I Am a Teenage Crossdresser
So, as some of you may know from my previous story, "Trying to tells someone," I feel that coming out to just one person will make me feel much more at ease. But, due to unfortunate circumstances (as detailed in the above-mentioned story), I can't tell any of my family and I don't have any close female friends. Long story short, I had only two people that I could possibly tell, and both were guys my age. So yeah, not easy.
For a week, I'd been trying to tell one of them of my crossdressing interests, but never brought the conversation to the right place, or just never found the courage. But finally, over IM I was able to get the conversation to the right place (credit to ExponentiallyStressed), and sorta speak my mind! For those who want to know how the conversation went in great detail, please read the next paragraph; otherwise, skip it:
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I started by telling him about how annoying it was to have to be back at school after a 2-week spring break, like having to do HW again, etc, and he agreed. But then, I said that I was sorta happy about being able to be around all the people again, and stuff like that. I said they are a great source for all kinds of new information I'd never be exposed to or ever even think about, which I then used as a segway to introducing to him a TV show called "RuPaul's Drag Races," (THANK YOU SO MUCH EXPONENTIALLYSTRESSED!), which I just said that a few girls at school had shown me it. He believed it. From there, we talked about how it was a funny concept, and I spent a bit of time trying to figure out what he thought of it. Here, I had to then make a decision; should I tell him that I've *tried* crossdressing, or that I'm just *interested* in it? Unfortunately, I was too scared to make the jump to the idea that I had *already* tried it, so I simply told him that it looked fun, and I'd try it if I ever got the chance. I justified it by saying that I've always wondered what girls' clothes feel like, and he sorta agreed, so that encouraged me on. I began telling him how badly I wanted to try it, just because it seemed to simple a thing, yet so difficult to actually get to. And I think he got the message, because he offered that I find a group of crossdressers or something, but that's about as far as it went.
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All in all, I told him that I wanted to try girls' clothes, and he seemed to be quite accepting of it. We didn't get much further, because he had to go, but I made him promise that we'd talk about it again later (though I now realize that I didn't make him promise to keep it a secret). Ideally, I'd want him to also express interest, which from what it seems, isn't completely impossible. Still, he seems to be on my side, and I'm on the right track. I feel better already :D
Thanks for reading this essay, everyone, and if anyone has any tips or stories, please please please post in the comments! I, and LOTS of other people could benefit greatly (as evidenced right in this story!) Thanks!
For a week, I'd been trying to tell one of them of my crossdressing interests, but never brought the conversation to the right place, or just never found the courage. But finally, over IM I was able to get the conversation to the right place (credit to ExponentiallyStressed), and sorta speak my mind! For those who want to know how the conversation went in great detail, please read the next paragraph; otherwise, skip it:
-----
I started by telling him about how annoying it was to have to be back at school after a 2-week spring break, like having to do HW again, etc, and he agreed. But then, I said that I was sorta happy about being able to be around all the people again, and stuff like that. I said they are a great source for all kinds of new information I'd never be exposed to or ever even think about, which I then used as a segway to introducing to him a TV show called "RuPaul's Drag Races," (THANK YOU SO MUCH EXPONENTIALLYSTRESSED!), which I just said that a few girls at school had shown me it. He believed it. From there, we talked about how it was a funny concept, and I spent a bit of time trying to figure out what he thought of it. Here, I had to then make a decision; should I tell him that I've *tried* crossdressing, or that I'm just *interested* in it? Unfortunately, I was too scared to make the jump to the idea that I had *already* tried it, so I simply told him that it looked fun, and I'd try it if I ever got the chance. I justified it by saying that I've always wondered what girls' clothes feel like, and he sorta agreed, so that encouraged me on. I began telling him how badly I wanted to try it, just because it seemed to simple a thing, yet so difficult to actually get to. And I think he got the message, because he offered that I find a group of crossdressers or something, but that's about as far as it went.
-----
All in all, I told him that I wanted to try girls' clothes, and he seemed to be quite accepting of it. We didn't get much further, because he had to go, but I made him promise that we'd talk about it again later (though I now realize that I didn't make him promise to keep it a secret). Ideally, I'd want him to also express interest, which from what it seems, isn't completely impossible. Still, he seems to be on my side, and I'm on the right track. I feel better already :D
Thanks for reading this essay, everyone, and if anyone has any tips or stories, please please please post in the comments! I, and LOTS of other people could benefit greatly (as evidenced right in this story!) Thanks!
By:
Skier24
Age:
18-21
,
Male
