Cross dressing can be one way to portray their feminine side. It makes them feel those feelings of comfort and liberation as if a burden has been shed and they’re free. It simply feels good to them.
The feelings bottled inside are not good for a person’s psychological health.
A majority of cross dressers actually began the practice as under dressers because that’s where the society is not going to catch them and disapprove of their practice.
Living the life of cross dresser is like moving between reality and fantasy. The reality being who the person actually is, i.e. A man, and fantasies being who he wants to be, even if momentarily or those feelings that he wants to get out of cross dressing. They fantasies slowly become realities when these people take measures to please themselves; the excitement of becoming a female and that terrifying tickles of what are you losing - manhood.
Similarly, a large number of men (cross dressers) might prefer to wear Kotex Maxi Pads instead of incontinence pads, which are specifically made for urinary incontinence problems, because of their similar level of absorbency.
Simply, whatever floats your boat. No one needs to be critical or judgmental of anyone, just as it cannot be said cross dressing or the traditional dressing is better than any other. Everyone should be free to live how they want to unless they are a potential hazard for others. What someone’s sense of comfort is must not disturb another. The comfort is the boundary; no one should force anyone to go past their comfort.