How Crossdressing Helps Me Discover Different Sides of Myself

If you ask most crossdressers, they will probably have a similar introduction story. From my experience meeting people or chatting with people who share an interest in dressing up, there’s usually a common Genesis story where we share a lot of broad strokes. For me, it was when the Victoria’s Secret catalog began to arrive at the house.

Like most teenage boys, I was always happy when the new Victoria’s Secret catalog arrived, but it wasn’t long before I began to realize that my thoughts about it were quite different from those of my friends at the school lunch table. While I shared my opinions with them about which models were the sexiest or who we liked the most, I also noticed that I was thinking about the lingerie in the catalog as well as the girls.

Anytime I found myself looking through the VS catalog or walking through the underwear department in a shop, I would always gaze at the bras and panties in wonder. Over time, I’ve become more accepting of my crossdressing desires, and this acceptance has helped me open some windows into myself.

Beginnings and Identity

It’s hard to say what motivated my curiosity about women’s things as a teen. But it is not hard to say what sustained it. Like many teenagers, I was interested in sex; hormones were raging, and I think every teenager gets those ideas at this time of our lives. We all become interested in our bodies, how they work, and what feels good.

I think the first thing that pulled me towards crossdressing was definitely sexual. The models in the lingerie catalogs were gorgeous, and their outfits were so sexy. Before long I had begun to be curious to try on something sexy. The boy’s clothes are all so ordinary and boring. It wasn’t long before I had a bra hidden in the back of my closet.

Unlike most dressers, I didn’t steal or borrow a bra from someone I knew. I went to a big shop and bought one. I thought the self-checkout tills would save me from some embarrassment. Getting home and trying it for the first time was thrilling. I remember getting extremely aroused and excited as I put my arms through the loops. It wasn’t long before I began to use some socks to create some boobs and so on.

I think this was the first big realization brought on by my dressing. A sexual realization isn’t uncommon. I’ve talked to a few other dressers about their first times dressing up, and getting excited isn’t uncommon. For me, this was the first clue that gender, sexuality, and attraction are spectrums or shades of grey, and the thick black lines that we like to draw between identities are false.

As I grew older, moved around the world, and made friends from all walks of life, I became more accepting of the spectrum outlook than black-and-white. Different people can be different depending on their mood or just what they want to project that day. This helped me come to terms with my fluctuating desires, either to dress up or even just a short-term dislike of a specific food.

Dressing taught me to be a bit more tolerant of myself and not be ashamed of what I liked or disliked at any given moment.

Emotional Intelligence

It wasn’t hard for me to notice that I am quite a stoic person. It’s hard for me to show emotions outwardly, and coming of age in big cities like London and New York, where a stiff upper lip is commended, it’s difficult to be vulnerable. As a result, I also grew to be a very stony character and perhaps even lacked empathy or understanding of those around me.

I’ve always noticed that women and their female friends are more able to discuss their emotions with one another and can get the validation they need from their friends. Male friendships can be but frequently aren’t like this. As a result, I tended to think practically, not emotionally, about everything. Feelings and concerns could get buried under a pile of logical advice and problem-solving ideas.

I think it was when I went for my first crossdressing makeover that I began to open up in a new role. I was so nervous and guarded when we started. However, the girl who was helping me get ready and doing my makeup was a part-time actor and acting coach. She encouraged me to choose a feminine name and maybe try to create a character to make it easier to get relaxed in a new role as a woman.

This outlook wasn’t something I’d thought of before and it does help. As the makeup was applied and I tried different femme clothes, I tried to shed my self-image and imagined I was someone new. Since then, I’ve chosen a femme name, Lisa, and tried to let her grow and figure out her interests.

As Lisa, I can feel more comfortable talking about my own emotions, and it’s easier to be naturally empathetic. Granted, when interacting with people like Lisa, it’s generally online, but I can detect a change of mindset with the change of role. I’m more interested in others when Lisa than I am in my usual existence.

It took some time to get comfortable in this mindset as a ‘character,’ but I have noticed that I’ve become more understanding and respectful of others’ emotions. Most of my friendships, especially making new friends, have become a bit easier because I am more aware of others’ feelings and potential vulnerabilities.

Shyness

I’ve also always been extremely shy around new people and in new environments. It can take a while to feel comfortable and confident enough to come out of your shell. If I do not feel totally safe in my environment and surroundings, it could be hours before I am confident enough to open my mouth. I’m more likely to silently take in what’s going on around me until I feel ready to introduce myself or show a bit of emotion. As myself in my normal day-to-day life, this has caused me a number of issues; either people get a negative first impression or are put off by my lack of a smile.

This has been an issue for me for as long as I can remember. I think it has something to do with wanting to feel safe and comfortable before taking a risk. The first time I went for a full crossdressing makeover, I was trembling as I rang the bell. It took a bit of coaxing for the stylist at the makeover student to get me to talk about what sort of look I was hoping to achieve.

Once the process started, I was so curious to learn about make-up and how to best choose outfits for my body shape that I had to ask questions. Seeing the transformation play out in the mirror in front of me made me smile and be more outgoing. By the time I had been fully made up and dressed, it felt as if I was almost a different person or a different version of myself.

That version of myself was able to open up more freely; I guess because the risk I took by going for a makeover and opening up to a stranger in a safe place was a good one. It was quick and easy to adapt to a new environment because I was sort of a new me.

The new me had only a few hours, and my urge to make the most of the time took over. After a few pointers about posing and deportment, I was really thrilled to be pretty and loving every minute. The photos from that first photo session still remind me that risks can pay off and that being ultra-hesitant can be overcome with the right mindset.

Shame

I think a lot of crossdressers start with a deep sense of insecurity about their desire to dress and guilt about enjoying being feminine. I know I felt this throughout my teens and early university years. I didn’t want anyone to know my secret hobby and how it might impact their impression of me.

After my makeovers, I left some of that shame behind. The second time I went for a makeover session, there was another crossdresser at the studio while I was there, too. We both started in different rooms, but the staff suggested we meet and take a few photos together. The other girl, a more experienced dresser than I am, immediately complimented my looks, how pretty I was, and how she was jealous of my cheekbones and legs. Being introduced to another dresser as a girl really was a bit of shock treatment for me, but the fact that someone new had seen me dressed and they were positive about it was something I hadn’t anticipated.

Going out for a walk together in the big city and not getting any dirty looks or harassment was also a sign for me. No one on the street cares what I’m doing or wearing as long as I’m not bothering or being pushy. The whole time we spent together was wonderful, and I lost my fear of being a girl in public. People have their own lives and aren’t inspecting me as I walk in girl’s clothes.

That was the first time I was out and about for a little while, all dolled up, and through conversation with my new friend, I slowly began to change my mindset. I shouldn’t be ashamed of anything that makes me feel relaxed or happy, especially if what I am doing isn’t harmful to anyone.

Relationships

Finally, accepting myself as a crossdresser has given me more of a clue to potential red flags in a relationship. Because I know myself and am accepting of myself, I am hyper-aware of any sort of judgmental outlook or critical commentary regarding someone a bit different. It’s quite surprising how, even in 2025, people can be so intolerant of an atypical identity.

I think that a potential partner’s attitude towards atypical hobbies or habits is hugely important in a relationship. Partners shouldn’t be judgmental and should be willing to embrace their partner’s full, true self. Because there is nothing wrong or illegal with my dressing, I honestly believe it should be accepted. After all, it isn’t a toxic hobby like gambling, and it isn’t a destructive pastime like drinking and partying can be. I don’t expect my potential partners to accept my girl side fully, but I do expect them not to look down on me when I decide to share it with them.

Conclusion

To finish up, I love my hobby, I love myself when dressed up, and I love being pretty. My interest and curiosity about girls’ underwear led me to discover a part of myself that I don’t think I would have any other way. I’m glad I let myself engage instead of burying it deep inside.

Crossdressing has made me more tolerant and respectful. I think I’ve become more open-minded and accepting of others. Putting on my “girl hat” makes it easier for me to be more sensitive to others and what might be bothering them. I wouldn’t trade my girly side for anything- well, maybe more dresses and skirts (smirk).