There are many myths about relationships with trans women but they are, for a man, little different from those with cis women. Obviously, in the case of an intact trans woman there is her penis to deal with, but this amounts to something around 1% of her; the other 99% is more important.
There are subtle nuances of difference but no more than one might encounter if in a relationship with someone from a different cultural background.
I think the most damaging of the myths, regarding transwomen who retain their genitalia, is that they will want to use it in the way that a man would. Outside of sex work, this is rare; most just won’t. (I do know some who do, for pleasure and in private but they are unusual, likely well under 10%.)
Amongst others, who maintain their penises, some are very strict that it is a no-go area. These will generally seek GRS at some time. Others are more fluid; they enjoy the physical pleasures but will not indulge in activities they consider masculine, meaning, penetration.
Everyone is different and this has an awful lot to do with trust. Trans women are often very concerned that the man they are dating might be gay, and most will see a desire to be penetrated as indicative of that. All the trans women I know have loads of gay friends and they won’t go near them sexually.
I know of one girl who specifically had her GRS, quite late on, because her long-term partner kept asking to be penetrated. She loved him but performing this act made her feel that he was actually gay and she was not prepared to be in such a relationship. In order to settle the matter, she made the option impossible. The relationship did not survive.
One of the other huge myths and perhaps the most damaging, is that the relationship between a man and a transwoman is gay: it isn’t. It is a normal one between a man and a woman and thus stands outside the LGB spectrum. Whether you choose to call it heterosexual is up to you; I would consider it to be.
The term ‘homosexual’ was coined in the 19th century. In the West, male homosexuality is defined as a desire for other males. However, in most of the world and certainly for thousands of years, the definition is by practice: one who desires to be penetrated. To put that another way, a man with female sexuality is homosexual. This is called Sexual Inversion.
Having a sexuality which is not aligned to sex, like this, is called Sexual Inversion. It turns the male into a woman, no matter how that person presents in terms of gender. Inverted males in such cultures see themselves as ‘women inside’; and since only men can penetrate, they are by definition attracted to men. But understand that it is not so much the gender identity they are attracted to but the sexual role such a relationship affords: it allows them to play the woman’s role in sex.
Gender is the set of signals, both innate and therefore evolved, and culturally conditioned, that advertise a person’s sexuality to others. Why do women have breasts and large buttocks and men body hair, beards and deep voices? These are not functional qualities, they have evolved as visual signals that identify us as male or female. We build on these through cultural norms.
In the West this view is considered ‘old fashioned’ notably by some USicans; but that is another of the myths. It is perhaps appropriate to remind USicans that they are 3% of world population, and they don’t get to say how things are for the rest of the world, either through their propensity for violence or domination of media.
So when a man penetrates a trans woman, it is a heterosexual act and would be, even if she were presenting as a man, because of the sexual roles they are playing. this is because in penetrative sex, the penetrator is always male and the penetrated is female.
The above leads to a gender inversion taking place when a trans woman penetrates a man, because she has to become a man to do it, and he a woman. An excellent, well researched and sensitive description of this phenomenon can be found in Prof Don Kulick’s ground-breaking work Travesti. In this case, the act is still heterosexual but the gender roles are reversed.
However, it is unusual to meet trans women who will do this outside of sex work, so it isn’t really a normal part of trans woman – cis man relationships in general.
.It’s worth mentioning that Autogynephilic transvestites, through the act of being penetrated by men, become women too and could claim the status of ‘Pseudo-transsexual.’
Another of the popular myths concerns the ‘tranny chaser’ a pejorative for men who are attracted to transwomen, invented apparently by AGP transvestites and often used by feminists. HSTS, who present as such, ie are not invisible and living and relating as women, are almost always delighted to meet a straight man who likes transwomen. The last thing they would say to insult him is that he is a ‘chaser’ though they might, in extremis, call him ‘gay’ or pejoratives of that meaning, especially if the man has abused them.
This is a confirmation of Blanchard’s profiling: HSTS women relate to men exactly as women do. They are not generally perturbed to know that a man has had relations with other HSTS, any more than women are by a man having had former girlfriends. (They might be if the man were revealed to have been with other men, however.)
On the other hand, some AGPs relate to men as a part of their sexualised construction of a female self. In other words, men are sexual props who prove the AGP’s femininity. In the West, however, most are both gynephilic and androphobic, that is to say they are attracted to women and repulsed by men. Only about 20% in the West are androphilic, though this may be changing as AGPs begin hormones at younger ages, before their male sexuality has crystallised. These are known as ‘pseudo-bisexual’ because they always retain their initial desire for women, though it is now compliment by a desire for men.
For the majority of AGPs in the West, however, who remain exclusively gynephilic, their androphobia may cause an extreme reaction to advances from men.