Secretary Day After Day

Monday – Giraffe on Rollerskates

There are a million "secretary" stories and fantasies out there. I have often used varying scenarios to help myself cum. Here is the beginning of one... (there will be more as I've completed Tuesday and Wednesday)

She had just started the new job. A secretary. Well below her station, but the unemployment was running out, there were no jobs that fit her degree. She could copy, and email, so figured she was qualified. She wasn't sure exactly what her new boss did, but knew the pecking order was more of the traditional, meaning, she worked for him, and him alone. She sat outside his office, at a cute little desk.

When she arrived, she was a bit nervous, but the promise of real money was motivating. She was getting a little bored sitting at home all day watching soap operas and game shows whilst treating her body like an amusement park in all parts of her apartment. The imagery was recycled to a point that she was grasping at the elements in her imagination to complete the task of orgasm. Of course, she knew once she got one, the second would come much easier and was worth the hours of rocking her ass back and forth over her fingers.

The woman from HR gave her a quick tour. Copy room, lunch room, your desk, his office, parking pass, password to the computer. That was it. She realized, she still had not met her boss. Oh well. She sat down at her computer, logged in, perused the filing system. Now what? She sat and waited, the boss did not appear to be in yet.

20 minutes later her boss strolled through the office like he owned the place (and he could have, she didn't know).

"You must be my new slave, ha ha, just kidding, I mean secretary", he winked. We shook hands as I stood. He looked a bit surprised. "Well aren't you kind of tall?" She was above average at 5'-10", but she didn't know any different and just lived a bit higher than everyone else. Also, because she was so tall, she could get away with not wearing high heels. She didn't feel the need to be over 6'-0" tall and be even more of an anomaly. She neither wanted to stick out or disappear.

He said that he'd get her something to do shortly and to just hang tight.

She sat back down and thought, it won't be too bad. At least he has a sense of humor. His eyes had a glint in them too, something she couldn't put her finger on. Almost like he knew something she didn't and found great amusement in it.

10 minutes passed and a voice came from a box on the desk. "Please come into my office, I found something for you to do."

He told her that he didn't have much in the way of copying and typing right now, but he did have a requirement of high heels at work. He had an extra pair his previous secretary left, but they would be far too small for her. He pulled out a credit card and instructed her to buy one pair of black high heels. They could be any style, but had to be 3-4 inches high. She was to wear them out of the store. He instructed her to walk as slow as she needed and to bring the shoes she had on, back to him.

This seemed a bit odd, that her boss would dictate what she wore, but she figured he just had some power trip thing going on. She needed that job, and if he was going to buy, why not?

The sales lady thought it strange that she wanted to wear them out of the store, especially because she looked like a giraffe on roller skates, very inexperienced and unsure of herself. The walk to the car took ages and she regretted picking a store in the mall so far from the parking garage. She was also regretting driving a stick shift car, because the area to hit the clutch was so much smaller in the new shoes, her foot kept slipping off. Not a very smooth trip back to the office.

She stood in front of her new boss with the shoe box containing her old shoes and waited for him to finish his phone call.

After he hung up, she put the box on his desk, displaying the awkward movement the shoes forced her into. He told her that those would do and that she looked freakishly tall, but his rules must be followed at work. He said that he emailed some things that needed to be completed by the end of the day, mostly copying and collating. She would spend most of her day slowly walking back and forth between her computer and the copy room.

She took the shoes off after getting in her car and drove barefoot home. She didn't even stop to get groceries because she didn't have another pair of shoes. He kept them in his office, which he locked at night.

It was past 9 pm so she found some canned vegetables in the pantry, ate them from the can, put the tv on sleep mode, massaged her aching calves a bit and was probably asleep before her head hit the pillow. She did have some interesting dreams about rubber bands, paper clips and staplers, her new tools of the trade.

Tuesday – Naked at work

She woke up feeling refreshed after her long first day at her new job. Then it came back to her, she had to go to work. She had been so used to waking up at noon, starting her day with a bit of rubbing and an orgasm, resulting in a glow and smile that got her through the rest of the day. She looked at the clock to see if she had time to do the same this morning. If she hurried, took a shower, and rubbed one out while she waited for her hair to dry, and then ate breakfast in the car, she should have plenty of time.

Excited she jumped out of bed, knowing she would be returning to it with a clean, naked body to defile. It took a little more time to reach her goal than it usually does. Every time she would get close, she would lock her legs and point her toes. The pain in her calves, from the shoes yesterday, was too distracting and the moment to cum left. Eventually she got the image of herself naked, wearing just the high heels, walking through her new office, breasts bouncing... ahhhh there it is.....

As soon as she caught her breath, she immediately started massaging her calves, realizing that she'd be wearing those shoes all day again!

No time for round two today so a quick blow dry of the hair, grabbed an apple, smeared some peanut butter on a piece of wheat bread and hit the door. She left the high heels in the car the night before, so she left the house with just flip flops on. They looked a little strange with her silk collared shirt and wool skirt, but were just to drive in.

Once she pulled into the parking lot, she moved her seat back and put the high heels on. They did elongate her legs and make her push out her breasts, making her look more feminine. She had a thought back to the image that finally got her to cum. It brought a smile to her face, how ridiculous that would be, naked at the office...

Her boss was in before her today. She set her things down, powered up the computer and stuck her head in the door to see if he needed anything. He said to check her email and re-read the instructions for the work he had her do yesterday.

She read the email and found that she mis-read some of the instructions. Much of what she did yesterday would have to be redone. There was also an email from her boss written at 6 am, nearly 2 hours ago. It was marked "high importance". Uh-oh, she thought. My first day and I'm already getting in trouble!

"Your lack of attention to detail has cost both of us our time. We can never get it back. When you were hired it was assumed that these tasks could be done by a 2 year old. Is that what you are, a fucking 2 year old? Stop acting like it. When I give direct instruction, it should be done just as I say and in a timely matter. Do not be a stupid cunt.

I am aware you are new, and you do not understand how I work, but what happened yesterday is UNACCEPTABLE!!!! Punishment will be spared, but you will fix your mistakes on your own time. If this means you are here all night to fix your fuck up, fine. There will be no sympathy from me or any other staff. This is how I work. You don't want to end up like my previous secretary, do you?

Straighten up, go give yourself a pep talk or something. Priority one, fix your fuck up. Priority two, come see me. Priority three, lunch break – it will be 3 minutes today. You have a lot to do today and I anticipate you will not be getting paid for it.

-the boss"

Her eyes were wide. She was breathing deeply and timidly. She was wet and slightly stimulated, like a hum, but was more concerned that she infuriated him so easily. It was her first day and now he thinks she is a "stupid cunt"? How could this be? She is smart and educated, sometimes funny.

She did as she was told and went to the restroom, stared at her reflection, trying not to cry. Trying not to show a weakness, even if she was the only one there. "I want this job. I need this job. I will do whatever it takes to keep it. Even if boss is a little hot headed, I can handle this. Just do it." She fixed a bit of her mascara, opened the restroom door and walked out, head held high, chest out, but still with an awkward gait.

She re-read all of the instructions to ensure she did it to the "T" this time. Her feet and legs were screaming at her to sit down, but she couldn't. She went through all of the same back and forth on the high heels as yesterday, but this time she was showing drive. It did not take as long, but it was 5 hours of constant work. 5 hours she would not be paid. She would not leave until at least 10 pm!

As told, she stepped into bosses office. He did not ask her to sit, but started his thoughts on health and the body. She remained standing, shifting her weight to try and alleviate the twitching muscles in her legs. He told her he thought the body was a temple. It can provide so much. The value to feel both pleasure and pain is a gift that most ignore, focusing on the shallowness of solely "the good" while limiting "the bad". He felt that true pleasure could not be felt, unless it was equally balanced with pain. He revered health both in himself and those that surrounded him. He demands that all of his secretaries get exercise and follow a healthy diet that he dictates. This would start with priority 3, lunch.

She was given three minutes to eat a sprout sandwich, an orange and drink 16 oz of milk. She could not finish and he explained that she must eat everything in his diet. He allowed her another 2 minutes to finish.

Next he explained the exercise regime. She was to arrive 30 minutes early and stay 30 minutes late, on her own time, to use the treadmill in his office. He pointed into the corner where a machine was folded up against the wall. He pointed out that he had time yesterday to determine her size. He showed her the required exercise clothing. The t-shirt, it looked a bit small and she imagined it would hug her breast tightly. The shorts were short, but should not be a problem. The shoes were her size, but a wedge style, he said for safety. They were still 3 ½" high. She thought the shoes would be a challenge. He made a point that the exercise clothes he was allowing her to use were the only clothes allowed during exercise. She thought that was a strange statement, and then realized what she would not be wearing, her underwear and bra. That will feel weird she thought, especially because in the past, exercise made her vagina very wet. She had no idea why, but now there would be no barrier. Another realization, this means she won't be leaving until at least 10.30 pm!!!!

He asked if she understood, then told her that he had more tasks to do in her inbox and to not fuck them up. She read through the tasks several times. Luckily, none of them required much walking, so she spent most of the next 8 hours typing and answering phone calls. Before the boss left, he gave her dinner in a container that could be microwaved. He instructed her that this was all she was to eat until he gave her breakfast the next morning. She agreed and went back to work.

She finished up the typing around 9.45 and went into his office, which he now kept unlocked. She did not find a need to change in the restroom as she had been there alone for hours. She look off everything, including the shoes, she snickered to herself, "I guess being naked at work wasn't so far off". She put the exercise clothes on. Indeed the shirt was tight, but her breasts were still perky enough to look good without a bra. She finished dressing and started her 30 minute walk. It was not as bad as she thought. The desk work gave her legs a rest, so this was more of a focus of not looking like a giraffe.

She made it home by 11 and resisted the urge to snack on anything. She collapsed on the bed, face down. She thought it'd be nice to have an orgasm, but she was so exhausted! She put her hand between her legs, just to check, it was very wet. She thought she may get a quick one in before she falls asleep. She started rocking back and forth, brought the second hand down for pressure and thought of work and that email her boss sent. She fell asleep in that position, fingers in the lips of her wet labia.

Wednesday – Yelling Vagina

She woke up sore. Her head was turned to the right, her arms were beneath her body. She didn't even take her shirt off. She was starving! Then she remembered that she was supposed to be to work 30 minutes early. She couldn't even fit in a pre-work orgasm. This is annoying she thought. All to keep a job? What will he know if I have a quick snack before I go? Then she thought better of it. He mentioned something in his email yesterday about what happened to his previous secretary. It must have been bad if she wasn't there. She showered and got ready. She noticed that the dull pain in her calves wasn't as bad, but her ass was throbbing. The 30 minutes of walking straight must have done something to those muscles.

She put the high heels on in the car again and walked into work. Her boss was there early again. She went into his office and didn't make eye contact, just picked up the workout clothes that she had put down last night. She did notice they were folded differently than she typically does it, but didn't worry about that. She started to walk out to use the restroom to change, but he said he would prefer she use his private bathroom off to the side. He said it was more private. She didn't even know he had a private bathroom. It makes sense given how long he's in his office and doesn't come out.

She quickly changed, hoping the quicker the 30 minutes were over, the faster she could have breakfast. Something she had not considered last night while she was walking, was that when the boss is here, he has the perfect vantage to watch her struggle with getting used to the shoe height. She was suddenly feeling vulnerable, but did not want to disappoint. The urge to hold her bouncing breasts and cover the hard nipples was strong. Thinking about her nipples got her focused on the wetness in her shorts. The friction between her labia was not helping either. It was a stream turning into a raging, warm mess. The boss said nothing, and appeared to be reviewing some printed forms. When she was done, she changed back to what she wore to work.

He asked her to sit in one of the two chairs across his desk. He started talking about the tasks for the day. She was trying to listen, but the hunger in her belly was distracting. He asked her something about a stain, she snapped out of it. Sorry boss, can you say that again, I was a bit distracted. He gave her a stern look, like "how dare you"! He asked the question again, "I noticed that there was a dried white spot in the exercise shorts. This is a very personal question, do you pleasure yourself?". The question took her breath away. How did he know, she thought. She answered slowly but honestly. "Yes, I have for as long as I can remember. Before I got this job I would do it up to 4 times a day. There was nothing to do and it helps me clear my mind. I do a lot of thinking during the build up." He then asked if she found the walking "pleasurable". She did not say she liked it, but didn't say she didn't. She did explain that she had noticed in the past when working out that she would get wet.

He then asked her if she remembered what he said about pleasure and pain being a balance. That to enjoy pleasure, it must be contrasted with pain. She did, but wondered where this was going. He asked if she felt her life was out of her control. Her quick response would have been no, that's silly. She is educated, well spoken, has a few very close, loyal friends. She can be the life of the party, or the wall flower. Before she could answer, he put up his hand in a "stop" motion, and told her to go to her desk and think about that. That would be her work for 1 hour. She was to make a list of the parts of her life. After that, she was to continue the tasks he had sent to her email. He would call her in when he was ready to hear her reasoning.

As she sat down and wrote down the compartments of her life she had a thought that this is the perfect topic to work out while masturbating. She immediately had a response to that, plus the unfinished business the night before, plus the walk. She was still hungry, but her vagina was yelling louder for attention.

Her list contained:

Family

Apartment

Student Loans

Car

Sex – or orgasm

They were in no particular order, but written out like this, her life seemed small. Uncomplicated. She really thought about the question. Control, vs out of control? She was not very close to her family, but they got along. She immediately got hung up. How could she control family? Her apartment was in constant disarray. She could imagine word getting out of its messiness, she feared animal services would take her cat away if they saw the condition. She also feared if she got in some kind of accident and a family member, or worse a stranger saw it, her secret of unkemptness would be revealed. Her apartment was out of control. Her student loans were automatically deducted, so they were in control, but not by her doing. If technology did not allow it, they would be out of control. Her car was like the apartment, so it was out of control too. Now for the one near and dear to her heart, orgasm. Of course she's in control, she has them all the time... but that's not the question. Do they control her, or does she control them? Hmm, her mind wandered to her wet pussy and how she could go get a little relief by going into the bathroom stall... a light turned on. She assumed her orgasms were controlled, but really they had been running rampantly out of control her whole life. How was it this was just revealing itself.

After an hour, she put the list away and tackled the other tasks, her stomach growling. It was nearing lunch time when she got the call to go his office and bring the list. Her conclusion to him was that her life was generally out of control. They went through each aspect. He asked questions, trying to determine what his secretary needed. First, he asked if she wanted to be in control. She said she didn't know, her life has been like this forever. She wouldn't know what control was.

He suggested an experiment to see if she could handle a little balance in her life. He proposed the next time she had the urge to pleasure herself, she should put a butt plug in for 10 minutes. He pulled out a green butt plug. It didn't seem like a such a hard thing she thought. If this will help her gain control of something in life, she was willing to try it. He did not see a terrified reaction, so the next question was if she had ever had anything in your anus? She had boyfriends get confused about where they were putting their penis, but she quickly redirected them to her warm pussy. He got a smirk and informed her they were trying to have anal sex with her. She did not know then what her reaction to the plug would be, and was slightly nervous. He told her to go wash it and put it somewhere she can access it anytime. He did add a caveat, that no matter what, when the plug was in, she was to resist the urge to pleasure herself.