After a recent fling with the bosses son…I’m curious as to how many Dopers are involved in naughty/forbidden/work etc. flings/romances etc.
Anything in that category will do 
In college I was an RA and I had an encounter of a sexual nature with the Director of Residence Life. I was totally in love with him, but he was married. I couldn’t keep it a secret and he had to fire me as an RA.
When I was about 30 my new boss, a 55 year old man, got a crush on me and we had a very fun affair for over a year. He was VERY naughty! Very naughty indeed. It only ended when I met the very appropriate man I am currently married to.
I have an unholy attraction to our fax machine.
Fortunately, the stapler is able to satisfy my carnal desires, so I can resist the siren song of the fax.
Long long ago I was working in a cd store. The owner’s married daughter would come in to work a couple days a week. She put a lot of effort into flirting with me and telling me how unhappy her marriage was. One night it was just she and I closing the store. She was pouring it on pretty strong, so I just grabbed her and kissed her and we wound up having sex in the back office – on her dad’s desk.
My boss’s son is HOT and I’m very attracted to him, but he’s also worked here as an intern so I’ve been good so far. That and, well, he might be out of my league. Or he might think I’m too old (He’s 19 and I’m 26). Dunno… but I certainly wouldn’t complain if anything were to happen!
*Naughty naughty!
Loud and bawdy.
T-t-t-t-tease me.
Take it easy!
Hug and squeeze me
'Cause I’m a naughty naughty boy.*
It can get right boring for just graduated high schoolers working part time at Montgomery Wards shoe dept on a Summer evening, so Stacy and I were very pleased to find that the large stockroom had plenty of nice places for hot, sweaty teen aged sex. We got caught once by another employee and the shit hit the fan. We didn’t really care, tho. Plus, the fear of getting caught again made it even more fun!
I was sleeping with the boss’s daughter at a roofing company I was at, but the boss knew it. In fact, being his kid’s BF is why he asked me to work for him in the first place.
For the past more than a decade, I haven’t seen anyone at work to sex up, as I am self employed. Insert your own joke here.
Grrrreat. Thanks, NoClueBoy.
Baby this could be the first time, this could be the first time…
The widowed owner of the company I worked for years ago.
Once I turned in my two-week notice, the fling began.
Once I actually left her company, it abruptly stopped.
The reason I gave notice was to take a job far away. As I was leaving behind a divorce and starting a ‘new life’ myself. We kind of gravitated toward one another for some fun before we went on with our lives.
Sort of. Nothing’s happened yet and it might not but they’ve definitely made their interest and intent known.
The planning has been fun.
Well my story goes something like this. Started work in October. Met the bosses son on the first day. I went :eek: gorgeous. We’re the same age, but I still thought he was out of my league having money, excelent education, and a gorgeous ex. Anyway, one day he in late october, he was in an odd mood and I took it upon myself (we were sort of friends by now) to get his mobile number out of the database and send him a quick message of good thoughts. Within an hour it was becoming somewhat more than friendly. This continued for a couple of weeks. It was coming up to the work Christmas party and it was to be held at his house. But we ended up having an argument about 8 hours before the party started.
So as the night wore on, I was still pretty annoyed and figured I’d sleep it off.
Then I remembered that my watch was in his room. Dammit. Being 3am and all. I figured I could sneak in. But alas he was awake. I was polite, he was polite. We started talking our argument over. One thing led to another.
We have only in the last month been happy as friends and stopped with the pety fights. Though I havent worked there since January. And with good reason. At least is parents didnt find out. Or mine for that matter.
I am WAY too young for this shit!
When I was in college I had a steady boyfriend, and came home for the summer but still took courses. Well, in my Anatomy class I met a very sexy young man. One thing lead to another and we ended up meeting several times before the summer was over. He was the best time I’ve ever had.
Current? Do you really think I’d 'fess up? Not on your life.
Currently I am kinda sleeping with someone here at work. He works in the other department and technically I am supposed to be managment. No-one knows and we are trying to keep it that way. It is fun 
THEY?!?!?
You’ve gotta dish now. Seriously.
I’m guessing gender-neutral they, not plural they.
Of course, I’ve used it in the latter case before, and Aes is a lovely guy, so anything is possible.
I have this terrible tendency to fall for girls who are already taken, which leads to me being a bad person sometimes. Last year, for a while, I was sleeping with a girl I knew who played ultimate with me on the uni team which is all good. Except for the fact that she had a boyfriend who she’d been together with for ages… and he also played ultimate on the same team so I knew him and was at least reasonable friends with. I try to ‘justify’ this with the fact that she was amazing in bed… surely that’s an acceptable excuse? Or not.
Then last semester I managed to hook up with a fairly religious christian girl who also had a boyfriend. She was away half way across the world for a semester abroad though. She would go on about how she was going to marry her bf blah blah blah… Very strange kissing someone when there are pictures of their boyfriend on the wall.
Then there is the most recent instance of me being a bad person by just last week hooking up with a girl who I like who also plays ultimate and has a boyfriend on the team. Pretty similar situation to my previous one. It leads to some tension though because her boyfriend knows that I like her (I’m not to good at being subtle about who I like) and probably suspects something. He’s also a very jealous person and she’s pretty outgoing. So they fight a lot and have a very weird relationship. Nobody knows that we’ve hooked up though, and obviously I can’t tell anyone about it - no reason to make the situation really bad. It’s difficult being out partying with the team or whatever when she’s around though because we both want to hook up with each other, but are definately not allowed to.
Not that this justifies my behavior at all, but my view is that it is the person who is in a relationship’s resposibility to not cheat on their bf/gf. I have no obligations towards anyone. I’m sure others disagree, but sometimes it’s just too much fun being naughty. Besides, I’m still in college - that’s when you’re allowed to be a bad person for a few years, right?
As punha guessed, I was using a gender-neutral term to be as vague as possible although I have met someone local but that doesn’t seem to be going anywhere and doesn’t fit the parameters of the OP anyway.
I’ll ‘fess up.
I had an affair with my boss’s cousin/best friend (“Affair Guy”), which we had to hide because the boss would have fired me on the spot. Boss and I had become good friends, to the point where I was almost part of his family, and many people (such as Boss’s mom) thought we were dating. Problem was, Affair Guy already had a girlfriend. Boss used to tell me that this girlfriend was the only one that AG had never cheated on, so he was really settled down now. He also used to tell me it was a shame I hadn’t met AG before he got this girlfriend, because we were so much alike. I have no idea how he didn’t know what was going on, but Boss was so straitlaced that I doubt he had any concept of deception.
So after I left that job, I got another… at Affair Guy’s company. (No, I wasn’t stalking him. I just wanted to work for that company, and they offered me a good position.) He was a little startled to see me sitting there in my new office, but the affair rekindled that very day, and continued for another two years. We ended up sharing an office, often messing around in the supply room or even at my desk, and nobody ever noticed. I had other boyfriends, and he eventually married his girlfriend, but we always gravitated back toward each other. (We did not, however, have sex after he was married or whenever I had a boyfriend. I do draw the line somewhere.)
The whole thing went on for almost three years. Only two other people (my best friend and my mother) ever knew about it. I’m still amazed that nobody else figured it out.
A couple of years ago, I was visiting my mom in that town, and we ran into my old boss at a diner. We chatted for a few minutes, and he told me that his cousin still asks about me, and how I’m doing. My poor mother almost choked trying not to laugh, knowing that my former boss had absolutely no idea.
Yeah, not one of my finer stages in life. Still, lots of good memories, and some lessons learned.