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Sex with boss was a thrill, until she demanded too much

cropped shot of businesswoman flirting with colleague at workplace in office

DEAR DEIDRE: SEX with my boss was a thrill, until she started wanting more. 

Now I want to cool things off, but she won’t leave me alone, and I’m scared that if I say no my job will be at risk.

I’m a 28-year-old man, and my female boss is 40.

I work for an estate agency. When I joined last year, I found my boss very attractive.

She has a gorgeous figure and looks far younger than her age.

She made it clear she was interested in me, and I’ll admit I was flattered. We flirted in the office, and she’d accidentally on purpose brush my leg as she went past. 

I found myself working late so I could spend time alone with her.

I’d never been with an older woman, and the prospect was exciting.

One night, after everyone else had left, she asked if I wanted to share a drink and a takeaway in the office.

We ended up back at her house. The sex was amazing – not least because I knew it was so wrong.

She had a much higher libido than any of my ex girlfriends, and she didn’t lack confidence.

The next day in the office, we kept exchanging glances, and having quick kisses in the staff kitchen. Nobody else had a clue. 

Since then, we’ve had regular sex sessions. But my feelings for her are starting to cool.

I’ve fallen for someone else – a girl my age. 

But my boss won’t let me go. When I tried to cool things off, she said she missed me.

Now, when she wants to see me, I have to lie to my new girlfriend, saying I’m working late.

And I fear that if I end my affair with my boss, she might take it out on me at work – or even sack me.

What should I do?

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DEIDRE SAYS: You need to tell your boss it’s over.

Tell her you think she’s great, and you’ve had a wonderful time, but you have met someone else.

It’s unlikely she’ll say anything. She’s been highly unprofessional by getting involved with you, and if anyone else finds out, her career could be at risk.

From now on, be professional at work. No more flirting or late nights alone with her.

If working with her gets too uncomfortable, you could think about looking for a new job.  

My support pack, Standing Up For Yourself, should help you have this conversation effectively.

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Fill out and submit our easy-to-use and confidential form and the Dear Deidre team will get back to you.

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