11 Tips for Dating a Transgender Woman

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11 Top Tips for Dating a Transgender Woman

1. Don’t call her a “tranny” or a “shemale.” If you refer to her as a tranny instead of a woman, she’s going to think that you don’t take her seriously and that you don’t regard her as a woman. She regards herself as a woman and you should, too. The second term came from the porn biz. The vast majority of transsexuals will find it very insulting if you describe them using a term from the porn biz.

2. TS women are constantly being hit on for sex, as though they are sex toys and they resent it. Anecdotal evidence says they get this much more often than do genetic girls (GGs). If you’ve been behaving that way, stop for a moment and think. Would you hit on a GG the same way? She did not transition in order to provide you with a perpetual hard-on. Treat her with the same respect that you would treat a GG.

3. Surprise your TS friend on your first date. Treat her like a lady. Courteously open the car door for her. Let her order first in the restaurant. Do not even bring up the subject of her transsexuality during the course of the date. Why not? Because she fully expects you to bring it up. Startle the lady. Don’t mention it at all. Save it for some other time. Doing this immediately puts you in a class above all the other guys (drooling horndogs?) hitting on her.

4. If you ask her, “So why did you decide to become a woman?” you’re unclear on the concept. In her mind, she’s always been a woman. Transitioning is a process to make the body match what’s been in her mind all along. This is not a lifestyle choice any more than a gay guy “decides” to be gay — because he’s always been gay. When she was living as a male, she was pretending to be a male. Back then, she may have looked like a guy, may have behaved like a guy…but she never really was a guy. It was roleplay.

5. Understand that most men interested in transsexuals are specifically seeking pre-ops, those with a cock. They are under the impression a pre-op TS will be cool with bisexual guys messing with their dick. Although there are exceptions to this, the fact is well over 90% of pre-op TSs undergoing hormone replacement therapy (HRT) wish to be viewed as women, not as women with dicks. On average, they are not interested in bisexual men. They want to be appreciated for their own feminine qualities, their character, their brains, empathy, creativity, etc. They do not wish to be appreciated because of that male appendage, which most TSs regard as some yucky, weird, foreign thing they are unfortunately stuck with until such time as they can convert it into a vagina. The exceptions to this rule will include those who make a living out of being pre-op, such as adult video performers and escorts.

6. Don’t expect her to “top” you. With few exceptions, transsexual woman do not want to fuck you. They want you to fuck them. Women want to be “taken.” Don’t believe me? Go check out the covers of romance novels. Look into a woman’s eyes…notice how those eyes draw you in? When was the last time a GG, on her own initiative, donned a strap-on dildo and screwed you with it? Think about it.

7. Don’t introduce her to your friends and family as a “transsexual.” Introduce her as your friend, lady friend or girlfriend by her name only. If you’re a white guy and you have a black girlfriend, would you introduce her to people as “my black girlfriend”? Didn’t think so. Besides which, the fact that she’s TS is nobody else’s business anyway.

8. Be aware that her old friends, family and employment could be very sensitive and emotional subjects for discussion. Transsexuals often endure rejection by former friends. Many times, their siblings and parents cut them off from all communication or refuse to accept them as women. The same occurs with former spouses and children. Many have endured economic hardship because of job loss associated with transitioning, and many find it very difficult to find work as a woman.

9. Don’t think for a moment think that because she has or had a dick that she’s going to be your “buddy.” She won’t be any more your buddy than any other woman will. Most women don’t do the guy-buddy thing well at all, for exactly the same reason that you don’t do the best-girlfriend thing for her.

10. HRT will turn her into a person who is fully feminine in how she views the world, views you, and behaves. In at least some cases, her memories as a male will fade, or will at least be filtered through the hormonal process. Those memories will be viewed as though she had been female all along. She may well lose all sense of what it felt like to be male. That’s precisely what happened with my (former) transsexual girlfriend of seven years standing.

11. Show her that you appreciate her femininity. It’s no secret that GGs love to be told how lovely they look, and that they love gestures of affection. This need is compounded when a woman is TS. She has more than her share of insecurities to deal with about her mannerisms, appearance, physical build, voice and numerous other things. Remember, she was raised as a male and changed genders long after GGs have learned how to be women. If you think she looks lovely today, you will go a long way toward alleviating those anxieties by telling her so, giving her a great kiss and bringing her something pretty to reinforce her sense of femininity, such as flowers.

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