I went on dates with a gorgeous sex worker – could we have a future together?

DEAR DEIDRE: A GORGEOUS sex worker has got under my skin – and as restrictions relax I’m torn over what our next steps should be.

Before the last lockdown, we went on a few dates and got on brilliantly. We even spoke about dating properly but I don’t know how we would explain things to our families.


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I am a single guy of 47 and I have three children. I have been divorced for ten years and have brought up my kids — aged 18, 16 and 13 — alone.

I am really proud of them and as I no longer need babysitters, saw nothing wrong with visiting a brothel. I met this woman through the massage parlour I’d been visiting for a couple of years.

One day when I visited, my usual woman wasn’t there. I am very attracted to my regular masseuse but this woman was on another level. She gave a full body massage then undressed to reveal the most incredible body.

She is 35, really curvy and we had the most exciting sex I’d ever had. While getting dressed afterwards, she asked for my number. That surprised me a bit but I handed it over. The next day she texted and asked to meet for a drink.

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She told me she was a single mum of a ten-year-old and she thought I was lovely. I told her she was great too. We didn’t have sex that night, just a great time getting to know one another. We met the following week as well.

Until the recent lockdown we saw each other at least once a week outside of her work.

When lockdown was introduced, I told her I wouldn’t visit the massage parlour and felt we should put everything on hold. She agreed but she is now asking to meet again.

But I’m worried it would be too awkward in the long run.

DEIDRE SAYS: Most sex workers do not choose this path and there is no denying it’s an exploitative business.

It’s a means to an end. This woman may have had a connection with you but a couple of dates doesn’t mean you could have a rosy future together.

You both need an honest discussion addressing what you are looking for and what your red lines are and then look at whether you could make it work.

Visiting sex workers would have felt safe after your divorce and the stress of bringing up your children on your own. You are now testing the water with regards to starting a relationship.

If you decide your sex worker isn’t right for you, my support pack Finding The Love Of Your Life will help you to connect with somebody who is looking for the same sort of relationship as you.

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