Starting to Crossdress?
918533
The easiest thing for you to do is talk to your sister and explain to her about your desire to dress feminine and ask her to help you find the right size and right outfits.I bet you anything she will be glad to help you with everything
623999
Move?\n\nHow can you be a cross-dresser if the dress is the same?\n\nBuy some western lingerie.  Wear it under your clothes.
150405
ok guy, you are not alone, my mother wanted a girl also,i have been dressing  as a woman for several yrs now and if you do not try to work something out you will form a female side which will get stronger the more you dress. myself,i have learned to deal with it and i do enjoy it. you have to control the female side or it will take control of you.as far as wearing heels it gets easy as you wear them. wearing a skirt with hose is ok.note, if you are wearing a bra your breast will form to the bra, so be careful unless you want to form breast.you are young enough to deal with it now, do something or you be a crosdressed as  i am. if dicide to keep dressing up for your mother you will lose to your female side and turn out as me. be smart,it turns into hell at times, you are the only one who can control your body, the other girls are right,make a choice now.within a year if your still dressing you will be hooked as i am. good luck again
285450
Most females who dress like that right now tend to be gay.  That is the message you will be sending if you adopt that style of clothing.  If you are not gay, I wouldn't recommend it.\n\nIf you want to find a good metro look watch the most recent black videos on TV and pick something more current for women.  Be careful.  Many background dancers are actually strippers and use these videos to advertise themselves.  Try not to emulate one of them.
547656
wear a skirt cute top and some cute shoes idk
1004441
ditch the silk buddy and go for jeans. \n\nBe coo..
74458
Many (MANY) years ago when aristocratic ladies would get dressed, they didn't do it themselves.  They had assistants to aide them in closing the numerous fastenings, buttons, clasps, and so on.  It was much easier (or so someone thought) to help someone get dressed if the buttons were reversed (to the wearer) so that it would appear as "normal" to the helper.  Easily verified, if you are male then find a female shirt and rather than put it on, try to button and unbutton it from the outside.  If you are female then try taking one of your shirts and working the buttons from the outside as though you were helping someone else get dressed; to you, it should be very akward.  \n\nSorry but your name doesn't give away your gender and you have no avatar.  Come to think of it, I am in the same boat.\n\nAlso, if you are a guy and you try the part about unbuttoning a girl's shirt from the outside and seeing how easy it is, one word of caution....if occupied by the owner, be real sure you are allowed to....hehehe
363205
first take off your clothes
634929
www.vivcore.com has some really neat-o clothes. Welcome to the world of looking good; we girls get to wear what we feel like. Did you see that one retro-fifties dress with the tattoo print? Wow. Anyway, read some Ranma 1/2 comics and prepare for a new life and new(better) wardrobe! Ta ta! (Skips away)
189240
You are a work in progress.  Not necessarily gay but right now you like crossdressing.
93475
If you caught your friend admiring your wardrobe, firstly you should be flattered :o) The fact that he's asking you to "dress him up" is a show of how deeply he trusts you.  He's feeling safe enough around you to reveal what some consider a deep and dark secret. You must be a good friend! I would suggest that you figure out if you're comfortable doing this with him. It's ok to say "no" if you aren't comfortable. \n\nIf you are comfortable doing this, keep in mind this experience is probably going to give him a thrill, so it's best if you don't laugh at him or take pictures and post them on the internet or anything like that. He'll be hurt and it may destroy your friendship. \n\nMaybe it would be better if you helped him to purchase clothes for himself, this way he can wear them whenever he wants to. He could become dependant on the fact that you'll let him raid your closet. As with any friend, male or female, there's only so much sharing out of the closet that a person can take. Oh and skirts with the elastic waists work for most sizes and shapes. Maybe flats (unless he knows how to walk in heels). Good luck.
550021
Well well well. What have we here I dont think you are gay however you are on to something a cross dresser maybe? I blame your sister for it for dressing you up. You are also responsible however. What 8-9 year old boy lets himself play dress up. At that age girls were a no no. Qooties remember. I didn't think so. There is a Different point of view. You are at an age where you become sexually aroused by things. Not suggesting your sister thats incest and a very big no no. What you need is a girlfriend that has the bras and panties and wears tham and you get to see them. I think girls look alot better than guys in those at least to me a straight guy. I have no problem with gay people I just not wired that way and never will be. Stop doing it and get layed and become a man grow out of the dress up thing or keep it as a fettish. What ever floats your boat.
849042
Well, most crossdressers are not gay, so it's not surprising he likes women.  And I can see a crossdresser feeling attraction for somebody who understands some of the stress/issues that come with crossdressing.  It's kinda like something they share.  Also, he may feel less intimidated and less likely to get ridiculed if the object of his attention is somebody who has the same hobby he has. Be happy for him. I am :)
258984
I would start out with a simple classic look so as to blend in before getting too trampy or trendy.  One should get used to dressing as a woman before they start pushing the limit. Also just start out with heels no higher than 3".
1168840
learning 2 wear clothes , ehh
980696
As long as you look dressy and you feel good, go for it. Now jeans may not be your best bet but anything else would prob work great!    \n:-)
472349
Take is slowly. Define yourself first. What type of crossdresser are you? Casual, all the time? Do you dress as a fetish, or is it deeper for you? Have you talked with anyone else about your crossdressing? \nWhat are you hoping to accomplish by telling her? If you are looking for support, what are her views of other crossdressers? In today's say and age, you see crossdressing on all sorts of TV programs and other media, I am sure she has seen it as well. What is her general reaction towards it. Who's clothing do you wear? If it is your own stuff, how well hidden is it? You might be suprised, she might actually already know and be waiting for you to trust her to tell her.\nTake it slow, because if she is not ok with it, she might have a lot to process. I would make sure to inform her that you are not GAY, and by wearing clothing like that, it does not make you in any way GAY.\nIf you trust her, and she trusts you, and you want to tell her after you have found out who you are, then go ahead.\n\nI am not sure how well this would work, but you might make a game out of it, or a bet. Maybe do something that she comes up with you dressing up, like set a bet where the looser has to dress as a maid or something, and be all macho about it so when you loose, it looks painful that you have to dress as a maid. Heard that one somewhere, not sure the results. Would give you a deep insight into your wife's view on crossdressing from her reactions though...