Hyperlinks:

Crucial Resources, "What Does That Make Me?" Myths, Cardinal Rules of Dating, Dating Sites

Admirers are sometimes controversial in the transgender community, sometimes referred to as "tranny chasers." They can deserve a place in the community, but that is provided that they:

• Make an effort to comprehensively understand transsexual and other transgender people (and overcome assumptions, i.e. porn cliches or the "so, you're like really a guy, right?" misunderstandings),
• Leave support group spaces alone (unless accompanying a date / partner), as those are not dating spaces, and
• Have more interest in a transwoman or transman than just some kinky sexual experience they'd like to try.

The key is respect, which goes both ways: some admirers have difficulty respecting transwomen and transmen as individuals, and some transwomen / transmen have difficulty respecting admirers because of past bad encounters.

A Few Crucial Resources

Renee Reyes has some excellent advice, as does TSGirlfriend. These resources are primarily for admirers of transwomen (incidentally, "shemale" is an invention of the porn industry, and not everyone likes that term -- just one example of why it is important to read these resources and know the etiquette... and then, if you're uncertain, ask your date what she is comfortable with). Admirers of transmen do exist, but there are fewer resources for them. We sometimes assume trans admirers to be looking for MTF persons for the same reason, but in most cases, there is an FTM corollary.

"If I Like Transsexuals, What Does That Make Me?"

Male trans admirers are often confronted with their own sense of homophobia with regards to themselves, either afraid of possibly being gay or ashamed of being somewhat transgressive.  I tend to think of orientation as a continuum too, with homosexuality and heterosexuality at opposite ends, and very few people actually being strictly one or the other.  A person could be attracted to women 95% of the time, for example, but still encounter the occasional exception where they might be curious about a relationship or encounter with a man.  Transwomen cloud this a little, usually being predominantly feminine, and many admirers are still closer toward the “straight” side of the spectrum in terms of what attracts them.

But much of the fear of being gay is also driven by a social construct.  Society teaches men that it’s unnatural / sinful to be gay, and sometimes does a pretty loud song-and-dance about it.  But 200 years ago, social convention also taught that black people had no souls.  One hundred years ago, society contended that women were not intelligent enough to vote responsibly (and even now, some extreme religious spheres push the idea that women should be subservient and forego careers to function primarily as baby-making machines and nursemaids).  Society has touted a lot of bullshit in the past, and it’s entirely reasonable to question the attitudes that we are fed.  Religion can sometimes be a more difficult issue to deal with, but there are GLBT-affirming churches fairly widely accessible, and other resources that can help understand and resolve spiritual issues.  And often, the best approach is to listen to what your heart tells you, even if you’re afraid of what you might find.  The heart is usually pretty honest.  Hopefully, though, those who come to consider themselves not gay will still have learned to respect those who are.

It occasionally happens – perhaps among five percent of admirers – that the transfan is also trans-identified, or questioning his (or her) own gender identity.  These admirers are often looking for answers, or wishing to live vicariously through their partner, sometimes doing so until they come to a point where they are comfortable with the idea of transitioning themselves.  Openness and honesty are far better policies.  Sometimes with transfolk, trying to go through a transition when a partner is embarking on a similar (or opposite) transition presses a lot of hot-buttons of insecurity, so just because she’s trans doesn’t mean that she’s compatible or ready to live your transition at the same time as hers.

Myths

Unlike what is depicted in porn, transwomen are usually not "sex machines." Hormone-replacement therapy usually significantly reduces the libido and physical capabilities, as well as affecting changes in behavioural experience. An admirer should never assume that a transwoman is just looking for a sexual experience (some do, but it's better to watch for a clear invitation, or else expect it to be otherwise). For some, being someone's personal "experiment" will leave them feeling like little more than some used novelty sex toy. Most transwomen are looking for more relationship than that. If you're mostly looking to experiment, it's usually better to stick to girls who are escorting or frequent contact sites or clubs and say they are looking for a good time. Be honest with them. There are enough of us out there that you'll probably find the girl you're looking for and who is looking for the same thing sooner or later, as long as you're patient. Some girls may also be uncomfortable with different kinds of play -- part of being transsexual has to do with discomfort with one's body and parts attached that seem like they shouldn't be there.

Admirers should never assume that transwomen are looking for male partners.  A person’s gender identity does not dictate their sexual orientation, and many transwomen prefer females.  The ratio of androphile (liking men) to gynophile (liking women) transsexuals might possibly be a 50 / 50  split not taking into account bisexuals, as transwomen may be), but when crossdressers are factored into the equation, the percentage of those who are lesbian goes much higher.

Cardinal Rules of Dating

1. She needs to be treated with respect.  This includes respecting her as the gender to which she identifies, and maintaining the correct pronouns.  Refusing to do so or throwing inappropriate pronouns around in an argument often constitutes a deal-breaker.
2. Don’t make assumptions about her sexually or in terms of lifestyle and future plans.  Be clear about what you’re looking for, and if she’s looking for something very different, trying to press forward into a relationship is going to make one or both of you very unhappy.
3. Transwomen usually want the same things that women want – things like longer-term relationships, kindness, manners, courtesy, good humour, interesting conversation and similar interests.
   
4. Transwomen usually live in “stealth,” meaning that they don’t really want the world to know that they’re transgender.  They are usually sensitive about having anything “out” them publicly (including loud conversation in public places), and would also rather be asked before you tell your friends.

The Internet is still the most common place to make contact, because transpeople tend to blend in and try to be relatively unrecognizable in everyday life. Approaching a girl out of the blue and asking if she's trans can make her feel awful for this reason. Most transsexual women really don't want to be thought of as anything other than women, and recent genetic and brain structure studies really do support the longstanding belief that transwomen are psychologically female, they were just given the male naughty bits. A common serious mistake that trans admirers make is to treat her and act toward her like she's "really a guy."

Gay bars will sometimes be fine as well, but keep in mind that a wider variety of transgender person will be in attendance, and it may be harder to locate the kind of person you're interested in. There's a lot of diversity in the transgender community, and there can be a large difference between transsexuals (psychologically female, transitioning or transitioned), crossdressers (part time) and transvestites (people still questioning and usually only comfortable enough to pursue some sexual fantasy -- for most transgender people, it's not about sex). People can be a little sensitive about terminology for this reason.

It's considered impolite to ask a girl if she's had her surgery, but it's also something that guys tend to want to know -- chances are, if she's been living as female for many years, she probably has had her surgery. If she's in transition or has been living as female for under 2 years, she's more likely to be pre-op (it's not always a perfect way to determine that, but it helps).

Dating Sites

Some places online to try are TS Girlfriend, Alt.com (it looks like a BDSM site but isn't just specific to that), Craig'sList, URNotAlone, and CollarMe.com (which is a BDSM site, but with some transwomen also) have a few contact options. Trannyweb has some contact features, but I don't know how they are or if they are visited often. Social networks like Facebook are becoming popular areas as well. Some of these sites have female-to-male transsexuals mixed in with male-to-female, so be prepared for that. And if you're using a site that has a profile that tells you a little about her first -- be sure to read that: nothing is more frustrating than having posted personal information in advance, and then be contacted by people who demonstrate that they have not been interested enough to read and note that. These sites are global, of course, so finding someone in your area might take a little time and patience -- they do show up from time to time. If you prefer to try meeting someone during clubbing, Twisted Element (1006 11 Avenue SW) is the place to go in Calgary and PLAY (10220 103 Street) and Buddy's (11725B Jasper Avenue) are the places to try in Edmonton. These are gay bars, so you will have to be reasonably comfortable about that. Again, it's probably best not to just ask someone if she's trans, just try to watch for physical signs and then get to know her first.