My submissive boss

ANDREA!! - May 25 2025 at 13:58
For the last 5 years I’ve worked at a small business, it’s a great place with only 10 staff who all get on great with one another including our boss who’s a 55 yr old married man. Now a few months ago we all went out on a staff night out and I ended up in a deep conversation with my boss who decided in his very drunken condition to spill his deepest secrets to me.
I was slightly shocked but intrigued as he admitted his kinks and fantasies for dominant women, being ordered about and humiliated and how his wife didn’t understand and how sad he was.
At work on the Monday morning he was very sheepish and couldn’t look at me and this went on for a couple of days, I’ve got to admit I was quite enjoying his discomfort so I decided to confront him, I went into his office and told him to stop being so pathetic and that his secret was safe with me, but I did make sure to laugh at him and ordered him to say sorry for being pathetic. Which he did, and immediately loved that I had power over him.
Now back to present day he is basically putty in my hands, I can order him to do anything and he’ll obey no matter how ridiculous it is, he gets on his hands and knees and kisses my shoes when I go in his office, I ordered him to wear women’s underwear under his clothes including tights, which he changes into when he arrives, he pays for my shopping and car and life is so much easier and more amusing having a slave.
However I also feel dreadfully guilty, his wife and grown up children are lovely and I’m just using his kinks for my benefit I’m pretty sure my colleagues suspect something is going on as I’m in his office multiple times a day. I’ve also met someone who I really like out of work and it feels like I’m cheating on him.
Do I tell my ‘boss’ we need to stop this and hope he accepts it or do I start looking for a new job or just carry on taking the extra money as it’s not like we are really having an affair and just accept the guilt.
As with everything else in life, what goes round comes around. Do keep on feeling dreadfully guilty at the great place where you work. If you really don't have the smarts to know what to do, then you're not likely to find the answer here...& there's no doubt about your colleagues suspecting, because they always do.
This thread reads like some made-up story. I hope it is. Honestly, everything about this just sounds awful.
If, by some chance, it is real, then you are fishing for drama.
Whassallthis??
"For the last 5 years I’ve worked at a small business, it’s a great place with only 10 staff who all get on great with one another including our boss who’s a 55 yr old married man. Now a few months ago we all went out on a staff night out and I ended up in a deep conversation with my boss who decided in his very drunken condition to spill his deepest secrets to me.
I was slightly shocked but intrigued as he admitted his kinks and fantasies for dominant women, being ordered about and humiliated and how his wife didn’t understand and how sad he was. "
Er... THAT'S not spilling his deepest secrets to you - it's an highly inappropriate attempt to seduce you!
"At work on the Monday morning he was very sheepish and couldn’t look at me and this went on for a couple of days,"
Okay, so he really did lose all boss-ly control, then, cos evidence shows he regretted it to point of cringeworthy, and didn't know where to put himself, rather than continued on, just more subtly without the excuse of drink (which some might). Good, that's something.
"I’ve got to admit I was quite enjoying his discomfort"
Huh?
WHY?
Do you have some banked-up resentments towards him or something?
" so I decided to confront him, I went into his office and told him to stop being so pathetic and that his secret was safe with me, but I did make sure to laugh at him and ordered him to say sorry for being pathetic. Which he did, and immediately loved that I had power over him."
Whaaat?
Okay. I see.
"Now back to present day he is basically putty in my hands, I can order him to do anything and he’ll obey no matter how ridiculous it is, he gets on his hands and knees and kisses my shoes when I go in his office, I ordered him to wear women’s underwear under his clothes including tights, which he changes into when he arrives, he pays for my shopping and car and life is so much easier and more amusing having a slave.
However I also feel dreadfully guilty, his wife and grown up children are lovely and I’m just using his kinks for my benefit I’m pretty sure my colleagues suspect something is going on as I’m in his office multiple times a day. I’ve also met someone who I really like out of work and it feels like I’m cheating on him.
Do I tell my ‘boss’ we need to stop this and hope he accepts it or do I start looking for a new job or just carry on taking the extra money as it’s not like we are really having an affair and just accept the guilt."
Yeah, very amuszzzzzzzzzzzzzzzz.................
Is Mummy there? Shall I talk to Mummy?
Mannie, now I've got a mo to ask you: would you like 'Veteran Poster-Advisor' on your banner? I think you need massive recognition too (it's over a decade you've been working here, right? Or is it even longer??).
Wanna?
...In fact, you were here LONG before Dec 2013, right?
yeah why not.. but I forgotten when I first stumbled across this forum..must have been around 2012 or so. cheers
You may as well as you're doing the role anyway, haha.
Cool, I'll talk to Richard and get back to you! :)
We need to get better organised, I think, now that the world and our situations have changed and we no longer have the time and space to be more full-time like we used to. (Crikey, to think I used to have my ducks so in a row I was capable of being on daily...!)
You'd been on for more than a year when I joined, though, I'm sure you had...I thought 2 years prior to me.... You sure it wasn't 2011? Or do you mean early 2012?
Actually, thinking about it, Richard might know...(?)
Right - chat again soon...
Honestly, I'll go right out on a limb and say that Manalone at least deserves the same title I have here.
He's been around here longer than both of us, and he gives solid advice. He also doesn't ramble on quite as much as we do sometimes, and I think it's important to have some people here who give advice in different ways, because what works for one person might not work for everyone.
Yes, I know he does, but as I explained on another thread (pay attention at the back there? haha), he declined because he can't commit that much. Veteran Poster-Advisor gives him the recognition without losing his freedom to post just whenever he can. :) He is considered staff, though, he's been so consistently present overall.
PS: Rambling has its uses. Comfort, usually, through greater sense of conversation...like a pen-pal. ...which is just as well because I couldn't be succinct if you paid me!