I’ve been thinking about this whole transformation thing, and the kind of life and adventures that can be enjoyed from it, besides the experience of being a female. One of the things that really help is being young; I’ve seen many pictures of guys dressing like women and when they are over sixty they look more like a grandma escaped from a nut house!
So I think, being now 50 years old, I can consider sane to try this whole thing until I’m 60 years old, and then stop. I want to look like a real woman so to feel like a real woman, and not look like a weird thing that depends in the complicity of other men to make her feel a woman.
As you know, the best time for women is when they are young since so much importance is given to beauty and sexiness in society. Once they become older, they start struggling with wrinkles, sagging skin, grey hair, etc. something that is not so important in men.
I guess it all comes to instincts. From a very early age girls are taught to make themselves beautiful and attractive so to “catch” the best possible man, while boys suppose to become good income generators, which will turn them into a “good catch”, giving them the possibility of choosing among the most beautiful girls.
From that point you’ll see that beauty is perhaps the most important part in society for a woman, while personality would be the one for men. That’s why when women get older they suffer so much with their running away beauty, and struggle to keep it for longer with the aid of technology in the form of creams, make up, tints, etc.
For these reasons from society rules of beauty and sexiness, it seems that the ideal would be to be a woman when young and a man when older; and since I started this whole thing very late in life (my 50’s), I cannot expect to have a long time available for me to do it. You can see in YouTube young guys crossdressing and they really look like a sexy girl! But in those same videos an older man cannot get the same results.
For that reason I believe I shouldn’t consider crossdressing beyond my 60’s, if what I want is to really look like a sexy woman. Actually, I shouldn’t consider crossdressing after 50, but since I’m already in my 50’s and don’t want to discard this experience as “too late in life”, I have no choice but to “extend” the margin up to 60, so to still have some time to try, and in which case this whole thing have a span life of ten years and without expecting the best results but just a honest try, and after that it’ll be time to get rid of everything acquired for that purpose and let the body hair grow back to a trimmed length (for personal comfort), and just live the rest of my life only as a man, while keeping the time between 50 and 60 as a nice memory and the satisfaction of having tried, so not to die with the doubts.