You Got to Know When to Fold 'Em

"My god Howie! That would cost thousands, and we've just met. I'm not comfortable with you spending that kind of money on me," she responded.

Undeterred, he continued the press, "It's not a devious plot my dear, let me explain. My company pays me well to schmooze rich clients. The company is paying all expenses to fly them down here and show them a good time. I don't want the fact that I am a widower putting a downer on this dinner meeting. My company stands to make millions from securing their investments, so paying a mere eight to twelve thousand on an outfit for you, to make me look like a winner, is a no brainer. All legit. All upfront. Jenny, can I count on you?"

"Will there really be famous people attending?" she said, her integrity sagging.

That set the hook in her mouth, now all Howie had to do was reel her in.

"Not only attending, but they will be sitting at our table. As beautiful as you are, I'm sure that they will be impatiently looking for an opportunity to ask you to dance. It's my job to see to it that they get that chance, so I'll be entertaining, or more truthfully, distracting their wives. Believe it or not, that is exactly what these clients want me to do. With their wives occupied, they are free to pursue you for a dance or two. They will be delighted to get to hold you in their arms, at least for a few minutes," he said, appealing to her fascination with famous men.

What a closer! He was sure that she would go, if he could interject one more thought into her lovely head. "Jenny, if Jack really loves you, he should want you to have this opportunity. I know it might hurt his ego a little, that I'm providing something that he could never afford to give you, but this is a once in a lifetime thing. He owes it to you, to support your decision," he said, smiling, realizing that she had bought the crap that he was selling.

"Howie, what you say makes a lot of sense, but I love Jack with all my heart. I can't answer you right now, not until I talk further with him. I know he loves me, but honestly, he does not trust you. He's certain that all you want is sex from me."

"Nothing could be further from the truth, it's a dream evening out on the town. Would it help if I came over and talked to him, to put his mind at ease?"

"No, I don't think that would help. In fact, that may really be bad," she warned.

"Alright then, I'll leave it to you. Call me when you've decided, but it will have to be soon, Thursday will be taken up shopping for your ensemble."

"Ok, Howie, I will call with an answer soon," she promised and headed back to the bungalow.

Upon arrival, she found Jack waiting for her. Before she was able to get a word out, he started the conversation, "Where have you been?"

"I went for a walk on the beach," she said, afraid to tell all.

"You went to see him, didn't you?" Jack said, the contempt in his voice was stronger than it was the previous night. His trust was eroding, and he believed that she was now lying about her activities.

"Jack, I didn't start out to go there, but as I was walking past, he offered me coffee, and to talk about Friday," she stated becoming a bit defensive, due to guilty feelings creeping about in her subconscious mind.

"I can't fucking believe this. I'm not paying for a bunch of new clothes for you to go out on a date with another man," he said.

"You don't have to. Howie's company is paying the tab for my dress, it's to impress some important people including two celebrities, and it is NOT a date," she stated, thinking that she had made a valid point, but his response diminished her victory.

"Not a date? Well let me add this up: This guy, who you hardly know, is going to take you shopping, tomorrow I suppose. That means that of our seven days here, he is going to monopolize two of them, not counting fucking up today.

"Then the plan is: Friday, he'll come over here, and I'm supposed to invite him in like I'm your father or something, maybe offer him a drink. Then you come out, dressed fit to kill, probably sexier than I've ever seen you. Maybe I get to kiss your cheek, because I wouldn't dare smear your makeup for him.

"Then, I guess, I shake his hand and tell the both of you to have a great time as he puts his arm around you and walks you to the car. I get to go sit in the room alone, and play with my dick while you are out allowing a fucking rich geezer, access to your goodies while drinking and dancing. Oh yeah, I should also be happy for you because you are going to get groped by some celebrities.

"Then, when you get in the car after the ball Cinderella, you'll find that it's time to pay the piper for all those thousands of dollars he spent. Guaranteed the car will be a limousine, with a driver, so he can be in the back seat with you, ready to collect. So, you get to try and decide if a blow job will suffice, or maybe a lot of groping and kissing in the car will do it. Or maybe considering all, you just go ahead and fuck him. That's what a whore does, isn't it? Quid pro quo?" he finished his rant.

This tirade from him astounded her. She responded weakly, "It is not like that, it is not a date. And don't you dare call me a whore! If you really loved me, you would be positive about allowing me this luxurious evening."

Jenny continued, "You're just jealous. It is NOT a date. Don't you trust me?"

"I don't trust HIM! What do we know about him? NOTHING, that's what. I'll tell you something else, I checked in with my office this morning. I can't prove it yet, but I'm pretty sure old Howie was behind my getting called off of the beach yesterday. The 'big crisis' was nothing important at all, definitely not something to call me down here about. The prick wanted me out of the way, so he could tempt you with a dream date," he replied.

"I don't believe any of that. I want to go, I AM going to go," she stated firmly, said as if she had given the subject thorough consideration and arrived at the logical answer. The truth was far less certain. Deep in her mind, she doubted that accompanying Howard wasn't actually a date, and whether she wasn't being blinded by the lure of fame and fortune.

"You're over 21, and you can do as you wish. But know this; I'll be reevaluating our relationship and I might just follow your lead. There's a college girls' soccer team down here for an extended get away. Maybe I'll see if I can get an escort, for dinner and dancing Friday night."

"You would do that to me? Cheat on me?" she queried.

"So, it's not a date when you do it, including the 'gentleman' buying your outfit, but if it's me, and I'm not even offering to buy anything more than dinner, it's cheating."

"You wouldn't be doing it for the same reason," she argued.

"Don't bet on that with anything that you can't afford to lose, my... love?" he answered, sarcastically turning a statement into a question with the inflection of his voice at the end.

"I'm going, do what you want," and with that she stormed into the bedroom and slammed the door.

****************Thursday****************

The next morning had an Alaskan worthy chill in the air in the room of these two supposed lovers, not a word was spoken. Around 10am Jenny got a call from Howie and deliberately moved out of Jack's hearing range.

Ten minutes later, she informed Jack that she was going out shopping for a while, trying to make it seem as though the call and the shopping were unrelated. The ploy could not have fooled a 3-year-old, Jack knew who it was the moment her cell rang.

"I suppose that was asshole on the phone and he's going to take you out and buy you some hot things to wear for him tomorrow night, things I can't afford?" Jack said, in a tone laced with venom.

"What if it was him? He just called to say good morning and ask if I had decided. I told him yes," she stated defiantly, as if knowing that she was stepping over a boundary.

"Just remember what I told you... I'm not kidding. I do not agree to this. It IS a DATE, one with another man. If you do this, it will finish us," Jack replied, and left for the beach, alone.

"Alright," he thought, "I'll spend a little time further down the beach, at the volleyball courts. Let her spend the day shopping with old fucking Howard. I'll see if I've still got the old mojo and land a date with a sweet young honey."

When Jack departed, he took a short cut to the beach volleyball court through a hallway. Jenny had a sudden attack of guilt and ran after him, wanting to reiterate that being Howie's escort (she couldn't bring herself to call it a date) was just platonic, and Jack should NOT seek female companionship.

She was too late; Jack had already disappeared. This sent a chill down her spine, because if he had headed to the section of beach where they had always set up, he would still be in sight.

*********************************************

Jenny intended to meet Howard at the resort lobby, and was startled when he knocked on the bungalow door. She thought, "What if Jack was still here? Howie calling for me here right now would definitely cause trouble."

"I thought that I'd accompany you like a proper escort, and not make you meet me in the lobby, as if we were sneaking around," Howie said.

"Actually, Howie, I am starting to feel like this whole thing is a bad idea, Jack is really pissed off at me."

"How could any reasonable person think ill of our plans? We have done absolutely nothing wrong, and it doesn't seem fair that he would deny the woman he loved an opportunity to live the high life a little, does it?" he coaxed.

"I keep telling him that we are NOT going on a date, but he makes a pretty good argument," she admitted, wanting to be assured that she was not cheating.

"What did he say that upset you my dear?" Howie asked.

"His point is: you propose to come pick me up, dressed up in an outfit that he probably couldn't afford. Then take me to a world class dinner with important people, with drinking and dancing, and that he had been excluded. Further, he wasn't even considered to be invited, by me. He finished by saying, 'If that's not a date, then what is?' and I don't have a good enough answer," she related.

"Well, as far as inviting him, I didn't think that he would fit in, I didn't want to embarrass him. As for the other, yes there will be cocktails and dancing. Now shall we go, I promise that if you change your mind later, you still keep the clothes, even if you back out on your promise," his use of "promise" was deliberate, he wanted her to feel like she could not renege on her word.

"Alright, let's go. I don't know where he is anyway," she said, but she was worried that she knew damn well where he had gone.

*******************************************************

When Jack arrived at the courts, several girls and some guys were starting to gather. Introductions were made and Jack bought a round of drinks for everyone, immediately endearing him to the new group. Jack was an athlete in college and was an asset to whichever team picked him. By the end of the afternoon three of the young women, noticing no ring on his finger, six pack abs and piercing blue eyes, seemed to be definitely interested in him.

Jack hung with the girls and a couple of guys for the entire afternoon, played volleyball, drank beer, and enjoyed the beach. He wondered if Jenny would come looking for him and fuck up his preliminary acquisition plans. He kept an eye out for her, but she didn't show.

He wondered, "What if the old asshole has been able to get her head spinning enough to have already closed the deal on her pussy?" He decided that, although unlikely, it was out of his control, so he might as well see if he could get a nibble from one of these girls for a date.

Betty was sitting on a towel close to him and as he began his pitch, she shut him down by quickly saying, "You're as cute as you could be, but I've got a guy, a good guy and I won't fool around on him, period."

Jack thought, "Damn, I wish Jenny felt that strong about contact with other men."

"Anyway, you should talk to Cheryl. She's the blonde on the left, one of the girls that you were playing ball with," she said while pointing out to the surf. "She has a crush on you. She broke up with her boyfriend last month and could use a little fun. Cheryl said that she would do you in a heartbeat! Oops, I probably shouldn't have said that... please don't tell her that I blabbed," Betty said.

With his target identified, Jack made his way into the surf. He moved closer to Cheryl than anyone else and started a well-practiced schmooze. He didn't actually have to try too hard, because she had wanted him from the moment that he was picked for her volleyball team.

Jack was honest with Cheryl, as they sat on the beach, each revealing their troubled love life. They were sharing the same beach towel with Betty, and she heard everything the two were saying. Finally, Betty told Jack, "Jesus Christ, dump that bitch," referring to Jenny.

Cheryl whispered in Jack's ear, "Betty is a hell of a gossip, she'll tell everybody here about your woman."

In the end, Jack and Cheryl agreed that what they both needed was some good company: no love, no promises, just a good time. She accepted his offer of dinner, dancing and whatever for the next evening. He would call on her at sixish, about the same time that Howard was to pick up Jenny.

*************************************

Jenny's shopping trip took a turn that she had not expected. Howie picked out an extremely sexy, expensive and decadent dress. It was cut deep to the belly button to show off her tits, and slit up the side to her ass. He also had insisted on purchasing her lingerie items, thong, thigh high stockings, and a new pair of "Fuck me" high heels. She did manage to draw the line and refused, when he suggested that she model them for him.

Their last stop was an upscale jewelry store. Howard insisted on a diamond neckless, with matching earrings and bracelet. Jenny balked at the price, but Howard insisted and once again assured her that his company was picking up the tab and that she'd be able to keep them forever as souvenirs. The addition of the jewelry increased the cost of the ensemble that Howard was providing to approximately $10,000.

She felt that she couldn't say no to this date, these things were beyond her wildest dreams, but she worried how she was going to be able to get out and back into the room without Jack seeing her dressed in these things. She feared that he would call her a whore again, and she silently pondered, "Would that be right, am I a whore for accepting expensive gifts from a strange man? I'll have to get rid of this lingerie and these diamonds, I don't dare let Jack see these things. I wouldn't wear something so daring in public for my future husband, so why the fuck am I willing to wear them for Howie?"

Howie sensed her hesitation; his move was to gather up the purchases and whisk her back to her room before she had time to reconsider. It worked, she realized that she would look amazing in this ensemble.

Howie walked her to the bungalow door and attempted to get a full, on the lips, goodbye kiss. However, she turned her head and made it a kiss on the cheek.

This guy had nuts as large as beach balls to try that. If Jack had witnessed that attempt, at getting that kind of kiss, and then made them show what was purchased for the date, Howard would have been spitting out teeth, and Jenny might not need that ring on her finger any longer.

However, Jack was in the shower, so Howard slid by one more time without physical damage.

Jenny took the opportunity of Jack's absence to hide the lingerie, diamonds, thong, thigh highs, and high heels in her suitcase. Then locked it, and hid the key.

When Jack finished his shower, he didn't show any interest in her shopping trip. Instead, he asked emotionlessly, "Where do you want to eat?"

Jenny worried that he didn't care enough to quiz her about the afternoon's activity. She wondered, "Will he follow through with his threat. I don't know what I'll do if he goes on a date with some pretty thing. She'll want him, any female that's not crazy would want him. I wish I could stop this. But Howie spent about $10,000 on me today, so what can I do? I have to go."

Then, responding to Jack's question she said, "I don't care, anywhere I guess."

So, anywhere it was. The local "Beach Bar & Grill" wasn't the classiest place, but Jack was feeling the heat of Howard taking her to a dinner to remember the next day. He figured that a cheap meal with Jenny would save money that he could spend on Cheryl the next night. He felt somewhat empowered by denying Jenny something and giving it to Cheryl instead.

****************Friday*********************

When Jenny woke, Jack was already gone. He had not left a note, and when she tried to call him, his phone went straight to voice mail. She got a bite to eat alone and then went for a walk on the beach, in a direction opposite from Howie's villa. Her stroll in that direction went by the area where the college girls' soccer team had been playing volleyball. There were several people actively smacking a ball around, but no Jack.

She stopped to inquire about him, learning that they hadn't seen him. She was certain from their response, that they knew him. In addition, from the smirk on the face of one young woman, more was known than Jenny would have liked.

Jack had been busy all morning securing a couple of things for his date, and deliberately ducking Jenny. He had said his piece, now, he needed to see if she would go through with this relationship-ending date. The decision had been reached that unless she voluntarily backed out of it, he would return home as an unengaged man. As soon as Jenny wandered back in the direction of their bungalow, he joined his new friends and began playing ball with them.

Jenny had a hair appointment, so the search for Jack had to be suspended. On her return, she decided to stroll the other way up the beach, near Howie's place, just in case Jack had gone there to confront him. She walked to within 30 yards of the villa, stopped and listened. Nothing, no sounds of a fight, no one in view, although she was pretty sure that Howie was there, she thought, "He's probably relaxing, hot tubbing or napping before our date. Oh fuck, now I'm thinking of it as a date. I should go up there and cancel this."

For 15 minutes she stood there, mentally debating, one moment ready to cancel, and the next, wanting to have this once-in-a-lifetime dream date. On the sixteenth minute she turned and started walking back to the bungalow. Jenny decided that she would go through with the date, consciously taking the chance of being able to reconcile with Jack. She forced the thought of him ending their engagement, and spending an evening with another woman out of her mind, by convincing herself that he loved her too much to go through with those threats.

Jack was at the bungalow when she arrived but, when she approached him to talk, he immediately left for the bar. She was in the process of getting ready for her night out, when Jack returned to prepare for his date.

Earlier that day, wanting to dazzle Cheryl, Jack had purchased some new clothes, with a younger look. Next, he went to a barber shop, and had a touch-up haircut.

When Jack returned after downing a couple of shots of some Tennessee whiskey, Jenny was occupied getting ready for her evening. He had already put all of his new clothes in the spare bedroom, so he got ready without having to be in the same room as Jenny.

Usually, women take a little longer preparing to go out, Jack was still in the Bungalow as Jenny was 90% ready. She thought that she had heard him leave when the door slammed, and was feeling relief that he wouldn't see her dressed so decadently. He had left, but forgot the new watch that he had purchased with money that he had been saving for their honeymoon. When he went inside to retrieve it, he couldn't stop himself peeking at her getting ready in the bedroom.