This past summer I found myself on an extended trip to Australia for work and knew that there would never be a better opportunity for Alexis to step out into the world for the very first time. It’s about as far from home as I could possibly be, so no risk of running into someone I know, and it’s winter there (or, what passes for it in that part of the world), meaning I can wear long sleeves and tights, and not sweat my wig off…I did some shopping, packed my girl stuff, and started researching places to go that seemed TG appropriate. Oxford Street in the Darlinghurst area is the hub of Sydney’s gay community and seemed like the best place to visit as my first time out as Alexis. I was ready. 

Or…maybe not. For some reason, ahead of getting to Sydney, I started freaking out. I can’t really explain what happened, but more than losing my nerve, I found myself questioning what the hell I was even thinking. I nearly left my stuff behind in Melbourne! But once I regained my composure, I decided to take a step back and just enjoy some girl-time within the safe confines of my hotel room. I dressed up A LOT and took tons of pictures. It was quite fun and I felt content. But my last night in Sydney, I was sitting in a bar, overlooking the harbor and sipping a beer, and thought to myself, “screw it, Alexis is going out tonight.” Just like that. I was shocked at how peaceful I felt at that realization. Consulting my guidebook, I realized it was only a few train stops to the exit closest to Oxford Street, so I could easily go for a short walk and be near some TG-friendly dance clubs. Maybe I’d just have a drink – who knows? I just knew it was happening.

 Here’s how it went, told in the present tense, so as to accurately capture my feelings in the moment:

Stepping Out Secrets

 I burst back into my hotel room and immediately begin changing. It’s already after 8 pm, and I don’t want to get out too late, especially not having a good sense of how safe Sydney’s train system is. I suspect it’s fine, but I’d be out alone. Don’t want to be too risky! I know already that I’m going to wear my black and white patterned skirt with the longer of two black tops I brought with me to Sydney. I get dressed and head to the mirror. I’m going to go for a little bit lighter makeup, since I don’t want to look too conspicuous, but I need to still do enough to cover the beard shadow. But I go easy on the eyeshadow and choose a slightly more pale lipstick. In the end, I actually think I look more feminine than when I go crazier with the application. This only helps boost my confidence. I put on some jewelry, lace up my black pumps, grab my purse (already loaded with passport, Opal card, credit card, some loose change, and lipstick in case I need to reapply) and head out the door. Being the paranoid freak I am, I immediately check to make sure the hotel room key is still working. And with that, the walk towards the elevator begins. Inside, I’m silently praying that elevator will be empty, and it is. The doors open to the lobby, I take a deep breath, and head towards the front door. There are a few random people scattered around the lobby, but no one even glances my way. A few strides later, and I’m out the front door and headed for the train station.

 It’s a short walk in a mostly darkened street, so I pass a few more people, but no big deal. My heels click on the sidewalk and the wind swirls around my black tights-encased legs. This is the best! As I approach the train station, it suddenly occurs to me how well-lit it is! Well, here goes nothing. Since it’s almost 10 o’clock at night, the station isn’t very crowded, but there are a few people around. I head in, swipe my Opal card, and walk towards the escalator. I timed it well, and I don’t have to wait very long for a train. Boarding the train, it’s a tad more crowded than I would’ve liked, but I’m committed now. I grab a single seat in front of an elderly gentleman as the train pulls away from the station. What now? Well, since it’s 2019, I just do like everyone else and pull out my phone. It’s better than just looking around trying to see if anyone is staring at me! Plus, I can keep my head bowed forward and hide a little more behind my curtain of hair.

 Before I know it, my stop is here. I exit the train and head up the stairs at the Museum exit. Since I had been down here a few days ago, it’s easy to orient myself and head off in the right direction – right past a whole gaggle of people waiting for the bus. There’s no way to pass by without walking right in front of them, so I pick up my pace and head for Oxford Street. The sidewalk rises at a slight incline, and for the first time is dawns on me how much harder walking in heels is when the ground is not totally level. I glance across the street and see a couple of women in short dresses and heels heading the same direction. They are very attractive, but I think to myself, “So am I.” For the first time, I don’t need to look at women dressed like that and feel pangs of jealousy. I’m really doing it. Living my best life, as the kids like to say…I feel sexy, nervous, and happy – all at the same time.

 Now I’m headed down Oxford and wondering how much further it is until I hit one of the dance clubs, without pulling out my guidebook and looking like a dopey tourist. The sidewalks are starting to crowd up with people a bit more, and it occurs to me like maybe this isn’t the best plan. Perhaps this is a bit riskier than I’m actually comfortable with. I wasn’t counting on the walk being THIS far. Figuring I should cut my losses, I cross the street and start heading back to the train. This time it’s a much longer wait for my train, so I sit (with my legs crossed very lady-like) on the bench and play with my phone for a bit. Many people walk by, and a woman sits down on the same bench as me.

After what feels like an eternity, the train arrives, and I once again head to the upper deck and grab a single seat. The closest person to me is sitting across the aisle, and I can’t stop thinking that he reminds me of Peter Parker’s buddy in the most recent Spider Man movies (if that helps gives a visual). I definitely catch him stealing glances my way, though I continue to look out the window, acting like I don’t notice. I have to remind myself that I am wearing a miniskirt and 4” stilettos that lace up to my lower calf, and if I were him, I’d probably be looking at me too! The train gets to my station, and this time a LOT more people get off the train. By the time I arrive at the escalator, everyone is in a clump, and I’m riding up behind a couple with young kids (hey, what are you kids still doing up at 11 pm?), and what seems to be an endless stream of people behind me, in a very brightly lit train station. But you know what? Nothing happened. Did anyone notice that I’m a guy? Maybe. If so, they kept it to themselves. Except for Spider-Man’s buddy, I didn’t even catch anyone else looking at me.

 The walk back to the hotel is uneventful, except that I have a little more bounce in my step, a bit more sway in my strut. I’m savoring these last few moments of public femininity, entering the hotel lobby, past the conventioneers clustered near the bar, and back up to my floor. I can’t resist posing by the window at the end of the hallway, one last twirl before going back behind the closed door.

Though I didn’t quite take it as far as I had planned, this was by far the most public I’ve been as Alexis. As I sit on the plane during the long flight back stateside, I feel a twinge in the arch of my feet whenever I shift position, a reminder of the night out in heels, and never has pain brought such pleasant memories.  Will there be another time? I hope so. I don’t know where, and I don’t know when. But when it does happen, I know I’m going to feel beautiful.

Now girls, I would love to hear about your feelings going on inside of your mind when you made your first voyage out in public as a girl. Please feel free to share them with me and the rest of our CDH readers.

Did all go exactly as planned on your first night night out and how did your expectations change as your first night out progressed?

Did your confidence in being a girl the first time out continue to grow as the night went on or did you get more nervous and decide to seek comfort back at the house? or

Maybe you even decided to take things even further than planned while you were out the first time as a girl. If so, tell me and the CDH reading bunch here how you took things further than planned on your first night out.

I hope you enjoyed my article and I look forward to hearing how your first night went based on my questions and statements above.

Sincerely, Alexis

 

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40-something, married crossdresser - just looking to share stories and make like-minded friends. I have been (mostly) closeted, except for a few Halloween adventures, my dressing has been private. I enjoy creating the most feminine image possible - that's where the rush comes from. I can't ever remember a time when I didn't want to dress like a woman, but as a kid I never imagined I'd be this deep into at my age! But, I think it keeps me young. Hell, better cute than bored!

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Kim Michele
Lady
Member

Good for you Alexis, you got to start somewhere. I went out for the first time last Sunday Sept 29th. I went to a mall knowing it would be crowded on a Sunday, or as crowded as any mall gets these days. I went into a store and bought some sexy cloths and did not seem to have any issues with the employees or customers. I think my first time went better than planned, got several guys looking me over quite a bit and on hey beautiful walking through a parking lot. I hope you get a second chance soon… Read more »

Jennifer Wilson
Lady
Member

Yay for you beautiful!

skippy1965 Cynthia
Ambassador
Active Member

Great article Alexis. My first all day adventure was back in 2016 and I wrote about it here. https://www.crossdresserheaven.com/forums/topic/miss-cyn-goes-to-washington/

The key to success is realizing that 99.99% of the time, reality is nowhere NEAR as frightening as what you imagine it to be. Confidence and a smile will carry you through most circumstances. Know that you belong wherever you are as much as any other person does and you will usually be treated as such.
Congrats on your first outing and don’t let it be too long before your next!
Cyn

Richelle Raine
Lady
Active Member

OMG that was the best story ever Alexis. Once I started reading it, I couldn’t stop! Everything you described is probably how many of us feel and having the opportunity to do it so far away from home must have been exhilarating? What an amazing experience that must have been.

Karla
Lady
Member

HI red your story, I can remember my first day/night out, it was too long ago when I was young,( thin, long hair,) and it was much simplier to pass as a girl. but as I went though your writing I felt the emotion that I feel all the time everytime when going out after all these years last sunday at noon I was all dressed, day time make-up, white dress for the heat, pink pumps + nowhere to go, so I climb the car, went to the convinient store get some water and back, I enjoyed a lot last… Read more »

Paula Rae Jones
Lady

Fascinating story well told. And if that is your picture attached to the article, I must say you are a very attractive girl. You’ve already shared a very personal experience so I feel like I’m prying in asking this, and you can certainly decline to answer, but, if you’ll pardon my naiveté, I’m curious as to how things might have gone if everything had gone exactly as you might have hoped or dreamt that it would? Did you hope to meet someone had you proceeded on to the night spots or was the point just to go out and be… Read more »

Jennifer Wilson
Lady
Member

I loved your story!!! (and I am living in Australia now and really want to visit Sydney!) In the US I have been out several times. And each and every time I got compliments – which made me feel so happy that really pretty women were commenting on me on my outfit. I usually wear dresses when I go out so there can be no mistake that I am a woman (even though I am sure they can tell I am a man). But people really are so excepting. It makes me feel so special to pick out a pretty… Read more »

Simone T
Lady

Alexis, well done you. I dream of being able to do what you did.
Have to say though, being from Sydney and having worked right next to Oxford Street and museum station, I know the slight incline and bus stop you talked about and I think you were only about a block or so from a club that you would have been headed for! So close, it was probably much further to turn around and head back.
But well done you for having the courage to make the attempt 🙂

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