Somewhat Like the Intern

So, one day, while idly looking at some help wanted ads, I came across something rather interesting: It was for a personal assistant. The ad said that personality would be valued over experience. It said neatness, and impeccable manners were required. Well, that's me - when I'm not welding, I mean. I didn't really quite know what a personal assistant is, but since no experience was required, I went ahead and applied. I was interviewed by a twenty-something woman who asked a bunch of generalized questions, some of which I think are illegal to ask, like, What's my religion? In any case, I seemed to satisfy her, because she took me to a waiting room and told me "Miss Quan" would be with me shortly. I didn't realize at the time who Miss Quan was. It turns out she owns the East Shore Marketing Agency. Not like CEO. She actually owns ESMA outright, it's not a publicly traded company, and she and employs nearly 3,000 people, 2,000 of which are right here in the Philadelphia headquarters. I think if I had known what a powerful executive she was, I might have been awed, intimidated, shy, I don't know quite what. Anyway, she and I talked a while. Unlike the Anne Hathaway character, she was very friendly and personable. Like when I told her I was sick of talking about football, and don't even like football, she really brightened up, and went into a bit of a discussion about what's wrong with America, with football being at the top of the list. I can't say as I agree, really, but it was interesting talking with her. As we talked, it became clear I landed the job. She started telling me the details. Not quite like in the movie, I was not a business intern, but rather more of a butler. And, I'm not old (yet) like Robert DeNiro. I was 48 then. And Miss Quan, who wanted me to call her Cindy, was also 48. Whereas I am about as normal looking as a guy can be, white, slight belly, 5' 10," short brown hair, a bit of a beard, and blue eyes, she was about as Asian as one can be. She was also quite short and very thin, almost child-like, but you could see some age around her eyes, and in her manner. I was to live and work at her home, and come to work with her, but take time off as needed, not necessarily scheduled. In trade for my willingness to be available essentially around the clock, I was to have full access to her swimming pool, sauna, tennis court, unlimited Uber account, pretty much all the perks she herself enjoyed. In retrospect, I should have seen that it was all about loneliness for her. She is against the idea of marriage, and has had several relations with men, and a couple of women that all went south. Some of the people she has hooked up with have been gold diggers. Others were just two-faced, too religious, not religious enough, and so on, according to Cindy. So, she didn't want a relationship, but she wanted two things: Someone to take care of her domestic needs. She hates cooking, cleaning, and taking care of clothes. And a strong, friendly, yet proper male presence. I was starting to think this was just a bit too weird, until she mentioned the salary: $62,000 per year, and I didn't have to weld anything. So I took the job, and after a week, my duties became clear, and the working relationship smoothed out quite well. I laid out an outfit for her to jump into in the mornings, made breakfast, rode with her to work, took notes, made phone calls, delivered packages, all that sort of thing, and for the evenings, I made dinner reservations, or had pizza delivered, and then, because she particularly liked it (and so did I), we'd find something on Netflix and watch it together. The only thing is that she loved the romance comedies, whereas I'd prefer something with more action in it. She did like Jackie Chan movies, however. She went to bed in her room, and I went to bed in mine. About a month in, she called me from the bathroom. On the spur of the moment, she wanted to ask my advice about one of her employees. So I stood outside the door and spoke with her, but she couldn't hear me very well. She said, "Come in here." I said, "But, you're in the bathroom." "Dude, you're going to have to get used to that. You're doing so many important things for me, and sometimes I may not be properly dressed, I don't want that to cause problems, and especially not waste time." So I went in, and she was wearing a bathrobe and sitting on the toilet. I could see a bit of her breasts, and I could make out some of her crotch area, which appeared to be totally shaven. I started to feel an erection rising in my pants, but of course didn't say anything as I turned partially away to hide it. We talked for a moment, and then I left as soon as I could. A day later, she wanted me to come in the bathroom again to ask about dinner plans. To my absolute shock, she was not wearing a stitch! I loved her small perky breasts. And sure enough, her vagina was as bald as the day she was born. We talked casually for a moment, and then she did something that to call 'unexpected' would be a huge understatement. As if it were just something one always does in front of colleagues, or employees, or whatever I was, she started absent-mindedly rubbing and pinching her clit with her right hand. I pretended it was all in a day's work. In other words, I tried to remain focused, and talk about the guests who were coming to dinner, and the dinner plans. After her bit of self-fondling, she continued with her toiletries, walking naked into the bedroom, and putting on the clothes I had laid out. We breakfasted, and went to work, all in the normal way. Then, for a week, nothing. It was all business as usual. One evening, after the Netflix movie, she asked if I could come in her bedroom for a moment. It seems a wall switch wasn't working. As luck would have it, I remembered seeing another switch in her garage, so I was able to get it, and replace the switch right away. I turned off the circuit breaker, so I wouldn't get shocked, and it became fairly, but not totally dark in the room. Cindy was nude (no surprise anymore), and as I worked on the switch, she reclined on her bed, and started masturbating in earnest. I knew this was a show to somehow get me involved. But how do I ask, or what do I say? Finally, I said, lamely, "I'm going to turn the electricity back on. Do you still want to be doing that when I do?" She replied, "Yes, it wouldn't be right or efficient for me to hide anything from you. And, this business of dressing just to please my butler is inefficient." "First of all, I hope you think of me as more than your butler. Secondly, you never have to 'dress' for me. In fact, maybe I should undress for you." "Yes, please!" Ah, the magical words I had been hoping for. With that, I did turn the lights back on, pulled off my shoes, socks, jacket, tie, shirt, belt, pants, and so on. My erection sprang out, and I jumped on the bed next to her. For a few minutes, we stroked ourselves next to each other, but not touching. I was kind of sideways glancing at her, not knowing whether I should allow myself to stare or not. On the other hand, she was staring at my boner like she had never seen such a thing in her life. No words were exchanged. But it felt rather weird, and I couldn't stay hard. My dick softened up entirely after a minute, and I noticed she wasn't arching her back, or showing any signs of impending orgasm. I said something about 'being nervous.' She said, "This might help," and with that, she reached forward and ever so lightly tickled the underside of my penis with one finger. Man, was she right about that! My dick hardened up to it's full six inches in a split-second. I leaned back, and let my boss do whatever she was going to do next. She quickly stroked me to ejaculation, cleaned off her hand, and gave me a couple of tissues to clean myself. She then lay down on the bed in the most expectant pose I have ever seen. I had to laugh. "I know what you want, Cindy!" With that, I crawled up behind her so my chest and belly were pressed firmly against her back, reached around, and started stroking her clit. But that wasn't quite what she wanted after all. Now Cindy is one who asks for what she wants. She couldn't be the founder of such a large company if she wasn't. And she stated telling me exactly what she wanted. She wanted to get on all fours with her butt in the air, and have me finger her, both holes, with baby oil. Specifically that. So that's what we did. And I loved it. Her asshole was the prettiest thing I have ever seen, and I was sticking my index finger into it, and feeling the little contractions, as I reached around and rubbed her clit with my other hand. Eventually, the contractions became quite strong as she went into a good, solid orgasm, along with shaking, arching her back, and moaning loudly. I felt a good deal of wetness on my hand that was rubbing her clit. I don't know about you, but having someone's butthole contracting around your finger as they cum is about the most wonderful thing one can experience, other than having an orgasm yourself. As I'm sure you can imagine, this began our nightly - and sometimes morning - routine. It went on for a year. We never fucked. She admitted one time that she was deadly afraid of actual sex, because 'people get too close.' Well, that was alright by me. She being the boss, it was usually about me 'doing' her, but quite often she'd turn around and masturbate me expertly, too. She learned how much I enjoyed having a finger in her butt when she orgasmed, and it didn't take her long to start putting a finger in my butt as I came. Oddly, during the year we were together, I hadn't been dating, and didn't feel the need. One divorce and two children was enough for me, thank you very much! Cindy fulfilled my needs very nicely, even though it was a weird, lopsided relationship. Plus, I liked the $62,000 per year. But all good things must come to an end, I guess. Toward the end of our year, we started getting argumentative. As I think back on it, it was mostly me, trying to be too assertive. I was used to being the big-man-welder on job sites, ordering day laborers around. I was not used to taking orders from women. Funny, in our first months, it didn't feel like she was ordering me at all. And, Cindy is a very empethetic, soft-spoken person, so I don't know why I let the distaste wreck our relationship. But I did. We never argued very much really, but it was enough to put her off, and one evening she quietly suggested I go back into the welding business. You'd think that was a bad end, but it certainly was not! I learned so much about running a business from Cindy, that I set up my own butler business. Yes, specifically butlers. Most of my guys are good-looking (better than me, for sure), and most of my clients are women. I make it clear, without saying so specifically, that the butlers are supposed to perform any reasonable 'duty' expected of them, and I let the clients know that they can ask for 'personal services' beyond the usual. I also let everyone know that secrecy is very important, in order to maintain our impeccable business reputation. I have asked about what happens between my guys and clients, and most don't tell me, even though I own the company. That's exactly what they are supposed to do. What goes on between a butler and his client is indeed private. But some of those who have discussed it, tell me that yes, they have had various sexual encounters with the clients ranging from kissing to out and out fucking, but most, like the relationship I had with Cindy, are just masturbatory. It seems many women, just like us guys, love to have a little masturbation session every evening to help reduce the stress in their lives, and since they're paying for some hired help, it is nice that the hired help, can, well, help.