Is it permissible for a man to marry a transgender woman?

Question

Can you marry a transgender woman or a woman with a male reproductive organ and if so does anal sex become permissible?

Answer 1

To start:

1. homosexuality is considered haram in Islam.
2. homosexual acts including anal intercourse are also considered as haram in Islam by a vast majority of scholars. In fact ahadith ordering punishment for such acts actually confirm this view as they neither differ if both people involved are of the same or different gender.
3. in Islam only marriage of partners from different genders is regarded as legal, as long as the gender can be distinguished.

In Islam there's a difference between hermaphrodites الخنثى (Khunta) depending on their attributes:

The word khuntha (translated here as “intersex”) applies to a person who cannot be easily characterized as male or female, or the one who has both male and female anatomy. The word is derived from a root referring to softness, gentleness and tenderness. In shar‘i terminology it refers to one who has the anatomy of both male and female, or one who has neither, and has a hole through which he urinates.
(Source Islamqa fatwa #116740)

the linked fatwa also addresses the topic of the effeminate which basically is a person who is male, but acts and or speaks like a female.

• There's an ambiguous hermaphrodite this is basically a person on whether one couldn't distinguish or clarify is he/she rather male or female in his/her attributes (sexual attributes, such as reproduction in first place). Marrying this type of hermaphrodite is not regarded as allowed nor valid in Islam as you don't know whether you've married a man or woman:

The ambiguous intersex individual is one who shows no clear indications of being either male or female, and does not know whether he is a man or a woman, or he has characteristics of both genders.
This ambiguity is of two types: one that has the anatomy of both genders, where other defining characteristics are present in equal measure, and one who does not have the anatomy of either; rather he has a hole (through which he urinates). (Same source as above)

• And unambiguous hermaphrodite this is basically a person where these attributes become clear and can be distinguished, so that this person could be regarded as more male or more female even if he/she has both sexual organs!

The unambiguous intersex individual is one who shows clear indications of being either male or female, so it is known that this person is a man or a woman. There is no ambiguity involved here; rather this is a man who has something extra that was created in him, or a woman who has something extra that was created in her. With regard to matters of inheritance and other shar‘i rulings, such an individual is treated in accordance with what he or she appears to be. (Same source as above)

So let's assume one wants to marry a hermaphrodite: If this person got her menses and used to pee from her female organ she would be regarded as a woman even if she has a male organ. And in this case a Muslim man can marry her.

See also:
Fatwa's -in Arabic- islamweb #380261 and #131276.
And islamweb -English- Fatwa #413731.