As much as we want to control exactly who knows our secrets, once someone is told, that control is divided amongst everyone in the know. While we can swear someone to secrecy, keeping that pact will forever be their decision, which can be quite difficult for us to accept.
When we choose to come out to someone as a crossdresser, it is usually best done on our own terms and on the timeline of our choosing. The revelation of such a grand secret is tough enough when you are the director, but what about when a friend or family member tells someone else?
You’re not around to see that person’s reaction and answer any questions that they might have about crossdressing.
Since 1999, I have told six people in my life about Jessica (not including counselors) and each time I was able to break the news how I wanted. This has always led to a lengthy conversation in which the loved one was able to come to terms and have all of their inquiries answered. I’ve always asked for or implied secrecy and to the best of my knowledge this has never been broken.
In the past several months my wife and I shared with two friends that are married, and I had no illusion that they would not share this with their husbands. Was I scared? Yes, a little bit. As we’ve discussed in the past, revealing to a friend or family member that I am a crossdresser has been fear-inducing. The wording, the waiting and the anxiety of how and what they may be thinking can be really, really terrifying.
The good news here is that both husbands (who are also friends of mine) took the news quite well, and have not judged me or ostracized me in any way. While I’ll admit that we haven’t discussed it personally, one of them is a regular reader of my blog, and has given me plenty of positive feedback and advice.
So add two more people to the list of friends and family that know about Jessica and are accepting. In case your wondering, I am not trying to brag about this, but I do want to use my situation to make a point. None of these people have been bothered by the fact that I crossdress. While it may have been a bit of an initial shock, this has not kept them from spending time with me. This goes to show that things are changing, at least in my generation.
There are a million things in this world that are worse than being a crossdresser, and in my personal experience, people are starting to understand this more. We are definitely a misunderstood group, but if we want that ignorance overturned, we can all do our part, by educating one person at a time.

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I used the fact that people can’t keep secrets as a means to come out at work. I told my two closest friends suspecting that they would gossip about me and sure enough one of them did. It sure made my job a lot easier using gossip as a tool.
Yes, many people are prone to gossiping and sometimes a favorite pastime. I’ve been hesitant to share with a couple of family members who may leak the information, but we’ll see what happens.
When we told one of our couple friends, we told the wife. I was really nervous about how the husband would take it. The wife was cool about it, but everytime I saw the husband I felt weird, I later found out that he didn’t know yet. When he did find out, he was actually more into it than his wife was, he wants to go out with us to see me dressed, his wife however, doesn’t.
Yea, the crossdresser’s paranoia. Classic case, I know how you felt. Are you going to hang out with him while dressed, or are you not sure yet?
I wouldn’t mind, but his wife is worried about it, he’s bi, she’s worried he may be too into it. We offered to go out with them several times, but she ends up being too tired, or not feeling good or something along those lines.
Oh, I see. There’s no getting around that one.
My mother-in-law walked in on Julie one afternoon, so I “had” to tell her. She lives with my sister-in-law, but I don’t know if the news has been shared. At first, it made for tension when I next saw my sister-in-law, but time has passed, nothing has been said, so I still don’t know but now I don’t care! In this, I follow the advice of the great philosopher, Popeye: I Yam What I Yam.