My first time til now
It all started in August 2019.
Well, of course, that’s not the real start, but that was the ignition.
I’d been dressing since early grade school, and I had a few unconvincing outings as a late teen.
I went into the military to fix whatever was wrong in my head and did all the things to try and overcome it, family, career, and respect in town…
And there was always something in the closet. My wife always knew about it, and it was always an inside joke (and a bit of private fun) between us.
I’d been on several fetish sites, that’s all I knew about crossdressing, until…
In about August of 2018 I found this site… there were people JUST LIKE ME! After about a year of being a Lady dipping her toes in the pool, I had some friends, and I wanted to raise the bar, as it were…
So back to August of ’19… I decided to become a subscriber here. I checked the packages, and Duchess seemed right to me, so I did it… and my world changed. Quite literally!
I already had friends here, and I knew several of the staff, and we hit it off. Now, for you big city girls, I kinda have to tell you where I am. I am in a farming and law enforcement city in the middle of nowhere. Everyone I meet when I go out is one of these, generally, and if they aren’t teachers or mechanics, they’re usually ex-military.
We are about halfway between Palm Springs and Phoenix, truly the middle of nowhere.
There aren’t opportunities for cross dressers in my town, put it that way.
However, there was this concept that a few of us would meet in Palm Springs sometime in October… that sounds cool, and it’s a fair distance away from where I was afraid to be outed! As the time ticked down, we decided to meet on Halloween. A Thursday evening, we’d go out to dinner, have a few drinks, party a bit, and be out of there and no one would know the difference!
Mrs. Jay (my wife) wasn’t worried about me going astray, and she wanted to stay home and pass out candy (we live in a good neighborhood and people come from far and near to trick or treat in our neighborhood).
So I hooked up with Amanda and Melissa in the same hotel. Melissa and I went to Amanda’s room to have her do our makeup, and then out to dinner with Jennifer and her lovely wife Cindy. That was just too cool! Then we left Jennifer and Cindy, and met another Melissa to go to the club.
What we hadn’t realized up to this point was that Palm Springs Pride started the next day. As we got to Hunters (the club) the street was packed… to say that it was elbow to elbow would be an exaggeration, we didn’t have elbow room at all.
After many hours, and many many drinks, and loads of fun (and my first trip to the Ladies’ room) we all made it back safely to our rooms to sleep it off…
About three weeks later, I was in Las Vegas getting my first makeover! With Mrs. Jay by my side!
Mrs. Jay and I have been out about 20 times since with me dressed (I think she likes partying with Billie better than with her husband), probably about 8 nights total with Amanda, and I’ve met more girls from here on CDH and other places than I can count! And I’m a hugger, if I were to put a number on it, probably around 50 girls I’ve actually hugged…
And I don’t make commissions, I promise you, but it all really started when I upgraded from being a Lady to being a Duchess…
Please take the time to either respond to my article or answer one or more of my questions posed to you below:
- Do you live in a very conservative part of the country where you would feel very uncomfortable being out in public as a girl? If so, what city is it?
- How many times have you met in person with other cross dressers and how did the meeting go?
- Does your wife either approve of you going out in public as a girl either with her or with a group of other girls?
Sincerely, BillieJay aka Chat girl