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Saint To Slut in Just Seven Days: Monday, A.M.

"Samantha buys a skirt that leads to a whole new way of life."

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Author's Notes

"Due to word limits, I have had to break each day into at least two parts. <p> [ADVERT] </p>I hope it is still easy enough to follow."

This isn't a confession as such and it's not a diary entry as I have never kept a diary in my life; it is just the sordid story of how my life changed in a week.

It started with me doing something that I hadn't done in a long time. Perhaps because it had been so long since the last time that I was out of practice. It was something that I avoided doing as much as possible. I didn't enjoy doing it because it filled me with dreaded anxiety and it was generally a rather depressing exercise. What is this incredibly difficult and tedious task, you may well ask? Did she go bungee jumping? Sky diving? MMA fighting? Well, no, nothing that extreme but it sometimes felt like it to me. I went clothes shopping. Worse still, I went clothes shopping during a time when I was feeling quite confident. Sundays find me relaxed and combined with the good weather tends to have me feeling good about life and therefore a bit more confident.

Monday morning comes around, however, and I am not the same person I was on Sunday afternoon. I looked at the clothes I had purchased yesterday and laid out to wear today and wondered if I was perhaps mildly deranged yesterday. Did I drink alcohol at lunchtime? No, I don't think I did. What the hell was I thinking? I mean, don't get me wrong, it was a very cute skirt and blouse combo and, when matched with a jacket I already had, it was a very nice outfit. But and I do mean a large, all capital letters “BUT” here, that skirt was way shorter than any other skirt I had ever bought before.

This might sound ridiculous, but I usually used the “freckle” rule when buying skirts. Thanks to my Dutch heritage, I am fairly tall for a woman at six feet, two inches, and I have quite long legs. This was something I got teased about a lot as a kid so I had made a habit of trying to disguise my long legs with long skirts and dresses. Just over halfway down my thigh, closer to the knee than my butt, I have a freckle. I have never bought a skirt that didn't fall past the freckle, usually a long way past it. This skirt was above it. It felt way way way above it but in reality, it was about two inches above it. It wasn't obscenely short by anyone's standard but it was a lot shorter than any I had ever worn before and short enough to gain attention from those who liked to look. The thought of this gave me a small thrill but also terrified me.

I eyed the skirt suspiciously as though it had dared to shrink overnight but then, after a lot of self-goading, I told myself to get over it and just put the damn thing on. I pulled it up and slid the zipper up after tucking in my blouse, then turned to look in the mirror. To my surprise I discovered that it looked good, I mean really good, perhaps a little too good if you catch my meaning. I was impressed with the way it hugged my thighs and accentuated my butt. I liked the way I looked in it and although it was quite a professional-looking skirt it was somewhat sexier than I usually wear.

It was at that moment that I thought of Stefan. He was, undoubtedly, a good-looking man. He always wore the nicest tailor-made suits and he had a very nice figure. Such a great squeezable ass. I blushed as I thought about getting a nice firm handful of his ass and perhaps a handful of something else might make a nice change too.

“For fuck’s sake, Samantha, has it really been that long? Are you that incapable of getting through the day without thinking about cock?”

I blushed even further, realising that I was talking out loud to myself and thinking far too much about cock. It wasn't something that I would normally obsess over but just lately there had felt like a distinct lack of it in my life. I hadn't even bothered trimming lately and to say it was a bit of a wild jungle down there was gross understatement. God help me if some random situation occurred, like I was hit by a bus and carted off in an ambulance, or even more terrifying, I found myself in bed with a man. I laughed at the ridiculousness of that thought but still vowed to tidy up a bit tonight. Perhaps a little attention and self-appreciation might help take my mind off the dry spell I had run up against.

My phone alarm started beeping and I realised I had dawdled and day-dreamed a little too long and now had to hurry to catch my train on time. I no longer had time to change my skirt now and the decision had been made for me. I threw my jacket on, picked up my bag and ran down the stairs. I grabbed a breakfast bar and my keys as I ran through the kitchen then I was out the front door. It was only two blocks to the train station and then down a huge flight of stairs to the subway. It would generally only take me ten minutes to get there and that would see me getting there just before the train arrived providing nothing goes wrong between here and there.

Thankfully it was a smooth trip, being early in the morning, and I made it onto the platform as I heard the train rumbling around the bend coming into the station. It was kind of nice to pretty much walk straight onto the train without waiting but it did leave me feeling rushed and when you start the day rushing around you feel like you never catch up.

I looked around the mostly empty carriage and chose a seat. One advantage of being near the end of the line when you get on the train is that you almost always get a seat straight away. I wasn't obsessed with getting a seat on my own because usually by the next station, or maybe the one after the carriage was pretty full anyway. Because I didn't catch the first or last train of the day either it was usually an express train, meaning that it stopped at fewer stations. It made it a much quicker, smoother trip into town. If I needed to get into town half an hour earlier than usual it meant I had to start out over an hour earlier. It was always busy on the first and last train of the day too.

Other routes around the city were far more populated and the trains ran twenty-four hours a day there, but I lived in an area that wasn't massively populated and then it was mostly office workers of some description like myself that caught the trains. People with real money drove their BMWs and Mercedes into town and parked in their private parking spaces; while those who worked in industry or construction usually drove because the trains were rarely going where they needed to go and they couldn't carry all their tools.

I sat down and dug around in my bag for my book. After finding it I placed my bag between my feet and leaned back into the seat. It wasn't long before I was lost in my story. This was an unusual choice of book for me. I read a lot of different styles of books, usually fantasy fiction but rarely anything very erotic. It's not that I have a problem with erotica, it's just not usually my go-to genre. This book was a recommendation from a friend. It was primarily a sci-fi story but there happened to be quite a bit of erotica in this one. I was enjoying the story and the sexual escapades in it were as hot as they were unexpected. Several times I had found myself squirming in my seat as my pussy reminded me of its existence and the fact that it had been quite some time since it had seen any action.

I was in the middle of a very erotic scene where the main protagonist had his cock buried deep inside the pussy of his counterpart and was railing her enthusiastically. It was incredibly vivid and detailed and I was getting very turned on. I lowered the book to take a small break because I could feel my face becoming flushed and I was fighting the desire to reach down and give myself a little rub. As I lowered the book a little, I looked across at the seat opposite me. A man was sitting there in his suit, and his face looked as flushed as mine felt. He was alternating between licking his lips and gently biting his bottom lip and his eyes seemed to be glued to my lap.

What the fuck? He's looking up my skirt! I thought as I was about to sit upright and cover myself up, but then something stopped me. It was the strangest thing, normally I would be mortified, but instead of indignation or anger, a shiver ran through my whole body. The moment I realised that my short skirt had betrayed me and that he was staring at my panty-clad pussy I had two thoughts run through my head.

“That dirty bastard is staring at my pussy!” This was said in my mind with disgust and anger.

Quickly followed by, “That dirty bastard is staring at my pussy.” This time it was said with a smirk and a shiver of excitement.

The two emotions were at war with each other for no more than a microsecond with a sound and shocking victory going to the slutty side of my personality that was all but dormant these days. It seemed to wake up with a snarl and a lot more strength than I would have believed. My nipples hardened almost immediately and the excited tingling I was feeling in my pussy seemed to go up a notch or three. I almost had to force myself to not respond in the way I normally would but once I mastered and overcame the impulse to slam my thighs together and I realised I was now deliberately showing this man my underwear, my excitement went through the roof.

I never would have believed that being an exhibitionist would turn me on quite so much. I mean, yeah, I knew it would probably be exciting but not something that people like me do, but this level of excitement was something else altogether. The thought that the only thing preventing him from having a perfect view of my undoubtedly wet pussy was a pair of thin, floral-patterned, cotton panties was incredible.

Keeping my book up but just low enough to appear as though I am engrossed in it and not watching this naughty pervert, I moved my legs just slightly further apart and tilted my hips a little further back. His eyes widened even further and I had to stifle a giggle. The very real struggle I was having at this point was to stifle the desire to give myself a little rub right in front of this stranger. How fun it would be to pull my panties to the side, spread my lips with my fingers and play with my clit right now. My little fantasy had me getting so hot and wet as this was going on. I seemed to lose all track of time as I watched this man watching me. The train began to slow down for another station and I glanced up at the platform sign and was shocked to see that we were only one station away from my destination.

The train took off again and I stayed in my current position for as long as I possibly could until I had no choice but to move. I folded my book closed and sat upright, closing my legs in the process then reached forward for my bag. I placed my book in the bag and tried to collect my thoughts. It was like my brain had sort of short-circuited.

The train slowed right down as it approached my platform and I prepared to join the passengers as they stood up ready to get off. I glanced up and the man who had been so entranced by my crotch the whole way in was now standing in front of me with his own crotch only an arm’s length away from me. He was trying to be nonchalant but it was obvious to me at this height that his cock was rock hard and straining against the front of his suit pants. While I watched surreptitiously out of the corner of my eye, I saw his hand sneak out from under the coat he was carrying. He squeezed and pushed as he tried to wrestle his cock into a more comfortable and somewhat less obvious position.

I had to close my eyes and take a deep breath. I wanted nothing more than to reach out and squeeze that cock myself. He wasn't a man that I found particularly attractive but damn the situation was driving me wild. I stood up and for the first time, our eyes met. Normally I would have never held eye contact with a stranger on the train but this whole experience seemed to have changed something within me. I gave him a knowing smirk and winked at him. He blushed a deep crimson red but said nothing. The door slid open and I chuckled as I turned away from him. I walked off the train and across the platform displaying my best ass-swinging swagger that I could without looking like I had dislocated a hip or something. I could feel his eyes on my ass the whole way across the platform.

The two-block walk from the train station to work was one of the best I had ever had. I couldn't believe how confident I felt. I wasn't used to feeling desired like that and I discovered that I liked it a lot and wanted more.

My boyfriends in the past had been of a certain type. Almost to a man they were shy, lacking confidence, needy, and inexperienced with women. I couldn't have told you why I continuously went for this type, other than perhaps my own lack of confidence. I have no idea what it was about this type of man that I found alluring, maybe I felt that I could help them find some confidence, but it was also the reason I had been single for a long time now. I knew they were no good for me and as a result, I had all but given up on dating.

I arrived at my office building and rode the elevator up to the twentieth floor. It was a tall building almost entirely full of office spaces. The top floor was a restaurant that had a separate elevator, although for health and safety reasons you could get to and from the restaurant via the stairs but nobody ever did that. The people who worked in the offices of this building were not of the right wage bracket to be eating at this restaurant with its amazing views and menu, so the stairs had probably only ever been used a dozen times since the building was opened, sometime back in the nineties.

The ground floor had a large reception desk with people to guide visitors to the appropriate floors and offices as well as a café and public toilets. It had a large, plant-filled atrium and an open feeling. The fittings and architecture were all modern and beautiful but it was a facade. The majority of the building was purely about functionality. Peek behind and into any of the staff-only areas or the stairwell and it was all the dull, grey concrete and steel of practicality.

The office I worked in was essentially one-quarter of the twentieth floor. We shared the floor with three other businesses. The elevator runs up the centre of the building and when you exit the elevator, you step into a curved corridor that runs almost entirely around the elevator shaft.

Turn left and there is a door on the right to Finkal and Sons. Nobody seems to know what goes on in there because there is rarely anyone in the office, the door is always closed, and there is no other signage to suggest what kind of firm it is. There are rumours of course and I have heard everything from blood diamonds, mercenaries, and dark web specialists. I think it's most likely a tax dodge which is a far less romantic or exciting option but infinitely more believable.

Continue to the left and you come to the end of the corridor that is our front door. When the business is open, so is the door. That was Mario’s rule and Stefan hasn't changed that since taking over. Not that I minded either way. There was no passing traffic and if someone came to the door then it was for only one of two reasons. They either had an appointment and I knew they were coming, or they were lost, having gotten off the elevator on the wrong floor.

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Turn right out of the elevator and the door on the left opened to Snow Blossom Enterprises. A name and business that just felt icky to me. It was a representative business. A business that represented women, and women only, in the entertainment industry. It sounds very exciting, as though you expect a famous actress, pop star or author to be lurking in the corridor when you come and go from the elevator but that couldn't be further from reality. The only women I ever see there, apart from the staff in their sickly pink business suits that they all wear, are either angry feminists who don't look happy to be there, or down-beaten young women who appear as though they have been taken advantage of from the moment they stepped out of their homes as wide-eyed teenagers full of ideals and hope. I had never seen a woman go into or out of that falsely cheery, pastel-coloured, office looking happy or excited and that included the staff. I don't know what they did in there but the place gave me the heebie jeebies.

The last office on the floor belonged to another family business, Tompkin’s re-distributions. It's a vague name that told you very little about them but it was a business that dealt with death. Quite literally in a sense. I get along quite well with their receptionist Marcy. She's the person who recommended the book that I had been reading on the train. We have lunch together from time to time and for someone who works in a predominantly unhappy industry, she is an almost obscenely happy and upbeat person.

She explained to me once that the office was basically the headquarters for the business. It was the brain that told the limbs how and when to act. As such, there were rarely any clients walking through their front door and the majority of her office time was spent sending and receiving e-mails as well as being permanently glued to the phone.

When a person died and they were the last of their line or there was no immediate family in the picture, it was their job to deal with the physical leftovers of life. Insurance companies, banks and the government were their primary clients. It was their job to clean up and sell any remaining property belonging to the deceased once it was established that there were no beneficiaries. They had people working for them spread all over the country and they needed an office with a decent phone and internet system as well as a boardroom for when there was a need for meetings. This office was essentially the hub of the wheel.

This morning I spared no thought whatsoever to the other three offices as I stepped off the elevator and turned left. The door was already open when I got to the office, meaning that Stefan was already there. It was sort of fifty-fifty as to who opened in the morning. Sometimes Stefan had somewhere else he needed to be first thing and sometimes he was just taking his time coming in. Lately though he had been a lot more punctual as the weight of being the business owner settled onto his shoulders.

He never acted like the spoiled rich kid, although he could have, but in a lot of ways he took for granted the money and lifestyle his father had created for him. When his father passed away the reality of it settled around Stefan like a weighted blanket. It could be a funeral shroud or a thing of comfort and he was still in the process of deciding which it truly was for him. He did seem to take life a lot more seriously now though.

Stefan's office door was closed so I decided not to disturb him straight away and I went about my morning ritual of preparing the office for the day. Turning on my computer, the printer, and most importantly, the coffee machine.

I was walking back to my desk when his office door burst open. He hurriedly stepped out and we almost ran into each other. His eyes flew open and he gasped in shock as he clearly hadn't expected anyone to be standing there right at that moment. I tried to swerve out of the way of the sudden presence in front of me but lost my balance.

I gave the least lady-like squawk possible as I began to go down, only to find myself falling directly into his arm that shot out to catch me.

It was touch and go as I nearly went down anyway but his arm was surprisingly strong as he held pretty much my entire weight for a moment then, as an act of counterbalance, he curled it up scooping me firmly into an unexpected embrace. I felt his chest and arms wrap around me as though it was in slow motion like some ridiculous scene from a Mills and Boon novel, where this would be the moment the roguish pirate/lonely cattle rancher would discover his undying love for the heroine and kiss her firmly. Sadly, this was reality and what actually happened involved more strange squawking sounds from me, followed by the back of my head contacting his nose as he bent forward and I suspect that one of us may have farted from the sudden strain. Not very romantic at all.

Once I had my balance back and was firmly on my own two feet again, trying to blink the stars out of my eyes from the knock to the back of my head, I looked at Stefan. He looked as shell-shocked as I felt. His eyes were slightly crossed and he had a trickle of blood forming under his nose. We looked at each other for a moment, and then both spoke at the same time.

“I'm so sorry.”

“Are you okay?”

I laughed at the absurdity of it all.

“I'm fine, although maybe a little concussed. You need to get a cold cloth on that nose.”

“Huh?”

He touched the bottom of his nose and his finger came away from it bloodied.

“Oh.”

I made my way over to the sink which was primarily used to fill and clean the coffee machine. I grabbed a handful of paper towel and wet it with cold water then turned to hand it to him. He took it and held it to his nose. I was feeling mortified that I had made my boss bleed. Not to mention that it was in such an awkward and inelegant manner. The more I thought about what had just happened the more embarrassed I became. I could still feel every place that he had touched me and the accidental handful of my breast that he had received would not be forgotten in a long time. I could still feel his hand there. Thinking about it made me want him to put it back there. Great now I'm blushing even more.

“Are you okay?”

I asked again, trying to get my brain to function like an actual adult as opposed to a hormone-crazed teenager. He chuckled, obviously remembering the absurdity of the situation himself.

“I'll be fine. Did I hurt you?”

“No, I'm fine, other than being completely mortified at my undignified response to you walking out of your own office.”

He laughed again and this time it was contagious. We both ended up in a giggling fit that was just what we needed, to be honest. He smiled at me and the warmth from his eyes washed over me like a shiver from head to toe. What the fuck is going on here? I asked myself.

“Well, this is a morning to remember,” Stefan said between chuckles.

“Yes, or maybe forget. I'm sorry I scared you. I thought you knew I had arrived.”

“It's quite alright, I was just lost in my own little world and had no idea that time had passed so quickly.”

We both stepped, a little self-consciously, away from each other and straightened our clothing, not that either of us was particularly rumpled from the encounter. I was suddenly very conscious of just how short my skirt was and I tried to tug it down just a little lower. All I really succeeded in doing was drawing his attention to it. Now that he had looked, though, he seemed to be having a hard time looking away. That little tingle went through me again and I smiled to myself as he took a long hard look at my legs.

Jesus, Sam, he's your boss. I thought as I forced myself to move away. I knew he was looking at my ass as I did but I resisted the urge to sway it a little as I walked around my desk. I was surprised at how hard it was to conceal myself and again by how much I enjoyed being looked at like that. I know that some women would be mortified that I enjoyed being objectified like that but I can't help the way it makes me feel and I'll be damned if I will feel ashamed of it.

I could feel myself blushing again as I walked over to my computer and sat down. I began to work, or at least make it look like that's what I was doing as I began going through the morning's e-mails. I tried my best to focus on the task at hand but I was failing miserably. Stefan looked a little lost for a moment as though he had forgotten what he had come out of his office for. He turned and headed back into his office and I tried to slow my heart rate, which had for some reason decided to behave like I had just gone for a run.

It must have been at least an hour later when he came back out of the office and came around my desk. He asked me to bring up some information on my computer so I could discuss it with him. This had never happened in this way before. He had access to exactly the same information that I did and anytime he or his father needed my input into anything I would be summoned into the office. It wasn't profoundly strange to do things this way I guess but it was noticeably different. I brought it up onto the screen and he leaned forward with one hand on the back of my chair and the other on the desk. I caught a whiff of his aftershave and admired his taste.

Although it seemed to be a perfectly legitimate way to look at the monitor, I just knew something was up. He wasn't saying anything and it appeared he was reading what was on the screen but I could have read what was there three times over in that time. I looked at his reflection in the glossy black frame of the monitor and I noticed his eyes were looking down and not at the screen at all. He was staring at my thighs again.

Had he seriously made up this whole scenario just to come look at my legs again? Was he so enraptured by them that he hadn't realised he had taken too long? God, this was driving me nuts. I could feel the presence of his arm so close to the side of my face and I wanted to lean over and touch my cheek to his arm, to feel his skin on mine. I could feel the gentle breeze of his breath eddying over the naked skin of my thighs and it was causing me to heat up. I could feel my pulse hammering in my chest as well as other parts of my body.

He seemed to realise that too much time had elapsed and he leaned forward, changing to the next page of information. Truth be told, neither one of us could have said what was on that page. It could have been the ingredients list of a brand of cat food and we wouldn't have noticed. He moved his arm back to the chair and his fingers brushed past my hair and my ear. It sent an electric thrill through me that I know he must have felt too. I casually leaned back just a little further and forced my legs to relax just a little more. My thighs parted by no more than an inch or two but it also pushed the hem of my skirt just a little higher. I know he noticed because he let out just the tiniest moan of delight.

“Oh.”

He then breathed a rather shaky sigh of appreciation. Like most men, I think he thought he was being subtle and failed spectacularly, but I wasn't about to point it out. It was so unbelievably erotic having him hover over me, quietly moaning his appreciation of my body, smelling his manly scent. I was so turned on that I was beginning to wonder if he could smell the pheromones that were undoubtedly pouring off me right now.

Eventually, the pretence could go on no longer and he moved away. He stood behind my chair for a few moments as we spoke feebly about the information we had just “looked at”, but I couldn't help but wonder why he was hiding behind my chair. Was it because he was blushing or was it something else? I then had a thought that caused another shiver of excitement to run through me. Was he adjusting a hard-on? I hoped he was, the thought was so exciting to me. I wanted to see him grip and adjust it, to wrestle it into a less obvious and slightly more comfortable position but unfortunately, I couldn't see. I would have liked to have helped, gripping it firmly and feeling the heat and hardness through his pants. I doubt it would have helped his comfort much though.

Despite his best efforts to look nonchalant and casual as he made his way back to his office, it was obvious to me that he was keeping his back to me the whole way. He clearly didn't want me to see the reaction I had had on him. I wanted to see though, I wanted to see the bulge in his pants, I wanted to reach out and caress it. I wanted him to touch me too. I wanted to feel his hand between my thighs and stroking over my panties, feeling my heat and the moisture that had begun to leak through.

His office door closed with a click and it seemed to bring me back to reality. I released a huge sigh and realised I had been holding my breath. God, what was coming over me today? I was like a horny teenager again and I was so wet that it was starting to become uncomfortable. I got up from my chair, on legs that felt a little less stable than they should have, and made my way to the toilet. I pulled my underwear down and was surprised to see just how wet my mass of curls had become. I got a wad of toilet paper and began mopping up but I was so sensitive I had to be careful how much pressure I applied.

The last thing I wanted to do was trigger a massive orgasm and moan loud enough for Stefan to hear me cum.

Well, actually that did sound kind of fun, but I didn't think it would be very professional and those boundaries had already been pushed a long way this morning. I completed the task of cleaning up and at the same time confirmed my thought from this morning that I needed to tame the wilds somewhat. I vowed to make an effort to clean up the untamed jungle that was in my panties tonight.

I went back to work and tried my best to be productive but my imagination kept replaying scenes of the morning over and over. The way the stranger on the train and the way that his eyes were practically burning into my barely covered pussy, how sexy I felt as I walked away from him swinging my ass a little more than I usually would, the fact that I could still feel where Stefan's hand held my breast when he caught me this morning. The way he was staring at my thighs and my willingness to show him more. The possibility, probability in my imagination, that he was giving his cock a squeeze directly behind me. All of it kept sneaking back into my imagination every time my focus drifted from the work at hand, which was often.

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Written by yakboy69
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