I'm thinking of hiring my SB as a personal assistant. Would that be crazy or par for the course?  

It would be great to hear from people who have had experiences doing this sort of arrangement.

It's YOUR COMPANY.......What could possibly go wrong?

That is a terrible idea.  Even if you were just normally dating it's a risk.  You are setting yourself up to give her a huge payout.

The list of things that could go horribly wrong is endless.

That is a very Trumpian thing to do. Hey, if there a problem you will get a pardon, or an endorsement and maybe a payout

There is no way on earth to do this and keep it secret.  

 
Unless it's a small company, 100% owned by you, and you have no concerns about all employees, customers, friends, family and vendors knowing you are fucking your assistant... Let alone fucking her for cash or other compensation (like her job), it's a terrible idea. Even then...  

 
I'll give two simple tests to figure this out:  

 
Test 1: Will the legal costs of defending yourself from lawsuits for sexual harassment, creating a hostile working environment (for your other employees, customers and vendors), regulatory non-compliance, and divorce, be less than her allowance?  

 
Test 2: Are you willing to see yourself on every major and minor news outlet and social media channel in a story labeling you a predator of vulnerable women?  

 
If the answer to either or both is no... hire someone else and see your SB on the DL.  

 
Life is good

 
The Cat

I actually came very close to doing something like this once, so I understand why it sounds tempting in theory.

A very regular gentleman of mine had a legitimate position open at his company. I submitted a real resume, met with his partner for an actual interview, and he may or may not have “helped” my resume sound a little more aligned with the job requirements beforehand. 😉 At the time, it felt exciting and flattering. There was a part of me that thought, why not? We already liked each other, there was trust, and it sounded like a way to blend something comfortable with something practical.

But the more I thought about it, the more I realized the problem was exactly that: it would blend things that were probably better kept separate.

Part of what makes these arrangements special is the little bit of separation. The anticipation. The escape from regular life. The ability to show up as the best, most charming, most relaxed version of ourselves without invoices, office politics, coworkers, bad moods, deadlines, and daily stress attached to it.

Once you bring that person into your everyday business world, the energy changes. She is no longer just your beautiful little secret escape. Now she is in your calendar, your meetings, your payroll, your office conversations, your company problems, and possibly your employees’ curiosity. That sparkle can turn very ordinary very quickly.

And from her side, there are complications too. What happens when she has a beautiful FMTY opportunity, travel date, or private booking that conflicts with your company schedule? What happens if the personal connection changes but the job is still there? What happens if one of you starts feeling entitled to more access, more flexibility, more emotion, or more explanation because now there are two relationships happening at once?

I’m not saying it could never work. Grown people make their own choices. But for me, I realized I would rather preserve the magic than turn something special into something tangled.

Sometimes the fantasy works because it has room to breathe.

My vote? Hire a wonderful personal assistant.
Keep your SB as the part of your life that still feels deliciously separate. 💋

Please tell me this isn’t a real question and you were bored.

-- Modified on 5/19/2026 8:59:13 PM

You’d be crazy to hire any woman that you’re sexually involved with, let alone someone that you pay for sexual favors.  There is little to no upside and the downside could be catastrophic to you, your reputation - both personally as well as in the local business community - and the business itself. Giving a pro your business contact info for verification is stupid enough, actually hiring one crosses the line of insanity.  I’m hoping that in this case this is nothing more than a troll post; if not then I’m surprised you were fortunate enough to own a business in the first place.  

One escort I knew was on company payroll for insurance but all she did was “secretary “ 😂

END OF MESSAGE

Blow jobs on your lunch break sounds like a win to me

I haven't experienced this situation, I would say yes go for it!
I mean what could go wrong!
Sex at lunch time in the break room, quickies at break times and don't forget video so you can jack off when you let her do actual work.
Holy fuck what a great idea^^!

I will add that anyone that has ever been a party to the meltdown and payback from a dumped SB will know the answer without asking.  

If you are the type to want to self destruct, this is a great way to do it.  

Good luck!

"Never get your meat where you get your bread."
"Never dip your pen in company ink."

Put down that glass dick and stop sucking on the pipe.

'IF' and only if you do this, sign over everything you have and protect it.

yeah yeah, you are only trying to help her/him out, sure you are. You just want to keep your eye on things.

Pussy is a wonderful thing, you should love it and cuddle up with it as much as you can, where you can. But 'NEVER' fall in love with it.  

Today women under 30yrs old are open to being a SB, no problem.  

Hire her as a personal assistant, hahahaha more like assistant these nuts.

P.S. your laywer is waiting for you to call

I always heard it was “never get your honey where you get your money.”

 
Anyways as to the OP, I don’t mean to pile on but this is a worse idea than the guy who wanted to visit the provider who lived in his building. This is virtually guaranteed to come out.  

 
Maybe when she is just having a bad day and takes it out on the guy she’s having sex with. Maybe when she realizes that she’s got you by the short curly hairs and starts demanding more and more. Maybe one day when you get horny and somebody walks in to find you sandwiched between her and your desk. Whatever. It’s going to come out.  

 
In addition to the legal troubles already mentioned by others such as harassment, hostile workplace, etc. it’s going to look like you were using money from the business to pay for your personal sex romps. To the wrong person, that can sound like fraud. That may not “stick” but you won’t have any fun defending yourself against it.

I had a secretary embezzle from me. FIRST question out of my lawyers mouth was, "Are you fucking her?" He asked 2X, hard. If I had, the $15k was HERS!!!  

Don't do it!  

It was one thing to do this pre-internet when a GF/SB meltdown was limited to word of mouth. I know lots of guys who had their GFs/SBs on their payroll in one way or another back then. But, in the age of the internet (and #MeToo) it's the dumbest idea ever because a jilted GF/SB can put you on blast and your stupidity will be exposed to the entire world in a Cincinnati second, limited only by who happens to see and repost her hateful missives. Is the ability to write off $5k - $10k a month (maybe $1.5-2k in tax savings) really worth the potential disaster? My vote is NO!

You should definitely do it, there is absolutely no downside........

Marissa, this is beautifully and thoughtfully expressed. Thanks!

END OF MESSAGE

END OF MESSAGE

She'll own the whole thing!