Making boyfriend a convincing girl for halloween?

I am a 17 year old female, and my boyfriend is thin but athletic. I made a bet to a friend that he could pass as a REAL girl at the next Halloween and i want to get a early start. I have to dress him up as a girl of less that 18 years old! I need advice and help! The bet is HUGE and I don't want to loose! I don't know what to do.

He is cool with it because he gets half the money!!

he is prepared to do alot! this should be fun help me

you think i should do eyebrows and nails and all that? it would prob make it more convincing wat u think....


pictures on how i should do his eyebrows would help alot thanks

8 Answers

  • 1 decade ago
    Favorite Answer

    Wow! He sounds so cool. You could have a boyfriend and girlfriend all in one person. <giggles> Plus, you have almost a year to get him get ready.

    Face, hair, and body shape are what set male and female apart, so that's what you have to alter.

    If he's ok with it, ask him to at least shave his legs and underarms. He can always tell people that you dared him to do it, and that you both like how it feels now. As for his brows, just shape them a little. If you do too much other people may wonder. Then with make-up you can accent his eyes, contour his cheek bones, and give him nice kissable lips. Of course give him a manicure and pedicure, with polish. Unless he has to strip down around others, he could keep his toes polished all the time. Maybe with practice he could even learn to do it all by himself.

    Does he have long hair, or is he willing to let his hair grow out? A good stylist could help find a feminine style for him that could still be made to look masculine when you're not playing dress-up. His own hair will look more natural, and be less costly than a nice wig.

    For clothes, take his measuements first, so you can find sizes that fit him. If he can wear the same size as you, even better, you can 'share' clothes. Stores may frown upon him going into the women's dressing room to try things on. Maybe later you two can actually go shopping as girlfriends. <wink> As others said, it may take a bit of padding to give him a cute shape. A fully padded tee-shirt bra, with stuffing if needed, will help in the boobs department. Nothing big, just some nice, natural looking curves. When I was younger I had a padded panty to give me curvier hips and butt when i wore certain outfits. Try to find him one. Once he has some shape then you can get him some cute clothes, like you and your girlfriends wear. Remember, you want him to look like just another one of the girls. And don't forget shoes, something nice to go with his outfit. Guy shoes are just too clunky to look good, and others would notice straight off.

    Don't forget that guys act a lot differently than girls. That could be a dead giveaway that he's a wolf in sheep's clothing. When you are together have him mimic how you walk, move, and how you gesture when talking. Speaking of talking... ask him to talk softer, and with a little higher pitch, more like a girl. Make sure he doesn't overdo it though. You want him to be girly, not gay.

    Oh, for more help maybe try searching the web for sites about crossdressing and cross dressers. I bet you could find some helpful stuff out there.

    Whatever happens, I hope you two have lots of fun with this.

  • 4 years ago

    Me and a few girl friends did this to our guy friends/boyfriends, and the result can hardly go wrong. Well, for starters, wigs are always great, especially on guys, because you don't have any obnoxious pony tail lumps sticking out. Even put something on top of the wig, like a headband or something. Eyebrows, I'm not an expert on, so pay attention to other people. Jewelery is always good- get some fake pearls or other costume jewelery from target, they have tons of great stuff. Clip-on earings are also very affective. Either lend him or buy him a bra- not too large to look sarcastic/exaggerated, but about the size of a 16-18 year old. Stuff it, of course. Clothes wise, for him being atheletic, I assume that means he probably has some biceps, so don't dress him in a tank top (you'd also have pit hair problems with that) but go for something with bubblier, looser sleaves. Or a shirt-dress. Or a tailored women's blazer. Skirts are great, as well as dresses. Make him wear tights too. If he doesn't feel comfortable walking in heals, just let him wear converses, or something else unisex.

  • 1 decade ago

    Don't make him look like a whore. Apply natural looking make-up. Maybe take him in for a make up consultation at a salon, make sure they know what there doing before you make the appointment. Don't put him in a dress. Pick out an outfit you like then find it for him in his size. Buy him a bra. If he has a sister get her size (if she's big chested get 1-2 cup sizes below). Maybe a B or (small) C cup. Try stuffing it with socks or wash clothes. Once you have what your going to stuff it with, carefully put it into a nylon knee high, so it wont fall out. Tip: buy the bra before the clothes. Have his nails (toes and fingers) painted in pink. Shave his legs! Not arms, if he's not wearing a tank top, he doesn't have to shave his underarms. NO HAIRY FEET! Nice cut toenails. Primp him, like you'd get ready for the first week of school. Start about a month before Halloween on his toes and fingers. Then they'll be nice by then. Give him one of your purses, fill it with lip gloss, your cell phone, your wallet (with no money in it), and tampons (if he drops the purse when you get there, no one will know he's not a girl!)

    Source(s): The girl who wants to be a make-up artist.
  • fcas80
    Lv 7
    1 decade ago

    Well then you and he should practice every weekend. Dress him and make him up, and then take him to the mall. Have him enter a store himself, with you a distance behind, and have him pretend to shop. When he gets to the point where he can consistently shop and make a purchase without being discovered, then you know he can pass at a party.

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  • 1 decade ago

    if he has visible hips it shouldn't be too difficult. my suggestion is if he can fit your clothes get him in something really cute, you should probably do his eyebrows, but his nails may not be necessary.

    This site may be able to help some too. I use it for all sorts of things... don't forget common make-over knowledge when it comes time to do his make-up next year!!!

  • Anonymous
    1 decade ago

    Make sure he shaves his legs and also if his arms are hairy get rid of that hair too. Good luck I hope you win

  • john
    Lv 7
    1 decade ago

    he should have feminine eyebrows and dont forget to wax his legs

  • tellme
    Lv 4
    1 decade ago

    Definitely get him implants!

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