The thing is though, that poor Chris was not really that ugly until he got deeper into the Tomgirl BS relic of failure. I don't know what it is, but it's like as soon as he put on a skirt and bad make-up he started to get older, fatter, and weirder looking. Like I said, I think Chris wants to believe these things are true and with his badly wired brain, there's enough elbow room for Chris to see himself as a lovely lesbian. I feel like, the way he dresses (5 year old, old lady, teenage prostitute) is very similar to the way some children act or behave. Sometimes they like to wear certain articles of clothing because they like the way it looks, because they believe it makes them look good, or because they simply like the way it flows. Thankfully, children don't have the ravages of old age along with puberty and adulthood to prove them wrong. I think Chris might have a clue that the way he dresses is highly inappropriate, but it's his only way to deal with things he can't control or understand.
I am just not sure if he actually sees himself as a pretty lesbian. Without a doubt, Chris went from looking like a frumpy guy with a very questionable fashion sense to something borderline non-human, once he decided to dress as a 'tomgirl'. But I suspect that Chris himself is aware that nowadays at least he is not exactly attractive. I wouldn't be surprised if he actually thinks the tomgirl outfits make him look better than he would otherwise come across- which is absurd enough- but I can't see present day Chris truly convinced that he is hot and that women would be dropping their panties for him if only they gave him a chance.
There may well have been a time when Chris thought he was hot but those days are long gone. He may not realize just how disgusting he is, but he knows on some level that people find him scary. I am sure he still hopes a girl will one day want to be His Sweetheart that he built From The Ground Up but these days Chris seems so depressed that odds are he knows it will never happen. He has even said as much recent-ish emails.
In other words, the way he tries to act sexy on videos in order to appeal to the ladies, is cringe-worthy indeed and enough to terrify anyone but it seems more like compensation more than anything. A bit 'fake it til you make it', if you will. There are moments when he may be convinced that he is indeed hot and sexy but for the most part, he seems to be just going through the motions.