I had an enlightening conversation with a crossdresser once.
He explained to me that he is 100% male. He had no doubts about his gender or heterosexuality. But he dressed up in womens clothes and had a female persona that he would often roleplay for hours at a time. Sometimes he would run errands as his female alter ego, other times he would just lounge around the house, and crossdressing for him was something he really really enjoyed and felt empowered doing.
His justification was that he had been conditioned to view beauty, sexiness, and cuteness as feminine traits. He was attracted to women and these traits and thus had a strong sexual image of what female beauty is. Since these traits were most strongly associated with feminity and women, they were traits he could never take on as a male.
To him, he could never feel beautiful as a man. He could never feel sexy. He could never be cute. Even when he tried to be these things as a man, they always felt forced and limited and insincere. But as a woman they felt natural and authentic and powerful.
This man crossdressed because it let him feel pretty. It let him feel sexy and adorable and let him take on traits his own gender didnt allow. But it was also a greatly sexual experience for him because it enabled him to exude the same qualities he found attractive.
He told me that this is common for a lot of heterosexual crossdressers. Gender constructs and misogyny amplify female sexuality and portray the masculine body as utilitarian.
Theres a Seinfeld episode where Elaine says the female body is a work of art but the male body is like a Jeep thats for getting around. In this same episode, Jerry and his new girlfriend spend too much time naked together and the relationship falls apart because he cant stop imagining her naked (good) and she cant STOP imagining him naked (bad). This episode, he says, strongly contributed to human his beauty ideals. He could never be attractive and beautiful as a man. He could never be a work of art. He would always just be a truck for getting around.
This is something I can identify with on some level. I am rarely able to find beauty in myself or other men. My body feels expendable. So there is a curiosity in what it would be like to have a womans body to primp and preen and feel beautiful. As somebody with low self esteem and poor self image, it is easy to fall into the trap of thinking I would love myself more if I looked like something else.
But this is a fantasy rooted in institutionalized misogyny. The idea that women are innately sexual and men are not harms us both. It is why I know I wouldnt actually switch bodies if given the chance - this construct is not real. Its a fantasy.
So it can be safe and fun to explore in fantasy, like crossdressing, but the shine would come off the apple of the transition was ever real. Assuming you are cisgendered, of course.
Interesting. I actually had a similar perspective when I was younger and had low self-esteem, although I'm not a cross-dresser nor am I transgender. I'm a straight male, but when I was a teenager, I sort of had a jealously and even possibly slight resentment of women for being beautiful, and, as a male, I felt ugly in comparison and, as you said, "expendable". I felt that since (I thought) nobody could value me for my looks, that I was effectively completely worthless, while women had this default advantage of being beautiful and being valued for their looks. And this was something I struggled with on top of all the other self-image problems I had.
This perspective gradually changed as I got older and went through college and whatnot, making plenty of female friends and opening up more, and no longer viewing them as this "other" that I couldn't relate to, and also ever since I started working on my body through working out and whatnot, and obtaining more a "masculine" form as opposed to my skinny as heck teenage self, I do have a inherent sense of attractiveness now that has helped a lot with my self-esteem.
As you said in your post, the beauty ideals of humans is a social construct tied to gender roles, and it harms men and women both. Women have an expectation of looking preen and proper just to walk out the front door, while men have to put much less effort in that regard. And "being valued for your looks", which I was once jealous of women for, is I now realize is not always a very good thing and something women have to put up with on a daily basis in the professional world. There's nothing inherently more sexual about a woman's body as opposed to a man's, but society has placed much more emphasis on women's sexualization, which causes these sort of gender roles.
Going back to my original story, though, I wonder how many guys (particularly ones with low self-esteem) actually go through such a struggle in their younger lives. It isn't something that's easy to talk about, of course.
