100 Questions To Ask a Crossdresser

When I first started exploring my identity as a sissy, I had no idea where it would lead me. At the beginning, it was all very quiet—private moments in front of a mirror, slipping on something soft and feminine, and feeling butterflies I didn’t fully understand. It wasn’t just about clothes. It was about how they made me feel: submissive, pretty, playful, and completely myself.

As I grew more comfortable, I began to realize that being a sissy wasn’t just about dressing up—it came with desires, feelings, and, yes, fetishes that I had never really allowed myself to explore. And the more I explored, the more I understood myself—not just sexually, but emotionally too.

So, what are my fetishes as a sissy? Well, I’ll be real with you. Some of them surprised even me.

1. Sissy Lingerie and Feminine Clothing

This was my first and deepest fetish. I can’t overstate how powerful it feels to wear silky panties, thigh-highs, or a lacy bra that fits just right. For me, it’s not just about looking feminine—it’s about feeling vulnerable and soft. The way certain fabrics hug my body, the way I move differently in heels or a skirt—it all turns me on like nothing else.

And there’s something incredibly arousing about being dressed up and knowing I’m not supposed to be. That contrast, that taboo, makes it even more exciting.

2. Submission and Control

This one took time to admit, but being a submissive sissy is a huge turn-on for me. The idea of giving up control, of being told what to wear or how to serve, taps deep into my fantasies. I’ve always craved someone strong who enjoys taking the lead and molding me into what they want.

Whether it’s being called cute names, doing chores in a maid outfit, or being given tasks to complete—submission brings me pleasure and purpose.

3. Humiliation (the Fun Kind)

Now, this isn’t for everyone, and I’m not talking about being truly disrespected. For me, playful, consensual humiliation is incredibly hot. Being teased about how girly I look, or being told I make a better girl than a guy—those things light me up.

It’s about the roleplay, the power dynamic, and the feeling of being exposed. There’s a thrill in being “put in my place” as a sissy, especially when it’s done with a wink and a smile.

4. Chastity

I discovered chastity a little later, and at first, I wasn’t sure it was for me. But once I tried it, I understood why it’s such a big fetish in the sissy world. Giving up access to my own pleasure—having someone else control when (or if) I get to release—it felt frustrating, exciting, and insanely erotic.

It made everything more intense. Every brush of silk, every glance in the mirror, every tease… it was amplified because I couldn’t finish. It turned into a kind of mind game that made me feel owned, trained, and obedient.

5. Being Seen

This one surprised me the most. I used to think all my sissy play had to be private. But over time, I started fantasizing about being seen—not necessarily by strangers, but maybe online, or with a partner. Posting a pic, wearing something femme outside under my clothes, or being subtly dressed around others gave me a secret thrill.

It’s a fetish tied to confidence, risk, and validation. Knowing someone might look at me and see the real, pretty, slutty side of me? That’s a turn-on all by itself.

Final Thoughts

Being a sissy isn’t just a label for me—it’s a whole part of my identity that I’ve learned to explore without shame. My fetishes help me feel alive, excited, and true to who I am. They’re not just about sex; they’re about expression, joy, vulnerability, and release.

If you’re on this journey too, my biggest piece of advice is: go at your own pace. Let yourself be curious. Don’t judge what turns you on. This world is full of layers, and every layer you uncover brings you closer to your real, raw, beautiful self.

Fetishes don’t make you dirty or weird—they make you you. And that’s something to be proud of.