X
Hey, lovelies.
I didn’t have a lightbulb moment when it all started. No big epiphany, no spark of “I’m a girl.” Just… signs. Small ones. Quiet ones. The kind that build up until one day you look back and go, “Oh. Yeah. That makes sense.”
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 Some details may be out of date, or lightly updated to fit where I am now.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.
The Early Years: Why “Girl Things” Just Felt Right
Growing up awkward and out of place, the girls were always easier to be around. I loved their energy. I loved their kindness. And I loved doing the things they did. I wasn’t trying to be one of them—I just felt more like me when I was near them. I even went prom dress shopping with friends once. I gave feedback, laughed, and yes… tried one on. It should’ve been humiliating. It wasn’t. It felt weirdly right.
If you’ve ever felt like that, you might relate to how I blend femininity into my day-to-day life. The shift doesn’t always start with gender. Sometimes it starts with belonging.
Middle School Cringe and Secret Panties
Okay, deep breath: I used to steal panties. Cringe? Yes. But it’s my truth. I didn’t have words for what I was doing—I just knew the fabric, the softness, the contrast from my own clothes—it thrilled me. It started out sexual. But that changed.
By college, I was buying my own. Wearing them under regular clothes. The secret wasn’t about kink anymore—it was about comfort. And it made me feel quietly powerful.
Dressing for Me, Not for Them
When I finally bought women’s clothes around 25, it blew my mind. The fabrics. The silhouettes. The way they made me feel like me. And yet, I still felt like a freak. Even alone in my apartment, wearing a skirt made me question everything. Not because it felt wrong—because it felt too right, and that scared the hell out of me.
Marriage, Secrets, and Slowly Coming Out
I didn’t tell my wife at first. Not because I didn’t trust her—but because I didn’t trust myself. When she eventually found out, yeah… there was some discomfort. Some confusion. Maybe even a little disgust. But what hurt her most wasn’t the crossdressing—it was the secret. And honestly? I get it.
She’s not fully supportive, but she’s not cruel. She lets me have my space. She asks that I don’t dress in front of our kids. And I respect that. They’re still young, and the world isn’t exactly gentle about this kind of thing.
If you’re in a similar spot, here’s what I wish my wife knew. You’re not alone.
Feminine Freedom in Secret Moments
Now, when the house is quiet, and I’m alone, I get to explore. Not in a fetishy way—just… real exploration. A skirt. Some makeup. My favorite blouse. It’s not “playing dress-up.” It’s becoming.
For the first time in my life, I feel safe enough to explore who I really am. Crossdresser? Genderfluid? Maybe something more? I don’t know. But I finally get to ask those questions without shame eating me alive.
Masculine Outside, Femme Inside
“Boy mode” still pays the bills. But I’ve started blending femininity in—fitted jeans, makeup practice, soft touches in my wardrobe. A pea coat. A little eyeliner. A vibe. Like a closeted gay guy from the ’90s. And you know what? I’m okay with that.
I’ve been working hard to feminize my body—walking 10,000 steps a day, strength training to build curves (as best I can without HRT), and diving deep into diet and nutrition. I’m counting calories, watching macros, and even incorporating more phytoestrogen-rich foods to support a more feminine shape. It’s been intense, but honestly? I’ve never felt more in control. And for a little daily boost, I wear this Maidenform waist cincher under my clothes—it adds just enough shape to make me feel like her.
I’m Still Figuring It Out (And That’s Okay)
I don’t have all the answers. But I don’t need them yet.
This is the start of something. Something tender. Something powerful. And if you’re reading this and nodding along? Then maybe it’s the start of something for you too.
💬 Your Turn:
Did your journey start small, like mine? What was your “first time”? Let’s talk in the comments. Or message me—my inbox is always open for sisters like us. 💜
0 Comments