Sub to My PA Ch. 01

Story Info
Submissive boss yields to his dominant personal assistant.
3.6k words
4.49
47.1k
51

Part 1 of the 4 part series

Updated 06/10/2023
Created 06/25/2021
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Sandra was my PA and so much more. She organized my business life, accompanied me on business trips, booked hotels and transport, dealt with clients and suppliers, organized me, hired and fired office staff and production workers, managed company discipline and productivity and supported me in every aspect of my working life.

As well as work she was a regular visitor to my home and became part of the family. She and my wife Debra got on very well; became close friends. For which I was very grateful for that. She'd seen our two children; Dan and Amy grow up from childhood to become young adults and they too trusted her and confided in her. I think Sandra knew more about my wife and children than I did!

Any worries I had initially had that Debra would be jealous of the amount of time Sandra and I spent together or suspicious that there was more to our relationship than work had long ago proved to be unfounded.

When I broached this with Debra some years ago, thinking I would have to persuade her that mine and Sandra's relationship was not in any way sexual she just laughed at me:

"Don't flatter yourself Dave. Sandra is dedicated to her job. She is professional and loyal and fiercely protective of you as manager and of the business. But that's it. She actually doesn't think all that highly of you, as a man." She giggled. "She's very insightful actually; and funny. We've had some good talks about men, sex, you; girl talk - you don't need to know! You don't need to worry about your relationship with Sandra going beyond the strictly professional, and neither do I!"

Which was a relief, I suppose. Even if it left me feeling rather inadequate.

She continued:

"Anyway Dave, you wouldn't know what to do with a woman like Sandra." She smiled at me. "She's quite a demanding lady who likes her men much...bigger... She'd eat you alive."

I nodded, turned red and looked away.

Debra was alluding to the small size of my penis and my submissive nature.

It wasn't something she mentioned very often although I had often wished she would; had often begged her to.

When we first got together Debra had teased me about how small my dick is and told me about her well hung ex-boyfriends, which, to my shame I found arousing.

In the early days of our relationship we even played kinky BDSM games where she spanked me, scolded me and made me behave very submissively. Even then though she didn't like to make fun of my small penis; especially when I admitted (to her disgust) that it turned me on.

She did have a few of one night stands and a short affair with a male colleague around the time we were married and admitted it had been 'just sex and just about their dicks' but she felt terribly guilty about it and swore never to do it again or talk about it.

Of course I'd been masturbating over the memory and humiliation of her infidelity ever since.

Not long after we got married we began trying to start a family so the infidelity and kinky games ended.

And, when Dan and Amy were born, so did our sex life.

I satisfied myself by reading and watching cuckold and female domination porn and wanking every night. But I never talked about it with Debra. It was my private world. Secret. Shameful.

Our sex life became less important as we concentrated on bring up our children, Dan and Amy and making a happy home environment. They grew up. Dan's 21 years old now, he plays football and is studying at a nearby university. He comes home every other weekend so we can do his laundry and his mother can mollycoddle him. Amy's 19. She still lives at home. She plays football like her brother, works at a local sports centre and is training to be a sports physiotherapist and coach.

As well as family I concentrated on building my business. I'm a partner in a company which I developed and now run with the support of an asset management firm. They leave me in charge of product development, sales, contracts and logistics.

Which is where Sandra comes in.

I'm great at the technical side and being helpful to clients, contractors and suppliers and usually that's enough. The products sell themselves and the fact that nobody else knows how to do what we do means I don't usually have to play business hardball with business partners.

But when I do need to be assertive - when a contractor or a client or a competitor is being aggressive or trying to pull a fast one - I go to pieces.

My submissive side comes to the surface.

I do think it's because of my small penis. Suddenly I become very aware of all the big assertive guys with their big dicks in the boardroom and totally conscious of how small my dick is. I imagine that they all know that I have a tiny penis. I even start to get an erection.

That's when Sandra takes over.

She finds a reason to get me out of the meeting or to take a back seat. Then she explains that she has been authorized to act on my behalf.

She's fearless, ruthless, assertive and quick-witted. By the time negotiations are over the big assertive macho players have folded are either scurrying off with their tails between their legs or at Sandra's beck and call.

I don't take any of this for granted. I am so grateful to her and rather ashamed. I praise Sandra but she doesn't like listening to my self-deprecating gratitude and shuts me up:

"Don't worry about it Dave. I like doing this bit. I couldn't do all that technical stuff and being helpful to people that you do. You're just too nice. You can't help it. I'm a total bitch and I love it. Plus at least half of those guys have given me their number and want to fuck me now."

Sandra organizes our hotels, transport, meals, conference facilities, everything.. She even brought my suits, shirts, shoes, underwear along because she knows from experience that I'd forget at least one item.

We've always had adjoining rooms at hotels. Sometimes we'd be wined and dined by contractors or clients celebrating a new contract or partnership until late and we'd come back to the hotel drunk.

Occasionally Sandra brought one or two of the guys from our meetings back to fuck her.

Our business associates have always acted like they thought me and Sandra were sleeping together. When we go to the toilet they're always making jokes that I was a lucky guy to be fucking such a hot PA. Apparently that was the usual arrangement. When I denied it they always appeared to think a little less of me.

The guys she brought back to the hotel would make me feel like the cuckold boss as they made out with Sandra in the back of our taxi. I would stay up late at night wanking my little dick listening to the sound of them fucking through the hotel wall. She's very loud when she's cumming. I've never heard sounds like that from any woman I've slept with.

Whatever she'd done the night before I would always wake to find Sandra up before me. Always dressed immaculately having paid the hotel bill (including any extras like my minibar, sex chat lines or porn channels), packed my bag, tidied my room of porn mags and left my travel clothes ironed and ready at the foot of my bed.

She's a marvel.

Back at the office and production plant Sandra carried out a similar role.

While I made encouraging speeches and tried to motivate staff with my optimism and gratitude Sandra dealt with the troublemakers ruthlessly and put the fear of God into every employee from cleaner to finance director.

There were mutterings about our relationship - the usual misogynist clichés - 'you can see which one of them wears the trousers' and 'one of them's got a massive pair of balls and it's not him' - but it didn't do us any harm.

As Sandra told me: "It's the old 'good cop/bad cop' trick' don't worry about it - you keep doing what you do best and I'll do what I do."

It was on one of our business trips that our relationship changed.

We were in the final negotiations with a supply chain company which had a very macho and aggressive culture. The meetings had been particularly fraught. I went to pieces. Like I said; all I could think about was their cocks and my small penis. I went red and clammed up

Sandra stepped in as usual and took control.

These guys weren't nice and when they were cornered they became nastier. They engaged in a strategy of brinkmanship issuing hollow threats and obvious blackmail. Sandra cheerfully called their bluff and, predictably, the deal they ended up with was worse than it would have been if they'd behaved with more integrity.

Once we'd signed the head contracts, shook hands and sent the lawyers off to fill in the details they still had to take us out for dinner to celebrate our 'partnership'.

The evening was as unpleasant as the negotiations had been. Before dinner they challenged us to tequila slammers. Which was fine; both Sandra and I can hold our liquor.

They got drunk and during the meal they drank heavily and argued with one another at the restaurant.

After the meal they drove us to a seedy strip bar in a rough side of their city obviously hoping to unsettle us and make us uncomfortable.

That didn't work.

At the strip joint Sandra continued to drink the guys under the table. Then she bought a round of drinks for a group of cowboys she'd got talking to at the bar. She quickly got to know the names of the dancers and waitresses. Pretty soon she was the most popular person and looked like she'd been drinking there for years.

She even got our new partners up on the stage dancing drunkenly, much to the amusement of the cowboys, the girls and the other punters.

I was content to sit at the bar and watch the strippers.

Which is what I was doing when Sandra grabbed me and pulled me quickly out of the club and into a waiting taxi. The cab sped away just as I saw our partners come running out onto the parking lot shouting angrily, waving their fists and cursing in our direction.

Sandra leaned forward to the driver:

"Thanks for waiting so long for us Leo. Appreciate your patience. You know which hotel we're staying at don't you?"

Leo smiled back as he sped out of the district: "No problem madam. I was told to wait as long as it took. You left a little earlier than I expected. Some nice friends you have back there."

Sandra explained to me that she'd arranged for a car to wait outside the club as soon as she knew where we were going.

"You know what I'm like with planning ahead Dave. It's my weakness. Prepare for every contingency. And I have to say the outcome of the night was not unpredictable. I tried so hard to be nice as well. Those men are not gentlemen. I gave them fair warning but some people don't understand the word 'No' until you've ripped their balls off in front of a crowd of cowboys and strippers."

I was shocked: "You did what?"

She smiled at me: "Don't worry. I left their balls attached. They're just angry because I hurt their male pride."

As we drove through town Sandra was more excited and talkative than I'd ever seen her. She chatted to Leo about basketball and seemed to know everything about his local team.

As we arrived at the hotel she slipped me a wedge of notes to give to Leo.

"Thanks Leo. You came highly recommended and you did not disappoint. My boss here is very grateful and he insists you accept his gift. Don't refuse the big man!"

I tried to live up to her hype by nonchalantly passing the notes into Leo's hand like I'd seen in the gangster movies. Leo gave me a wink and whispered: "You take care sir. Quite a woman you have there."

As we walked into the hotel Sandra linked my arm as if she was my adoring mistress. The hotel bar was about to close but she demanded that the night manager keep the bar open and handed the bartender a roll of notes.

We had a couple of whiskeys and discussed the day's business. Sandra thought the negotiations had been fun. She kept poking fun at our business associates and pointing out failings that I hadn't noticed; one had toothpaste on his chin, another kept poking his ear till it went red, one came back from the bathroom with the front of his trousers wet, two of them kept looking at her tits then looking away when she caught their eyes.

She made me laugh and see the whole thing in a different light.

"I wish I could see things the way you do Sandra. I really do."

I was drunk and I wanted to admit to her that I just kept thinking about how much bigger their dicks were than mine.

"How do you see things Dave? What's going through your mind when it gets tough? What happens to you?"

"Honestly Sandra? You want the truth? Okay. What goes through my mind is my dick being smaller than their big dicks and then that's all I can think about."

She looked at me and drained her glass of whisky:

"Yeah. Shit. That'll do it. That is not going to give you the psychological advantage you need in business negotiations."

That made us both laugh.

She leaned close to me: "I don't have that problem. I don't have a dick. But I've seen a lot of dicks. Dicks are nothing special."

She noticed the barkeep was listening closely to our conversation.

"Dave, we need to take this somewhere more private. Come up to my room."

Sandra got a bottle of brandy from the bar: "Charge it to my boss."

We let the barkeep close up and went upstairs.

Sandra had been in my hotel room on every trip; to wake me up, to tidy up, to organize my wardrobe, but I had never once been inside hers.

She stopped me as I went to enter.

"Not so fast big man. Entering my room is a privilege and I don't want you to think you can just swan in here. First you need to ask my permission. Properly. On your knees"

I was very drunk but I realized she was serious. I sank to the floor and looked up at her with my hands pressed together.

"Please Sandra. Will you grant me the privilege of being allowed into your room."

She looked down at me with a frown. I was suddenly aware of how powerful she was, her long legs, her broad hips and her breasts. Instinctively I lowered my head and kissed her boots. Some other guests came out of the lift and walked passed us down the corridor, whispering. I cowered on the floor hoping Sandra would wait till they'd gone but she spoke to them. They were two women she'd met earlier and they asked how the meeting had gone. Sandra told me to get up and introduced me as her boss. They giggled and congratulated Sandra on having me 'well trained'. Sandra replied: "Oh we've a way to go yet!"

Sandra's room was immaculate. Sandra's outfits were neatly folded. There was a rail of my outfits with notes attached. The desk had a laptop, a collection of disposable mobile phones, a map of the city and photographs of our business partners with post it notes stuck on them. There were roses in vases and a bottle of champagne in a bucket.

Sandra went to the minibar and took 2 cut glass tumblers and poured brandy.

"This is the centre of operations."

We sat together on her sofa and clinked glasses.

She looked at me.

"So. You were saying..."

I began to stutter:

"What were we talking about?"

"Dicks. But let's chill a bit first."

She put the television on to the porn channel. It showed a scene where a man in a suit was tying a woman; probably his secretary, to a desk, blindfolding her and smacking her bottom with a slipper. The girl whimpered with pleasure.

"Oh my god, this is perfect; 50 Shades of Grey! It's halfway through. Let's watch it for a bit."

We watched as the dominant boss subjected his willing secretary to various punishments and tied her up.

I found it arousing. It's not what I usually find erotic. But sitting next to my PA watching scenarios that were so contrary to our own relationship was somehow humiliating.

Sandra kept laughing at it.

"Haven't you seen this before Dave? Not even read the book? I thought everyone had."

"Do you like it?"

"Not much. I don't really relate to it. Sure I like dominant men - on the rare occasion I find one who can handle me; but I'm naturally dominant myself. What about you?"

I muttered something.

Sandra laughed: "Sorry Dave. Silly question. I know you couldn't be dominant if you wanted to. Debra told me all about how she used to whip you and make you obey her. And that you wanted to carry on being her sub but she couldn't be bothered."

I looked shocked.

"Come on Dave. I get people to tell me things. It's what I do. Anyway; me and Debra are close and us girls talk. She told me all about your little dick. How you get turned on by her fucking other guys and teasing you about how small it is. And how frustrated she is. I gave her my advice."

"What was your advice?"

She smiled at me and raised her eyebrows:

"Obviously I told her to fuck other men. Cheat on you. That way she gets the fucking she deserves and craves and you get turned on. But she won't. She's too angry to give you the pleasure and resents that your shortcomings force her to act like a slut. That's why she won't indulge your desire to be submissive and punished. To hurt you. Even though she'd love to smack your arse and punish you."

I took some time to take this in.

"What should I do then?"

There was a pause while Sandra drained her glass. When she looked at me again she seemed like a different person.

"You can start by filling my glass. It's empty."

I hesitated. She became cross and raised her voice:

"Now."

I fetched the bottle and filled her glass.

I sat beside her. Suddenly she smacked my face.

"Get on the floor and say sorry. And mean it."

I did as she said. I knelt at her feet subserviently as she drank.

"I've wanted to do this for a long time. I have a list of all the times you've done something that deserved punishment. All the times you've failed me, been rude to me, annoyed me, acted like you're better than me, disrespected me, ignored me, looked at my tits, looked at my arse, looked at other women when you were with me, made sexist jokes with other men. Every negotiation I had to take over because you were too pathetic, every hotel porn channel bill I had to settle, every sticky dirty mag I had to tidy away, every night I had to listen to you wank your little dick in the room next to mine, every time you criticized your poor wife. And I'm going to smack your bottom for each of those. And you will thank me."

She made me undress. She sneered at my little dick. Then she tied me over the sofa and took a cane out of her bag and whipped me until I cried and begged for mercy.

She left me tied up while she had a shower and got ready for bed. She untied me but only so I could use the toilet. Then she tied me up again and went to bed.

That's how I woke up.

As usual she was dressed immaculately and everything was packed. She applied some cream to my cut and swollen buttocks. I was so grateful. When I was untied she sat on the sofa and let me put my head in her lap while she stroked my head. I found myself crying and thanking her.

My bottom hurt all day on the journey back home.

I tried to talk about what had happened but she told me to wait until we got to the office the following morning. She told me to be at work at 7am.

At home I had to hide my raw bum from Debra and Amy.

Despite my discomfort I found myself erect at the memory of my punishment.

I was still very sore the following day when I arrived at the office to find Sandra sitting at my desk.

Sandra made me undress and kneel before her.

"To everyone you are my boss and I your PA. But the reality is that from now I am your mistress and you are totally under my command. Never forget that for one moment. Your little dick is mine. You will wear these lacy knickers beneath your trousers while at work as a reminder of your subservience to me. And I will punish you every morning when you start work and every night before you go home. The pain in your flesh will serve as a constant reminder of my dominance."

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