Those who are new to transgendered and transsexual women face a bewildering assortment of terminology as well as some fundamental misinformation and transphobia that is entrenched in the larger society. With that in mind, we’d like to get you up to speed with some generalities about the trans community as well as the ladies themselves, though as with anything written about human beings, every trans woman is an individual so what is true for most is not universally applicable.
Trans women really don’t have any desire to “top” the men they are with. While transgendered women were born with penises, they have more often than not wrestled with that unwanted dangling appendage for most of their lives, and many just wish it would be gone, or are on the long journey to transition to a more fully realized female form. Having them penetrate you (if they are even capable of doing so), is pretty much off the table for most transsexual women. If your fantasies revolve around playing with a transgendered woman’s penis or having her fuck you, first off you will find that stating so will make most of them head for the hills, trans women are not men and want nothing to do with their penises, much less wielding it like a man would. If your interest in transgendered women revolves around having her dominate you with her penis, you would be advised to find a gay drag queen or a she-male sex worker to satisfy those urges. Most transsexuals want nothing to do with a “penis chaser.”
Do not use the words tranny, trannie, she-male or chicks with dicks when referring to transsexuals or transgender women, not even in jest. It’s the trans-equivalent to the “N-Word” for those of African decent or any other racist or sexist epithet, and hurting her feelings is not the way you’re going to make a new friend. Always use the proper pronouns when referring to a trans woman, like “she” and “her,” regardless of whether she has a penis or not, and regardless of whether she looks convincingly female or not. I it’s a show of respecting her right to self-determination.
It is considered bad form to ask a transsexual woman if she is pre-op or post-op, many transsexual woman have no plans to have their male genitalia changed, and the treatments for gender reassignment are significantly more involved than simply lopping off of her penis making the pre/post-op differentiator overly simplistic. In any case, it is considered more polite to refer to the modification of one’s natural born physical sex as a process of “transitioning” as it is a long process that is different for each individual. For some it may be simply living and dressing as a woman with no medical intervention whatsoever, for others it will involve hormones, electrolysis and extensive surgeries to remake themselves into a more female-appearing form.
Be careful about well-meaning compliments that can be hurtful. Saying something along the lines of “you look like a real woman” or “you could pass for a real woman” while not intended to inflict harm, carry the implicit underlying thought that she is not legitimately a woman. Given the struggles and severe emotional distress most trans women have gone through in their journey of self-actualization, they are quite sensitive to statements that imply that they are not genuinely female. In reality, they are so genuinely female that they were willing to fight society and take on all the risks and potential attendant miseries associated with being trans in our society, just to be the girl that they really are inside.
Do not critique her appearance. Just as this advice would serve you well with a cisgender female, you would never tell her she looks fat or ugly, the same thing goes for trans women, and this particularly includes calling attention to any traits or appearances that you deem “male.” Chances are good that she owns a mirror, and with the possible exception of telling her that she has a piece of spinach stuck in her teeth, your comments on her appearance should be kept positive and in keeping with her being female.
While as a man the notion of someone cutting off your penis probably elicits a visceral “Oh my god, no no no!” response, for a woman who had the misfortune to be born in a male body, that dangling bit of unneeded and unwanted flesh is a source of aggravation and/or shame, not something they want played with or something they particularly want to talk about. Statements like “You’re so brave, I could never have my junk cut off,” while well meant, are not promising topics when conversing with a trans woman, and the very basis for the statement demonstrates a lack of understanding.
As women who have fought long and hard to become who they are, trans women always have their radar up for signs that they are being treated disrespectfully, or not in keeping with their gender. This is not to say that they are overly sensitive bitches, but through their struggles, which surely have included people being unkind, as well as self-inflicted psychological trauma, leaves many trans women sensitive to perceiving disrespect in others. Chivalry and respect will go a long way to winning her over, perhaps more so because of previous negative experiences.