Should I Wear My Sister's Clothes Behind Her Back?


I've been corresponding with a 17 year old straight cross dressing guy who is in a bit of a dilemma:

1) He's in the closet about cross dressing.
2) He's used his sister's clothes in the past without her knowing and she got really mad at him when she found out.

He writes:

"She (sister) told me her privacy felt pretty invaded, and didn't like me too much after that. i understand that; she wants privacy. what should i do for clothes when i want to dress up? should i still use her clothes, and return them right away after i use it? i'm not about to go out buying girl clothes, or much less have my mom go shopping for me."

First off you need to stop wearing your sister's clothes behind her back. Privacy is privacy.

You could go to a thrift store and get a few items there. September and October are the best months to go shopping for your cross dressing needs because if ever questioned you can say you lost a dare and now you have to dress up in women's clothing for Halloween. The sales rep will find it cute. Or you can always say "It's a long story, maybe I'll tell it to you someday".

Nobody like's to be judged negativey but it's always been my experience that when you make shopping a fun experience the sales rep or cashier will be thrilled to help you find an item that makes you happy. Let's not forget, that they want your cash so they are going to try to help you. Plus most thrift stores don't have sales reps. They only have a cashier so you are free to shop without anyone bothering you.

The key to hiding an item from your parents after you get in the house, is to also buy one item that is for boys. This way if they ask you what you got in the bag then pull out the boy item from the bag and show them. If they ask to see the rest of the stuff you simply say "oh it's just a few more things nothing too crazy," and change the subject like "what's for dinner?"

Also, throw away the receipt. This way if your parents demand to see how much you spent you can honestly say you don't have the receipt. I don't believe in lying so this will help you stick to the truth.

If you think there is a way to get your sister on your side than go for it. Negotiate with her. If she helps you get clothes then maybe you can help her with something she needs. This could very well be a bonding experience. Something that can bring you two together instead of pulling you apart. The key here is to restore the trust.

I'm not sure if my little sister knows this, but when I went on American Idol dressed as Amnesia back in 2002 I was wearing my sister's clothes; with the exeption of the shoes. Hey sis, did I ask if I could wear your clothes or did I take them behind your back? Your clothes sis got me far. I couldn't have done it without you. Thank you.

What do you suggest this young man do in order to be able to dress up and not have his parents find out? Should he ask his sister for help?

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