X
Hey, lovelies.
When we first dip into crossdressing, it’s an emotional whirlwind. There’s excitement, curiosity, a little taboo. It’s thrilling—especially when it’s secret. But that connection? It changes. Or at least, it did for me.
In the beginning, crossdressing was a rush. The thrill of stolen moments. Hidden panties. The jolt of doing something “forbidden.” It felt sexual. It felt sneaky. It felt powerful. But slowly, that changed. The secrecy faded—and what remained was something more honest, more personal.
Note from Michelle:
This post originally appeared on my old blog, Crossdresser Chronicles. I’ve moved it here because it still reflects an important part of my journey. Some details may be out of date, or lightly updated to fit where I am now.
👉 Read more about why I brought these posts over.
From Taboo to Truth
Like a lot of us, I started with the thrill. Sneaking clothes. Getting off. Hiding it. It wasn’t glamorous—it was messy, awkward, and shame-laced. But even in those early days, something inside me clicked. That fabric, those shapes—they made me feel more like myself.
Eventually, I started to see dressing not as kink but as expression. Wearing women’s clothing connected me to a side of myself I didn’t have words for yet. It wasn’t just crossdressing—it was aligning.
If you’re in this phase, you might also enjoy how I balance crossdressing with everyday life. It’s a different kind of thrill—one that lasts.
Still on the Path
I’m not 100% there yet. I still have doubts. Still get nervous. Still wonder what it means. But I’m further than I used to be. That’s what matters. If you’re in the thick of it, don’t rush. This isn’t a race. It’s a transformation—and those take time.
And If It Doesn’t Change? That’s Okay Too.
Let’s be honest: not everyone moves past the thrill. Some people crossdress only for sexual release. Or the secret. Or the power. And that’s perfectly okay. Seriously.
There’s no “evolved” form of crossdressing. No higher plane you have to reach. If your connection stays physical or erotic—own it. There’s nothing wrong with that. This journey isn’t a competition.
Expression, Not Permission
Once I felt safe enough to really explore, things started shifting. It wasn’t about hiding anymore. It was about becoming. Dressing like a woman didn’t feel like pretending—it felt like honesty. Not fantasy. Me.
If you’re hitting this stage, you might also relate to how I first embraced femininity. That shift? It’s scary—but it’s real.
Wherever You Are—It’s Enough
Your emotional connection might shift over time. Or it might not. You might chase the thrill forever. You might outgrow it. You might find something softer, deeper, and more you.
Every stage is valid.
💬 Let’s Talk:
Has your emotional connection to crossdressing evolved? Stayed the same? Do you feel more seen or still in hiding? Drop a comment—or message me privately. We’re in this together, babe. 💜
1 Comment
Amanda · July 9, 2025 at 2:15 am
Reading this post made me think! In my first forays into CDing back in the mid 1970s when my mother’s wardrobe was my portal into the feminine world, dressing sessions always ended with the predictable sexual reaction, immediately followed by guilt. It felt amazing up to the point of climax and then, once things had died down so to speak, awful. Of course, given the amount of hormones racing round one’s body during puberty, anything vaguely to do with the opposite sex and sexual is going to evoke a similar response. The problem in my case was that the guilt of being what I saw as a pervert persisted long after the sexual aspect had waned although I didn’t realise this for a long time and avoided going anywhere near anything that I felt could trigger things and potentially cause embarassment if others were around.
The thing is, though, I now realise that although there was a strong sexual element (and to some degree there still is because whilst I don’t experience any sort of physical arousal these days, emotional arousal remains strong), my CDing was never about that and, in fact, it was an inconvenience given that it brought the whole thing to an abrupt end with little warning and the risk of soiling my mother’s clothes.
What has changed is my outlook. For a long time, it was just about the clothes and a very private thing; nowadays, I enjoy being out and about and experiencing life from a female perspective (as much as a male ever can and I would never dream of trying to declare that I know what it’s like to be a woman because I feel like one today).