Dressing up in Front of My Relatives for the First Time

Before deciding whether we should come out or not, it’s useful to gather some information about how people would react to that.

But it’s only when they see us dressed as a woman that we can be sure of their reactions.

With that in mind, many of us take advantage of a few opportunities and excuses so we can crossdress without coming out.

That’s what I did this year, and I consider it to be one of my best crossdressing experiences so far.

The opportunity I used is a holiday in my country during which crossdressing is a common activity, albeit in a more exaggerated fashion.

Cross-dressers need to share their experiences to encourage our sisters and help them build confidence.

As this experience helped me to learn a lot, I’ll share it with you. I hope you may find it useful somehow, as I did.

1. A bit of context on the holiday

The ake-up in question is the Brazilian carnival, which happens in February.

It’s a local festive tradition, and it involves dancing and costumes.

But most people don’t take it too seriously.

The majority of the costumes are meant as a joke, and it’s rare to see someone putting any effort into them.

But amidst the many traditions, it’s common to see men dressing up as women and vice-versa.

The problem is that they usually don’t even try to pass, using little to no makeup and exaggerated costumes.

But some people still do great costumes despite that, and crossdressing, in general, is encouraged.

2. Building up confidence

The celebrations take place in big parades across the city, with people partying and dancing to popular songs in costumes.

But because of the pandemic, most Brazilian cities have forbidden parades for the last two years.

So only small celebrations were allowed to happen.

This year, my relatives decided to do one of those, to reunite the family after a long period of social distancing.

They told us to bring a costume and some snacks, so we could spend time eating and have a good time.

As soon as I received an invite, I knew what I had to do. But I wasn’t so confident that I could do it.

I wasn’t sure how they would react to me presenting as a woman in such a convincing way.

But knowing that I was going to use the carnival as an excuse, I could say it was a prank and get away with it.

Besides that, my girlfriend encouraged me to do this and said she would help me.

While considering that, I thought that I could combine my crossdressing with an actual costume and go there as a female character.

It would add an extra layer of context to the whole situation. It made me feel safe and confident enough to give it a try.

3. Coming up with the costume

What I had to do now was to decide upon my costume.

I had considered a few movie and videogame characters, but I wouldn’t have time to make a good costume.

But then, while gathering my makeup supplies, I remembered something.

Two years ago, I worked for a telemarketing company that hosted a Halloween party.

I went there dressed up as a Pirate and still had that one costume in my closet.

I found and made a few changes to it so I could dress up as a female pirate.

What I did was to change the male T-shirt for a female one that could hide my shapewear, and then I got rid of the trousers.

Instead of them, I decided to use a pair of feminine shorts and sheer black pantyhose.

And, of course, the brown boots gave place to my black flats.

After that, I also managed to fit my pirate hat on top of my long brunette wig.

The costume itself was ready, and my girlfriend did my makeup, feminizing my face.

4. How things turned out

When my aunt arrived to give me and my girlfriend a ride, I was just finishing getting ready.

But I hurried up, and we got there in time.

My girlfriend went as Wanda Maximoff, from the Avengers, and stood at my side as we arrived.

As we entered my cousins’ house, my relatives were speechless for a while, as they didn’t recognize me at first.

I didn’t try to feminize my voice that day, as it would give them hints that I crossdress often.

So once I greeted them, they knew it was me.

What I can say is that things turned out better than I could imagine.

They were surprised by how much effort I had put into that costume.

But they liked it and didn’t judge. Of course, there were a few playful comments about my looks, but no signs of transphobia or discrimination.

The best part, however, was when some of my cousin’s friends arrived.

At first, they had no clue I wasn’t a cis girl. And even after I introduced myself, they treated me with feminine pronouns.

As a result, I know that my family is more likely to respect me if I ever come out as trans, and I shouldn’t be so afraid of them finding out.

It’s hard to foresee how people close to us may react to us dressing up as the opposite gender.

To have a clue, you may try crossdressing on special occasions and holidays, such as Halloween or the Brazilian carnival.

It provides you with easy excuses and allows you to see a glimpse of their reactions.

Besides that, the experience may help you overcome gender dysphoria and boost your overall self-esteem.

Have you tried something similar? If you have, please comment and describe your experience below!