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Dealing with ingrained homophobia, stereotypes, etc. at work

I had a situation come up at work the other day, and the more I think about it, the less certain if the way I handled it was appropriate, or if I missed an 'educational opportunity'–for myself and/or for the other parties involved. 

I take calls on the helpdesk for a printing company.  During a slow time, I was sharing pictures of my sister's prospective wedding dress to some of my co-workers. (She's getting married next year.)  One of my co-workers made a comment to the effect of “She went wedding dress shopping and didn't take her gay brother along?” (NM that it was logistically impossible.)  One of my other co-workers heard the remark and was slightly offended because of the 'politically incorrect' stereotyping.  At the time, I laughed it off as a joke, and thought nothing more.  Later I found out that my offended co-worker had said something to my boss, and my boss asked me about it.  I explained that I wasn't bothered by it and took it as a joke.

The co-worker who made the questionable comment and I get along pretty well, although he does rub some of my other co-workers the wrong way.  I don't shout “I'M GAY” from the roofops, but I don't really make secrets about being gay at work.  He and I had a conversation shortly after he started working there because I registered on his 'gaydar.'  The gist of the conversation was “You're gay right?  I'm straight but not narrow. You're not my type and I'm not yours.” (Sometimes it seems to border on protesting too much, but the guy tends to be a bit arrogant and brash anyway so it's difficult to tell if it's machismo or homophobia.)

The offended coworker asked me about the comment when we had a quiet, semi-private moment, and thought I was being 'too nice' to the other guy and I cut him more slack than I should have.  (Note the offended co-worker is one of the ones who is rubbed wrong by the questionable one.)

So, is this just a product of the dynamics between my co-workers, and I am only involved peripherally, or did I miss the boat for a chance to educate some people?

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