There is this young coloured lady at work, really young she is only turning 21 later this year. Slim body, perfectly toned skin, gorgeous massive tits for her size... She is a bit bubbly and shy in the way she acts, sometimes she dresses a bit like a Tom boy and other times like a model!!! At the beginning of this year I have been working with her a bit, a few months ago she wore this mini skirt to work and we were in the elevator together leaving. I made a slightly naughty joke with she thought was cute and we started speaking in our personal capacity also after that.

Basically next week Friday her and I are taking the day off and meeting up at a fancy hotel I booked. We are basically going to fuck each others brains out!!! She has a bf who sends to gave pretty boring and they just have normal sex. Looks like she is willing to do some really dirty things!!!

I can't wait!!!!

Lmao don't jinx yourself

Sounds like a dream, but I'd be really careful with this type of situation bro. Especially given that she's young as you describe her. And presumably she's possibly also junior to you in the hierarchy?

But if you're all set for it, then hey...just take a moment to consider the worst case scenario and let the big head and the little one have a thorough debate. And if the little head wins (most probably) try and have some kind of written proof, if your circumstances allow, that all is consensual and not in contravention of any company policies.

On 2024-06-21 22:43:39 Sir Shadow Hefner said:
Sounds like a dream, but I'd be really careful with this type of situation bro. Especially given that she's young as you describe her. And presumably she's possibly also junior to you in the hierarchy?

But if you're all set for it, then hey...just take a moment to consider the worst case scenario and let the big head and the little one have a thorough debate. And if the little head wins (most probably) try and have some kind of written proof, if your circumstances allow, that all is consensual and not in contravention of any company policies.

all of this is the first thing that came to my mind. the worst case scenario is BAD very very BAD, but hey its not like im his boss.

On 2024-06-21 22:43:39 Sir Shadow Hefner said:
Sounds like a dream, but I'd be really careful with this type of situation bro. Especially given that she's young as you describe her. And presumably she's possibly also junior to you in the hierarchy?

But if you're all set for it, then hey...just take a moment to consider the worst case scenario and let the big head and the little one have a thorough debate. And if the little head wins (most probably) try and have some kind of written proof, if your circumstances allow, that all is consensual and not in contravention of any company policies.

Uttered like a pro...

The vote as it stands is GO FOR IT in the lead!!!

Take your vita boost I suggest Vital for men..... Drink lots of water, eat a couple of bananas and pineapple just in case and find a way to rub one out before you get to her.... Practice breathing, the breathing that is guys know physiologically helps with stopping you from cumming to quick... Then have your fun... Also this is a meeting, You chose to accept AND most importantly SHE accepted so go in confident brother have fun. Remember you are an option that you presented as better sex than she currently is having. So give it your best and don't fuck it up..... Sincerely Good luck.....
To end off remember to be honest because IF you do hit it right she might connect and this will be more than just a one time thing...... Play responsibly and carefully
:)
Speaking as a friend that wished you and her an unforgettable night!!!!

Oh yeah take lube brother just in case :)

This is a bad bad very bad idea. Especially if she is your direct report. There are so many ways this could go sideways.

After this sex session, will she be able to remain professional at work? Will she expect special treatment? Will she listen to you as her boss. Will she be able to keep this on the low and not gossip to colleagues? Do you want that reputation of the boss that sleeps with staff? If things get sour do you know she could file for sexual harassment even if it was initially consensual because she could argue that you being in a position of power (as her boss) she felt coerced to sleep with you. Especially since you mentioned that she is young and I'm assuming she maybe an intern. Do you know she could blackmail you into getting her a promotion?

You may think that you can keep these things discreet but they always have a way of coming out in the workplace. Not to mention what happens if the boyfriend finds out. Do you know what it feels like to have a deranged boyfriend coming to cause a scene at your workplace? I've seen things at work.

Be careful. I wouldn't go through with this if she works in your department or a department that's connected to yours.

U say u though the nawty joke was funny. U booked a very expensive hotel and u say u basicaly gonna fuck each others brains out.
U actualy mean u think she liked the joke and u hope u gonna fuck each others brains out. Next week friday is stil far away. I hope u havent booked the hotel room yet

Don't do it.
In my experience very few of these work relations work out for the better.
It is all good in the beginning when it is still fun and new, but once something goes wrong it goes wrong in a bad way.
Over the years I've seen many irate partners causing kak in the workplace because of such affairs.
Having to explain to the HR manager why you had to dip your pen in the company ink can not be fun and might lead to dismissal - depending on your company's policies.

ESA exists precisely so that you can live out those fantasies without getting into this sort of trouble.