Executive Privilege Ch. 05

Lisa put them both on the recommended diet in preparation for their out call and made sure Jim stayed fully hydrated. She wanted his pre-cum and semen copious and both of their juices mild and tasty. Wearing white cotton panties and a sleeping bra she snuggled into bed with her husband that night.

"You may as well relax honey. No nookie for you tonight and no self entertainment either. You are expected to be at your peak tomorrow night."

Jim understood. Abstaining the night before was actually part of the written protocol for a male out call under the arrangement. He lay thinking of the many times Executives had copulated with his wife in this bed and yet - now to enhance their pleasure - he was deprived of having her himself.

The next day, Friday, Jim saw Dean from a distance a couple of times. In the usual way, since a call was on, both men kept their distance – that is until Dean stepped onto the elevator with Jim as they were heading home. Alone in the elevator car, Jim commented he was glad the hectic week was over. Dean looked Jim square in the eye, smiled and said he was looking forward to starting the weekend.

"I'm getting hard just thinking about getting in your wife's panties tonight."

Jim blushed deeply as he watched Dean adjust his cock in his pants. He was embarrassed and ashamed that Dean so pointedly reminded him that he had the right to his wife's sexual favors. Earlier in the day this would have been out of line under the accepted protocol. Headed home this way, Jim chalked it up to Dean getting an early start on the evening.

Lisa had had ffm sessions with most of the Executive couples. She told Jim that the Executive wife had always taken the lead as she expected Emily Tagg to do this evening. Lisa emphasized the importance of staying in character.

"The Executives are highly stimulated when we acknowledge their dominance. You've seen me do that plenty of times verbally and physically. I'll be Dean's whore tonight in front of you. Don't worry about it. You may find you enjoy it." Lisa smiled at Jim reassuringly. Little did she know of the dynamics that would actually transpire.

Lisa expected one or both of them would be used for anal sex. After her first time with the Chairman in Las Vegas, when she anticipated anal, she usually took an enema. She decided an anal cleansing would be prudent for both of them tonight. She told Jim when she finished hers that she would help him with his. While she took care of herself, Jim spent the next thirty minutes contemplating the implications of having his wife flush his bowel in preparation for possible use by Dean or Emily or both. What the fuck had they gotten themselves into? No convention governed how a senior manager should dress on an out call. Lisa had bought Jim a pair of white silk pants for the occasion. Loose and bedroom sexy, he'd need a jock or his cock would quickly tent the fluid fabric of those pants. Lisa choose a snug black leather thong for him that confined his cock but let his balls hang through a comfortable hole in the bottom. The leather showed through the silk but Lisa thought that made the combo sexier still.

For herself, she dressed in her favorite outfit - a black open cup bra with matching garter belt and black fishnet stockings. Her slinky red dress with its high cut on her hips and its plunging neckline never failed to make her feel sexy and ready. She had bought new six inch black stiletto platforms. Since the first night of their introduction into the arrangement, Lisa had made crimson lip gloss her trademark. Some strategically placed perfume and she was ready for their finishing touch.

Lisa had bought a pair of new matching black leather collars. Far more ornamental than functional, they were intended to make a visual statement of submission. She actually enjoyed snapping Jim's into place.

"It would do all of these men some long term good if they each had an occasional session on the service end of the arrangement," she thought to herself.

Lisa knew Jim was nervous as they drove to the Taggs. She had him unbutton his shirt to just above his belt. There was just no way to dress a man for this kind of thing but she wanted Emily to realize they had put forth the effort. Jim was a good looking guy and that wasn't lost in the overall look.

The Taggs greeted them together at the front door. Emily had her long brown hair up, displaying a graceful neck and cleavage. Bra-less, her ample breasts swayed beneath the gossamer material of her stylish dress.

Jim had always liked Emily. Even though she was the wife of an Executive she was always friendly, even flirty with him. He blushed as she groped the front of his slacks and found the leather thong.

"Oooooo. I'll bet that's going to be a tight package before too long," she said, leading all of them all into the living room.

The men fixed drinks while Emily and Lisa sat on the sofa and began chatting. Emily asked if Jim had abstained last night. Lisa assured her that he had and was primed with a full load. When Lisa found Emily checking out her breasts, she stood and removed her dress, giving them all a good look at her young body displayed in sexy lingerie.

"The matching collars were a great thought Lisa. Dean and I have really been looking forward to this," Emily complimented.

They enjoyed their cocktails as the sexual tension began to build. Lisa noted the tent building Dean's pants.

"Strip. Both of you," Emily said in a husky voice.

Show time. Moving beside his wife, Jim stripped to his leather thong while she shed her lingerie. She turned and bent at the waist to put her stilettos back on ,offering Emily and Dean a good look at her ass, pussy pouch and labia. Jim's cock was swollen and uncomfortably constrained. He was very self conscious of the fact that Dean was checking out his balls hanging beneath his thong.

The attractive prostitutes stood facing the Executives, naked, collared and ready for sexual service. Locking Jim's eyes as she walked to him, Emily checked his tight package and then reached below to grasp his hanging nuts. He gasped when she gave them a firm squeeze, relaxed her grip and then squeezed firmly once more. It wasn't intended to hurt and it didn't, but she had made her point. The Executive wife had him by the balls and had let him know it in no uncertain terms.

Lisa smiled inwardly. Good for Emily, and a good object lesson for Jim.

Emily let her dress fall in folds at her feet. Naked, she settled into an overstuffed arm chair. Watching Jim all the way, she slowly lifted each leg on to a padded arm presenting her sex to him. She nodded once in his direction. Jim walked over and dropped to his knees. Emily started slowly massaging her own breasts and pulling on her nipples. As Jim parted her hair, he inhaled her personal scent deeply. Her vulva spread, he saw the moisture covering her labia, wetting her hair and pooling at the bottom of her slit.

Dean stood beside his wife, slowly taking off his clothes and watching Jim prepare to service her. When he had undressed he said simply,

"Lisa."

Lisa knelt before him stroking his firming cock with one hand while weighing his balls with the other. She made a ring with her thumb and forefinger just above his balls and then gently pulled down stretching his scrotum. Looking up she met his eyes and took his straining penis into her mouth. She didn't have the reputation as the blow job queen of the stable for nothing. Her technique was practiced and skillful. They all heard the wet and sucking sounds of her fellatio. Jim would have looked but Emily had both hands on the back of his head now slowly humping the lower part of her vulva on his face.

Lisa looked up to find Dean smiling and then glanced over to the armchair. Emily's mouth was open in a sexual pant and she was staring at Lisa. Not breaking eye contact, Lisa moved her mouth to the head of Dean's cock and opened wide enough to let Emily see how her tongue was flicking the underside of the head of Dean's penis. She intentionally displayed to Emily an oral technique enjoyed by both men and women.

"Lisa, come over here and finish me off," panted Emily.

As Lisa moved into position Jim looked over at Dean, his stiff cock wet, red, and drooling pre-cum. Dean met his eyes. From the look, Jim knew what was expected. He knelt before his superior and fixed his attention on the erection just inches from his face. Looking up at Dean, he took it in his hand, pulled it to his open mouth and took the cock. Now they heard the sounds of Jim servicing Dean.

Lisa was driving Emily into a frenzy. She massaged Emily's G spot as she flicked and sucked her throbbing clit. Emily gripped the arm chair tightly as she whimpered cries of pleasure and passion. "Ahhhh" Emily moaned as her orgasm rose from deep within her causing Lisa to feel her contractions around the two fingers she had now thrust deep into Emily's vagina. Emily's legs were shaking on the arms of the chair.

Watching his wife climax brought Dean over the top. With no more warning than a sigh, he began his own release. Jim heard his sound at the same time he felt the first jet of Dean's ejaculation fill his mouth. The sudden warmth and volume of his semen were new sensations to him. He tried to swallow but found swallowing more complicated than usual with a dick in his mouth. The third stream of Dean's orgasm was too much. Jim just let it run out of the sides of his mouth and drip down onto his protruding leather thong, finally running down his balls. He held Dean's cock with one hand, cupped his balls with the other and sucked the remains of his tapering orgasm. Looking up at Dean, Jim slowed to gently suckling his superior's penis.

Lisa gave Emily plenty of time to enjoy her afterglow, gently stroking her thighs and sides as she began to clean her up with her tongue. She started in the back prompting Emily to accommodate her by sliding down further in the chair. Lisa could then more easily spread her shapely ass more easily and get where she needed to be. By the time Lisa made her way to her clit, Emily said she felt thirsty and was ready for a fresh drink.

Jim and Lisa went to prepare more drinks for the Executive couple. Their faces still wet from sex, they looked at each other as they worked. Jim saw his wife's pubic hair soaking wet. Lisa saw her husband's cock straining in his thong and Dean's semen on the leather and on his balls. Lisa reminded him not to clean up until given permission.

"So, that wasn't so bad after all was it?" she asked Jim.

He agreed it wasn't that bad but he felt humiliated by the experience.

"No shit? Well, now you know how it feels. Believe me that was nothing compared to what it can be. Remember honey, I go through this once, sometimes twice a month," Lisa responded.

Emily allowed Jim to release his cock from the constraints of his leather thong as they sat together on the couch. They all watched him carefully work free one testicle at a time. Emily knew he wouldn't last long enough to give her the level of satisfaction she sought and would just make an unnecessary mess between her legs trying. She handed him a napkin and told him to jerk off.

Blushing deeply to his chest, standing before them, Jim stroked himself as the others sipped their cocktails. Jim noticed Kevin was fully erect and then couldn't help but meet his eyes. Jim's humiliation deepened. They were discussing how long it would take him to come. Lisa chatted casually about the fact that she had put him on the out call diet and had him fully hydrated. They seemed in no hurry whatsoever for Jim to finish himself off and looked to be genuinely enjoying the spectacle he was making of himself. After a few minutes, Jim pulled his penis downward and released a massive load into his napkin, careful not to spill.

Emily led the way to their bedroom. Jim watched his wife move to the bed and spread her legs for Dean. Emily followed suit settling herself comfortably beside Lisa. As Dean moved into position between her legs, Lisa lifted her knees and raised her vulva, inviting sex. Jim found it obscene and exciting to watch Dean approach his young wife - his cock fully erect - its purple helmet drooling a long strand of pre-cum. For the first time Jim watched another man mount his wife. There were no tender preliminaries. With one hand on his erection, Dean centered his cock head on her hole and thrust forward. With the second stroke he had taken her to the base of his cock then commencing long strokes. He watched his wife draw her knees back and shove her cunt up at Dean's lunging cock. He had certainly heard her have sex with other Executives but, never witnessed the carnal act.

Jim took his time massaging Emily's breasts and sucking each nipple to full erection. He leaned down for a kiss. Emily licked around his mouth savoring her husband's semen still sticky on his face. They shared a deep kiss.

"Take your time Jim. I want a slow penetration." Soon she felt him slowly enter her wet and swollen vagina, taking his time to stimulate the rim before entering further. Emily enjoyed the feel of a slow initial entry.

Spreading her legs widely for maximum penetration, Emily pulled him into a slightly higher mount so she could massage the cheeks of his ass and to provide a better angle for her to grind her clit against his pubic bone. Jim felt her slow down, give him a strong squeeze with her vagina and announce,

"Its really going to turn me on when Dean fucks you in the ass while you are inside me."

All of them heard it. Jim froze as a lump formed in his throat. Lisa saw Dean and his wife exchange knowing glances. Clearly, this was preplanned and not just a spontaneous thought of Emily's.

When Dean withdrew from her, Lisa turned on her side and then knelt beside Jim and Emily. She stroked his back reassuringly and massaged Emily's closest breast. Lisa knew what was about to happen.

Emily spoke.

"Just lie here and be still. I'll hold you. Just relax. You can get through this."

Jim lay still, preparing his mind and body for what was about to happen. He was about to get fucked. From a drawer in a bedside table Dean retrieved a bottle of lube.

"Lube us up Lisa," Dean said from where he was standing beside the bed.

Lisa quickly knelt beside him and lubricated his cock. She stroked him to a firm erection and then moved onto the bed behind Jim. Emily massaged and spread Jim's buttocks.

"Relax dear, everything is going to be fine."

Jim felt his wife's hand on his ass as she first rimmed his anus with lubricant and then worked first one then two fingers into his hole. Lisa probed just to her second knuckle and then rubbed around the outside again. Finally she pushed a generous amount of gel into his still tight anus.

"Listen to Emily honey. You've got to relax," Lisa coached her husband.

"Pull you knees forward honey. You need to give Dean better access," Emily said softly.

Jim had the feeling she was genuinely trying to help him and yet at the same time assist her husband in carrying out their intentions.

Now Jim could feel Dean moving closer behind him, his hairy thighs pressing on his ass. He knew Dean was preparing to mount him and he felt Dean's hand reach between his legs and grasp his balls. In surprise he looked to Lisa to find her watching Dean grip his nuts. He had never been handled by a man. Turning further he looked over his shoulder at Dean who used that moment to give his testicles a firm squeeze. Like Emily, Dean relaxed his grip and then firmly squeezed again – this time holding his grip. Jim met his eyes and with a couple of nods of his head acknowledged his submission and vulnerability. When Dean released him, Emily pulled him to her for a kiss. He then felt the fat head of Dean's cock pressing against his ass hole. Emily opened his cheeks wider to aid her husband's entry.

"Just relax and accept what's coming."

Lisa was not at all concerned about Dean's handling of her husband's balls or that he was going to take him in the ass. To her this was nothing more than a little dominance game the Taggs had worked out for their own entertainment. They were fully entitled to use Jim this way even if his introduction to anal sex was going to be a bit uncomfortable. She was sure he would get through it and if he could relax, may even enjoy it. She was certainly enjoying the turnabout. She didn't want her husband to be subjected to any extreme pain, but she wanted him to know that being sexually dominated sometimes came with some shame and discomfort.

Dean put his hand on Jim's back and pushed his cock a little bit further. Emily felt Jim's cock twitch and grow harder, nestled in her warm pussy.

"I felt that Jim. Exciting isn't it. Lisa, your hubby is hard as steel."

Dean pushed his cock head into Jim's tight rim. Jim gasped with the pain. Emily saw it on his face. She tilted her hips up and sought contact with her clit. Once in the right position she was able to hunch her clit on Jim's pubic bone.

Jim tried to relax. He felt his anus being stretched again. Dean was becoming more insistent with his probing. Within a few seconds Dean pushed his cock head past Jim's rim and paused. Jim was still panting with the discomfort. His ass was on fire. Lisa saw sweat break out on his back. She certainly knew the feeling. Jim looked down at Emily.

Again Emily saw him wince in pain. She grabbed his ass and pulled him closer now, hunching her clit on him for all she was worth. Her pants and soft cries got everyone's attention. She was about to climax as Jim was experiencing his initiation, his first anal penetration. Again Jim grunted in pain as Dean forced his cock deeper. That did it for Emily.

"Ahhhhhh!" she cried out as she ground her clit into Jim, clenching and relaxing her vagina and anus as she enjoyed her release. This made Jim's cock harder but did nothing for his effort to relax his anus.

Lisa tried to sooth him.

"Easy honey, you can take it. Just relax. Push back. Just like you told me the first time you took my ass."

Jim though about his own wife taking this same cock several times in the past with no comment to him afterwards about any difficulty. Now in past the rim, Dean took Jim fully, burying his entire length in his ass in a half a dozen strokes. In a moment Jim let out an involuntary "ahhhhhh!" The others smiled. They knew he was starting to experience the pleasure of anal sex. With all the lubrication Lisa had used, Dean's cock slid in and out with ease. Dean gave him a few long strokes. Jim responded by hiking his ass further up. This had the effect of pushing his cock into the back of Emily's vagina which suited her just fine.

Emily and Jim had locked eyes. She saw the newfound pleasure Jim was experiencing written all over his face.

"Good, isn't it?" she asked.

"Damn good," was Jim's reply and he relaxed himself further to enjoy the intense feeling of Dean's cock sliding in and out of his ass.

Dean picked up the pace. His balls slapped against Jim's as he fucked him harder and harder. Jim felt Dean's thighs against his. He was startled for a moment when Dean grabbed his hips, pushed him into a lower position and then pulled him back as he thrust forward. Jim had dominated Lisa that way many times. Jim felt shame having a man dominate him to the point of positioning his ass for fucking. On each stroke Dean drove Jim's cock into Emily's pussy. Soon this Executive stud was really pounding his cock into Jim's ass, causing Jim to push his cock deeper into Emily.

Just for fun, a couple of times Dean pulled his big head all the way out showing Lisa the open hole he had made of her husband's anus. Each time he thrust it all the way back in again, giving himself and Jim an intense sexual sensation.