That was Always the Plan Ch. 05

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.

We continue the story after the main characters come back from the Retreat. There are some new character introduction. Hope you guys like this chapter and my favorite character in this series. Please do write in the comments if you liked the series till now. Feedback on the stories, characters and my writing style are welcome as always.

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Jim's flight had just landed. He and his colleagues were just back from the annual summer retreat. The retreat, which had been eventful to say the least. He wished goodbye to everyone and waited for his taxi to arrive. He politely greeted both Tiffany and Chloe. His colleagues would never be able to guess that he had fucked both these beautiful ladies senseless, over and over again during the last three days. As Jim saw Tiffany sigh and get into a cab, he realized that her marriage was all but over. Chloe even walked a little funny. His taxi arrived, and he was about to get into it when he heard someone shout his name from behind. He turned to see the burly figure of Henry, the CEO of the organization walk towards him.

"Hey, Jim, hope you had a relaxing weekend?" Henry smirked and raised his eyebrows knowingly.

Henry had a rough drawly voice which matched his overweight body. He was in his fifties with a receding hairline. The hair was dyed jet black and the way he dressed himself made him look the boorish fool.

"It was quite uneventful!" Jim replied. He was tired, and Henry was the last person he wanted to talk to, right now.

"Oh! I thought I saw Chloe walking a little funny," Henry replied, grinning slyly.

Well at least he didn't know about Tiffany, Jim thought. Henry was known to make vulgar jokes about the females in the office. He had a very bad reputation among the ladies, and was an absolutely horrible CEO, since he'd never learned to be an effective manager. He had never openly flouted the policies of the organization or made advances on anyone. Most of the office folk thought he did not have the balls. Well, he may not have had the balls but that did not mean he did not dip his nib in the company ink. Jim, unfortunately, knew his secret and was an unwilling part of it.

Jim stared at Henry. Henry had joined their organization four years ago from a different company, directly as the CEO. He was a ruthless businessman and though Jim respected his business prowess, he despised him as a man. Henry spoke brashly in a crass manner to everyone, even women. For all his faults Jim was always respectful towards women except during his BDSM play, which is why he never discussed his escapades with anyone, much less Henry. Henry was known to fire employees for something as small as disagreeing with him. Over the years, most of the top positions in the company were filled up with his favorites and friends. In the last four years many of the deserving promotions, including Jim's, had been mysteriously delayed. Jim hated the guts of the man in front of him and really wanted to be on his way home.

"You need anything specific from me? My taxi is waiting," Jim said in a bored, tired sounding of voice.

Henry's fake smile vanished from his face. He narrowed his eyes and glared at Jim. Who did this idiot think he was talking to? Henry thought. If Henry wanted, Jim would be out of the company tomorrow. Out of a job. Jim knew he had hurt the man's inflated ego, but he couldn't care less.

"I am a busy man, Jim. I came over to talk to you about the other annual ritual we have every year. You know what we need you to do," Henry added handing a visiting card to Jim. Jim winced. He lowered his eyes to read the name on the card. As he read the card, his hands faltered, and he felt as if Henry has clubbed him in the head. It was Tiffany's visiting card. It was lucky that Jim was not looking at Henry as he read the card. His face would have completely given away his shock and anger. Henry giving him Tiffany's card could mean only one thing. Controlling his emotions and voice, he smiled at Henry.

"Branched out, have you? I thought you liked...umm.... Younger women? I would have thought she's too old for your liking." Jim probed, trying to find what was going on in his mind.

Jim wondered if Henry had found out about Tiffany and him getting together over the last few days. Was it Henry's way of intimidating Jim further? No! It was insane to think that Henry knew and even if he did, Henry surely did not know that Tiffany meant something more to Jim than his previous dates.

"You should fucking mind your own business! Go ahead and do your bit of...whatever you do...and get her ready! That's all you are good for.... And why we still keep you in Company."

Jim ignored the jab at his capabilities. It did not bother him. At this moment all he cared was an answer to the question: why Tiffany?

"I thought the things got a little out of hand last year. I thought I had requested to not be involved with this err...annual ritual...any further."

Henry's eyes bulged. He got angry and snapped, "You thought that, did you? Listen you little dipshit. I have always been kinder to you than you deserve. We have turned a blind eye to your wrongdoings. You keep your end of the bargain and I will keep you out of trouble," he shouted.

It was never a bargain; for Jim was not actually required to do anything that Henry asked him. There was no "understanding" between them, despite Henry's blandishments. Also, Jim did not need help from anyone for what he wanted to do, much less Henry.

"Suit yourself! I guess at your age and your stamina, you might not be able to keep up with the young girls," said Jim delicately.

Jim added the last statement deliberately knowing it would make Henry angrier. Henry's eyes widened. A vein popped on the older man's forehead and his face turned a livid shade of purple.

"You little fuck-weasel! Don't you dare take that fucking condescending tone with me. I am not a pansy like the previous CEO. You don't want to get on my wrong side or I will destroy your life. Just like that loudmouth Tiffany. She did not know what was good for her. Fucking slut. She's had this coming for her for some time now. So, shut up and do your work, if you know what's good for you. A very good day to you," huffed Henry. He turned around and left Jim holding the card.

Jim smiled. He got his answer and it was worth angering the idiot just to see him bluster. Tiffany must have rubbed him the wrong way. It was some personal vendetta. He had no idea about Tiffany and Jim at all. No matter, now it was personal for Jim too. He silently cursed Henry and his fucking contemptible behavior. Jim had simply wanted to go home and relax but no-o-o...Henry had dumped this on him. Sitting in the taxi, his mind kept whirling. Henry would have to pay for this, but Jim was not ready yet. He needed some time but by involving Tiffany, Henry had just nailed his own coffin. Jim knew he would have to act quickly, very quickly if he wanted to keep Tiffany safe and also achieve his plan.

"Crap!" He swore out loud. This was getting out of hand. He cursed the day he met Henry. Things had gone far enough since then. Jim knew if he helped Henry this year, then he would be complicit with him, and no longer an unwilling participant. Now that Henry had involved Tiffany, there was no question of Jim doing anything that Henry wanted. He had a long ride to ponder over this.

No one in the organization knew where his address was. He lived in a really posh villa in a very affluent suburb. He'd built a fortune becoming, richer than anyone in the organization, including Henry. He really didn't need to work at all. Of course, none of this was known to any of his colleagues or his bosses. They really had no idea about his wealth, status, or background. He liked to keep it that way.

He had a plan, but he wasn't sure if he was ready to implement it yet. One wrong move and he would play into the hands of Henry and get himself dismissed. He didn't much care about the pay but liked to have this job as a part of his life. Could he trust Tiffany? No, not yet, and anyways he couldn't risk getting her involved unless he was sure of victory. He could afford to be thrown out; she couldn't, especially if she was planning to get a divorce. He felt irritated. What was the matter with him? He felt frustration and anger getting the better of him. What was the matter with him? A minute later, he smiled as the answer to his current bodily need popped up in his head.

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Earlier in the morning, at The Mansion:

The girl woke up to her alarm at 6:30 am. She had been having a pleasant dream. As she uncurled and got up, she tidied her basket. The basket had a soft mattress and a pillow to sleep in. The room she was sleeping in was small, but very tidy as she had to keep it perfectly immaculate. Her Master hated it when anything was out of its place. Not that he visited her room often, but she loved keeping him happy.

She loved it when she pleased him because pleasing him enough would mean he spoke to her often, gave her belly rubs...he would even fuck her lovingly. She felt herself getting wet, just thinking of being fucked by her Master. He was always nice to her if she pleased him enough. Within a few days of her moving in with her Master, he'd gotten her the soft and small pet bed to sleep in. At first, she thought the basket was too cramped, and difficult to sleep in. When she realized all pets would sleep in such baskets and it pleased her Master so much, she simply learned to enjoy it too.

The girl remembered the date and immediately got very excited. It was the day when her Master came back home from a work trip. She did not like him being away from her for too long. She smiled, thinking about her Master fondly. Immediately, she realized the number of things she would have to do before his arrival. She needed to groom herself and make herself presentable for him. She loved making herself beautiful for him. She loved to look pretty everyday but when he came back after being away for a few days, she took extra care to look extra special for him. Not that it worked every time. Many a times her Master ignored her presence in the house. Sometimes, even after she made herself up to look as stunning as the models she saw in magazines, her Master wouldn't even look at her. At these times she hated herself for failing to please him enough. She knew she had to get better at serving his moods and desires.

She went to the bathroom. She looked at herself in the mirror, stretched and yawned. She saw beautiful green eyes stare back her under long tresses of wavy ginger hair. She was tall, about 6 feet and had a slim, almost lanky frame. She was wearing a satin bra with an underwire as she always did when her Master wasn't home. One of the first things he had taught her was to take care of her boobs for him. He didn't like his view of her breasts ever obstructed so she never wore a bra or a top when he was home. She did, however, need to keep them firm, perky, and taut for him so whenever he left for work or trips, she wore a bra with an underwire. She also worked out a lot with chest exercises to keep them firm and in shape, exactly as he liked them.

Thin though she was, she had absolutely natural knockers for boobs. Her bra size was 32DD and she was proud of her chest even before she had met Master. He had once told her that the only reason he let her live with him was her breasts and should they ever sag or drop, then she would have to find a new home or live in the street. Absolutely terrified, not of living on the street, but of having him discard her, she took exceptional care of her breasts and kept them firm, lifted and succulent.

Facing the mirror, she removed her bra and freed her boobs. They looked huge compared to her slender frame. She cupped them in her delicate hands. She had fair, creamy skin with a light scattering of freckles. Her areolas were large, pale-orange colored discs topped with darker buds in contrast to her fair skin. Her nipples stood almost an inch long when excited and pointed straight ahead. As she let them go, they wobbled seductively. She flashed herself a smile and picked up her toothbrush.

As she was brushing her teeth she stepped on her scale. She weighed herself daily. This was so she could maintain her figure at her ideal weight which her Master liked. Sometimes, he weighed her too, if he felt she wasn't maintaining herself properly. As she stood on the flat glass surface the readout showed 116 pounds. Oh, no! She panicked. She was a pound above her ideal weight. Master would be so displeased with her.

Her Master had to be very strict with her about her weight. It was her job to please him with her body. She ran her hand over her smooth, taut stomach. It was as lithely muscled as ever. She pinched her arms to see if there was any flab. Her arms were as delicate as ever, soft and supple. Then she pressed her cheeks to see if her face had become fat. She sucked in her cheeks and saw her enhanced jaw line. She had a good number of freckles on her face. She had hated them in college but when her Master said he liked them she was happy. She thought back, trying to remember how she had gained weight. She exercised daily per the regime set by her Master. He had also given her a strict diet sheet to follow. Of course, the choice of what she ate couldn't be left to herself! That would be stupid, she would have options of eating anything she wanted, even, chocolates, pastries, ice creams or sweets.

She had been a sweet-tooth back in her old life and loved to eat these things. Her Master had never stopped her from cooking for herself or eating whatever she wanted. In the initial days with him, she had continued eating all she liked, including greasily cooked meats. One day, though, her Master weighed her for the first time and his face changed to a scowl. She weighed 118 pounds. She could clearly see the disappointment on his face as he left her standing on the small rectangular appliance without saying a word to her.

She had been left there, stricken. He did not speak to her for days. Even when Master sat to watch the TV and she kneeled next to him on the floor, he would not run his fingers through her hair which he knew she loved. The next day, he'd put up the diet chart on the fridge but didn't talk to her or ask her to follow it. She had read it and resolved to follow it thoroughly. He put up an exercise chart next but didn't talk to her even then. She resolved that she would exercise daily if it pleased her Master.

She measured her weight daily and when she lost a pound, she happily told her Master. He still refused to even acknowledge her presence. She redoubled her efforts, and, in a few days, she was 114 pounds. When she told her Master this, he finally smiled at her and even called her a good girl...a compliment her Master rarely used. He even petted her head to show his pleasure. One thing led to another and her Master thoroughly fucked her to one of her most amazing orgasms. She remembered feeling such a warm glow inside her. Her Master then told her that she had disappointed him by crossing 115 pounds. Even before he could remonstrate her; she promised never to let it happen again. She wanted to maintain her body perfectly so that her Master would never be disappointed in her.

Even after all the restraint she showed, what had gone wrong? Of course! She smacked her head as she remembered. The night before, she was missing her Master like crazy. She had been feeling very lonely and decided to watch a movie. She had a lot of choices; her Master had taped a lot of movies of both of them having sex and even some of him punishing her like the naughty girl she was. She was watching a movie where her Master poured chocolate over his cock as he made her lick it off.

She suddenly felt a craving for chocolates and ice cream. Usually she was able to suppress such silly little urges but that night it had been very strong, and she was very lonely. She'd gone to the kitchen and dug out a scoop of her favorite chocolate ice-cream. She ate it like a greedy little pig. She loved the taste of the cold ice cream and the bitter dark chocolate on her tongue. She'd not had any in a long time. Without realizing it, she'd eaten up the entire tub of the ice-cream. You stupid fool, she thought. She knew better than to give in to such silly urges. She knew if her Master found out he would be displeased, and she had no one but herself to blame.

In the initial days, when he was displeased with her, he would punish her. He liked hurting her body and putting her through creative punishments. He would tie her up in different positions and whip her. She loved it when he punished her for being a naughty pet. Even now, she got wet thinking about the stings of the whip on her soft skin. She loved when he treated her like his pet and enjoyed every single moment of it.

Nowadays, however, if she displeased him, he would simply stop acknowledging her presence in the house. He would not just stop talking to her but unsee her in the house as well. Even if she tried to curl up on the sofa with her head in his lap, he would even stand up and sit in some other place to make his displeasure with her evident. He never shouted or got angry with her, but his disappointment was much worse than anger.

She had enough time before her Master arrived, so she thought of completing her exercises for the day. She went into the gym and put on the fresh sports bra hanging there. She always wore a bra while exercising alone. If her Master was exercising with her, she wouldn't wear anything because he liked to see her boobs jiggle and wobble as she exercised. Sometimes, it even turned him on enough to fuck her then and there. The gym was full of toys and equipment. They were useful for exercising but Master also used many of them to play with her or punish her when he was in the mood.

She did her basic stretching, then got a jump rope and began with skipping. Master liked her to be fit and healthy in an athletic, sporty kind of way. She did about a five hundred skips and put down the rope. She was perspiring but she knew she had more to go. Before, she would get very tired, but her Master would usually want to fuck her after the exercises. She hated the fact that she got tired and slowly built up her stamina. She was proud that now, even on long days, she could exercise and yet match her Master in stamina for multiple fucks. She also did yoga once a week to keep her body flexible. Her Master liked to try newer ways and poses with her and she needed to be very bendy for them. Today, she was not in the mood for either yoga or the treadmill; she knew she needed the vibra-cycle to take her mind off her current dilemma.

Her master had brought in the vibra-cycle as a tool for her punishment. However, she had enjoyed it so much that she asked him to make it part of her exercise regime. It was like a normal stationary bike except that near the seat a string was tied. The other end was tied to a shiny metal egg-shaped vibrator which she would insert in her pussy as she sat on the seat. The egg vibrator was small but powerful. Her Master did not like her to insert large dildos or vibrators unless he was punishing her. He liked her to keep her pussy tight.

There were also three wires from the dashboard on the handle. On the end of each was a suction disc. Two of them went on her nipples and the last one on her clit. She attached each one by first pressing the bulb to let out the air and then as she placed it on the right spot, she let go the bulb. It would suck in her skin with her nipples and clit and make an airtight vacuum. She liked the pressure, it made her wet. She spread her legs and put the vibrator inside and mounted the cycle.