So I have a really hot, cute female boss. She's probably several years older, hard to tell her age as she looks young. Not sure if she's attached, never seen a wedding ring. And I have no idea if she finds me attractive at all. I fantasize about fucking her, exploring her body and making her cum over and over again. But it's against the rules for superiors and inferiors to date or do anything sexual (if caught) I need this job too much to jeopardize it so I haven't pursued this at all. I don't know how. How would I go about this, if it's even possible? I don't want her to lose her job, I don't want to lose my job, but there's the thrill and risk that turns me on, and when she's so hot it's even hotter.

Are there ways to drop hints? I mean if she's attached and happy, and there's no interest on her end then my problem is solved, I won't do anything. There's no point in wasting time on a lost cause. But if she finds me attractive and could be interested despite it breaking company rules, then I'd like to find a way to do this. I am very discreet and have been hiding my lustful feelings since day one I got hired.

I have no interest in advancing in this job and certainly don't want work related benefits for fucking a boss. That's the biggest reason the company won't allow anything but I don't give a shit about that. I'm just interested in her.

I'm not looking for any raises or perks at work. I'm just looking to hookup with my hot boss. it's not about her being a boss, she's just hot and sweet and adorable. My type of woman. I'd date her if we were just coworkers.

Is there anyone who has advice? Any guys who have hooked up with their hot female boss? Any ways of dropping hints to feel her out and see if she's the type to try it, to break the rules and give into lust?

 

You already answered your question. Pick one or the other, the job or her, and be willing to risk all else. When you say "I need," you already found your answer.

Hush....an alias

 

Ditto
It never turns out well when there's fucking going on at work between an employee and a supervisor.

You might google "Monica Lewinski" for a good example of why it is a recipe for disaster.

 

Never any good comes out of getting your meat and bread at the same store.

 

Yup I wouldn't.

 

The heart wants what the heart wants.
Start looking for another job while you make your move.
Whether she wants you or not, you will need another job.

 

The heart has nothing to do with this case. Maybe another body part.

 

You're below her pay grade...

 

You are kidding right ??? That is like walking up to the Lion enclosure at the zoo and wanting to "pet the nice kitty" lol. That will always work out well ...

If you don't have a read on her you are asking for trouble unless she is giving off a vibe. Not to seem too arrogant (that ship has sailed), women are not hard to read through body language and there are telltale signs like direct eye contact when speaking as well as little indicators of her comfort level around you like being attentive and even playing with her hair as you talk. Try something witty to see if she laughs/giggles at it to break the ice.

Fuck, I could go on for pages but there is no sense taking you into the deep end if you don't know how to swim lol.

I once had a similar situation but I have swam with sharks so knew how to proceed, but sometimes you just need to say wtf and come straight out with it. "I hope I am not overstepping my bounds but I find you very attractive" worked for me, plus I'm easy on the eyes so that helped LOL.

I wish you luck but you might want to talk to a female friend/sister and do a mock run on her before you "walk the plank". Nothing good ever came out of not trying though if that helps ...

Funny thing is, the last guy I "coached" through this at a bar, the woman ended up giving me her phone number lol.

I will say one thing though bro, you aren't showing anything that supports your username LOL.

 

Having been asked elsewhere if I was ever fired from a job, this was one of my replies:

...Lastly I was fired by a strip club owner in Michigan when oddly his wife started coming in more and more hanging around. That part he didn't mind, in fact he was glad she was there. He didn't even mind me gradually being out on the floor less and less. What he didn't appreciate was walking into his office finding me plowing his wife bent over his desk with a huge strap-on with her screaming "oh yes fuck me harder", and even more so noting her face looked like a glazed doughnut from having gone down on me before hand as he chewed us out... and really didn't appreciate my huge black sopped rubber cock pointing at him as I listened to him rail on us.

When he found out it had been two weeks of this multiple times a day he was really pissed. When his wife told him "fuck you, I'll go live with Nikki" (huh wha? ), he solved both his and now my problem by firing me on the spot .

Guess I'm not a team player

Hush.....an alias

 

Hmmmm, what pray tell is that old saying, oh ya Don't dip your pen in company ink ...

 

It's against the company rules for "superiors and inferiors" to have a sexual relationship..... FFS!!!, which fascist country do you live in????.

Do they really have control of your life outside of the company....

 

I'd say get her a cup of coffee and add some of your cream to it. If she takes a drink and smiles, she is yours.

 

I am certain that you are way too immature to go down this road, keep your head down now that you actually have a job as finding another is going to be a struggle for you.

 

My boss was so hot, she fired me. Get it? Huh, huh, get it, huh?



Hush....an alias

 

Sounds like you are simply infatuated with her and you have no idea if she would have any interest in you. My advice would be to look elsewhere for romance.

 

Never shit where you eat! So ends the lesson...............

 

I suggest against it. If you two don't know one another well enough for this to be more than a passing arousal and she's not giving off vibes, you're better off not risking your job. Plenty of other fish in the sea.

Try writing stories or a diary (journal) to get the fantasies out. Just...make sure you leave them at home.

 

Keep it in your pants and increase your bank.