But yeah I'm ~235lbs/106kg guy, and I don't like how I look most days in the mirror in a boring t-shirt and shorts, let alone trying to be desirable, so I'm kinda setting myself up mentally for disappointment. We shall see.

Sounds like me a year ago xD

Try find something that suits your figure; fem clothes can be quite good at camouflaging and distracting from problematic areas if one gets the right stuff.

And it drastically boosts self image when you found clothes you feel comfortable in, even if only in certain situations.

And my personal experience in case you don't like your face (I didn't, but I've got gender-related dysphoria in that regard): these femboy-cat-face-masks; wear them if you try out or take pictures in dresses. Allows you to focus on the clothes instead your face. After you found clothes you like with that mask on, you might take a look at some basic makeup. Nothing too fancy, but a bit of foundation, powder, minimalistic eyeshadow and mascara can do wonders.

But essentially: Try it! Do yourself a favor and try it! I wish I would have given in sooner instead of always thinking "nah, won't suit me anyway and I will just look like a dude in a dress". Wearing stuff like that played a huge part in realizing who I am.

(And it gave me a reason to loose some weight. 103kg->88kg since December)

And obviously: Should you find out in the end that fem clothes are just not your thing; that's fine as well! But if the idea was already in your head: try it ^-^