From the Plaza, we drove to Oak Park Mall to visit Dillard’s. An older SA greeted us, and I told her I had a date night with my wife that evening. I was going to wear the Melani leather shift dress silk long-sleeved button-up shirt in bright yellow and needed a jacket in case the evening turned chilly.

She didn’t have any jackets that would work but welcomed me to look. I found a pair of trash bag leather pants and a snug, sequined, long sleeved mid-thigh-length dress to try on.  The SA took those items to the dressing room.

When I came back out in the clothes I wore in, they all looked disappointed. I explained that the pants looked like bad boy-jeans, and the dress was a tad bit small.  They suggested I try the Calvin Klein department upstairs for jackets, so that’s where we headed.

Upstairs, two younger SAs immediately came to help me out and were almost TOO helpful… I must have tried on 15 jackets, but none worked for the look I was going for.  My wife pawned the sale racks and found a nice black & blue collarless open-front jacket with ¾ sleeves and sheer inserts.  It fit well, and it would look good with the leather and the yellow, not to mention that was on sale!

Visit Transgender Heaven

While I was checking out, an older SA was having a nice girl-chat with me about all things clothing. My wife came up to me with a jacket she thought would be cute for her.  The SA said “Oh, I love that jacket!  Show him the BACK of it!”  Although that SA made the only pronoun mistake of the day.  I gave her a pass on that error because we had such a nice girly conversation.

It was time to check into the Phillips hotel in downtown KC.  We pulled up and the valet came out to explain the parking situation. We chose to valet our car, and he treated me with so much respect!  Nobody batted an eye as I got out, collected the luggage, and headed inside.  I love being in the city.

To celebrate the end of our wonderful day of shopping, we changed into outfits for some drinks before dinner. Me in my shiny pleather leggings and new cabernet tunic sweater, completed with my brown booties. My wife wore her new soft sweater pull-over and mint colored jeans.

We strolled to the Yard House bar nearby for happy hour. The bartender took our order without incident and no one took notice of anything unusual with me.  We drank and laughed and just generally had a great time.  At one point, the bartender asked, “What’s the name I can put on the tab?”

I later joked with my wife that he was probably trying to catch me off guard, assuming I might slip and use a more manly name… it was funny. While giving some coin change to my, a dime fell on the floor. I jumped off the bar stool and bent over to grab in without bending my knees. My wife laughed and said, “All the guys on that side of the bar just stopped what they were doing and checked out your butt!”  Ha!  I love the attention shiny leather leggings gets me.

Visit Transgender Heaven

After the beers, it was back to the room. I changed into my yellow silk satin shirt and leather dress; my wife gave me a beautiful medallion necklace to wear.  The dress fit PERFECTLY, and the yellow shirt and black/blue jacket were a total success.  My wife changed into a super-fuzzy short-sleeved white sweater and a burgundy A-line midi skirt.  We looked so cute together!

At dinner, I gave the host my femme name, which was a genuine confirmation for my confidence. We were seated and had a great time enjoying a nice dinner and bottle of wine.  I couldn’t believe I was sitting in a nice restaurant, along with other customers and staff. This was SUCH a dream come true. If you had told me a year ago I’d be doing it, I NEVER would have believed you!

After dinner, we walked a couple blocks to Anton’s, a downtown KC staple when it comes to steak and beer, for a nightcap. My wife ordered a nice sour or saison. I had a Rochefort 10, a Belgian Trappist quadrupel, (I happen to be a bit of a beer snob!) We went out back to the fire pit and had a lovely time enjoying a warm fall evening outside together.

When we got back to the hotel, we took pictures of each other in the beautiful lobby.  When we spotted the shuffleboard table, we couldn’t resist a nice fun game! Back in the room, my wife said, “You had better get back into one of your cute outfits… our evening is not over!”

Visit Transgender Heaven

My wife wouldn’t tell me where we were going. We rode the elevator down to the lobby and walked up to the main desk.  We stepped to the right of the desk, and my wife said, “We have a reservation for 11pm.”  It was then I noticed a sign on a hidden door that said “Speakeasy.”  We walked down a mysterious staircase and found ourselves in a dark, swank, olde-tyme whisky bar!

We both enjoyed a craft cocktail, and I added a glass of good bourbon (neat). I felt so relaxed and cozy, enjoying the atmosphere and our wonderful conversation. There were only a few other customers, and none who paid us any mind at all.

It was one of the best days and evenings that I’ve ever had. We did a similar outing for my birthday at the end of July, which had been my first time in public dressed en femme. This time was so much more enjoyable.  I was more comfortable, knew better how to carry myself. My wife had to remind me once to stop walking like a man and stand up straight. I was relaxed around people so much more, feeling normal in my clothes.

I succeeded in realizing a couple long-time dreams, wearing leather leggings and a leather dress in public. My experience was unbelievably positive, and I enjoyed the fact that I was totally owning it. Sure, on closer inspection or if you heard me speak you would have been able to tell I was a crossdresser. In casual encounters I probably passed relatively well.

Plus, I think I looked sexy in that dress and in those leggings!  Like the lady said at White House Black Market – I have the legs for it!

Be well my lovelies!  If you have not been out publicly yet, find a town far enough away that you won’t risk running into people you know around every corner, and just dress up and go out.  You won’t regret it.  The only thing you have to fear is fear itself.  The world is much more accepting, or at least dismissive enough to generally not take notice.  In either case, nothing beats living authentically, even if only for a short time.


More Articles by Philma Bierstein

View all articles by Philma Bierstein
The following two tabs change content below.

Philma Bierstein

Mid-life CD. Professional, and I get out as Philma when I can. Slowly getting more comfortable in public, but not in my midwest mid-sized bigoted town... I have to travel about an hour to get to a town without aggressive criticism. Out to my wife and a few select friends, but closeted at work and in general, especially most of my family. Wishing acceptance was more normal, but knowing this region just isn’t ready for girls like us!
5 2 votes
Article Rating
Inline Feedbacks
View all comments
Clara Cross
Active Member
3 years ago

Fantastic Philma!

Clara Cross
Active Member
3 years ago

I spent several years in Kansas City, most of the 80s. Loved it. Still miss it a little. And we don’t have Dillard’s here in Wisconsin. Miss that too. And the Plaza. And the BBQ. Ok. I miss it a lot.

Lucie Hamilton
3 years ago

New here.
Delighted that you had a great time without anyone judging you. Wish I had the opportunity to do that but I stay in a small town where everyone knows everyone

Cassie Jayson
Trusted Member
3 years ago

What a wonderful day for the two of you. It sounds like your wife had a great time partly seeing you enjoying yourself!! May the two of you have many more supper adventures!!!!

Mika Malone
Active Member
3 years ago

That was an awesome story. So much girl time. I LOVE Anton’s for the grass fed beef as much as their beer selection. I haven’t been in a couple years though. We’ll have to plan another trip to the city. I probably won’t be buying any more clothes though. I ordered 62 different things recently and I don’t have the closet space for much more. More on the clothes haul later.

Glad this finally got through the editing process because I have been eagerly awaiting it. It was better than I could have hoped.

Marie Chandler
Trusted Member
3 years ago

What a magical evening! Thank you for sharing all the lovely details.

Would love your thoughts, please comment.x
Subscribe To Our Newsletter

Subscribe To Our Newsletter

Join our mailing list to receive the latest news and updates from Crossdresser Heaven.

You have Successfully Subscribed!

Log in with your credentials

Forgot your details?