Crossdressing in college was the first time I did it on my own terms—even if I didn’t call it that yet. If high school was about stealing panties in secret, college was when I started buying them. That shift might seem small from the outside, but for me? It changed everything.
Why I Started Crossdressing in College
When I moved away to school, the people I used to steal panties from weren’t in my life anymore. And honestly? That was probably for the best. I didn’t have immediate access to panties the way I used to. So if I wanted to keep wearing them, I had to make a choice.
And I did.
I walked into Walmart, terrified out of my mind, and bought my first pack.
Buying Women’s Panties as a Guy Was Terrifying
I didn’t know sizes. I didn’t know what fabrics I liked yet. I just grabbed a multipack—probably Hanes Her Way or Fruit of the Loom—and rushed to the checkout. I didn’t look anyone in the eye. I just wanted to get it over with.
The panties were too small. I had no clue what I was doing. But they were mine. They were soft. Practical. Kind of cute.
And they felt right on my body in a way nothing else ever had.
My Routine Crossdressing in College
Most of the time, crossdressing in college meant panties. Simple ones. I wore them to class, to study, to walk across campus. They weren’t a fetish anymore. They were just… underwear. My underwear.
I kept them hidden in an old headphone box in the back of my desk drawer. Every now and then, I’d sneak in a new pair or two when I had the nerve to shop again.
There was still a thrill. Not sexual—but definitely emotional. Like I was doing something “wrong” and choosing to do it anyway. That small rebellion became a private source of strength.
Roommates, Secrets, and a Girlfriend Who Found Out
I had roommates all four years. The first year, there were three of them (long story). The rest of the time, I lived with the same guy. As far as I know, he never knew. Or at least never said anything. No one ever found out.
Well—except one person.
During a “sleepover” with a girlfriend, she saw the waistband of a pair of panties while I was getting undressed. She didn’t freak out. Just raised an eyebrow, said it was a little weird, and moved on. Didn’t seem to bother her. We actually stayed together for quite a while after that.
I still think about that moment a lot. Not for the drama, but because it was the first time someone saw that part of me and didn’t freak out.
I Didn’t Want to Be Seen Crossdressing in College
A lot of people fantasize about being caught or accepted. That wasn’t me. I didn’t want attention. I didn’t want anyone to know. I just wanted to wear what felt good—and be left alone.
Most people don’t see your underwear anyway. I just wanted the freedom to enjoy mine without shame.
But the shame was still there. I felt guilty almost every time. Even though it wasn’t sexual. Even though it was just soft fabric and color and comfort. It still felt like I was breaking some unspoken rule.
And I guess… I was.
The Skirt, the Game, and the Quiet Joy
By my third year, I bought something different: a houndstooth pleated skirt. It was cute, flowy, and made me feel amazing. But I only wore it when my roommate went home for the weekend. Always in secret. Always with the blinds closed.
Most of the time, I’d pull it on and just sit at my desk playing World of Warcraft. No makeup. No photos. Just me, in a skirt, running dungeons and feeling… comfortable. Peaceful, even.
There was nothing overtly feminine about how I acted. I wasn’t trying to look like a girl. I just liked how it felt. I needed to feel that softness, that rightness, even if only for a little while.
Crossdressing in College Was Quiet—but It Mattered
I didn’t call it crossdressing at the time. I didn’t think of myself as transgender. I didn’t know what any of it meant. But I was still doing it. Still choosing it. Still reaching for something I couldn’t yet name.
Looking back, it’s clear this was the start of Michelle.
Not a full wardrobe. Not a bold transformation. But a few choices that shaped who I’d become. A few pieces of clothing that whispered, “Hey, this might be who you are.”
Even if I couldn’t say the words, my body knew.
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