You Got to Know When to Fold 'Em

She was standing, wearing only the diamonds, thong, thigh highs and "fuck me" heels admiring herself. Jenny looked down at her hand, removed her engagement ring and placed it in a box on the vanity. A tear ran down Jack's cheek.

Jenny needed a last-minute pee, so she went into the bathroom, and closed the door. Quickly and quietly, Jack seized the opportunity to enter the room, open the box, and slip the ring into his pocket, before returning to the doorway.

Jenny reentered the bedroom a few moments later and resumed gazing in the mirror. Her nipples were protruding in anticipation of that silky dress being pulled over them. Jenny gazed in the mirror, admiring herself before and after she slipped on the dress, and couldn't help feeling proud, damn, she was hot. The dress needed some kind of fix, her tits would be on display unless some tape was used. However, there was no time to get something like that, so preventing the dress from occasionally revealing her charms would be impossible. She knew all of the men around her that evening, were going to get glimpses of her boobs and ass all night.

There was something else to be seen in the mirror though, it was Jack. He had been standing there watching her admire herself. She had tried to hide these sexy things that Howie bought for her, to wear for HIM and she had failed. Jack had seen it all; under garments, the sexy dress, the diamonds, every whorish item. The look on Jack's face said it all: he looked like a man who had just lost his wife.

She started to speak, "Jack, please..." Then she noticed her fiancé's new look, realizing that he had a date.

Jack had seen and heard enough. He stopped her talking with a hand gesture, that featured his middle finger, and mouthed the words, "Fuck you, slut."

Then he lowered his head and walked out, slamming the door of the room and, possibly, on their life together.

The shock of his response froze Jenny for a few beats, Jack had never spoken to her like that. She ran into to the living room and, for a belated comeback, she hollered back at an empty room, "Well, fuck you too," and burst into tears.

A makeup touch-up was now going to be necessary; so, Jenny retreated back into the bedroom. Shortly after, a knock at the door broke the silence. She guessed that Jack hadn't locked the door when he left, so, assuming that it was her date, she hollered, "Come in, I'll be ready soon."

Howie heard the anguish in her voice, and walked into her bedroom unannounced under the pretense of comforting her.

She was startled by his audacity, "What are you doing in here? This is my bedroom. Jesus Christ! Get out of here now. What if my fiancé found you in here? How would I explain that?"

"I'd just have to tell him that I was trying to comfort you, after HE made you cry," Howie countered.

"He would fucking kill you, and then probably me. Get out, now!"

"Ok, I'll be right here when you are ready, take your time," he said, trying to recover from what was a significant blunder on his part.

Shortly, Jenny came out of the bedroom, ready to begin their date. Howie escorted her to the resort's main lobby, where a cab was waiting.

She thought, "See Jack, a cab not a limo, you're wrong." But it was more of an attempt to sell herself, that she was right.

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

Promptly at six, Jack knocked on the door of room 422. Diane, Cheryl's roommate opened it and invited him in saying, "She'll be ready in a minute, make yourself at home."

It had been five years since he had picked up a date other than Jenny, and it felt odd. It also looked odd, because Diane was only dressed in a bra and panty set, which displayed much of her well-developed body.

Cheryl came out of the bathroom and said, "Don't mind her, she loves to tease. Ready to go?"

"Yes, I'm ready, I have a 6:45 reservation at L'Isola, is that Ok?" Jack asked.

"Sounds great, I'm in the mood for Italian. Let's go," and Cheryl grabbed his arm and pulled herself up to give him a kiss.

She looked great with her blonde hair styled up exposing a tempting neck. The dark red dress she was wearing accentuated her impressive breasts and revealed just the right amount of leg, to grab a man's attention without looking slutty.

As they left the room Diane said, "Hey Cheryl, if you need any help, give me a call," causing both women to giggle.

They arrived early at the restaurant, having planned to enjoy the house bar prior to their meal. Jack looked the crowd over, reassuring himself that Jenny's 'dream date' was at a different location. She wasn't there, allowing him to relax and enjoy being with Cheryl. Dinner went well, with both betrayed lovers continuing to share their tales of woe. Each was impressed with the other's honesty.

After dinner, Cheryl mentioned a dance club, that she had heard was great, but cautioned that it was fairly expensive. Jack laughed bitterly, saying, "Nothing would give me greater pleasure than spending some more of the money that I was saving to get Jenny and me started. Let's go."

They went to the club and the two of them forgot their troubles for a good two hours, with minimal drinking and maximum dancing. She felt good up against him and the dread of what Jenny was up to with Howard seemed more distant. Cheryl also let herself be drawn into the moment, aware that this was a 'one and done' deal with Jack, yet she was determined to get a full measure of fun.

After the two wonderful hours of dancing, Cheryl was ready to stop the "pretend sex" on the dance floor and proceed to the real thing. They were locked together in a slow dance when Cheryl nibbled at Jack's neck and said, "Enough of this preliminary stuff, take me back to my room and fuck my brains out."

Jack didn't respond, verbally, just took her arm and headed for the door, stopping only to settle the tab and tip their waitress.

Arriving at Cheryl's room Jack asked, "What about your roommate? Will she be coming back?"

"Oh, I wouldn't worry about her. Anyway, if she did show up, it might be fun; what do you think?"

The possibility of realizing a fantasy that most guys have, a threesome with two girls, caused Jack to smile at his good fortune, then he kissed Cheryl hard. Clothes started flying and soon they were both naked on the bed, exploring, tasting, and enjoying the flesh of a willing partner.

He shifted his position and began to kiss his way from the nipples that he had caused to harden, down to her belly. She was writhing, and when he started nibbling in the vicinity of her pussy, she said, "No, let's treat each other," so they shifted into a 69 position, with her on top.

They worked at each other's sex, with absence of any hesitancy. As they approached their respective peaks, they functioned together, altering technique like a well-practiced couple, to arrive simultaneously. Their climaxes were intense and prolonged, due to each partner continuing to provide stimulus well after the initial goal had been achieved.

With the first of many rounds completed, Jack shifted from the 69 position by gently rolling Cheryl on her back, then spinning her around. He maneuvered into a missionary position, giving her tits some extra attention along the way. He made a move to kiss her, but paused, allowing her to choose whether to continue with mouths that had been freshly filled with each other's cum.

She didn't hesitate, reaching for him saying, "Kiss me lover." They began a desperate sharing of the nectar of love. He was hard again within minutes, entered her fully and began pounding her with more force than usually considered acceptable for first time lovers.

Cheryl understood the origin and accepted his aggressiveness, telling him, "I know baby, I'm hurting inside too. Give it to me as hard as you want. Don't worry, I'll tell you if it gets to be too much."

Without answering, Jack raised up and looked into her eyes, as if to apologize for being rough. Cheryl mouthed the words, "Give it to me hard. Pound me!" and pulled his head to an open mouth kiss as Jack increased his effort.

Their lust peaked for the second time and in the aftermath, they opted for a well-earned rest. Jack rolled partly off, to allow Cheryl to breathe more easily. When they'd caught their breath a little, she asked, "Stay all night, fuck me till the sun comes up. Please."

Breathing harder than normal, Jack said, "I was hoping for that," then rested his head beside her.

Cheryl was ready for a short breather also, but managed to text Diane, "Join in?"

Twenty minutes later the door to Cheryl's room opened, it was Diane, she said, "Well, since you two started without me, I insist on getting double duty from each of you, until I catch up."

Diane giggled hysterically as she shed clothes faster than a professional stripper.

Jack was rolled onto his back, and Diane took his cock deep in her mouth, spent love juices and all. Cheryl moved to a position behind her friend. As Diane sucked away on his cock, with her ass in the air, Cheryl used her tongue on her friend's bottom end.

Diane climaxed very quickly, but then shifted onto her back so that Jack could mount her. Cheryl positioned herself over Dianne's face, so that her roommate could enjoy licking a freshly fucked cunt, while Jack completed the 'double team' by plunging in and out of her pussy.

Jack lasted longer that round, having already delivered two massive loads. Cheryl peaked from the oral talent of her roommate, so she decided to help Jack fill her pal's snatch with cum.

A thrill of a lifetime came Jack's way, when Cheryl started licking his balls while his cock was thrusting deep into Diane. The feeling of pounding a beautiful girl, while another one was giving oral stimulation to his nuts, prevented any ability to hold out very long. When Cheryl teased his asshole with her tongue, he unloaded.

Cheryl said, "Hey roomie, I invited him to stay the night, Ok?"

"Fuckin' A, it's Ok!" was Diane's response.

By morning, they had done nearly everything two girls and a guy could do, including using a strap-on, enabling each girl to sample double penetration. They offered to give Jack the experience of simultaneously being a poker and a pokee, but he declined.

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

Jenny's evening did not pan out nearly as well as she had hoped.

First, she was worried that her fiancé, the only man she had ever truly loved was likely in the company of another woman. It was also, finally, starting to seep into her illogical mind that this entire disaster was her fault. At last she realized that she WAS on a DATE with another man.

Second, she was concerned about the nature of her current circumstances, namely being in the company of a man who had spent a fortune on her for this date and was, no doubt, expecting a substantial "return" for his investment.

She thought, "How could I be so naïve? Men expect something when they spend money on a girl, especially THAT much money. He did promise me that I didn't have to do anything that I didn't want to do. But $10,000 fucking dollars! Jesus, how could I be so stupid?"

Third, she was thinking, "Actually, Howie has come through on most of his promises, of an ultra-high-class night out, with his rich clients including a famous actor and an NFL star. Who would ever have thought, that I would get to be in the arms of a Hollywood legend and an NFL star, for a couple of slow dances? But while I'm bragging about that, do I mention that they both felt me up the entire time?

"My body has been on display, just like Jack warned. My tits keep trying to peek out, my left ass cheek shows every time I turn and every man here has been getting the show that I was warned about. Jack, please forgive me."

Then, the most terrifying thought of all, "Have I sacrificed any possibility of getting to do a first dance with Jack as man and wife?"

Lastly, as the night was obviously coming to a close, she pondered, "What am I going to do about whatever it is that Howie feels that he is owed? Jack was probably right; Howie likely does expect sex from me. After all that he's given me tonight, is it fair of me to NOT do something for him? But I don't want to go to bed with him, I don't even like him anymore. The longer this night has gone on the more he acts like he owns me, like I AM bought and paid for, like a whore."

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Continued in "You Got To Know When To Hold Them"