After college, I wanted to disappear for a bit—not in a dramatic way, but enough to start over somewhere new. So I moved out of state, got a job in my field, and for the first time ever, I was living alone. No one knew me. No one expected anything from me. And that quiet anonymity gave me something I never really had before: the freedom to start crossdressing in secret.
Living Alone and Letting Myself Try
Once I got settled into my apartment, I started budgeting a little from each paycheck—maybe $20 or so—for building a small wardrobe. I mainly shopped at the Goodwill on the opposite side of town (obviously). I wasn’t about to risk running into anyone. Occasionally, I’d order from Amazon if I needed something more specific—wigs, breastforms, whatever I didn’t dare buy in person.
I don’t remember my exact first outfit, but I remember how it felt. And honestly? It looked awful. I wasn’t cute. I was clumsy and uncoordinated and definitely looked like a guy in a dress. But it didn’t matter.
Because I felt amazing.
What Crossdressing in Secret Looked Like for Me
Dressing became part of my daily life, quietly and privately. After work, I’d come home, change, and just exist.
I’d cook dinner. Do the dishes. Watch TV. Play video games. Sometimes I’d just look at myself and think about how I could be cuter or prettier or more… something. I didn’t know what I was chasing. I just knew I needed it.
It wasn’t about sex. Dressing didn’t turn me on. Sure, I had sexual moments while dressed sometimes—but the dressing itself wasn’t the kink. It was comfort. It was quiet. It was me, just trying to feel okay.
Yes, I Was Scared—But I Planned Around It
I was scared someone might find out. Especially at work. But I was also really smart about it.
I kept everything in a big plastic storage container next to my desk. The top one had computer stuff—controllers, wires, old games—so it looked normal. Most people would assume the second one was more of the same.
I didn’t really have a whole “clean-up” ritual. It wasn’t emotional whiplash when I changed. But I did usually feel sad that I had to. Sad that I couldn’t just stay dressed all the time. And no, I never left the apartment dressed. Not once.
Crossdressing in Secret Helped Me Learn What I Liked
This was the first time I actually started learning. I tried new fabrics, colors, cuts. I bought skirts and dresses. Bras and tops. I wasn’t just experimenting—I was exploring. Testing what made me feel good. What made me feel pretty. What fit my body and my brain.
I even started to care about how I looked. For the first time in my life, I wanted to take care of my appearance. I hated my facial hair and became obsessed with keeping it gone. I wanted to look nice—even if I didn’t know how to make that happen yet.
The Shame Was Still There, Even If It Felt Right
I could finally admit it to myself: I was a crossdresser. And I wanted to be one.
But I still felt like it was wrong.
There was this constant undercurrent of guilt—like I was doing something I wasn’t supposed to. I didn’t hate myself the entire time, but the shame crept in often enough to remind me that I wasn’t “normal.” That something about me was broken. Or at least, that’s what I believed then.
This Was the Moment Everything Started Changing
Looking back, crossdressing in secret was absolutely a turning point.
It was the first time I truly acknowledged this part of myself. Even if I didn’t have the words for it yet. Even if I didn’t see myself as trans or think of “Michelle” as a real person. I was doing more than dressing up—I was starting to understand that this meant something.
Even if I didn’t know what that was.
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