Encountering Alexandria

This is my entry in the 2022 On The Job story event.

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Masturbating at work, especially in an office, is usually a bad idea and I always knew it. However, when I was twenty-six I fell into the habit anyway.

There were some reasons, or rather excuses, for that happening. For one thing, I had been separated from my wife for months and I had found no new sexual outlet. Meanwhile, I had opportunities at my office to jerk on myself because of the highly irregular hours I had. There were vast amounts of unpaid overtime -- I was considered an "exempt" employee with a salary who was not entitled to extra pay.

Maybe I felt that I had been scammed by this rule, which encouraged me to vent my displeasure at the company. Spilling my seed on the office floors was like a form of revenge. There was certainly something obsessive about my activities, although I also enjoyed seeing how much I could get away with.

This was occurring at a northern New Jersey publishing company starting early in 1986. The location was one of those white concrete pillbox office buildings that were springing up along all the major roads.

Anyway, I started doing it standing up in a stall in a men's room, much like I had done at college a few years earlier. Other employees were often in the same overtime predicament as I was in, but there were times when I'd be there alone late in the evening or on a weekend.

I grew bolder in where I would go when pleasuring myself. It probably wasn't truly horniness per se. Maybe I just got a kick out of being "naughty," although some people might have said I was being "degenerate." On some level, I was bothered by it, and I did feel some guilt, but I couldn't seem to stop myself. It became an obsession that I would indulge in perhaps once or twice per week if I could.

My onanistic activities eventually moved into the office space proper. First, it would be in the conference room or the little lounge next to it. Then I got weirder, and I moved on to the personal spaces of some of the female employees -- either on the floors of their offices, which were never locked or, for the lower ranking ones, in their cubicles. I would kneel down and experience the throes of pleasure as I sprayed my load onto their carpets.

Then I would blot up the sticky mess as best I could, but that was the extent of my cleaning. No one ever noticed the dried remains the next day; I doubt that any of them could imagine that someone would do such a thing in their spaces. Then, the carpets would get their weekly cleaning and remove the last of the evidence.

Sometimes I would imagine the woman whose area I was invading, which gave an added sense of frisson to my secret activities. One of my favorites was a trim, young blonde wife named Anita, who sat in the cubicle on the far side of my own wall.

My fantasies about her were the most elaborate I had at that office. I would imagine spanking her over my knee as I sat in her chair. Anita, you've been a very bad employee, you need to be firmly disciplined. After smacking her tight little ass, I could see myself coupling with her vigorously as she sat on her desk and I stood between her splayed legs. That's what these young ladies need, a little punishment and quite a bit of intense fucking.

Speaking of young women, I found that the desk drawer of one of them contained a bottle of hand cream. If I was there at night and I had forgotten to bring Vaseline, I would borrow her cream. Maybe she was puzzled by the depletion of her bottle, but who can say for sure?

Somehow, for months, I never got caught. The one time someone did come in the front door, their view was blocked by the cubicle walls. I carefully sneaked out, walked around the back, and then gave a perfunctory greeting to that other employee.

During this period, my supervisor was a thirty-five-year-old woman named Linda. She had hired me, and we got along very well. I'm sure she had no idea what I was doing during those off-hours. I respected her and thus I never went into her office for one of my self-banging sessions.

After about ten months, she landed another job and was ready to move on. While Linda was finishing her two-week interim period, I heard that another woman had been hired to replace her. I knew that this would result in a tricky situation for me.

From what I had experienced a couple of times before, the new person might be suspicious of people she hadn't picked herself. Thus I'd have to carefully assess that new boss and make the necessary adjustments.

One Monday morning I thus met Alexandria. She looked like an Alexandria, but fortunately, she wanted to be called Alex.

I could tell right away that she wasn't exactly an ebullient person. It was difficult to say if she was a bit severe or merely quiet. In any case, she was definitely very business-like and discussed almost nothing beyond what was necessary to get the job done. For the next eight months, she rarely talked about anything personal, and she didn't seem to exhibit any of the sense of humor that Linda had shown.

Alex was about forty -- I later found out it was forty-one -- and my impression of her was that she was, well, a very respectable lady. She had close-cut dark blonde hair, and she was fairly tall and a bit on the slender side. Her glasses had dark rectangular frames, and she was always well-dressed, usually with a suit or jacket and skirt combination almost every day.

I didn't pick up any sexual vibe from her whatsoever. Instead, I could imagine her as the vice-principal at a school somewhere. It was not that she was unattractive but she was surely too old for me. Her emotional reserve was another hindrance to any potential interest I might have had for her.

"Prim and proper;" that was the way she once described herself much later. Actually, she had meant it as how I saw her; she guessed what I had been thinking. Of course, she never mentioned it until one fateful evening in September, 1987. That was when I found out that I had very much underestimated her.

However, in the meantime, she didn't give me any problems at work, which was the main thing that had concerned me. Perhaps I was glad that she wasn't a distraction, as a couple of the younger women at that place had become for me. Mostly I dealt with her as a boss and then I forgot about her after I had left for the day. I assumed she also had forgotten about me. If she had any womanly appeal, it was completely invisible to me.

As the months went by, I learned nothing about her life, and the only thing she knew about me was that I was separated from my wife. I don't think she even knew the name of my ex. On my side, I didn't know that she was divorced herself.

Meanwhile, if no one else was present, I'd continue my strange nighttime and weekend rituals. One night, it must have been close to 9:00 PM, I walked passed Alex's closed door. I knew she never locked it, but I knocked on it anyway just to be sure.

When there was no answer, I pushed it open. It was very unlikely that she'd be in there, but if she was, I could always come up with some pretext, some work-related question I could talk to her about.

There was no Alex there, but it did seem appealingly weird to actually kneel and masturbate on her floor and leave my semen there.

Why I had to do that -- well, I haven't yet explained my own motivations very well. Probably I didn't want to think about those too closely. It must have had something to do with being strange for its own sake. I had no issues or grudges against Alex at all. Yet we all have a dark side, I suppose, and what I was going to do seemed relatively harmless.

And when I got back there a minute later with some purloined hand lotion, I didn't fantasize about her. In fact, I never had imagined anything sexual about Alex. So I closed the door and I got busy with one of my Anita scenarios.

Just as I was getting some momentum going, a scene from a nightmare unfolded. I heard someone pull the handle on the outside of the door and undo the latch. The door opened and of course, in walked my boss Alex.

I was in such a frantic panic to get up and get my pants buckled that her demeanor didn't register with me. I was saying something like, "Please, I'm sorry, I know my judgment was terrible, I'll quit right now if you want me too . . ."

She didn't react as I expected, but I barely noticed that. As she closed the door, she put a hand up and said, "Take it easy, calm down. And don't pull your pants up just yet."

I couldn't make sense of what she had said. I came up with, "Don't toy with me if you're going to fire me. But I'm truly sorry, it was a very stupid thing do." Yet I left my pants down merely because she had told me to do that.

Alex walked right past me, inches away, and I heard her say, "You're not going to get fired. I know it's a shock, but try to relax a bit."

Her voice was quite calm. I thought, she's cleverly trying to humiliate me before she drops the hammer on my pathetic self. I would have preferred, perhaps, if she had shown how upset she must have been. I was certainly upset, and I was trying to preserve some minimum amount of dignity in that difficult situation. Yet I was babbling something that I don't remember now.

I barely noticed that she didn't sit behind her desk, but she got up on the credenza along the back wall and sat on it. It struck me that she was looking at my crotch with something like curiosity.

"Alex, can I please buckle my pants now?" I didn't deserve mercy but I was asking for it anyway.

She hesitated for a moment and continued to look at me. Then she said, "Okay, there's no point in humiliating you. I admit I was just checking out your -- well, I was looking at your erection." I caught a smirk on her face. "You can pull your pants up and sit in the chair."

Her statement about looking at my cock didn't make sense to me except as further humiliation and thus I discounted it. Anyway, she was referring to the usual chair in front of her desk that I used when I was in there for some discussion. In a dream-like way, it seemed like I was sitting in it without having to walk the couple of steps to get over there.

For a second I wondered if it was even worth trying to save my job after what had just happened. I didn't want to ever see Alex again, but I also needed the salary I was getting. Jesus, I've truly fucked up this whole thing up beyond belief.

I still wasn't fully comprehending what she was saying. "I wish I could offer you a soda or water, but I don't have any in here." What is this lady going on about? Why isn't she showing how angry she is with me?

Instead, she pushed the glasses to the top of her head and leaned forward a bit. "When I don't have my glasses on, I'm as blind as a bat. Hm, that was kind of trite. Anyway, Jake, look at me; I mean really look at me."

I expressed my bafflement. "Why should I do that?"

"Because I feel like you've never really seen me before."

I dared say, "Well, why do you care? You're just my boss." It was very strange that she hadn't yet said much about catching me whacking off on her office floor. Yet she had had all the leverage in that situation, so I looked at her as she requested. It seemed I had little left to lose at that point.

She was, of course, wearing the same clothes I had seen her in earlier that day. The whole outfit was very tasteful, as Alex usually looked: a black jacket, white blouse, a dark skirt with subtle stripes, dark nylons, and black shoes. Her hands were folded in her lap.

I dared look at her face, and it was difficult in my state to assess her expression. She did seem quite composed, yet also slightly bemused. I still imagined that she was playing an elaborate game with me. "Okay, now I've looked at you. So what?"

"And what did you see?"

What was I supposed to say to that? I saw the usual, the very respectable woman in her early middle age who I had known for eight months. And my entire livelihood was in her hands at that moment.

I came up with, "I don't know, the same as usual I suppose. As I said, you're just my boss." I wanted to add, man, I'm in such trouble now, but that was already so obvious.

She moved down to her usual position in the chair behind the desk. "I'd like to talk to you a bit if you don't mind."

Do I have any choice but to listen to what she has to say? She must be incredibly crafty to pull off the act that she's doing right now. I decided it was worth complaining a little bit, because how much worse could things get?

"Frankly, I'd like to get out of here right now, and maybe never come back."

"Look, would you like a drink, I mean a real drink?"

"What is a real drink?"

"You know what I mean; I mean this." She opened her desk drawer and took out a pint bottle of bourbon and a couple of plastic cups. "I assume you want me to pour you one too?"

My only thought was, a condemned man is owed a final drink before he is shot. I figured I had to say my piece. "Please, don't mess with me. If you must let me go, then let me resign. I need to collect unemployment; I need a good job reference from here."

"Just stick around a bit; have your drink. I'm not going to give you a hard time, I'm just going to ask you a couple of questions." She had the advantage in that situation, and I couldn't just leave until she gave me permission to go. I felt like yelling, just get it over with, whatever it is.

Instead, she said, "I know you've been separated from your wife for about a year now."

"Yes, but you already knew that."

"But have you dated anybody in that year?"

Why was that any of her business? I answered honestly anyway because I felt I had to, "No, I haven't been with anybody since then." My bourbon was going down quite smoothly. Anything to calm my anxiety at that point was worth having.

"I'll tell you something about myself. I'm forty-one, and I've been divorced for three years now. I haven't been out with anyone in that time either."

I almost said, well, why not? but I held it back. She looked down at her drink and she told me anyway, "I don't know, it just seems that at my age men, whoever they are, no longer take me seriously. You must know yourself what it is like to be lonely too, right?"

"Well, yeah, sure." Where the hell is she going with this?

She seemed to pause so she could get her courage up. Then she looked at me and asked, "Do you know what I thought when I first walked in here?"

"I couldn't imagine it."

Alex had more of her drink, then she giggled a bit. "I thought, that is certainly a nice big cock. I think you were getting close to an orgasm, too."

What, is this lady some connoisseur of male organs? I had to know what she was getting at. "Alex, what are you talking about, what do you want from me?"

For the first time, she looked nervous, maybe shy even. She folded her hands on her desk and said, very quietly, "This is a little difficult for me to talk about."

I thought, this is a little difficult to listen to. You have my full attention now, so please get it out. She almost whispered it, "We could give each other some pleasure, you know what I mean."

I guessed why she had wanted me to look at her so closely before; she wanted me to assess her attractiveness. She was uncertain about herself, so she said, "Do you think I'm too old for you?"

As if that had anything to do with the mess I was in. An indirect answer came to my mind. "I get the feeling if you were twenty-seven right now, you probably wouldn't have anything to do with me." Maybe that was a little too much honesty on my part.

Yet I tried to imagine her at my age. She probably had looked very good then but perhaps she had been a bit haughty too. Young women had higher opinions of themselves, I assumed. She probably would have thought she could have done better than me, but then where was that ex-husband now?

"But I'm not twenty-seven now; that was a long time ago." She thought further, "Maybe you think I'm blackmailing you. But, really, I have thought about you at times."

I still couldn't fully grasp what she meant. "I thought it was mostly men who blackmailed women. But, no Alex, I don't have a clue as to what you're trying to do right now."

Then I started to put it together. Is she going to make me an offer I can't refuse? "Did I hear you right? That we should pleasure each other?" Some anger rose in me. "You're messing with me, aren't you?" Even if she was justified in doing that, I still didn't like being the target.

I let my comment hang there, and she was now the one looking embarrassed. She leaned forward and continued in that low voice she was using. "As I said, this is difficult for me to talk about. But no, I'm not kidding you."

It was all her game at that point, so I sat there and waited for more. And in a moment she somehow became articulate about her thoughts.

"What I meant -- I mean, what I propose is that, first, you go down on me. I can sit right on the credenza there. Then, I could blow you, but you have that Vaseline or hand cream or whatever it is on you; I noticed it. Thus I'll just stroke you with my hands until you come. You must be pretty charged up from your own attempt on yourself."

It suddenly seemed irrelevant if that was blackmail or not. Maybe she was indeed offering me a way out of the screw-up I had gotten myself into. When I didn't respond, she said, "How does that sound?" She was actually smiling at that point.

This lady has some moxie I've never seen before. And maybe she's pretty horny herself. Maybe I was a bit rude but I was desperate. "All right, when and where is this supposed to happen?"

"Right here, right now. And I'm sure you are going to like it. All that I ask is that you try to please me, and I will try to please you." She frowned at me, but it wasn't because of anger. She was puzzled I think by her own reactions.

Then she said, "Maybe you need some encouragement. Here, let me show you something." With that, she sat back and took her jacket off, draping it over the back of her chair. Then she pulled her white blouse over her head, and dropped it on her desktop. She wasn't wearing a bra, and she immediately commented on that. "As you can see, my breasts are not that big, so sometimes I skip having a brasserie on."

I was starting to believe that this lady, although she was probably more than a bit eccentric, was definitely not kidding me. Yet I still pondered if I had any choice in the matter.

"Here, I'll show you more." She got up and took her dark skirt off, leaving that on the floor. Her stockings were thigh-high, and her panties were skimpy nylon I supposed. They were of a shiny, silvery color.

"Pretty good, right? And I assume you'd like to see my pussy now too."

I attempted joshing with her. "If you want to show it, then I guess I'll look."

Alex took her panties off and tossed them at me. Her aim was pretty good, and they bounced off my chest. Without thinking about it, I caught them with my hands as they fell.

Meanwhile, she had hopped back on her credenza; she put her feet up on it and spread her legs. Her hands went down and spread her lips apart. "You don't have to put a bag over my head, now do you?"

A thought occurred to me, I guess forty-one-year-old pussy is better than no pussy at all. That wasn't a particularly kind thought, so I let her have the next word.

"I'm sure you must know how to lick a woman to orgasm, don't you?"

I was trying to get my mind in order. My anxiety about being caught jerking off was still there, but it was now mixed with excitement about getting her off. It was starting to look like a pretty good deal to save my job. "Yes, I've certainly done that before."