An Interview With Natalie: Insights From the Crossdresser Community

In the crossdressing community, so many of us feel like we are alone. We never really see people presenting like us. Yes, there are drag queens and trans women who are more in the spotlight, but there are plenty of crossdressers out there, too; we are just hiding! This interview blog series that I am working on is to help uncover more stories of crossdressers to help us all feel like we are just one of many in this world.

The first interview of the series I will introduce you to is Natalie! Natalie is a 27-year-old crossdresser from New York. She has always had a love for women’s clothing and accessories. She has been dressing for about 15 years now and, on average, gets to dress about 2-3 times per week currently. Outside of the crossdressing lifestyle, she also loves sports and hanging out with friends and family.

If you would like to find Natalie on social media, her Reddit is u/Natalie-NY and her Instagram is natalieee_015. Please enjoy getting to know Natalie through the series of questions that I asked her!

Meet Natalie

Catie: What would you say that your “role” is in the crossdressing community? How do you identify yourself?

Natalie: I have not fully figured out yet how I identify. I am a crossdresser, but it may be deeper. Sometimes, I do say I am gender fluid or by gender. I enjoy my day-to-day male life, but I love being a female equally as much.

Catie: How long have you considered yourself a part of the crossdressing community?

Natalie: I started dressing when I was about 12 years old. Curiosity got the best of me, and I tried on a dress that my sister had lying around. Instantly, I was hooked. At the time, I didn’t even know what crossdressing was; I just knew I enjoyed wearing girls’ clothes. This would continue throughout the years, and as the internet started to become a larger part of my life, I discovered the drag and crossdressing community. This increased my desire to dress and was the beginning of my true journey into crossdressing.

Is It Sexual? Or Just About Feeling Pretty?

Catie: Do you consider your crossdressing lifestyle as sexual? Or do you enjoy it for other reasons?

Natalie: At times, yes, there is a sexual aspect to my crossdressing; however, I do not consider it the main factor. I enjoy the way I feel and look when fully dressed. There is no better feeling than taking the time to choose an outfit and accessories, and looking in the mirror when I am done. Over the years, I have become more and more comfortable wearing girls’ clothes. It just feels natural to me at this point. I believe that as I have gotten more comfortable and embraced this side of myself, it has also allowed me to discover and embrace the sexual side I feel as a woman. I look forward to continuing to learn and experience more of this.

Catie: What was the main thing that got you hooked about crossdressing?

Natalie: I am interested in women’s clothes. Growing up, I would admire my sister’s and friends’ outfits and wonder what I would look like wearing them. Still, to this day, I have an eye for cute outfits and use other girls as inspiration for the style that I have developed. Once I started being able to try on full outfits, I never looked back, and I was hooked.

Catie: Can you explain in more detail about the main thing about crossdressing that you enjoy?

Natalie: I love the transformation process and how I essentially feel like a different person when I enter girl mode. The way I move and talk changes. While I do love my day-to-day male life, there is no better feeling than putting that side away and embracing the feminine side that I have come to love. Of course, the clothes are great too. The endless styles to try, the jewelry, and the makeup. One of the best parts that I had no idea would happen is the friends that I have made. I have been so fortunate to talk online with other crossdressers and have come to make so many great friends who have also been through the same things as me. The way we can relate to each other has helped me so much in my journey, and I feel like it is only the beginning.

Acceptance From Yourself & Others

Catie: Have you fully accepted that you enjoy this lifestyle and that it is a part of you?

Natalie: I have 100% accepted this lifestyle, and I know it will never go away.

Catie: To follow up on the above question, does anyone else in your life know that you are involved in this lifestyle?

Natalie: No one in my life knows. It is a secret I keep from friends and family, which does at times cause a lot of anxiety. It is not that I am ashamed of it; I am unbelievably proud to be part of this community. But, for the time being, it feels easier to keep this side of my life separate.

Crossdress Essentials & Goals

Catie: If you could only have one crossdressing item for the rest of your life, what would it be? Use details to describe why!

Natalie: Wow! What a difficult question. It has to be panties. For me, once I put them on, I instantly enter girl mode; it’s like a switch is flipped. Over the years, due to privacy issues, my time to dress has been limited. Fortunately, I do not have this issue as much currently. But during those times, I would have a strong desire to dress, but just be unable to due to privacy and time constraints. I would wear panties as much as I could, and I still do to this day. Even though no one can see them, it helps me enter my feminine mindset. I could not live without panties, LOL.

Catie: What are your goals with your crossdressing lifestyle? Short-term and long-term.

Natalie: My short-term goals are to continue to dress as often as possible and to learn how to do my makeup properly. When I look back at old pictures, I see how much progress I have made, and I am excited to keep learning. Long term, I would like to get myself out in public. I hope to be able to turn my internet crossdresser friends into real-life friends. I see myself going shopping, getting my nails done, and going out to bars and restaurants in girl mode. The hope is that this would also allow me to expand my friend group and meet more people who accept and support this side of me.

Story Time!

Catie: Please pick your favorite personal story about your time within the crossdressing space and write a paragraph (or more) about it!

Natalie: A couple of months ago, I had my favorite experience ever in my crossdressing journey. As mentioned, I have a lot of internet friends. One in particular is local, and we had been talking about meeting and hanging out for over a year. It is difficult to plan as we both keep this a secret in our lives, but we were able to make it happen.

We went to a shop that specifically does makeovers for crossdressers, and we got our makeup done. Afterward, we rented an Airbnb for the day and had the cutest girls’ day ever. This felt like such a huge step for me, as I had wanted to experience being in girl mode around other people for so long. I am so grateful for this experience, and I do hope I am able to build on this to start achieving my long-term goals.

Advice From Natalie

Catie: What is some advice you would give to another person with the same crossdressing interests as you?

Natalie: My biggest advice to someone new to the crossdressing world or someone who struggles with accepting this side is to take your time. The look and mental/emotional side do not happen overnight. It has been a journey of ups and downs, but I am so happy with where I am right now. It is easier said than done, but also don’t purge! There may be times when you’re just not feeling your feminine side, and that is totally okay.

When that happens to me, I just put my clothes to the side and live life. Eventually, the feeling comes back, and I am ready to jump right back into it. One of the things that has helped me the most is talking to other crossdressers. Learn each other’s stories helps you realize that there is absolutely nothing wrong with doing this, and there are so many other people who have the same thoughts, struggles, and successes. I am so proud to be part of the crossdressing community, and I look forward to the new experiences that it will bring for me.

Catie’s Final Thoughts

I loved being able to ask Natalie these questions and get her perspective on her life as a crossdresser! I have been talking with Natalie for a few months now, and I can say she has been a great friend to me in the crossdressing space! When I wanted to do an “interview-style” blog post, I knew I wanted her to be my first!

She has a beautiful outlook on crossdressing and seems to have fully accepted this side of herself. I also appreciate her interest and openness to other hobbies, as we can talk about sports and random things. It makes for a well-rounded friendship! She is also super pretty, so you should check out her Reddit or Instagram pages to see for yourself!

If you are in the crossdressing space and would like to be interviewed for my next “interview-style” blog post, you may reach out to me on Reddit: u/cd_catie93 or comment on this post with your information. I would also appreciate feedback on this blog style. Let me know your positive and negative thoughts!