Chapter 1

There is something almost magical about being able to relax and lie back, after cumming in a hot woman, and then not having to suggest to said hot woman that it might be nice if she sucked your cock to get it hard again. It doesn’t extend my orgasm or anything, but it’s a little like giving my penis a nice massage after all the hard work. Except she’s the one giving the massage.

The “she”, in this case, is named Mandy Potemkin. She’s my executive assistant, not to be confused with ‘secretary’. If I were to make the grievous error of calling the woman assigned from the secretarial pool my ‘secretary’ it would be asking for a complaint to be filed with HR. I know this because it happened to a buddy of mine. I don’t get that. It’s officially called the secretarial pool and, unless the secretary is assigned to one of ten or so people in the company, they are called secretaries. Assign one of them to work for one of those ten or so people, however, and it suddenly calls for a change of title, for some reason. Like I said, I don’t get it, but then there are lots of things I don’t get. Those are things for my executive assistant to ‘get for me’, so to speak. That’s why it’s so difficult to find a good one.

I am a department head in the firm I work for, which means I’m one of the ten or so people I mentioned. The CEO, CFO, and two VPs get to choose their own executive assistants. I presume they get to call them whatever the fuck they want to. We lowly department heads get the luck of the draw, from the secretarial pool. The only advantage I have is that I can get rid of my executive assistant whenever I want, without giving any cause or reason. Working for me doesn’t bring a pay raise, so being sent back to the pool doesn’t affect the income of the woman. The only advantage a woman has working for me is the status among her peers of working for one of the department heads.

This system was established quite intentionally, by the way. The big brass choose their own secretaries, who are separate hires and definitely not pulled from the secretarial pool. But they made sure that none of the women (or men, which is unusual) in our pool could bring expensive litigation against the company for such things as the Me Too movement was based on. In the old days, so I’m told, it was almost routine for a boss to diddle his executive assistant and then send her back to the pool, so he could pick a new one to diddle. That was when a girl did get paid more for working at that level. The girls were at a distinct disadvantage. If one didn’t play ball (or play with his balls) then she got sent back to the pool and lost her raise. If she didn’t want to suck his cock (or maybe swallow), same thing. Won’t allow your boss to bum fuck you? You’re back in the pool and there goes your pay raise.

I’m not saying it was rife, but it definitely happened. The girls weren’t stupid and one of those not-stupid women sued her former boss for getting her pregnant and tossing her aside. She claimed, in court, that she was at a financial disadvantage, caused by him while she was “engaged in her assigned duties”. The company lawyers argued that sex wasn’t one of her “assigned duties”. Her lawyer put two other of this man’s former executive assistants on the stand and they convinced the judge that, if you wanted to keep your job, sex with the boss definitely was one of your official duties. The company lawyers insisted that the only reason she’d been sent back to the pool was because she was pregnant, and that she no longer “fit the profile of a professional young woman”. They also insisted the baby wasn’t his, and actually produced documents in court that said he was sterile, thanks to a vasectomy. The plaintiff knew exactly how many penises had been inside her (one) and that was right about the time paternity tests became something the courts accepted as evidence. The judge set her up for life and further fined the company half a million for submitting false documents to the court. It was actually the “Perp” who provided the false documents (he paid his doctor to manufacture the imaginary vasectomy) and the company just took them at face value. But it was the company that had to pay. The doctor lost his license as well, but that’s a whole different lawsuit.

Obviously this guy lost his job and probably never worked for any of the large companies again. Word gets around about potential problem people like that. The company’s fix to that situation was to ensure that there was no financial gain in working for one of the directors (or any other assignment) and no cut in pay, should your assignment change. The secretary could request reassignment at any time and “personal reasons” was fine as justification. Raises were based on reaching benchmarks based on time of employment, completion of courses and tests, and the like. It was a pain in the ass for the directors, on more than one level, but it solved the company’s problem and that’s all the lawyers cared about.

This is not to say I didn’t dally with the odd executive assistant, now and then. There were unwritten rules, though. For example, it was a no-no to fuck one of the secretaries and then get her assigned as your executive assistant. There was no monetary gain for her if that happened, but there was social status involved, and of course the perceived (whether real or not) perks of working for the boss. I say “unwritten rule” because HR made sure that crap just didn’t happen. The head of HR was a woman named Marjorie Addenhall and she’d been with the company for a hundred years. She’d worked there longer than all but one of the top brass. Marge knew what was going on all over the company and she ran interference on all sorts of potential issues.

Anyway, my former executive assistant (one who didn’t play around with the boss, by the way) got married and quit, so HR knew I needed another one and Mandy’s straw got drawn. The first day she walked into my office, reporting from the secretarial pool, my prick hoped there was potential there, but it seemed unlikely, based on the employee packet that had preceded her arrival at my office.

She was a single mom, for one thing. Such women have (usually) been burned and don’t trust men easily. For another she was a knockout, and beautiful women have learned they have choices in this world. She was thirty-one and probably already had a boyfriend. Still, she was definitely eye candy and would be nice to have around. She stood five-six, which is short next to my six-two frame. She was dressed conservatively, but that couldn’t hide lush breasts and hips just made to carry babies. Her long, flowing hair was that brown with red highlights in it that makes it kind of glow. It was long enough to cover her breasts, but it didn’t hide them, either. Her demeanor was professional but not distant. I detected no interest in me as a man at all. She was wearing glasses and looked (to me) like every man’s dream of a sexy librarian.

So, how did we get from that first day of her walking into my office with me thinking she was in the off-limits category to now, with her lovingly running her tongue over my cock head while holding one hand over her pussy so my seeping cum didn’t drip out onto the bed?

Well, that’s what the rest of this story is about.

If you’ve ever watched a few episodes of M A S * H, then you’re familiar with Radar O’Reilly. He was, basically, the executive assistant to both of the company commanders in the series and his intuition about what his bosses needed was legendary. Mandy could have been nicknamed “Radar”.

She wasn’t insecure, like the MAS*H character, or innocent, but she had an innate sense of what I needed. She was almost rigidly formal in her approach to me, but by the end of the first month, she knew where everything in my office was located. No matter what I asked for, she would tell me exactly where it was or go and get it for me. I worked with a dozen files and projects at a time and she always knew where each set of files were, and what their status was.

I never thought I’d be one of those bosses whose secretary picked up my dry-cleaning and fetched me lunch and such, but somehow, over the course of several more months, that’s exactly what happened. The next thing I knew, she was making reservations for me when I traveled.

It started out business-related; dinner with a client, flight and hotel reservations when I had to attend conferences, things like that. The next thing I knew, she was making reservations for my trips; shows if I was in a place where they were available, cars for my travel away, basically everything I might need or want. She had all my credit card information and kept me straight on the company-related expenses as well as my personal expenses. All this developed within the first four months. It was almost scary how natural it was to rely on her for practically everything.

Then, one time, she overheard me talking to one of the other department heads about a date I had later that week, and how I was looking forward to it and all that. I mentioned that I wanted to impress the woman, who owned a company that had promise as a future vendor for our firm. He asked who she was and what her company did, and I didn’t think a thing about the fact that my executive assistant was quietly filing things nearby.

The next day Mandy approached my desk and handed me a sheet of paper that had the entire itinerary of my date printed on it. She’d made dinner reservations and gotten tickets to a play that was showing at our local art house. She’d even sent flowers to the woman with a card saying, “Looking forward to our date.”

“I took the liberty of setting things up for you,” she said, her face devoid of any emotion. “I hope I didn’t overstep, Sir.”

“No,” I said, trying to cover my surprise. “Not at all. I appreciate your help.”

“I hope the date goes well for you, Sir,” she said, and went back to work.

That was the first time anything personal had come up between us in the months she had been working for me. I’d tried to start conversations, but she seemed uninterested in banter. All she responded with were monosyllabic responses. This was the first time she’d displayed any interest in my private life at all. Assuming you want to call dating someone to cultivate future business opportunities part of my private life.

Two things happened at the eight-month-mark that were rather significant. The first is related to the fact that, at that point, I knew she was divorced and had a soon-to-be-teenaged daughter. I have a photographic memory and remembered seeing that data in her employee packet when she first came to work for me. I also knew that her daughter, Cynthia, had a birthday coming up. So, it seemed perfectly natural to me to buy her a present. The girl was twelve so I didn’t know what was appropriate, but I figured all young girls listened to Adele and got her a CD. I had the store gift wrap it and put it on the corner of my desk the next morning.

When Mandy came in with my coffee I pointed to it and said it was for her daughter. She displayed overt emotion for the first time since I’d met her.

“You didn’t have to do that, Sir,” she said, her voice tight.

“I know,” I said. “I just wanted to.”

“Nobody’s ever paid attention to us like that,” she said.

I thought this was pretty insane, because I knew any man who saw her would “pay attention” to her, and the picture I’d seen on her desk of her daughter showed a cute girl who was going to be a heart-breaker some day.

Mandy tore the paper, as if she were going to open it, and I reached to grip her wrist. This was the first time I’d ever touched her, other than brushing past her.

“That’s for Cynthia, not you,” I scolded.

“How do you know her name?” she asked, staring at where my hand gripped her wrist.

“Well, Mandy, I’m the boss. I know everything,” I quipped.

She looked up at me and into my eyes. I realized she had green eyes at the same time I realized this was the first time our eyes had actually met for any extended period of time.

“Yes, sir,” she said, softly. “I’m sorry, Sir.”

“You don’t have to be sorry. Just put a piece of tape on it and tell her happy birthday for me. It’s an Adele CD, so there shouldn’t be anything inappropriate on it. If there is, let me know what else to get her. It’s no big deal, Mandy. You do a good job for me and I just wanted to get your daughter a little gift for her birthday. Okay?”

“Yes, Sir,” she said, her voice back to the stable, emotionless alto I was so familiar with.

But we had interacted on a personal level. I wouldn’t call it “intimate” exactly, but it was definitely a departure from her normal, stiff, professional attitude when we spoke.

The second and more important event came about a week later, when Mandy came into work actually crying. I had just finished reviewing, editing, and approving a major project the day before, a week ahead of schedule, and given Mandy all the information, both printed and on a thumb drive, to put together into a presentation for the VP of the company. This project involved a contract that, if accepted by the other entity, would net our company several million dollars profit. Projects like that had to be approved by guys at the top. If all worked out, it could mean a little bonus for the contract officer who wrote it, and a nice bonus for me because I supervised him. I know that doesn’t sound fair to people not in the business. Why should the boss get a bigger bonus than the guy who actually did the work? Because that’s just how it works. It’s one of the perks of being a boss. If you don’t like it, then figure out how to become the boss.

Anyway, she was crying because the vast majority of the work had been destroyed. Most of my notes were gone. I use a fountain pen, because I just like the feel of it, but the ink is water soluble. The memory stick with the data charts was unusable and the sketches of several proposals were stained and torn.

It started the previous evening when it was raining and someone had accidentally knocked the file out of her hands on her way home from work and the wind distributed things on the sidewalk for the rain to soak. A passing skateboard had trashed the thumb drive before she could pick it up. The crowning blow had been when a bowl of tomato soup tipped onto what was laid out to dry.

It wasn’t the disaster she thought it was, actually. The electronic data was on my computer at work. It just needed a final edit and colors confirmed and that kind of thing. The notes had been my instructions to her on what I wanted her to do. The biggest problem was the sketches, which could be reconstructed in a couple of days, but needed to go to the art department for final production. That would mean getting them bumped to the front of the line in the art department when they were ready again, but I had the clout for that kind of thing. All in all, instead of being a week ahead of schedule, I would be just-on-time. I tried to explain this to Mandy, but she seemed to be on the verge of a complete collapse.

She needed to stop crying and get back to work on this, but all she wanted to do was moan and groan. I finally lost my patience and snapped at her. Thankfully, the door was closed so nobody outside heard it. I gripped her shoulders and basically shook her.

“Knock it off!” I yelled. She went white and stared at me through tear-filled eyes. I have no idea where the next part came from. I guess it just felt right, but what came out of my mouth was something I’d never said to a woman. “If you want me to beat you, I’ll do that later this afternoon! Right now I need you to focus and help me start putting the presentation back together.”

I immediately knew, of course, that I had crossed the line. These days the boss doesn’t offer to beat the help. At a minimum I could expect to be visited by a stern-faced Marge from HR, asking me just what the hell I thought I was doing. More worrisome was the potential for a lawsuit. Her response, however, was both odd and comforting, because she didn’t act like she thought it was inappropriate at all. In fact, it seemed to be exactly what she needed. She stopped crying, gathered her composure, looked me in the eye, and said, “Yes, sir. Right away, Sir.” Turning around, she walked out of my office to her desk and for the rest of the day she had her nose to the grindstone. By the end of the day, between the two of us, we were probably more than halfway to where we needed to be. We had only worked maybe an hour overtime when I started my routine of preparing to leave. Mandy had hung in there with me, which was great. Most of the rest of the office workers were gone. When Mandy walked in and stood in front of my desk. Her eyes were downcast. Her arms hung like they were paralyzed and she couldn’t move them. I knew she’d been working her ass off to repair things, so I tried a little levity to tell her everything was okay.

“Are you here for your beating?” I joked.

“Yes, sir.”

I was smiling. She, however, was not. I’m usually pretty adaptable but I have to admit her response surprised me. She wasn’t joking! So I stopped what I was doing and gave her my full, undivided attention. Unbidden came images in my mind of this lush beauty over my lap with her fine ass exposed while I smacked it with my hand. I felt my cock start to stiffen.

Looking down at my desk, she started in her soft voice. “I know I should be fired for what I did, and if I had any self-respect at all, I’d quit for having ruined your project. But I need this job. I have to have it. But I also know I should be punished. So if you want to beat me, I’m ready.”

Right. I was back to seeing those flashes of lawsuits. Maybe I had it all wrong. Maybe it was something else... “Blackmail” is such an ugly word...

“Mandy, I was just joking. There’s no way...” She cut me off.

“No, sir! What I did was careless and unacceptable and I must be punished. I know you could fire me, or at the very least you should dock my pay, but I can’t afford that. I’ll work this weekend without being on the clock, but please do something other than docking my pay. What I did was unprofessional and negligent. I failed to take proper care of such an important project. A child could have taken better care of it so it’s only right that I receive the punishment of a child. I must be disciplined.”

The first thing I thought of was that she’d already been on unpaid overtime when she took things home to work on them. She didn’t seem to realize that, but even if she had I don’t think it would have made any difference. The second thing I thought of was a time in my youth when I’d done something wrong (can’t even remember what it was, now) and my father gave me the choice of being grounded for a month, or a session with his belt. I’d chosen the belt, because that would be done and over with in a very short time; much shorter than a month of boredom and missing being with my friends. I also remembered that I’d felt guilty about whatever it was I’d done, and I didn’t remember the whipping being unfair at all.

I came to the sudden realization this wasn’t for me; it was for her. She needed absolution.

“All right, Mandy, if you think that’s what’s necessary. But this is neither the time, nor the place. Go gather your things, get your car, and follow me to my place where we can continue this conversation. I don’t need any late workers or the night janitor hearing my hand smacking against your ass.”

“I-I ... didn’t think ... I’m so stupid...”

She stood there babbling. This girl had no self-esteem what-so-ever. She had just told me I could... should beat her and now was apologizing to me because she hadn’t thought about the rest of the office hearing me beat her. My cock was so hard I thought I would pass out from the blood-loss.

“Sir?” she said meekly, “I don’t have a car. I take the bus into work every day.”

Sometimes, I’m such a retard. Here she had worked for me for nearly a year and I had no idea she didn’t even own a car. How was she going nearly every day to get me lunch, do my shopping, get my laundry if she didn’t own a car? There’s your all-knowing boss for you. I felt guilty, and then I felt guilty for not feeling guilty enough.

“You don’t own a car,” I said, leadenly. On reflection, I realize it might have sounded like I meant, “You’ve got to be fucking with me. Who doesn’t own a car?” I wasn’t sure what my tone of voice might have added. She didn’t bat an eyelash, though.

She was barely whispering. “No, sir. I’m sorry. I – I – the insurance is so expensive and...” I held up a hand to stop her.

At this point I was angry. Okay, not angry, exactly, but miffed. If that sounds strange, it was. There I was, feeling guilty and stupid and, for some reason, I blamed that on her! I knew that wasn’t fair. I knew that in that very moment. But she had taken me out of my comfort zone and was now demanding I do something I’d never done before. Well, if she wanted to be punished, then I was going to fucking punish her!

“Get your things and be ready to go in five minutes. You’ll ride home with me and I’ll put you in a taxi when I’m finished with you.”

“I’ll pay you back for the taxi...” she trailed off.

“You will do exactly as you are told to, and nothing more!” I snapped. “I think we’ve already established that you can’t afford a taxi.”

So far, there had been no real indiscretion in all of this. Ok, maybe the part about the beating was, at the least, a faux pas, but we really hadn’t crossed the line of no return ... yet.

“If you feel obligated to pay me back for the taxi, then you’ll do what I tell you, when I tell you,” I added.

“Anything you say, Sir,” she whispered.

That’s a culturally-charged phrase, at least in Western society. Anything? It was at this point that the train started rocking on the rails. Truth be told, I’m a little fascinated by the whole BDSM thing. I’ve never engaged in that sort of behavior, but I’ve read stories about it. Most of them involve ... sex. This might get me an opportunity to explore a little, but I also knew I needed to be careful. She seemed willing to submit but at the same time, I wanted to leave her an out, in case she changed her mind somewhere along the way. I thought I would take her home, slap her ass a few times, and maybe, just maybe, get to play with her a little bit before I put her in a taxi.

I would worry about the awkwardness of tomorrow morning tomorrow morning. As the old saying goes, there’s only enough blood in a man’s body to run one head at a time, and right now, my little friend started doing all of my thinking for me.