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As a straight guy I'm a bit unsure of how to do my ad copy.
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To be perfectly honest with you, gay ad copy is not much different [in the basics] than straight ad copy.
For the most part, you can change the gender specifics and get some good text, this is always the best method that i recommend to those webmasters wanting to start out in the gay market so far as promotional text goes.
Another really good method to get some decent gay ad copy is to take a look at some of the larger gay programs sites as well as see what other webmasters are using on link lists such as
http://www.gaylinxxx.com or on tgps such as
http://www.cumsoda.com that will at least give you an idea on which to base your own marketing on.
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He likes 'bears'. I sorta have an understanding of bears, twinks and cubs....but if I'm promoting a site with muscular, bigger guys do I presume my target audience to be 'bottoms'?
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Not necessarily (sp?) as with the straight market, gay men can take a range of roles as with the women and men in straight. For example, just because a woman is blonde, does that mean she is automatically a 'top' or likes sex 'doggy style' ?
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If it's a twink site then it's marketed towards 'tops' and they'd be doing the fuckin' and tend to be the more dominant in general.
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Again see my reply above, so far as sexual preferences, there is no 'stereotype' when it comes to a specific type of model.
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Guess I'll look at ad copy on the paysites to get a feel for it.
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That is also a great place to start getting a feel for gay marketing text just be cautious of the sites you use as a reference point is all i would say.
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Er...I dunno if I can look at naked dudes though.
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So dont, just look at the marketing text
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Maybe I'll start with shemales and work my way to gay. 
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For the most part, 'shemales' are considered a straight niche, whilst the GLBT community stands side-by-side with transgendered individuals when it comes to what gay men and women like compared to transgendered people, there is a difference. In fact, most customers for tranny sites are actually middle-aged straight men (think of your typical wall-street banker types).
If you need any more help feel free to contact me by email
lee@gaywidewebmasters.com or head across to the domain in my emai address and you'll find a wide range of individuals currently working the gay market who will be more than happy to help you out, irrespective of whether you are gay, straight, black, white or martian
Hope this post has helped you somewhat
Regards,
Lee