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Tiffany Lost The Bet
Mentoring was never so much fun. - by: Anthony

I looked out my window and smiled at the view.  It was a cloudy day, but the Metrodome was still visible—the benefit of working on the 35th floor.  I took a drink of coffee and wished for the thousandth time that the cheap-ass company would spring for some decent coffee, for once.

A sound behind me caused me to turn.  Jim stood in the doorway of my cubicle with my new protégé.  The goddamn company always passed me over for promotions (six fucking times!), but they still expected me to show all the newbies the ropes.  I was damn good at my job, but I’d be damned if I would ever show any of the greenies the tricks of my trade.

“This is Tiffany,” Jim was saying as a girl stepped out from behind him.  “Tiffany, this is Anthony, your new mentor.  This man is a genius at selling upgraded services to our clients.  If you can weasel that information out of him, you’ll be set.”

I ignored Jim, as usual.  He was technically my boss, but he was a balding imbecile that only had his job because he was married to the CFO’s niece.  Tiffany, however, bore a second look.  She was petite and very cute, with bouncy hair and a chest that was barely contained by the low-cut top she wore.  Her breasts swelled up out of the neckline like twin moons.  She was a bit on the chunky side, but that could be overlooked when your hands were gripping melons like those.

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“Hi, Tiffany,” I said warmly and shook her hand.  I got her situated with coffee and a chair and went over the basics with her.  By the end of the day, I was surprised to find that she was the only person I’d ever trained that I actually liked.

A few days later, Tiffany asked, “Like the Vikings much?”

I grinned at her and let my eyes slide over my beloved Vikings paraphernalia.  I had posters, banners, bobble-heads, a signed football in a glass case, and every sort of knick-knack imaginable.  Several of the employees referred to my cubicle as Viking Central.

 “Just a bit,” I admitted.  Tiffany gazed at one of the posters and I took the opportunity to admire her chest.  A bit of pink lace peeked up from the edges of her black shirt today, begging for a tongue to slide over—and under—the material.  I scooted my chair forward to hide my sudden erection, and opened the latest worksheet I’d been showing her on the computer.  Damn, some days it sucked to be married.

Tiffany swirled the wine in her glass and watched the “legs” trickled down the curved edges.  The nice thing about working in sales was that the company turned a blind eye to liquid lunches, and paid the expense reports without batting an eye.  I never abused the privilege.  One beer over lunch was my max.  I took a drink and set the bottle down.

“What’s wrong?” I asked as Tiffany picked at her salad.  I’d been mentoring her for just over two weeks, and we had been having lunch nearly every day.  We always picked public places, so my yapping coworkers couldn’t cook up any rumors.  Sometimes we even invited Sally from Accounting.

“Why don’t you ever tell me anything useful?” Tiffany asked.  I raised an eyebrow, surprised.  Sometimes I thought of Tiffany as a cute, dumb blonde, but she was really quite sharp.

“All you ever show me is routine stuff.  I want to know how you sell.  I mean, how you really do it, because you must have a technique, or a style, or some sort of method to succeed.  You never talk to customers when I’m around.”

I shrugged.  “The bastards have already made it clear that they’ll never promote me.  They think I’m an ass, but they keep me because I perform.  Why should I pass my knowledge on to someone else?”

Tiffany glared at me.  “You’re supposed to be my mentor!”

“I am, but I’m not going to cut my own throat.  I have two kids to feed and, eventually, put through college.”

She looked away.

“Is something else bothering you?” I asked.  She’d been acting weird all day.  She shrugged.

“I guess.  My boyfriend and I are fighting.  It’s never gone on this long before.  We haven’t had sex in two weeks.”  She made a huffing sound and I nearly choked on my beer when she added, “And then the jerk expected me to give him a blow job in the kitchen this morning, like nothing was wrong.  The fucker.  Just because he’s addicted to my BJs.”

My mouth went dry.  “Do you… give those often?” I asked casually.  My wife had a severe deficit in that particular area.  She hated giving head.  On the few occasions she had tried it, she’d licked it tentatively, stroked it a bit, and made gagging sounds before she’d even had it halfway in her mouth.  It was annoying to the point of not being worth the bother.

Tiffany drank her wine and then flicked her lips over her full red lips.  Oh god, the thought of those lips on my cock…  Shit, I got hard easy these days.  I probably should limit my time with Tiffany.

“Oh yes.  I love to give head,” she admitted.  “I kind of miss it.”  She giggled.  “It’s a rush, having that kind of power over a man, knowing you’ve got the center of his being in your mouth and hands.  And listening to those noises they make when they get more and more out of control…”

I was hard as a rock now, and couldn’t stop my next words.  “Do you swallow?”

She arched a brow.  “Of course.  What sort of wimp do you take me for?”

“Dessert?” I asked hoarsely and blindly picked up the menu, knowing I didn’t dare stand until the blood crawled back to my brain and left my overexcited dick.

A week later, Tiffany marched into my cubicle.  She looked like a girl with a mission.

“The Vikings are playing the Lions this weekend, aren’t they?” she asked.  I smiled at her, a bit surprised, because she rarely talked football with me.  She didn’t seem to know much about the game.

“Yeah.  It should be a close game, but I think the Vikings will take them.”

“Well, the Lions are my favorite team,” she said.

I chuckled.  “Why?  Because blue is your favorite color?”

She didn’t laugh, and I realized she had some agenda with this conversation.  “I want to make a bet with you,” she said.

I perked up at the word “bet.”  I ran the office football pool and wondered if she liked the Lions enough to want in on the action.  She sat down and pulled her chair close to mine.

“Here’s the deal,” she said.  “If the Lions win on Sunday, you have to show me your sales tricks.  I get to sit with you all day while you call real customers, and I get to take notes.”

My eyes narrowed.  She was a determined little thing.

“And if the Vikings win?” I asked.

She blushed slightly.  “If the Vikings win, I’ll give you a blow job that will melt your brain.  You told me your wife won’t do it, and it’s just a BJ, so it won’t be like we’re cheating or anything…”

My brain nearly melted at the mere thought of it.

“Do you want a point spread?” I asked lightly.

“Don’t give me your sports odds mumbo-jumbo.  Do we have a bet or not?”

We shook hands solemnly and my mind began to race with excitement.  I knew the Vikings would win.  The Vikings had a better defense, plus the Lions’ quarterback had injured his ankle in the last game.  This bet was in the bag.

I tried to contain my excitement on Monday morning when Tiffany entered the cubicle.  She glowered at me.

“26 to 17,” I said simply.  She sneered.

“Stupid Lions.”

“Gonna switch teams, now?” I asked and laughed.

“Yes.”  She  sighed.  “Don’t worry, I’ll pay up.  After work… where?”

“How about that storage room by Barker’s office?” I suggested.

“Okay.”  She looked dejected.

“Hey… if it really melts my brain… I might show you some sales tricks.”

Tiffany perked up immediately.  “Really?”

I nodded, feeling a little guilty for not showing her anything useful before this.  She really was a great girl.

She showed me just how great at 5:30 that evening.  I had been waiting in the storage room for nearly 20 minutes, feeling like an idiot for not giving her a specific time, and wondering if she would really show.  She grinned at me when she slipped into the door and pressed the push lock on the door handle.

I was already hard, and had been most of the day, truth be told.

“Let’s see the merchandise,” Tiffany said casually.  I unzipped my slacks and pushed them down.  Tiffany moved forward and unbuttoned the bottom buttons of my shirt, to fully expose my jutting cock.  Without further comment, she dropped to her knees.

She slid her cheek gently along the length of it, as if feeling the softness against her skin.  Her fingers touched it gently, and then she gripped the base in one hand, squeezing hard.  I sucked in a breath, and couldn’t manage to expel it when her mouth slid over the head and plunged downward, enveloping it to her fingers.  She twisted her hand as her mouth moved upward, and her tongue splayed along the base.  At the top, the tip of her tongue dove into the slit and flicked in and out.  I cried out hoarsely at the sensation.

Her hand was still twisting the base in a smooth rhythm and her mouth drew downward again.  Her hand fell away as her lips descended, farther and farther until I swore my cock touched the back of her throat.  Her head moved up and down several times, deepthroating with every stroke, and sucking hard on every trip to the top.  Tiffany paused a number of times to swirl her tongue around the head as though she licked an ice cream cone.

I moaned in near-agony when one of her hands reached up and cradled my balls gently, tugging at them on a downstroke that made me want to ram into her, fucking her mouth blissfully.  She prevented that by firmly holding me in place with a hand to my hip—pressing me back against the shelves of the room.  The other hand still fondled my testicles in time with her moving mouth.  The pace of her strokes increased with the harsh sound of my breathing.  God, oh god, nothing could ever be better than this!

I came like a rocket leaving the launch pad and shot my load straight into her throat.  Not only did she swallow every drop, but she sucked my twitching cock dry and licked it up and down as though it were something precious, before tucking it back into my shorts and tugging my pants up.  As she zipped the zipper, she stood and looked at me smugly.

“Well?  How was that?” she asked.

“Can’t talk.  Brain melted,” I replied unsteadily.

Tiffany laughed happily.  “Well, thank you for showing me some of your sales tips today.  Maybe we can work out some sort of trade arrangement.”

Fuck, for a blow job like that, I’d probably trade away my job.  Tiffany might have lost the bet, but she would win in the long run.


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