Well I'm the boss at our Family's Mortuary and I can say our husband doesn't know but a few of the male employees on our Cemetery grounds crew have had sex with me besides 85 year old old black Jimmy Joe that he knows I had sex with.

 

Not when he was my boss so idk if it counts lol. I ran into him at a club a few weeks after I moved on from the job, we had always gotten along so had a few drinks and a little catch up, I was 21 and he was 30ish. Things progressed from there and we ended up dancing, he pressed his hips against me and held me against him with his hand on my lower back and asked me if I wanted to go back to his place, and I said yes. We got a taxi back to his and had a few more drinks. I ended up on my knees in front him and sucked his dick before he fucked me and we dozed off. I left in the morning before he woke up, but he ended up calling me a few days after and we hooked up regularly for a year or two until I moved to a new city several hours away.

 

I was going to say no but now that I think about it, I surely did many times.

 

I own a construction company and have had sex with a few female customers which at the time they would be considered my boss.

 

Yes when I was 17 I worked part-time in a doctors surgery. I was helping one of the doctors with some filing before going home and it ended with me bent over the examination table as he came over my ass and back. We did it several times.

 

I have not slept with a boss. But, I am the boss and am fucking an employee currently. We have been friends for over 30 years, long before I hired her. We call her my work wife. Her and I have always had an inappropriate relationship in terms of how we talk to each other. That lead to touching, then finally one day she came upstairs to my office and dropped her shorts. She unzipped my shorts got me hard, and climbed on. In her previous relationships she has never really had good sex. She knows I am married, and my wife knows what is going on. Hell, it is nice to get it 2x a day sometimes in my mid 40s. But now she will sneak upstairs for a quicky once or twice a week and I usually go to her place before work after she gets her kid on the bus once every other week and give her a couple orgasms. She had never had one until This year. Now she has toys, and I am trying to get her more comfortable playing with herself.

 

Never have but some of these stories are really hot

 

We were at a meeting out of town and we hit the hotel bar for a few drinks and well I got a bit drunk and went back to my room got undressed put my nightgown on and got into bed after about an hour I felt someone next to me in bed and hands on me I was on my side he was pressed against me I felt him pull my nightgown up and him pull my ass cheeks apart his cock went right up my ass he reached around and grabbed my tits as he fucked my ass he thrust hard in my and shot his load in me he pressed up to me and said if I tell anyone at work about this he will have me fired he licked my ear and kissed my neck as his cock came out of my ass he said see you at breakfast and tomorrow night I will be taking your ass again he got up and left for his room

 

I'm white and my boss was black - a very attractive lady.
We'd flirt at work (years ago now) and she knew I'd always wanted to be with a black woman.
We'd talk in her office frequently (and sneak a quick makeout session).
So one night she told me to come by when I was off work.
We ended up banging for around two years.

 

I Fucked my boss on two separate occasions. I was going through a divorce and had taken the afternoon off to see my attorney and decided to go back to my office after it had closed to catch up on some work that needed finished before the next day. Upon arrival I found my boss still there and he wanted to know why i had taken the afternoon off for so I preceded to tell him why. After telling him he said he was just finishing some work in the conference room and wanted some input on it. He had the conference table loaded with papers which when entering he started gathering up and stacking them at one end of the table. I found that odd as he had told me he wanted me to look at them. He then proceeded to tell me how sorry was that I was getting a divorce and started to hug me and massage my shoulders . It was then I realized that he was trying to seduce me. What a better time when I am the most voluble . He then proceeded to put his hand up my skirt and touch my pussy. he then proceeded to take my panties down and insert his fingers in my pussy and started fingerfucking me. Now I was getting real excited as it had been quite a while since I had been fucked with going through a divorce and all. He then laid me on the conference table on the end where he had removed the papers opened my blouse and started sucking on my breast. I could tell by looking at the bulge in his pants that I was abought to get fucked. The next thing I know is he had dropped his pants and was standing there naked from the waist down with a big hard cock. He then shoved it in my pussy and proceeded to fuck me. After at least an hour of fucking with him cuming twice he then put his cock in my mouth and I started sucking. He was just starting to cum when all of a sudden the cleaning crew opened the main office door and we both scrambled to get dressed. I could tell they knew we were having sex by the look in their eyes but I did not know for sure until the next day which is another story of its own.

 

Well when I ran a dept i went out after work with the office cleaner we found a unoccupied part of a pub , got pissed I then had the urge to shove her mouth onto my dick so got it out grabbed her head and shoved it on, she had no idea and initially wasn’t playing being a Married mother anyway about 5 mins forcing her I came, then into a green space opposite the pub I pulled her jeans down and fucked her so hard she gushed all over the place jeans soaked we went back inside, she actually lent me £30 for the drinks but she was so happy I was debt free!!

 

Over 20 years ago I worked for a company run by two women. I was about 29/30. One of them, call her Anna, was a little older than me, blonde and long legs that she liked to show off; the other, Diana, was around my age now, a little heavy but big, round tits. We were in event promotion which regularly meant hotel rooms. I fucked them both a number of times during the two years I spent there. Never together, although I suggested it more than once. Good times. Though in the end it didn't stop them making me redundant.

 

Don't sh*t where you eat is a good rule of thumb for this, in my opinion

 

I agree with you but when I did it I was 17 and let's just say I wasn't quite or reserved.

 

Working apartments as ac tech i had many female bosses. Over the years we have had some office fun. Only once things turned bad from it.

 

I have been the boss.

thinskin

 

sort of. had a supervisor that was a hot milf. she was on my dick from day one.

 

When my wife was a stripper, parlor worker, escort, and more, she almost always fucked the boss and his associates.
It was expected.

 

My wife ran a business that we both owned. There were times I worked there as an employee on the payroll, not often but enough to know how she managed the place and her employees. So, yes, I slept with my boss every night and had sex with her every day. The 'management' went both ways.