Crossdressing gave me the space to explore my sexuality. Sexual exploration, in turn, made me question if crossdressing itself was a sexual act. And that exploration eventually brought me face-to-face with sissy play and feminization.
Honestly, it started with porn.
I searched for people like me—crossdressers having sex. I didn’t care who it was with. Men, women, other dressers—I just wanted to feel like I existed in that space.
That’s what led me into sissy porn, forced feminization videos, and other fantasies I didn’t expect to relate to as strongly as I did.
At the time, I didn’t fully understand why I liked it.
But I knew I did. A lot.
We’ll get into the emotional impact in the next post. For now, I want to talk about what it looked like for me physically—and what I actually did during that part of my journey.
Exploring Sissy Play and Feminization Through Fantasy
It started out simple.
I’d dress up—sometimes lingerie, sometimes something soft or cute—and watch sissy play and feminization porn in girl mode.
And every time, I wasn’t just watching. I was fantasizing about being the sissy.
I’d masturbate to the idea of being used, degraded, and submissive.
Over time, I started acting it out.
If a scene showed a girl being pegged? I’d use my toy anally.
If it showed oral sex, I’d use my dildo orally.
And honestly, seeing my lipstick smeared across a cock? That was a huge turn-on. Still is. The taste of it? Even better.
Why Certain Words Never Felt Right
A lot of sissy content uses names like “slut,” “bimbo,” or “whore.”
So I tried using them on myself too.
But honestly? I hated it.
It wasn’t the humiliation that bothered me—I love humiliation when it’s about emasculation.
The problem was that it felt like the degradation was aimed at femininity itself.
Like being feminized was the insult.
And that didn’t sit right with me.
Because even in those kink scenes, I didn’t feel insulted by becoming feminine. I felt seen. I felt wanted.
I wanted to be stripped of masculinity—but not at the expense of femininity.
I don’t know if that even makes sense. Honestly, it’s probably something I should unpack more in a future post.
When Sissy Play and Feminization Became Real-Life Exploration
Eventually, these fantasies stopped being just solo play.
My wife and I started experimenting with them together—mostly in private, when we had time alone.
It wasn’t constant, and it wasn’t part of our daily lives, but when it happened, it felt huge.
I wore chastity.
I dressed up and did housework.
Sometimes it was playful, other times more serious—but it always came back to this feeling: I was being used for her pleasure, not mine.
And what surprised me the most? I didn’t need to orgasm.
I still felt sexually fulfilled—sometimes more than if I had finished.
That was new for me. I wasn’t used to feeling satisfied without release.
But something about the dynamic, the purpose, the giving—it just hit differently.
Even when she wasn’t actively participating—just giving the orders or setting the tone—I felt that purpose.
I felt useful. Submissive. Wanted.
Submission, Fulfillment, and Feeling Feminine
The more we explored, the more I realized I felt most aligned when the focus wasn’t on my pleasure.
It was about hers. Or about the fantasy of being used by someone else entirely.
Whether it was pegging, using toys, or just being given a task while caged, it felt different than anything I’d known before.
Not because it was wild or extreme—but because it felt right.
I wasn’t overthinking. I wasn’t chasing release. I was just… there. Being useful.
My wife and I have even talked about extending that dynamic—maybe turning it into more of a lifestyle thing, especially around housework.
But with kids and day-to-day life, it’s not really doable right now. Still, the desire is there. And when we do make space for it, it feels right.
Looking back, those experiences weren’t just hot—they were defining.
They helped me understand what I wanted.
And more importantly, they helped me see who I was becoming.
Sissy Play and Feminization Were More Than Just Kink
Yes, this post is about sex. About fantasy.
But it also marked the beginning of something deeper.
Sissy play and feminization were how I gave myself permission to try things I didn’t know how to name yet.
It was messy and weird and incredibly hot—but it was also clarifying.
Even if I didn’t know it at the time, it helped me start asking bigger questions about who I am.
And that’s what I’ll be talking about in the next post—the emotional side of it all, and how those experiences made me seriously start questioning my gender identity.
Your Turn
Have you explored sissy play or feminization before?
Did it feel more complicated than you expected?
I’d love to hear your story.
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