Reine you leave out the important fact that this umbrella was to be held in public. It's a very different thing to do something in public and in your privacy. The crossdressing teenager I was may have refused too to hold that pink umbrella. I wouldn't have been any less of a crossdresser for it.
Picturing himself? There is also an important bit here that can be missed. There can be a great difference for a non-MIAD, binary CDer (which I am, despite accommodating to MIAD in the particular context of doing it with my wife) between dressing in women's clothes and seeing the result in a mirror. I have evolved on that point, but for a long time I couldn't stand seeing myself in a mirror while dressed unless I got shaved and made up. The dissonance between my male, bearded face and the rest was too disturbing. But if I just looked at my "female" dressed body in subjective view, or pictured myself as such in my mind, I was happy with the result.
The takeaway here, is that a CDer can be repelled too by his presentation in female clothes.
This is not to say any man would secretly love to wear female clothes, this is projecting too much, but considering that some non-CDers may be a bit excited by wearing female clothes in a private context (I insist on private) even if they would not admit it publicly, that is something I could subscribe to (and may, and I say may, have witnessed in a few occasion to be honest).