📚 that was always the plan Part 9 of 9
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That Was Always The Plan Ch 09

That Was Always The Plan Ch 09

by thegameoffuc
19 min read
4.22 (5900 views)
adultfiction

Dear readers, I would like to thank Literotica user and editor Skye Kahoali'I for their help in editing this story. I am a new and amateur writer and without their time and effort, it would not have been possible to bring this story to you guys.

This is the final concluding chapter in the tale of Jim. Please leave your comments on how you all liked the story. I am planning two bonus chapters if you all would like to read them. Do let me know if I should add those chapters. Comments and feedback are as always, welcome.

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Jim bought a bottle of Scotch and a six pack to celebrate. He was ecstatic. Not only was he now extremely rich and an owner of a fast-growing organization, he'd also had his revenge on Henry. Henry had been utterly humiliated, and though currently he had money, Jim would ensure that Julie, his wife, sucked out every single penny from him in her divorce settlement.

Jim could not wait, so he broke into the six pack. He'd also got to fuck Henry's virgin eighteen-year-old daughter which was like the cherry on the cake. It had been a really long day, but he had one more promise to fulfill. He was already outside her door about to ring the bell.

As Tiffany opened the door, she was surprised to see Jim standing at the door grinning goofily with a bottle of a very expensive scotch in his hand. Jim looked very different from his usual suave self. He looked hammered, and vulnerable.

Jim checked Tiffany out, too. She was wearing a short bath robe which covered everything from her neck to her thighs. It had a cloth belt tied in front to keep the two sides in place.

"May I come in, or are you busy with other guests?"

She smiled at him, "Lucky for you that tonight is one of the few nights I had no plans." She could smell alcohol on his breath and guessed that he'd had much more to drink than usual. She invited him in and brought him in to the living room of her new penthouse. Jim sat on the sofa, grinning foolishly. Tiffany felt anxious. If his plan had failed, both their necks would have been on the line. She had signed over all her shares in the company to him for free, and here he was, hammered like a fucking teenager, grinning as if he didn't have a care in the world.

"How did your plan go?" she asked nervously.

"Fucking brilliant.... You should have seen the look on Henry's face when he realized that he was fucking destroyed. Better still, you should have seen how fucking big his shit hole had gotten after his wife had drilled his ass raw."

Tiffany winced. Jim's voice was too loud, too exuberant. She was not used to hearing Jim talk so loosely. He was usually much more mature and in control of himself and the situation always. She realized he was really very drunk, just like a college kid. It hit her that though Jim usually acted with much more maturity, just how very young he still was. She smiled to herself.

"Would you like something to drink?"

"Yes, please! I want a pitcher of beer if you have one and anything else that I can get drunk on."

She got up and went in to the kitchen to make the right drink for him. She could hear him singing a very loud and out of tune version of Michael Jackson's 'Beat It'. She laughed out loud; he certainly seemed to be out of his mind.

As she came out with their drinks, she was shocked to see the scene in front of her eyes. Jim had removed most all of his clothes. He had thrown his clothes here and there on the floor. All, except his tie and socks. His tie was on his head, looped around his forehead. His underwear had fallen at his feet. He himself was seated on the sofa, almost naked, playing an imaginary drum set with imaginary sticks. In between lyrics he would stroke his cock, and then continue to sing and play his drums. As he saw what drinks she put on the table, he looked at her belligerently.

"What the fuck is

this,

woman?! I specifically asked for

beer

." he shouted.

She was torn between anger and laughter. She felt a little like someone in charge of an unruly teenager who was under her care.

"It's called 'coffee' and I think you need it. Now, shut the fuck up and drink it quietly."

That sobered him a little and burst his happy balloon. He took a mug and began drinking his coffee quietly. She too, sipped her coffee silently. Slowly she felt him coming back to Earth. His expressions changed slowly as his head began to clear up a little. Tiffany was still watching him intently and did not break the silence.

"Sorry, Tiffany. I guess I had too much to drink but it has been that kind of a day. Everything went as per plan. I was so nervous, but it went without a hitch. I own the damn place now. I have thrown out all the fucking incompetent fools. I also think I will quit my job tomorrow," he finally gushed out. She was surprised, she had thought he would become the new CEO.

"Kudos. You'd better find a new competent CEO if you are not planning to be at the Helm."

"I have found one. The very best one." He smiled at her and removed the last envelope for the day and handed it to her. She took the letter and began reading it. Her eyes widened. She was shocked.

"Congratulations on your promotion, Madam CEO. Effective today 3:30pm you are the new CEO. I have also returned the six percent shares you held before signing them over to me. I have added another twenty percent to it and you will also get a substantial raise in your salary."

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Jim was surprised to see disappointment in her face. Then she got angry. Keeping her temper in check she said, "Why Jim? What have I done to deserve this? Am I that great a fuck? You think I deserve being the CEO because we are fuck buddies?"

Jim was scandalized. He said "No...No...No.... You truly deserve being the CEO based on your competency. It has nothing to do with anything we may have on the side. I have never traded

careers, money, or promotions for sex. I own the company. All my wealth is invested in it. I wouldn't make a decision to make you the CEO unless I knew you could handle it."

Tiffany was still skeptical and kept silently fuming.

It was imperative that Tiffany understand why Jim took this decision, else she would never believe in her own abilities. Jim told himself that he had to convince her, whatever it took. He took a deep breath and said, "Believe me I have followed you and your career for three years now. You have the ability to take this company right to the top. Making you the CEO has nothing to do with me wanting to have sex with you. To prove my point, I promise you that were you to accept this position I will never again desire to fuck you or have any relationship with you except a cordial and professional one."

His voice cracked with emotion. She could hear his sincerity and the effort he had to make to bring himself to say this. She smiled. How could she remain angry with him? He completed her.

"I will accept the position on one condition...." she said.

He did not hesitate even for a second, "Name it."

"I accept the salary but along with that, I will need to be satisfied in kind too, at least once a month."

Jim smiled, walked over and sat in her lap. He began kissing her on her lips and she kissed him back with equal gusto.

"There is one more thing actually," Jim said breaking the kiss. He took a deep breath and continued.

"Through my college days I always liked to be in control of all I did. When I flirted, I was in control. When I courted a girl, I was in control. When I fucked all my girls, I was always the one in control. This continued to happen even in the office. These last so many years I have been plotting and scheming. I have been putting in efforts and working towards this day. I have never let myself be free. I haven't let go of the control. I have never been in someone else's control and just sat back and enjoyed. Now, I don't think I can even do that, but I want to try. Only with you Tiffany can I be that carefree college kid. Do whatever you want to me. I am all yours tonight."

'He was a kid after all,' she thought. She was moved by his confidence in her. She removed the tie from his head and looking into his eyes said,

"So, Jim, you do realize that currently, I am the CEO and you have not quit the company. So, technically you report to me and it is my discretion about what to do with you. I have decided that I... I mean the company, will not let you go until I... that is to say, the CEO is completed satisfied with your work."

While she was talking, Jim did not notice that she had wrapped the tie around both his wrists. She slipped and knotted the tie, tying both his hands together. Jim smiled.

"Yes Ma'am." Jim said. Tiffany got up and walked to her bedroom pulling the tie and dragging him behind her like a pet.

"Down on your knees." She told him, and he went down on his knees to follow her. She took him inside the bedroom tied him to the headboard. Jim was now tied naked to the bed. She opened her belt and let the gown fall. Tiffany was wearing a red satin bra and thong set. A hungry look came into Jim's eyes. He had seen her naked many times now, but he still loved to look at her body. The bra was quite skimpy, amply showing off her luscious cleavage. The thong was little more than string and a triangular swatch of red satin, which left hardly anything to the imagination. His eyes hungrily ravished her, his eyes bored into her features, her lips, her flat stomach, each of her amazing curves, her flowing hair as she let it down. His cock stood up erect and raring to go. She blushed because no one made her feel so beautiful and sexy except him. She felt a tinge of wetness as her pussy came to life. She jumped on the bed and grabbed his cock roughly. She gripped it tightly, almost painfully, and squeezed--digging her nails in.

"You are a fucking naughty, dirty, common mongrel. I am going to teach you some manners today." She opened the bedside drawer and removed a dildo shaped vibrator. She switched it on ran it across his chest. Jim had never been in such a position. He was very ticklish and squirmed under her teasing. In a swift motion she put one of her legs around his body and brought her crotch in front of his mouth.

"Start licking...like a good doggie." Jim didn't need to be told twice. Her camel toe was smooth and bare. He stretched his tongue and tried to touch her pussy, but she pulled her crotch back a little. He bent his neck forward, but she went further still.

"You have forgotten the magic word."

"Please! M-M-Mayyyyy I?" He stuttered as he felt the vibrator on his cock. It was a sensation completely new to him. With one hand, she was rubbing the vibrator all around his cock with the other she grabbed his hair and pushed his mouth into her sex and held it there. He began licking her in earnest. He touched all her right spots and got her moaning in seconds.

"Ummm...ummmm...ummmmm," she moaned. As she kept rubbing the vibrator on Jim's cock and balls, he had trouble holding back his orgasm and focus on servicing her pussy. He was going to cum.

"You'd better not fucking cum without my permission. Make me cum first, you dog!" She told him. Jim increased the pace of his licking. He pushed inside her pussy and she was screaming in delight.

"Ummm...aaahhh. Aaaahhhh.... Fuuuckkk...fuuuuccckkkk...don't you dare slow down...lick it...lick me...aaaahhhhh...aaaahhhh." She kept pushing her crotch into his mouth to get his tongue farther inside her pussy. He felt her tense and knew her orgasm was close. He increased his pace further.

"Unhh. Unnhhh.... I'm cumming...." she cried out and she did...cuming hard right on his face. Her hands went limp as her orgasm rocked her pussy. She fell over his face, leaning on the headboard and panting. As her breathing stabilized, she could hear his voice muffled by her still spasming pussy.

"Mayyyydiedummmm???"

She lifted her hips up. "May I cum, pleeeeeease?"

"No, not yet." She kept rubbing the vibrator on his cock. Jim was squirming desperately now. This was painful for him. His balls were hurting but she continued to torment him. She turned, bent down and brought her face near his groin. She opened her mouth.

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"You may cum now..." she said just as she brought the vibrator tip right to the tip of his cock. His over-stimulated cock exploded with pain and pleasure. His balls contracted and as he climaxed, he shot a load straight into her eagerly waiting mouth. As his cock continued to shake and shoot string after string of cum, he got the gooey mess all over her face. She stood up and looked amazingly hot. She swirled his cum in her mouth before swallowing. She even picked up everything from her face and licked it off her fingers. She grabbed his cock again and squeezed it till the last drop and sucked it off her fingers, lost in oblivion. She looked hot as hell.

Jim's cock had finally gone limp. Tiffany took out a whip from her drawer and grinned as she bent it to check its flexibility.

"Your cock better not bail out on me." she warned as she cracked the whip on his thigh. The first stroke was not gentle but had a teasing pain with it. Jim was on the receiving end of the hurt for the first time. The pain was stingy but not bad. She kept whipping his thighs and chest alternatively. Then without warning she smacked one right on his limp cock.

'Ouch!" he yelped in pain. His eyes watered. She waited for a few seconds and smacked him again...and again...and again. First on his shaft, then his balls, and then back on his cock. They were light, almost gentle strokes not meant to cause pain but just to arouse his sleeping cock. Quite different from what he himself would have done. Soon, Jim's cock began to harden again. Tiffany jumped back on him. Jim was sitting with his back against the headboard with his arms stretched and tied behind. She was on him and removed her bra in a flash. Jim could again see her gorgeous naked boobs

He had fallen in love with them in the first minute he had seen them. They were large but firm and the beautiful pink nipples were staring him straight in his eyes. The only thing he could do, seeing them, was to take them in his mouth and suck them.

"Please, may I suck on them?"

She flicked her hand behind her back and smacked the whip on his balls as she said, "Yes you may, and you better do a thorough job." She put one of her boobs into his salivating mouth. He hungrily sucked on it, trying to get in as much flesh as possible. He played with her nipple with his tongue licking and flicking it. Moaning loudly, Tiffany lowered herself on his shaft. She was still very wet from her previous orgasm and it slid all the way in, impaling her on his rock-hardness. Her eyes closed, and guttural moans escaped her thickly.

"Aaaahhhh.... Ummm...aaahhhh...." she grabbed his hair and guided his mouth to her other nipple. Jim ate it with gusto. With her other hand she kept whipping his balls and then began jumping up and down on his cock as if riding.

"Ummmm...ummmm.... Unghhh.... Unnnghhh...." she moaned as she plunged herself repeatedly on his cock. Her breasts jiggled, smothering Jim's face between them. Soon she was close to another orgasm.

"Ummm.... I'm...going.... Ummmm...to...ungggghhh...cumm...unghhh...when I dooo...mmmm...unnnnhhhh...cumm.... Ummmm...with...me...." she quickened her pace smacking her ass on his balls, slapping them greedily.

Both of them came simultaneously. His balls tightened, and he shot another load deep in her womb. As stream after stream of cum painted her pussy walls, she orgasmed like never before. Her body shuddered as a tsunami-wave of climax hit her. She collapsed on his chest panting, enjoying her orgasmic afterglow. He felt amazing and in a daze as his body, tired from all the fucking he had done already, tried to blackout. He felt her remove his bonds and his hands fell limply to his sides. He had no energy left and was panting with deep, panting breaths. He could feel her rising and falling over his chest as he tried to calm his breath down. Tiffany began kissing him again and whispered,

"Did you like it?"

"I could get used to it," Jim said grabbing her into a hug and kissing her deeply. He was tired, and all he wanted to do was cuddle and sleep, but Tiffany had other ideas.

"You haven't forgotten your promise, have you?" she asked with arched eyebrows.

"Of course not! How can I?" Jim said. In a second Jim was back in control and his old self. Composed and calm.

"You forgot the magic words!" He smiled at her.

"Please...please...woof...woof"

"Suck my dick, make it hard!" he ordered her, turning the tables. She took up the change in stride, enjoying the fact that she was not in control anymore. She bent down and took his cock in her mouth. She could taste his cum amd her pussy on it. It smelled of sweet-sourness and pungency and fueled her on-again arousal. She breathed deeply, enjoying the aroma of sex. She put enough spittle on his cock then had a different idea. She grabbed both her succulent mounds and held them together. In the seam between them she slid his wet cock. She was lying awkwardly and didn't have enough leverage to fuck his cock properly, but she did manage to slide up and down a few inches. The wet cock slid between her generous melons with just enough friction. She could feel it hardening once more and throbbing. She drooled more spit and bent her neck to lick the tip. Jim enjoyed it with his eyes closed. As he got harder and wetter, he grabbed Tiffany's hair and pulled her face up, mouth wet and dripping with saliva and looked into her eyes.

"On your fours... turn around now..."

She turned, and he saw her glorious ass cheeks staring straight into his face. He spread her cheeks to discover her tiny brown hole, hardly big enough to let his finger slide in. He spit on her hole and began stroking her with his middle finger to make her asshole wetter.

"Unnhhh.... Doesn't hurt as much as I thought It would...it doesn't feel too bad." She said, moving back and forth in a rhythm stroking herself.

"That's just my finger." Jim said. He could feel her literally freeze and tense up on his finger. He felt her anus clamp in terror.

"Tiffany, you can't back out now. Brace yourself, it will hurt but only in the beginning."

Saying that he put the head of his cock on her tiny hole. He pushed in, but her sphincter was closed. In her terror, she was resisting and making it difficult for herself.

"Relax...it will be easier if you do.... Trust me and leave it to me...Tiffany," Jim soothed. He put his hands on her shoulders and gripped her firmly, comforting her.

Her terror lessened, and she began to relax, and so did her muscles. He could push in the head of his cock slowly like a plunger and he pushed a bit harder, getting the whole head in. Using her saliva as lubrication, he pushed in his cock.

"Aaaaiiiiieeeeee...." screamed Tiffany as she felt his large cock bore into her ass. She had misjudged and was in pain, a lot of pain. Jim was going very slow on her, but his hands were firm. He impaled her on his cock. He enjoyed squirming girls and their pain turned him on. He knew he was not going to stop now. Tiffany was in a world of pain. Her bowels felt full as never before. Her terror returned, and she squeezed her hole closed, vising the cock in turn. Jim was enjoying her tiny, tight hole. It felt like a strong hand gripping his cock tightly and squeezing his cock. He kept up the pressure and soon he was balls deep in her ass. He pulled out and then mischievously pushed the entire length of his cock back in a single motion.

"Aaaaaiiiiieeeeee...! Fuck you, Jim...! Fuck you!" Tiffany screamed in her agony. He slapped her ass lightly and with one hand grabbed her hair.

"That's no way to talk to someone who can literally tear you apart!" Jim teased her.

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