Truth or Dare

Crossdressing is sometimes portrayed as a challenge.

No, this isn’t about the challenge of trying to find the right foundation to cover up our stupid facial hair, this is about the… crossdressing DARES that we see online from time to time.

Do you know what I’m talking about? They seem to be mostly aimed at the “crossdressing is a kink” crossdresser (not that there is anything wrong with that).

These challenges are usually broken down into steps with the first “challenge” being something rather small and progressively becoming more advanced and tend to push people out of their comfort zone.

Not that this is a bad thing. This is EXACTLY what building up the courage to go out en femme requires. Baby steps. If they are thoughtful and well written, they can be immensely helpful when it comes to providing… ah, step-by-step guidance as to what you do first, what comes next, and so on.

These challenges almost always concentrating on what I call the practical side of crossdressing, such as focusing on clothes and heels and makeup. Which can be important! I think they are! However, they usually skip over the emotional and psychological aspects that crossdressing and presenting en femme usually requires.

What I mean is that it’s easy to find a wig, but often the wrong wig can trigger dysphoria. There are countless dresses that will fit us, but if we don’t like how we look in them it can be hard to feel that yes, we CAN be, and that we ARE beautiful. We can follow along with a makeup tutorial on Youtube, but if the products used aren’t right for our face shape or skin type we probably won’t look like the supermodel that we were expecting.

These disappointments can trigger a lot of negative feelings and frustrations and hopelessness.

In a lot of ways the practical sides to crossdressing are a zillion times easier than the psychological parts. Essentially a dress can fit, the heels can be comfortable, but if we don’t FEEL cute, if we FEEL we look “too male”, the clothes don’t matter at all.

Does that make sense? I hope so because I don’t know how to explain it differently.

Sometimes the challenges are a “point system” where you award yourself points for the different tasks you complete. Once the points are added up you can find out how much of a sissy you are, or whatever. Again, these tend to be mostly kinky in nature with wearing panties is worth one point but dressing up in teeny-tiny schoolgirl skirt while having anonymous sex with a stranger in the backseat of his 1993 Honda is worth ten points or something.

It’s sometimes jarring at how quickly the sexual nature of these challenges can escalate. The first challenge is tiny and innocent, but then all of a sudden you are getting dared to put on a frilly pink French Maid dress and having a gangbang at a truck stop.

I tended to score very low on these. And I have nooooo problem with that.

Like other things out there, these lists can be fun but also play up the sexual aspect of crossdressing. Again, there’s not anything wrong with that. But many of us dress how we do for so many reasons and kinkiness isn’t even relevant. There’s the fantasy aspect of this for some of us but for some this isn’t our truth.

From time to time I think about writing my own version of something like this, but I think the “challenges” would be, well, not fun. It’s easy to dare someone to buy a cute bra, it’s another thing to actually do it. Buying a bra is not as easy as it sounds, even if you’ve been wearing one for years. Cup size and band size are too be considered, and there are different bras for different outfits and different bodies and different, well, GOALS, I suppose.

But I suppose this is how ANYTHING is. Telling someone how to change a tire SOUNDS easy but, well, it’s NOT. Everything is easier said than done.

I am also hesitant to write something like along the lines of “instructions” because we all have different goals when it comes to this side of us. When someone asks me “how do I crossdress?”, I struggle with how to respond because, well, crossdressing could be as simple as painting your nails or as time-consuming and expensive as hair removal, breast forms, thigh pads, a $90 makeover, an expensive wig, and a killer dress with matching heels. It’s kind of up to you.

And! Step-by-step doesn’t always work for each of us. Our journeys are not linear or identical to everyone else (which is a tiny reminder that we shouldn’t measure our progress or self-worth in comparison to anyone).

I know I often sound like a wet blanket when it comes to crossdressing. I focus a lot on the reality of this side of us which can be a buzzkill. But please know that I absolutely understand that expressing our femme identity or wearing what we want (for any reason) is important AND I think it is really super fun. Yes, it’s a lot of physical work to shave and wiggle into a dress and cinch my corset and strut all day in stilettos, but it’s SO MUCH FUN. I love it. I love every minute of spending the day en femme. I love getting ready. I love shopping for clothes and wearing new panties for the first time. The magic is always there.

I suppose these challenges and the idea of awarding points is similar to thinking about what we SHOULD be, what we SHOULD look like, and so on. It’s easy to look at a list like these and feel that we are not femme or brave enough if we’ve only done half of the “challenges” and the rest feels intimidating.

Sometimes these “challenges” include something along the lines of “tricking” a guy at a bar that you are a “real” girl. UGH. So many things are wrong with that. There’s no such thing as a “real” girl. I KNOW that this is referring to “fooling” someone that they are a cis gender girl but girls are girls, trans or not. And! you don’t need validation from some loser drinking beer at some stupid bar. A guy being attracted to me isn’t a victory, in my opinion. It’s not the compliment that we are led to believe.

Listen. This side of us is super fun and amazing but it’s also some of the most difficult parts of our lives, especially on the emotional side of who we are. We don’t need to make it any harder by measuring our progress and what we do or what we wear against some silly list or by comparing ourselves with anyone else.

And yes, like changing a tire, this is easier said than done. Sometimes I feel cute but then I feel absolutely monstrous in comparison when I see photos of Heidi Phox or Farrah Moan.

On the flip side I do feel like a supermodel when I look at a recent photo of myself and compare it to a picture from a few years ago.

But maybe that’s the point?? Maybe we need to focus on our own personal growth and be happy with any progress we make, no matter how small or how long it takes.

Love, Hannah