New boss reaches into my skirt, then into my pants, then into me, while my fiance encourages me to let him.
This story is largely about a committed couple who lived for several years in separate cities, required by their jobs. Both partners gave the other room to have sexual experiences, short-term affairs so that they did not have to be completely celibate for their years apart. Their affairs were not "cheating" or "unfaithful" in any sense. They encouraged each other to enjoy themselves sexually, just so long as they did not become entangled emotionally. They talked a lot about their adventures, used them as fuel for their mutual lust. Sport fucking, yes; romance, no. This story is about the woman's adventures in her workplace.
If you are upset by the idea of spouses having sexual experiments outside their primary relationship, please stop reading right now. Don't just leave nasty comments because you don't like this type of story. Skip it entirely. You have been asked politely.
There is a lot of truth here, plus some fictional details added for spice. The overall arc of the story is completely true. Some incidents, some actions, some dialog have been elaborated, increased in intensity and detail. Ms. Screwloose isn't a slut just because she went to bed with a number of men. She was still single, and her fiance encouraged her to play. If anything, he was her coach cheering from the sidelines. She was basically serially monogamous in her affairs. Sex-driven, not sex-crazed. A helluva woman.
For some years between grad school and marriage, my guy and I carried on a long distance relationship, me in New York, him in DC. We got together on weekends as often as we could afford, bless Amtrak. Train was cheaper than the shuttle (plane) but still too expensive to do all the time. Otherwise we just had long phone calls and the occasional letter. We were young and in love and highly sexual, so there was hot stuff in the phone calls and the letters.
I was assistant to the president of a medium size marketing firm. I had an MBA and several years' experience, so I was not just a glorified secretary. I was his top staff guy - well, girl of course, but that's what he told people: "See my staff guy." At that time, I had been working there about four months.
This was a very proper, buttoned down office: suits on the men, dresses or suits on the women. Skirts were well above the knee as was the fashion then. But no pantsuits. Verboten. It's not that there was no hanky panky in the office, it wasn't *that* buttoned down. I saw hints of it in some of the working relationships, everyone saw a little of it, but it wasn't blatant. So, a normal office, somewhere in the middle between a convent and an orgy.
He was really a nice guy, my boss. Fiftyish, tall, thin, salt and pepper, really good looking. Personable, forceful. Smart as a whip. Top in his field. And I really liked him. He was, of course, married out in Connecticut somewhere.
One day, I was showing him new figures for an ad campaign, standing next to his chair on his side of the desk, leaning down to reach the papers. Our meetings were like that, he seated at his desk, with me standing next to him, usually leaning down to point out important notes or numbers on the papers. This day, as I was leaning down, he put his hand around my waist gently to pull me closer. Okay, not that big a deal. I didn't object. It distracted me for a moment, but not a problem, and it went no further that day.
The next day, same situation, he pulled me closer. And then, after a minute, his hand slid down onto my hip. And then after another minute, down to my ass. Now *that* was distracting, and I lost my place for a moment, but it didn't interrupt the conversation much.
I was a little surprised. There had not been a lot of sexual tension between us. I thought he was a very attractive older man, probably the BMOC in his college days. He was gorgeous and a jock in his youth, and was still very handsome years later. I had, and still have, a thing for rugged guys with a little gray at the temples, so he fit my type.
I didn't know what he thought of me as a woman, at least not until that moment. He had touched me a few times, an encouraging pat on the arm, Good Job, that sort of thing. This touch was not a friendly touch or encouragement, nor just a pat on the butt. He left his hand there, stroked up and down my ass from waist to leg, and caressed me. These were the days of near-universal pantyhose on businesswomen, so all he felt was a firm butt through my skirt. I wasn't appalled, I didn't scream or slap away his hand. This was decades before the days of sexual harassment lawsuits. Boys will be boys, y'know. The meeting ended, I stood up and left his office, tingling a little from the overly-familiar touch.
Wow, I didn't know what to think. An affair with the boss was a cliche and not a good one. Risky. It might aid promotion possibilities, but who wants to be the girl who "slept her way to the top?" And if it goes wrong, it's always the girl underling who gets fired or transferred to Siberia. But he was a very sexy guy, powerful, magnetic. And I was between playmates. I had to be careful.
I talked to my honey about it in a very offhand way. I didn't think it was a big deal, though it was certainly more than a hand casually around the waist.
"Is he really off base here? I mean, is 'dipping your pen in the company ink' expected or frowned upon or forbidden? If someone found out about it, who would be in trouble, you or him?"
"Oh, I think I would, There are some hints of office relationships, but nothing really public. And he is The Big Cheese, so no one would challenge him on it, even if there were a policy about it, which there isn't."
"Okay, what do you want to do about it? What are you concerned about?"
"Well . . . I don't object in general to a little fondling. But what if he wants to go further with it? What if he wants to feel me up? Do I let him play with my boobs? Kiss me?"
"Don't ask *me*! What do *you* think? Are you concerned about being a toy or about your career?"
"Career more. I guess I don't mind being exploited a little bit to keep this terrific job."
"Then do whatever you feel comfortable with. You know that, sweetie. Play as you wish. Have fun. Just tell me about it. And don't get too involved."
Given that reassurance, I didn't withdraw, I didn't object, so this became standard, this touching, every meeting we had where I was standing by his desk. He liked my ass, and I learned not to mind. There was no worry about getting caught. It was an old office in an old, stone, financial building, with heavy furniture and solid doors, heavy bookshelves, soundproofing. No one could see or hear anything from outside.
Then one day, during our usual meeting, his hand strayed lower, down my leg. Much lower, down past the skirt to my stockinged leg. And caressed there. Now this was different, much more familiar. Conversation stopped. When his hand came back up, it caught the hem and went on up under my skirt. Not far, but clearly under. Headed up my thigh. On the *out*side of my thigh, yes, but inside clothes. Yikes, this was getting very familiar. I know what it means when a guy reaches under my skirt. Was I to be a plaything as well as a business partner? I waited to see.
I didn't want this to happen, well I didn't *think* I wanted it to happen, and I was not encouraging him. I just wasn't pulling away. Maybe it would stop here. Maybe being felt up a little by the boss was part of the job. My guy always told me what a slinky bitch I was; maybe the boss just couldn't resist my charms. Ha ha. Right.
The next day, his hand was back on my ass, then my leg. Then the leg nearer him, so it was not on the outside of my thigh anymore, but on the inside. Whoa. And he exerted a little pressure to pull that leg toward him. God, he wanted me to open my legs! This wasn't just an almost-innocent touch anymore. My legs were not tight together, just standing there, but they were not that wide apart, either. Oh, six inches, maybe a foot. He pulled again. I complied. I moved my knee toward him another foot. He felt higher on my leg, well up my thigh, I could feel the skirt being lifted by his wrist. Omigod he was within a hand's breadth if the top of my leg. Another few inches and he would be touching my crotch! I had spread my legs to give him room to get to my sex! Sure, I had the pantyhose and panties between his flesh and mine, but still, my boss was feeling me up, on the way up to my pussy.
