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Let me break it down, homie...
Transvestites, also called cross-dressers, are transvestic fetishists. This simply means that they achieve sexual arousal and satisfaction by dressing as a member of the opposite sex. The vast majority of transvestites are heterosexual, and so cross dressing is not ordinarily an indicator of homosexuality, and so one could argue that most transvestites are biologically men, and psychologically men, but have a sexual fascination with "the woman inside."
By these definitions, tranvestism is a paraphilia... a persistent sexual behavior in which unusual objects, rituals, or situations are required for _full_ sexual satisfaction. Voyeurism is a paraphilia, shoes or panties fetish is a paraphilia, latex/rubber fetish is a paraphilia.
Transsexualism, on the other hand, is a gender identity disorder, meaning that a transsexual's personal sense of "man-ness" or "female-ness" is different from their traditional gender role as bestowed upon them by their biological make up. This is a fancy way of saying "a woman trapped in a man's body", and vice versa. Since they feel a strong and persistent urge to be the opposite sex (cross-gender identification) and they feel extreme discomfort and anxiety as their biological gender (gender dysphoria), they opt to undergo complicated and expensive therapies and procedures to have their gender switched/reassigned.
Since we're focusing on dickgirls for the purposes of this post, I'll focus on them. There are two kinds of male-to-female transsexuals: homosexual and autogynephilic. Homosexual transsexuals can be thought of as extremely feminine gay men who wish to change their sex. On the other hand, autogynephilic transsexuals have a paraphilia where they're attracted to the image of themselves as a woman (which is similar to cross-dressers) and they can be attracted to men, women, both, or neither.
As far as terminology is concerned, surfers are generally looking for the same thing when searching for tranny or shemale. However, there is a fine distinction between the two that may or may not play a role in which sites/models you promote for each keyword. Tranny seems to be a derogatory catch-all term for women who used to be men, and so this can include transsexuals who have already had gender re-assignment surgery. Pre and post-ops. Shemale though usually denotes a man with all the characteristics of woman, but still has a cock. Pre-op.
Ladyboys are a bit trickier. The term ladyboy refers to "kathoeys", which is a Thai term meaning male to female transsexual or highly effeminate gay male. So, when you've got ladyboys/kathoeys, you can either have a man who is currently undergoing or has already had gender re-assignment therapies and procedures, OR a very dainty, womanly male. However, ladyboys/kathoeys can be seen as distinct from "trannys" and "shemales" for marketing purposes as their label denotes their Asian heritage.
It's quite late here and hopefully my presentation is enlightening, lucid, and without too many spelling and grammar errors because that would be wiggity wiggity whack, yo.
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