Secretary - Day after Day

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

After she had cleaned up her last meal from her kitchen, she set to purging everything left over. He wanted her to clean all food out of her apartment to the point that she unplugged the fridge. After several garbage bags and a box to be donated to the homeless, all that was left was an open box of baking soda and cat food. She even got rid of her prized salt and pepper grinders. A little difficult, but she was focused on her future.

She felt a bit weird, parking in an empty lot. No one working on a Saturday. She was unsure what to wear, something casual? She chose what she typically would, a smart blouse and A-line skirt. The shoes, she put on in the parking lot. As she walked in she didn't know if training required the 30 minutes of walking. She was arriving 30 minutes late already! The panic and flushness to her face were obvious. She set her things down and paused, standing between the desk and her bosses door, debating whether to broach the topic, or if she should just sit and wait for his direction. She bit her lip and went in.

He was behind his desk and did not look pleased. She put her head down and approached the treadmill. Where her exercise clothes normally were, all she saw was a pair of 5" black patent leather high heels and a collar with a small leash. She was confused. She looked back to her boss sitting behind his desk, watching every move. She stripped, a pile of her stylish clothes on the floor. She put the shoes on and thought they were impossible. The extra inch made her feel like she'd never worn high heels. The collar was a bit awkward, she couldn't see the clasps, but felt her way around.

She "mounted" the treadmill, feeling more animalistic with the lead dangling between her breasts. Today there was a note and an arrow, showing where to attach the other end of the lead. There was also a pre-programmed time and regiment. As soon as she attached the lead, the belt took off, forcing her to grab the side bars to keep up. She found that if the lead was kept at a certain tension, the speed was manageable in the ultra high shoes. The pull on the collar was all she could focus on. If she let it slack, her feet in the incredibly high shoes could not keep up. Her eyes kept darting down to the display in disbelief. 3.5 hours remaining?! She was completely naked and constantly concerned with her pace so as not to trip and hang herself by the neck.

Her boss did very little sitting behind his desk. Mostly looking at his secretary struggle. She was determined, and bright to figure out the tension in the collar and leash influenced the treadmill speed. In another 10 minutes she would see the program he had installed. Random inclines would challenge her. Negative made the high heels seem higher, positive (uphill) gave her calves a rest. If she was to be walking that long, he had to give her some release, and challenge.

About midway through, her boss stood up and approached a box on the wall. She had not noticed it before, but could only guess. He pressed a couple buttons and then left the room, turning the lights out. She was not in complete darkness, but it was different sensation. To that point he hadn't said a word, but she was trying to process the changes he had made since yesterday. She hoped that this was not punishment for her misunderstanding of the 30 minutes of walk before work. She kept her concentration on the tension in the lead, and not tripping. Being totally naked was the least of her concerns. She didn't know if it was her imagination, but it started getting hot. Not warm, hot. Her sweat was now dripping from her. He must have turned off the air conditioner and turned on the heat. It was like a sweat box! And with an hour to go!

After the time wore down, the treadmill stopped on it's own. She was desperate for water. She removed the lead and rushed to the private bathroom, scooping handful by handful of water into her mouth. She even went to the effort of pooring water over her face and body. She did not think she could finish, but she had!

After toweling off the sweat and water, she returned to her pile of clothes and put them on. She was unsure about changing the thermostat, but being a bit "green" went to the wall and turned it down from the 93 degrees it said it was at.

She checked around the room, and then left to pick up her things she left at her desk. There was a note taped to her computer monitor, "That was punishment, not training. You are behind! Be here tomorrow at noon. Do not disappoint." She had a sense of extreme sadness overcome her. She failed her boss over something silly. She should have thought things through!

She made her way to her car, the butt plug and dildo being a constant thought with the changing of her weight. She unlocked her door and saw a note on the windshield. It said, "You need food. Anything left in your pantry should do."

She thought back, that means she's eating with her cat tonight. Great! She went home and watched infomercials. The cat food wasn't as bad as she thought, but her cat looked a little pissed. She was completely drained mentally and physically, apprehensive for tomorrow. A good thing, the instruments in her ass and cunt protected her from touching herself. That is all she wanted to do.

Sunday – saying hello for the first time

She woke up irritated and starving. He didn't know if her punishment would extend to breakfast, but she couldn't eat all of the cat food. The dildo and butt plug were getting more annoying than anything. Every where she went, they were there, rubbing her from the inside, constantly in her head. She was finding reasons to use the toilet, just to have a break.

She had tried to stay at least mentally busy since her punishment yesterday, but the cat food put her in a bad mood and the tv was not rewarding. This morning she was going to go through her closet and find clothes to give away. She needed to drop off the food that she had boxed from her pantry, may as well take some clothes for charity too. She had forgotten that the food was still in her apartment! It was gone from the shelves and gone from her mind. Oooohh, her stomach growled. There wasn't anything particularly good sounding, from 5lbs of flour to soup that she never should have bought, but it wasn't meant for a feline, it was meant for a person. Her head was fixated on the food.

Idle hands and the devil popped into her head. She got up and went to her bedroom. She turned up the radio and got to work. She would not fail. Her quest for control was not easy, but she was determined.

By 10 am her closet looked neat and organized. The dresser drawers could close now, and all the old socks with holes were relegated to the linen closet as dust clothes. She loved finding new uses for things. Next to her socks, her underwear. She couldn't help think that she may never get to wear them, as they could not hold the implements that were violating her 24/7. The garbage bag with the ugly, or ill-fitting clothes was going right to the trunk of her car, and then the box of food. She needed it farther away, out of the apartment.

She took a shower, removed the panties and carefully cleaned the parts, then reinserted, first the dildo, and then the plug. The novelty was wearing off and she found the lubrication that had been there before, was not. She was not enjoying the constant stimulation. On top of the hunger, the irritation grew.

She managed to leave the house a bit early and arrived 40 minutes early. Plenty of time to get her 30 minutes in. She did as she had done before and changed her shoes from the flip flops she drove in to the 4" heels. Her mind went to the 5" heels she wore on the treadmill yesterday, oh they were hard to walk in! She went in to the quiet, dark office and put her things down at her desk. She went into his office to find it as she left it. She went to take her clothes off and put the collar and chain around her neck, next she changed shoes. She got on the treadmill, ready to attach the leash, just before she locked it on, she noticed the time, it wasn't saying 30 minutes, but an hour. That is unusual. She tried to change the time but it wouldn't let her. She attached the leash and figured she would just keep going until her boss came or the treadmill stopped.

It took a few minutes for her to get back into the tension of the leash that controls the pace. She had started to "zone" out, putting the pain of her feet out of her mind when her boss came in. He didn't even look in her direction. She figured it was fallout from her disappointing him. She had 20 minutes left of the hour but since he seemed to be a bit grouchy, she decided not to bring up the time change. She hadn't heard his voice since Friday when he told her to go home early and wear her gift of panties.

After he found a few things in his desk drawer he went into the bathroom and turned the shower on, letting it warm up. He then returned to the office and turned the treadmill off with a special key. He explained, that was the only way to override the program. He unhooked the leash from the machine and led her off the equipment. While she waited, bare chest out, he took his hand between her legs to gauge her wetness from her walk. Where she would normally be very aroused, he found, not a dry pussy, but not nearly as wet as earlier in the week. Rather than having her lick his fingers, he tasted her for the first time. He pulled her along, passed her pile of clothes and in to the bathroom. It was starting to get a little steamy and she was very curious if this was training, or more punishment.

He lead her to the standup shower. It was larger than average with masculine slate colored tile and glass doors. He told her that this is her training and that she was a day behind because of her stupid behavior. He said her actions yesterday indicate that she is not learning. While her body is responding to the pain and balancing the pleasure, as indicated by his post exercise tests, her mind has not made the connection. The next step should help her internalize the need for mental pain, to achieve mental pleasure.

He told her to get on all four inside the shower, ass facing the temperature controls. He got a towel and put it under her knees, that was not the pain he intended for her, he explained. The shower had been filling a jug with warm water. He tested the temperature, it was still too hot, so went to the vanity and retrieved a few tools. He brought what looked like tubing, lubricant and a butt plug that looked eerily similar to the one that had been installed to her chair a few days ago. She could not see what he was doing behind her, but she had a sense that this was not going to be fun.

He admired her ass, and then quickly gave it a slap. A red impression slowly appeared. When his hand print was clearly visible, he slapped the other cheek slightly harder. She made a whimper sound at this, her tits swaying from the impact to her whole body. Her first thought was that was uncalled for, but then she put that thought aside, as what was done was done. It took her mind off the black butt plug within range of her ass.

She heard the bottle of lubrication open and then close. He knelt down beside her, rubbed where his hand print was hot on her ass, then with precision, he guided something into her ass, and far. It wasn't as big as the other plug in her panties, so it wasn't entirely unpleasant. He made a few adjustments, and then she felt it. Like there was a heater, but from the inside. The coldness of the shower on her skin was being warmed from within, and then she felt the pressure growing. She hadn't eaten much food recently, but the feeling of full was growing. It was slow at first, but then it was uncomfortable. She shifted her weight from knee to knee. He gently started to massage her abdomen... a little coaxing. He told her she was doing great and they were almost half way there. He didn't see it, but her eyes got huge. She didn't know exactly what was going on but knew this was torture!

When he had completed filling her up, he told her to close her anus as tight as she could, like she was holding back a fart. She put all of her effort into that. He removed the tube and then slowly coaxed the black plug in, sealing the liquid into her. She was shocked at how big the plug felt. Her muscles were starting to twitch and all she wanted was to push and push hard. He put a few of the tools on a shelf and began massaging her ass, being gentle around the burning hand marks. He then asked to sit up on her knees, hands on thighs.

He stood up and put the zipper of his pants in front of her nose. He explained she was to control the water in her bowels at all cost. He needed pleasure and she needed pain. She was to suck his dick until he was sufficiently pleased. She had done this with a few boyfriend before, but not under so much pressure. She unzipped his pants, being careful not to get his underwear caught in the teeth of the zipper. She fished around inside his pants and final brought out his already hard dick. It sprung out at her, as if to say hello for the first time. She started salivating, wanting to start out being very pleasing to him. She started slow and unsure. Trying to get a glimpse of his face or any indication she was doing okay. She brought her hands up to help guide the rhythm. He said no, and she put her hands back down. He grabbed her leash and back of her head and started guiding to his liking. Her mouth was getting sore, but she kept thinking of being as wet and warm in her mouth as possible. The movement of her body to maintain his pace was making her insides very unhappy. Her stomach was cramping and she could not control anything.

She tasted a bit of the pre-cum and knew it would be soon. She had to hang on a little longer. She thought she could feel the plug moving out slightly, if it got to a certain point, it would explode out of her. She started using her tongue, little flicks usually worked, and it did. He held her head hard against his scrotum, he was in as far as her face would allow. She had a hard time breathing, but stayed there, tasting the cum slide down her throat. It's funny, she thought how everyone tastes different. She started to hum, trying to get air. He let her head go and she gasped, trying not to spill an cum. She hadn't eaten all day, and this was her lunch.

He reached over and turned the shower on. It was bit cold at first, but soon was warm. He started washing himself, ignoring her at his feet. When he was done, he had her get on all fours again. He leaned over and told her he was removing it, but she had to hold it in for 5 seconds before letting it all out. She nodded in agreement. She clenched as much as she could. 1 mississippi, 2 mississippi, 3 mississippi, 4 oh I'm going to lose it... 5 mississippi. She did it, and the pressure started to be released. She was feeling weak and ended up laying on her stomach, letting the warm shower hit her and the warm water leave her.

It felt like days while she was lying there on the wet cool tile. When she final opened her eyes and thought the enema was over, she was surprised to find her boss gone. She slowly got up, very sore. She had the urge to sit on the toilet and found she wasn't quite done.

She dried off and found a note next to a box of cereal and gallon of milk on her pile of clothes in the office. It said "See you at work tomorrow. You can only eat the food I give you, apologize to your cat. Don't forget the panties".

Monday – anniversary

She woke at her alarm. She wanted to hit snooze and rub on herself like in her previous life of unemployment, but was acutely aware of the screaming in her ass. She had never had an enema before, but found it stressed her muscles more than standing in the 5" heels. She was a bit more up beat at having dinner and breakfast with people food, even though it was just cereal and milk. Her experience with cat food was not pleasant and she was eager to distance it from her mind.

She arrived on Monday like usual. Walked in with her 4" black heels on (their one week anniversary as it was). She set her things down and entered the office, ready for the 30 minute walk. She stripped in the office, not even changing in the bathroom because he saw all of her yesterday. He peeked up from his desk to watch her get ready, but did not say or do anything. To her surprise the shirt, shorts and 5" shoes where laid out. A walk without being nude sounded good. And the relief of not having to control her pace with the collar. Perhaps a reward, or punishment? She had a hard time telling.

As she walked, her mind started thinking back to her training. He had said that her body was reacting, was being controlled, but not her mind. It was still only focused on pleasure, and was not balancing with pain. She wondered how in the world the mind could be in pain. How could her ass full of water train her to have pain in her head? Her immediate thought of the enema yesterday was the intense torture right before the release, when she had to hold it on her own for 5 seconds, and then the immediate relief, that continued as she drained.

A flash came across her as she glanced down at the time remaining, 15 minutes. It brought a smile to her face. She made her boss cum. She wasn't sure he was ecstatic, but a man cuming in her mouth has always been well received. She realized that when she was sucking and licking him, the pain in her ass was there, but dulled. Her focus on him cuming, giving him pleasure over shadowed the intense cramping and ache in her belly. She thought there was something there, but her walk was up and she had to get to work.

She felt the excitement of undressing twice in front her boss. He didn't do his check like he did in the past, where he gaged her arousal by testing the wetness of her labia. He would have found her a bit wetter today, as she was able to think about her bosses cum in her throat.

As instructed on Friday, she was not to wear the gifted panties with dildo and butt plug, but was to be pantiless after the morning walk. She assumed that he would keep the large dildo and butt plug attached to her chair, but she was surprised when she pulled it out and there was just a regular chair. No instruments to torment her. She felt sad, empty, literally. She quickly sat down and powered up the computer and opened her emails. Her boss was in the habit of directing her via email with lists and lists of tasks to complete for the day.

She sifted through the ones with the closest deadlines and started going. A window popped up "How is my secretary today?". She didn't think IM chatting was allowed, but then remembered reading somewhere on the intranet that they have an office communicator that is meant as a collaboration tool, for business use only. Oh course it usually was only used for inter-office romance. She hesitated and just said fine. Rather than using the intercom he used on her first day, her boss found the IM more private, and so called her into his office. Standing up was not as laborious as it had been before, and she sprung up to her 6'-2".

She took her notepad and pen and headed in. On his desk was a timer, the kind they use for chess, that keep track of both sides of the game. He stood up and handed it to her. He instructed her to keep track of the time she either thought or spent typing in the office communicator (IM). He was going to ask her questions throughout the day. She was to reply in the timeliest way, but it must be truthful and accurate. When she was busy with her official tasks, the left clock would keep time, when she was thinking and typing about his questions, she was to be keeping time on the right clock. She was to work on the left clock, meaning, she needed 8 hours on the left clock before leaving tonight. There was no limit to the time on the right.

123456...9