The First Time

I get a lot of emails about going out for the first time en femme and what my experience was.  I’ve written about it here and there but I think it’s time for a full recap of that day.  Buckle up and fasten your garter belt, this is going to be a looooong one.

When I talk about the first time I went out en femme, I am talking about the first time I woke up, dressed in a cute cami, black cardigan, floral skirt, black stockings, black heels, did my makeup and nervously stepped out into the real world.  But that wasn’t the first time I went out.  It was the first time I went out during the day, but even that isn’t exactly true.

The first time I went out en femme I went to The Townhouse (now named The Black Heart).  The Townhouse is/was the oldest LGBTQ+ bar in the Twin Cities and is almost a rite of passage for a girl like me.  It’s usually the first place someone like us goes to.  Although it was the first time I left the house dressed, I don’t really think of it as the first time out as I went from my home to the parking lot to the drag show to back home.  No one batted a false eyelash at a girl like me.  It was about as safe as it gets.  And thank God for that.  When you go out for the first time it’s helpful to go someplace like that.

The first time I went out during the day and went somewhere that wasn’t an LGBTQ+ bar was when I had a dress altered.  My wife gave me a beautiful gown for my birthday one year and I wanted to have it altered so it would fit me better as it was a little large and it needed to be taken in.  I made an appointment at a seamstress, got dolled up, and had a few fittings.  This was also a fairly safe adventure as I only went to one place and interacted with one other person.  

But both of these experiences took away from the “firstness” of going out en femme.  I learned how to walk in heels on the sidewalk, how to use the ladies room, how to drive in stilettos.  Baby steps before my first proper time out.  Getting the dress altered and walking to the seamstress took away some of the fear and nervousness of going out during the day.  Although I only spoke to one other person I didn’t notice anyone staring at me while I drove there or walked to the shop from where I parked.  I told myself if I can do all of that, then perhaps I could do more.  

It took a few more months to work up the courage to take the next baby steps.  But in retrospect they weren’t baby steps, they were huge, huge strides and struts forward.  

Why did I want to go out?  I was tired of being in my living room.  I wanted to experience life en femme.  I wanted to stop for heels while wearing heels.  It was nothing more (or less) than that.  Once I decided to have this experience, I needed a plan.  Where would I go?  Eventually I decided on getting coffee in Uptown. 

Uptown is a neighborhood in Minneapolis where twenty years ago was a lot hipper, a lot cooler, a lot more independent than it is now.  It was, and I suppose it still is, the gay friendliest part of the Twin Cities.  I knew that although I would stand out, I also knew that I wouldn’t be the first t-girl that people in that neighborhood would see.   If you are nervous about going out en femme (and of course you are) it’s helpful to go someplace like this, whether it is a cafe or a bar or a part of the city  Of course, I know that not every city has a place like that, so you may need to someplace that does.

How did I work up the courage?  The bar and the seamstress experiences were good first steps.  I learned the fundamentals (if you will) of going out en femme, such as getting in and out of a car in a skirt.  I knew I would be around other people on this next adventure and I would be paranoid and scared and nervous and I would have enough to worry about so I was glad I didn’t have to learn some of these things while I was dealing with my nerves at the same time.

How did I get over the fear and nervousness of being recognized?  Perhaps its naive of me, but I don’t think I am recognizable when I am en femme (or at least I hope I’m not).  I know some days I look VERY male when I am en femme but that’s okay.  I KNOW I’m transgender and I don’t think anyone thinks I am cis.  I know I’m trans, they know I’m trans, and I know they know I’m trans.  But I didn’t want (and still don’t) to run into anyone I knew.  I also wanted to go to a more liberal, more artsy part of the city.  Cue Uptown. 

I live about twenty miles from Uptown so I felt it was far enough away from most people I knew and the risk of running into anyone was pretty small.  I also was leaving for my adventure early enough that getting coffee was really the only option for that time of the day.  The plan was to park, get my coffee, and go home.  In boy mode this was as boring as it gets.  For Hannah, it was like going to the moon.  In heels.  

I left the house before the sun was up.  Going that early was part of the plan, but I also was too excited and nervous to sleep.  I drove to Uptown and trembled the whole time.  I was worried about being able to drive in heels especially with my foot shaking nervously the whole time but I made it.  I parked in a public ramp and made my way to the coffee shop which was located in a small shopping mall.  Although the stores were closed, you could still access the mall.  It had been a while since I had been to this coffee shop and was surprised that the cafe was no longer in business.  My perfectly planned morning now had a fly in the honey.  

In boy mode this would be no problem as there are dozens of places to get a coffee in Uptown but things were different, I was in a new world.  I was determined not to spin on my heels and go back to my car, I was doing this.  I walked two blocks to another coffee shop and nervously walked past the cars in the street and the other people on the sidewalk.  

No one cared.  No one looked at me.  Well, sure, they looked at me similar to how you look up when you notice someone is near you, but it’s not as if people were gawking or staring at me.  Just a girl out for coffee.  

I opened the door to the coffee shop and the cashier greeted me, I ordered my coffee, gave her my name, and a few minutes later the barista called out for a vanilla latte for Hannah.  I thanked her, she wished me a good day, and that was that.  It was a new world, I had accomplished something small and mundane and life-changing.  And it was easy.  It wasn’t a big deal.  I did it.  

The coffee shop was attached to a small grocery store and not knowing what else to do I went inside.  I sipped my coffee, listened to my heels click on the linoleum, and soaked up the day.  Most of the people in the store at that time of the day worked there.  They looked up as I approached but there was no sign of smirking, eye rolling, or staring.   No one cared.  Or if they did, they kept it to themselves.  

After I wandered around for a bit I headed back to my car.  Paid the automatic gate and left Uptown.  It was still early and the sun had just popped up.  The plan was to head home after getting coffee but I was too awake, too alive, too excited to go back.  Since it was still early, there were only a handful of places open and luckily Target was one of them.  I went in, headed to the Starbucks inside, bought another coffee and wandered around the store, beaming the whole while.  Employees and shoppers smiled at me, and I smiled back  I looked at dresses and just lived in the moment.  

A girl can only kill so much time at Target, so it was time to move on.  By this time a nearby mall opened and I spent more time there wandering around.  I drank more coffee.  I smiled, I strutted, I had the door opened for me, I felt the wind in my hair.  

It was time for lunch and I ate out for the first time en femme.  I popped into a Noodles and Company, ate my salad and by then I was tired.  The coffee had worn off, my feet were tired, and the thrill of going out was coming down.  I went to my car, and drove home.

I had a lovely time.  Everyone was so kind to me, or they ignored me completely.  Not a nasty comment was heard.  Usually I’m asked “what did people think?”.  I don’t know.  I didn’t ask them, but I learned that when you act like you belong, when you are dressed to blend in, no one really notices.  They think you belong there.  And I did.  Girls like us belong everywhere.

I learned a lot on my first time out, and when I went out for the second time, I realized how much more I learned than I had originally thought.  The second time I went out was a few months later.  I was encouraged and emboldened by my first adventure and I had naively assumed my second time out would be just as wonderful.  It wasn’t.  I went to the same mall as my first time and I had a lot more stares than I expected.  I couldn’t figure it out but I realized it might have to do something with my outfit.  I wore a tight bodycon dress with knee-high boots.  I looked cute, but perhaps a little… spicy for the mall on a Saturday afternoon.  Or maybe not, perhaps there was a store giving discounts to Rude People Who Stare At Transpeople that day. It’s impossible and pointless to speculate what people are thinking.

Maybe I was nervous this time and people could sense my anxiety. Perhaps the constant looking around and over my shoulders caught people’s attention as I was acting a little off. These days I am much more comfortable and confident and can look around a lot more subtlety.

I learned that you need to dress for the occasion, for what you’re doing, for where you’ll be.  This is not to say you can’t dress cute or wear heels but perhaps I was dressed for a nice dinner out or for cocktails, not for the mall.  I drew less stares the first time out because I looked like a girl on her way to work.   I learn something about, ah, something, almost every time I go out en femme.  Most times I go out are wonderful or at least uneventful.  Rude comments happen but they don’t happen often.  No matter how many times I go out, there’s still apprehension, fear, and excitement.

Love, Hannah  

13 thoughts on “The First Time

  1. At 70 and still in the closet, I nevertheless revel in the ‘out there’ adventures of other ladies; however vicarious my pa own participation. Some of my friends wonder about my enthusiasm for something which I might never enjoy. I can only say that I am glad for every one of you who do go out. ” As it says somewhere, “Rejoice with those who rejoice.”


    1. HI ANDREA, I am a 71 yo crossdresser and I am also in the closet. I have been crossdressing for about five years. One of my resolutions this year is to go out and meet other crossdressers. I finally worked on the resolution and I am planning to meet with other crossdressers in two days at one of their regular meeting. I am a bit anxious, but I am looking forward to it. I have accumulated a femme wardrobe over the years; I am sure that I will have some fun trying on the items before I go out. Likewise, I am sure that I will learn much from this experience.


  2. The first time I ever went out was the very first time I got a full makeover… it was just the drive back home from the boutique, but still awesome! The next time, it was out to dinner with the trans social club.


  3. Perhaps you need to dress at the same level as everybody else does? That way you won’t stand out.

    What did you do about your voice, its one thing looking the part, but as soon as you attempt to order something, does it not give everything away?


  4. My 1st time out was awesome, I had looked forward to it for awhile. I wasn’t nervous or scared in any way, I just wanted to be out & beautiful & I thought I was. I’m not worried about people staring or what they think, it just doesn’t matter. I just love being out en femme & I always look forward to my next time!


  5. Its been a long time now, more than ten years since my first outings. I was somewhat ill prepared the first time out the door, making the experience both nerve-wracking and exhilarating. After a few times out, just daylight forays to the mall, Starbucks and the grocery, the nerves mostly went away. I never felt that I passed, but I dressed to blend in and succeeded.

    It seems that interactions were very positive. People seemed genuinely curious and encouraging.


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