Saturday , January 29 2022

Submissive boss yields to his dominant personal assistant

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.

About dss

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