The Sex My New Boyfriend Just Admitted He Had in His 20s Feels Like a Huge Red Flag

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The Sex My New Boyfriend Just Admitted He Had in His 20s Feels Like a Huge Red Flag
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Dear How to Do It: I admire his honesty. I’m worried I can’t be with a man like this.

You should know my bias before we proceed. We have opposing first principles. You see patronization of sex workers as something to “get over” and question whether it’s an “extreme red flag.” I have been a sex worker for over 15 years, mostly as a performer in pornographic videos, but I’ve also done physical contact work such as professional domination, professional submission, and lap dances. So that’s me.

Your boyfriend saw escorts for 10 years and has a much higher sex drive than you do. To me, these two facts together look like a perfect match—the two of you can have sex when you’re interested in engaging, and he can get his other desires met through channels. Something tells me this structure wouldn’t be comfortable for you at this time, though.

As for what to ask him, I suspect you’ll have plenty of questions once you’re coming from a stance of curiosity. Details, like how often, are great starting points. So are broad questions like “Is it different from recreational sex?” Start a real conversation and ask the questions that you want to know the answers to.

Background: Between an STD scare and fertility treatments, my husband and I both agree that for the time being we want to close our relationship for an indeterminate but not permanent period of time. We both have other partners on the level of friends with benefits and he has a casual girlfriend, with whom he spends maybe one night a week.

Neither my spouse nor I are looking to end our friendships nor his relationship, but we both think for now, it needs to close sexually. How do we have this awkward conversation best?It is awkward! Telling someone that we need to stop doing something we both enjoy is hard. And your other partners may feel a sense of loss. You might, too.I think your husband and his girlfriend should be the first talk—she’s the most significant relationship, and she should find out first.

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