Answer: First, how comfortable are they with you being gay? Second, ask them if they would like to see you in drag. Don't surprise them unless you think they can handle it. If they are comfortable, go for it and have a gay old time. Answer: You may want to check and see if you don't mean crossdressing as opposed to drag. Drag is GENERALLY gay males dressing as women either for fun or for performances. Often this is a hyper-feminine "persona" and could be called caricature. A very good (and someone I respect heavily) example of a drag queen is RuPaul (look up on wikipedia.) He once made a comment when asked "are you a woman?" he answered (paraphrased) "How many women do you know who wear seven inch heels, four foot wigs, and skintight dresses?" Crossdressing (or transvestitism) is most often practiced by heterosexual males who like dressing as the opposite sex, but do not wish to change their sex. see "What is crossdressing."
If you are coming out as gay, there generally is no reason to get into drag UNLESS you are in a show or going out with accepting friends. Be sure you have got what you are clear and correct in your mind before you talk to anyone whom you want to trust but might be hurt by (emotionally or physically.) If you only want to dress in women's clothes (skirts, Bras, panties,makeup, blouses, high heels) then do NOT just tell people you are gay; ONLY if you find other men sexually attractive then it's up to you and a possible counselor to decide how and when to tell others. Don't be hurt if no one understands you for if you are a crossdresser: there are crossdressers who have known since they were 3 years old and can't tell you why, they just say "because." And for people who care about you, that should be enough.
{Note: heels hurt! They weren't meant for long distance walking, don't just buy these and no flats - you can scar and even maim your feet by abusing them with bad shoes. I know, I wore some sandals with 3" wedge heels and they were about 1/2 size too small, (dumb me), after 3 hours of shopping the tops of my feet blistered and years later, I still have the scars. I may not have had as bad a time if they were flats.}
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