eyes, a button nose and dimples. Probably the prettiest girl I’d caught up to that point. She looked like the sort of girl I would fantasize about in high school. I’d watch them from afar and wonder how I would ever get with a babe like that, and now here I was making out with one, like I did it every day. She would never know how hard I had to work for her.

“Look!” I said. “It’s snowing outside, so let’s go on an adventure. You’re not crazy are you?”

“No, no! I’m not crazy. I’m a good girl.” She sat up extra straight in her cutest good girl, not-crazy pose.

“Okay, is your friend going to stop us? Go tell her you’re leaving with me. We’re going to make snow angels.”

I believe in you Sebastian.

“
Yay
! Snow angels!” she cheered, clapping like a drunk baby. “I won’t let her stop us.”

It’s important to have a reason to leave, like making snow angels. Of course she knows we’re going to bang, but again, it’s not allowed to be her fault. It just has to happen, so she’s not a slut… even though she is. Sometimes I have a cool movie to show her, or my Siamese fighting fish, or a childish video game. You want to keep her mind occupied, far from logic and reality. It’s dangerous being a girl. They need to believe you aren’t going to eat them and use their bones for arts and crafts. There are believed to be cults of
pua
D&D nerds, rolling D10’s made of pure virgin tibia.

I held her hand while she talked to Princess Cock-block. Summer was on my side. Every few seconds she would give my hand a squeeze, and I’d reciprocate. We were on the same team: Team getting laid tonight. Then she looked at me with her big green eyes and said, “Let’s go!”

I walked her to the coat check, looked back and saw seven guys huddled in a group, watching me pull this hot little blond. I waved, they waved back.

Winning. Winning. Winning.

There was a snowstorm that night. Strong gusts were sending giant swirls that flew up our jackets and bullied us. On every corner were groups huddled for warmth, hailing taxis that zipped by, full with their lights off. This was bad. Girls don’t like being uncomfortable. They don’t get off on conquering hardships the way men do. This could spell disaster for my seduction.

“It looks like we’re walking lady,” I said.

“It’s nice out! I don’t mind a trek.”

“Good girl. I’ll carry you,” I said, and leaned down so she could get on my back. I carried her a few blocks and flopped into a snow bank. She screamed and punched my shoulders with her little fists. I picked her up and pushed her against a street lamp, put my tongue in her mouth and squeezed her firm, round ass. It was so excellent, and she tasted like the best Christmas ever. Across the street a group of young men were cheering us on. “
Woooo
! Go bro! Nice!”

“I really like your beard. It tickles my face.”

“Oh yeah, check it out woman!” I nuzzled in there and wiggled my face on her neck. She screamed. Our walk was long: at least thirty minutes, in a storm, but she didn’t complain, not once. Every few blocks I pushed her against a wall and kissed her, just to keep the fire stoked.

We were both freezing so I ducked into a busy pub. “Let’s grab another drink” I suggested.

I was a little worried that she would sober up and change her mind; that she would realize I’m only pretending to be this awesome. Her attractiveness was a bit intimidating. I was already imagining her as my future girlfriend. It wouldn’t be so bad. We could have picnics and go to wine and cheese parties, maybe meet each other’s parents. We could fight and then have make up sex. I could teach her pickup and we could have threesomes. We could do
improv
classes together, and go to
indie
-rock shows. People would look at her, and then at me, and wonder, “How did he do it?” Books, you fools, books.

We ordered a couple pints and sat down. Within thirty seconds the wolves descended. They figured I must be her brother, or gay best friend. One guy approached us crooning a
Weezer
song drunkenly into his beer glass.

“If you want to destroy, my sweater, pull my strings, and I’ll come undone!”

His eyes were squarely on Summer. I turned her head and kissed it until he pissed off. Under the table, I put my hand on her thigh, and crept up. She didn’t complain. I ventured a little higher and rubbed the outside of her pussy under her skirt. She smiled. I slipped a finger inside of her; she put her head on my shoulder and kissed my neck. It was time to get her home, before she changed her mind. I’m always a small trip away from failure.

She whispered, “I have to go to the bathroom. I’ll be right back.”

“I’ll come with you.”

“You don’t have to.”

“Yes…I do.”

I won’t let her go. I don’t care if it’s needy. I held her hand as we slipped through the crowd of young drunks, past make-outs and arm wrestling and binge drinking. The wolves were hunting, licking their teeth. Another guy tried his luck, but he was too messed up and I shouldered him out of the way. These guys were amateurs. While she was in the can I meditated on
positivity
—always positive. When she returned, I kissed her again, just to make sure.

We exited the den of drunkenness and landed back on the path of glory. We were still kissing and talking and I felt like a true champion; rightly validated. I thought of all the lonely losers sitting in their parent’s basements eating
Cheetos
and masturbating to pictures of their sisters’ best friends on Facebook. Not me. I’m a living legend. Such is the power of the dark side.

“Here it is! It only took us forty minutes. Not bad,” I said, unlocking my front door and ushering her inside.

“
Haha
. Yeah not bad,” she said, brushing snow from her hair, surprisingly chipper.

We snuck up the stairs past my roommate’s door. Once in my room, she turned around and pushed her breasts against me. I lifted off my shirt and she mirrored. I thought of my soft, chubby body, and her fit and youthful one. How did I do this again? I admired and explored her long gorgeous valleys of snowy flesh. Thank you, thank you, thank you Sebastian, you smart devil.

Nice work bro. But I’m sleepy.

Her pussy was freshly waxed with only a little landing strip remaining; a pussy-hawk. I couldn’t help myself. I got down, pulled aside her panties and kissed it. First all around the outside, in little circles venturing closer and closer to the center. It was like a pink little flower blossoming on my lips. Stars and rainbows and Unicorns hooray! She moaned and wiggled her hips and even laughed a little. As I was working away her cell phone rang. She reached down and punched in a long reply, then tucked it back into her purse. “Sorry,
mmmmmm
, that’s good,” she said, pulling at my hair.

She pulled me to the bed, fell to her knees and started her work. The amateur! Her teeth raked my dick. “
Owww
!” I cried. She tried again but she was terrible, so I flipped her over onto her belly and finger banged her from behind. She bucked her hips and squeezed my pillow while moaning with pleasure. I leaned into her for some dirty talk.

“Oh you’re so pretty. You’re little pussy is ready for me isn’t it?”

“Yes! It’s ready!” She replied enthusiastically. “Fuck me, fuck me please.”

You have to work a woman’s mind, as well as her body. I’ve got a friend in the
Montreal
lair that can bring a girl to orgasm with words alone. He’s a hypnotist. I’m not. So I use my penis.

Hey man. I’m not feeling so good tonight.

I slipped on a rubber that I had stashed under the mattress. I congratulated myself for preparing for such blissful moments. I hovered my dick just on top of her pussy, but halted shy of pushing in.

“I want you to beg for it,” I said.

“Oh please, oh please, I need it!”

“Do you really? I don’t believe you.” I shoved it in, just a little bit and pulled her hair, arching her head. “I can’t hear you Summer. Do you like me enough?”

“
Yeeessssss
! God fuck me now!!!! I like you, I like you!”

“Ok,” I said as I jammed it in, up to the hilt. She cried out and took it. I start thrusting like a mad man, but something wasn’t right. It just sort of
noodled
out. I was soft like a baby finger, or an uncooked sausage. I took it out and slapped it a few times. I put in back in. I played with her ass, her tits, her lips, but it just wouldn’t stay up. I got up and stretched, and tried again. I prayed to
Crom
even, but he wasn’t listening. After a while I gave up.

“Sorry, I don’t know. It must be the booze. Give me a minute.”

“Yeah, you drank a lot. It’s ok,” she said. “I already came anyway, when you were going down on me.”

“Really?”

“Yah.”

“Cool.”

I waited a few minutes and then tried again. I got semi-hard and gave it my best, but I couldn’t come. It just flopped around in there like a dying fish. Ashamed, I rolled off of her and put on my boxers. I finally pulled the hottest girl of my life and I couldn’t keep it up? What cruel joke is this? I laid on my back to rest and ponder the absurdity. Her phone rang.

“Yeah, tell my mom I stayed at your house ok? Yeah. Oh I’m ok. I’m just at that Nathan’s house, from the Cellar. Yeah. Oh my god, she did what? What a jerk! Yeah? Hmmm. Ok. Yeah? Ok. No he’s nice. I’m ok. Talk to you tomorrow.”

Yeah. She called me Nathan. Whatever.

Sorry dude… maybe you should work out more or, something. She must be disappointed.

I woke up early and looked over at my girl. She was stunning with the light shining through the window across her
pouty
, sleeping face. I played with her boobs for a little while until she woke up. I tried to give to her again, to make up for the poor performance the night before, and I did alright this time. I kept it up and lasted about ten minutes. Mental note, binge drinking makes sex fail. I took her for breakfast and we talked about insignificant things like school and work. I told her I wanted to see her again but she said she was going back to
Halifax
after Christmas, and she was busy every day until then.

Every day, I thought. Sounded like a blow off. Oh well. I guess that’s why they’re called one-night stands. The cycle continues.

I got to work early that day. I had a plan: I would charm some of the other managers for a promotion. I would double my production, work twice as fast, and be ten times as positive. As I was setting up my section, another manager, Mick, called me over. “Sebastian, I need to talk to you. Take a seat.”

“Ok.”

“You’re a really great guy, really smart. But you’ve been asking all the managers for promotion. You can’t just ask for a promotion. You have to earn it. On top of that, you’ve been talking back to the servers.”

“What’s wrong with asking? Shouldn’t you go for what you want, or make it known you want to succeed?”

He took a sip from his coffee.

“That’s not how it’s done. You need to be humble.”

“I don’t see how being humble will get a guy ahead in this life. You need to take action. I can’t stand being passive,” I said, growing irritated.

He checked a text message, wrote a reply and then looked at me.

“Look, Sebastian. It’s just not in the cards. If I was you, I would submit my resignation. Give two weeks.”

FUCK YOU

“Am I being fired?” I said, grinding my knuckles into the table.

“No, you’re not. But you should go. You won’t get ahead here.”

“Why not?”

“It’s not for you.”

“Ok, that’s fine,” I said, standing up. “Can I go back to work now? I have a lot of tables to clean. People are extra sloppy during the holidays.”

“Yes, that’s all. And Sebastian, you’re very
hireable
. Don’t be down. This just isn’t the place for you.”

“Sure thing, boss,” I said, fixing my apron and heading back into the mess.

I walked past the bar. “Sebastian!” One of the servers yelled. “Where you been?”

One day people will line up to shake your hand. You will teach them how to free themselves from the tyranny of a sexless, artless, soulless,
respectless
, passionless existence, and rise above the sheep. You will do great things, and when these peons come to kiss your ass, you will fart on their lips. They’ll wipe the fart grease off their lips, and sell it on Amazon.

I could understand where the managers were coming from. I talk too much, ask too many questions. That’s not the way they did it. They did the grind, waiting for life to give them permission to move forward. They’d never created something out of nothing; they’d never done anything for themselves. All they did was find a job, collect their pay check and follow the rules. That’s what they expected me to do. That’s what we’ve been doing. That’s what you get.