Executive Privilege Ch. 08

Leon served his wife and Clinton refreshed cocktails. Emma saw her husband looking at her upper thighs and Clinton's semi turgid penis. Both glistened with the mixed body fluids of their copulation. Intuitively, Emma sensed jealousy in her husband. Understandable, but an issue they had discussed at length before accepting the arrangement. She had just consummated her relationship with Clinton and thoroughly enjoyed it. It ended as natural mating acts do with sperm deep inside the female. Her husband chose to stay and watch. Now he faced his sexually satisfied wife and her lover with his wet manhood fresh from her inseminated pussy. This is their new reality. This is what it looks like. Unless her husband got a grip, he could undermine their joint efforts.

The conversation turned to the mano a mano activity. Leon was visibly nervous and embarrassed. Clinton tried to take the edge off, "Every man in the arrangement has done the mano thing including me and Jamie. Sure, it's humiliating but it beats the alternative. You jerked yourself off. It's no different than an adolescent circle jerk. Nothing to be ashamed of." He had no sooner finished his understanding comment when Emma varted out a glob of his semen which ran down her thigh. They all laughed. Except Leon. Yup. Emma knew she had some work to do with her husband back home.

With that Clinton, Lisa and Jim departed to their adjoining suite.

Clinton was still lost in thought over Emma. Jim's straining erection was obvious. He was finished with her for the night; might as well let Jim use his own wife. "If you guys want a few minutes together go ahead. Meet me in bed, Lisa," Clinton offered.

In Jim's adjacent room, Lisa embraced her husband resting her head on his shoulder. "I love you, Jim and I'm glad Emma helped you get off. I completely understand. I certainly got off big time with Jamie." Lisa said with smile of reassurance to her loving husband. She knew from experience what he wanted now.

"Come to bed with me, darling," she gently said as she dimmed the lights and moved to his bed. As he approached, she spread her legs. Her hair was wet and matted, her hole red and oozing Jamie's semen. Her husband's pubic hair was wet, as well, soaked with Leon's semen. This would be an extra messy one. After their first year in the arrangement, this is the way they usually finished date night. They both enjoyed it immensely. Unfortunately, tonight they didn't have the luxury of taking their time. Playing on his prior experiences and his libido, she'd provoke him to a quick orgasm. Tonight, she was grateful their intercourse would not be prolonged.

As Jamie enjoyed his cocktail, he was becoming aroused just looking at Emma. "Except for that half-ass blow job, you've done well for your self today, Emma, and for your husband. I'm going to finish off in your ass. Hubby will prep you."

Emma's afterglow with Clinton was shattered. She now faced her only fear of this weekend in Jamie's bed. She was small and he was thick. She was experienced with anal sex and it could work, or she could be hurt; physically injured. She looked to his groin only to see he was already aroused. Jamie was her husband's boss. "Full service" expressly included anal sex.

"Emma, on the bed, ass up, shoulders down," Jamie instructed.

"Jamie, please not my ass. Fuck my cunt. Fuck my face. I'm ready to fuck right now. Please fuck me, Jamie," she pleaded in front of her husband.

"This can go down easy or hard. Let's try it the easy way first," he firmly replied. "Now, get in position you fucking whore." It was a sharp reminder of the status she had claimed this very afternoon.

Emma was comfortable with her sexuality. She and Leon enjoyed anal sex for their mutual pleasure. She experienced some of her most intense orgasms during anal sex; orgasms she had when he rimmed her, when he penetrated with just the head of his cock; when he let her fuck herself at her own pace; and ... when he took full control and possession of her. Of course, the difference she was facing here was size. Leon was as long as Jamie but, average in girth. After some a little preparation and a push, Leon slid right in. She could only hope Jamie would at least give her a chance and not rape her.

She was cornered and she knew it.

Emma moved to the part of the bed where just a short time ago Clinton had made love to her. Maybe this space would provide some comfort for what was coming. Her breasts hung heavy beneath her as she settled into position submissively presenting her anus and vulva to the dominant male.

Her svelte body, slim waist and flaring hips incited his lust. The bitch still bore the marks of the beating he had given her earlier. His cock stiffened in anticipation as he drank in the sight of her red ass cheeks, vulva and the hottest tightest hole a woman possessed.

Turning to Leon, "Give her a thorough rimming. After you rim her, stretch her out with your fingers. This won't go well if the bitch isn't relaxed and that's your job, Leon. Now get on with it. I'll be watching you the whole way."

Setting aside Jamie's crude, demeaning language, Emma smiled inwardly. Little did Jamie know but she and Leon usually commenced their anal sex sessions with analingus. Of course, she was always fresh and clean for her husband. Tonight, she knew she was a complete mess down there. Oh, well. There was nothing she could do about that. He'd just have to deal with it.

Leon approached his wife's ass. She had been beaten, masturbated, eaten out and fucked twice. Her genitals were red and gooey. It was humiliating to clean up another man's mess even more so while preparing his wife for anal sex with yet another man.

He stroked her back to relax her. He loved her small butt. She was perfect to him. Kneeling behind her he kissed her enflamed cheeks. He inhaled her familiar after sex essence and the distinct scent of fresh of semen; Clinton Santini's. He stayed away from her pussy as much as he could and instead ran his tongue along her perineum and the crack of her ass. He soothed her and unavoidably took in the slimy products of her recent intimacy. He lifted her by her hips raising her ass higher and then circled her anus with his tongue.

"Thank you, baby," said Emma quietly encouraging him. She thought to herself, he's taking this a lot better than he responded to her intercourse with Clinton. She knew in her heart he was swallowing his pride to help her through what Jamie was demanding.

He nibbled her pucker and then used broad strokes across her hole. In this position, his chin was bathed in the mess from her pussy. Knowing she needed all the help she could get to prepare herself for Jamie, Emma reached back and spread her own cheeks.

"That's right, baby, we're in this together," Leon responded with approval. He pressed his mouth over her hole and sucked it. He rolled the edges of his tongue up and used it as a miniature, flexible penis, to fuck her ass now past her inner sphincter. He fucked his tongue in, out and around the furrow between her inner and outer sphincter muscle. Leon loved eating his wife's ass almost as much as he loved it when she ate his.

He pushed his tongue as far as he could into her anus. His cock was swelling to full erection; his arousal flamed by memories of the pleasures of anal intercourse with his beautiful wife; pleasures that would be enjoyed by another man tonight. As he was rimming her, he felt her anus soften and relax.

"Good work," Jamie snidely commented as he settled into the leather divan in the corner of the bedroom. "Go ahead, stretch her out. Glad to see you're enjoying your work."

In the adjacent suite, Jim moved between his wife's legs looking at Jamie's cum mixed with her juices leaking from her hole, in her hair, on the inside of her thighs and glistening on her anus. There was more in her pussy; her whored out pussy. For money he had pimped her out to his superiors. And now, his erection straining, he faced the left overs of what the dominant males had taken.

For Lisa sex with her husband after mating with another man was sublime. Part of it is the physical sensation of his penis moving in her vagina loaded with semen. Part of it is the emotional impact of her husband stirring up another man's sperm as he reclaims her and takes his pleasure inside her body.

He ran his cockhead up and down her gash, wetting it with the slimy goo Jamie and his wife had made. He mounted her and started slow strokes experiencing the sensations of his cock sliding through his wife's slackened vagina slick with his superior's sperm and her excretions. Beyond the physical sensations he had his own emotional feelings, especially after Kevin Darcy or Jamie had fucked her. He knew their big cocks triggered her excitement. Those two pleasured her in way he could never do with his average male endowment.

Tonight he'd seen it up close and personal. His wife lusted for his superior's big dick. His boss had taken the usual snugness of her vagina for himself leaving her so sloppy and loose he could hardly feel her sheath.

"Come on, Jim, it's your turn. Fuck me. Jamie fucked me so good. You saw him reaming me, filling me with his cum. You know we both like this part a lot, but this time we haven't got all night. Your boss is expecting me in bed," Lisa urged him on as his cock drove in and out of her well used vagina, "He might want another fuck for himself."

Driven by his own excitement, he thrust into her harder and faster. She stoked her husband's lust, "That's it, baby. Fuck me like you paid for it. Fuck me like you're going to fuck Emma."

He was trying, but he could barely feel her cunt. His mind flashed back to the sight of Clinton standing behind Emma, fondling her breasts and nipples with his dick between her legs, crimson head protruding, dripping with her juices, dripping his pre cum and Emma displaying her own erection to him while rocking her hips and sliding her wet slit back and forth along the top of Clinton's erection. Imagining he was mating with Emma, he ejaculated into his loving wife adding his semen to the sperm she already carried.

Lisa hardly felt it. She stroked his hair for a few moments then kissed her husband goodnight, "Sorry, honey, I've got to go." It was an abrupt departure but they both understood. They had taken Clinton's favor. Now she was due back to him. She headed for her shower and then to bed with Clinton.

Jim's shame and jealousy were tempered by a high degree of satisfaction. He had enjoyed the lustful after dinner activities; especially watching Leon's gorgeous wife have sex with Clinton. At home, he would be all over his wife to work out a swap night with Emma and Leon. Mano a mano and sloppy seconds sucked as erotic experiences but, he got off. Back home, whether it was a date night for Lisa or not, sex with his beautiful wife had never been better.

He also felt good about his contribution to the Company. He worked hard and handled their participation in the arrangement like a man. For the money they were being paid, they were winners. The arrangement was working out for them. Fucking Emma would be icing on the cake.

Back in Jamie's suite, Leon lubed up his index finger and inserted the tip; first through Emma's outer ring and then through her inner sphincter. It's the inner ring that's pain sensitive. He knew this is where his wife would be struggling. He then inserted and rotated two fingers, pressing all the way in ... then three. He thoroughly lubed her inside and out.

When Emma felt, her husband move his thumbs to her anus, she took a deep breath. Leon gently spread her ass. "Ouch," she warned.

He slowed his ministration not looking at Jamie, hoping Jamie would not rush them through this part. Again, he applied more lube and used his thumbs to stretch her gently. He knew she could only take so much and he didn't have time enough to size her for his boss's dick. She'd have to do the last part all by herself.

On his knees, Jamie approached them fully erect. "OK, that's enough. Now, lube me up," he instructed Leon.

"Wait. Wait," Emma interjected. "Let me get you ready. It's my job. Besides, I want your big cock in my ass. I want you to fuck my ass, Jamie."

Whoa!!

Both men were taken by surprise. Emma wanted to get butt fucked by Jamie? At best, it would be painful and they all knew it. Neither man suspected Emma was about to take a calculated risk. A calculation only a woman could make. A risk only a woman could take.

"Sure, you can lube my cock, Emma" Jamie's tersely replied, "Go to your room, Leon, and don't come out till morning - no matter what you hear."

Leon had confidence in his young wife. She was smart, beautiful, fit, and had a feminine intuition and cunning he had come to respect. His stomach was churning. He had no choice. He had to leave her to her fate as his boss's whore.

On her knees, Emma turned to Jamie. She moved close. Close enough to rub her tits on his chest, to feel his chubby belly on hers, to take his cock in her hand, to breathe into his face.

Locking his eyes, "You've had my mouth and my tight cunt and now you're going to have the tightest ass you've ever taken. There'll be some pain, but I'm going to push through it and take it like a woman. I'm going to make this good for you, Jamie - very, very good for you. Here's how we're going to do it.

I'm going to crouch down. You're going to slowly work only the head of your penis between my inner and outer sphincters and dock your rim between the two, directly in the furrow." She fingered the rim of the head of his penis to reinforce her explanation.

"Now ease the tip of your index finger into my ass and feel for the furrow." He did. "Perfect. I'm sure I'll make some noise as you get there but, once you're in place, we'll party with your frenulum." Emma fingered the fold of skin on the underside of his penis where the head connects to the shaft, that special spot on the underside of his crown where the nerve endings are concentrated. Jamie's breathing became more shallow.

"That's right Jamie. That's the place you go when you masturbate. It's the place you want tongued when you get head. You might come right there. Leon loves to come there."

"I sure fucking hope you do, you asshole," Emma thought to herself.

"When we're ready, you'll push your rim through my inner sphincter and stop and I mean fucking stop. This is going to be hard on me, Jamie, but very tight and very pleasurable for you. If you haven't already come, once I'm adjusted, you can fuck my ass."

She moved his hands to her tits. "Feel me up, Jamie. Pinch my nipples. Squeeze my ass. Good. Bite my nipples. Come on, man, feel up your whore. You're getting ready to fuck the tightest piece tail you've ever had."

Emma lowered herself to her elbows and pulled his dick to her mouth. Looking him in the eyes she wet her lips, made an "O" and slowly pushed down till the rim of his cock was just inside her lips. She squeezed her lips hard and whipped his frenulum with her tongue. Jamie gasped. He got the point of her object lesson.

She took her time using plenty of lube on his dick firmly masturbating his frenulum. As she rubbed the spot she caught his eye, "Right here, Jamie. When you're in my ass, this is where the action is for you."

Emma could only hope her psychological and physical preparation of Jamie would pay off as she turned and put shoulders on the bed and knees in a low crouch. With her weight on her shoulders she reached behind and pulled her bottom cheeks wide in a shameless offering of her most personal orifice for the fucking that was coming. She knew this vulgar man was fully capable of ignoring all her efforts and turning consensual sodomy into rape. She also knew this could not be a repeat of her failure to provide him the satisfaction he sought. She couldn't take another beating tonight.

Her golden marital rings, the gold claps of her red collar and her red ass added to his excitement of her offering. The dominant male moved in to mount her. With a jolt she felt his mushroom head press against her wet anus. She looked back to him and confirmed her submission. "I'm ready." Emma knew she had to keep her head in the game. She took slow deep breaths, relaxed her anus and took a strain on her bowels.

He pushed his cock head firmly against her prepared asshole; then harder as he pressed through her taunt hole further into her inner sphincter driving about an inch of his cock head into her. The head of his cock was now lodged halfway into Emma's asshole.

"OOOOWWWW!!! ... STOP! ... THAT'S HURTING MY ASS ... Please stop! Let me adjust," Emma shrieked as his thick head dilated her inner muscle ring.

Her cry of pain was heard throughout the suites. Lisa felt Clinton startle. Visibly upset, he got out of bed and picked up his slacks. "Clinton, you shouldn't go in there. She's getting ass fucked. Big deal. Jamie's not doing anything wrong," Lisa said, not understanding why he was upset. He turned to her with a sigh and lay back down beside her.

Jamie paused. Breathing deeply, Emma took a harder strain trying to open herself up. "Jamie this hurts, but try to push your rim into my furrow," she sobbed, knowing she had to make some progress or things could get badly out of control.

Jamie renewed the pressure and drove further into her, feeling his rim set in her furrow. The feeling was exquisite. His entire glans was now inside the young woman. He groaned in pleasure.

Not so much for Emma. As her inner sphincter was further widened, piercing pain followed.

"AAAAAHHHH ... STOP!!! ... Don't move," she bawled.

The pain was unavoidable and she knew it. If she had time to adjust to this wide penis, she'd be ok. If not, she was going to get hurt. She was determined to get through it her way.

Emma emitted a low groan getting her pain under control. She looked back at Jamie, "Let's party. Fuck your special spot on my outer ring. Have some fun, but don't pull out and push in a little more on each stroke." She felt him start his fuck and heard his groans of decadent pleasure.

Jamie had never done this before. He usually just pushed though, ignored the noise and got on with ass fucking the bitch. But this felt great. "Oh, this is so fucking good, Emma, just like you said," he admitted.

"Well, if it's that fucking good, go ahead and cum you fucking bastard," she thought to herself. He might cum from this. Leon often did. This was one her husband's favorite fuck spots.

"I'm ready to fuck now, Emma," Jamie said as he pressed forward.

"OK Jamie, slow down. Give me a slow steady push and then stop when your head pushes all the way through," she responded. Emma knew what she was doing. She was in control. Kinda. Ready to get this last push behind her, so to speak.

He pushed forward and grunted with the effort. She felt his broad rim pushing through her inner sphincter and the return of the knifing pain. Suddenly, the head of popped in past her inner sphincter.

"Now fucking STOP! ... Just stop ... give me a moment to adjust," she panted and took the pain. This was the final dilation. She knew this would pass. So far, her plan was a success.

This was the tightest ass he had ever been in. She was constricting his cock right behind his rim. He now had over two inches of his dick in her ass and he was primed to give her the rest.

Her pain diminished to an occasional sharp twinge and her ragged breathing started to settle.

Jamie held her hips and felt her muscles start to relax. Emma knew she had to get on with it. She rose to crouch on her elbows and looked behind to him, "Ok. You can fuck me now."

He began to steadily force his cock inch by inch into her body. He used a rocking motion that did not involve withdrawal only a relentless push to fully impale the female on his shaft.