Something puzzles me, and I don’t know if figuring it out would be helpful for understanding myself, and therefore be helpful in my healing and overcoming from crossdressing. So I’ll write about it, and you guys can tell me if you relate at all, or if you have any theories.

Growing up I was very afraid to get too close to femininity. It was a horrible feeling to have my mother or grandma or aunt kiss me on the cheek and get lipstick on me. I don’t remember a lot of other vivid examples, other than not wanting to ever wear clothing that was not 100% masculine.

The strange thing was that growing up and trying out lipstick while crossdressing was not scary at all. It was highly arousing and pleasurable. Why was that so different? Later when I got to college, I even felt weird kissing my girlfriend when she had lipstick on. I was uncomfortable doing so. I don’t know if fear was still the correct word, but discomfort at least.

Why the big contrast? I’m wondering if perhaps it was because of showing signs of femininity on myself in front of other people. Perhaps I was terribly self conscious to not let anyone see femininity in myself for fear of them finding out my secret. But I’m not sure that really works as a theory, as likely as it sounds, for two reasons. 1. First, while as a child that makes sense, as a young adult I would think I would have been smart enough to realize that showing people I am overly paranoid of something actually points to a secret rather than hiding it. Being overly paranoid about appearing masculine is not a helpful strategy. So would that really be my motivation? 2. Second, as a child I didn’t even know that I desired crossdressing, other than having some dreams and daydreams about it. I never acted on them, and never actively felt like I desired feminine things or clothing or makeup. So why would I be afraid of feminine things before I even started crossdressing or knew about my crossdressing desires? I had no secret to hide.

I should point out that this dynamic doesn’t exist in my adult self today. I’m not afraid of feminine things anymore, nor afraid of kissing my wife. I no longer am afraid to wear clothing of various diverse colors, even purples and reds and so on. I no longer am afraid to wear clothing that actually fits, and is not super baggy. I’m sure this is an aspect of healing from crossdressing addiction as well as growing in age and maturity and becoming more confident with my appearance as a man. Though I experienced that fear only as a child and a youth, I wonder if any other crossdressers experience it still as adults?

In discussing this with other ex-crossdressers, my friend Ikthys had a theory about this which I find to be the most convincing explanation:

One potential “harmony” (to borrow from the old seminary…) of the aversion to lipstick and the desire to wear it is that the desire or attraction to femininity is “buried” and maintained as separate from core identity. It’s not to hide crossdressing, but to hide femininity, which actually can be a root cause of crossdressing, as a route of release to all the taboo feelings… So one doesn’t cause the other so much as a general issue being manifest in two ways- a public protection of one’s shred of masculine self image (which is even threatened internally by one’s own thoughts) and a private expression of one’s own femininity (or femininity according to one’s understanding of femininity I should say).

Since writing this post, I’ve also read about fear of femininity in a book, Transvestites and Transsexuals by Richard F. Docter. His view appears to be that fear of femininity as the untouchable and forbidden is partly what led us to become excited by wearing it. Here are some quotes on these ideas:

The understanding of heterosexual cross dressing, we shall argue, must also encompass the study of how identity and gender identity are formed, how arousal and pleasure are generated, how sexual scripts are learned and rehearsed, and how intense envy and fear of women may contribute to becoming a transvestite.

Betelheim (1962) has written of the “wounds” suffered by men who develop fear and envy of the femaleness of women…Young boys are typically given strong messages about clothing and gender conformity. Despite the contemporary acceptance of unisex clothes, most male youth are strongly socialized so as to wear only gender-appropriate clothing. For boys, this avoidance of cross-gender appearance is far more strenuously demanded than for girls. In our culture the undergarments of women have sometimes been referred to as “untouchables” -at the least, they are intimate clothing. Subtle barriers are erected to keep these undergarments out of public view.

The subtle rules that govern the privacy of women’s underwear may be viewed by some young boys as barriers that guard these “un-touchables” thereby giving them a special fascination. This possible fascination with the forbidden may set the stage for attributing to this clothing a special significance with erotic coloration.