What's the difference between a crossdresser and a transsexual?

It’s an old joke in the transgender community that goes like this:
Q: “What’s the difference between a crossdresser and a transsexual?”
A: “Two years”

This provides some humorous levity while astutely implying a truth about transsexuals – many of them started out as crossdressers. Unfortunately, while it makes for a fun observation it doesn’t really provide any useful insights for those who are struggling with their gender identity, or for others who hear that someone they love is a crossdresser.

It’s also easy to describe the difference between a crossdresser and a transsexual by sharing the definition of each word and describing transgender terminology.

It’s more difficult to help those struggling with their gender identity determine whether they are a crossdresser or transsexual, though I’ve made such an attempt a few times.

Five days ago I had sex reassignment surgery. As someone who once considered themselves a crossdresser, and now considers herself a transsexual woman without question of doubt I feel I’m in a position to provide some valuable insight for those struggling with a similar question. It goes without saying that each person is different, and this question is best explored together with a qualified therapist, after all you’ll make life altering decisions based on what you discover.

How Do I Know if I’m a Transsexual?

    • You consider yourself a woman: Crossdressers enjoy being woman for a time, but still consider themselves to be a man. Many are even happy being a man, and indulging their feminine persona a few times a week or month is all they need. Even if they fantasize about being transformed into a woman, crossdressers never seriously consider this to be a long term way of life.
      Transsexuals feel an intense cognitive dissonance between the genders of their mind and body. For me this manifested itself in a constant ‘mind static’ that pervaded every moment. I couldn’t enjoy the fullness of life because of a birth defect that placed me in the wrong body. For some it gets so serious that they seriously consider suicide as the only solution.
    • It’s about who you are, not the clothes: For many crossdressers the infatuation with the feminine revolves around their appearance. The clothes, the makeup, the impossibly high heels. Even for crossdressers who strive to blend in, it’s about being feminine. Being feminine feels good and exciting.
      For transsexuals the entire experience doesn’t revolve around the accessories of gender expression. Another common refrain is, “How do you tell the transsexuals at a transgender conference?”, “They’re the ones wearing jeans”. It’s about who you are, not who you appear to be.
    • You take the good with the bad: Transsexuals realize that there is no escaping being a woman. No time off for good behavior. We can’t decide to be a man for a certain circumstance just because it would be easier. While we may lament the discrimination we face as women it doesn’t factor in to whether we are a woman.
    • Womanhood is messy reality, not an idealized fantasy: If your sole experience of womanhood is as a fantasy, then you don’t have enough information to say that you’re a transsexual. Many crossdressers only experience what they consider the ‘highlights’ of womanhood (It’s another post as to why I don’t believe these are the actual highlights). Nights out feeling sensual, or safe gatherings dressed in their finest feminine attire. The truth is that womanhood isn’t quite as clean or elegant. Many transsexual woman experienced and embraced the messy reality of womanhood before transitioning. If you’re wondering, seek out every day experiences as a woman.

Embrace Who You Are

Gender Identity isn’t a game that you win by being more feminine. The only way to win is to discover where you are on the spectrum, and accept yourself unconditionally. If you’re not a transsexual, that’s okay. If you are, that’s okay too.

I’ve shared my thoughts on how to determine whether you’re a crossdresser or transsexual. What insights have I missed? If you’re a crossdresser and firm in that knowledge, how did you come to this realization?

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Wendy (@tissy)
2 years ago

I knew as a kid, but hid it away, hoping that this wasn’t true. Then, I accepted myself, I can’t tell you exactly when, but it was before puberty…So, that was a hard time…but I did what I could and I’m now finally on the right path, at last. I’ve always just been me, whether people want to see me as a man, not for much longer….or a woman…it matters not to me, I’m just me. Transgender.

Roxanne Lanyon
2 years ago

Is it possible to evolve into being transgender? I know that, when I was young and just starting, I certainly was a crossdresser. But, especially since my last divorce 2 and a half years ago, I have become more and more female, especially feeling female. Every night I put on my lace ankle length night gown to sleep in, and keep it on for hours in the morning. I think the only reason I change into boi clothes is the fear of dressing in my small little town! I so wish I could get over that! I also find myself… Read more »

GloriaUpjohn (@gloriaupjohn)
2 years ago

The more I learn the more complex and
confessing it seems✅

I love wearing girly satin undies
have been doing so for a long time

Trying to loose a bunch weight so
I can dress as an attractive girl in public


Am I looking in the right place‍♀️

Thanks Gloria

Amy Myers
Trusted Member
Amy Myers (@amylove2dress)
1 year ago

As I’m quite new to this, I am finding it a bit scary, and thanks for the article. I truly feel like a CD, and not a TS, and I have been scared about going down that road. My male side is very strong, and I don’t want to give it up! I love being a man, never been into macho, but a man none the less. However, I also love being Amy, and kind of don’t know where she came from. Sounds weird, I know.
Thanks, Vanessa, it helps to clarify some things in my mind.

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