I have finally gone back to work and now I am having sex with my boss

DEAR DEIDRE: I AM having great sex with my boss in the boardroom at work. We chat over drinks, too, but neither of us has the slightest idea what any of it means.

I’m a 23-year-old guy, she’s 38 and we work for a satellite internet firm. We have been working throughout the Covid crisis, sometimes from home but lately back in the office full-time.

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The pressure was immense to keep the wheels turning and it was stressful to deal with that at home.

It was such a relief to get back to the office and to have somewhere to offload the stress for a change.

It was great to be joking and laughing with colleagues again.

This is the first time I’ve had a female boss and I was in awe of the way she handles herself.

She copes with the pressure and manages the staff while still having a good laugh.

Not only that but she always looks fit and well-groomed, with looks and a figure most women would envy.

I knew she was older than me but still fancied her big-time although I reckoned she was out of my league.

It all started on the Friday of the week we went back to work. We’d been working flat-out and she brought in wine and some beers to end the week.

Most of the others drifted off home before too long but I stayed behind, as it felt really good to be chatting with her after hours.

I sank a few beers and she had a few glasses of wine. I could hardly believe she was flirting with me.

She told me to stop being “socially distant” and come to sit down on the couch, as she wanted to tell me how well I had done.

I got overheated and kissed her — but it seemed like I’d done the right thing.

She leaned back, I took off my jacket and gave it my all. It was great.


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Since then we’ve been “working late” in the office on Fridays and having sex.

I don’t know where it’s going to end.

DEIDRE SAYS: It sounds fun but I doubt you would be writing to me if you were totally fine about this.

She is clearly impressive but you need to remember she is still your boss – and that means you are treading on dangerous ground.

I doubt she is offering more than a bit of relief at the end of the week. That is fine until something goes wrong.

Obviously you are both taking a health risk but what if somebody sees you?

Would she have your back? You could end up taking the blame if that suited her.

What if you met someone else and you wanted to stop “working late”?

Would she still tell you how well you are working and treat you the same?
It is best if you end the fun now.

Tell your boss it has been great but you respect her too much and don’t want to risk the job you love.

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