by Jessica Sin
“You really do look great,” I replied honestly.
“Thanks,” she smiled. “You know, I’m actually warming up to the idea of us working together, even though you get to be my boss. So I think it’s a great thing that we can spend so much time together.”
“Yeah. You’re right.”
“What’s the matter?” she asked with a concerned look on her face. “Are you starting to have second thoughts about this?”
“No, it’s not that. It’s just that…nevermind…it’s nothing.”
She put her hands on her waist and gave me that stern look. “Don’t give me that ‘nevermind’ stuff young man. I know when something is wrong. So tell me, what is it?”
I took a deep breath. “Fine, do you know a guy named Dave from human resources?”
“Sure I do. Why?”
“He dropped by to talk to me…and…well…let’s just say that he didn’t know that I’m your friend when he was telling me about your encounters with your previous boss…”
“Oh my god…” she gasped. “That fucking jerk. I…I can’t believe this.”
“So it’s true then?”
She paused for a brief moment. “I’m not a whore. So please don’t think of me as one.”
“I never said you were.”
“No, but you were thinking it. I’m a grown woman. Who I have a relationship with, and what I do in that relationship is certainly nobody’s business. So as far as I’m concerned, you have no right to judge me.”
I took a few steps forward and put my hand on her shoulder in an attempt to comfort her.
“I’m not judging you. And you know that I would never think any less of you for any reason. It’s just that, I was surprised to hear that I couldn’t stop thinking about it. That’s all.”
“Fair enough,” she replied. “But please don’t think that I’d slept my way to the top or anything like that. I’m a hard working woman who has had to work for everything she has in life.”
“That never even crossed my mind. You’re the most dedicated and respectable woman I’ve never known,” I replied honestly. “But I have to ask, did the relationship you have with your old boss happen while you were still with your ex husband?”
A sudden look of shock came over her face. “God no! I’ve never cheated on him, and this has absolutely nothing to do with us splitting up. It was only a short fling I had when I was single.”
“Thank you. I’m glad to hear that because that was what really bothered me more than anything.”
She smiled, “Well I’m sorry I overreacted. But since we’ll be working together, I think it’s best if we just clear the air right now and get it over with. The relationship I had with my ex-boss began over a year after I became single. I was constantly busy with my personal life and career. I worked very long hours, and he was the only man available to me and we slowly developed a mutual attraction. Plus I’ve always had a thing for authoritarian figures which made him even more attractive.”
“A thing for ‘authoritarian figures’ huh? If I remember correctly, didn’t you first meet your husband when you used to work for him at another company?”
She flashed a serious look. “Don’t get cute mister. But you’re right, I used to work for him and that’s how we met. Like I said, I’ve always had a thing for authoritarian figures in my life. It’s my only weakness. So now you can stop wondering what this was all about.”
***
There was a slight tension between us that night, but it eventually faded away and everything was back to normal.
But I still couldn’t get over the fact that it was the first time she had ever mentioned anything about her closely guarded sex life. It felt as though layers were being peeled off the person I was most closest to in my life.
***AN INTERESTING DAY***
It was the first day that Sandra and I would be heading to the office together with me being her boss. I still wasn’t exactly sure how she would handle it, but by that morning, she had become very enthusiastic.
“I’m so excited!” she exclaimed with a cup of coffee on hand.
I couldn’t help but notice how beautiful she looked- beaming with pride and dressed especially prim & proper. She was back to her old classy self again with the way she looked.
“Yeah, well it’s defiantly going to be an interesting day,” I replied, smiling back at her. “The fact that we’d be working together still hasn’t fully sunk yet to be honest.”
“I know how you feel. And you better not abuse your powers either,” she replied playfully. “Believe me, you might be my new boss in the workplace, but I’ll always be the boss when we’re out of the office.”
“You know, that part hasn’t really sunk in yet either. It might actually be fun bossing you around for a change,” I joked.
She suddenly put her coffee down and gave me a serious look.
“Look…there’s something else I’ve been meaning to tell you. Aside from some of the other managers there and a few of my close friends, no one else knows that you’re my friend, and I’d like to keep it that way. I’ve gotten over the fact that I’ll be working for you, but it’s still kind of humiliating to me if other people found out about that. I’m still a proud woman you know.”
“I’m sure I’d feel the same way if I were in your shoes. So if you work hard and do what I say in the office, I’ll be sure to keep this little secret between us.”
A look of humility with a hint of embarrassment crept over her face. “You’re obviously starting to enjoy this aren’t you? At the end of the day, just remember who you’re talking to young man.”
***TREAT ME LIKE YOUR OLD BOSS***
A few hours had passed and I was sitting behind the desk of my office. It felt good being in charge, and not having to take orders from some guy who shamelessly steals other people’s ideas and hard work. Instead, I just have to report back to upper-management every so often. Plus I would be making more money
Knock! Knock!
Sandra opened the door and came inside with a smile.
“Hey boss,” she said playfully while walking towards me. “Can I get you coffee or something? I can’t stand the thought of you being overworked siting behind that cozy desk of yours.”
“Your sarcasm is much appreciated. Don’t you know it’s bad practice to be condescending to your work place superior?” I replied.
She sat on my desk and continued her playful demeanor. “I guess not. But the reason I stopped by is because me and a few of my old colleagues are going out to eat together. We haven’t seen each other in a while so my lunch break will probably be a little longer than it should. It won’t happen again- I promise.”
“I knew you couldn’t resist taking advantage of me,” I replied giving her stern but equally joking look. “I just didn’t think it would be this soon. I mean, we’ve only been working together for a few hours now.”
“Oh relax sweetheart. It’s only an extra thirty minutes. Besides, I’m one of the more experienced employees around here when it comes to paralegal work, so I can get things done in a fraction of the time compared to anyone else.”
“I’m sure you can. But I still fully expect to be treated like any one of your previous bosses,” I said before immediately realizing what that meant to her.
Both of her eyebrows raised and she gave me a sly look. “Sooo…after everything you know, you still want me to treat you like one of my previous bosses huh? That’s quite a revelation, especially considering how I told you some pretty intimate things.”
“Oh come on…You know exactly what I mean. I meant that…”
She continued, “Now when you say that you want me to treat you like my old boss, did you mean how submissive and naughty I could be behind closed doors? Because that’s what your comment sounded like to me.”
“Has anyone seen Sandra?” a voice said distantly in the background.
“Sounds like your friend is looking for you. I don’t have a problem with you taking a little
longer on your lunch break. Like you said, you’re one of the best and hardest working people here.”
She smiled and turned to leave. “I knew you’d see things my way.”
***HAVE YOU EVER THOUGHT ABOUT ME?***
After a slightly awkward car ride home, she and I had dinner that evening together. None of us mentioned the innuendo filled discussion we had early in the day, but it was clearly still in the air.
“So what do you think about this pizza?” she asked, breaking the silence at the diner table.
“It’s bread with a little tomato sauce and cheese on it,” I replied. “It’s good, but it’s also crazy how some places in the downtown area can get away with charging some outrageous prices for something that costs only a small fraction to make.”
She flashed a look, “You’re starting to sound like a manager already. You should fit right in over there.”
“Well that’s the idea. Speaking of which, we should really put this awkwardness behind us. I mean, I’m sure we’re both thinking the same thing right now aren’t we?”
“You’re right,” she said. “I’m sorry for getting a little too playful with you earlier. I was having a good time with old friends and I guess I got a little carried away in your office. So, I’m sorry again if I weirded you out in any way.”
“It wasn’t that weird. It’s just that you caught me totally off guard and I didn’t know how to react. Well, to be honest, I thought it was actually kind of funny to hear you talk like that. You’re always so proper and elegant when you’re out in public, so it was fun seeing a lighter side of you for a change.”
“So I take it you liked it then?” she teased.
“Oh no, not this again,” I jokingly sighed.
“I’m being serious here. You really don’t have anything to be ashamed of. It’s a lot more accepted in this day and age.”
I shook my head, “Huh? Wait…are we still talking about the same thing here? Because if I didn’t know any better, I’d swear that you’re asking me about…”
“Incest,” she blurted out. “Have you ever thought about me?”
“What? Heck no! What kind of sick pervert do you think I am? How could you ask me something like that?”
“Curiosity I suppose,” she said with a shrug, like it was no big deal. “I read a lot of romance stories online and I’m often surprised by the large fan base that that kind of thing has. I’ve been extremely honest with you lately, so you can be honest with me; have you ever thought about it?”
“I’ll answer your question on one condition,” I said firmly.
Her eyebrow raised. “And what condition would that be?”
“I can’t stop thinking about what you said in the office today, about how you did things that were ‘submissive and naughty’ with your last boss. And by the look you’re giving me, I think you already know what I’m going to ask.”
A sly and slightly embarrassed expression crept over her face. “Fine…I’ll go first. You might already know by now that I had a certain liking for oral sex with my previous boss in his office. As for the ‘submissive and naughty’ part, I used to do different things that he’d ask of me, things that turned both of us on to no end.”
“Like?”
“Like I used to occasionally go pantyless to work. He would call me in to his office, have me sit on his desk, and make me lift up my skirt to show him how I felt about it. That usually ended with me having to wipe his desk clean. In addition to me giving him oral sex, he would sometimes screw me in the supply room. And finally, if we worked overtime together, he would insist that I strip down and do my paralegal duties in the nude. And that meant that I had to walk around the office completely naked. There have been several instances where the custodian has gotten quite a show.”
“Well that was a more that I was expecting to hear,” I replied, feeling stunned by her admissions.
She shrugged, “You asked for it. But now it’s your turn. I have bent over backwards trying to be completely honest with you since you found out about my private endeavors, and I expect some reciprocation. So…have you ever thought about incest?”
“I guess.”
“That short answer better be a joke young man,” she said with her eyes becoming wide and her anger building. “I mean it, you may be the boss at work, but I’m still the boss at home. So start talking mister.”
“Okay okay, it was a joke,” I replied with a laugh. “But to your question, yes, I have. Who hasn’t? I may have even visited some of the same sites you go to on occasions. So I’m not surprised that it has a large fan base, and it’s probably a lot more popular as a fantasy than people think.”
An amused look came over her face. “Well what’s your favorite category? What excites you the most?”
“Do we really need to go there? I should have known this was a set up. This is your way of embarrassing me for being your boss isn’t it? I just knew it.”
She laughed, “Relax sweetie. Believe it or not, I actually do like that you’re my new boss. And thinking about me in that way is really nothing to be ashamed of. Like you said, this kind of thing is more common than people realize.”
I paused for a moment, “…Well…in that case…I may have thought about you in ‘that way’ once or twice in my life- maybe a little more. Can you blame me? Friend or not, you’re a beautiful woman.”
“I’m flattered that a vibrant and healthy young man would say that about me,” she said graciously.
“So what about you?” I asked. “What kind of stuff do you like to read? Are there any particular fantasies you like to think about?”
“What do I think about? Right now I think I could use a warm bath with some light music to unwind after a long day. Maybe a little television afterwards and then it’s off to bed.”
“That’s not a bad idea. If I’m not mistaken, you owe me some paperwork tomorrow,” I replied.
She smiled, winked, and got up to give me a kiss on the forehead before leaving.
***OFFICE RELIEF & PROPER HOUSEWIFE***
It was late the next afternoon when Sandra knocked on my office door, carrying some documents in a folder. She looked gorgeous as always. Her hair and make-up were done to perfection like usual, and so was her professional attire. But unlike yesterday, instead of wearing pants, she wore a knee-length office skirt with stockings on her legs which could grab any man’s attention.
“Good afternoon boss,” she said with grace and class. “I have the briefing you wanted, complete with detailed information and research I added on my own.”
“And that’s why you’re the most dedicated and valuable person in this division,” I said honestly. “I’ll be sure to recommend a pay raise for you once evaluations come. You deserve it.”
It was obvious that she felt proud of what I said, and it made her stand a little straighter and hold her head up a little higher.
“Thank you sir. I do appreciate it. And speaking of dedication and hard work, you look exhausted. Don’t let the pressure of a new job get to you. It’s always good to have a nice break every now and then to cool off. Trust me on that.”
“Yeah, well this job ain’t easy. It pays well, but of course that means upper-management expects good results. Thanks for caring though.”
She casually walked over to where I sat and leaned her backside against my desk. Her face showed a touch of excitement and her skirt rode up slightly, and I was in anticipation over where this was headed.
“I saw you glancing at my legs a few times in the car this morning,” she said with a hint of seduction. “I don’t think that’s ever happened before. Did you see anything you like? Or did you remember what I said about wearing a skirt for my ex-boss?”
I gulped and nervously replied, “Both maybe. What you did for your previous boss crossed my mind when I saw you were wearing a skirt. Plus you have great legs if you don’t mind me saying so.”
She reached down with both hands to pinch the sides of her skirt, and she slowly raised
them to reveal the flesh of her thighs and the top of her garter.
“I’m glad you think so. You know, when I got dressed this morning, I realized that I never answered your question about if I had any fantasies of my own. So maybe this may give you an idea…”
With that said, she pulled her skirt up even further to reveal the bottom end of her bare vagina to me in my office. My heart was pounding at the sight of her labia. She pulled even further fully expose her cleanly shaven crotch. If things weren’t hot enough, she sat on my desk and spread her legs apart, putting her dripping wet pink flesh on full display for my viewing pleasure.
