Answered on Quora:
I am going to go against the PC line that transwomen are women. I say they are not women. Instead they are men who think they are women. No amount of surgery can make a man a woman.
However, this is an interesting question. There was a fully transitioned transsexual named Lana a while back who made a lot of porn. The porn is straight porn, and the men having sex with her are regular straight men. She looks very much like a woman although she has a pretty strange looking vagina. In fact, she makes a very beautiful woman.
I have no idea what sort of men date fully transitioned transwomen. It’s a mystery to me.
However, there are quite a few straight men who will date and have sex with pre-op transwomen. That is, they still have a penis. These men only play the male role with these pre-ops. The two men I knew like this were extremely masculine and were both serious womanizers. And one man was very homophobic. But as you can see, even a homophobic man might have sex with a pre-op transwoman!
I like to go look at forums of people who odd or bizarre sex fetishes. I am not into any of these fetishes, but I am fascinated by sexual strangeness.
There was a forum for men who were in Thailand who had a fetish for ladyboys. Most of these ladyboys were pre-op transwomen. The men were generally White men from the West.
I was fascinated to see where these men were at sexually because the fetish seemed so odd. Now these men were unusual because most of them played all roles with these ladyboys. For instance, most of them liked receptive anal sex with their ladyboys. Practicing receptive anal sex is quite gay behavior. Many bisexual men who lean more straight will refuse to do this, as it means you are playing the female role in gay sex, and these men often only play the male role.
As I studied them further, it became clear that none of these men were gay or even bisexual! That is, none of them had sex with ordinary men. I am not sure if they had sex with women either. Also they came across very straight in their conservation and photos, and many seemed like masculine straight men except for the fetish (gay men and straight men often talk in very different ways, and I can often tell them apart).
A ladyboy looks and acts like a woman, except in this case, it still has a penis. The man who is attracted to a ladyboy would be a man who is attracted to women.
My conclusion was that these were some odd type of heterosexual men who were attracted to women or people who appear to be women but who had some strange fetish for ladyboys which even extended to getting fucked in the ass by the ladyboy. I did not think they were gay at all or even bisexual.
I admit it’s an odd fetish!
Answered on Quora: