Don't Bet With Me

Paul hated Sharon. She was the bane of his existence in this office, the person who caused him more trouble than the rest of the company combined. She always thought she was right and was never shy about letting him know. Whenever she had a problem with his team, she came straight to him and complained. Then she would pull at him constantly like a mad dog, until the issue was resolved. Through experience, Paul knew she was wrong a lot more than she was right, but explaining numbers and justifying where they came from could be a time-consuming and painful process, which made every problem Sharon reported torturous. The fact that she was wrong so often did nothing to ease Paul's pain.

Today she stood in front of his desk and complained about a series of errors in a report she was waving at him. She was tall and slim with a figure that she kept hidden in airy business suits with dull colors. Her face, while not at all ugly, was nearly always framed in a stressed and disgruntled look that encouraged everyone to look away, lest they encounter her wrath.

There seemed nothing to Sharon but her job and Paul was not interested in finding out if that was indeed the case. He saw her from behind one day when they were having an office move. She wore tight jeans that showed off her attractive rear and her flowing brown hair was loose around her shoulders, rather than tied up and pulled away from her face. For a few seconds Paul wondered who the attractive new addition to staff was... a few seconds that were promptly forgotten when he saw who the figure actually belonged to.

"There have been at least twelve errors reported with this in the last month." Sharon barked at him. There was a seat in front of his desk she could've taken, but she chose to stand and look down at him.

"You're exaggerating again." Paul shook his head and sighed, this was entirely normal for her. ""There can't have been more than three."

"Bet you anything you like there are more than ten." She was defiant. "I placed calls on every one of them. Check your system."

"Bet you anything you like there are less than five." Paul just wanted to be rid of her. "Name your bet." He started to tap at his keyboard to check.

"You can buy me dinner."

The words hung out in the air for several seconds while Paul typed. He didn't comprehend them at first, but as they seeped through his brain he looked up at her in amazement. "That's a no-win bet for me." His brow furrowed and he exhaled. "Whatever." He already intended this bet to be one he didn't collect on when he won it.

His own system betrayed him. He looked at the list on the screen, counting the lines with a growing dread. "Fourteen."

"You owe me dinner." Sharon smirked, already leaving the office as though she sensed he might throw something at her. "And Paul, get those errors fixed, will you?"

*****

He thought she had forgotten. He wanted to forget, but the awful prospect of sitting across the dinner table from Sharon haunted him. After a couple of months without a mention of the bet Paul was feeling at least a little better about it. Mmaybe Sharon really had let it slip from her mind? He should have known though—she never forgot anything.

In the end, she called in the bet when they were at a week-long offsite strategy session. They were representing their division at the session, held at a hotel downtown. The schedule was punishing, long days, pre-arranged dinner and bed. For three days Paul hadn't been outside the hotel.

"Thank God that day's over." Paul closed his notebook and sighed.

"You joining us tonight Paul?" A colleague from the West Coast asked.

"Not tonight." He rubbed his tired face with his hands. "I can't face hotel food again, and I'm worn out from all the shop-talk. Thought I might just take a walk and have an early night,"

As the others wandered off Paul packed away his laptop and papers and sensed the arrival of someone else at his side. "If you're not eating in the hotel tonight I guess that means you could buy me the dinner you owe me."

He looked up to see a familiar smirk on Sharon's face. His mind spun with reasons to get out of it, but in the end he reasoned that he might as well get it over with. After all, at least he could put dinner tonight down to a business expense, sweetening the prospect just a little. He responded, "Sure." trying not to sound as grudging as the concession was.

*****

It surprised him when she chose only a moderately expensive Italian restaurant as he was sure it was her intention to extract every ounce of pain she could from the evening. They walked from the hotel and talked a little about the content of the week's meetings.

"No more business, okay?" Sharon insisted as she raised her wine glass to her lips for the first time. "I think we could both use an hour or two off this week."

Paul wasn't about to disagree with that sentiment. He tried hard to keep the conversation going but that was a tough task considering how much he disliked Sharon. As she talked, he did take a few moments to notice her casual appearance—her hair down and features softer than they were in the office. It wasn't like she was unattractive. She just had an annoying habit of rubbing people up the wrong way with her abrasive manner.

As she told him about her last vacation to Aruba, Paul found himself not really listening, but watching her lips move sensuously, exposing her teeth as she smiled. He noticed that she had boobs for the first time. They weren't large by any means, but they did look inviting as they pressed against her shirt. He thought back to the day she had been in the office wearing jeans and wondered why he hadn't noticed more good things about her before now.

Sharon's voice was softer than he was used to as she described some of the books she'd read on the beach, the sunset photographs she'd taken and how she'd learned to scuba dive. It was something he'd never seen in her before now, and helped him start to actually enjoy the evening.

"So," Sharon smiled knowingly at Paul, "how bad has losing your bet with me been?"

Dabbing his lips with his napkin, Paul smiled back sheepishly. "Better than I thought it would be." he admitted. "I was afraid you'd spend three hours telling me all the mistakes my team makes all year."

"Everyone makes mistakes." Sharon laughed now. "I just hope you don't think that losing your bet was a big one."

"No, it's been fine. And I'm not used to losing bets." He thought back uncomfortably to the bet he made with her. "Normally I don't make bets without knowing I'll win."

"Me neither." Sharon sniggered, one up on that one. "In fact, I can't remember ever losing a bet."

Paul watched the devilish look in Sharon's eyes. Possibilities raced through his mind, all of them somewhat less risqué if his dinner companion was any other woman but Sharon. "I'll bet you can't refrain from complaining to me for a month." he smirked.

Sharon smiled and shook her head. "I need to accept the bet before I can lose it. And you know I'd never accept that one."

"Well, you can't blame me for trying." Paul smiled, realizing he was actually enjoying the exchange for the first time. "So, what bet would you accept then?"

Sharon paused just for a few seconds as she looked into his face. Her look caught Paul slightly off-guard as this wasn't the look of someone trying to get one over on him, this was the look of someone searching for a bet she knew he couldn't win. She pursed her lips and looked away for a moment before coming back to look straight into his eyes. "I'll bet I can give you the best blowjob you've ever had."

Paul might have choked, but fortunately he had finished eating. Still, he coughed and furrowed his eyebrows like he'd misheard her. "Did you just bet me...?"

"Yep." Sharon was looking quite self-assured, but in a wholly different way from how he was used to seeing her.

Paul almost stuttered over the words, "But to win that bet you would have to..."

"Yep."

He recovered slightly, but was still off-balance as his mind raced. "What makes you think that you'd win, especially as I'd be the judge?"

Sharon took a deeper breath than normal, as if she was heading down a new path for her, the ball was rolling and she was finding her way. "Every boyfriend I've had has commented on it. Apparently it's just something I'm good at."

"And you'd be willing to... let me be the judge?"

"Sure, why not?" Sharon tried to make out that it was no big deal, but there was something in her face she couldn't hide.

Paul caught the look, and realized for the first time that she wanted this, maybe had even planned it all along. As he watched the fire kindle in her glassy blue eyes Paul shook away all of his previous visions of Sharon and looked at her with new eyes. It wasn't so much a surprise as it was an awakening as he recognized her for an attractive, desirable, woman and not the ogre he'd come to despise at work. Down in his pants a familiar stirring began, fueled by Sharon's intent smile and the thought of her slipping his cock between her lips.

Although her offer sounded cold, Paul watched her face intently, knowing that they had both somehow stripped away the veneer of their weekdays and found attraction in an unexpected place. Now he felt excitement and anticipation as his pulse started to race and he tried to find some calm in the moment.

"So," he mused, "just what would the bet be? What would I win or lose, depending on how I judged your skills?"

"I don't know." Her face crossed and Paul realized she hadn't though about it before. "I'll think of something. Maybe... breakfast?"

*****

As they idly walked back to the hotel together the air was heavy enough to keep them from feeling the chill night that was closing in on them. Sharon couldn't quite believe she'd been brave enough to make the bet with Paul. She'd always liked him, despite their work run-ins, but the desire that gripped her as they ate dinner had been quite a surprise. Now she had done something bolder than she could ever recall and was energized and excited by it way beyond her expectations for the evening, or the bold gesture.

Paul's excitement was high also, even though the walk felt a little strange—weren't two people about to become sexual partners at least supposed to be holding hands by now? Their conversation was gentle and light, belying and disguising their proposed imminent activity. Paul had difficulty imagining that they were simply going to enter Sharon's room, her pull it out and go to work. But that was the bet, and as much as he couldn't get the image of her caressing him and looking up at him there was an equal amount of excitement in his not knowing how their movements would play out. He even allowed himself to fantasize about returning the pleasure for her, should that opportunity arise.

"Your place or mine?" Sharon giggled as they got the hotel elevator doors.

Sharon slipped the plastic entry key into her door, waited for the click, pushed it open and led Paul into the room. As he followed her he felt himself slip from excited uncertainty into a nervous state of what-the-hell-do-I-do-now.

"Last chance to back out." Sharon offered, turning to him, still unsure of her own movements and ever more aware of her pounding heart.

"I'm game if you are." Paul said bravely.

"Okay then." Sharon smiled and took a step towards him that looked a lot surer than it felt.

She paused just for a second in front of him before reaching with both hands to pull his shirt out of his jeans. "Shirt will just get in the way." She explained, meeting his eyes and starting to undo the buttons upwards. "I think it's best if there are no clothes getting in the way, don't you?"

Paul nodded and swallowed as she undid the final button and pulled the shirt away. He couldn't help but notice the intensity in her eyes as she looked at him and smiled, knowing the heights his excitement was now reaching. Sharon looked away from his gaze and knelt down and pulled off his shoes and socks. Then she leveled her gaze firmly at his groin as she started to unbuckle his belt. Paul thought he caught her licking her lips but was too fired up with electric anticipation to be sure of anything anymore.

He looked down intensely as she pulled at the leather and loosened the buckle. In a few moments he was going to be exposed in all of his glory to a woman he hated just an hour ago, all so she could win a bet by giving him the best blowjob he'd ever had. The very thought had him twitching beneath his denim.

Sharon pulled at the button on his jeans and eased the zipper down over the considerable bulge that had appeared. She pretended not to notice how hard he was and, smiling to herself, intentionally didn't run her hand over his cock even though by now she craved to see it, feel it. Despite the fire building in her panties she wasn't ready for Paul to know how turned on she was and tried to make her actions seem less passionate than they were. As she pulled away the jeans from his legs Paul stood upright again and her eyes came back to rest on the bulge of his cock, now only constrained by his dark blue briefs.

"Looks like you don't dislike me quite as much as you used to." She smiled up at him.

"I've seen a different side of you tonight." Paul admitted. "I can't believe I missed how sexy you are all this time. I also can't believe we're going to do this. It's quite a turn on"

"It is kind of surreal, isn't it? But, yes, very hot." And with that she deftly pulled his briefs over the top of his erection and down his legs. Right in front of her widened eyes was a beautifully shaped and very erect uncircumcised penis. "Very nice." she whispered. "Good all around, shape, length, girth." She looked up at Paul, smiling. "And you don't mind me playing with it?"

Paul shook his head, her actions reducing his ability to speak.

Sharon continued to survey his cock without touching it, moving her head around and watching it twitch with anticipation, his heartbeat trying to squeeze more blood into it as she gazed hungrily at him. She placed a single finger on the underside and ran it down his length, then around his balls. She whispered throatily, "I don't want you to do anything, but I need you to keep standing. That's the best way, something to do with the blood flow I think. But overall, just relax and enjoy. Don't try and hold back or anything, just go with the flow and let it happen."

He saw a huge smile on her face just before she leaned towards him and kissed the tip of his cock.

Sharon took the weight of his balls in the palm of one hand and used the other to grip his cock firmly at its base. Then she took the head of Paul's cock into her mouth, clamping her lips around the rim and teasing the underside of the head with her tongue, rubbing it back and forward along the sensitive part, just under the tip.

As a start, it was spectacular. Paul couldn't believe the sensations he was getting from all around his groin. His balls loving the weightless attention of her hand, his cock throbbing with the sensations her tongue was delivering and now her thumb was starting to rub along the underside of his shaft. He'd never known quite such a concentrated sexual assault on his body, instant pleasure. He thought about what Sharon had said about holding back and wondered how that would ever be possible if she kept this up.

She obviously knew what she was doing. Just as his balls started to retract, she noticed and stopped the rubbing with her tongue. Pulling her mouth off him she licked at the underside of his shaft and made some long strokes with her hand. Paul felt huge in her hands and mouth, bigger than he'd ever known his own cock. He looked down to watch as she ran her tongue along him again, her smiling eyes letting him know that she had him exactly where she wanted him.

Her hand closed a little tighter around his balls now, squeezing them gently and sending sparks up his shaft. Then she closed her mouth over the head again, clamping him tight and rubbing her tongue back along the underside of the tip. Again, the wave of pleasure built as fast as he'd ever known. This time she added a new movement and swiftly took much more of him into her mouth, dipping down his shaft till the head hit the roof of her mouth and then slowly drawing her lips along him as she got back to working him with her tongue. Paul moaned, as he felt Sharon's grip on his balls loosen and her fingers start to trace tiny movements all around the sensitive skin at the base of his cock. It felt inevitable that he would explode.

Of course, Sharon knew what she was doing, took her mouth off him and slowly stroked him again. This time when she looked up at him and started to lick underneath his cock he saw how much she was enjoying her control over his pleasure. He was in no position to deny it to her, it wasn't just his cock that was being blown... it was his mind.

This time he knew what would happen next. Sharon took the head into her mouth and squeezed his balls. After using her tongue on him for a minute or two, she dipped her head over him again and withdrew slowly, back to tonguing him. This time though her hand started to trace very lightly all over his shaft as his balls tightened inside her other hand. Sharon let them go, but continued the feather-light movements of all ten fingers on his skin. There was no sign of her taking him out of her mouth this time though and he found himself rushing towards the point of no return as she gently eased pressure on and off the rim of his cock with her lips.

The last thing he expected was that she would pull him out of her mouth just before he came, but, just as everything else she did, it was planned and felt incredible when she moved her head to the side of him and let her tongue continue to work the underside of the tip, moving with him as he did and applying only the softest touch to his most sensitive place. Paul could do nothing but groan as he started to climax, his cock twitching like never before as the waves of heat shot through him.

All through his orgasm Sharon was barely touching him, her tongue bouncing on and off his cock as it twitched and her fingers traced lightly over him. The first shot of come was the largest and most powerful he'd ever known. It seemed like it was taking off from the platform of her tongue and shot at least six feet across the room like a white comet, splashing against the dark carpet. As the streams continued Paul could hardly breathe and muttered, "Oh God" over and over again while his come laid an ever decreasing trail back to his jumping cock. The power of his sixth and final spasm was finally reduced to less than a spurt as the last of his load seeped out of him and down to Sharon's tongue.

"Good God, that was amazing." Paul slumped back onto the bed, his legs requiring some rest after their ordeal of keeping him standing through the most intense climax of his life.

"Glad you enjoyed." Sharon climbed on the bed to kneel next to him and look down at him with a now-familiar smirk. "Was it good enough to win my bet?"

"By a long, long, way." Paul laughed, a normal breathing pattern still eluding him.

"So, you'll just be getting dressed and meeting me for breakfast then?" she teased, running a finger a long his still-hard cock. "Which you'll be paying for of course."

"I'll pay, but I'm not so sure about leaving just yet." Paul sat up and reached to pull Sharon to him, kissing her hungrily now. "I'd like to repay you for that wonderful experience, if that's okay with you?"

Sharon's calm broke for the first time as she started to pull her shirt off. "God yes, I'm so hot right now you wouldn't believe it. You have a beautiful cock and I was so turned on making you come."