My Journey as a Genderfluid Crossdresser

What does it mean to be a crossdresser? How to deal with it? Well, it’s a very personal experience, unique to each one of us. As such, we may come across several definitions, based on how certain people experienced their journeys. The many different stories give us an idea of how our journey may turn out. So, with that in mind, I’m about to share mine with you.

I’ll talk about how I’ve found myself to be a crossdresser, and what I did after that. I had some struggles, and still do, but it’s a price worth paying. I’m not completely open about it, but the people that matter already know about it.

By telling you about my journey, I want to encourage you to keep up with yours. It’s been a mostly positive experience so far. And I want yours to be so as well.

1. How did I discover

I guess I knew that from an early age. Even as a kid, I wondered what it would be like to be a girl. I went as far as to put on a pink wig and some girly shoes that belonged to a friend of mine. I remember that every single time in which a movie depicted a cross-dresser, I thought to myself: “I wish I could do that”. However, I used to repress these feelings, both for shame and fear. But of course, I never forget them.

As society became more tolerant, it became more common to hear people talking about cross-dressers and trans people. It was quite natural to acknowledge and respect them by then, at least in my country. Discrimination saw a major drop during the early 200’s around here, but it didn’t vanquish. So it wasn’t until my teenage years that I had the courage to google these terms and learn more about them.

2. How did I deal with it?

At first, as I said, I used to repress my desire to crossdress. But sometimes I just couldn’t help it and had to find a way to try a few things. However, I didn’t do too much back then, as I was always afraid of the still existing discrimination. All I did was try on a few bras and use apps to gender-swap some selfies. But that doesn’t mean that I was in denial, I knew I wasn’t a cis guy. So I spent hours on the internet watching makeup tutorials and reading crossdressing guides.

Another useful thing I did, was to lways with other crossdressers online. Even though I did that anonymously, I felt part of something. The queer community online is quite inclusive and supportive. It’s always welcoming new members with useful tips and orientations. It gave me hope, as I believed this dream would come true someday. And it did.

3. Coming out

I came out even before I started to crossdress. It was a few years ago. I’ve been dating a girl for about a year and a half. I knew that, if I wanted to maintain that relationship, I couldn’t keep such a secret from her. But I didn’t know what to tell her either, so I decided to start preparing her first. I started by talking about cosplay, as that’s an activity we both enjoy, and mentioned a few female characters I’d like to dress up as for some events. She was okay with it, which was a good sign.

A week later, I’ve decided to tell her, but first, I had to figure out who I was. And after careful consideration, I found myself to be a transfeminine gender-fluid person. And that’s exactly what I told her when we met that night. She couldn’t be more supportive, and I regret nothing! I wasn’t expecting such a good reaction, with her giving me ake-up tips and even helping me to choose my feminine name. Months later, I told my sister as well, and she let me borrow her ake-up supplies as well.

4. Starting to crossdress

Once I told my girlfriend about my gender identity, she was quite excited to help me dress up in girl mode. We bought a few things online and went downtown to shop for clothes. Once everything arrived, she did my makeup and took some pictures of me as a girl. It was a rather joyful experience, and from then on she always supported me.

As time passed, my cross-dressing routine became more complex, and I bought new wigs, shapewear, and even fake silicone breasts. All that effort made me more passable within each session. It took time, and I’m still perfecting my abilities. But every time I look back, I’m glad I dared to start, and I’m happy for all the way I’ve come. Sometimes, all it takes to achieve happiness is a little push forward.

5. Talking to my parents

During the covid 19 pandemic, my college had suspended classroom lessons and we started to take remote classes. Besides that, my landlord ended our contact, as he wanted to go back to the apartment I was renting. So I had to go back to living with my parents and take my cross-dressing stuff with me. During these years, my cross-dressing wardrobe grew larger, and my routine became even more intense. I knew I couldn’t hide it from them much longer. So I had a conversation with my girlfriend, and we decided it was time to come out to them.

I wrote a lot of stuff describing different gender identities and explaining to them who I am on the inside. I made it as didactical as possible, with illustrations and a picture of me as a girl. Nonetheless, they were still quite shocked and things took some time to go back to normal. But they still love me, and respected me, even though it’s still hard for them to fully accept it.

As respectful as they were, they still had me agree upon a few things. They told me not to tell it to the amily the amily just yet, as we have quite a big one and don’t know how each member will react. And they also asked me to avoid dressing up during the day, as they preferred not to see me doing that. And I agreed since I didn’t want any conflict and was glad they were comprehensive.

6. The difficulties I came across

I can argue that my journey so far has been quite easy, in terms of comprehension and acceptance. But as every cross-dresser, there are a few things that unsettle me and impose difficulties upon my cross-dressing habits. First of all, I want to talk about my girlfriend’s parents, which are extremely religious and full of prejudice against trans people. Both I and my girlfriend know that if they found out, they would be against our relationship, making things way more difficult. I have to be extra careful around them, avoid using my feminine name, and hide any pictures of myself. Due to that, our plan is for me to avoid coming out to them until we’re married. And after that, we plan to go live somewhere else if they don’t accept it.

I also suffer a lot from body dimorphism, as most trans people do. Being 1,80 meters tall (5’9 feet), and weighing something around 100kg (220 Lbs), I’m not exactly very feminine. I’m a bit chubby, with a square frame and little curves. It’s about average for a man, but still far away from feminine beauty standards. My voice also bothers me, but I manage to overcome that with intense voice training. I’m trying to get rid of some weight to define my waist and get some curves, but I can’t go to the gym every day. All I can do for now is to count on a variety of shapewear gadgets and hope to start HRT this year.

Speaking of hormones, I guess I may address another ongoing problem. It’s difficult to find medical aid where I live, so I’m waiting until I go back to college to start it, as it’s in a bigger city. But there I’ll have more expenses, and affording the hormones may not be so easy. I hope that once I start, I manage to achieve a more androgynous or feminine frame.

This has been my journey as a gender-fluid cross-dresser so far. I’m still learning, but I like to share my experience with those who are just beginning. I was afraid as well, but everything turned out better than expected. I have come across some difficulties, but most of them are either due to personal problems or can be dealt with. Sometimes, all we need is a bit of confidence. And by sharing this story, I expect to bring hope to our sisters out there, making them more confident. It ends on a positive note so far, and hope yours will as well. Have you got a story of your own to share with us? let us know in the comment section down below!