Cross-dressing, Trapping

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No.659 : Anonymous Writer [09/09/28(Mon)07:39]

I think it's time to admit to myself that I want to start crossdressing.

Unfortunately, I'm absolutely terrified of anyone finding out (I live in a small town, in a house with several roommates) so buying clothes in a shop or online is something that is going to take a lot of balls to do. No pun intended.

Any tips for someone just starting out? I'm very masculine in appearance so I'll just be doing this in my own private space, but still.

No.663 : Jentrap #CkXVw0MbRs [09/09/28(Mon)20:57] []

Unless you live in KKKville or something, I wouldn't worry too much about being found out. No one outside your house cares if they even know you, and roommates might tease at the very worst.

Hell, if you do a good enough job (passing, etc.), they might even start to like you for it! (Always remember Rule 43.)

I'm still at the beginning of my journey, so I can't give very much expert advice on what works well. Just dress the way the girls around you are dressing, I guess.

If it's just for your own enjoyment, you should already know what kinds of stuff you want just by looking at them.

And it's moreso your own fear that's holding you back than any real danger.

No.666 : Anonymous Writer [09/09/29(Tue)07:58] []

You're probably right. One of the things that scares me is that I live in a small college town, so most of the people who work at the stores where I could buy female clothes would be my friends...

I may end up just ordering online and seeing where things go from there; easily concealable items such as panties or hosiery. Unless I make some very drastic changes in my lifestyle I'll never pass -- and I'm not intending on passing, as I will mostly do this for my own enjoyment, in private.

Ultimately though, yes. I just need to get over my fear.

No.672 : Jentrap #CkXVw0MbRs [09/09/30(Wed)20:40] []

I just bought a crapload of makeup from the Wal-mart, plus some breast forms to top it off. The cashier didn't even flinch.

I think I'm getting brazen.

No.674 : Anonymous Writer [09/10/02(Fri)17:34] []

I'm jealous! I'm in the UK so we don't even have a Wal-mart. I'm contemplating making a day-trip to the nearest big city to buy things anonymously.

No.675 : jo [09/10/03(Sat)11:48] []

>>666
I would recommend starting small, like you imply, with panties or hosiery.

Jeans are also a good place to start; just be cognizant of how difficult it can be to find the right size.

Having hidden clothing since junior high on through college; I've come to find that no matter where you hide something, the hiding place will always be discovered in one way or another. Human curiosity and the sheer serendipity are too strong for common secrecy.... but with that said, panties are easier to hide than, say, a strapless dress.

No.676 : Jentrap #CkXVw0MbRs [09/10/04(Sun)14:39] []
>Jeans are also a good place to start; just be cognizant of how difficult it can be to find the right size.

Jeans were easy for me. I just used my guy size and they worked perfectly.

No.686 : Anonymous Writer [09/10/07(Wed)10:13] []

>>675

Oddly enough I'm not so much worried about hiding them, but just going out and buying them. It seems to be a big psychological block for me and I'm not sure why.

I did go online and browse a few online shops the other day, I even filled out a basket and was almost going to proceed to the checkout before chickening out. :(

No.697 : jo [09/10/10(Sat)18:57] []

>>686
Interesting. Certainly understandable though, especially if you live in a small town, as you said.

I know of some who coordinate simple excuses when in-store -- saying it's for the girlfriend, referring to an anonymous shopping list, shopping in an adjacent town. Personally, I've always been comfortable shopping in the early hours of the morning; early as in getting to the store at 8:30am on a Sunday, after it opens at 8:00. I struck up a conversation with a clerk in the women's department at Target not too long ago, and I was completely relaxed.


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