Executive Privilege Ch. 07a

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Chicago Suites - Emma claims her status
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Part 7 of the 9 part series

Updated 06/08/2023
Created 10/20/2006
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Keat
Keat
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Chicago Suites - Emma claims her status

The author gratefully acknowledges the editorial contribution of barefootgirl69.

The Executives at Andra Corporation had an arrangement with some of their subordinate employees. The wives of their subordinates could advance the careers and compensation of their husbands by making a personal contribution of their own. To enhance your personal enjoyment of this installment, the reader is encouraged to first read Executive Privilege Ch. 01 - The Arrangement

Emma Montgomery and her husband, Leon, a freshly minted Senior Manager of Andra Corporation, were on their way to Chicago. The pleasure of air travel wasn't what it used to be, but Emma was excited to accompany her husband on their first business trip together.

Six days ago, Leon had been promoted to Senior Manager and had now been assigned to assist his boss, Jamie Elkin, one of the company's Executive officers in trying to put together an important and potentially lucrative transaction for the company. Clinton Santini, another company Executive, and Santini's subordinate, Jim Cardin would also be working on the deal.

Gazing on the clouds below, Emma's thoughts drifted between her husband's responsibilities and her own. She knew Leon and Jim, as the junior members of the team, would be putting in extra hours, after their bosses had called it a day. She'd be working, as well, servicing her first two clients under their arrangement with Andra Corporation. As her husband's superior, Jamie had first dibs on her. For the coming weekend, she and Jim's wife, Lisa would be servicing the two married Executives - pudgy, Jamie Elkin and the handsome, Clinton Santini.

Under the arrangement, she could contribute to her husband's career and their future together. Her husband would receive substantial immediate and future financial rewards. In exchange, the corporation's top Executives would have the right to her sexual services and to use her body.

She and her husband had talked about this many times before and after they decided to join the arrangement. He assured her he could handle her having sex with the Executives. She took him at his word but also took the opportunity to have a post nuptial agreement prepared providing she would receive her fair share of the money they would be earning together. She wanted him to stick with the marriage and the arrangement wouldn't work if he didn't. She knew he was humiliated that he was being paid for her to sexually serve his superiors; in effect, pimping her out. As her husband, he would still be tested with jealousy and doubt. She also knew it would be her responsibility to keep her marriage partner number one in her relationships. Both were enthusiastic about the money but ashamed of what they would have to do to earn it

A private car was waiting for the Montgomery couple at O'Hare Airport. They held hands during the ride into town quietly contemplating their assignments. She absent mindedly fingered her husband's wedding band pondering the impact their planned adultery might have on their marriage. She was much younger than her husband. She often felt his jealousy if she made even casual conversation with another man. She loved Leon. At the same time, his promising career with Andra Corporation was a significant factor in her decision to marry him.

Lisa Cardin had gone over how the arrangement worked and some of her own personal experiences over the past three years. She warned that the Chairman and Jamie Elkin could be particularly demeaning. Lisa confided that her relationships with the Executives are purely sexual. She's promoting her husband's career just as each of their wives had helped their early careers. She respected their status and entitlement to her services. "I always put out my best for each Executive and usually have fun doing it," Lisa explained.

Like most women, Emma had fantasized about being paid to have sex. This would be different than a masturbation fantasy. This would be the real thing.

Leon didn't want his wife to have sex with the Executives but, he wanted the money and the potential promotion to Executive for himself. And, then, there were his own fantasies of his wife actually having sex other men. He was conflicted but, if this was too much for them, they could always end it ... and the financial benefits that went with it.

After a lot of back and forth conversation as husband and wife, together they agreed to the arrangement and Leon had already received his initial payments. Now it was time for her to do her part.

The car's first stop was to drop Leon at the high rise office building where the Andra team was meeting with attorneys and accountants. The second stop was at the five star Grand Peninsula Hotel. As Emma was exiting the back seat, her short skirt rode up above her gartered stocking tops revealing pale thighs and lace edged sheer panties. The doorman took full advantage of the view.

At reception, Emma was given her key and informed that Mrs. Cardin had already checked in to their suites on the 20th floor.

Lisa met Emma and the bellman at the foyer door of the common entrance to two suites. Each Executive suite had its own privacy but guests could pass from one to the other via the connecting foyer.

Lisa lead the way into Elkin's spacious living room separated from the master bedroom by open double doors. She directed the bellman to put Emma's luggage in the master bedroom and Mr. Montgomery's in the small adjacent bedroom. In the master, a mirror ran alongside the king size bed. In suite was a large bathroom with Jacuzzi bath, unenclosed shower, bidet and toilet.

Helping her unpack, she noted Emma's fashionable lingerie, loungewear and sexy evening attire. With a lump in her throat, Emma placed her toiletries in the master bath alongside Jamie's. She tried to imagine herself in this room with Jamie. Until she married Leon, her lovers had been young and fit or handsome older men with plenty of money. She'd never been intimate with a heavy man before. That was getting ready to change.

"I've been at this for three years now and never had a set up like this," Lisa confided. "Jim has watched me have sex several times, got fucked during one of my dates, on another masturbated with one of the junior husbands and, of course, as they're all required to do, he's blown each of the Executives. This is different. On a usual double date, they take turns on us which I expect this weekend. Since Jamie set this up, there's no telling what he has in mind for us or our husbands."

Emma's tummy did a flip flop. She knew full well she would be having sex but had not considered the possibility she would be sleeping with Jamie and sharing his bathroom facilities while her husband stayed in a room in the same suite. Sensing a little tension, Lisa suggested showers and then a get together over wine to decide what they would wear to greet their clients. "I brought extra enemas, if you need some," Lisa mentioned with a raised eyebrow.

"Thanks, I brought my own," Emma replied with a thin smile.

As she was drying her hair, Emma didn't hear Lisa come into her suite. She walked naked out of her bedroom to find Lisa, her mentor, sitting on the couch in a camisole and shorty panties sipping a glass of wine. "Wow! You were smokin' hot at the promotion party but even more beautiful in the buff." Lisa's face radiated her approval as she stood and walked toward the young woman.

Lisa took her time admiring Emma's glossy dark red hair and clear, smooth skin with the classic pale complexion often associated with that hair color. Her heart shaped face tapered from wide set green eyes to a small jaw. She was a true beauty.

Lisa handed her a glass of chilled white wine and took a moment to run her fingers through her luscious hair. Her firm nipples and large breasts gently pressed Emma's. Lisa's fresh scent and the warmth of her closeness were stimulating. Emma held her gaze but could not control her blush, so obvious on her pale skin. She wondered if sex with Lisa was in the cards for this weekend - like she had enjoyed with a couple of her college sorority sisters.

Emma slipped on panties and a tee shirt and they curled up on opposite ends of the couch in the living room

"I generally like older men. My father's best friend took my virginity a month after my 18th birthday," Emma confided. "I've been sexually active ever since. I've had some great lovers and some losers, like most of us, I guess. I knew it bothered Leon when I continued to see other men when we started dating, which is one of the reasons I did it. I wanted him to claim me. I think we're both going to be alright with the arrangement once we get some experience and some more of those fat paychecks."

"Oh, yes. The money makes the arrangement work ... as it has through history. You're going to be very popular. Every one of the Executives is going to want his turns with the gorgeous, young, new piece of ass."

Lisa went on to explain how a new couple is broken into the arrangement, "During the first several months, all the Executives are excited about trying out the new women. As a result, the new ones take a high volume of calls and get accustomed to dating the Executives as a part of everyday life rather than something new and special, like this weekend. Most of the time, you'll be taken on your marital bed, whether your husband's home or not."

"During your break in period, your husband's shame and jealousy will be tempered by your continued affection and sexual responsiveness to him after turning your tricks. Sometimes when you go to work it will disrupt a scheduled activity with him or he'll get upset listening to you schedule a date over the phone. Together you'll learn to accept the Executives new role in your lives, get accustomed to your new status and come to a higher level of bonding and appreciation for one another."

"Nowadays, after my dates, Jim and I have some of the best sex we've ever had. During a date, we're required to retain and wear their semen. No cleaning up without their permission. When Jim comes to our bedroom to reclaim me, I'm still all hot and sweaty with a stud's fresh load in one or more of my holes. It's a huge turn on for both of us. We've never been closer."

It was a lot for Emma to take in, but she appreciated Lisa's good intentions and the benefit of her experience. She felt like she had just been given a lesson.

"Emma, just to give you a heads up, Jamie's got a big dick. Not so long but thick," Lisa continued, "By the way, how's Leon in the size department?"

"OK. About average in my experience," Emma said. "Don't get me wrong, he's plenty for me and very satisfying."

Lisa smiled knowingly. "Of course he is," she said, "Some women like a big dick. I do, but for us it really doesn't matter. We're paid to do this. It may pinch at first but instinct will take over. You'll take it."

"You're going to be making a first impression on two of our clients this afternoon. You only get one chance to make a first impression. Sure, they checked you out at the promotion party and your photo shoot. This will be different. In the flesh. Any ideas on how you'd like to be introduced?" Lisa asked.

"I'm nervous," Emma replied, "This is very intimidating and humiliating. I'm excited, but I just can't think of what to say."

"Like all good first impressions, be open and confident," Lisa counseled, "Your body language and appearance are going to be much more important than what you say. If you want me to, I'll present you. Now that I'm thinking about it, I've got an idea how to show you off and for you to make an exciting, and an undeniable, acknowledgment that you accept your status in the arrangement. Trust me. Both men would be favorably impressed."

"Help me through this, girlfriend," Lisa encouraged with a smile.

"We'll dress for sex of course, but once you're stripped down, you could strike, shall we say, a provocative pose," Lisa continued, "let your body language do your talking so to speak." Emma raised an eyebrow but said nothing waiting for Lisa to explain.

Lisa gracefully rose from the couch and slowly walked in front of her. She eased her camisole from her shoulders, letting it fall to her feet. She slid out of her panties revealing the lusty mat of hair of a full grown woman. Maintaining eye contact with Emma, she took her time squeezing her breasts, pulling and pinching her nipples to erection. Breaking eye contact, she looked straight over Emma's head. Slowly, one movement at a time, she assumed a pose. Emma gasped. As Lisa confidently held her pose, Emma blushed in embarrassment and humiliation. "I could never do that," she whispered, "that's way past humiliating."

With understanding, Lisa ignored Emma's suggestion that she was above such a thing. "Of course, its humiliating. This whole thing is humiliating, but we're not hooking on a street corner or working on our backs in a brothel like common whores. Call girls try to turn two tricks a day and we're not doing that either.

After the first three or four months, you'll date once or twice a week. After a year, three or four times a month. It's safe, disease free, the clientele is limited to ten men and it's a well kept secret so the usual social stigma is avoided. Your husband's fully involved in the whole thing. Who he fucks is between you and him. If he fucks women not involved in the arrangement, it's got to be with a condom, 100% of the time, no exceptions."

"Sometime this weekend they're going to expect you to make a clear and express acknowledgment you understand what this all about. You don't have to use words, but they expect you to explicitly accept your status," Lisa said, "They'd be wowed, not to mention highly aroused, if a newbie introduced herself that confidently."

"I can't do it," Emma maintained, "It's too shameful." To herself she thought, "No decent, self-respecting woman would ever, ever put herself in that position." Again, she felt like Lisa was delivering a message to her.

It was fun getting ready for the men. Both women were naked as they made their selections. At Lisa's suggestion they brought the collars they wore at their promotion dinners - the red ribbon with gold clasps. She saw Emma's among her lingerie. Holding it up she said. "It'll be naughty fun wearing these later tonight." Emma smiled and nodded her agreement.

For her first impression, Emma wanted a soft, beautiful look rather than something aggressive and wild. Her breasts were bouncy and swayed a bit as she walked. She wanted to show case her tits. For this weekend, she had purchased a semi sheer haltered gown with a bodice opening below the bust line to reveal just enough of whats underneath to stir things up. With no panties, her dark red landing strip was tantalizing. She wore the only perfume she'd put on since she became a woman, First, now a familiar and arousing scent to her husband. No spikes this afternoon. This would be a strictly bedroom affair. She'd go barefoot.

"That gown really shows off your tits. What a hot package," Lisa complimented as she casually massaged Emma's breasts and brought her nipples to erection. "Nice," Emma thought to herself. She could picture herself having some fun with this hot brunette.

Lisa chose a black sheer baby doll top that put her own large breasts and prominent nipples on display. A matching sheer open crotch bikini allowed her full bush to show through and a glimpse of her long labia. Four inch spikes completed the sultry look she was after.

Jamie called from the cab and told them he and Clinton were on the way and that their husbands would be working late. The prostitutes checked their makeup and glossy red lipstick.

The men entered without a knock. They found the women at Elkin's living room bar pouring themselves chilled white wine. "Girls, we're ready to party! We've been talking about you during the entire cab ride," Clinton greeted. Clinton walked over to Lisa and murmured into her hair, "It's been a while, baby. I'm looking forward to being with you again." He pulled her in for a kiss.

"Whoa, big boy, we're all dressed up and ready for you," Lisa purred and playfully pushed him back, "Why don't you guys shower up and get comfortable? Then, I'll give you a personal introduction to this dark haired beauty." As the men were getting ready, the women prepared their cocktails.

Dressed in the hotel's plush bath robes, the men rejoined their women. Lisa insisted that they relax on the couch so she could serve them. She gave them a full turn in her lingerie. They admired the beauty of the young woman's body both had enjoyed over the past three years.

Breasts swaying gently under her sheer top, Lisa moved in front of Clinton Santini. She served him his drink and then reached down to pull her labia through the slit in her bikini, providing him an eye level view of her personal charms. As she served Elkin his cocktail, he took a good look at her erect nipples and between her legs, the lips he always enjoyed sucking completely into his mouth.

Emma felt her breasts swell and nipples harden as she observed this bawdy prelude to sex. Her clit tightened. Aroused, she began wetting herself. Soon she would be the object of their carnal attention.

Lisa beckoned Emma forward and placed her facing the men. She pressed her hardened nipples into her back to establish connection, in this woman to woman moment.

"Gentlemen, it is my pleasure to present to you, Mrs. Leon Montgomery," said Lisa as she slipped Emma's gown from her shoulders letting it pool at her feet.

Emma's blush deepened as her bare flesh was displayed.

The men took in her long, slender neck tapering into gently rounded shoulders, breasts full and taunt, medium size, pink areolas, erect nipples, graceful arms and a long, straight, firm back. Her small waist set off her nicely proportioned hips, slightly rounded belly, no excess fat there, and then the dark red strip of hair above her prominent pussy mound; below it her slit.

They were growing more aware of how very, very beautiful she was physically.

She saw their hungry eyes feasting on her body; a body that was theirs to use as they pleased. Her pale skin bloomed from her chest to her face and the top of her thighs glistened with her personal moisture.

Clinton caught his breath. She was lovely, gorgeous. He'd seen her pictures on the secured website. In the flesh, she was vibrant and eager. In a surge of desire, he wanted her but knew Jamie would claim her first.

"I'm sure we're all looking forward to playing with these lovely melons," said Lisa hefting Emma's warm and heavy breasts one at a time in a tawdry display. She squeezed her tits hard and then pinched and twisted her nipples until Emma squealed. Of course, they had the men's rapt attention.

Emma looked to Jamie, soon to be her first client. His robe had parted revealing his dick, stiff below his belly, about average in length but, a really thick shaft, capped by a large mushroom head helmet. It would be a stretch to get it into her small mouth much more, she winced mentally, her ass. It was certainly the biggest dick she'd encountered.

Jamie grinned. He delighted as the young woman realized that soon, very soon she would be mounted and fucked by his cock. His enjoyment was enhanced by her trepidation.

"Don't worry, baby," Jamie said, leering at her tits as he caught her looking, "It'll fit. It may take a little work, but it always fits."

Slowly rubbing her nipples across Emma's back, Lisa tenderly placed her hands on Emma's slender hips and whispered, "Ok, baby. Let's make this a memorable first impression. Look straight ahead. Take your time and put your hands behind your neck."

Emma's emotions were a mix of humiliation, embarrassment, lust and light headed shock. She knew where Lisa was leading her. Just a few hours ago she swore to herself she would never do this.

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