Wingman for a While Ch. 01

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This story features Max, one of the characters from “Gamers”. It’s not necessary to read “Gamers” first. And a warning: the two stories are very different. Ever see the movie ‘Alfie’? (the original, I mean – with Michael Caine)


This isn’t an easy story to tell, because no matter how I tell it, I come out looking like an asshole. Well, I suppose I was – but I’ll let you be the judge.

Back in high school and college, I was a triple threat. First off, I was an athlete. I ran track, started at slot receiver for the football team, and played hockey and lacrosse. Most everybody recognized me around campus – if not for my athletics, then for my outrageously red, outrageously curly hair.

But I was also a board gamer, with a tight a circle of friends. We played twice a week. My buddies were almost religious about it. They never missed a game. I tried not to, and I was always able to balance sports and gaming pretty well. But there was one thing that could interfere with my schedule.

Pussy. I was a dedicated pussy hound. Some guys called me a player – it was a pretty accurate label. I might have done even better at sports, if I wasn’t so obsessed with chasing skirt. I even broke the bro code. My friend Gerry was interested in this cute girl named Maria Fernandes. He’d had a wild crush on her since about 6th grade. But he wasn’t going to get anywhere with her – not in a million years.

I banged her at a party, in a friend’s bedroom. I dated her a couple of times, and had sex with her again. But she wasn’t that special, and when she started making demands, I dumped her. Gerry found out that I’d been doing her, and he was really hurt. I felt bad about that. The guys decided I had to make it up to him, by doing his English homework for a month. I also had to bring a case of beer to our next game. No big deal.

Then my buddy Dean got into this group of gamer girls. I connected with one of them – Cyn – but she turned out to be a nasty piece of work. I also hooked up with Angie – nice girl, great tits. But she was going away for the whole summer. I wasn’t about to become a monk for three months, so I dumped her.

Not a very nice thing to do. I know.

My friends started getting serious. Les had Lucy, Gerry had Trisha, and Dean even moved to Australia to be with Jazz. That little circle was played out for me. Besides, I got an offer to play professional lacrosse, and that sounded pretty cool.

So off I went, Toronto-bound. I got another job – pro lacrosse didn’t pay enough to live on, back then, unless you were a superstar. I worked my ass off, night and day. My boss was pretty understanding about my lacrosse schedule, and he was proud to have a professional athlete in the office.

There were a couple of lacrosse groupies, but I wasn’t meeting very many women. New city, shortage of women where I worked, weird schedule … these all contributed to creating a bit of a nookie slump.

But that all changed – everything changed – when I was out late with a few guys from the team. We were at a cigar bar. You know the style: pretentious, overpriced, filled with know-it-all showing off their knowledge, or swearing that nothing could ever match that Cochiba or that Rocky Patel, or that Monte Cristo they had that one time … Honestly, the only thing worse is listening to guys talk about their golf game in agonizing detail.

– “Max!” I heard my name called.

– “Rob?” It was an old high school friend and teammate of mine. Rob played tight end on the football team, and centred my line in hockey. His family had serious money, though, so while I went to college locally, with most of my friends, Rob went off to a more prestigious university.

– “What are you doing here?” he asked. “I haven’t seen you in years!”

Rob was suitably impressed when I told him about the lacrosse. “What about you?” I asked.

– “Got my foot in the door at K_____.” he said, naming a prestigious investment firm.

– “Cool.” I said. That was way out of my league.

We reminisced about high school sports for a while. Rob led the league in scoring one season – mostly because I led the league in assists, setting him up. He was a big boy, and he could shoot, but it was ol’ Max digging the puck out of the corners, and doing the grunt work that put him on the podium. I did it for the team; Rob was obsessed with his own personal stats.

He did buy me a drink, though. Then we talked about people we remembered – who was where, and what they were doing. We didn’t have a lot in common otherwise. We exchanged phone numbers and email addresses.

– “I’ll give you a call – we can get together.” he said. It sounded like the usual empty promise.

– “Sounds great.” I said, equally insincere.

It came as a complete surprise when he called me two weeks later.

– “Max! How are ya, man?”

– “Rob? I’m good. What’s up?”

– “Listen,” he said. “your season doesn’t officially start until December, right?”

– “That’s right.” I was surprised Kolej Escort that he knew that.

– “You free this weekend?”

– “What do you have in mind?”

– “Myrtle Beach. Your flight and accommodation are covered. What d’you say?”

I was a bit stunned. Rob explained: “I have some business to take care of on Friday, and the rest of the weekend to play. The guy who was supposed to go with me bailed out. The seats are booked, the room is waiting … so I thought of my old wingman. How about it?”

Easy decision. “I’m in.”

– “Awesome!” said Rob.

So I ended up flying to South Carolina with a guy I hadn’t seen since seen high school. When he called me his ‘old wingman’, I thought Rob was referring to hockey. He wasn’t.

– “Remember that time, at Riverside (our high school) – you were covering for me, when I was behind the bleachers with that chick? The one with the huge rack?”

– “Mary-Ellen Koren?”

Rob turned in his seat to look at me. “You remember her name?”

I remembered that whole episode. Rob was my teammate at the time, and he asked me for a favor. There was a girl he was interested in. He wanted to get her alone, but she had a friend, Jenny, who was like her Siamese twin – joined at the hip. Rob wanted me to keep Jenny occupied, or at least distracted, while he put the moves on Mary-Ellen.

Jenny was plain, flat-chested, and painfully awkward. She had these enormous braces, too. I remember that she hardly ever opened her mouth, for fear that somebody would laugh.

Rob and I sat down next to them. Mary-Ellen didn’t seem too surprised, but Jenny was obviously flustered. I started asking her about our math homework (we were in the same class), and then moved on to movies, her hobbies, her favourite things to do.

The poor girl was panic-stricken. She had no idea why a guy would even be talking to her – much less as nicely as I was. She kept turning to her friend for support, but Mary-Ellen was giggling at whatever Rob was whispering in her ear. No help there.

I hinted to Jenny that I had something to ask her – something important – but that I was too shy. Would she mind – could I talk to her in private?

She followed me, as I slid a little further down the bench. Rob didn’t waste any time. He disappeared with Mary-Ellen thirty seconds later. Jenny nearly freaked out when she couldn’t see her friend nearby, but I soothed her, and calmed her down. I just kept hinting that I had a really important question to ask her.

Poor Jenny must have thought that I was going to ask her out. I made it seem like I was nervous, too hesitant to get the words out. It was a bit like fishing, really. I just kept giving her more line. She had no way of knowing that I was never going to reel her in.

Well, Rob got caught by Miss Howell, the phys ed teacher. He had his hand inside Mary-Ellen’s shirt, and his own pants half undone. They each got a week-long suspension for that. Honestly, it was stupid. Getting into a fight would only get you three days.

My little discussion with Jenny was interrupted, too. The next day, she somehow found the courage to come over to my locker. With her head down, and her lips barely moving, she managed to say:

– “Max? What were you going to ask me?”

And I came out with an instant classic, right on the spot.

– “Oh – I just wanted to know, Jenny: do you think the Leafs will make the playoffs this year?”

Yeah, I was an asshole.

But Rob thought it was pretty funny. So did the hockey team, and most of the jocks. In fact, my line became a kind of catch-phrase. Everybody started using it.

I didn’t need hindsight to know that it was a cruel thing to do. Poor Jenny was traumatized – she didn’t even go to the Prom, for fear that somebody would use that line on her. Rob never saw it that way, of course.

– “Man, I was so close! Another minute, and I would have been in her pants!” he said.

– “Sorry about that.”

– “Not your fault, man. You did an amazing job. Best – wingman – ever.”

To borrow a line from the movie ‘Casablanca’, it could have been the start of a beautiful friendship. But we had little in common. I was an athlete, and a gamer. I hung out with the jocks. Rob played sports, but he was a rich kid. His parents bought him a fancy car for his 18th birthday, and he hung out with the other rich kids.

But now his money, or his job, was providing me with a free trip to Myrtle Beach. And Rob was talking about the action we’d see later that night.

The weather was ok. I got in a little pool time while Rob took care of the work he had to do. When he got back, though, he was all business. We went on a shopping run, for a bottle of vodka, and some of those vodka coolers that taste so sweet, but pack a real punch. Condoms, and lube too. I wondered if he was going to claim them on the expense account.

Then he insisted on a nap – for both of us.

– “You’ll need your Rus Escort strength, later.” he told me.

Rob took me to me a seafood place he knew, where we downed a few dozen oysters, and had a few beers. Not too many, though. Rob wanted me in what he called ‘fighting trim’. He had everything planned.

– “The losers go to the beach, or to the pool, to try and pick up chicks. Sure, they look hot in their bikinis, and it’s nice to scope out the merchandise. But they still want to party, at that stage. They aren’t ready to commit to a guy for the whole night. What if a better offer comes along?”

“You and me, Max: we’re that better offer. After a swim, the girls get dolled up, and they go for dinner, have a few drinks … a few laughs with their friends. Then they get a little crazy, and decide they want to go to a club.”

“That’s where we’ll find them.”

– “You think we’re going to pick up a couple of girls tonight?” I asked.

– “I know we’re gonna score tonight. No doubt about it. Stick with me, Max.” he said. I had to laugh at his confidence.

Rob told me his theory. “Girls who dress up nice, get all made up, and go to the club – they’re thinking about getting laid. They’re not fully committed, or anything. But it’s a distinct possibility, if the right guys are there.”

– “Guys? Plural?”

– “They don’t travel alone, Max. Girls travel in packs. But they work in teams of two, if they’re in the mood. A wingman – just like we do. Except a girl’s wingman is also there to talk her out of doing something stupid.”

– “And that’s where I come in?”

– “Follow my lead, Max. Just follow my lead.” said Rob.

He was a big, handsome guy – taller, and better-looking than me, anyway. Rob was also a smooth talker. Almost too glib, if you asked me. But it seemed to work for him.

He took me to a typical trendy club, with the expensive cars parked outside. No waiting in line for us; Rob knew the bouncer, and slipped him some cash. Inside, it was horrific. The noise (I wouldn’t call it music) was deafening, and I could barely see. It was pitch dark, except when they let loose the light show – and then I was blinded. Not my scene.

But Rob seemed right at home. For one thing, there seemed to be twice as many girls as guys. He went to work immediately, chatting up a pair of hotties. I couldn’t hear a word he said. They probably couldn’t, either. Judging by the looks on their faces, they weren’t all that impressed. After about five minutes, he pulled the plug.

He pointed, and led the way out back, where there was a huge deck. The pressure on my ears was much less. Rob didn’t seem at all fazed by getting shot down inside. He found another couple of cuties, and went right at them.

Their names were Capri and Dani. They were either half-drunk, or just not very bright, because now that I could hear what Rob was saying, I had to try not to laugh. He told them that he was a sports doctor, and that I was his prize patient, a famous lacrosse star.

– “You’ve never heard of Max?” he asked them. His tone implied that they must have been living under a rock, if they didn’t recognize me. Both girls peered at me, trying to figure out who I was.

– “He’s cute, I guess.” said Capri.

– “Damn straight.” said Rob. “If I was a girl, I’d be all over him.” He put his arm around me, and squeezed.

– “Easy there, Doc.”

I probably contributed about 10%. The other 90% was Rob’s amazingly simple line of bullshit. I’m still not sure how he did it, but within half an hour, he got these two girls to agree to come back to our room for a party.

Capri was a cute little brunette, with a bit too much red lipstick. Dani was taller, with legs till Tuesday, which her super-short red skirt did nothing to conceal. On the way out, to get a taxi, Dani grabbed my ass.

– “I love athletes.” she whispered in my ear.

Back at our hotel, Rob produced wine coolers for the girls, and a shot of vodka for us. He steered little Capri to the couch. That left nowhere to sit for Dani and me. I perched on the edge of the bed, and she sat down right next to me.

When Rob leaned in to kiss Capri, Dani let out a moan, and reached up to grab my hair in one hand. She pulled my mouth to hers, and stuck her tongue in my mouth. I don’t remember what I did with my drink. Somehow, I got rid of it, though, because I had one hand on her breast, and the other on her ass, under her diminutive skirt.

She shed her clothes faster than I could remove them. I had her on her back, naked except for her heels, with my head between her legs. She had a sweet little pussy. Dani was definitely primed for action: it seemed like only a moment later when she pulled my hair with both hands.

– “Gah! Cumming!”

I glanced to my right. Rob had Capri, sitting on the edge of the bed, with her dress around her waist. She had his cock in her mouth. Robe winked, and gave me a thumbs up.

Dani wouldn’t wait. Yenimahalle Escort She pulled me up on the bed. I managed to skin a condom on while she rubbed her own pussy lips. She was very wet, but Dani nearly bent my dick in half when she tried to jam herself on the end of my knob. I pushed her back on the bed, and with three or four thrusts, got a firm lodging. Then I was all the way in.

She was enthusiastic – I’ll tell you that for free. Dani humped and hunched, trying to slide her pussy up my dick. It was a frantic, hyper-energetic fuck, with lots of slapping of body parts. I think she came again.

Then she wanted to change position. Dani got onto her hands and knees, and I slipped into her from behind in one long, delicious thrust. But she was in no mood for finesse. She started slamming her ass back at me, groaning every time I hit bottom.

On the bed beside us, Rob was fucking little Capri in the same position. It was pretty wild: two couples, both going at it doggy style, only a few feet apart. I’m not shy, and certainly not inexperienced – but I’d never seen anything like this.

I was amazed when Dani turned her head to grin at her friend. And then Capri gave her a thumbs up in return!

Rob grunted as he came. I had a little more stamina – maybe because I was going down on Dani while Rob was getting a blowjob. He and Capri watched as Dani and I continued trying to pummel each other.

– “Aargh!” I groaned, spraying the inside of the condom full of semen. I collapsed on top of Dani, and then we both slid down together, with my arms around her.

But we didn’t cuddle for very long. The two girls were looking at each other. I couldn’t see Dani’s face, but Capri was smiling, as they had an extended conversation without any words. To my amazement, Capri was playing with herself with one hand. Then she said it.

– “Switch?”

Dani laughed, and slid from my arms. She and Capri traded places.

– “Hello.” said Capri, as she pressed her delightful little body against mine.

– “You’re incredible.” I said.

– “Better believe it.” she said.

Capri wasted no time getting me ready for action again. She slid down the bed, and took my organ in her mouth – even covered in my spunk, from the inside of the condom. The situation was so unbelievably wild, that I was hard again in no time.

She wanted it from behind, too. When she got on all fours, and tilted that tight little ass up at me, I was a lost man. Capri wasn’t as crazy, in terms of her movements, as Dani had been, but there was no question that she knew what she wanted. I fucked her from behind until she came. Then she put me on my back, and climbed aboard.

When I looked to the other bed, Rob had Dani on her back. Her long legs were up around his ears, as he plunged into her as if he was trying to nail her to the mattress.

– “Oh, yeah.” mumbled Capri. She was enjoying the sight as much as I was.

I’m pretty sure that I came inside Capri (inside a condom). I have a vivid memory of Dani sucking on my dick later, so there must have been a third round. But I also remember fucking Capri again, on her back, with my lips around her little pink nipples.

It was easily the wildest night of my relatively short life.

In the morning, Rob let the girls shower and clean up, but then he packed them into a taxi and shipped them out. They were obviously tired, and a bit hung over; they didn’t have the energy to complain.

Rob was on his phone several times, before he turned to me.

– “You play golf, right?”

– “I can.”

– “Sorry about this. Change of plans. My boss wants me to meet this big investor, and play a round with him. Can you help me out?”

– “Sure.”

What else was I going to say? I suspected that this golf game wasn’t a last-minute thing – that Rob had known about it all along. But how could I argue with a guy who got me a free trip to Myrtle Beach, and got me laid?

The old guys were harmless enough, I suppose, though they were a bit full of themselves. The problem, though, was the golf. I’m not bad at it. It just takes so damn long. On a Saturday afternoon, with good weather? Over five hours to play 18 holes.

Then we had to do the obligatory 19th hole – several rounds of drinks. After that, the old guys invited us to dinner, more drinks … by late evening we were three sheets to the wind, and pretty tired. No cruising the clubs for us.

– “Sorry, man.” said Rob. “I’ll make it up to you.”

– “No harm done.” I told him.

***Round 2

Rob called me a week later.

– “Can we use your place for a little party? Saturday night?”

A word about our respective domestic arrangements. I shared an apartment with a guy from work, named Pete. Rob, on the other hand, lived with his parents, in their exclusive downtown condo. “I’m saving money for a place of my own.” he said.

– “I’ll find out.” I told Rob. As it happened, Pete was going away for the whole weekend with a group of buddies.

I gave Rob the green light.

We met up that Saturday night for a drink, and then Rob took me to a Scottish cultural event. Men in kilts, bagpipes … it wouldn’t have been my kind of scene, but I have to admit, girls look good in those kilts, with that tartan sash over their shoulders – whatever you call it.

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