Betting People: Casanova

Betting People: Casanova

By Maximillian Excaliber

Introduction

This is a collection of erotic stories about people who find themselves in some rather unique wagers. The plots are straight forward and intended to get you asking yourself, "I wonder if this could ever really happened?" No matter how you answer that question, just try to imagine that in some universe somewhere it did and I think you'll find them enjoyable.

Max

Chapter One -- "Fugly"

"I still don't understand what she sees in him." Kimberly Long said to David Blackfoot. She was walking through the front door of her small, two bed-room house when she'd said it.

They lived together in her Early Twenty-Century style home. It was located in one of the lower-middle income areas of the city of Columbus Georgia.

David was Kimberly's boarder and had been living there for almost two years. He'd moved in with her when the lease at his old apartment expired. When his landlord raised the rent, she'd offered to let him rent a room from him until he could another place to stay.

They had worked together for three years as security guards for a private security firm and she felt that she knew him well enough at the time to trust him. Six months later, when her judgment proved correct, she invited him to stay as long as he liked.

David accepted immediately.

When working, their relationship was strictly professional; when not, it was one of platonic friendship. But lately, even though they got along well together, both secretly felt there was something odd going on in their relationship. Although, neither of them knew exactly what it was, neither was comfortable enough to talk to the other about it.

One night late in September Kimberly and David were returning home from the wedding of a couple of mutual friends of theirs.

The bride was a gorgeous red-head in her middle thirties; and the groom was a homely, almost ugly looking, man in his late forties. She was six feet tall and had the hour-glass figure of a Playboy Bunny. He was five foot nine and had the physique of an accountant... no muscles and a small pot belly. As a couple, they were hard to imagine.

The newlyweds had chosen to break with convention and have a themed wedding. The theme they chose was 'Contemporary Mardi Gras'. Everyone attending was required to dress as though they were going out for a night of fun and frolicking at the annual New Orleans festival.

David was attired in a black pirate costume he had rented from a local party supply store. To his amazement, Kimberly had gone to the wedding dressed more provocatively than he'd ever seen her before. She was wearing a sheer, nearly see-through, white blouse and emerald green mini-skirt, matching green fish-net stocking sand green Go-Go boots. The fact her nipples were visible through her blouse advertised that she wasn't wearing a bra.

David had been even more amazed when, upon arrival at the wedding, he discovered that Kimberly's ensemble was actually quite tame in comparison to those worn by the other women there.

When they returned home, as soon as he got in the door, David turned around and locked it behind him. He'd done so just in time to see her bend down and take her shoes off. Kimberly was standing in front of the shortest part of the three-piece sectional in the center of her living-room. Self-consciously, he became aware that he was staring at here and tried to remember what it was she'd last said. After a few tense moments, it came to him. "Did you ever think that he might be great in bed?"

"In what universe?" Clearly she didn't believe him.

He sat on the other end of the couch and told her, "You said it yourself, he's 'fugly'. So, either he's a great conversationalist, which we both know he isn't, or he's fantastic in the sack. What else can it be?" The implication was obvious for they both knew that the word 'fugly', was slang for 'fucking ugly'.

"Money?" She suggested.

He countered, "No, I did both their tax returns last year; she makes double what he does."

"Then what is it?"

Without a second's hesitation, David answered, "My guess is he has a silver tongue." It was a subtle reference to the groom's skills at performing cunnilingus.

"Didn't you say he isn't a great conversationalist?" Kimberly looked confused. Obviously, she didn't get the reference.

Realizing that she wasn't following him, David told her, "That's not what I was talking about."

"Then what are you..." She started to ask. Her expression changed and her eyes widened knowingly. "Oh, I see!" She considered it, then added, "Nobody can be that good."

David said, "You're wrong." And then muttered under his voice, "Some of us are."

"Us?" She heard him! Before he had time to think of something to say, she asked, "What do you mean us? Are you trying to tell me that..."

He said to Kimberly, "Honey, I can have a woman begging for it so fast it makes her head spin!"

Kimberly jumped to her feet and turned as if she were leaving the room.

Unsure what was happening, David asked, "Hey, where are you going?"

"I'll call you from my bedroom."

Confused, he asked, "Why?"

"Because this one's getting too small!" Kimberly answered with a straight face.

Confused, David asked her to explain, "Too small?"

"That's right! There's not enough room in here for you, me and all that bullshit you're spreading!"

What Kimberly didn't know was that David was in love with her. He had been for the past two years and, wanting her, had stopped dating other women.

The problem was that Kimberly, majorly overly confident in her own perceptions of people, had seriously misjudged him. She had perceived his not dating as a lack of self-confidence, which it wasn't.

He'd tried repeatedly to tell her that he had no such problem but, she stubbornly refuse to believe him.

In fact, he'd been asked out several times and had declined every offer.

So it was that, when he said to her, "I'm telling the truth." he knew with certainty that she wouldn't believe him.

"Dream on Casanova!"

It hurt his pride. "You don't believe me?"

"Hell no! Besides, I don't find you that attractive." She told David, causing him to think to himself, 'She just admitted she finds me attractive!'

To Kimberly, her words had made her sound vain and hurtful. She regretted saying them as soon as they left her mouth.

Confidently, David insisted, "It's not about looks Honey. It's about raw, hair pulling, sheet grabbing, erotic sex."

"Says the man who hasn't had a date since in two years ago."

What David said was, "Did it ever occur to you that might be by choice and not lack of offers?"

"Offers? Are you trying to tell me you've had women asking you out?" She sounded disbelieving. "Are you off your medication again? Don't make me have a couple of the boys come over here and hold you down again."

It was another poor attempt at humor, to which David responded, "You wouldn't be making jokes if you knew what you've been missing!"

"Fine then, show me?"

Since to her, talking to him was about as useful as beating a dead horse, she wanted to end the conversation. Kimberly had decided to bluff in the hopes that she might finally get through to him.

He played her words back in his head again... twice! Even after doing so the second time, he still wasn't sure he'd heard her right. "What did you say?"

"I'll tell you what, I'll bet my extra copy of 'Please, Please, Help Me' against your mint condition original 'That's All Right' that you're wrong."

Now at this point it's important to know that collecting vinyl records was a hobby they both shared and, that the prize of David's collection was a 45 rpm recording of the song "That's All Right" by Elvis Presley. The record was in mint condition and had an appraised value of $10,000.

From the moment she found out he had it, Kimberly had been trying to buy or barter it away from him, which was also about as long as they'd known each other. She'd even tried to get him to wager it in their weekly poker game!

Her most recent attempt had been two weeks prior when she'd offered him one of her two 'mint condition' copies of The Beatles 'Please, Please, Help Me' and $5,000 cash. It was, for the most part, a fair deal as 'Please, Please, Help Me' was selling for about $5,750 on the collector's market and the total value of what she was willing to trade was $10,750. It hadn't been enough incentive for him and he'd turned her down. The Elvis record was, after all, his most prized possession.

He was astonished, first because of what she wanted to wager for and second because of what she wanted to wager on. "Is that your idea of a better offer?"

"I'm totally serious. If you're really everything you say you're are, you've got nothing to lose!"

He told her bluntly, "I have more to lose than you do. Besides, how do I know you won't change your mind as soon as you think I winning and try to call off the bet?"

Kimberly was confident that David would never accept the wager. Since she usually won when they played poker, Kimberly was as sure of her ability to tell when he was bluffing as she was her own to out-bluff him.

'Besides, she thought to herself, he loves that record too much to risk loosing it'.

"Follow me!" Kimberly turned back around and, without saying another word, started walking intently down the hallway.

David stood there alone listening to the click-clack sound of her heels as she walked and tried to decide what to do. About three seconds later, curiosity got the best of him and he took off after her.

By the time he caught up with her, Kimberly was standing in front of the dresser. It was on the left side of her room.

Atop the dresser was her gun-belt. On the gun-belt was a stun gun, a can of pepper spray, a collapsible baton and a pair of handcuffs.

With only the eerie sound of her breathing echoing in the room, Kimberly removed the handcuffs from her gun-belt then, unceremoniously, threw herself onto her bed.

Unaware of her intentions, he asked, "What are you doing?"

"We're going to settle this once and for all!"

Chapter Two -- "Be My Guest"

Kimberly's bed was off-white in color. Both the head-board and foot-board were made entirely of metal. Each one was simple in construct being comprised of two tall, heavy duty, vertical post to act as legs that were held in place by two longer horizontal posts. Think of a long rectangle frame whose sides were legs.

To provide support for the frame, the inside of the box was filled from one end to the other by several smaller vertical metal bars. The bars were spaced about six inches apart.

Kimberly kicked off her shoes and then climbed on hands and knees towards the head-board. After positioning herself so that she was laying in the center of her bed with her head on a pillow.

'Click!' She'd locked one end of the handcuffs around her right wrist and placed both hands above her head and between two of the metal post. Kimberly wrapped the other end of the handcuff around the center most vertical metal bar and then there was a second 'click'.

"There! You see? Now, even if I wanted to, there's no way I could go anywhere." She illustrated what she was saying by pulling hard against the handcuffs.

"Either take the bet or hand me the key!" She challenged as she continued struggling against the handcuffs.

About the same time it became clear to to Kimberly that her efforts to escape were useless, the reality of what she had done hit.

'What if he goes for it?' Until that very moment, the thought had actually never entered her mind.

Kimberly couldn't decide if 'it' she'd been thinking about was her or the 'record'? She tried hard not to think about the fact that they were one in the same.

For several intolerably long, agonizing moments the room was silent as David stood there studying the situation.

He surprised her by asking, "What would you say if I told you I'm considering your offer?"

"I'd say you're in denial." She told him boldly.

Doubt in his mind, he asked, "You really don't think I'll do it do you?"

"No, I don't."

David couldn't decide if she were that confident that he wouldn't take the bet or had some other motive for what she was doing. He could think of only one way to find out. "Suppose I took off my clothes, then would you be convinced I've been telling you the truth?"

"You won't." At least that's what she said.

Offhandedly, he said to her, "Hold that thought. I'll be right back."

"Hey, wait a minute!" She called to him, "The least you could do is hand me the keys to the handcuffs before you leave!"

He smiled coyly and replied, "Oh, don't worry. I'll be right back. I'm just going to go brush my teeth and gargle with mouth wash before we get started. I want to make sure I have minty fresh breath when the time comes."

'You're just stalling! You can't fool me with that poker face of yours. Why I'll bet your next move will be to try and bluff me by stripping down to your underpants.' was what went through Kimberly's mind as he left the room.

Inwardly she smiled, for when he returned about two minutes later, he was indeed down to his shorts.

As he reentered the room, David asked, "Convinced yet?"

More confident than ever, Kimberly replied...

"What are you going to do next, take off my panties?" Kimberly said as she thought to herself, 'I know you David. You're going to take this right up to the point of no return and quit.'

Rolling his eyes in frustration, David grinned and said as if suddenly inspired, "That's sounds good to me. You don't mind do you?"

"By all means, be my guest." Kimberly said playfully and then raised her hips to make it easier for him.

David bent over her and slid his hands under her skirt.

Kimberly felt the palms of his hands to running sensually over her outer thighs until his fingers found the waistband of her panties. Then, slowly he began just as sensually moving his hands back down, taking her panties with them. She was surprised, not by the fact that he had done it, but more by how arousing his doing it was.

After tossing her panties in the floor, David moved to the end of the bed and sat down.

Almost mockingly, she opened her legs before him.

He shrugged and began climbing face first between them and said, "Raise up again so I can take your skirt off. It's in the way and I don't want to have to keep moving it."

Kimberly giggled and complied.

The zipper of her skirt went down and he took it off her. Kimberly promptly lowered her hips but left her knees bent and her feet flat on the bed.

That's when Kimberly's got her first surprise. David threw the dress over her face, leaving her in near darkness. It startled her for a moment and for a second she thought he might actually go through with it. It was a fleeting thought though and was soon replaced by another idea.

"Well Casanova," Kimberly giggled, "do we have a bet or not?" What she was thinking was, 'He just did that so he won't have to look me in the eyes when he tells me no!'

But he said nothing. Instead, what followed was the sound of movement and the shifting of weight on the bed between her legs. Kimberly assumed he had finally given up and was getting off the bed.

'That's odd! It feels like he's moving closer, not farther.' Kimberly wondered to herself.

Something brushed up against the underside of her thighs. That was followed by movement to her sides; but she couldn't make out what it was.

'What is he doing?' She asked herself as her heart began racing with excitement.

It wasn't until his hands reached under the bottom hem of blouse and cupped her breasts firmly that Kimberly finally realized what was happening.

Chapter Three -- "You've Got A Bet"

"Okay! You've made your..." She gasped; she could feel his hot breath breathing on her womanhood. Unexpectedly, something soft and moist, she didn't know what, touched her clitoris. There was the unmistakeable sensation of David blowing gently on it and, almost immediately, her clit began tingling strangely. It was the oddest feeling she'd ever had, both warm and cool at the same time.

Any doubt she had to what was going to happen next disappeared as soon she heard him say, "You're right Kim!" and then felt what Kimberly knew had to be his tongue trace a path from bottom to top, through the furrow of her womanhood.

He went on, "I think it is time we settle this once and for all." His tongue did it again and then he informed her, "You've got a bet!"

Without waiting for her response, David began repeatedly rolling his tongue around and around her clit. He did so with all the skill of a male escort and it was the last thing Kimberly expected and left her all but speechless!

'Why is my clit tingling like that?' Kimberly asked herself when she became aware that her pussy was becoming wet with her own juices. 'It's never done that before!'

While she lay there trying to figure out what was happening to her, David, who was giving her clitoris a tongue lashing, began kneading her breasts. She felt David's fingers lightly pull at Kimberly's nipples until they were hard and erect as he had become, though she didn't know that at the time.

When he tasted her juices begin to flow, David removed his left hand from her right breast.

Kimberly wondered out loud...

"David, what are you..."

Then something penetrated her and she had her answer.

From what she could tell, it was about three inches long, about as thick as a cigar, rigid yet flexible in some places, and fleshy. Wet as she was, it had entered her without even the slightest resistance and when it started moving inside her, Kimberly assumed that it was one of the fingers from the hand he just taken off her breast.

It was a good guess for entering her was, indeed, the index finger of David's left hand.

While she lay there tying to imagine what it looked like, David gently pushed his finger upwards and began probing gently until he located the rough and rigid patch of flesh inside her.

Kimberly's body jerked in response for he had found an erogenous zone she had not known, till then at least, existed and, quite to her surprise, was a very sensitive one.

"Oew!" She cried out when the first digit of David's index finger began rubbing back and forth over her g-spot while, at the same time, he used the fingers of his right hand to gently pull upwards on her left nipple as he began rolling his tongue repeatedly around her clit as if he were licking the cherry atop an ice-cream cone.

Kimberly's tender nipples were alternately being manipulated into excitement as her already swollen clit became even more inflamed and more sensitive by the manipulations of his tongue. Her whole body began quivering, held irresistibly in a prolonged state in which jolt after jolt of erotic electricity and, it wasn't long before she became acutely aware that an orgasm of immense proportions would rapidly cease her.

When it was nearly upon her, Kimberly clinched her hands in fists and tensed up suddenly indicating to David that she was at the very brink of orgasm when David did something she didn't expect...

He stopped!

"No! Don't! I was almost there!" Kimberly pleaded with him, then as she fell farther away from the precipice of sexual Nirvana, realized what she'd said.

It was as if her plea fell upon deaf ears for David neither continued, nor said anything in response. Instead, as he continued teasing her left nipple with his hand and just as abruptly removed the finger of his other hand from her pubis, he placed his other hand under Kimberly's blouse and back onto her right breast. Once there, David commenced gently pulling her distended nipples with the genial touch of someone trying to pick a delicate flower.

The air-conditioner came on and the cool rush air rolling over her body gave her goosebumps. When it did, her nipples became even more sensitive than they had been before causing each tiny tug to feel more and more exhilarating than the last.