>i know that as a fetish it becomes aesthetically unviable after a certain age
A sad truth about crossdressing, or anyone that can pull it off successfully anyhow, yes. But nothing lasts forever as they say, so I think it's best to enjoy it while you still can. If you like it, it makes you happy and makes you cum then why not? ヽ(´ー｀)ノ

Oh, and when you get around to it, don't forget to post pics. ( ´ω`)