Going to Tell My Friend

[Wierd Matty Makinen]

Yes, as it says on the tin, I’m going to tell my friend that I’m a crossdresser. Because both of our work schedules are bugger all, it has to be that weekend after this coming one [September 3], which is great, as it gives me two weeks to stew and fret. The purpose for our meeting is really to talk about our road trip to New England this October, but my crossdressing is supposed to be a significant part of it. One of the reasons for the trip [of which there are around thirteen] is to boost my self-confidence, to break me out of my shell of self-loathing and cynicism, and my wearing women’s clothing is a crucial part of that to me.

I just have no idea how to play it out. Do I say it outright or kind of ease into it [no, I don’t know what I mean by that]? Do I talk about the trip while writing it out for him to see [which seems kind of stupid, but that was Plan A]? I was hoping someone might have some kind of suggestion or advice.

I’m not really worried about his perception of my bisexuality; that rumor was in circulation during Senior year of high school. That fact that he still talks to me is answer enough that he wouldn’t care about that, and that he’s decently open-minded. It’s just the crossdressing I’m not sure about, whether I should just leave it for when we get to our destination.

[lingerieLiz]

Does your friend know or not? You say the trip is supposed to boost your self-confidence and wearing fem clothing is part of it. I"m lost

[Wierd Matty Makinen]

Does your friend know or not? You say the trip is supposed to boost your self-confidence and wearing fem clothing is part of it. I"m lost

No, he doesn't yet.

[Tiffany Jane]

Would your "coming out" to your friend ruin the plans of your trip either way? That is how I would look at it. It would be reassuring beforehand to know that your friend was going to be there with you as you "break out of your shell". It could be difficult to follow through with your plans if your friend found out during the trip and made you feel that your perceived support wasn't there. It is my experience this last year, as I have talked to friends and family about what it is about crossdressing that I am going through, that in conversation, I connected a lot of dots about their thoughts about me that left them feeling they knew a fuller picture of who I was. I have had support from wife, friends, and family. I could go through the same scenarios as you probably are, but it is your friend and you know him best. What comes from your heart is the best course of action, although it may not be met with the desired results.

I do know that talking with others about what I am going through is helpful, as it builds a support group among those close to me. It is that support which will allow you to find strength in new ways to express yourself.

[docrobbysherry]

U can't sand bag your friend. It will ruin "the trip" for both of u and possibly damage your friendship.

For u this trip is your big "coming out party". What's it supposed to be for him? Your dressing is about u and no one else. Why do u need or want to involve him? It seems like you're making him the center of your dressing activity. If he's not your roommate, best friend, or significant other why r u doing this? I don't understand----

[Krisi]

My rule is to tell nobody who doesn't need to know. Obviously, if you are planning a trip with him and you will be dressed as a female, he needs to know, but don't be surprised if he backs out of the trip.

Sometimes crossdressers forget that while it may be fun for us, it's not always fun for others. That's self centered and selfish.

[Wierd Matty Makinen]

Actually, I wouldn’t really say the road trip would be a coming out party. There are thirteen valid reasons for the trip, and my crossdressing is just a sideline, another route for my enjoyment. The primary purpose is to just get a couple friends back together and have some fun before something bad happens [and something bad is going to happen; I’m not intentionally trying to be weird or an alarmist, but I really can feel something bad going to happen, eventually].

I just wanted to let the others who are coming to know, but now I’m doubting the whole damn thing. The more I mull it over, the more this entire thing seems so incredibly stupid. It really does seem less like a group of friends on the road and more like I’m dragging them into my mad daydream. Hell with it, nobody’s going to know. It’s not important enough.

[Tiffany Jane]

Give it thought. I'm not trying to discourage you from taking some time for yourself. I am not connected with your circle of friends and was only expressing my opinion based on my experience. First went horribly wrong for me and ten years later, I am breaking through ten more years of walling myself in. Picture what it is that you truly want and when, then make it happen!