How Do I Convince My Girlfriend that Crossdressing is Harmless?


I’m a male and I really like wearing dresses and skirts, however, my girlfriend does not approve. She has misconceptions about crossdressing and doesn’t really take it seriously.

I felt so unbelievably happy today that I was able to dress and attend my college classes. I felt alive and free. I felt like I was able to be myself. I would love to just dress like this most of the time. It would be a dream come true for me.

The problem is that my girlfriend doesn’t think it’s okay. I wish I could snap my fingers and magically change her mind. We love each other, but I feel like if I told her the way I truly feel about crossdressing she’d leave me, which I think is ridiculous, but I feel like I need her approval.

How can I convince my girlfriend that crossdressing is really nothing more than wanting more clothing options? I just want to feel pretty.

-Ruby Slippers


The problem I see right off the bat is that, in the vast majority of cases, male-to-female cross-dressing is not just about “clothing options.” There is usually much more to it than that. The clothes are merely tangibles that aid in the outward presentation and exploration of your feminine side. There’s ALWAYS much more going on internally regarding the topic of non-birth gender expression. If it is denial that is preventing you from seeing that, then by all means begin by dealing with the denial via deep and honest introspection, or perhaps with the aid of a cross-dressing-friendly counselor.

To be truly happy and live life in an emotionally healthy way, you will need to begin to acquire a reasonably accurate picture of why it is you need to express yourself this way. You will also need to give yourself permission to explore responsibly, and be able to accept that this is part of who you are, and there’s no shame in embracing that fact. By exploring responsibly, I mean you should be extremely careful to self-monitor your behavior in an effort to make sure you are not giving your second gender exploration such a high priority that your relationship with the girlfriend suffers as a result of neglect. Cross-dressing can very quickly turn into a beast that cannot be tamed. It happens all too often.

The truth of the matter is that crossdressing is often not a harmless activity. Peruse any the popular cross-dressing-themed online forums and you will quickly see what happens when a male-to-female cross-dresser mishandles his crossdressing and places it higher on his list of priorities than the slot his loved ones occupy. In these instances, the insatiable desire for crossdressing usually ends up being a relationship killer. Believe me, it is an easy trap to fall into.

You will eventually need to have an honest, open discussion with your girlfriend where you place before her all of your feelings regarding your gender exploration. You will also need to listen to her when she expresses how she feels about having a significant other who engages in this. When its all been said and heard, you both will be faced with the task of deciding whether or not you’re actually compatible in life as partners. I mention this because I’m of the opinion that, if she’s not fully accepting of your gender flux, then you two simply are not compatible as life partners, and with regard to a serious relationship, you essentially would just be forcing a square peg in to a round hole.


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One thought on “How Do I Convince My Girlfriend that Crossdressing is Harmless?

  1. Generally in agreement with what you say here, but I do want to add that I have known of cases where male-to-female cross-dressing really was just about wanting to ‘feel pretty’ or something similar, men who have cross-dressed for decades, just because they enjoy it, and once people accepted that they just liked to dress differently, it didn’t change anything.

    However it does seem to be the minority of cases, and Ruby Slippers really does need to check himself for any possibility of being in denial before he can begin to work this out with his girlfriend.

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