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I cheated on my fiancée with a prostitute at a stag party – the guilt is keeping me awake

DEAR DEIDRE: FRIENDS always teased me because I’d only ever had one partner – so I cheated on my fiancée with a prostitute.

Now the guilt is keeping me awake at night and I think I should tell her.

I’m 27, my wife-to-be is 28, and we’ve been together for eight years since we met at university.

I was a virgin before that. I’ve always been shy and she was my first (and only) proper relationship.

She had a couple of other boyfriends before me, so she’s more experienced.

I really love her and know she’s the woman I want to spend the rest of my life with. That’s why I asked her to marry me last summer.

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But I often wondered what it would be like to have sex with someone else and worried I’d missed out.

Over the years, my mates have ribbed me non-stop about my lack of experience.

They have said things like the relationship won’t last and, if it does, how sad that I’ll only ever have sex with one girl.

A couple of weeks ago, I went to a friend’s stag do — a weekend in Amsterdam.

We all got drunk and a few of us ended up in the red light district.

The others dared me to have sex with a prostitute.


Stupidly, I agreed — mainly to save face.

I hated every minute of it.

I felt like I was using the girl and the sex was mechanical and unexciting.

Afterwards, I went back to my hotel room and threw up.

Since then, I’ve been overwhelmed with guilt.

My fiancee knows that something is wrong.

I feel like I should tell her so that I can get over this terrible guilt.

We’ve always been completely honest with each other and I don’t know how I can marry her knowing I’ll be living a lie for the rest of my life.

But I worry she’ll dump me if I tell her the truth.

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DEIDRE SAYS: Telling your fiancée what you did might make you feel better for a few seconds, but it will hurt her deeply and almost certainly destroy your otherwise happy relationship.

Assuming you had safe sex – and it might be wise to get yourself checked out at a sexual health clinic – she’s better off not knowing.

Instead, learn from your mistake, which it sounds like you’ll never repeat.

You now know that experience for its own sake has no value.

Unburden your guilt by talking to a counsellor in confidence.

See my support pack Counselling for more about the benefits of this and how to arrange it.

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