Executive Privilege Ch 08

Chicago Suites - Emma Takes a Calculated Risk

The author gratefully acknowledges the editorial contribution of barefootgirl69.

This is a direct continuation of Executive Privilege Ch. 07a. To enhance your personal pleasure, read it first.

There was only so much Emma could do for her shame faced husband. Now that she knew she would be servicing Clinton Santini this evening, she asked Lisa what to expect.

"Clint was my first. He took me in all three holes that night and he's fucked me for the last three years. He's older, married to a beautiful woman and has a married daughter, Danielle, about our age. She has a small frame, big tits and dark red hair a lot like you. Danni's husband works for the company. Clinton tells me he may be up for promotion to senior manager which means they'd be joining the arrangement," Lisa confided. "Clinton can be a great lover, Emma; I have a feeling you're going to enjoy him.

Leon was surprised to hear Lisa talking of Clinton as a lover. How would he treat Emma?

Emma liked older men. It's one reason she was attracted to Leon. She was highly sexed and enjoyed the self-control and authority an older man often had. Clinton would certainly be the oldest man she had ever been with; old enough to be her father. Inwardly, she was excited and, though Jamie had worked her over, she was looking forward to an evening of sex with another of the bosses.

In a loosely tied robe, Jamie rejoined them from the bedroom he was sharing with Emma, leaving the double doors open. It split over the top of his belly. This is the man that beat his wife this afternoon. Leon tried not to look at his cock but his eyes were drawn to it. He stared at his low hanging scrotum with massive testicles and thick semi hard penis swinging between his legs; the dick that fucked his wife this afternoon, a penis larger than his own. Jamie caught him looking, to Leon's embarrassment.

"Lisa, it's been a while and I'm glad to see you dressed for the occasion," Jamie smiled. He slipped the robe off, sat down on one end of the couch and beckoned her to him. She settled in his lap, belly to belly and reached forward to put her arms around his neck.

"I've always enjoyed our dates, Jamie. I've been looking forward to this weekend since Jim told me I'd be coming along," Lisa said loud enough for the others to hear. As they kissed, Jamie felt up her ample breasts, first tweaking then sucking her nipples to full erection.

"I've been hot for you all night," Lisa smiled, "How about some head to start things off?" Without waiting for an answer, Lisa slipped off his lap and lowered herself to her knees before him. She sat back on her heels so she was looking up at his cock. He was half hard. She was about to change that.

"Emma, be sure you get a good look at how a whore is supposed to suck cock," Jamie said, "Jim knows what I'm talking about don't you Jim?"

"I sure do. She's a slut and she loves that big dick of yours. Enjoy her Jamie. She's all yours." Jim replied with a smile and a thumb up.

Her husband is so smart Lisa thought. He saw an opportunity to pander Jamie and he took it. You just don't know what will be remembered when the time comes for a raise or promotion.

Lisa's luscious red lips parted, her mouth opened wide and she took the broad head of Jamie's penis in her mouth. Her lips traveled half way down his member and back up again, slowly, sensually. She wrapped her right hand around the bottom of his dick. She slipped him out of her mouth, massaging the underside of his head with her tongue. This stunningly beautiful, 26 year old brunette was a confident cock sucker. She could feel her pussy wetting as she prepared to receive this familiar thick shaft. She bent her head down and began sucking him deeply and steadily.

Jamie felt her taking him almost all the way down, his cock pressing against the back of her throat, her dark hair dancing as her head bobbed up and down on his shaft. Pressing deeper into her mouth, he could feel her gasping for air around his thick meat, but she didn't stop sucking.

"That a girl," Jamie in a demeaning tone, "suck that cock you little slut."

She came back up for a breath then, opened her mouth wide, stuck her tongue all the way out and down over her bottom lip making room in her mouth for his wide dick head. She took him all the way to the back of her mouth, then, firmly pushed his cock into her throat. Her lips were nestled against the hair of his groin, the engorged head lodged in her throat, swathed in her red collar. The experienced whore didn't gag or struggle with this big dick.

Emma was amazed. He'd beaten her because she wasn't able to take him into her throat. She needed a lesson from Lisa sooner than later. She glanced over to see her husband mesmerized watching her friend do her job. There was a wet stain on his pants at the top of his tented erection.

Lisa lifted her head to catch Jamie's eye to be sure he got a good look at her very personal service. Her brown eyes sparkled with desire. She hefted and gently squeezed his heavy nuts full of sperm. Sperm that would soon be inside her own body delivered by the big, warm penis she was pleasuring with her mouth.

Jamie's fingers slipped down to trail through the bounty of her hair and clutched the back of her head, holding it steady as she did her job.

She licked his big balls and took one into her mouth. Jim watched his wife suck one nut into her mouth, gently expel it and, then, suck the other all the way in. She was, by now, very practiced and very familiar with Jamie's manhood.

"Good girl, Lisa. You're a good bitch." Jamie said with condescending approval as he turned and met her husband's eyes. Jim knew the look. The Executive was exercising his privilege to his wife's sexual service even if it was to Jim's humiliation - right in front of him. Of course, Jim realized it was his decision to stay watch.

Clinton returned from his adjacent suite in chino slacks. He was a handsome man, bred from an Italian mother by a Spanish father. He was fit and very sexy, Emma thought, as he approached her and her husband.

Taking in the beauty of this slim woman, he moved close to the couple, his voice soft and yet strong. "You have a lovely body. I love your hair, and your breasts are gorgeous." He caressed her red collar.

"Thank you, Clint. I'm excited to provide you all the pleasures of my body. I'm all yours," Emma responded as she moved into his arms taking in his masculine scent. Seeing him come in for a kiss, she parted her red lips. As they embraced, he kissed her tenderly and she pushed her tits to his bare chest. At first, she merely submitted to his kiss, as was her place, but soon realized he was inviting more. She started playing her own tongue into his mouth.

Leon watched the scene unfold, heard every word and knew Clinton was inhaling her perfume as they kissed each other. He realized these were only the preliminaries. She'd sold her body and Clinton would fuck her, but why were they kissing each other? Inside he was shamed that his wife would respond to him with such a personal expression of affection.

Clinton acknowledged Leon with a polite nod, took his wife by the hand and led her to the couch. She hooked her fingers in the waist of her panties and slid them off.

When Clinton slipped off his slacks, Leon got his first look at the next dick that would be inside his wife.

He had her straddle his legs, making her labia flare and pussy accessible. He took his time stroking her pale neck, gently hefting and handling her tits enjoying the pleasure of feeling up her flesh. "I love your perfume," he murmured as he wound his fingers in her glossy dark red hair, a lover's touch that made his petting seem even more intimate and personal.

Leon watched mesmerized as his boss handled his wife.

She felt delicate and fragile in his arms. Emma wrapped one arm around his muscular neck and slowly ran the other through his hair enthralled with his kiss. She leaned close, pressed her taunt and swollen breasts to his chest and her face to his neck. She inhaled deeply and was further turned on by his personal aroma. Her nipples were hard and tight. His chest was firm and muscled, dark hairs decorating its center. She loved the feeling of the muscle definition of his arms, very masculine and extremely sexy.

He massaged her breasts, warm and soft in his hand, rolling her elongated nipples with his fingers. As his hand moved lower, Emma spread her legs further inviting his touch. They could both smell her musk. She shivered as a fresh wave of moisture soaked her pussy. Soon her hips were squirming as they made out like first time lovers.

"Clint, should we let the boys have some fun? Mano a mano?" Jamie asked as he looked over the tenting erections of the subordinates.

"Sure. Whatever," Clinton replied, his attention never leaving Emma.

Jim Cardin flinched; once before, desperate for relief, he had participated in this humiliating sexual activity.

"Jim, fill in Leon and then you guys can have at it. Enjoy," Jamie said with a smirk.

Turning to Leon, Jim explained, "We have permission to masturbate in a specific way. I put one hand on your shoulder, you put one hand on mine and we jerk off. We can jerk off each other or each handles his own dick. I prefer to handle my own dick. Touching is inevitable and at some point you're going to make a hot mess on me, likely more than once."

Leon got the picture. When Jim came, he would be ejaculating on him and vice versa. For sexual relief, they would have to make a carnal spectacle of themselves in front of their wives and the dominant males. The alternative was worse, no sexual satisfaction whatsoever.

"Fuck it. Let's do it," said Leon. As they stripped, Leon saw some lubricant on the nightstand in Emma's bedroom. Soon the two subordinates were lubing their dicks and in position to watch the action on the couch. The men faced one another in the required position for mutual masturbation. Once they turned their attention to the couples having sex, Leon found Jim was right. Their dicks were in contact.

Lisa's blow job was very pleasurable, but Jamie was ready for a change in the action. "Lisa, sit on my lap."

As she rose from her knees she looked at the lewd exhibition her husband and Leon were providing. She'd seen this once before. She gave them both an understanding smile and nod of approval. Oh well, in a moment she'd be putting on a show of her own.

She slipped off her panties and straddled Jamie with her knees on the couch. Leon found her trimmed but full bush sexy and arousing. Brazenly, she looked behind to be sure her husband and Leon were watching. Lifting herself into position, she set his broad cockhead at the opening of her vagina and with an up and down rocking motion impaled herself. She relished the stretch his thick mushroom head as he entered her body and his stimulation of her tits and nipples. She used her best technique to give him the most pleasure in this position that she could, establishing a slow, full stroke fuck occasionally pausing for a few quick pumps on his mushroom head with the muscled opening of her vagina.

Jim now understood her comments about how Jamie's thick member stretched her out. His girth was such that her long labia folded in and out along his shaft increasing her friction and pleasure. Both subordinates watched as the mouth of her vagina was pulled out of her

"Oh, yes, suck my nipples, Jamie," Lisa encouraged. She angled her hips to grind her clit on his body and his manhood on her G-spot. Lisa loved being on top, especially with a big dick inside her.

Jamie felt up her ass and then spread her cheeks, lewdly displaying her anus and their coupled genitals to the cuckolds. Jim heard his wife's aroused moaning and lustfully increased the tempo of his masturbation.

"Squeeze my tits. Bite me. Bite my nipples. Fucking bite me hard, Jamie," Lisa voiced her own craving and picked up pace of her strokes. She yelped in pain and pleasure as her stud accommodated her lustful desires.

Jim knew his superior's manhood was grazing against every sensitive part of his wife.

Clinton took a handful of Emma's hair and gently pulled backward exposing her neck. Smiling at her with sincere adoration, he whispered, "You're so beautiful." He and then covered her vulnerable neck and red collar with kisses. She felt him sucking the side of her neck just above her collar; again and again. He was marking her. She knew this was intended to be a public marking. "Thank you, Clint," she murmured as she accepted his mark.

Leon watched him move away from her neck lower toward her breasts and saw the mark. Another man was laying claim to his wife. As dark and purple as it was, that one would be there for a while.

When his lips reached the soft upper swell of her breasts, Emma sighed with pleasure.

He felt her trying to get to his erection. "Soon, baby girl. Try to relax and enjoy. I'm in no rush here, and I'm enjoying this immensely," he told her. Emma put her hands on his broad shoulders and felt up his musculature. He took her breasts in his hands and sucked one nipple while he pulled the other. Her sexual tension rising, she encouraged more intense stimulation, "Bite me, Clint." He did. "Harder" He did and she yelped. "Clint. I'm so horny. You're getting me so hot. I need you."

Leon was churning inside hearing her call Clint's name, watching them passionately kiss each other, watching him stimulate her body and her ardent response. Somehow this was harder on him than when he first knew for sure Jamie had fucked her this afternoon.

When he moved a hand to her pussy, she moved back a bit and spread her legs wider giving him easy access to her goodies.

Clinton knew, without checking, that she was fully aroused. He started slowly stroking her from the back of her vulva to along one side of her clit and then the other. Her hips were squirming, struggling to get direct contact with her clit. "Please. You know what I need," she was pleading for sexual release from his masturbation. She pulled him to her. The passion in their kiss was clear.

When he broke the kiss, she was so excited she was trembling. Intentionally, put his finger at the base of her clit, paused and met her eyes. He, then, firmly but gently stroked it up and down bringing her to climax.

For the first time, Leon witnessed his wife in an orgasm induced by another man. He tightened his grip on Jim's shoulder, unconsciously pressing his cock head onto Jim's as he reached his own sexual peak. Jim looked down as streams of Leon's ejaculate poured down his groin, soaking his pubic hair and squirted on his hand and penis providing extra lubrication for his own self pleasuring.

Clinton gently stroked her back as she basked in afterglow. She put her arms around his neck and her face in his chest deeply inhaling his masculine scent. Snuggled in his arms she murmured her appreciation, "That was so wonderful. You're so good to me. Thank you, Clint."

Jamie squeezed Lisa tits to get her attention. "I want you from behind. Bend over the arm of the couch," he instructed.

"Sure, Jamie. You know I love it from behind; especially with your big dick," Lisa said uncoupling from her stud. She moved around to the side of the couch, spread her feet and presented her ass. She assumed he wanted to finish in her pussy but that could go either way, and she had no say in the matter. Her breasts hanging, she waited for Jamie to mount her.

Jamie checked the status of the male twosome. They were in the proper position engulfed by the strong scent of semen; obviously Leon's. "Atta boy, Leon. You go right ahead and enjoy yourself while Clinton pets your wife. You like that don't you? She's putting out and you're jerking yourself off on your buddy while she's coming." Jamie was Leon's direct boss. He blushed in shame but held his limp member before him. Besides, Jamie was right.

Without a word, Jamie moved into position behind Lisa.

"Take me to my bed," Emma quietly asked. Clinton stood and with his hand in the small of her back, guided her toward her bedroom. They all noted the dark crimson color of the top third of Clinton's erection signaling his advanced state of arousal and Emma's ass reddened from her recent beating.

As they approached the paired men, Emma was embarrassed for both males. They had been forced to make a humiliating choice or face the frustration of watching with no sexual relief for themselves or banishment to their small rooms. She smiled at each of them warmly and stopped in front as they continued their mutual masturbation.

Clinton stood behind her, cupped her breasts and slipped his dick between her legs, his crimson head protruding, dripping pre cum. She rocked her hips, slowly sliding her wet slit back and forth along the top of her stud's erection. She was liking this man more and more.

She faced her husband. As they looked at one another, the pictures Leon had imagined of his wife with another man crystallized into sharp reality. To Emma, her husband was in the moment with her. She was thankful. "I love you," she silently mouthed.

Then she turned her attention to Jim, as he leered at her tits, erect nipples and her red gash massaging his boss's shaft. Shifting his gaze between her eyes and the action between her legs, he brazenly stroked his cock and swung his hips. His wanton lust for her was obvious.

Well, that wasn't going to happen. Not tonight anyway. He was using his masturbation as a simulated fuck which she found highly erotic. Her juices were now running off Clint's phallus. Her clit tightened. She felt compassion for the husbands in their humiliation, jerking themselves off. Emma slowly moved her hands down to her mons.

"Nice cock, Jim," she said with a smile, "I can see you are excited to see me."

She looked over to Lisa just a few feet away and gave her a wink. "Let me show you how excited I am to see you," she carried on. With two fingers, she pulled back her hood, displaying her own erection. Locking eyes with Jim, she reciprocated his fuck motions with her own hips along her lover's erection, signaling her response to his lustful interest in her. "Show me how you really feel about me," she said, "Don't hold back. Come for me, Jim." It was the best she could do for him under the circumstances.

Now Leon felt Jim's hand tighten on his shoulder and heard his grunt. Jim looked up to her beaming smile. "Ahh, ahh, ahh, Emma, Emma!" Jim panted as his ejaculation exploded onto her husband, soaking Leon's penis, hand and groin with stream after stream of his semen.

"My pleasure, Jim," Emma said smiling at him and her hubby. Both men had their eyes on her red ass as she led Clinton to her bed.

Lisa saw it all. Appropriately, she was glad her loving husband had some sexual relief and inwardly thanked Emma for providing it. There would be an evening in the future when she would invite the Montgomerys into the Cardin bedroom.

With one hand, he found Lisa's warm hairy hole and then used his thumb to pull her open. With his other hand he guided his dick to her cunt. She took a breath and looked over her shoulder. "I'm ready for this, Jamie. Gimme a hard fuck. Don't hold back," she said loud enough for all to hear.

Jamie firmly gripped her hips and adjusted her position. "Push your cunt back."

Lisa complied. Holding her in position, the dominant male took her with slow full thrusts into her body.

Leaving the subordinate males in their messes, Emma led Clinton through the double doors to the bed where she would later sleep with Jamie. Reclining as lovers, her hands caressed his chest, arms, legs, and ass; she cupped his balls and lightly stroked his penis. His hands were on her neck, back, breasts and her ass. They were touching every part of each other. With one hand behind her head, he kissed and nuzzled her neck.