Secretary - Day after Day

She agreed that this was a nice test. He had her complete the remaining work, 30 minute walk at the end of the day and she was home by 6 pm for the first time that week. He had fed her lunch, which she eagerly ate even though there was no time limit imposed. He had prepared an afternoon snack and dinner, which she took home. The whole night to herself, what to do? She puttered around, started laundry, did some old dishes, fed the cat, etc. It was then only 7 pm. With all this time, the thought turned to finishing what she started last night. She got up ready to lay on the bed and rub her way to an orgasm when she remembered the plug. Before the boss left he had handed her a bottle of lube. She had never used lube before as she was usually plenty wet by the time she would be ready for sex with her boyfriends. He said it was important to use it. She lubed the plug, pulled down her pajama pants that she wears at home, went down her underwear and attempted to insert... it was like a wall. She concentrated, but her vagina was yelling, she had to ignore it. The angle was awkward, maybe if she repositioned and slowly sat on it? She tried and with a few deep breaths, it was in and she wanted it out! She glanced up at the clock to start the 10 minutes.

She sat with the plug up her ass, afraid to get up, trying to block the pain. Her upper body was swaying, trying to find a better position that did not make her feel like a shit the size of China was stuck. She took her mind off of things, making lists of other things she could do rather than pleasure herself because if she knew herself, as soon as the plug was removed, it would need to go back in. She was correct, the plug was in for a total of 50 minutes in 10 minute increments until she had decided to read a book and go to sleep, frustrated, horny and out of control.

Thursday – Grain by grain

What a restless night! She could not keep herself still! Her eyes were red, her pussy was dripping, her nipples were sensitive. She tried to remember the last time she had gone so long without an orgasm. She was feeling like an addict in withdrawals. She knew that if she touched herself once, it would be all over. Even wiping herself after pissing was uncharted territory and too much of a temptation.

Rather than the jumping out of bed to rush back and complete the job of getting an orgasm, she slowly went through the morning routine, without orgasm. She was hungry again. Waiting to get to work for breakfast made her grouchy. She thought she would mention that to her boss. She didn't know how he would react to her suggestions, but this morning was not an inspired one.

She did the same as days previous, putting the 4" high heels on in her car, so that when she saw her boss, she was abiding by his rules as his secretary. He was in the office again, before her. Maybe he enjoyed seeing the 30 minutes of free breasts, bouncing as she was slowly learning to walk in her exercise, 3.5" wedge heels. This morning, he did not try to hide that he was staring at her. He stared at her like he would a race horse during its morning workout. While she was a bit uncomfortable with him watching, she felt a twinge of pride. He thought that she was worth watching and that made her blush.

As she completed her time and was folding the treadmill up and away, he stood from his desk and walked toward her. To this point, he had never touched his secretary. With swift, sure hands he reached between her legs, pulled away her short shorts. He felt the moist warmth that was created by his mandated exercise. She was so shocked she could not move. It all seemed benign up until this point. He did not linger, but rather immediately took his tainted fingers and headed to his private restroom. As he was washing, he ordered her to come to him.

He told her that obviously she did not take his experiment seriously. If she had, she would have had the butt plug in during her walk. It was without doubt that walking in the high heels caused her pleasure and she was not able to control herself. She tried to explain herself, but he shooshed her, put his hands over her lips. She was frightened now and he saw it in her eyes. He slowly took his hand away. He dried his hands, and asked her to follow him and take a seat in front of his desk. He sat behind his desk. She was still in her exercise clothes and felt a bit weird, a little exposed.

He explained that for there to be a change, she must listen to him. His only goal was a happy, healthy secretary. He then asked her to explain how the previous evening went and if she used the butt plug. She told him that each time she took it out, she had the urge to pleasure herself, and so she put it back in. He asked if using the butt plug made her more or less aroused. Her immediate thought was it took all arousal away! She hated that thing. But then she thought of the 3rd, 4th, and 5th times, the sensation of removing the plug. How there was a cold void. He could see the indecision in her face and suggested that perhaps she was unsure the affect the plug had on her.

His next suggestion seemed outrageous. He had the idea to install a slightly larger butt plug to her chair. This way, anytime she was seated at her desk, she could think about the affect it has on her. It would just be for today, and it would be lubed every hour, but this way, she could determine if it was bad/good feeling, or a bad/bad feeling. He had a hunch he knew which one it was, but wanted her to discover it for herself.

While she changed into the clothes she arrived to work in, he got to work modifying her chair. He stood back as he watched her pull up her skirt and try awkwardly to pull her panties aside while sitting. He made the suggestion that she remove them and put them in one side of her bra so they didn't get lost. That seemed reasonable to her, so she sheepishly removed her panties and stuck them into her left bra cup. This made sitting on the plug easier, but no less painful. She was shocked at the difference between the green one she used last night and this black one. There was no wiggling or adjusting. She was good and impaled.

He instructed her to complete the tasks in her inbox. She read through everything and realized her tasks could only be accomplished by going back and forth many times to the copy room, much like her first and second days. Every time she got up, relief, every time she came back to her desk, the agony of reinserting the plug. She could not sit without inserting it. She also felt a bit aloof as her breasts appeared lopsided. One slightly bigger with odd lumps, and the other, normal. She did not know the self conscious affect on her was akin to humiliation.

Finally it got to be too much, she hadn't had breakfast, she'd been impaled more than 8 times and she hadn't cum in days! She went into his office. He looked a bit surprised to see his freakishly tall secretary standing there when he had not requested her presence. She looked desperate, but she was afraid to say the first words, almost as if she was regretting even coming in. He said that she was there for a reason and to explain herself. She said one thing, "I'm hungry". He wondered how long it would take her to request food. He figured it would have been a few more days for her to gather the guts. He asked if the hunger was painful and if that was why she was there, requesting food. She nodded, not saying anything. He opened the side drawer of his desk and produced a bowl of cold rice. She was told to walk to the front of his desk, turn and face the office door, then get on all fours. She timidly did as she was told, carefully eyeing the mysterious bowl of food. He came around and placed the food on the floor in front of her. She stayed in that position, unsure if she could wait any longer to satiate herself.

He walked back behind his desk. After he sat down he told his secretary she may eat, but, she may have one grain of rice at a time, her hands must hold her ankles and her skirt was to be lifted so he could monitor her ass hole and it's now larger size. This was a lesson in pain and pleasure. It would not be a quick lesson, but that was the intent. It took her 2 hours to painstakingly finish her bowl. Her legs were cramping, her feet had been asleep for who knows how long. One thing she did appreciate was not having the plug going in and out of her ass. Finally her belly was full.

When she was done, he instructed her to return to her desk, and the chair with the plug, and complete her tasks. Also, that if she was ever hungry again, she was to kneel in front of his desk in that position, it was the only way he would know if she needed food.

While she was happy to have quenched her hunger, she was not looking forward to sitting on that plug the rest of the day. After she was done for the day, she returned to his office for her 30 minutes on the treadmill. This time, laid out, were only shorts and the wedge shoes. No shirt. She was going to have to do it topless! She did not sign up for this! And then she had a flash of rent due next week, and had no idea where the money was coming from. She changed in the restroom and came out, tits bouncing, bouncing. She couldn't resist the urge to support them with her hands, so she cupped them together. Under his watchful eye, he only said "add one hour to tonight's walk and tomorrow morning's. Do not touch your tits. You're not wearing a shirt or a bra for a reason".

As she walked and walked to nowhere, her mind was racing for the reason not to wear a shirt. After 45 minutes of her boss watching her labor in the heels, he shut down his computer and left. She was relieved, but knew that she was only half way done! When she was done, she put the panties that had been in her bra, on, to cover her vagina.

When she got home, it was a bit later, 7 pm. She was tired from the extra walking. She cooked the ramen he left on her desk on his way out, thankful that she had food. She tried to stop her mind from wandering, but her habit of turning to masturbation for comfort was immediately replaced by a green butt plug. She wore it most of the night. If there was a good thing, she found the green one wasn't as bad as the black one attached to her chair at work. Another discovery, she thought it actually made her more aroused, even though when it was in, she could think of nothing else than getting it out.

After putting the plug in and out all night, it was time for bed. She adjusted her alarm clock to be up an extra hour earlier. She was in such a frenzied state, if she did not have discomfort/pain to distract her, she may just masturbate in her sleep. She decided the intent of this exercise was to prevent her from pleasuring herself, be it conscious or unconscious. She slept with the plug in. Not far from that plug was a pair of glistening labia and a clitoris, begging, yelling and screaming for attention.

Friday – working a double

She slept better than she had the previous two nights, even with the butt plug firmly in her ass. Getting up an extra hour early was not appreciated though. Her first move was to remove the plug, use the toilet and take a shower. The water on her vagina was pleasant, but a frustrating reminder that she should not touch it. Even drying off she was afraid that any instigation on her part would end in a failure. The inability to control her own orgasm.

She wore a blouse and a skirt, as typical, with a bra and underwear, even though she knew they were not allowed for her 1.5 hour walk this morning. It was Friday, so she was looking forward to the weekend off. No high heels, no butt plugs, just hanging out.

She arrived at work, walked in with her 4" heels on. For the first day since Monday, her boss did not come in early, although, she was there an hour and a half early herself. She set her things down and went into his office. She picked up the shorts and 3.5" wedge heels and put them on. She didn't feel the need to use the restroom to change, as she was not allowed a shirt, so it didn't matter much to her. She started her walk.

Her boss came in with 20 minutes left to go. Rather than turning on his computer, he rearranged one of his chairs to face her. He ate his whole wheat toast, yogurt and apple as he watched her breasts, bounce with each step. She was getting better, more graceful at walking in the shoes, but it didn't come without some practice. She still slipped up a bit, stumbled a little.

When she had completed her 1.5 hour walk, there was a sheen to her skin. A thin layer of sweat, highlighting her features. As he did the day before, but this time she was topless, he shoved his fingers into her wet pussy, gauging the degree of wetness the walking had caused. Instead of immediately washing his hands... he shoved them into her mouth and said suck. After wiping his wet fingers on her breasts, he asked her to turn around and bend at the waist and hold her ankles. He was checking to see if the butt plug was inserted for her walk, since it was obvious that walking aroused her. The experiment was put in place to try and control her pleasing herself. A little green knob was sticking from her ass. A good secretary she was! He was pleased.

He resisted the urge to slap her open cunt, or her round ass and ordered her to get dressed, but to remove the green plug, wash it and bring it to him. When she was all put together she came out to find her boss behind his desk, waiting. He asked her to sit and hand over the plug, giving her feet a rest after the long walk. She hesitated, a bit reluctant. She had a connection with the plug, animosity aside. He asked if she had any thoughts about her control over her orgasms. If she was learning anything about pain and its different forms. She attempted to articulate that her first impressions had been wrong. She had an immediate response to what she should feel, but when truly evaluated she found the opposite was true. While she was screaming in her head for the plug to be removed, she missed it when it was gone. The pleasure of its removal was not the thought she would get. There was a weight of the plug inserted that was desired. She could not say that about the black plug, but of course, it was bigger.

With boss in full possession of the plug, he made an announcement. He felt the intended pain to block her pleasure response was not working. Time for a different approach. He had installed a dildo next to the black plug on her office work chair. He wanted her to complete the tasks in her inbox while sitting on both. For this to work, he requested she remove her panties and place them in his top drawer of his desk. She slipped them off and put them in his desk.

She pulled her chair out to sit down and her jaw dropped. She had no idea how this was all supposed to fit while she got anything done! Her boss came out to watch as she made her first sit down. His arms were crossed, watching intently. She pulled up the back and front of her skirt, to guide the implements in. She had a brief moment of what the hell am I doing, but pushed it aside as she hovered, unsure of how to proceed. Grasping the dildo, she eased onto that first, then found the familiar black dildo, lubed, but still pushing her beyond her comfort... at this point, she was oddly eager to sit all the way down.

She felt full. The sensation of being tacked down, but from the inside was exhilarating. Her face did not show this excitement. The boss could see she was having turmoil. Just as he knew the butt plug task was not the "experiment" he had described, the effect was rewarding. She attempted to find a better position, but there was no give. She had a grimace on her face. He made a mere "hmpf" sound and returned to his office, arms still folded.

She tried to work on her tasks... and thankfully, they did not need a lot of up and down from her seat. There were 3 times she had to make copies or use the restroom.

At 11.45 am she received an email from her boss. In official terms, she was invited to lunch to celebrate her first week as his secretary. She replied "Yes" and added the note: she was looking forward to learning more about her new boss.

At 11.58 her boss emerged from his office, coat on his arm. He offered her hand to imply that she was to rise off of the impaled implements in her ass and cunt. She quickly hit Ctrl+Alt+Delete to lock the computer and took his hand, picking up her purse and coat quickly feeling the cool void of both orifices. She wanted to turn and see if she left any wetness on her seat, but he was pulling her forward towards the door. He had a perfect view as she stood up and to his pleasure, the evidence was there, the pleasure of the butt plug was amplified by the dildo. This was going to be a fun weekend!

They went to a quaint café. He ordered for both of them and she was acutely aware that she had no underwear on. She noticed when they got out of the car at the café that he had a gift bag, not large, something you would put a scarf or pair of gloves in. After he had ordered for both of them, she was presented with it. A "welcome to the club" sort of thing, he explained. Rather than open it at the table, she was told to use the restroom and put it on. She was warned the lock on the door was a bit tricky and to lock it all the way.

She was intrigued and a bit perturbed, the blt and iced tea was not her "cup of tea". But it was part of her boss's requirements.

As she closed the door she saw what he said about the lock and she double, triple checked it. She set the bag on the counter. She removed a pair of underwear, but it had attachments. It looked similar to her desk at work. There was plug – smaller than the black one and a dildo – smaller than the one at work.

She walked out of the restroom, in her heels, breasts pushed out and two holes filled. She sat down with a smirk. He asked what that look was for, and she had no words. To fill the time she told him her mundane family story and he was cryptic. He wanted to know about her social life, living situation, etc. They finished eating and he took her back to work.

When they arrived he asked her into his office. Once across the threshold, he asked for his gift back. She was sad. She thought this would be a more permanent thing. She was told that while at work, she was to be pantie-less and would sit at her chair as it was currently configured. After her walk in the evening, she was to put the gifted panties on and wear them until she returned for her morning walk.

He also informed her that there was training she would need to better serve him. He hoped she was not busy the next day, Saturday, at noon. She confirmed that she did not have plans that could not be rescheduled. He said good and sent her home early, along with the panties. She was instructed to decide on her own healthy dinner and breakfast with what was left in her refrigerator and pantry, then clean them out bare, and unplug the refrigerator.

She was relieved there would be no additional walking, as her tummy was full and feet tired. She was asleep by 3pm. Comfort in the fact she was full, front and back.

Saturday – 93 degrees

What a brilliant 15 hours! She needed that and was thankful to her boss for letting her leave early from work and sleep in. She was a little upset that she had to change her plans and cancel the brunch and shopping with her best friend because he requested her to be at training at noon on a Saturday, but was thinking this job was turning out okay. It was a bit eccentric, butt plugs, high heels, dietary and exercise requirements. If anything, it was definitely better for her than what she was doing on her own. She was becoming a better person because of her boss's control. This made her feel more confident that what ever was involved in training, was for her own benefit.

She made her own healthy dinner the night before and was looking forward to a "clean out the fridge" omelet. The panties she received as a gift yesterday were only removed when she had to use the restroom. Getting the dildo and butt plug in and out was becoming easier, even in the 20 hours since she received it. There were a few moments of being uncomfortable, like when she bent over to pick up the dirty laundry, or when she was shaving her legs around the ankle. The angles were adding additional pressure.