Thinking About My Boss

I started a new job at a very small company in late spring this year. I took the job, which pays much less than the 80-hour workweek, high-stress positions I am used to, because I wanted shorter hours while I start my own company on the side. My superviser Cal, who started a few months before I did, took the job because he wanted more time to spend with his young family. When I started work I resolved to keep my emotional distance from my coworkers. I was afraid of becoming too submerged in the company culture and daily concerns of the job, losing sight of my real goal of simply keeping the lights on while I built my own business. Within two weeks, I started noticing how attracted I was to my boss, but I made a huge effort to quash those thoughts and to keep our conversations to a minimum. After all, everyone deserves to be able to go to work without having sexual desire directed at them. About two months in, a coworker was fired, reducing my department to just my boss, me, and his other direct report--a remote employee who came into the office about once a month. As my job progressed and Cal and I were the only two working together daily in our relatively self-contained department, I began to let my guard down, and we started talking more and more. Every once in a while he would remark on a similarity between me and his wife--"Tammy says the same thing," or "Tammy likes that too," or "Tammy is that way too." Cal is a very sweet guy, kind and generous, and I figured that in a way, his comments were a subconscious compliment: establishing that I am a person who shares many qualities with the woman he's chosen to spend his life with. Eventually it became a joke between us, that if he were unsure what I would prefer, he could assume I shared his wife's tastes. Once on a particulary busy workday we ordered a pizza into the office. I don't make a habit of ordering pizza and didn't know any of the restaurants offering it in the area. He chose the one his wife liked, and to his amusement, I liked the pizza far more than I usually do. Two developments in the middle of the summer set me irrevocably on the course of wanting to sleep with Cal. The first was that despite his professional manner, Cal found it difficult to hide that he was frustrated with the haphazard, backwater nature of the small company and the incompetence of the leadership. Though I frequently shared his frustrations, my mind was constantly on the business I was building nights and weekends, and I found the situation less demoralizing. I began to suspect that Cal thought of the situation as the two of us together against the world, and that excited me. The second development came in late summer. The conversation started innocently, and though it also ended innocently, my thoughts about Cal by the end of it were anything but benign. I had seen an attractive man with a grill while riding the lightrail to work, and I mentioned to Cal that I'd never found grills attractive, but in this case it was. Cal immediately went off on how much he liked grills, and we quickly made the natural step into other body modifications. I should pause and say that I found this grill comment from Cal to be very, very funny and not a little surprising. Cal is a white guy with three blonde, pretty children and a house in the suburbs. He's 48, 6'1" with light brown hair, an attractive face made more handsome by his joking, smiling manner, and the hottest fucking muscled arms I have ever had the opportunity to gaze at while ostensibly talking about what to do about our clients. Aside from a large tattoo on his forearm, Cal gives the impression of being rather standard in terms of what he might want physically. Though I often fantasized about what he could do with those arms--picking me up and tossing me on the bed, holding me against the wall while kissing me--I had little to no fuel for my growing desire. Then, after his grill comment, I asked if he wanted more tattoos. Thinking the answer was probably no, I was surprised when he said that he did, and proceeded to describe a large one he already had on his shoulder, followed by our first real conversation about his pre-family life. Before his photogenic childeren and white collar career, he was a musician with a muscle car and (he told me later) an insatiable quest for sex. I've always had a thing for older men. I'm bisexual, and while I tend to date women my own age or younger, the men I'm most attracted to are much older. Already, Cal was in the perfect age range for me. I'm 31, but I prefer men in their late forties--more mellow, more experienced, and unafraid of what they like. I also found his height extremely appealing. I'm 5'5" and 112 pounds, with tiny wrists and small, but perfectly round and perky breasts. I couldn't get the idea of his larger, muscled body on top of my own much smaller one out of my head. Add to that the chemistry we were already discovering and my newfound recognition that he had a lot of bad-boy tendencies around the edges of his character--I was sold. I didn't want to take even a chance on jeopardizing Cal's marriage at all, and he is clearly very much in love with his wife. He adores her and considers himself beyond lucky to have found her. Fortunately, I found the idea of her very exciting as well, and I have a history with "straight" women--though they weren't straight the morning after:). A plan--more of a fantasy, really, since it seemed unlikely--began to form in my mind. What is the only ethical way to sleep with a married man? To sleep with his wife too, together, as a couple. The idea of his wife and me finding ourselves compatible in the bedroom, or even Cal entering me while I was kissing his wife, was too much for me, and I was late to work twice from vividly imaginging it, with my fingers inside me. I figured I would try to get to know her and keep my eyes open for any opportunities. I started inviting Cal and his wife to dinners and concerts and whatever else I could think of. At the same time, Cal and I started going out to lunch on Fridays and also began texting more. Our conversations while away from the office became more personal, and eventually he even asked me questions about the relationships I'd had with men his age. Once while driving back to the office from lunch, preceeded of course with a disclaimer about how satisfied he was with his marriage, he mentioned that he neverthless had eyes and was a very visual person. Well, of course most men are extremely visual in terms of sexual stimuli, but after that comment I redoubled my efforts with my appearance. I wore a cute plaid miniskirt more often, with black stockings and low heels that enlongated my already toned legs when I leaned over his chair to show him something on his computer--an action I found more and more necessary for our work. I wore lower necklines more often, and wore tight tops that accentuated my perky breasts when I stretched at the end of a long day. My main avenue of attack, however, was the little touches that can be passed off as friendly and innocent but really serve to focus someone's attention on the physical interaction. I would touch his arm distractedly when trying to make a point. For the briefest moment I rubbed his shoulder when he was frustrated with a client. I fixed a piece of his hair that was sticking up. This is the area to which Cal responded the most. He began doing the same to me--friendly little touches to my arm, a poke to my knee while I was sitting on his desk--but especially when I would lean over his desk and type something on his keyboard, he wouldn't make an effort to move away from our proximity. I became bolder, resting my wrist on his arm as I typed, sitting close to him. The change has been extremely slow, even glacial, but he has become more flirtatious. I'm not sure yet if he even thinks of me as attractive, and certainly I remain committed to the idea of only acting within the bounds of his marriage; I continue to take every opportunity I can to invite Tammy into our dynamic. I plan to leave the company soon to pursue my own business full time, and Cal is actively interviewing for other jobs. Our mutual exit strategies only serve to excite my fantasies further. After he is no longer my boss, will he feel more comfortable escalating our personal interactions? My favorite fantasies involve Cal's hands. He has huge, strong hands, and I spend every Saturday morning climaxing hard, lying on the floor with my hands underneath me, my breasts rubbing against the rough carpet, thinking about those big hands on my breasts. I rub my soft breasts while imagining his hands there, until my nipples are hard, and then I imagine his fingers around them. I imagine him holding my arms above my head, pinning both my wrists with one of his hands, and kissing me, pressing his hard cock against my body. I imagine rubbing his shoulers at the end of a long day and that semi-innocent action turning into sitting on his lap, my breasts against his chest and my hand on the back of his head, my tongue in his mouth. I want him to feel my tongue and want it, and then let me take his cock in my mouth. I want him over me, not just as my boss, but on top of me. I want to encourage his bad boy inclinations. I want to be under him, my legs spread wide open, and present myself to him, and for him to take me.