My sissy wasn't the first man or boy I put in dresses. But I can tell you that she was the first with whom I've truly enjoyed the emasculation process. The others were just fun flings I had while in college and beyond.
I'd fantasized about it before, but never to the extent I practice it now. My first opportunity to do such a thing came when I was a freshman in college. A bunch of us used to like going to see the Rocky Horror Picture Show and really get into the whole audience participation thing.
I ended up going on a date with one of the guys once and after a couple of drinks he admitted to me that he wouldn't mind dressing up like Tim Curry in the movie.
"Have a thing for corsets" I asked Charlie. He admitted he did. His timing was great. It was two weeks before Halloween. He was the hit of the party. I had made him up to look like Tim's twin...lol. After, I had the best sex I had to that point in my life. Totally turned on by having this guy dressed in a corset who was fucking me! The FemDom seed was planted then.
I played with Charlie/Charlene a few more times but for other reasons we never really hit it off.
But the Rocky Horror Picture Show plays an important part in the relationship I now have with my submissive. I remember telling her how hot I thought Tim Curry looked in a corset. That opened the floodgates. In time, she told me all about her own desires.
Now I have a pantiegirl who isn't totally emasculated but she's close. She'll always have those little balls and her little cockette or clitty which is okay with me.
Having them and not being able to use them is sexier to me that not having them at all.