Sex With Your Boss—How To Keep It Going
It just so happens that you have a leggy, buxom, pretty-faced boss; or one who is slim, with a great pair of lips and a perfectly shaped ass. The bottom line is: you want to fuck her—badly. She may be your team lead or a manager who is slightly senior to you. She may be single, sociable, and flirtatious. Perhaps she’s even given off signals that she would be open to your advances.
There is something exceptionally naughty about sharing intimate moments with a woman who has authority over you. That is probably part of the allure: the fact that underneath the veneer of managerial power and respectability she is, after all, a woman—with sexual needs and desires.
Indeed, it is important to keep both her gender and her professional position in mind if you decide to have an affair with your boss. If you’ve managed to get her in the sack, then you should take some time to consider how to keep it going.
Successful women are under tremendous pressure. The career advancements of your boss-cum-lover may have made it very difficult for her to keep a man. She may have recently split up with a boyfriend or is in a relationship she intends to put to an end. Whichever the case, don’t assume she’s either an incorrigible slut or a sex-starved lonely heart.
If the two of you never go to her place, that means she’s probably living with someone. If you do go to her place but never spend the night, it means she wants to keep it strictly physical. These are pretty standard indicators. But because your sex buddy is also your boss you may need to pick up on other signs. It may be the case that you do a great deal of travelling together and never see each other at the home office: that is, you only have sex when on the road. A woman in a relationship will receive all kinds of text messages and even phone calls late at night. You should be mindful of this when the two of you are making whoopee. She may even show signs of agitation if her significant other is blowing up her phone while you’re inside of her.
This is all by way of saying that you should try to keep things simple after that first encounter. Enjoy the ride and allow her to open up about what her relationship status and her relationship needs in her own time. If you are loving the sex, and all that it includes—the frisky messages, perhaps even a few risqué gropes in the office—don’t mess it up by asking intrusive questions or making presumptuous suggestions. The more comfortable your boss feels with the sex the further she will be willing to go. I have yet to meet a man who hasn’t had an office sex fantasy. If you continue to bang your boss the way she likes and refrain from introducing unwanted complications, you might just find yourself in a late night meeting that ends with a blowjob or a table topper.
Your conduct during office hours is a vital element in keeping the flame burning. Most women agonize over their sexual reputation. Women in positions of power must be exceptionally vigilant in guarding it. Your boss has to work not only with you and your fellow subordinates but also with peers and superiors of her own. She risks being seen as sexually desperate or slutty if word gets around that she’s sleeping with someone under her, and this can make it hard for her to be taken seriously. It’s unfair; it is in fact a shitty deal for women, but that is how things tend to work in corporate America. That is why she may insist on absolute discretion on your part. You must be willing to put on the façade of work colleagues when you are in the office and there are people around. If she discovers that you can’t keep your mouth shut, then she will cut you off.
Finally, you will have to consider the impact that having an affair with your boss can have on your career. If it turns out that she does want something more serious and you’re open to it as well, then the two of you will have to negotiate a way of making that work within the confines of company policy and politics. If she wants something more serious and you don’t, then you will need to be honest but gentle in giving her that news.
Sex with your boss can be fun, exhilarating, and irrepressibly gratifying—if you know how to avoid the pitfalls.
About Christopher Reid Chris was born in Washington, D.C. and lives in Britain. He works as a blogger, essayist, and novelist. His first book, Tea with Maureen, has just been published.