The Bet

It was not often the bartender saw a woman as beautiful as her. When she slipped into the hotel's bar, virtually every head in the room turned.

She was dressed in a short, yet tasteful black dress, a small leather clutch in one hand. Her legs were perfectly shaped, and met with her hips, dipped into her waist for a shapely hourglass figure.

Her cleavage was well formed, with what looked like large, but not huge breasts that moved with her gracefully. Her long, crimson locks draped down with their luxurious soft curls to about her mid-back.

Her heels clicked politely as she walked, and she went down to the quiet end of the bar, away from the television screens blaring the Mariners game, and eased onto a barstool, her eyes playing up to the CNN broadcast.

The bartender was standing at the opposite side, having just filled a scotch order from a short, heavy-set, nearly bald man who had introduced himself as Henry, an insurance salesman from Hoboken, New Jersey in town for the convention.

"Who's that?" Henry asked, breathlessly.

"I have no idea," the bartender said.

"She's beautiful," Henry said, staring.

"Yeah and defiantly out of your league," the bartender said.

"Hey," Henry said, nearly squalling.

"Look dude, I see it all the time. Pretty girl comes in, she soaks you for some drinks, plays with your head, and then she goes to powder her nose. Save yourself the heartache. Save your wife the heartache too." He said.

"How do you know I'm married?" He asked.

"You may have taken the ring off, but you've still got the mark from it on your hand. I see it, she'll see it."

Howard glared at him.

"Hey, fine, whatever man. I'm just trying to save you some grief."

"Whatever," Henry said, and ordered another double scotch.

The bartender brought it to him, and then chided himself. He certainly killed Henry's tip, but he wanted a crack at the redhead for himself. Softly, he slid a napkin in front of her, and gave her his winning smile.

"What can I get for you, miss?" He inquired.

She smiled at him, with well-formed, crimson lips that shined softly.

"Traditional Martini," She said her voice throaty and breathy. She looked him straight in the eyes and batted her long, thick eyelashes at him.

"Coming right up," He said, smiling back.

Yes indeed, tonight would be his lucky night. He could keep her going with drinks, maybe get off early, and take her home. It was a Thursday and only a couple of the regulars were in. They wouldn't care if he closed about ten. He could get her back to his studio and peel that little black dress right off.

He juggled the bottles with a flourish and rolled the Martini Mixer in his hands, giving her a spectacular performance. He knew she was watching her, out of the corner of his eye, they always did.

Henry the insurance salesman glared at the performance.

The Martini was delivered to her with nary a drop spilled and she smiled by turning up the corner of one of her lips. Her left hand was in her lap and she sipped softly at it, holding the bowl of the glass in her perfectly chiseled acrylic nails.

He hovered over her for just that extra amount time to make sure that she was enjoying her drink.

She looked at him sexily as the mixture of alcohols entered her mouth. She sipped petitely and made a soft slurping noise as the glass pulled away from her lips.

"Is that okay?" He asked in his home-down, folksy manner.

"Just fine, sugar," she replied, again in the breathy tone.

He smiled back at her, thinking to himself that yes indeed, that he was going to get lucky. He wandered back to Henry who had nearly finished the scotch.

Henry just beckoned his fingers at him and pointed to the scotch.

"'Nother double?" He asked, with a smug look on his face.

"Yeah, yeah." Henry said. He tried to straighten out his rumpled shirt and squared his tie some. The bartender brought him scotch and a bowl of popcorn as a consolation prize.

Henry the insurance man grunted at him, and muttered something, drinking at the scotch.

"What's that, Henry old boy?" The Bartender said.

"Send her a drink," He said.

The bartender snickered and said, "Hey it's your nickel."

With no flourish, no razzle, nor dazzle, he presented her the second drink saying, "It's from that guy down there."

She arched a brow at him, and then looked in the bar mirror to try to say who she was talking about.

"You mean the guy by the entrance, next to the pool table?" She asked.

"No, the guy down the end of the bar." She tilted her head and saw a man standing at the bar's rail waiting to be served.

"Him? In the blue shirt?" She whispered.

"No, farther down. The insurance salesman." The bartender said flatly.

Her mouth opened partially, to make the letter, 'o'. The bartender shivered slightly, imagining those lips wrapped around his cock.

She tilted her head a bit more, to meet Henry's eyes.

Henry would be the first one to admit, he was nothing special. He was middle aged, had sold insurance for all of his professional life, alternated between having a horseshoe and shaving himself bald. His wife had to pick out his clothing and match it, for he was helpless when it came to colors and cloth. His kids always gave him ties and cologne for Father's Day and Christmas, as he was incapable of purchasing these things for himself.

Yet, he had a certain charm he would like to think.

She looked at the bartender, and bit on those beautiful red pouty lips.

"I suppose I should send him something back, huh?" She looked at him with her cool, emerald eyes.

"Well I wouldn't. You'd only encourage him."

"Do you know his name?" She asked.

"His name is Henry; he's an insurance salesman from Jersey in town on a convention."

She looked at the bartender, clearly curious.

"Hey, I'm the bartender, people tell me stuff," he said.

"Hm," she grunted softly.

"Yeah well, I tried to warn him. Didn't want you to break his heart and all that." He said.

She eyed him in a friendly manner and replied, "Well be nice to him then. Don't need to be mean."

"Miss, I'm serious, this guy will be all over you."

"Well let him cool for a bit, then." She said.

When the bartender turned to serve the man in the middle, it blocked Henry's view of the Crimson-haired goddess, but it made no difference, her delicate white face was etched into his memory forever.

For her part, the redhead swiftly consumed the remainder of her first martini and started to work on the one Henry had sent her. When the bartender moved, he could see this, and smiled. He beckoned the bartender over.

"See?" He said.

"Look dude, I'm here to tell you this is just not cool."

"Who are you to say, huh bud? I'll make you a little bet." Henry said, full of himself, the scotch putting him in a proud, defiant mode.

Henry pulled out his wallet and folded a crisp, new fifty-dollar bill on the counter.

"Fifty bucks says that I'll put her panties on the bar." He said.

The bartender looked at him coolly.

"You're serious."

"There it is. Fifty bucks. You've got that running around in tips, I know." Henry said. His fat forehead was sweating, and the bartender could see he was getting a bit riled up.

"Alright Henry, you're on. I'm closing at ten-thirty, sharp." He pulled out a shot glass, peeled a fifty out of his own wallet, jammed it and Henry's into it, and tucked it under the bar just out of reach.

Henry offered his sweaty, beefy hand.

The bartender shook it.

The crimson haired goddess went to the bathroom, came back, and found a third drink. The bartender explained it was yet again from Henry.

She looked at the bartender, "well I just can't ignore that. Send him something. What does he drink?"

"Scotch," He said.

She made a face and said, "Paint thinner. Send him one anyway."

Henry smiled as the liquid courage flowed his way. He lifted the drink to give her a cheer from a distance.

The bartender frowned at him.

"Look, Henry, she's just trying to be nice," he said.

"Yeah, and I appreciate it. In fact, I think I'll go and have a little chat."

With that, he picked up his rumpled coat, laid it over his arm, grabbed his drink, nearly spilling it, and headed her way. He clambered onto the barstool next to her, and offered his hand:

"Hi, miss. I'm Henry Peterson."

"Well Henry Peterson, I'm Michele." She replied at him, cool, yet polite.

The bartender wondered if he could get Henry drunk enough to make a fool of him and still make himself out to be the hero. Yes, indeed, that was the ticket. Nothing like being the hero.

He brought them another round.

Henry thanked him, and she looked at the pile of glasses and put her hand up, cutting herself off.

"So Henry, what brings you to the Rose City?" She asked.

"Insurance convention," he said. He launched into a long, utterly boring, and completely trite discussion about term versus whole life.

She listened politely and nodded at appropriate points.

The bartender took it all and then thought to himself that this would be the easiest fifty bucks he ever made and he'd get laid to boot. It was a good life.

As Henry talked, mostly about New Jersey winters and the traffic on the turnpike, one of the restaurant servers came in bearing a platter of hot food and laid it in front of another patron.

Henry's stomach grumbled and he suggested he buy dinner.

"Oh, no, Henry, I wouldn't want to impose upon you," she said, loud enough for the Bartender to hear.

Henry insisted and had menus brought. They migrated to a corner table, and she got giddy half way through the third martini.

The bartender watched them both, growling. Fortunately, the bet was for her panties to get onto the bar, not for him to get her into his room. Over dessert, he softly started to rub at her hand with his pudgy fingers and she giggled like a schoolgirl.

Henry made his move.

He whispered softly into her ear.

She turned crimson, to match her hair and nearly shrieked with laughter. At this point, the bartender had realized he wasn't the one that was getting laid.

He watched her squirm as Henry discreetly tickled at her hips, and her breasts jiggled invitingly.

She leaned over, kissed him on the nose, and scooted down to the ladies' powder room.

Henry smirked at the bartender.

And waited.

And waited.

And waited.

The bartender was the one smirking at Henry, and then was shocked as she returned. She had touched up her hair, and went from being the giggle girl, to the crimson-haired goddess that yet again turned the head of every man when she came through the doorway.

She walked seductively, purposefully, with intent, desire, and hunger to Henry.

She slid into the booth and pushed the side of her bosom against him.

Henry whispered something into her ear, and then she nodded, giggling softly.

The bartender could not believe this.

Henry fished for his room card-key and walked up to the bar and said, "I'd like to pay please."

He flashed the black satin panties she had peeled off in the restroom.

"Damn," The bartender said, and slipped him the fifties.

Henry and Michelle made their way into the exterior glass elevator. Michele was more than slightly drunk, and felt the salesman's shaking, beefy fingers on her petite ass. He knelt down, had her bend over slightly, and reached up with his mouth.

Softly, Henry's dexterous tongue began to probe her needful folds. She wasn't overly wet, but certainly produced the pheromones that drove his lust farther.

He lapped at her from behind, even softly nuzzling her tart ass, and when the bell rung, both squirmed to upright, decent positions as someone else entered the car.

Henry got her to her room and she smirked at him with a sly, knowing look.

Henry did not bother to turn the lights on, and once she'd crossed the threshold, closed, locked, and bolted the door. He picked her up bodily which made her giggle even more.

Tenderly he laid her on the bed, and lifted up the dress, her pubic hair neatly trimmed into an inviting triangle.

His hot breath along was enough to make her squirm, and he took his sweet time, softly kissing her inner thighs on both sides, before running his tongue up the length of her blood engorged mons.

She gasped as the tip of his tongue met with the side of her clitoral hood, gently lapping at it, and causing her to go from squirming to moaning.

With her juices flowing freely, his tongue became more insistent and flicked deeply into her wetness. She writhed and began to gasp.

Like a hunter and its prey, he knew that she was close and he stood, and unbuckled his belt.

His stiff, uncut phallus poked out from his middle-aged tummy, seven inches of uncircumcised manhood that he teasingly rubbed against her labia.

She wiggled her butt against the bed and he loomed over her, the head of his tool softly pressing against her clit. With little care, he slipped the straps form her shoulders and exposed her creamy white breasts with their perky sharp nipples.

Henry mounted her grabbing both nipples at once, thrusting in her in a single, powerful shove of his manhood.

Her head arched back against her bed as best it could and her breasts pressed into his fingers as if they had a life of their own. She pressed back against him with her hidden muscles, feeling his tool invade her.

He pumped solidly, his sweat permeating the room, mixing with her musk and creating the scent of mating throughout the room.

They fucked hard, her clawed fingers digging into the comforters, his balls slapping at her ass. His hands twisted her nipples and her ankles locked behind his back.

She writhed, she moaned and Michelle climaxed powerfully, screaming like a wild animal.

Henry was no better, for the throbbing of her thick vaginal muscles finished him off, and his semen fired a huge, thick load into her wanting body.

She gasped for air, and looked at him dreamily.

He smiled and rested for a few moments, and then softly filled her over, unzipped her, and stripped her nude. He then discarded his own clothing, and pulled the comforter and sheets back for her.

She kissed him on the cheek.

He grabbed at the nightstand for his wedding ring.

"I'd better not loose this," he said, "My wife would kill me."

She looked up at him, her breasts inviting him for round two.

"You're right," she replied. "I would."