A Crossdresser’s Story: First Night Out

Hello again, darlings! How are you doing today? Welcome back to this new section on the website, where we share our personal stories and experiences as a  crossdresser!

If this is your first time here, you may want to look for other stories under this section.

For today’s story, I will be telling you all about the first date me and my girlfriend had while I was crossdressing.

For every crossdresser, stepping out of his house while en-femme is a BIG step.

The levels of anxiety one can reach before attempting to do so are insane.

For me, it was a huge relief having my girlfriend along for the ride and comforting me.

That’s why you’ll find below the story of how my first date with my girlfriend while crossdressing went.

As it can be a life-changing experience for any crossdresser, it was as well for me.

Below, you will read about all the thinking ahead we did and all the nerves that came along to make it a dream date.

If you are wondering how my first date being the “lady” was, keep reading my story!

❤ The Surprise Invitation

To begin with, I would like to add a little background.

My girlfriend and I are both great cinephiles.

Although our likes are very similar, sometimes we couldn’t disagree more.

The point is that we both love watching films, especially at the theater.

And the fact that our very first date was at the cinema is not a minor one.

If you are following this new section of the website, you may already know about the time that I told my girlfriend that I am a crossdresser.

Anyway, a few months after I came out to her and a dozen movies later, she surprised me with a question.

“Would you like to go on a date with me while crossdressing?” I was shocked. And terrified.

“Would I like to go on a date with her as two women?” Of course!

But at the time, I hadn’t been out while en-femme, so it was a big step for me.

The wonderful thing about it all is that my girlfriend was along for the ride!

It was like having a second first date. As such, we planned it with due preparations.

❤ The Plan

As I told you before, we watch a lot of movies at the theater.

There’s one in particular that we love.

It’s cheap, relatively near, with a nice image and sound, and the most important thing: few people go there, especially during the week.

Sometimes, I wonder how it is still open, not that I’m complaining.

As you can imagine, the choice of where we would have our second first date was pretty clear.

We picked the latest screening we found midweek to avoid as few people as possible.

Baby steps, if you know what I mean. The date was set; THIS was happening.

Still, there were some things to prepare. “What was I going to wear?

Is my wig good enough for going out? Which shoes were appropriate for a date at the theater?”

All these questions came rushing to my head as I wanted the date to be perfect.

And determined to do everything at reach to ensure that.

❤ Selecting the Outfit from the Ground Up

It is obvious that as soon as I realized this date was happening, I started to stress about what I was going to wear.

Over the years, I managed to add to my stash of feminine clothes different pieces enough to grow it to a considerable size, including a wig, hosiery, underwear, and some skirts.

But with few exceptions, none of that was remotely appropriate for a date at the movies.

Some outfits were so flamboyant that even at a nightclub wouldn’t go unnoticed.

Let alone the shoes; there is no way to discreetly enter the cinema past midnight midweek walking in 5-inch stilettos.

I had to select an outfit according to the date so I didn’t feel out of place.

As soon as I had some free time, I started to look for outfit ideas online.

To avoid spending a lot of money, I decided that I could use some of the “unisex” clothes that I already had.

To be more specific, I decided that my white Vans shoes were perfect.

Not to mention that I’m somewhat tall at six ft., and wearing heels would only make me more distinguishable among the crowd, something I was trying to avoid.

With the shoe’s choice done, it was time to pick the rest of the outfit.

❤ The Perfect Outfit for a Dream Date

Rummaging through my stash of clothes, I found a mid-length tartan plaid skirt that I thought was perfect for a skater girl look along with my shoes.

To finish my look, I opted for a simple tank top that I bought online, along with a pink and gray wool sweater.

This date was happening during the winter, so a scarf was an obvious addition to the outfit.

It would not only keep me warm but also hide my Adam’s apple in plain sight without much of a hassle.

Regarding the wig, luckily, there wasn’t much maintenance to be done; I just cleaned it and trimmed it a bit to give it a neater look.

The outfit choice was almost done by now.

I added some tights to keep things under control down there and borrowed a few accessories from my girlfriend.

At that time, I didn’t have any of my ears pierced, so I got some simple but feminine clip-on earrings.

Besides practicing my mannerisms and looking for a make-up look online, there wasn’t much I could do in advance. I just had to wait.

❤ The Long-Awaited Date

The day had arrived, and the date was happening, but some preparations were still queuing.

As soon as I woke up, I took my regular morning shower and shaved my whole body while at it.

After my body was smooth and clean, I took the time to pluck my eyebrows a bit and shave my face with due patience.

Achieving a close shave is sometimes hard; it depends very much on the amount and kind of facial hair one has.

To avoid a shadow beard this step must be done as carefully as possible, avoiding letting too much time pass between the shave and going out.

I was a ball of nerves all day waiting for the time of the date, stressing out about my looks and what was going to happen.

It didn’t just feel like a new first date with whom I love; it was starting to look like one.

After my girlfriend and I both finished our work, we got together to prepare ourselves for our date.

She surprised me with a bunch of jasmine when I saw her!

She was being a “gentleman” all around and treating me like her “lady”! We both got dressed, and she helped me a little with my make-up.

I decided with a very simple look, mainly to highlight my natural feminine features and add a little color to my face.

Of course, I couldn’t miss the chance to wear a little red lipstick and a bit of mascara.

Also painted my nails to match! I was looking gorgeous! Simple but effective.

My girlfriend was as surprised as I was by my look! We finished getting ready, and we went out…

❤ The Dream Date

If I was nervous before going out, you can hardly imagine how I was feeling the moment we stepped out of my house.

It was driving me a little crazy. Luckily, my girlfriend was always reassuring and boosting my confidence to follow through.

While she was driving, the touch and feel of my outfit did a lot to tone my nerves down.

The power of clothes sure is amazing! Once we got to the theater, seeing how empty it was, my confidence came back.

More than confident at this point, I would say I stopped caring about what others would see or think.

I was on a date with my amazing girlfriend as her girl. The outside world had nothing on me by this point.

Nonetheless, we bought our tickets in advance, so we avoided any interaction with other people.

After retrieving our entrances, we went right past the door, entered the movie and we both relaxed completely.

As expected, the room was almost empty except for another couple besides us.

We enjoyed the screening, but we enjoyed the mutual company even more and the fact that our relationship got to a point where we could share things like this.

I was in bliss during the screening and afterward, while we were driving back home.

She confessed to me that she loved fidgeting my skirt during the movie and had more fun than she was expecting.

We decided for this to become a somewhat regular thing so I could gain confidence for other kinds of dates.

Once we got home, we decided to open a bottle of wine and toast for this big step taken together as a couple.

And that’s the story of how I went out with my girlfriend while crossdressing for the first time!

I hope that you enjoyed reading the story as I did writing it!

I believe that there’s one universal truth that can’t be denied: love.

With love, all barriers and obstacles fall, and the only thing that’s left is rewarding feelings for each other.

What about you? Did you ever go out with your partner while en-femme?

If so, let me know in the comments below; I would love to read your story.