Pls Help! “My boyfriend thinks I am naive, he doesn’t know I was once a prostitute”

Never judge a book by the cover, that is all that got to my mind when I read through this story. 

A woman who hides a deep secret from her partner feels sorry for him each time he calls her naive and clueless because he thinks she is innocent.

Read below:

He’s always telling me that I’m naive and clueless. But I harbour several deep and dark secrets.

For a start he has no idea that I used to be a sex worker, that I lived off a sugar daddy for years, and that I used to be male.

I was born abroad and declared a boy at birth, but the diagnosis was wrong.

I returned to Britain and had a number of reassignment operations as a youngster to restore me to my true sex.

As a teenager I went off the rails. I ran away from home and got in with a brothel keeper who looked after me. At first I worked on reception, but then I started turning tricks.

I earned some good money too. One day a rich guy walked in and I walked right out with him on my arm. For many years my sugar daddy kept me safe and warm.

Our relationship tragically ended when he died of a heart attack (on the job) and his family refused to recognise me as his heir.

I didn’t have the cash to fight them and met my current boyfriend in a bar. He thinks I’m super sweet. Naturally, I play up to this image he’s created for me, because it gets me stuff (clothes, perfume, jewellery) and makes him adore me more.

But if I were to show him some of the tricks I can do, then he’d have kittens. I’m not ashamed of who I am and what I like, but fear that I’ll frighten him away if I tell him the truth.

My other concern is that some spiteful person might nip in before me and tell him all about my frisky past before I get a chance to hit him with the cleaned up /need to know version.

I really do like this guy and don’t want to screw this one up. How must I play this?