My Crossdressing Memories (First Times)

What memories do you still have of your crossdressing journey? For me, my first day of crossdressing was an experience that I will never forget. I was 13 years old and was getting interested in feminine clothing. So, one day, when my parents were out of the house, I decided to raid my mom’s closet.

I remember feeling so excited as I rummaged through my mom’s clothes. Just couldn’t believe that I was actually going to do it! I knew that crossdressing was something that I had always been interested in but hadn’t tried yet. But now that my parents were out of the house, I felt like I had the perfect opportunity to try it out.

I finally settled on a simple outfit: a white blouse, a black skirt, and a pair of heels. I remember feeling so grown up as I slipped into the heels. It made me feel sexy and confident. The rest, as they say, is history! But I’ll tell you more about it.

1. The excitement of buying my first piece of clothing

This is one of the memories that I will always cherish. I remember the feeling of excitement when I was finally able to buy my first piece of clothing. It was like a dream come true.

I had just finished high school, and I had started working at a clothing store. I had always loved dresses, but I never had the chance to wear them because I was afraid. One day, I saw the most beautiful dress in the store, and I knew that I had to have it. I didn’t care about the price tag. So, purchased it.

It fit me perfectly, and I felt like a million dollars. That’s when I realized that crossdressing was something that made me feel really good about myself. Since then, I wanted to be a crossdressing sister.

The experience was so exciting that it made me want to buy more clothes and experiment with my style. I expressed myself in a way that felt true to me. And I loved every minute of it!

Of course, I didn’t break the news to anyone at that moment. I knew that I had to keep it a secret for a little while longer. But the feeling of finally being able to be myself was exhilarating. And I knew that there was no turning back now.

I even remember bumping into one of my classmates, and she was also getting some dresses in the same store. I lied that I was just helping my sister pick out a dress. She noticed the dress looked larger for my sister. And for a moment, I thought she was going to expose me. But thankfully, she didn’t, and the secret was still safe.

Eventually, I did come out to my family and friends as crossdresser. And they were all very supportive of me. But that experience of buying my first piece of clothing will always be a special memory for me. Because it was the moment when I finally allowed myself to be who I really am. And I am so grateful for that.

2. The thrill of trying on new clothes and makeup

Another one of my favorite memories is the thrill of trying on new clothes and makeup. I remember when I first put on a dress. It was so different from anything I had ever worn before. I felt like a princess, and I loved it. Since then, I’ve always enjoyed dressing up and experimenting with different styles. 

Liked I mentioned earlier, the first time I tried feminine clothes was back when I was 13 years. It was a day when my parents were away, and I decided to raid my mom’s closet. For sure I knew if she found out, she would be so mad, but I just couldn’t resist.

I put on one of her dresses and a pair of her high heels, and I felt like a completely different person. I felt so feminine and beautiful.

Since then, I’ve always enjoyed dressing up and experimenting with different styles. I love finding new clothes and makeup that make me feel good about myself. It’s always a fun adventure for me.

As for the makeup, I first tried it out when I was 17. I had been curious about it for a while, but I was too scared to try it. I didn’t want to look like a clown or something. But one day, I decided to just go for it.

I started with some simple things like foundation, mascara, and lipstick. I remember feeling so good about myself when I saw how my face looked with makeup on.

Since then, I’ve always enjoyed wearing makeup and trying new looks.

3. The anxiety of going out in public for the first time as a crossdresser

Of course, not every memory is a happy one. I also remember the anxiety of going out in public for the first time as a closet queen. I was so scared that someone would recognize me and make fun of me.

But I didn’t let that stop me. I knew that I had to be true to myself, and so I went out in public anyway. And you know what? It was actually really liberating. I felt like I could be myself for the first time in my life.

It was a sunny morning, and I remember feeling the warmth of the sun on my skin as I walked down the street. I felt so alive and free. And I realized that this was just the beginning of my journey. There was so much more to discover about myself, and I was excited to explore it all.

Now, looking back, I can see that that moment was a turning point in my life. It was the moment when I realized that I could be myself, no matter what others might think or say. And it was also the moment when I decided to start living my life for myself instead of trying to please others. Felt scary, but was worth it.

4. The joy of feeling beautiful and feminine

This is one of the memories that haven’t escaped my mind. Although I had been crossdressing for a while, there came a time when I felt extremely beautiful and feminine. It was a strange yet wonderful feeling.

I had been out shopping for clothes with my sister, and we ended up in a lingerie store. I had never really thought about lingerie before, but something about the pretty lace and satin caught my eye. My sister was picking out some things for herself, so I decided to browse the racks as well.

I found a slip that was just my size, and it was such a pretty shade of pink. I had to try it out. As soon as I slipped it over my head, I felt different. It was like I had transformed entirely. I felt beautiful and feminine, and I loved it.

I ended up buying the slip. But being a “man”, I was too embarrassed to wear it in public. So, I would only put it on when I was home alone. I would parade around my apartment, feeling like the queen of the world. It was wonderful.

5. The courage to come out to my friends and family

The first time I gathered up the courage to come out to my friends and family was honestly one of the most terrifying but also liberating moments of my life. I was scared that they would reject me or that they wouldn’t understand.

It felt great to be able to be myself around the people I love, and I’m so grateful that they accept me for who I am. This moment gave me the strength to continue living my life as a crossdresser, and I’m so thankful for that.

6. The peace of being accepted for who I am

When my family finally accepted me as a crossdresser, that was a moment I will never forget. I had informed my sister about my feelings toward crossdressing, and she didn’t seem quite pleased at first.

Being her only brother, I guess she was worried about what other people might say or think. But my family accepted me for who I am. It was the best feeling in the world.

My dad was also reluctant at first. He would ask me why I wanted to crossdress and if I was sure that this was what I wanted to do. I think he was just worried about me and didn’t want me to get made fun of by other people.

The memories of my crossdressing journey remain etched on my mind. Every time I dress up, I feel an immense sense of joy and satisfaction. Crossdressing has helped me become more confident and comfortable in my own skin.

It all started when I was just a little boy. I would always sneak into my mother’s closet to try on her clothes. I loved the way they made me feel feminine and pretty. As I grew older, I began to experiment with makeup and hairstyles. I loved transforming myself into a beautiful woman.

All the first-time memories are crystal clear, and I treasure them to date. Which memories of your crossdressing do you like to share?