I really don't think that being a crossdresser and being tired of being a man are related. Its more of a different way of expressing dissatisfaction with responsibility and gender roles. Certainly a crossdresser could be tired of being a man when you'd rather be wearing a dress than a suit. But one could also simply be tired of all the obligations of the gender role in general. As others have said the expectations of manual labor, auto and home maintenance, bread winning, a certain stoicism can be draining. (don't get me wrong women have equally tiring expectations) While these male roles are no longer absolute the pressure, both self imposed and external is very real. While a typical male would never consider taking on a female role, a crossdresser who has already crossed the gender boundary with respect to clothes at least may entertain the idea of escaping whatever aspect of the male gender role the dislike by being female. A typical male may be more apt to say "i'm tired of... my job ...my life ...being an adult....)

As far as what it means to be tired of being a man.

- I wish I could look at clothes I like when I go shopping.
- I wish I could compliment a dress or shoes etc with out seeming weird or creepy.
- I wish I could buy myself tulips once in a while.
- I wish I could get rid of body hair.
- i'd love to dance more like a girl (although I'm built like a tank so it would look odd i'm sure.)
- and yes I wish I didn't bear total responsibility for the cars and the yard maintenance without my agreement simply because "those are man things."

While all of these are possible I would have to break the gender role barrier to do them. So when I feel trapped being responsible for things or being prohibited from things I might think "I'm tired of always being a man"