When my wife found out I was crossdressing, I expected disaster. But that moment ended up starting something bigger—a deep exploration of my crossdressing and sexuality.
Honestly? She surprised me. She didn’t embrace it—but she didn’t shut it down either. She gave me space.
Not shared, not partnered, but space to explore on my own.
And with that shame and fear finally off my shoulders, I started experimenting. Not just with clothes—but with everything they made me feel.
That’s when questioning my sexuality after crossdressing really began.
I remember thinking, “If I like the clothes this much… does that mean I might also like the things girls like? Like men?”
Heads up—this one gets into sexuality, kink, or fantasy.
I know that’s a sensitive (and sometimes taboo) topic for a lot of folks. I do my best to keep things honest and respectful, but some parts are hard to talk about without getting a little…explicit. Just putting that out there before we dive in.
Exploring My Crossdressing and Sexuality
So I tried things. Not with other people—I’ve never cheated on my wife, and I never would.
But I did experiment. A lot.
I put myself in sexual positions we usually associate with women: oral and anal.
And once I pushed through the initial shame and self-judgment?
I loved it. Like… really loved it.
That’s when I started to panic a little.
Was I gay and just didn’t know it?
Did I make a mistake marrying a woman?
Sorting Out Crossdressing and Sexuality: Attraction Isn’t Always Simple
Here’s where I had to break it down: sexual attraction and romantic attraction aren’t the same.
Romantically, I’m only into women. That’s still true. I can’t picture myself in a relationship with a man, emotionally or socially.
But sexually? I’m into both. Maybe even more drawn to men in certain ways.
Especially when I’m in that submissive headspace—whether it’s with toys, dominant women, or especially dominant men—something just clicks.
And for me, it’s not really about me getting off.
It’s about being used for someone else’s pleasure.
I love the feeling of being wanted like that—of being taken the way they want to take me.
That dynamic turns me on more than anything else.
I spent a while trying to label it. Am I bi? Heteroflexible? Something else?
And the truth is… I still don’t totally know.
But at the time, having a label helped me feel less broken. Even if it didn’t change my relationship or my day-to-day life, it made me feel seen—at least by myself.
Crossdressing and sexuality can get really tangled together, especially when you’re not sure where one ends and the other begins.
Is It Kink or Identity?
After all that, I had to step back and ask the bigger question:
Was this all just a sexual thing? Or was I actually exploring gender too?
Because this didn’t stop at toys and sex.
I got into feminization. Sissy play. Submission. I liked the feeling of being treated like a “girl” during sex. And for a while, I wondered:
Do I like this because it’s hot… or because it’s who I am?
Feminization and sissy dynamics blurred the line between sexual pleasure and gender identity in a way I wasn’t prepared for. That kind of play brings up a lot of questions for people like me—crossdressers, trans-questioning folks, anyone figuring themselves out.
It’s way too big to unpack fully here, but we’ll go a lot deeper in a future post.
Opening the Door to More Kink Exploration
Once that door opened, more followed. Especially around my submission.
My wife and I tried some new things—Mistress/slave play, chastity play, pet play, impact play. We don’t do them often, but when we do, I love it.
Eventually, I started exploring even more kinks and fetishes. Some I really enjoyed. Some didn’t do much for me.
Most recently, I’ve been experimenting with ABDL. Still figuring that one out.
Crossdressing and sexuality gave me the freedom to explore these parts of myself without guilt (or less guilt, at least).
We’ll go into more depth on all of those in future posts. There’s a lot to unpack, and I want to give each part of it space.
This Didn’t Change My Relationship. But It Changed Me.
I’m still married. I’m not looking for anything outside of that.
But questioning my sexuality after crossdressing was something I needed to do—for me.
It helped me figure out what turns me on.
It helped me learn the difference between what I thought I was supposed to want—and what I actually enjoy.
It helped me let go of a lot of shame I didn’t even know I was still carrying.
It all started with the clothes.
And maybe, at first, it was just a kink.
But it gave me the chance to ask questions I’d been too scared to even think about—and I’m so glad I did.
Have you ever started questioning your sexuality after crossdressing?
What did you discover when you gave yourself permission to explore?
I’d love to hear your story.
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