A Thousand Tiny Failures : Memoirs of a Pickup Artist (11 page)

Orgasms (Dream catchers)

I went out every night, seven nights a week. I didn’t just want to practice pickup, I wanted to be great at it. Fuck mediocrity. I’d follow the usual routine of slaving at the Call Center of Doom, ride my bike home, smoke a bowl of
Montreal
weed and power nap, wake up, read pickup and self-help books, watch videos, then go out. I’d been on a handful of dates with some cool chicks, but nothing was panning out. Maybe I needed to work out more, or find a social circle, or meditate. I wasn’t sure when it would get easier, but I was definitely focused. I always believed it would pan out. I had to. I had to change my life.

Most of the girls I met were between eighteen and twenty-three. They went to the clubs; they were the ones I couldn’t get in high school. I’d tasted success and I wanted more, so I kept up the regimen because it was working. I rarely stuttered or had panic attacks. I was funnier, more confident; I dressed better and had a small group of friends, mostly guys from the pickup lair, people I had approached and the social circles of various roommates. I was happier, much happier.

Olivia found herself a real boyfriend, so we stopped hanging out. It was just like that. It ended. I wasn’t sad; it was more like I lost a cool pair of pants. I guess I’m a jerk. One day I got on Facebook and searched for
Montana
, the BJ cat girl that gave me a fake number. I found her and sent a poetic and heartfelt message about how I’d love to see her again. It was a little bit sappy, and the pickup guys would call it beta, but I had nothing to lose, and it worked because two days later she agreed to meet me for drinks.

I arrived at
eleven p.m.
. The bar was dimly lit, with high tables and scattered couples sharing stories and drinking cocktails.
Montana
was already there, and when she stood up I kissed her on the cheeks, as is the custom in
Quebec
.

“You look nice,” I said.

“Thanks. I think I look like shit. I stayed out too late. How are you?”

“Awesome. I’m living the dream.” I took a sip of my rye and ginger without lowering my eyes from hers.

“The dream huh?”

“Yeah, the dream.” I slapped her thigh lightly.

She moved closer, so I put my arm around her shoulder. We were a match. We fit. It’s always best to assume you’ve already succeeded—that you’re the shit. Narcissism works.

Atta
boy, champ.

She went to school at Concordia, studied a little bit of everything for no apparent reason. Her favorite things were long trips to faraway places where she could hula-hoop on beaches and surf. Pretty girls love beaches because they can practice their two favorite hobbies: being attractive and being comfortable.

She was impressed how I picked her up, and she loved my fictional dirty talk. She called me, “Mr. Writer.” At one point, I put down my drink and kissed her, with tongue. I licked her straight teeth and she bit my lip. Her eyes got me. They were just so big and pretty.

“You weren’t impressed enough to give me a real number,” I said.

“I totally did.”

“Nope. You changed the last digit.”

“It was an accident. I promise.”

I adjusted my crotch because my boner was in an awkward position. I think she noticed.

“You owe me, bitch.”

“Hey!” She pinched my stomach fat. “What do you write about anyway?”

“Mostly about myself, people, odd situations, women.”

“Really… so are you going to write about me?”

“That depends.”

“On what?”

“We’ll see what I can learn from you, I guess.”

She finished her drink. A few guys at another table were checking her out. She ignored them.

“I’d like to read some of your stories,” she said. “I wrote a few short stories too, but they’re not very good.”

“It takes practice.”

“Yeah I know.”

“So, what else do you do?” I asked.

The server dropped off two more drinks. They were good and strong. We both took big sips.

“I’m good at lots of stuff,” she said.

“Like what?”

“I make things, earrings, jewelry, dream-weavers.”

“And sell them when you travel?”

“Yeah. I sell them sometimes.”

“Are you going to make me a dream-weaver?” I asked. “I have dreams.”

She leaned back and sized me up. “I don’t know. I don’t really know you.”

“Well, I put my dick inside you. You know me pretty well I’d say.”

She laughed, squinting her big, pretty eyes. “That’s not knowing. That’s just a blow job.”

“So get to know me better then.”

“
Ummm
, nah. I just want to fuck you,” she said.

Dude, dude, yes!

I know, I know!

This was the window, time to climb through before she changed her mind.

“Let’s get out of here,” I said, looking at the time.

“Ok, my place is a block away.”

As we walked back to her apartment, I felt in my back pocket for my condoms. I’d only brought two. I kept my hand on her behind and played with it. The booze was in my blood and my dick was still hard. I stopped to kiss her on the doorstep and pressed it against her so she’d know I was ready. She reached down and gave it a squeeze. Good girl. No bullshit. We got inside and she went to the bathroom. I took of my shoes and jacket and explored her apartment. It was clean. Lots of books on her shelf, dream-weavers in her windows. It smelled like patchouli, she was a bit of a hippie.
Montana
came out and walked straight to me, kissed me on the mouth and played with my balls. Nineteen year old glory! She started walking backwards, slowly, towards her room and fell onto the bed, pulling me down with her. I sucked on her neck, I squeezed her thighs. She made little grateful noises and scratched lightly at my shirt, so I stood up and took it off.

“Tell me another story Mr. Writer.”

“About?”

“I don’t know, you’re the writer.”

She undressed until we were both in our underwear.

“There once was a man who came out of the east,” I said, and licked from her belly button to her neck. She sighed. “He
travelled
the world seeking out adventure. His conquests of women became the stuff of legend.” I got on top of her and ground my crotch into hers. She let out an encouraging moan, her eyes widened. “One day he met an orphaned farmer girl. He promised her five shillings in exchange for a place to sleep, but she knew her father would refuse such a handsome man sleeping under his roof with his daughter.” I pulled out one of her breasts, squeezed it, and stuffed it in my mouth, licking all the way around her nipple. I reached down and felt her pussy; it was soaked through her panties. I leaned back and continued.

“So that night she left her window ajar so the man could slip in when her father went to sleep.”

“Did he come in?” she asked, between heavy breaths.

“Of course, at
one a.m.
, she heard him at the window and then felt him slip into her bed.”

I pushed aside her panties and slipped two fingers inside of her. She moaned and bucked her hips. I flipped her over onto her stomach and kicked off my boxers. I kept one hand at work on her inner thigh and used the other to slip on my rubber. Practice makes perfect and I’d had lots of practice lately.

“She didn’t think she would sleep with him,” I continued. “But his presence in her bed was too much for her, it made her pussy wet knowing that her father lay asleep, just down the hall.”

Then I poked my thumb into her pussy, just a little, not enough.

“Ask for it,” I commanded.

“Yes!”

“Louder.”

“Oh please, I want it, I want it!”

“What’s my name?”

“Sebastian, I want it Sebastian.”

“Beg me!” I slapped her on the ass.

“
Pleeeeease
.”

“I like it when you beg.”

I slapped her ass again, pulled her head towards me and put my tongue in her mouth, pushed her face down into the pillow, and ground the tip of my cock around the outside of her pussy in little circles, only allowing the tip in, and then taking it away. She was soaked.

“Please Sebastian.”

“Please what?”

“Please fuck me!”

“So dirty and bad!”

“I am,” she moaned.

I flipped her back over so she could look me in the eyes.

“You gave me a fake number. I don’t think you need this dick.”

“Fuck you!” She laughed.

I carried on with my story about the secret medieval affair, while I finger-banged her. She kicked her legs out play-violently at my chest. It was all part of the act. When she couldn’t take it anymore, I said, “And when the man sensed her moment of weakness, he pushed his dick into her!”

She laughed just as I penetrated her. “
Ohhh
,
mmm
,
haha
.”

“Shut up. I’m the writer,” I said, and pulled my fingers out. Then I spread her legs and pushed my cock deep inside and it was…

The loosest pussy I’ve ever been in. It was like sticking a wiener into a deep bucket of pudding. I tried various angles of attack: low to high, left to right, ass up, ass down; all while reciting
improv
poetry. She went mental, but I had to focus on the various whimpers, cries, moans and other sensations because my safely wrapped dick couldn’t feel shit. The wonderful girl, she came three times. She was designed for orgasms. She had a big, fat, magical pussy. I popped once, like usual. She was so fun, even with her broken muffin she still got me off.

And then I washed my dick. She walked into the kitchen and poured me a drink of water.

“Sorry but you can’t stay over,” she said.

“Oh. That’s ok.”

“I have homework.”

“Cool.”

And then I went home and posted the story on the forums, for my legacy. They loved it as usual, the faceless, horny men of the Internet. I was a bit bummed she kicked me out. I wanted a girlfriend.

“Good girl?” (Le
Guerrier
)

Sarah
texted
me and wanted to go out again. I was pretty sure she’d be
dtf
this time if everything worked out. I thought I’d blown it with my walk out on our last date, but she liked me. She was sort of masculine. I’d been meeting lots of girls that acted masculine lately. It was like they wanted to be the leader. I don’t like that. I like being the man. The best women I ever dated were from
Mexico
,
Brazil
, and
Columbia
. They’re still girls. North Americans have it all backwards. It’s a role reversal.

I’d been seeing
Montana
about twice a week, and the sex was great, but that’s all. We would fuck and then she’d kick me out. I’d never been with such an orgasmic girl. I could usually make her come three or four times a session, but she didn’t want anything else to do with me. It was like, the closer I came to being awesome with women, the further I was. In my head, I wanted to be a player, but really, I wanted a girlfriend. My standards are just higher than my attractiveness. I’m like a cute puppy that you want to cuddle, but I smelled like puppy pee.

I’d been reading two books called, A New Earth, and, The Power of Now, by
Eckhart
Tolle
. Now, before going out I would meditate for half an hour to get in The Now. I loved losing myself within myself. It’s like that scene in Being John
Malkovich
, where he crawls through the portal leading inside his own head. That’s what I’d been doing my entire life; crawling around inside of my skull, lost, pursued by
Minotaurs
.

Meditation is dope, but not as effective as cheap French beer. Practicing pickup seven nights a week was taking its toll. It makes you a little bit weird… no, a lot weird. I no longer saw people as people—just opportunities. I didn’t view women as women, but more like characters in a video game. Of course, it was different if they actually dated me, but I was frustrated from all the flaking. The only way to deal with the tremendous amount of rejection is to view the whole process as something separate from my reality, so it isn’t personal. As for approaching, it was really no big deal anymore. Just an action you take—something to do. Like making toast.

I met her at her place. Sarah was in her bra and Mickey Mouse boxers with a French cigarette dangling from her thin lips. Her feet were on the coffee table and she was painting her toes pink. I love pretty feet, not sure why. Cute toes, they just look like smooth little sausages or something. I leaned over and pinched her foot.

“
Ow
! No pinching, Sebastian.”

“I want to bite them.”

“What? Why?”

“They’re too cute.”

“You’re a weird guy.”

“Yeah. I am.”

She got dressed in a short white dress, and we left for a local bar to catch the first band. Sarah got a call so she stopped outside the bar to talk. I said I’d meet her inside. It was one of those hip French places and there were more pretty women than handsome men. It was some sort of feeding frenzy and I regretted being on a date in a venue with so many options. At one point, this little brunette cutie walked up and said something in French.

“Pardon,” I said. “
Je
ne
parle
pas
français
.”

“Oh, you are very handsome. I would like to buy you a drink.”

What? I almost gawked.

Montreal
rules. I’m standing here and this random French girl is pressing her breasts onto my arm and there’s Sarah at the corner bar staring daggers—poison eyes. I wasn’t too worried. I just smiled and waved. If she saw the girl approach me, well I probably looked pretty damn cool. Pre-Selection, baby. I’m the leader of men, and all that. I politely refused the drink.

Sarah had some big native dude with her; he looked like Jacob, the werewolf guy from Twilight. I said, “What’s up?”

He was harmless enough—I mean, he wasn’t trying to bang her, or he already did, so he wouldn’t be a cock-block. We put back a pitcher of draft then bounced to a party about twenty blocks south; a bit of a trek. I didn’t mind, it would give me time to practice my verbal game. Sarah wanted another drink so we dropped into this pool hall and ordered a few Gin n tonics. I went to the can, and when I was done there was a well-dressed man in a blazer and skinny jeans, sporting a curly mustache and a fedora whispering into Sarah’s ear; she was all toothy smiles. He was speaking in French. Not cool. I don’t know French. This guy was a threat to my bang. A real French seducer. I was surprised he wasn’t carrying a baguette.

I’m always a gentleman when it comes to these invaders. My strategy is to invite the cock-block into polite yet well-articulated banter, thus causing him to engage his logic. Men love logic, but nothing shrivels anxious labia like logic.

“Nice to meet you sir,” I said. “What do you do in
Montreal
?”

He snorted back in a thick accent, “I am ay
feelm
maker.”

“Non?” I said, caught off guard. This was bad, double-plus bad. He had a cool hobby.

“That’s so interesting,” Sarah said.

Bad-not-good. He didn’t use this story to brag, but instead I did. I brought it up for him. What a smart French bastard, obviously an advanced Dandy. I pulled at my straw and drank my gin.

“What sort of films do you make?” Sarah asked, playing with her hair, which was according to my books, an unconscious sign of attraction. I ordered another drink.

“Mon-Ami I am working on a story about love.” He took a long haul from his cigarette. Sarah’s friend rolled his werewolf eyes; I groaned.

“That’s awesome!” She said.

I didn’t want to seem like a dick; I needed to be abundant. There are many women and the universe will manifest all of my desires. I’d just pretend I was cool. They wouldn’t know I had to approach seventy girls to get this date, or that nine out of ten phone numbers led to nothing. They didn’t know about the deep dark,
Mordor
-like frustrations I’d endured, or of my glorious success.

“Can I see some of your films?” I asked him, thinking he had no films to see.

“Oh
oui
, I have eh many of my copies at my house, if you would be caring to watch
zem
. I also have
deh
Shiraz
, and eh, my bong eh.”

“Oh that sounds fun!” Sarah said with far too much damn enthusiasm.

Why did she even invite me out? Bitch. No, she’s not a bitch. She’s a woman and he’s a new shiny thing. I should beat him right on his stupid face. No, I’m good. I’m a good guy and I don’t care. I’m leading her right to him. This is bad. He may be a Jedi, like myself, or at least force-sensitive.

“Hey bro,” I said, “I really like your
Style
, it’s a fun
Game
, you have lots of
Mystery
.” He blinked a few times, said, “Merci,” and turned back to Sarah. I guessed he wasn’t in the French lair. He must be a natural douche-bag. That’s even worse, I thought. I even liked him. She must love him.

Then, in a flash of brilliance, I came upon my answer. Why resist? Be Zen. Go with the flow.

“Sorry bro but we have to go to this party. Hey, why don’t you come?” I said.

“Well
ehhhh
, I don’t know
ehhh
,” he mumbled, taking off his cap to wipe his brow.

“Yea come with us,” Sarah said.

I suppose it was my ego, but I believed I was better. If I gave her every opportunity to go with this guy, would she? Most guys would want to punish him, mock him, fight him. I’d do the opposite. Keep your friends close and your enemies closer, so they say. I had a secret. This was an Anglo party, a hipster party, and I knew many of these kids. This guy would be out of his element, and if worse came to worst I could meet some new girls. I’m like a pickup Dick Cheney.

“
Ehh
, of course I would like to be coming to
dis
party,” he agreed.

They conversed in French for the remaining ten blocks, so I talked to the Jacob the werewolf.

“I don’t like that sleazy dude,” he said.

“Yeah he’s alright, he’s got some game.”

“You need to do something.”

“I will,” I assured him with a pat on the back.

“No, you need to do something.”

“
Uhhh
, yeah, I know.”

“She likes you, but thinks you’re weird.”

“Most do.”

We walked quietly for another block. “How do you know her?” I asked.

“She’s my ex-girlfriend.”

“Oh. I see.”

We got to the house party and I left Sarah at the door. I high
fived
the first girl I saw just to look cool. I’ve known her all my life, I told myself, because if you don’t believe it Sebastian, nobody will. You always want to look like you’ve known everyone for years. Every stranger is your long-lost best friend. After a year of practicing cold approach pickup I was able to have a really good time in any party environment, even with complete strangers. While most people would stand in the background clutching their drinks and scrambling inside their skulls, I’d be meeting new people and having fun. I’d come so far from the nervous, depressed kid with bitch-tits. I suddenly wished I could be with my old friends back in
Vancouver
, just to show them what I’d done. But I knew they wouldn’t care, or understand. Maybe they would. Who knows?

I glanced back at
Frenchy
; he seemed incredibly out of place, eyes darting about in his head. She looked slightly put off too. Neither of them were talking to anyone.

Excellent!
Magnifico
!

You would think that ignoring the girl I came with, and leaving her in the clutches of a charming French man would be a terrible strategy, but it’s quite the contrary. Women are attracted to men of abundance. My complete lack of neediness or jealousy, my ability to attract other women before her eyes, with no regard for her feelings actually makes her more attracted to me. All this time, the French guy is trying to build rapport with her and I’m breaking it. It means I have standards, game, and freedom of choice. Or, so I hoped.

After half an hour of socializing and flirting with random, non-committal girls, I came back to Sarah and
Frenchy
. They were standing in the corner silently gazing, possibly bored. Superb, I thought. He ran himself dry.
Frenchy
again mentioned his house and his bong.

“Well,
ummm
, I’m with him,” she said, pointing at me.

“Good, good!” He said, stroking his mustache. “You will eh come
weet
us, no?”

“Sure, let’s get the hell out of this dump,” I said.

You wish pal.

As we exited the party and turned onto the main road, I flagged down a taxi. This was my chance—all or nothing, glory or death. If we went back to
Frenchy’s
house, I’d be done. He’d pull out that hookah, put on one of his brilliant short films and drag her to his room. I could picture the whole sordid affair and it wasn’t pretty. I put my arm around Sarah’s shoulder, looked at
Frenchy
and said, “Sorry man. We have to go. It was really nice to meet you.” His eyes narrowed, his shoulders slumped. Yes friend, this is what defeat feels like. I’m sorry, you were a fine opponent, but I’m a P.I.M.P. As I pushed her into the cab she looked back at him, then at me, then at the cab and back to
Frenchy
and said, “Bye.”

We drove off.

She looked at me accusingly. “Oh, you can find him on Facebook,” I said, reaching out and pulling her in.

I went to kiss her; she hesitated, gave me the stink eye, then submitted. We did it lightly a few times and then made-out. I put my hand on her thigh and with a newborn dove’s softness, grazed her pussy. Yes Sarah, I am marriage material. I am great. I am Sebastian, the pickup artist.

We got to her apartment. Anna was doing yoga in the living room, in the dog position. “Hi Anna,” I said as we passed by to Sarah’s room. She smiled at me. I think I liked Anna better than Sarah. Sarah’s sort of a bitch to me. I could have Anna, I told myself. I could have any woman. I could have a condo on Mars.

I shut the door and pushed Sarah to the bed, which was becoming my patented move. She pulled off her top, then the rest came off like a great event. I reached into to my pocket for the condom and she didn’t say anything, which was good. Some women will shut down at the first sign they’re about to get fucked. “It just happened!” They’ll say. A few minutes later I was behind her, strapped up and ramming her doggy style, with her head bumping into the wall, probably waking her neighbors. I felt pretty damn great about myself, so I blurted out, “Good girl!”

She stopped bucking her hips, looked back at me and said, “Excuse me? Did you just say good girl?”

I halted mid-thrust for a moment, stupefied. What is this, some sort of chick test? Oh right… she’s a feminist. I ignored her and continued pumping for another two minutes, I flipped her over a few times and blew my load in triumph. She wasn’t nearly as impressed as I was.