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

En Femme Style


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a little on the experienced side of age. I love motorcycles, painted toes, high heels, and skirts. I am a professional in an "old school" technical profession. a proud US Navy Veteran. and happy to share experiences with others in 2019 I went out with the girls for the first time, and I've had a ball doing it since. most of the time my wife, "Mrs. Jay" goes with me. I've met (and hugged) about 50 of our members when I'm out, always en-femme, and enjoy our adventures. hopefully that number will grow, hugely.
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Jennifer Swanson
1 year ago

Hey BillieJay, life is so much more fun when you realize no one else cares and nothing else matters. So glad we met for dinner. And no, I had no idea it was your first time out. Confidence builds over time and you live close to the greatest place for crossdressers, Palm Springs. Hope to see you more in the future. Hugs Jennifer and Cindy

Jennifer Swanson
1 year ago
Reply to  BillieJay

Hope to see you in Las Vegas. Let’s get out in Palm Springs when the weather cools. Hugs Jennifer

Active Member
1 year ago

Hi Billie. A nice story! An exciting journey. Living in Central Misery, it can be uncomfortable. But I go out anyway. I am caring less and less what others think. And I have been out and met others at least a dozen times. And never had a bad experience. The Ladies from CDH are wonderful. Even those I have met not from the site. As far as SO, thats a non issue. But in the past, no way! Hugs Pru

Amanda Amore
Active Member
1 year ago

Hey you! Love the story! So happy I was part of this.


Amelia Love
1 year ago

Hi Billie;
I love your story. It is another inspiring example of the dusty unclear road ahead that can have all the stops along the way as long as we find ourselves in the right place. Joining CDH a only a few months ago will hopefully bring that first and more for me someday. Thank you for taking the time to write some of your experience.

Hugs Amelia

Amy Myers
Noble Member
1 year ago

To try to answer your questions, first of all, I live in what I call Farm Country which is in the Southwestern Ontario area, so it is more conservative with a lot of religious conservatives too. However my experiences have belied this. For this reason I was first very shy of going out locally, but I have not ever had a bad reaction whenever I have been out. For the next question, I have to confess I have lost count the number of times I have been out and met with other crossdressers. It was through a couple of the… Read more »

April Meyer
1 year ago

Billie I am so glad I have had a chance to be with you a few times on your times out!! You’re beautiful and lot’s of fun to party with. Tina is a blessing peace and love dear

Cassie Jayson
Trusted Member
1 year ago

Hi Billiejay. loved your story, I’ve read of some your adventures on the chat, although I don’t go there to often. It is stories like yours and dozens of others here at CDH that have given me the courage to go out on a number of times. I live in central Iowa – a town of about 1300 and work in a collage town of about 70000 (Ames). I am sure a few neighbors have seen me walking in fem between the house and the garage. I have walked the mall twice now in fem, once stopping in Torrid and… Read more »

Sarah Lane
Active Member
1 year ago

Great Story. Awesome that your wife comes out with you. I live in a Country Town and as far as I know there are no other Crossdressers here. However there is a get together that happens every few months in our biggest city which is about an hour away from me. I wanted to go last time it was on but when I ran it past my wife she was not keen at all. She is happy for me to dress at home but is very worried about someone seeing me and it getting back to our family and kids.… Read more »

Michelle McQueen
Active Member
1 year ago

Hello Billyjay. I love your steampunk outfit! To answer your questions – 1) Yes I live in a very very conservative and religious part of the country where there is no place at all to go out dressed. Its SC, where Lindsey Graham comes from close by here if that gives you any idea of how conservative this area is. It sucks for us CD people! I hate it here but can’t leave so I go out of town when ever I get an opportunity.. 2) I’ve been able to meet with other CD’s about a dozen times or so… Read more »

Michelle McQueen
Active Member
1 year ago
Reply to  BillieJay

Ok thanks for letting me know. The editor should have stated that. I’m still learning this site which is sometimes confusing. Some things aren’t clear or easy to navigate. I hope my experience gets better. .

Autumn Valiant
Active Member
11 months ago

OMG I love that outfit!!!
To answer the questions…… Very conservative area of Long Island 50 miles east of Manhattan. Smithtown NY. I have never been out with other CDs. My wife knows a little, Likes that I wear panties, I believe she suspects more but doesn’t really know. She has given me mixed signals about some things so I haven’t come out to her yet.
Thanks for sharing your experience in this Article.

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