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Memoir - He wanted to clarify that I would be encouraged to wear high heels, short skirts and tight-fitting clothes in general

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May More 💜
Dec 03, 2025
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Attractive woman — long legs and high heels.
Deposit Photos Standard Licence Author iancucristi

A while ago I was reading this story by Jordan Lubov, about a waitress who breaks the rules regarding her work uniform, and as a result is punished — in a very kinky way — by her boss.

It reminded me of when I was a waitress in an upmarket wine bar and served people for money… I too, was told what to wear. At the time - the late 80s - I could see the benefits for myself and the business, and so stuck to the dress code. Now after reading Jordan’s story, I am wondering if my very attractive boss would have put me across his knee if I had disobeyed!

Sadly, I will never know.

Before I landed the job, I’d never considered waiting tables. At the time, I was a student and needed some extra cash.

It all started early one evening when I was meeting a friend in London. (A story of a girl’s night out I must tell one day!) We popped into this city wine bar — not far from Fleet Street in London, and were served by the owner — a very attractive middle-aged man. It wasn’t until weeks later, I found out he had been a popular and talented football player — in his hey-day.

After chatting with my friend and me, we learned he was looking for a waitress. The bar rarely opened after 7pm, but was extremely popular at lunchtime with reporters and money brokers. I was studying for my degree in London, and luckily the days he was busiest were precisely the two I had free.

I am tall, with long legs, a cleavage and in those days I was young too! My new boss explained his clients expected excellent service from attractive bar staff. He could see I fitted the bill but wanted to clarify that I would be encouraged to wear high heels, short skirts and/or tight-fitting clothes in general.

The hourly rate was very good so without hesitation, even though I had never been a waitress before, I asked him when I could start.

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From the first moment, I loved it. I worked with a gorgeous and very sexy Dutch girl, and we soon learned, along with a fab female chef from New Zealand, that we made a great team.

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