The best thing you can do is be honest. For instance, if you tell her it is for a one-off event (halloween, party, dare, whatever) and she DOES help you. You've just cut yourself off from anything further. this scenario SEEMS to be getting you what you want, but then it shuts it all down or you have to asmit you lied and manipulated her, which shuts it down. Honesty is the only way to fully get what you want. So, if you do open up to her and ask for help shopping for you because YOU want it but are scared to do it, then if she agrees (and the chances are pretty good she will) then it is open for her to help you again, or suggest alternatives.like her giving you some of hers that she doesn't wear anymore.
First you ask her if she would/could be open minded whine a friend needs help with something. Then you have to tell her that because you really trust her you have a secret you wish to share with her. Tell her you are really scared to tell her, but she's the only one you feel you can trust. <br />
Then tell her... And answer any question she askes. And if she starts to get wierd, just start crying, cuz it's over dude, and that's pretty much it. If your best friends sister won't help you.. your on your own. and with any luck she'll take pitty on your crying and keep the whole thing on the low down.
Thanks.. I wish I had had the guts to do it myself... it takes some serious leap of faith. People can surprise you, and it's amazing where you can find true friends sometimes.. if the above advise works, you may have a friend for life.
I think you better ask your best friend if it's ok first, he may not want to be your best friend anymore afterwards
Alright here's a serious answer, why not just ask what it is like to wear womens clothing, then say you'd like to try it out cuz it's not fair that women can try guys clothes but guys can't try girls clothes and you don't have any girl clothes so can you try on hers
This one is not bad either... if she says no you could always ask her to go shopping with you. Maybe you could start a friendship there?
if you are not old enough to dress yourself, you have no business asking some one else do it for you.
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Some of the previous answers are quite good in spite of your rejection of them. It sounds like she's pretty well established in her feelings about this issue. While you don't mention her and your age you must be adults. I like the previous suggestion that you ask her to help you shop for some things. <br />
Now my suggestion is to use this month of October the same as many cross-dressers do by taking advantage of "Halloween". While in a casual conversation with her and you can tell she's calm and relaxed mention to her that you have a problem and are hoping she would help you out with it. if she responds in a calm positive manner you could continue telling her that you've been invited to a party for Halloween and could really use her help. If she's still with you and asks what it is you simply go on and tell her that it's a masquerade type party and all have to dress as members of their opposite sex. tell her you've never done this before and would like her help in dressing as a woman. If she asks how she can do this you simply respond that we both seem to be about the same size and possibly I could try a few of your things on to verify size and fit. After we establish that I'd love to have you go shopping with me to buy what I'll need as I know you don't want me to wear your clothes. If this works then you either will end up having an outfit of hers to wear because she didn't want to go shopping with you and offered you her things to avoid having to shop. Or, on the other hand, she'll offer to help you shop for your feminine outfit and appropriate lingerie and you'll end up with your own girl outfit. If this works you're guaranteed something feminine to wear!<br />
if you 2 were a lot younger then my suggestion would be what happened to me in the 4th grade not long after i discovered my love of mom's silky satin long nightgowns. I never had a sister and neither parent ever bothered to fill me in on "the facts of life" or, as some call it, "have the talk". One day while playing with my neighborhood friends (back in the late 1940's you could do this) the girl next door who was a year younger than me and very pretty tells me she has a question. I replied what is it, to which she said have you ever played doctor and nurse? I replied no, how do you do that? She says tomorrow after school I'll be home alone and if you come over I'll show you. The next day we met at her house and she took me up to her bedroom and closed the door behind us. Then she started to take off the pretty dress she was wearing and I asked what she was doing. She replied by saying well the doctor has to examine me. Well this was the 1st time I'd ever seen a naked girl. Next she began taking my things off of me and putting them on herself saying now I'm the doctor and must examine you. I was the first naked male she'd seen. Lastly she takes her things and starts putting them on me saying now you'll be the nurse. How I loved the feel of her lovely satin dress
Sounds a bit sick to me.