My story is different, as I was first totally opposed and then totally in favor. Here is the true story about my first wife's first office affair.
When she was 21 (and I was 27), she had dropped out of college (she could no longer afford it) and gotten a job as a bookkeeper. We met, fell in love, moved in together, and I convinced her to quit her job and resume her education on my dime, so she quit her job. About one year later, she told me that she had some good/bad news: her ex-boss had asked to work four hours in the morning on Saturday for $50 an hour, which would be paid under the table, without the IRS’s knowledge or anyone’s else’s knowledge, a point which he stressed as being the key point. Moreover, if they finished early, she could leave and she would still get paid for the full four hours; if they went over time, he would pay her $75 an hour. This was insanely big wages for the time, the late 1980s.
I heard mostly good news, as we were spending far too much money, more than my income alone could support. In addition, I had bought her a new car and we ate out at least two or three times a week. In short, we were using up my savings to make up the difference, at a rate of close to $1000 a month. Her bringing in $200 every Saturday would almost fill in the money pit. She was, however, greatly troubled by his offer. Why on Saturday morning? Why so much money? Why under the table? Why would she be the only employee there with him? She told me that he probably expected sex from her as nothing else made any sense. Somewhere the same thought must have hidden in my mind, but I was so dazzled by the extra income that I ignored it. Her blatantly stating that he might want sex from her meant that I had to face the possibility.
After half an hour of questioning her, I discovered that her boss was both the best and the worst boss possible. He underpaid his workers, who were mostly females, both young and old, yet gave huge, monstrous bonuses at Christmas each year. He also gave generously to charities and to employees in need. An older female employee fell dreadfully ill; her $30,000 worth of health insurance covered only little more than half of her medical bill, so he paid the difference and bought her a $10,000 electric wheelchair. (My ex overheard the senior accountant ask what the cash cutoff on paying the hospital bills was and her boss told him as long as there was money in the back account, pay the bills.)
He was in his late thirties and handsome; he was also quite short, maybe five-eight tops. His wife was an unalloyed bitch, so much so that no one could be so saintly or masochistic to live with her, yet he did. He lived in a sexless marriage, yet had three young daughters. He had many affairs with the women he employed, including an exotically beautiful girl (half Asian) who was my wife’s close friend. He had almost had an affair with my wife, but she broke off with him—in a fairly gruff way—before it could be consummated, when she discovered that he was fucking her beautiful friend; yet he gave her a glowing recommendation letter and a big exit bonus when she quit. It was confusing. I had never met him. When I cursed him, my ex would support him; when I praised him, she damned him.
Finally, I asked her if she would take the job, if there were no chance that he would try to have sex with her. She said she would gladly accept the job offer. I told her that she called the shots here, not him. All she had to do was say no, firmly and resolutely. If he did persist in pestering her, she could just walk out the door. If he followed her out the door…well it was best not to think about what I would do to him then. Okay, here is the insanely ironic part, we had been indulging in MMF threesomes and we were constantly on the outlook for new men to open her legs to and he seemed an excellent candidate in so many ways. But I had adopted her disdain for her ex-boss, so such a possibility was unthinkable—well, at least at the time unthinkable. She accepted his job offer and left the next Saturday morning. (I didn't leave the house, in case she called in distress.)
Well, we soon had all her troubling questions answered. He hired her because he was desperate. He had hired a relative of his wife who had just graduated from college and the kid seemed to be a genius, easily doing the work of two or three workers. Two months after hiring the wiz kid, however, her ex-boss discovered that the kid was an idiot and a fraud. Her boss looked deeply into the financial mess the kid created and he feared either losing his business or doing jail time or both. That’s why he hired my wife: he had to find all that was wrong and set it straight; she already knew how his business was organized and she was a fine bookkeeper—and she would not tell any of the other employees or the police what had happened to the books.
She had showed up the first morning wearing jeans, oversized sweatshirt, and running shoes, not the attractive skirts and blouses and heels she had worn a year earlier. He had been there already for several hours and he barely looked at her the entire time, as he was in panic mode and they had get to work. She loved the job, as it was short, but intense, more like detective work than accounting, with no meetings and no phone calls. Imagine that you are given a huge tangled ball of thread and you must carefully unravel it.
That night, we joked about how wrong our worries had been and how different her workday was from the possible Penthouse fantasy. That is then that I began to rethink the situation. Soon, the unthinkable was all I thought about. I was telling her elaborate fantasies, wherein she and he fucked on the conference table, and wherein she worked naked with him, his eyes glued to her body as her breast bounced and swayed as she walked about the room. She loved it; I loved it. When she came home from work, I asked her recount all the sexual details and she made up wonderfully salacious scenarios for me.
After the third Saturday, we realized that her job would end soon and we decided that she should try to seduce her boss. Thus, she resumed wearing sexy clothing and she made a point to bend over in front of him whenever possible, so her blouse could fall open enough to reveal cleavage. And she pressed against him, as she and he looked over reports. She wore nylons and heels, but quickly removed her shoes, which her exotic friend had told her turned him on (I assumed that his liking being taller than his women was a more likely explanation than any foot fetish he might have). She did all she could to entice him, without ever obviously crossing the line; in vain. He never made a move on her.
Of course, he had other things on his mind. But by the fourth Saturday, most of the most egregious errors and frauds had been uncovered and her boss was less worried. It was either the fifth or sixth Saturday that they had finished up in just two and a half hours and he gave her four $50 bills. She took the money but didn’t leave. Instead, she remained and talked to him about all the past flirting and the sex they almost had and she asked why he hadn’t come on to her again. He apologized for the time before and told her that he respected her too much to do anything like that now. She told him that she was sorry to hear that, as she would now welcome his advances. They talked away and, after half an hour of talking and her moving closer to him, the truth was revealed: he had seen her with me and I scared him cold (I am 6’ 3” and I weighed about 210lbs then, in fine shape). She informed him that he had nothing to fear, that in fact I wanted him to see her naked, taste her skin, smell her pussy, and feel her wet insides with his cock.
He didn’t believe her, so she called me at home and had me talk to him. An amazing conversation. I had to convince him to fuck her. About an hour and half later, she walked through the door wearing no pantyhose and a big grin. I had her lie down on our bed and I remove her panties. Her pussy looked used, her pubic hairs wet and dangled, her labia swollen. I had to lick her just-fucked pussy, which she resisted, at first, but then relented. I ate her recently fucked pussy, while she told me every detail. After her first big orgasm, I fucked her, her pussy feeling super wet and looser, in spite of which I came super quickly. Then at night, she recounted her sex-filled morning with him again for my hungry ears. Our sex life became supercharged. Sadly, this only happened again for about five or six Saturdays. While it lasted, it was fantastic.
After the their first encounter, she and I decided that he was only to pay her for the actual hours worked, not for any of the time they frolicked naked, but he refused to pay her less. By the way, she did end up working in the nude with him, which was her favorite fantasy, but only after the first two hours of real work. Then she took off her clothes and worked away for an hour; then they had sex for the last hour. He made an interesting request of her: she was to slowly remove her clothing, one article every ten minutes and she was not to sex it up for him; instead, he wanted to act naturally and when he could no longer hold out, he would come to her and devour her naked body.
Still, I preferred to imagine that they spent the entire time fucking and sucking. In fact, I loved hearing about their sex rather than watching them do it before my eyes. As they say, our most important sexual organ is our brain, as sex actually happens between your ears. In terms of stimulating nerves, nothing can beat a strong vibrator or, as some men are into, direct electrical stimulation of their cocks with AC current. Yet, the orgasms produced by such means are small compared to what can be delivered by woman (or man) that we desire completely. I seemed to have said a lot, but so much hasn’t been said about their work affair. For example, the first Saturday she worked, I got about five phone calls from to keep me updated on what he was up to. Later once they began doing it, she would call me while he entered her.
I remembered one call while they were fucking like mad. In my mind, I pictured her lying on his desk, as he held her legs open and fucked her savagely. The problem was the sound effects were all wrong, as I heard loud rolling squeaky noises. I had her tell me exactly how he was fucking her and she said that she was sitting in computer chair, with her legs open and draped on the armrests, while he held the chair and pulled her vagina on and off his cock. By the way, he did ejaculate in her mouth, but never her vagina (other than their first time), as he always wore a condom. Another by the way, I purposely did not fuck her on Friday (and sometimes Thursday as well). Not because I was into any cuckold sex-withholding scheme, rather my cock was much bigger than his and we wanted her to be extra tight for him. She only orgasmed when he ate her, never from fucking. And here is the last interestingly oddity, a year later, he and I became good friends.
We were disappointed, when he told her in a phone call that his wife had visited the office just 15 minutes after she had left last Saturday, so he couldn’t risk having her work for him anymore. Part of me was happy that their office sex affair had ended, as my conscience was feeling regretful about the money she was getting for fucking, not working; but my cock was quite unhappy, as it had really enjoyed those Saturday afternoons she had spent with his cock in her. Regular sex is the best sex.