Did you ever have sex with your boss?
How did it happen?
What was it like?

 

I'm my boss. Jerking off counts?

 

Yes I did, She was my commanding officer in the Army, I was the Company Operations Sgt, over the 18 month of her command tour we had sexual relations as often as the time and place allowed, on an average about every other month or so, it was great

 

Yep! #1 (male): In my teens, I was hanging out at my boss' house watching football and drinking and he came onto me, led me into his bedroom, stripped me, sucked me off, then fucked me.
#2 (female): Had just closed-up the warehouse and found my boss at her desk crying. She wouldn't tell me why, so I stood her up and innocently hugged & consoled her. Next thing I know, she's kissing me and leading me to a back room. We stripped off our clothes, I laid her down on an empty desk and ate her pussy. Then, stood up and fucked her brains out!

 

Omg yessss!! My first time was my boss brought me home after work. We talked outside then came inside just talking. Then some time inbetween talk he pull his dick out his zipper by saying just sit on it and get off. I finally got on him backwards and sat still we decided to not move just sit it in me. After a few seconds I grind on him and he started. It was good to him he pushed me off so fast cause he nutted on his pants. So after that experience we started fucking, and 69ing each other often after work. So after started staying g at his place every night, key was given to me, we slipped up he me couldn't pull out and nutted in me and got me pregnant. I miss him. My current boss been in me too

 

Yup I have before it’s very exciting

 

Yes.

We were in the right place at the right time.

Not much different. I mean, other than it being the boss, the logistics don't really change.

 

Yes I ended up working for a man I had already had a sexual relationship with. We fucked in his office from time to time. But it was over by that time for us.

 

Nope. I never got lucky enough to have a boss I wanted to fuck.

 

I fucked 1 boss’s sister in law. And 1 boss that was a cuckold couple

 

When my wife stripped at Lorraine's Bar in Lafayette, IN, it was a regular duty to fuck the owner
and/or a personal friend of his... That usually happened at least once per week.

If the bar was not busy?
It happened every night that she worked. And all that was before she began true prostitution.

*Back then? It was ALWAYS bareback.

 

She did that while she was married to you? or after? Not judging, just curious.

 

It was a carry over from the Hippy Dippy era. Several years prior, she already had the go ahead to fuck anyone, anywhere, anytime. It was just a "sexual trip".

She loved sex and was as insatiable as Marilyn Chambers, in the movie "Insatiable". Knew that since I met her in high school. She had a 9 inch super thick cock
working on her since years before having a driver's license. So, she expected that minimum. Later, when she took the above type jobs, she did not consider it
a shock to have to fuck. She probably wanted it more than the guys. She had quite a sexual appetite.

Remember, this was a series of university towns, in a time with rare STDs, No HIV yet, No Hepatitis. ETC.
Unless there was intense screening, I do not see how it could be done now.

 

Thank you. I also read more about it in the comments of your profile. Interesing. And I agree. Different times. I was born in 69 so i can only imagine. But your answers lead to more questions. Who was the 9" thunder cock before her aquisition of a drivers liscense?

 

Never the boss, but the bosses administrative assistant. That was hot!

 

yes I have had sex with her.... the first time it was sort of part of the interview

 

Can’t say that I have. Additionally, to my knowledge, it’s never been an option on the table.

 

I have

 

No, i wish I would have had an opportunity like that, but it never happened.