It was a cold and blustery night…isn’t that how most Halloween stories should start? But in my case it was true. There was no rain, but it was windy and very, very dark from the cloud cover.
I have never been out as Janet. I’ve dreamed of it, I’ve thought about it, but I’ve always dreaded potential negative reactions. With this in mind, and like many of us, I sought the shelter of Halloween to make my first appearance.
The preparation was so much fun, working to get everything as right as I could. I started with shaving and showering, followed by moisturizing, nails, then foundation garments. I already had a new outfit with everything laid out, the only real debate was down to what shoes to wear when I was ready. I longed for the feedback of my wife or a CDH friend as to which pair of shoes work best with this outfit? How many times have we done this dance with our significant others? Lots for me.
As I was tucking, putting on hose, cincher, bra, and all the rest, I had the thought to which many women could relate: ‘This is going to be a challenge to disassemble and reassemble if I have to go to the bathroom!!’
I stayed focused on getting my look right and did my make up, styled my hair, and spent way too much time in front of the mirror. I sprayed some Chanel on my wrists, rubbing them together and sniffing them like I have seen so many women do over the years; I threw in a few spritzes for good measure to other key areas. I packed my new Michael Kors purse and wallet with my misgendered ID and some cash. I adorned myself with my earrings, rings, necklaces, and bracelets. Deep breaths.
Oh yes, now the shoes! I debated between some very cute Dansko Tiffani sandals and some off-white slingbacks in a reasonable height (3.3″). I simply couldn’t go out the first time and NOT have heels on!
I felt ready to embrace this!
Into the car and off I go through the city and countryside, eventually pulling up to the bar. I took some more deep breaths and said, “I am doing this.” And with that, I flung open the car door and made the walk to the entrance, in heels, on a blustery night. I pushed open the bar door and worked hard to be as inconspicuous as possible.
Ha! I am 6’2″ in heels, so easier said than done in a relatively quiet bar.
A few people acknowledged me, the bartender came and served me, and it had all become real! I sat and sipped my Cabernet and basked in the acceptance and the little things like my lipstick on the wine glass. I calmed down and realized this was a WAY bigger deal for me than the others in the room. There were some interesting looks from a couple of men but that was about it. I thought better of staying too long as I had a ton of commitments, so after my drink, I left, leaving a nice tip for the kind bartender who was so warm to me—being kind can not be overrated! I stepped back into the wind, managing to keep my hair in place, and started the journey home.
I realized a few things: It was a massive rush being seen as me for the first time. No one had any clue that this was any different than normal—and I don’t think one of them cared. Pick the right venue and the right time; this place had advertised a standing drag show but it wasn’t on last night—hopefully I’ll get the timing right next time.
My biggest take away was that I waited too long. This was a wonderful, validating experience that should have happened years ago.
Finally, this would not have happened without ALL of you! You are all so supportive and willing to help with anything. I truly appreciate that support and knew I was carrying it with me that night.
Janet💋
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Janet, what a great story! Thank you for sharing it. I first went out in the late 70s. I remember it like it was yesterday. I am so happy for you.
Thank you, Terri! I also recently stopped off at Transformations by Rori in Chicago on my trip home. I stopped in drab and left after getting new forms and lots of clothes and wigs to up my transformation! It felt wonderful leaving in hose, new heels, forms, cami, and wig. She is nothing short of FANTASTIC!
Great first time story Janet! It’s one small step for a CD one giant leap for Sister Janet! Hooray for you girl! Going to a Convention of Crossdressers and Trans is another great eye opening experience! Janet if you ever get the opportunity go to at least one of them. As far as the bathroom goes. As long as you face the door you’re doing nothing cis girls aren’t doing. The challenge is going to the loo wearing a gown. Gathering up everything and don’t step on it or dip it in the bowl. Wishing you many more happy adventures!… Read more »
Thanks, Fran! I have looked at joining friends at TG Rocktober in Vegas, Keystone, and the other great events highlighted here. Some day…
Your so very welcome my dear. 🥰
SMOKING HOT story, Janet! I would have loved to be at the bar with you that night. You sound like a beautiful lady! Can you share some pictures of you dressed in that outfit if you don’t mind? I would love to send you some pictures of me! Talk to ya soon, honey!!! – Jen;^>
Thanks, Jennifer! Sent you note.
Thank you so much for a wonderful story. It will help me when I get the nerve to do the same thing, but not on Halloween. crossed fingers. I a happy that you had the courage to face your fears, and it all worked out. Now, with that, I am encouraged.
You look gorgeous and I wouldn’t wait! Pick a fun place and go be you!💋
@Janet Jorgenson Good for you Janet. And now you officially have the ‘bug’.  lol Hope you had a great time. I’m sure you will remember for your next outing all the things you needed to do, and didn’t, like tissues and emery boards, maybe nail glue, the list is endless. Now you understand why a woman’s purse is so heavy.  Hugs, Jillleanne
Thanks, Jill! I had my purse and tried to think through all that could go wrong! I had makeup and even included the nail glue and some replacements if needed. It was actually fun trying to anticipate it and a small source of anxiety. I do have the bug!