Is that a guy or a girl?

Sam asked: Why do you think Girl Looks Like a Man contests have never materialized?

Sam posted about the Dude who looks like a Lady contest that was held at Relay for Life on Friday evening.  I was there and I thought it was pretty amusing to see the guys dressing up like girls and "strutting their stuff" acting like us females.  Raising the question as why Girl looks like a Man contest haven't appeared yet is a very good one and it triggered some thoughts of mine.

First off, I think it's simply socially acceptable for females to wear mens' clothing.  Today, women wear jeans, dress pants, blazers, shirts with collars, and even ties- yet they are looked at like it's completely normal.

Secondly, I thought of the growing rate of gays coming out.  Since I moved to MA, I've noticed there is a massive amount of homosexual people, and some females simply dress themselves as a guy because it's more comfortable for them.

I think ideas such as above have been though of when contests like that are created, plus some females just look like males.  I also think it's a way to stay away from avoiding some people.  I know some women who naturally look like a male, and they are very uncomfortable with it, and often take things like that offensively towards themselves.

Why do you think people are so afraid of offending people?  And how it gets to a point that people even lie to avoid the offensiveness?