The Boss & Her Secretary


The Boss & Her Secretary




For over 2 decades, I was a Personal Assistant, a P.A. for the CEO of a large American company. It’s fair to say that with this kind of experience, I know my way very well around an office… and most certainly an office scenario.

So when he phoned and asked me for an out-call featuring an office type scenario, how could I possibly refuse?

His “ideal”:

To be the boss and have the secretary come into his office, taking notes etc. (PA themed activities) before she eventually becomes overwhelmed with her workload, then proceeds to turn the tables on the Boss, using a threat such as; “I will show your wife compromising photos of us (pre-doctored) if you don’t take my orders seriously”.. etc.

Not a bad scenario.

My only problem with that was, I AM the boss. Yesterday. Today. Tomorrow. Always.

I take orders from no-one.

Knowing that this particular sub had other interests such as “light blackmail”, feminisation, a little forced bi play.. I decided to give him an out-call he wouldn’t forget in a hurry.


I arrived at a very classy hotel which he had booked specifically for our meeting. He didn’t consider the Chambers on this occasion, to be the most suitable place for our meet to take place as it doesn’t possess an actual office that would work in this situation. Arriving at the check-in desk wearing my full PA outfit as he so respectfully requested, teamed with the beautiful seamed silk stockings and stiletto heels he had purchased for me, I collected the envelope from behind the desk containing the key card (and of course, my tribute) and made my way up to the room.

I entered without knocking, naturally. The room was beautifully lit and was adorned with fine furniture that only added to the entire ambiance. This wasn’t just a room but a small suite and as I made my way through the interior door, I found myself standing in front of him; sitting at a large desk wearing his beautiful quality suit and tie, as expected.

Knowing we were not interested in small talk of any kind, we immediately began.

Or rather – I did.

I removed my coat and asked him to put it on a hanger. As he returned from the wardrobe, he saw that I was holding my handcuffs out towards him. “Put them on”.. I told him. “But I thought...” came his attempted reply.. before I cut it short by hitting him hard across the face. “You thought what? That I would be YOUR secretary? No. We ARE having that secretary scenario, as we agreed.. but we are doing it MY way”.. came my stern reply.

Opening up my travel case, I took out hold-ups, panties, and a little bra-let which I knew would look perfect on him. Then I pulled out the file I had collected on him (ALL PRE-AGREED VIA EMAIL BEFOREHAND) containing the usual requested personal information documents of his in order to ensure my safety and security on any out-call. This information is always required, a fact of which he understood and was very keen to do (to show his sincerity when booking his session with me) EVEN when he knew he had asked me for Financial Blackmail as part of our agreed scenario (up to an agreed limit).

Fastening him to the leg of the desk with the handcuffs, I made my way off to change. Returning in my much preferred “Hot Boss” outfit, I sat down in front of him, holding out his file in my hands and taking out the pages, one by one. Full name, home address, his employment details, telephone number, etc. I had everything I needed to make his dream come true.

Remember – he begged me for this when he emailed his ideal scenario / situation over to me prior to our meet.

I laid it all out in front of him and told him clearly and in no uncertain terms, exactly what I would do with this paperwork should he disobey me or try to say no to anything I asked of him over the coming few hours. I love that beautiful moment when you see the colour drain from his face… the fear growing in his eyes .. almost as fast as the erection is growing in his expensive suit.

He wants this. He’s always wanted this. And now, I am here to give it to him.

I strip him myself, slowly. His little penis is glistening by the time I remove his underwear – he’s so excited.. bless him. Unfastening his hands, he’s now instructed to dress; as I hand him the items I have so thoughtfully brought with me. I saw the look in his eyes as they quickly shifted from myself to the stockings and panties he was now nervously holding (panties of my very own, I might add!).. wondering if I am serious. Raising the leather paddle in my hand slowly upwards towards his face, he dresses without a single word of complaint. A wise choice indeed.

What follows is 2 hours of absolute pure unadulterated office enjoyment, certainly on my part anyway. He took a letter; having his hands slapped like the bitch he is when he made mistakes. He picked up all those scattered dropped paper-clips .. being careful NOT to bend those knees whilst keeping the legs apart… such a fun view for me as I watch his cock and balls squeeze out from the sides of the lace panties. I taunted him, teased him, sexually and verbally harassed him before I eventually let him prepare the Boss’s lunch with Champagne.

Then came the real fun.

Strapon worship is always the most delightful sight, from my point of view. I love to watch them drool as they try to control their gagging when I fuck their faces. He was no different. Tieing him to the bedposts spread-eagled, I knelt down over his face and fucked his mouth for at least half an hour. By the time I had finished, he could barely move his jaw. Such fun! All the while, my electric butt plug was buzzing away merrily in his tight arse, forcing his cock to maintain its erection and pulsate with a mixture of pure pain and pleasure, ALL controlled by MY VOICE! At this point, he was pretty much broken. Slutified, ultra submissive, begging for my attention, eyes never leaving me for a moment, unsure for what may come next… but wanting whatever it may be!

Before he knew it, he was on his belly, laying on the very desk that he wanted me, HIS MISTRESS, to sit behind taking notes! His laptop was open, as required for the session; and he is facing the screen, hands cuffed behind his back, laying on his belly, face side on watching in the mirror. Holding his hands tightly just a little higher up his back than is comfortable, he watches as my lube covered strap on moves towards his arsehole. Then, whipping out the E-stim Flange (electric butt plug) and replace it almost immediately with my strap-on. It isn’t particularly big... but when you aren’t expecting it – it can take your panting breath away- apparently.

Slowly, I begin fucking him. Forcing my dildo ever deeper into his swiftly gaping arsehole, I soon feel him pushing back.. just that little bit more each time. He wants it, badly.

“Now my little slutty secretary, it’s time to pay back all of that petty cash you owe the company”… I whisper in his ear as I am still slowly sliding that strap on in and out. “You’re going to pay me back.. by online shopping.. RIGHT NOW”… and the handcuffs are removed.

We shop. Oh, darlings do we shop! That secretary really owed a small fortune to the company.. but whilst the debt was swiftly paid by in just a couple of clicks on his laptop, this slutty secretary just wanted to pay more and more… with each click of the purchase button, came 10 seconds of good, hard fucking, banging that slutty man-pussy until I could hear his balls slapping against the desk. “CLICK IT AGAIN, CLICK IT AGAIN” he panted... That is one ass-greedy secretary! And without me even realising, what a mess was made on the formerly highly shined desk by the time I withdrew from his gaping arsehole! Apparently, he had never before experienced a prostate orgasm...

I left him where I fucked him.

Bent over the desk, one hand now cuffed in front of him, one around the desk leg … knowing the keys were in the suite for sure – somewhere. I would tell him where, but only once the cab had returned me home… and for a price, naturally.

Was he okay? Did he ever get his key back? Did his arse ever recover? Is he permanently scarred by his “ordeal”?

I will ask him when he returns, as he has almost insisted on doing, in 8 weeks' time..!