Author: Backstory
Title: Old Friends 01: The Bet
Part: Chapter 01
Universe: Old Friends
Summary: Childhood friends Shauna and Aaron get together as adults.  While playing pool, a little sexual tension leads to a sexy bet...
Keywords: MF, intro, reluc, oral

by Backstory
will.backstory@googlemail.com

Old Friends - Chapter 01: The Bet
(MF intro reluc oral)

IMPORTANT DISCLAIMER!
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This story is intended for individuals above the age of 21 or above whatever age the local jurisdiction of the reader would dictate.  None of the characters of situations are real, or even based on any real people or events.
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Chapter 01: The Bet (MF intro reluc oral)

Shauna walked into the bar, scanning the crowd for Aaron.  She was in town for a few weeks for a business conference and had decided to look up her childhood friend.  She saw a man who she thought had to be him, though he was much taller than she remembered.  He seemed to be looking at her, too, though that was no guarantee.  A lot of guys stared at her.  She walked up to him tentatively.

"Aaron?"  He smiled and walked toward her.  "Aaron!  Oh my God, you grew!"

He smiled.  "Yeah, I thought you might grow a little, too."

"I did!" she said indignantly, "I grew a lot."

"You look like you're four feet tall."

"Hey, I'm 4'11".  You've seen my parents.  We're lucky to hit five feet in my family.  My brother's really bummed.  He's 17 and he's only 5'3"."

"That sucks.  You look like you don't even hit 100 pounds."

"103.  So?"

"Yeah, well at least you don't dye your hair blonde like every other girl with dark hair."

"Yeah, I'm totally natural."  She caught him stealing a look down at her C-cup.

"Totally natural?" he asked.

She swatted him, laughing.  "Yes, you pig."

He laughed.  "We should play some pool.  For old times' sake."

"Need your ass kicked that bad, huh?"

"Come on, let me buy you a drink."

He played as badly as she remembered and she beat him before he got any of his balls in.  He even hit one of hers in for her.

"You're as bad as I remember." she said, jokingly, "Let's play a game of air hockey so I can humiliate you more."

They did, and she she did.  7 to 2.

"You never were any good at these games, but you always love to play.  Some sort of masochistic streak, huh?"

"Yeah, I guess.  You know what, though?  I think it's because there's nothing at stake, you know?  It doesn't matter if I win or not."

"So if we were to bet something, you think you'd beat me?"

"Maybe."

"Ok smart ass, lets do it.  I'll bet you 25 bucks."

"Make it fifty."

"Hey, let's not get crazy, I don't have fifty."

"Ok.  I'll put up fifty, you put up your twenty-five and a look at your tits."

This took her totally by surprise.  "Aaron, I had no idea!"

"What?  I saw them when we were nine, but I didn't really care then.  They weren't so..."

"So what?"

"So... wagerable."

She laughed.  "Fine.  You aren't winning anyway, horndog.  My twenty-five bucks and a peek at my tits against your fifty."

"A look, not a peek."

"Fine, lawyer-boy, a look.  Let's shake."

They shook, and she proceeded to beat him 7 to 0.

"Man." he said.

"Don't be so bummed.  Double or nothing."

"Nah take it." he tossed her the fifty bucks, "I wasn't invested in that game.  Let's have another one, though and I'll put up a hundred bucks this time.

"You know I only have $75.  Well, seventy-five and my tits which are apparently worth $25." she wiggled her tits a little, then hid her face and laughed.

"I know I know.  You can put your money away.  I will wager $100 against you having sex with me tonight."

"Aaron!  Do you like losing money?"

He grinned.

"You want to have sex with me?  This isn't the usual way men go about that with me, you know."

"So you're saying I might be able to get it for free."

She though for a minute.  "No.  No, I don't think so.  I think this bet is a good idea after all."

"Alright." he said taking out a hundred dollar bill.

"Alright," she said, smiling flirtatiously, "a hundred bucks against you and me gettin'  busy."

They played again, but this time, he won.  7 to 6.

"Holy shit, I don't believe it." she said.

"So, are we headed to my place or yours?  Or do you want to do it right here?"

"Hey, all jokes aside, Aaron."

"I'm not joking."

"What, do you want your fifty bucks back?" she asked.

"No, way, Shauna, you gotta pay up this time."

"You're not going to make me do this are you?"

"Of course!  We had a bet!"

She looked at him in disbelief.  "I don't believe you're really gonna..." she leaned forward and whispered "gonna make me fuck you."

"Is it that bad?"

She sighed.  "No, but we grew up together man.  It's weird!  I haven't seen you for 15 years and now we're just gonna have sex?  Can't we do another wager?  Double or nothing?"

"Double what?"

"I don't know, it was the nothing I was thinking about."

"What game?"

"Pool.  I know you can't beat me at pool."

"You're probably right," he said, "so why should I risk it?  What's the double?"

She thought.  "You can fuck me twice."

"That's it?"

"What do you want?  What else can I put on the table?"

"Well, here's the way I see it.  You already gotta fuck me."

"Aaron..."

"Hey, that was the bet.  I won.  Am I going to risk losing that so I can just do it twice?  I don't think so."

"So what do you suggest?"

"You put you ass really on the line."

"How?"

"You're visiting for a few weeks, right?"

"Yeah."

"If I win, I get to fuck you twice, in the front and in the back."

She stared, uncomprehendingly for a minute, then laughed.  "You want butt sex?"

"Yeah, that's right."

"Dude, what is it with men and my ass?  Listen, you fucking me is weird, okay?"

"If you say so."

"It is."  She paused to take another big sip of her beer.  "So if you fucking me is weird, don't you think you fucking me in my ass would be even weirder."

"I don't think I'm going to feel weird..."

"Aaron..."

"Hey, I probably won't win anyway, right?"

She considered, then finished her beer.  "It'll be pool?"

"Yes."

"You know what?  You're right.  You're not going to beat me at pool, so I can wager all the butt sex you could ever want."

"You know, you're right... maybe we should forget about any more bets."

"Hell no.  Lets shake on it so I can get out of this mess."

"I don't know.  Maybe we should just go back to my apartment..."

"What?"

"I don't know if this is enough to entice me.  What else will you offer?"

"What else?  Aaron!  I just basically said I'd let you stick your dick up my ass if you win.  What else you want?"

"Will you suck my dick?"

"Uh, yeah."

"Twice?"

"Fine, twice."

"Do you swallow?"

She sighed.  "Men.  Yes, I'll swallow, now do we have a deal?"

He looked her up and down.  A pretty big part of her wanted to fuck him anyway, but not like this, and not on her first day here.  Maybe after a week or two.

"Okay.  Deal."  They shook hands, ordered more drinks, and walked back to the pool table.  As the game progressed and Aaron sunk the first three balls, she had a sudden realization.

"You hustled me."

He smiled, and sank another.  "Who, me?  So I've played a little pool since we last got together."

"She hit him.  I can't believe you fucking hustled me!"

"Are you going to let me finish?"

"I'm not even going to get a shot!"

"No, probably not."

She didn't.  He finished the whole table on one turn and sunk the eight-ball in his called pocket.

It was a hustle, no doubt about it, but a deal was a deal.  She tried to stay in control.  "Okay, sex fiend, your place or mine?"

"You seem remarkably calm."

"Yeah well..."

"Yeah well, come on.  You're giving me my first payment right now." He grabbed her drink and took her hand.  He took her over to the one restroom in the back and flipped on the light.

"Oh no.  You are NOT fucking my ass without lubrication, Aaron."

"Of course not.  Just come in."  They went into the john and he closed the door.  He pointed to the toilet. "Have a seat."

She sat down nervously.  She had had her share of sex in the last few years, but she wasn't at all sure how well she was going to take this.  She watched as he took off his shirt, revealing a well muscled chest and a sexy six-pack. She was starting to get a little excited as he unbuckled his belt.

"Let me." she said, surprising herself a little, and pulled his pants undone, letting them fall to his feet.  She saw his dick pushing out his boxer-briefs and felt a little afraid.  "You didn't tell me you had grown down here, too!"

"When you saw me naked I was only eight years old, of course I got bigger!"  He smiled.  "Turns out I'm a little above average, too."

She slid his underwear down, pulling his cock into her hand and looked at it.  It was bigger than any of her previous boyfriends' and very thick.  "How big is it?" she asked.

"Eight inches."

She gasped.  "You are NOT getting that thing anywhere NEAR my butt.  I'll give you a hundred blowjobs if I have to."

"A deal's a deal.  Right now, I'm just going to cash in one blowjob.  I'll have your ass later."

She looked at the semi-hard cock in her hand.  She could barely get her hand around it.  It was impossible to think of him fitting it in her pussy, nevermind sticking it up her ass.  She looked at it for a minute more and decided she'd give him his money's worth.  She opened her mouth and carefully took it in, getting about half of it in before her mouth began to feel stretched.  She felt the tip pushing against the back of her throat and fought of her gag reflex.  After a moment, she began to move her head back and forth, letting Aaron's cock slide in and out of her mouth.  

After a minute of this, he grabbed her hair and pulled her forward, pushing hard into her mouth.  She'd done deep throat before, and pretty well, she thought.  Now, she tried to relax and open her throat up, allowing Aaron's dick to push its way down.  He groaned appreciatively and started to fuck her throat  Her pussy was now begining to feel seriously hot, but Aaron was thrusting really hard and she soon choked and had to spit him out.

"I'm sorry." she said, wiping tears from her eyes, "I'm just not used to, you know... so big.  Do it again."

He grabbed her hair on both sides of her head and pushed his big cock past her lips.  Again, she relaxed as he pulled her head toward his stomach, pushing his cock down her throat.  She felt his pubic hair brushing her nose and thought about how long and thick his cock was knowing that right now it was down her throat.  He pulled it back and started fucking her throat, more slowly this time.

She was definitely getting off on this now.  The feeling of his hard dick filling her mouth and throat made her pussy cry out for attention.  She licked at Aaron's cock and played with it as it slid over her tongue.  She was getting very wet and struggled to put a hand down her tight jeans.  She no longer considered the size of his dick a problem.  In fact, she very badly wanted him to put it in her pussy.  When she finally got her hand in her pants, she fingered her clit wildly, cumming almost immediately.  Aparently this sight sent Aaron over the edge and he started to grunt.  His cock slid out of her mouth and she watched, fascinated as he pumped it in front of her face.  He grabbed the hair on the back of her head and she opened her mouth for his cum.

His pumping slowed and he aimed his dick right into her mouth, the tip just insider her open lips.  His cum was thick and salty and it completely filled her mouth.  She held it there until he was done, then swallowed it in one gulp.  As he became soft, she took him into her mouth and licked him in what she hoped was a very sexy way.  After a few minutes she could feel him getting hard again and she reached down to lift up her shirt.  His hand stopped her.

"Wait." he said.  "My place."
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(C)Copyright 2010 by Backstory
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