Batgirl: How I Told My Best Friend

by Jessica De Leon on April 25, 2009

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I decided to tell my best friend about my crossdressing on Thursday. I had wavered back and forth and stressed out about this for about a year. All the while, I figured that there was a great possibility he would take it well and support me. On the other hand, there was that small possibility that he would react negatively and things would be awkward between us from then on.

We have known each other for about 9 years and throughout our friendship we have shared many personal things with each other. I have always known him to be an extremely open-minded person, so this gave me more confidence. At the same time, I did not want to jeopardize our friendship. Was there really a need to share this part of me? There was no obvious answer to this question, but there were several factors that led me to have this conversation.

He comes over to my place a great deal, sometimes every day. There were times that I felt like Jessica needed to be out but him being there prevented it. This would cause me to feel a little cranky, although I think I succeeded in hiding this emotion. One time, in fact, he knocked on the door while I was dressed head to toe as Jessica. As a result, we could not let him in. My wife answered the door while I hid in the bedroom. For the rest of the evening, I felt so guilty for letting my dressing interfere with our friendship. The pictures that we took that night show this quite clearly. Additionally, when we would hang out, I would occasionally feel awkward or guarded, like I was hiding something from him.

A few of days after I started this blog, I resolved to tell my friend about Jessica. I started by asking him if there was anything that I could ever tell him that would make him not want to be my friend. He answered “no”, small victory. I rambled on for a few moments before I blurted out, “I sort of have a secret identity”. “Like Batman?”, he asked. I responded by saying “yes, if by Batman you mean Batgirl”.

This, of course, was not quite specific, so I went on to say that from time to time I dress up like a girl. Let me tell you that he couldn’t have reacted better. He assured me that this was no big deal, and that he couldn’t believe that I was stressing about it. For the next 30 minutes or so, we continued discussing it and he even wanted to see a picture of me.

Since then, we have hung out, and I feel so much better about our friendship. It is certainly stronger and more robust, further proving to me that we can trust each other with anything. As a bonus, my friend wants to try dressing up sometime as well. How could I ask for anything more from a friend? I feel even more comfortable with myself, and have more confidence in letting the dual nature of my personality show.

Thank you, my friend. I’m not sure you had any idea how much that conversation and your subsequent reaction meant to me, but I am sure that after reading this you have a good idea.

So to all the readers out there, have you had a similar experience? I know that I am blessed to have such a good friend, and I can only hope that you all do as well. If you are thinking about telling a good friend, be sure to ease into it. Drop a hint or two, and if either of you feels awkward then perhaps it is best to back off. If you do share though, and it works out, your friendship will be the toast of Gotham City.