Going on a Date With My Girlfriend en Femme

Being a cross-dresser means we must try to overcome and surpass our limitations each day.

And each little progress we make can hugely impact our future.

A couple of weeks ago, I made what I consider to be tremendous progress, and I want to share it with you.

It may serve as inspiration to someone.

I’ve managed to go on a date with my girlfriend publicly. But not a regular date as usual.

Instead, I was in my Elise persona. That wasn’t the first time I went out en femme.

But never before had I gone like that on a date, for hours, and only the two of us.

So, if you want to see how things turned out, keep reading!

1. Dressing up as Elise

About two weeks ago, My Girlfriend and I decided to go on a date. We are both graduating from the same college.

We were loaded up with assignments and didn’t have much time to spend together. The last time we had a date was over a month before this one.

So we decided to do something memorable. She’s been aware of my being gender-fluid for over two years now and has always been supportive.

So when I suggested going as Elise, she was quite excited.

The next thing I knew, I was taking a shower and shaving to be as feminine as possible.

Yet, the process was rushed. Then, the cross-dressing process began.

It takes around an hour for me to transform myself into Elise. I start with shapewear, followed by my underwear.

I was at my GF’s place that day and had forgotten my breast forms at my apartment.

As it was a cold evening, there was no point in showing off cleavage, so I went with the stuffed Bra approach.

Still, I missed the volume and realism I get with my Roanyer breastplate.

As for my outfit, I had chosen a black sweater, black shorts, and thick pantyhose (As I hadn’t shaved my legs so well, plus it was cold).

For footwear, I wore some gender-neutral Converse shoes.

I had a dark green jacket tied on my waist to complete the look if it got colder.

My GF insisted on doing my makeup, so I let her.

As she’s a cis woman, she has more experience with makeup in general, so it was a little faster than usual.

It was a simple contour and color correction to hide my five o’clock shadow, plus a few feminization tricks on my eyes and nose.

Instead of lipstick, she applied a lip tint solution with moisturizing properties, once again, due to the cold and dry weather.

Last but not least, I wore my best wig, and she helped me style it.

2. Deciding on where to go

Now, we were ready, but where should we go? It was around 10:00 PM on a Saturday, and few places near us were still open.

That’s because we live in a district with primarily residential buildings full of other students.

So there are few places to go late at night. But we managed to find a restaurant not too distant, around five blocks away if I recall correctly.

The GPS app said we could get there by car in minutes, and it wouldn’t be closing for the next 2 hours.

We also looked up the prices, which seemed decent, and there were no complaints about LGBTQ discrimination.

Still, we can never be sure, and my country has been breaking records of intolerance in the last four years.

So, I practiced my voice and hoped to pass as a woman.

3. Ordering food and waiting for it

Once we got there, we noticed that the place wasn’t as empty as we thought.

At least five tables were full of people, but we still had plenty of space.

My wardrobe is limited here, as some of my clothes are in my hometown.

And I wasn’t as prepared for the cold weather as I thought.

What I mean is that a combination of shorts and stockings wasn’t the best one possible for this scenario.

I didn’t protect myself as much as I wanted from the cold, and some guys stared at my legs in a way my girlfriend described as “lustful.”

We tried to ignore that and sit as far as possible from them.

But at least it seems that I was passing as female well enough.

We got the menu and started to look at their range of sandwich combos.

We decided to share a Large burger with a side of chees-covered fries and a bottle of soda.

We got a large cup of açai topped with Nuttela and some fruits for dessert.

However, I was still insecure about my impression of a feminine voice, so I barely spoke to the waitress.

Still, the few words I said sounded feminine enough, according to my GF once again.

But most of the time, I was just nodding or pointing at something on the menu.

I’m still surprised we could agree on what to order with this kind of communication.

But it worked out. I also want to mention that the waitress referred to me with feminine pronouns.

So I guess either she’s supportive of LGBTQ people, or I’ve managed to pass as a girl.

Nonetheless, it was great for my self-esteem.

4. Eating and checkout

Our order was ready in less than 15 minutes.

And differently from other experiences, I didn’t have any problem eating as a girl, at least from a practical point of view.

I mean, the lip tint didn’t make as much of a mess as lipstick usually does, so my makeup was intact after eating.

Besides that, I’m no longer struggling to eat while wearing shapewear.

I use a combination of two waist cinchers and a body-shaping jumpsuit.

But as I’ve been cross-dressing more often, my stomach is getting used to the compression.

Now, I can eat whatever I want en femme without feeling pain in my belly.

However, I still need to practice some etiquette so I don’t look like a savage at the table.

I still have pretty masculine manners and body language while eating, but I’m working on it.

As for checkout, I asked my GF to pay with my credit card. I lent it to her, as well as a password, once again due to my issues with my voice.

I was a bit afraid of interacting with the cashier. That’s because I subconsciously felt that I would sound too masculine and ruin an otherwise perfect illusion.

So after we paid for it, my Gf returned my credit card and kissed me.

Ironically enough, this made a few other clients uncomfortable, and we got some stares from them (including the guys from earlier).

5. After we went home

On the way home, we started to talk about everything that happened, with her pointing out what she noticed and me explaining how I felt.

This kind of feedback is important so I get a better perception of how people see me while en femme.

In the end, my self-esteem and confidence increased due to the positive tone of her comments.

But I still have a few insecurities to work out.

Once we got home, I was eager to take off my shapewear.

I have a rather masculine shape, and I need a lot of compressions to emulate feminine curves.

Still, it was more a matter of being up late than endurance.

I decided to take a few pictures of myself before doing so and didn’t even have to fix my makeup.

My wig was also still looking decent. And I guess seeing myself in the mirror made me want to stay as Elise a little longer.

But after taking pictures for a while, all I wanted was a good night of sleep.

So, with some help from makeup removers and cotton balls, I turned into my male self again.

That is, of course, for a matter of comfort, as I was still Elise on the inside.

6. What I learned from it

If I were to make a balance of things I learned during this, I guess I could point them out in order.

The most important thing, of course, is that Cross-dressers often underestimate themselves.

Both in terms of passability and in things they can accomplish.

We can reach our full potential if we overcome our fears and limitations a little bit every day.

Another lesson is that discrimination affects not only our gender identities.

People looked at me and saw a girl at that restaurant with no clue of me being trans or a cross-dresser.

Still, once my girlfriend kissed me, some people looked at us dismayed.

That’s because what they saw was a lesbian couple. It shows that there’s still a lot of prejudice and discrimination toward sexual orientation.

But love is love, and I hope all forms will prevail.

I still do not regret going out on that date. The experience was fulfilling, and I recommend other cross-dressers to try it out.

There’s a lot we can learn from it. And step by step, we build our journeys and collective history.

Be prepared to face your challenges because once you emerge victorious, you’ll be a whole new person.

And in the end, share it with other cross-dressers so your experience can inspire them!

Now, If you already have something to share with us, feel free to do so in the comments!

Learn More:

First Date Mistakes Crossdresser Can Avoid

Dating Tips for Femboys

2023 Transgender Dating Tips

Dating as a Femboy

Quiz:

What is the worst thing a cross-dresser can face in a situation like that?

A. insecurities and lack of confidence


B. Discrimination


C. Lack of practice

Get Results