A Wild Hold'em Game Ch. 02

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I went through the day wondering just what the Hell this little meeting would be like. Despite being positive that it simply wasn't going to happen, I couldn't stop fantasizing about Cindy, even though she is such a bitch. In fact that was probably adding to it, if by some miracle this came to pass I would certainly take her down a peg or two. I'm telling you the woman is a looker, and built like the proverbial 'brick shit house'!

I intentionally arrived about 15 minutes late. I was still furious at Fred over this whole thing, but felt like it had gone far enough. While I planned to make him even more miserable first, I intended to let them off the hook. It was obvious Fred couldn't afford this and while fantasizing about Cindy had been fun, this was tantamount to coercing her into having sex with me, which just isn't my style.

I rang the bell and Cindy answered the door. She really is pretty. If she smiled instead of half scowled all the time, and would go a bit lighter on the makeup, you might even call her beautiful. She looked irritated.

She also looked sexy as Hell. I'd never before seen her dressed quite as she was. She had on a top, that while wasn't very tight, had an extremely low, scooped neckline that showed lots of cleavage and made it clear that her tits were very large indeed. At least a 36 D I guessed, maybe even DD.

Rather unceremoniously and without so much as a 'Hello' she said, "Come in."

She turned and walked away, leaving me to close the door. This did give me an opportunity to watch her fantastic ass, which was encased in a very tight pair of stretch pants showing no visible panty line, sway across the room. Far more sway than the way I'd seen her walk in the past.

"You're late" she added as she walked.

I couldn't figure out what the fuck her appearance and behavior were about. Perhaps she was going to tell me to go to Hell, as I expected, and just wanted me to know what I was missing.

In any case her attitude, which was even more arrogant and snotty than usual, was quickly pissing me off all over. You'd think that facing the choice she had or coming up with seven grand, you'd at least be polite to the person holding the cards, to use an apt expression.

Fred was sitting in a chair nursing a drink and looking very haggard. It appeared he hadn't had much sleep recently. I imagined that Cindy had been ragging on him non-stop since Saturday night. Fred just looked up and grunted "Hi." He didn't get up.

Cindy sat as she picked up a half full wine glass. She looked at me and without much enthusiasm said, "Help yourself if you'd like a drink" gesturing to the bar.

I was starting a slow simmer. The generous mood I'd had when I arrived was quickly evaporating. If these two didn't lose their attitudes soon I intended to make them pay for it. I went to the bar and poured myself some of Fred's expensive scotch. I had to keep repeating in my mind, "Stay cool!, Stay cool!"

I sat down across from them and took a slow sip, then, "So, what do you two want to talk about?"

It instantly became clear that Cindy was going to do the talking, "I'd think that would be obvious!"

Her tone was imperious and I was getting more and more angry.

"Of course it's obvious, I mean SPECIFICALLY what do you want to talk about" I replied, not completely restraining my anger.

"First off, I don't think the note Fred signed is enforceable, and secondly what you are suggesting in lieu of payment is an illegal activity" she said with a sneer.

I was one step from changing my mind completely and making them pay one way or the other, but with the attitude that Cindy was demonstrating, knocking her down a peg or ten was starting to sound pretty damned appealing.

"If you don't think the note is valid, call John and ask him. I think you'd agree he's a highly competent attorney and wouldn't have been a party to this if it were otherwise. As for the legality of the alternative 'payment', I did not suggest it, Fred offered. If there is any illegality here, I think it would be called soliciting. So let's not stand on a lot of formality, or veiled threats, okay!" I said forcefully.

For the first time Cindy seemed to even acknowledge Fred, and with a withering glare. I wondered if he twisted the story so that I'd suggested the sex rather than him.

Frankly, I wasn't sure if she had a valid point or not, but I really did believe that John wouldn't have let us do the note if it was not legal and as for what did, I suppose, border on prostitution, they would certainly be in more legal hot water then me, at least I thought so.

And like in poker, this seemed like a good time for a bluff, "And if all this became an issue, I'd think the press would have a field day. It seems more like to have a negative effect on a married insurance professional that a lowly old beer salesman!"

I could see that hit home.

"Fred, I thought you said that Scott made this offer?" she said coolly.

I could see Fred squirming and before he had a chance to speak I jumped in, "Fred presented an offer, I simply told him it wasn't enough to offset the amount of money at stake. He asked what would be then and I told him what I thought."

If looks could kill, Fred would have been stone dead that instant.

Cindy glared at him and said, "Is that true Fred?"

Fred just nodded his head yes and wouldn't look at either of us.

Cindy turned to face me. Obviously a bit taken aback and not quite so arrogant suddenly.

"So specifically, what would you expect me to do?" she said hesitantly.

"Cindy, first lets be clear. Fred can simply pay me the $7,000 and we'll all be done with this affair" I said reasonably.

I thought she was going to cry, but then she stiffened. Evidently there is quite a bit of mettle in the woman.

"Scott, we simply can't afford that kind of money" she said resignedly.

"You could pay it over time" I said, even more softly,

"Look", I went on, "the original bet was for $3,500. I'll call it even for that!"

"Scott", she said gently, clearly thankful for the fact I was being so reasonable, "we can discuss the alternatives in a bit, but first I'd like to hear exactly what I'd have to do to 'liquidate' this bet."

I couldn't quite figure out what was going on, I'd given them a reasonable out and yet she still wanted to hear details. Well, I was getting soft again, starting to feel sorry for Cindy, and actually Fred too, but I was going to make her pay for the way she'd acted earlier.

"Cindy, I heard Fred tell you the essence of it over the phone, and I can't imagine you haven't grilled him about it ever since. You tell me what you think I expect!" I said.

I could see I'd generated the reaction I'd hoped for. She was actually squirming in her seat and blushing too. This was going to require her to speak using language that was quite foreign to her evidently, and to someone she preferred to think herself as superior to.

I couldn't totally suppress a small grin. I just waited.

She swallowed hard, cleared her throat and started, "Well, uh, you evidently expect a weekend of sex. Starting on Friday and not ending until Sunday."

"Yes. What kind of sex?" I said, warming to how this was going. At least I was getting SOME enjoyment out of this.

I looked over at Fred and as far as I could tell he hadn't moved. He just sat there with his head in his hands.

"Well, uh, intercourse and oral, and uh, mm" she stammered, unable to think of a polite euphemism for what was next "and anal as well."

"What else did Fred tell you?" wondering if he'd mentioned my size as I'd told him, but I was willing to wait until later to find out for sure.

"He said something about 'kinky'. Would you have 'whips and chains' in mind" she said this last with a very nervous little chuckle, trying to dismiss it I supposed.

I thought I was beginning to get an inkling of what she was up to and decided to play along.

As deadpan as I could, I answered, "I've always found chains too clumsy. Ropes and leather are far more practical."

She visibly blanched at that, it was all I could do not to laugh.

"Whips?" she croaked.

"Look Cindy, to make it a bit easier on you, we'll limit any punishment sessions to bare handed, plus the more mundane sex toys like nipple clamps and butt plugs!" I said crassly, wanting to make her us uncomfortable as possible.

"How do I know you won't just make it so hard on me I can't finish and then still want the money?" she said, quite gravely. Indicating that she was actually seriously considering going through with this.

In the most honest and trustworthy manner I have, which is pretty good actually, "Cindy, you'd have to trust me, but I promise, I won't do that. I won't let you be injured in any way and, do you know what a 'safe word' is?"

She blushed a very bright red this time. Damn, the bitch had some kind of S/m experience in her past! She just nodded.

"Well, you'll have one and I promise I will totally honor it! Hell Cindy, you'll probably even enjoy a good part of it!"

"I see" she said with a look of deep concentration on her face.

"Scott, there's one more question I have?" she said.

"Yes?" I replied.

"Fred said you are, um, that you are well endowed?" she asked.

I laughed, "Cindy honey, 'well endowed' doesn't even begin to describe it!"

She tried to hide it, but there was a momentary little twinkle of excitement in her eyes at my response. Now I was almost positive I knew what she was up to. It was time to find out and bring this nuttiness to a head, one way or the other.

"Look guys, I think this has gone far enough. How about if I just agree to tear up the note Fred signed and we all walk away now?" I said sincerely.

For the first time Fred reacted. He looked up and while his mouth hung open in disbelief there was a light in his eyes that had been lacking until that moment. He was about to speak when Cindy cut him off with a look and her own answer.

"I'll not have MY husband called a welsher!" she stated emphatically.

I then was positive why she was serious about going through with this. The asshole had made this bet and she was going to teach him a lesson by making him live with the consequences. I began to think she might actually be hoping to enjoy herself, but had wanted to find out just how much 'kink' was going to be involved before committing.

All the air had gone back out of Fred and his head was in his hands again. I guessed he'd known all along where she was headed.

She took a deep breath and straighten, "Scott, I'll be at your house this Friday at seven!"

"Look guys, I'm not going to say no to a weekend of kinky sex with as sexy a broad as Cindy, but I'm giving you one final opportunity to walk away. If you agree to go through with this, once I walk out the door tonight, either you show up and keep the commitment, or I collect the seven grand. Now, one last time. Are you sure?"

I knew I was taking a big chance by doing this, but the trade off would be of HUGE value.

A pause, another deep breath, then "WE are sure!" she said.

"Okay, see you Friday" and with that I set down my barely touched drink and let myself out.

As I drove home I couldn't help think, "Shit, I wonder if she REALLY is going to do it. If she does, it's going to be a Hell of a weekend!"

I didn't have a lot of important matters to attend to that week. A fair bit of busy work, but nothing requiring serious concentration. It was a good thing, since about the only thing I could think about was Cindy and the coming weekend. My devious mind spent almost every waking hour thinking of torments to inflict and pleasures to extract. I thought about various approaches to the big picture as well. Devising many, then narrowing it to a few and by Friday, finally settling on one. Oh naturally I intended to see that she got some very pleasurable fucking out of it too, but had decided that I'd make her both wait and earn it first. I always like to send a woman away with some unique memories and wanting more.

I'm a believer that a man with a truly large cock, who really knows how to use it, can pretty much spoil a woman for a guy with a regular cock in the future. I intended to do my best to accomplish exactly that. It would be the price Fred would have to pay for being such a total jerk and asshole. If he was willing to let her try some strange stuff, he'd just have to risk the consequences.

I still figured it was 50/50 at best that she'd show. Nevertheless I was all ready when 7:00 rolled around on Friday. 7:00 came and went and just about the time I figured she'd back out after all, the doorbell rang. It was her. It was nearly 7:20, I wondered what that would portend.

"I'm so sorry to be late. The traffic was terrible and it took a lot longer to get here than I thought" she said nervously.

If she was going to leave her attitude at the door, that would be a good thing. I'd be nice too.

"Don't worry about it, Friday's are often like that out this way" I said easily.

She smiled slightly and you could see some of the tension flow out of her. She still appeared pretty uptight. She'd dressed casually, wearing jeans and a casual blouse, but still looking sexy. She probably figured she wouldn't have them on much, which was true.

"I brought a few things" she said indicating a small overnight case she was carrying.

"Come on, I'll show you around" I said taking the bag.

I showed her the guest room and bath and told her to make herself at home in there, intending to let her sleep there alone, the first night. Then I showed her the rest of the place, especially the master bedroom suite. I purposely hadn't left any 'toys' in sight. I didn't want her run out the door before we even got started.

After I showed her around I wanted her to have a few minutes to relax before we started.

"Would you like a glass of wine?" I asked her, "Or something stronger if you like?"

"Wine would be nice. Chardonnay if you have it" she said, clearly happy at the offer.

"I do, make yourself comfortable" I said as I went to pour some and grab myself a beer.

During a serious S/m session I have a strict rule against alcohol, but I had no intent of tonight being anything like that, plus I thought it would do her a lot of good to relax.

When I returned she was sitting on the sofa. I handed her the wine and sat across from her, needing to discuss a few things.

"Cindy, you've done a little S & m before, haven't you?" the way I said it, she knew it wasn't really a question.

She looked a little surprised, but didn't play games, "Yes, how did you know?"

"The way you reacted when I asked you about a 'safe word' on Monday"

"Oh" was all she said.

"Tell me about it" I said.

She hesitated.

"It will be better for you, if I know about your prior experiences. Look, there is something else you need to know, so you can trust me. No matter WHAT happens here this weekend, I won't tell a sole about it. I just don't do that. Not even Fred, what you choose to tell him is up to you."

"What about the other guys from the poker game?" she asked. This was clearly an issue for her.

"Not a word. I do think it's inevitable that they'll know you went through with it, after all they heard Fred call you too, but other than telling John that you did or didn't fulfill the bet so he knows what to do with the note, that's it. They'll just have to guess!" I said ending with a smile.

She smiled too "Well, it was way before I met Fred. A guy I went with in college and I experimented with a little bondage. Nothing heavy really."

"That's it?" I probed.

"A little spanking too, nothing more than that" she said shyly.

"What did you think of the spanking?" I delved deeper.

Even more shyly and looking down, "It was okay."

I decided to let it go at that.

I gave her my standard safe word pair. 'Yellow' for slow down, 'Red' for stop. I explained that if things got too intense for her and she said "Yellow" I'd significantly ease up, but not necessarily stop. If she really needed me to stop altogether she was to say "Red". I told her again I had no intention of hurting her and that I was experienced enough at this that I was positive she wouldn't need her stop word, but assured her if for any reason she did I would stop everything immediately.

Because of the bet, I explained further, there were some caveats so she wouldn't abuse the use of her safe words and just use them to avoid doing something she simply didn't feel like. She could only use "Yellow" a total of three times, then she was out of slow down words, leaving only stop. If she used stop twice, the second time we were through and she would leave, but she and Fred still owed me the money.

She nodded agreement. I thought that was lenient enough to give her some breathing room, but tough enough that she wouldn't use them unless she was truly reaching her limits.

She'd finished her wine.

"Any questions?" I asked her.

"Well, mmm" she paused.

"Go ahead, it's fine. What?" I said.

She looked down then finally up and our eyes met.

"Scott, are you really, uh, you know, do my bottom?" she finally managed to get out.

I laughed, "Yeah sweetheart, I am most certainly going to fuck that lovely ass of yours!"

"I don't think I can take that!" she said very softy.

"Sure you can Cindy, besides I told you I'm not going to injure you. It may hurt a bit, but I'll go slow and easy" I tried to reassure her.

"It's just that, well, no one's ever done that to me before" she said with great apprehension.

OH GOD! This was too good to be true. I was going to get her anal cherry!

"I imagine that won't be your only new experience this weekend!" I chuckled.

She didn't say anything further.

"Ready to start" it wasn't really a question.

She blushed, but nodded yes.

"Stand up and undress" I said.

She stood. I could definitely still see a little fear, and quite a bit of apprehension in her face. I wondered if there wasn't a hint of excitement too!

And so we began. Me sitting in the chair as she started to unbutton her blouse.

To be continued...

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