Q&A for How to Crossdress As a Man (for Women)

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  • Question
    What about cross-dressing without my parents knowing?
    Community Answer
    You could make a habit of carrying a bag with you - blame it on how small girl pockets are. Put the cross-clothes in your bag when no one's looking. Then, when you get to wherever you're going, just run to the nearest bathroom or hiding spot and change clothes.
  • Question
    How do I crossdress without my parents thinking I'm gay?
    Community Answer
    If they find out, tell them that boy clothes are more comfortable and you feel less restrained wearing them. If they ask you if you're gay, just tell them you're not.
  • Question
    What if you have long hair and don't want to cut it or you can't wear a wig?
    Community Answer
    Pull your hair up in a low bun, but don't make it any higher than the bony nub on the back of your skull and keep it a little messy. "Man buns" are in style, after all, and makeup can help disguise any feminine features that will be exposed by the pulled back hair. You can also wear caps and other men's hats and tuck your hair up into those.
  • Question
    What if I'm found out and people think I'm gay and weird?
    Community Answer
    Then you will probably respond with natural, human emotions which are valid and important. Sometimes crossdressing can be hard, sometimes you get found out, sometimes you get hurt emotionally or physically. It's definitely a risk. Other times, you find that people are accepting, or that they just don't care, or don't say anything. It's kind of a coin toss. You can't control what other people will do, or how they will react to you. Maybe gauge the type of people you plan to crossdress around before doing so (do they seem like they would react nicely? not nicely?). Then plan and act accordingly. Prepare for any scenario.
  • Question
    Do I have to use mascara with my eyebrows?
    Community Answer
    Of course you don't. Use eyebrow pencils and mimic the hair already on your face with light strokes to make them look bigger.
  • Question
    How do I hide my large breasts (DD) without a binder, since I can't buy one?
    Community Answer
    Get a sports bra that's just a tad too small. Some larger shirts can help masking their appearance, too. A lot of it depends on the clothing you wear.
  • Question
    Can makeup help me look more like a man?
    Community Answer
    Yes, you can use makeup to make your eyebrows look heavier and even add stubble to your face using eyeliner or eyeshadow.
  • Question
    What if I have big boobs that are basically impossible to hide?
    Community Answer
    Seriously consider a proper binder. (T-kingdom makes great ones.) You'll be surprised how well they work. I know a "girl" who has large, D-sized breasts, and it hides hers perfectly
  • Question
    Is it possible to wear a ponytail if you have long hair? Will you be noticed?
    Community Answer
    You can easily overlap clothing and tuck in your hair. If this is uncomfortable, you can let it flow. With the right make-up, you might just appear like a guy with longer hair.
  • Question
    I have a very feminine, girly name. Should I change it?
    Community Answer
    It depends on what you are comfortable with. You could try a unisex name, like Chris or Robin. You can also just go by a nickname. If you do change your name, be patient with your friends and your family. It may take them a little time to get your new name right, but if you stick with it, they'll get there eventually too.
  • Question
    I have C-cups and I'm still growing, but I can't buy a binder. What else can I use?
    Community Answer
    Cut the legs off a pair of stockings/pantyhose and cut a hole big enough for your head/neck in the crotch. Wear it around your chest as a makeshift binder.
  • Question
    For a production, I need to dress as a male politician, using things I already own. How can I convincingly get that effect without cutting my hair or using a wig?
    Community Answer
    Try using a few bobby pins to hold your hair in a bun. Then, if you have one, use a hat to cover the rest of the hair. (For a politician, I would recommend a fedora.)
  • Question
    How on earth do I find men's trousers that fit my broad hips? I will probably never be able to pass as male (which is OK), but I can't even find male clothes that fit me.
    Tom De Backer
    Top Answerer
    Just keep looking: drop into some more stores, ask men where they found their clothes, browse online, ask other crossdressing people. Keep looking, and if you haven't found anything yet, you haven't looked long enough yet.
  • Question
    How would a woman cross dress as a man without sounding like a girl?
    Community Answer
    If you don’t want to sound like a girl, try taking testosterone. It lowers your voice and adds slight facial hair and pretty much makes you look like a man. If you’re not allowed to do that, try looking up exercises that lower your voice on YouTube and practice regularly until you have the hang of it.
  • Question
    How do I know if I’m transgender or just like crossdressing? I prefer the label “transgender.”
    Community Answer
    If you are transgender, that would be a permanent change but when you are crossdressing you are temporarily changing your appearance to look like the opposite gender.
  • Question
    What kinds of accessories could make people appear more masculine?
    Nico
    Top Answerer
    Watches, suspenders, belts, baseball hats, and rings are a masculine style. If you want to carry a bag with you, wear a crossbody.
  • Question
    What if I want to change so subtly my friends won't notice?
    Community Answer
    Do it slowly and gradually. Start by wearing slightly more masculine clothing a little more regularly than you used to. Don't transition too fast or your friends will probably notice.
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