Wingman for a While Ch. 04

This chapter is a little longer. I didn't originally plan it this way, but it would help if you've already read my 'Gamers' series. You will recognize more of the characters. As always, thank you for the feedback and comments. It's nice to see familiar names among the readers. That's why I post on Literotica.

*

I saw Emmeline for the rest of May, and through June. We had good times together - sometimes with her friend Sandra, but most often just the two of us. We went bowling, saw movies, and just hung out, but avoided being alone at her place or mine. We went to a dance club, with Sandra, which turned out to be a huge mistake. Neither of us are very good dancers.

A slow dance came on, and I took her in my arms. My head knew that we were just friends, and that nothing was going to happen. But my lower body never got the memo. When I held her close, and felt the gentle pressure of her breasts against my chest, and when her thigh brushed mine ... well, the result should have been predictable.

I apologized, and she laughed it off. But neither of us found it very funny. I wanted Emmeline. Wanted her in every way. And I could have sworn that she was into me, too. But there was this stupid thing between us, and I was no closer to figuring out what it was.

We went to a baseball game. She enjoyed the ambience, and the ballpark, but didn't like the game so much.

- "It's too slow." she said. "Too much waiting. Look at those guys out there, waiting for the ball to get hit to them."

- "They're hoping it doesn't get hit to them." I explained.

- "That's even worse." she said. "That must be really stressful for them. They probably wish that they could run around the bases and whack people with their lacrosse sticks, like you do."

I had to take a closer look at her. She wasn't that much of a ditz.

- "You're messing with me, aren't you?"

She took a swig of her beer, and avoided eye contact. "Maybe. A little."

- "You're evil. Do you do that to Sandra?"

- "Not much. But you're so easy, it's hard to resist."

- "How is she?"

- "Good. How's your friend Rob?"

The truth was, I hadn't seen Rob since that night with the twins. The sex with those two redheaded fiends had been incredible. Mind blowing. But utterly meaningless. Plus, Rob had dropped about two thousand dollars on that one night, and I felt a bit guilty about that.

He was phoning me, leaving emails and texts, but I was ducking him. Truth be told, I think I was done with that side of my life.

I was still an asshole - it's hard to change a lifetime's work. But I was probably through with being a pussy hound. The twins had actually helped with that decision. I mean, if I couldn't totally enjoy that experience - one of the ultimate male fantasies - then my days of chasing tail were most likely drawing to a close.

I wanted Emmeline Kesthely. I didn't call her Lina so much, anymore. That was like her superhero name. But I knew her secret identity.

Only she wouldn't let me close. We went out together - but it was never a date. Something had to give, and I decided to force the lock. We saw a movie, and went for beers.

- "Emmeline," I said, "why won't you tell me what happened that weekend? What this ... obstacle is, this thing that's stuck between us."

She got that sad look on her face again. "Please stop asking, Max. I'm not going to tell you."

- "So you know what it is. You're keeping some ... dark secret from me. I thought we were friends. Friends should be able to tell each other these things."

- "We are friends." she said.

- "But you know that I want more than that." I said. "You know that I'm in love with you, that I think about you all the time. I've got 'Wild Horses' playing in my head twenty times a day. 'You know I can't let you slide through my hands.'"

"I want you every way possible, Emmeline. I want you as my girlfriend. I want you naked, in all your glory, in front of a fireplace."

She flushed at that, and couldn't meet my eye.

"The worst part of this - the part that's killing me - is that I think you want the same thing. You can tell me if I'm wrong. A friend would put me out my misery. Then I could get comfortable in the friend zone, and be happy there."

"Why won't you just tell me?" I pleaded.

- "A friend wouldn't do that." she said, softly. She looked up, and met my eye. She was sad - maybe even heartbroken. But I saw defiance there, too. If this was a contest of wills, I was never going to win.

"Maybe we should take it easy." she said. "Spend a little time apart."

My poor heart skipped a few beats. That was a horrifying suggestion.

- "No." I said. "That's a bad idea. A really bad idea."

- "You need some time, Max. Maybe we both do." She slid some money across the table. "Can you cover the tab? I'm going to head home."

She wouldn't let me go with her. She insisted that I stay.

***

I'm an idiot. That much I already knew. But I replayed that conversation with Emmeline in my head, analyzing everything she'd said. Something was tickling the back of my mind. But I was too stupid to figure it out.

And yet ... Emmeline had said a lot about friends. She obviously held to some sort of code, when it came to friendship. It was a bit like me, and my approach to being a team player.

So I contacted Sandra. She agreed to meet me for a drink after work.

I wasn't prepared for the first thing out of her mouth.

- "Hi Sandra." I said. "Thanks for -"

- "What did you do?" she said. It came out halfway to a snarl.

- "What did I do?"

- "What did you say to her? She called me up the other night, in tears. What did you do?"

I put my hands up, defensively. "Sandra - I'm sorry. You know that I would never willingly hurt Emmeline. I just ... I fucked up. Listen - can I get you a drink, and we'll start over?"

When she was a little calmer, I told her the whole story, from my perspective.

- "Something happened, at Blue Mountain. It had be Sunday morning - after she kissed me goodnight, but before I saw you in the parking lot. Everything changed in that span of time."

"I feel guilty, as if I did something, but Em told me several times that it wasn't my fault."

"Sandra - you know how I feel about her. I'm in love with her. Hopelessly in love with her. And I think she has the same feelings for me. But this damn thing is ... just sitting there, between us. Like a roadblock."

- "I know." said Sandra. "It's awful to watch."

- "Will you help me? Help us? You know what happened, don't you?"

Sandra sighed.

- "Yeah, I know." she said. "But I can't tell you, Max, much as I would like to."

- "WHAT?" My voice was so loud, everybody in the bar turned to look.

"Sorry. I'm sorry. But - are you serious? You won't tell me?"

- "Sorry, Max. Emmy made me promise not to tell you. No matter what. I begged her not to, but that's what she did."

I pleaded. I went down on one knee. But Sandra wouldn't tell me anything.

"I won't break a promise to a friend." she said. But that was all.

I was so frustrated that I wanted to punch a wall. It was a good thing that I took the subway home, because if I had been driving a car, I would have caused an accident, or else I would have been at the center of some horrific road rage incident.

Emmeline knew, and wouldn't tell me. Sandra knew, and wouldn't spill the beans, either. But once I thought about what she actually did say, I felt like an idiot all over again.

Like a complete idiot.

***

I answered Rob's latest email, and agreed to meet him. He got straight to the point.

- "Max, I need you, man. You have no idea how badly I need you!"

- "I'm listening."

- "There's this girl - her name's Ashley. I think I'm in love, Max."

- "You're what now?"

- "I'm serious. She could be the one."

- "Good for you." I even tried to put some enthusiasm into my voice.

- "Yeah - but there's a hitch. She won't go out with me unless I can get a date for her friend."

- "And this is why you need me?"

He gave me his most winning smile. "I need my wingman. Will you help me out, Max?"

- "How ugly is she?"

- "The friend? She's not! She's ... a 7. Or an 8. I swear!"

- "So she's fat?" I said.

- "No! Not at all. Max, I swear, she's hot. I just really need my wingman here. Hey - didn't I get you the twins?"

- "Yeah, you did."

- "So will you do it? Will you help me out, Max?" I had no idea why, but this seemed to be genuinely important to him.

- "Okay, Rob." I said.

- "Awesome! That's great!"

- "But I want something in return."

His eyes narrowed. "Like what? You can't have first choice this time. It's not about that."

- "No - I'm cool with that. I'll take care of the ugly friend for you. But I want to get together with those twins again. Just me. Solo. Can you give me their number?"

Rob grinned. "Are you sure, Max? Those two have expensive tastes. I know they liked you, but they won't put out for pizza and beer."

- "Do you have their number, or don't you?"

- "Yeah, I can fix you up."

- "Good. And there's one more thing. You remember those two chicks from Montreal? You got the pretty one; I got the fat one. Remember?"

- "What about them?" Rob was suspicious again.

- "I have a friend who just moved to Montreal. Nice guy, but a bit ... kinky. He likes the plus-size women. I'm going to be visiting him in a month or so, and I'd love to show him a good time. Hook him up, you know? And I wouldn't mind a crack at the pretty one myself. Did you get her number?"

- "That's all you want? Two phone numbers? And then you'll help me out with Ashley?"

- "You got it."

- "Deal." said Rob. He held out his hand, and I shook it.

We pulled out our phones, and I watched carefully as he gave me the twins' number.

- "What were their names, again?" I asked. "Melanie and ...?"

- "You're usually so much better with names." laughed Rob. "Melissa and Stephanie."

Then he gave me the number for the girls from Montreal. "I don't remember the fat one's name, but the cute friend was Louise."

- "Thanks, Rob." I said.

- "My pleasure, partner." he said.

So help me, I wanted to cold-cock him right there. He never remembered names, but he had them on his phone? I was 90% sure that he was a lying son of a bitch. There was one more thing that would give me that last 10% - and I suspected that it was on his phone.

- "So what's the plan?" I asked.

He wanted to impress this Ashley. She and her friend were from out of town, but he was ready to invite them to the Queen's Plate. It's a horse race - the oldest continuously run race in North America. The first one was held in 1860.

The royal family attends every now and then. The Queen came over for it in 2010. It's the first race in the Canadian Triple Crown, if you're into that sort of thing.

Rob was especially fussy about the arrangements. We had to wear suits, and everything had to be just right. The girls were staying at a fancy hotel, and we picked them up in a limo. When we met them, I could see - instantly - why Rob was in such a lather.

Ashley was a model. She was a 9. All dolled up for a photo shoot, she was probably a 10. Not my cup of tea, mind you, but if you like skinny models, then she was the real deal. Her nose was so high in the air, I suspect that she was trying to breathe slightly better air than the rest of us. She was all too aware of her physical beauty. But she had all the personality of a statue.

Her friend's name was Bethany. I disliked her at first sight. She was pretty enough, I guess - she had a nice dress on, and the fancy necklace and earrings. The two girls had probably spent a small fortune at the hairdresser's.

Bethany was a bitch. I'm usually pretty easy-going, and reasonably tolerant. But Bethany tried really hard to get me to dislike her - and she succeeded.

Professional baseball pitchers have to have two solid, dependable pitches. Usually, that's a fastball, and a curve, or a fastball and a slider, or cutter. Really good hurlers have three reliable pitches they can go to. If the curve isn't working for them that day, they can throw the change-up.

This bitch had four facial expressions. A frown, a sneer, and a move I would call the puke, where she pulled back her chin and lower jaw, as if she was about to throw up. Her fourth look I would describe as The Pick & Roll: her eyes would roam over the offending person or thing, and then she would roll her eyes in disgust.

Rob was oblivious, of course, as he assiduously paid court to the model, and left Bethany to me. That was, after all, why I was there. It was Jenny from high school all over again. It was Danielle and Diane. My job was to distract the bitch, engage her, keep her occupied, while Rob got the girl he was after. He had assured me that she wasn't fat, or ugly. But he knew damned well that the ugly was all on the inside.

Well, it just so happened that on this particular day, it fit in with my plans.

Woodbine racetrack was all abuzz, but I didn't give a shit. I told Ashley what a great guy Rob was, and tried to make nice with Bethany. She was in a foul mood. I don't know why - maybe it was her normal state, or somebody had shit on her corn flakes.

I got the impression that she didn't like Rob. Fair enough, but it was about the only thing we could agree on. I got Bethany a few drinks, but she just nursed them, and made faces after every sip as if they were made with bat guano.

Rob placed bets for the girls, on the preliminary races. Ashley was checking out the horses and jockeys, while Bethany bitched about the heat (it was quite humid, to be honest), the loud people, the lousy drinks, and so on.

Then Bethany started going out of her way to criticize Rob. She either hated his guts, or was jealous and over-protective of her friend. Whatever the reason, she was going to screw it all up. That called for a change of tactics on my part.

I started disagreeing with her. I questioned her assertions. When she treated me to her Pick & Roll, I just rolled my eyes right back at her. If I could get her ticked off at me, then she would climb off Rob's back.

It worked. She spent the rest of the afternoon being as unpleasant to me as humanly possible. It didn't bother me much; after today, I wasn't ever going to see her again.

I don't remember who won the Queen's Plate. Ashley won one of her $2 bets, and squealed like a little girl, while Bethany complained that the races were fixed.

I don't remember much about dinner, either. It was an ordeal, and I just endured. I kept throwing up topics for Bethany to criticize, or shoot down. This girl was something else. She had tons of energy - all of it negative.

We went for drinks in the hotel bar, and carried on our parallel, but completely unconnected conversations. Rob whispered in Ashley's ear while she giggled. Only a few feet away, Bethany complained, while I fielded her criticisms.

Then Rob gave me the thumbs up signal, glanced at the bitch, and raised an eyebrow.

I asked Bethany if she had seen the view of the lake from the hotel balcony.

- "Do I have to?" she said.

- "Oh, it's really nice!" said Ashley. "I've seen it, but you might really like it, Beth."

- "Fine." huffed the bitch. She got up, rolling her eyes, as if she was doing me a tremendous favour by walking out onto the balcony.

I pointed out Centre Island, the CN Tower ...

- "What's so special about it?"

- "It used to be the tallest building in the world." I said.

- "But it's not anymore."

- "Would you rather get a drink?" I asked.

- "I've had enough to drink."

- "We could go surfing." I said.

- "What?"

- "There's a little jazz bar on the other side of the hotel."

- "I hate jazz."

- "There's a surprise." I muttered.

- "What?" she said. "Never mind." She wanted to go back to the hotel bar. I went along, as slowly as I could. Of course, when we got back there, Ashley and Rob were gone.

"God damn it!" She was more than a little annoyed.

- "What's wrong?" I asked.

- "Where did they go?"

- "Upstairs - that would be my guess."

- "So they're fucking." she said.

- "That was kind of the point of the whole day." I said.

Bethany was seriously ticked off. She stamped her foot - dangerous, in heels - and swore. She gave me another scan, and rolled her eyes.

- "Bethany." I said, as nicely as I could manage. "What would you like to do? What do you want?"

- "Fuuuck!" she swore. "What I want is to get laid."

That wasn't quite what I was expecting to hear coming out of her mouth. Maybe I shouldn't have been surprised. Her friend Ashley was upstairs with Rob, while she was stuck with me. She must have been used to doormats, guys who would let her bitch all night, and then kiss her ass (Whereas I had been responding to her complaints with sarcasm and outright laughter).

- "Well then," I said, "let's go."

- "What?" Bethany looked at me - and for the first time, she didn't roll her eyes. "You?"

- "You get any better offers today?"

I waited for a count of three. She didn't have an answer.

"Didn't think so." I said. "Come on, then." I took her by the hand, and headed for the elevator.

- "Wait. Wait! Stop!"

- "What?" I pressed the elevator button.

- "What are you doing? You don't even like me!"

I was tempted to answer 'Who does?' Instead, I tried something more diplomatic.

"I don't have to like you. You're hot, I'm turned on. We can go fuck."

- "What?" She was obviously caught off guard. The elevator was already on the ground floor. It opened, and I pulled her inside. I hit 24 - the floor their room was on.

"You think I'm hot?" said Bethany, softly. She almost sounded nice.

The real answer, of course, would have been 'Hell, no!'. But at this point, I needed to get into the room where Rob and Ashley were. Also, I was completely fed up with Bethany's bullshit. I wanted to hate fuck her, to slam her through the wall, and into the next room. I wanted to jam my cock into my throat - just to shut her up.

For some reason - which I can't even begin to explain - I was hard as a rock. It might have been the couple of months of enforced abstinence. Or it might have been the overpowering urge to stick my dick in her ass.

I took Bethany's hand, and put it on the bulge in my pants. Her eyes went wide.

- "Oh, my God." she said.

I placed a hand behind her head, and then pushed her back, against the wall of the elevator. I kissed her, hard. My other hand went beneath the hem of her dress, and I grabbed her upper thigh, before working my fingers upwards. I slid my hand under her panties, and cupped her pussy. Bethany groaned into my mouth.

When the elevator stopped, I released her.

- "So? You coming?" I said.

- "I sure hope so." she said, with a girlish giggle that just fit.

We entered their room. It was dark - there was only a single lamp on - but we could hear Rob and Ashley grunting and panting. Bethany's hand went to my crotch. She was so turned on, she forgot to complain.

I pulled her dress over her head. She wasn't wearing a bra. She had floppy, natural breasts, with large areolae. I palmed them, and thumbed her nipples. Rob had been right: she had a nice body - despite her ugly personality.

Her panties came next. I wasn't about to go down on her, though. For one thing, it had been a humid day, at the racetrack, and she wasn't likely to be fresh down there. Besides, I didn't like her enough to eat her pussy.

So I fingered her, and sucked on her nipples. Then I pushed her back, and got my pants off. Ashley seemed to be climaxing, in the other bed. It didn't matter.

Bethany went to her knees, and took my cock in her mouth. She wasn't particularly good at it, but at least she couldn't complain while her mouth was full.