I feel ready to explore my fantasy of having sex with a transgender woman

DEAR DEIDRE: I HAVE always considered myself straight but I feel ready to explore my fantasy of having sex with a transgender woman.

I’m a man aged 28 and I’ve had two long-term girlfriends, although I’m up for trying something new.


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For ten years I’ve been fascinated with male-to-female transsexuals.

Now I’ve taken the leap and have joined a transgender dating website.

A friend of mine told me about a holiday he had where he had sex with a transsexual woman in Bali.

He says he didn’t actually know this partner was born male until they got into bed — and the sex was off the scale.

I’ve never been to bed with a man before. The appeal is not in what their body might be like.

It’s that somebody born male would know what a man likes when it comes to sex, so I don’t care whether they are part-way through their transition or now a full woman.

My parents are Christian and they would be horrified. I had such a strict upbringing.

They don’t even believe in sex before marriage, but I feel that this is a part of my sexuality that I need to explore.

I had a trip planned to Thailand so that I could hook up with a sex worker to try it out.

But then the pandemic hit and my holiday was cancelled.

I feel a bit in limbo right now. I don’t want to date another non-trans woman because I’ve been longing to have sex with somebody transgender.

If I can’t meet somebody to go on a regular date, do you think that arranging to go with a transgender sex worker here would be a safe thing to do?

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Buying sex through a sex worker is one thing but if you use transgender dating websites to meet somebody for casual sex and the other person is looking for a relationship, then you’re not being fair.

Relationships are all about respect and if you don’t respect the person you’re about to bed, then don’t do it.

Fantasies are often better in your head so explore this carefully before making it a reality or you risk feeling unfulfilled.

Explore why transgender people have this draw for you and how you will build a future with someone who is transgender and integrate them into your devout family.

You’ll get a better understanding about yourself by talking with a counsellor from the College of Sexual and Relationship Therapists (cosrt.org.uk, 020 8106 9635)

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