I've dressed since a small child, always in secret. I'm definitely on the trans spectrum and now often (about once or twice a month) go out in public presenting (respectfully dressed, and reasonably passable) as female (with similar friends). Even been out shopping in daylight like this. Yes, my wife does know. And supports me, often buying me things to wear.
BUT I've not (yet?) dressed while in a cuckold scenario. I've kept it quite seperate, because I don't generally see my dressing as sexual.
However, I do think about it. A lot. But not so much as I normally dress en femme. Specifically, the sissy thing does turn me on (pink lingerie, lacey girl socks, frilly knickers, bra, babydoll, etc.), probably because of the humiliation angle. I also think often about dressing as a schoolgirl while a guy is fucking her. It just feels soooo submissive. I think it is only a matter of time before I do it.