OK, so when we first started talking about his desire to fully dress, including wig and make up I asked if he wanted to GO anywhere? I guess at that time he had not even considered going out. I figured if he was going to go to all that effort, why not find a place to go while he was in drag? With that seed planted he found a local club for CDers and their spouses. It's a group that has at least one social gathering a month for couples, often to a "safe" restaurant. He filled out an application, with my blessing, and had a phone interview, which I had to be a part of. That went well so Friday we met one of the members for breakfast and an in person interview, in normal clothing. That also went well, so the founder invited the two of us to his home yesterday for some mentoring. The next meeting is in 2 weeks so he wanted to make sure my guy will be ready and presentable as a proper lady.
Literally he had to bring all his femme clothing (which isn't too much at this point), dresses, shoes, stockings, bras, forms, wigs, jewelry, and all his (and MY) make up! He said we would be there all day, as would his SO, and he did not exaggerate. We arrived around 9:30 am, had a nice visit and talk on the patio, and then the work began. This man has been a CD his entire life, and he is pushing 80 but he had so much energy and so much wisdom to share. He told my hubby that he had the wrong bras and stockings and especially wigs. Thank GOODNESS because I thought so too, but didn't want to hurt his feelings. This man put him into a real functional bra, a waist cincher, a padded girdle that gave him the hips/butt of a woman, to proportion to his shoulders & waist. It was really quite a transformation and made the look very believable. He had him wear normal (not sexy) pantyhose and had a TON of wigs for him to try. He tried to teach him how to walk and move like a lady and not to look like a cheap transvestite, LOL. He then spent several hours watching & tutoring him (and me) on proper make up application. I even learned a few things myself.
It was exhausting, really, but he/she got to try a number of beautiful dresses and period pieces with various hats, accessories and wigs. I even tried a few wigs myself!
After the fashion show and photo shoot (I took pictures of his different looks) he washed off the make up and got back into his normal clothes and our host then transformed himself into his female self, while we carefully watched and learned. Then the 4 of us went out to a very nice dinner at a regular restaurant where everyone knows them as both himself and HERself, where we were fawned over. It was great fun but we were dead tired by the time we left there at 10 PM!
Funny thing is, my SO is pretty well over the whole thing, LOL. A cure, perhaps? Just kidding.
In less than a week we've met 3 transvestites in person, and 2 SOs. Prior to this, my SO had never even spoken to someone like himself, other than online. It's an altered reality for sure. What a crazy day it was, and the club is going to be a lot of fun.