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Interested in getting into cross dressing/drag

Discussion in 'Coming Out Advice' started by J Snow, Aug 25, 2011.

  1. J Snow

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    So, to keep this brief, I recently had a great conversation with my bf about how I have a lot of desire to be more feminine then I am, and I thought that cross dressing would be a great way to express that in a healthy way. I kind of expected him to think it was silly since I'm kind of big (5'11" 220 lb. or so) and not really that feminine (in my opinion).

    He was super supportive though and seemed sincerely excited to help me with this new experience. He's clear he likes my masculine side too and wants me to maintain that, but he's been otherwise about as excited for this as I am. Idealy if I ever get comfortable with it, I would even like to do drag, but I'm getting way ahead of myself.

    I don't really know where to start with this. I don't really have any girl's clothes or make up or anything. Don't really have one question I'm trying to ask, but anyone that's more experience got some friendly advice? Tips? Thoughts on how to find supplies cheap? Whatever else could be worth throwing out there lol?

    Also, I don't even feel comfortable dancing in a club, I have a hard time imagine I'd be able to in front of a whole crowd in drag. =/
     
  2. Veronica

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    Physically male dress in women's clothing for a whole range of reasons from fetishism to an expression of identity for women trapped in a male body. My reason, to the extent I do it at all, is in the latter range, so my advice is limited if the reasons are more ... uhm... exhibitionist?

    I have a few items I bought online, jeans and tops and such. Since I have a bit of a passion for shoes, I have a few pairs. I don't do the make-up bit as I just dress according to mood and make-up has never interested me much.

    I have had no problem finding stuff that fits online. I am a bit taller than you, but probably a lot skinnier or smaller built. I haven't exactly been ravaged by testosterone if you know what I mean :stuck_out_tongue_closed_eyes:
    Keep in mind that women's clothes are designed for a different body build than ours. I have no ass, so I wear smaller size on my lower half than upper for instance. Some stores also have items with a male cut for that reason. The only one I knew of online no longer exists, but since I don't jave a problem finding stuff that fits, I haven't really looked into this.

    I fit into regular sized shoes too. This is often another problem for guys. Again there are stores that have shoes in larger sizes. Just google I suppose. Also, I'd advice against going out in heels if you have no experience wearing them. It can be quite easy to injure yourself. There are plenty of young girls out there that can't pull of walking in heels either for that matter.

    Also, a last point, buying a second wardrobe is expensive. And buying a female one even more so! So I spent most of the time window-shopping online. To save yourself some money from buying wrong stuff, look up how women's sizes are defined and measure yourself and find the right ones. At least for shoe sizes, you can just look up wikipedia. Rest just google.

    Oh, and also, get help from a female friend if you know any that wouldn't mind you asking. Especially if you want to do the whole make-up thing.

    Hope that helped a bit :eusa_danc
     
    #2 Veronica, Aug 25, 2011
    Last edited: Aug 25, 2011
  3. Katelynn

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    I'm about 5'10' & 197 lbs, so I'm a little in the same boat a bit as you. veronica is absolutely right! Find a female friend who has some good fashion sense & bring her along clothes shopping with you, she'll be able to help you with sizing & what will & will not look good on you. I know when I first came out to my friend Steph, her first desire was to do a whole makeover.transformation nite for me so she could just totally go insane making me girly! Believe me, a feminine touch is very much necessary when starting out. Also, before you even go out shopping, get your measurements & take the with you to the store so you know you'll be buying things that will fit, especially underwear, because if you have the wrong size garment, you may not be able to return it (especialy underwear), meaning you've wasted a bit of money. Also before going out & hitting the boutiques, spend a little time online looking at some of the styles of clothing out there, see what appeals to you & what might appeal to your bf (since you're including him in as part of your crossdressing) & see what you might want to keep an eye out for. Lastly, if you're going to build a feminine wardrobe up, try thrift stores & bargain stores, where you can spend a decent amount of money & get a fair amount of things! Other than that, have fun!!!
     
  4. txnathrt

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    I don't know a thing about make up or cross dressing ( sorry! ) but I did want to say thrift stores and goodwill are the best for variety, sizes and trying out new styles and choices in wardrobe without spending a million dollars! And the size ranges are amazing!
     
  5. Vivien

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    My whole experience with it has been my girl friends. I mean a couple people said it already, girls are they way to go they have been doing it for a very long time. So maybe if you have a friend that is around your size you could try things out to see how things fit to your specific body. like me for example I have a little hip and a big butt but im only like 5"7 and weigh 140. everything fits different for different people so like kiersten said get your measurments and you can always have thing tailored if you want to pur a little extra money in.. hope i was helpfull
     
  6. J Snow

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    I'm kind of pressed for time right now so I can't reply in detail to everyone's posts, but I want to thank everyone for the helpful and supportive advice.

    My bf has done drag at least once and he knows people that do it regularly so I think he'll be a great help. Unlike every other gay guy on the planet though, practically all of my friends are straight guys, and even if I did have more female friends, I think I'd have a hard time fitting into their wardrobe.

    I'm not really sure why I have such a strong desire to do this, but I do know one of the first things that made me question my sexuality was a strong desire to pretend to be a girl online before I had even gone through puberty, followed by a strong desire to actually be a girl off and on for most of my time through middle school and high school. I never felt uncomfortable as a man, so I don't really think I'm trans though. I guess part of this is to figure that out and express a different side of myself so it doesn't conflict with my normal personality and behavior.
     
  7. Noir

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    Even if you don't consider yourself too feminine looking, I think you should still cross-dress if you really want to. ^-^ And I agree, take a female friend with you who would know what you look good in, and if you want to ease into it a bit maybe start out with wearing things that are still for girls but aren't exactly too feminine, either. Something more unisex, you know? Then again, you might want to just dive in head first--what do I know? lol Good luck!
     
  8. TheEdend

    TheEdend Guest

    I don't really know much about it so I can't help you there, but just wanted to say that I think its awesome that you are putting yourself out there and allowing yourself to explore whatever feelings you are having. Go for it and don't look back! :slight_smile:

    I think one of the things to keep in mind is that you don't have to look identically as a girl if you don't want to. Drag or crossdressing has many, many variables in there.

    Just as an example, here is a group that does some charity work around my area in a unique way:

    [​IMG]
    [​IMG]
    [​IMG]
     
  9. J Snow

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    Okay, I've been staying at my boy friend's mom's for the the last couple of nights, so I haven't really had a lot of time to reply in detail to people's comments.

    First of all, last night we went to Walmart and picked up some make up. It was about 15 bucks and got some lip gloss, concealer, eye shadow, eye liner, and mascara. He showed me how to put it on. It was a positive experience even though there wasn't really a mirrior we could use in the basement so I just kind of had to take picture of myself and look at them to see how I looked.

    It kind of made me just jealous of women that can wear it in public and have it be normal lol. But my bf actually said it looked really sexy even without dressing up, and I actually thought it looked good in the pictures. I guess I'm just a little confused about where to go with this, and I know even though my bf likes it, he has a lot of worries about it too. He doesn't want me changing on him, and I think he's even more skeptical about doing anything sexual with it. He's told me he's afraid I'm going to move away from making progress on coming out with our relationship, and start with coming out on liking to dress up, but that doesn't really make sense to me.

    I gave my bf the money to buy the make up, but just browsing through the isle and walking through check out with him made me feel a little uncomfortable. It was worth it though.

    TheEdend- I know that a lot of people cross dress and don't actually look female, but I really am interested in being able to. I doubt I'd ever be passable in public, but I'd least like to be able to go to a gay bar or something and look feminine instead of just a man in a dress. No offense to the people in your pictures, I have the utmost respect for someone with the courage to do what they want no matter what they look like. That just wouldn't be for me. That being said, I think if I just worked on losing a little belly fat, it wouldn't be incredibly difficult aside from my height and shoulders.

    edit: Also, I'm kind of tempted to post the picture of me in make up so people could see how it turned out and give me their honest opinions about if I could be passable or whatever, but I'm very skeptical about posting a picture like that on the internet...
     
  10. StarofMiyu

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    *giggle* That's really cute, but ifyou really wanted to look feminine in a gay bar or something you would have to put makeup on your face too (sorry if it's there and I didn't notice it) You have tomake your face look smooth and do it properly so you can't really see the chin too well...xD
     
  11. J Snow

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    Can you be a little more specific about "putting makeup on my face" or how I could make my chin less noticeable? Also, I appreciate you saying its cute =) I really want honesty though. This isn't the kind of situation where I would want people to say I look good, so I do it at a gay bar or something and really everyone is just laughing at me.
     
  12. StarofMiyu

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    Kind of hard to explain with words, you have to...ugh <_< I don't remember the colors but I remember how...you have to make your face look smooth. As for your chin, you can put some concealer and smooth it out like the rest of your face, because you're unlucky and have one of the chins with an icky line down the middle ):
     
  13. J Snow

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    Well I know my bf put some concealer on my face, but I don't remember if he put any on my chin. I was surprised I really wasn't able to feel it at all. I think it was on my chin though, it was lighter then my actual skin color so I think he just put it everywhere. Also I hadn't shaved my face in a couple days when that picture was taken either.
     
  14. Revan

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    Tbh, kinda wish my bf were as supportive, he doesn't really have the greatest opinion of drag queens...:frowning2: But good luck! One thing I found when I at least first thought of trying it, a friend suggested to me I should get a drag mother, to teach me the ropes.
     
  15. J Snow

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    Well my bf I think has mixed feelings about it, but I might have mentioned that higher up. I don't really remember...
     
  16. maverick

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    Those pictures are awesome sauce.

    Jon Snow, a few things:

    1. You have BEAUTIFUL EYES AND SKIN. *drool*

    2. You might want to experiment with lip liner and eye liner. I think both would give you more definition. And I think the lip gloss you have on there is a little pale for your complexion (it casues your lips to kind of blend in with your face). You might want to go with something that has a little more color.

    3. In your eyeshadow, there are three major areas you need to hit - the part of the eyelid which is directly over your eyeball (which should have the darkest shadow), the crease (which should have a medium shade) and the arch beneath the eyebrow (lightest shade). Ideally, these three shades should graduate evenly from darkest to

    4. Needs mascara.

    5. Be careful about getting eyeshadow beneath the eye.

    6. Instead of wearing eye shadows that match your eye color (green with green, blue with blue, etc...) you should wear eye shadows that are the opposite of your eye color on the color wheel. For your eyes, I'd probably try out some bronze or gold-looking eyeshadows, tans, and browns. It will cause the blue-green in your eyes to pop.

    Ex. [​IMG]

    (When I was trying to make myself more feminine, I got really good at wearing makeup and got complemented on it all time. Helped that I was a painter first. :grin: )

    ---------- Post added 29th Aug 2011 at 06:27 AM ----------

    [​IMG][/IMG]

    ^ Here's an example of the look I'm talking about.

    ---------- Post added 29th Aug 2011 at 06:28 AM ----------

    ^ to lightest. :stuck_out_tongue_closed_eyes:
     
    #16 maverick, Aug 29, 2011
    Last edited: Aug 29, 2011
  17. J Snow

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    Maverick, your post actually meant A LOT to me. I posted those pictures on a different site, and while the comments weren't rude, they definitely kind of brought me down more then I would have expected from little things. They said I looked like a 90's drag queen, with way too much makeup, a wide face, bedroom eyes, idk... That's not want I want, I want to at least look close to "passable."

    What confused me about your post is that I've already done a lot of things in those pics that you mention. Like....

    1. Well I am wearing concealer in that pic, and I know what the people on the other site when they said I have "drag eyes" in that pic. I don't know how that turned out that way...
    2. Well I'm already wearing eye liner in that pic. Thank you for the lip gloss advice though. I don't really like my normal lip color because it seems really pale and to blend in my face normally like you said. That being said, I think I do like that color cause its subtle, and it looks like something a girl would wear in a normal casual situation. That's how I feel anyway.
    3. Again, this is what I tried to do. Except for the color order that is. The box actually said to do pink for the eyelid, black for the crease, and silver for the brow bone.
    4. Wearing mascara (I'm starting to think I didn't put some of this stuff on right if you can't see it... Granted they are phone pics...
    5. Yeah I am having a hard time with this one, granted I think what you might be seeing in that pic is just bags under my eyes =/ Which speaking of which is there anything I can do to make that less noticeable? Aside from sleep more lol, I kink of always have them....
    6.I'll have to try that. Thank you =)

    So, honestly after messing around with it a little bit, I really think the eye liner looks good just with me in guy mode. And since that lip gloss doesn't stand out too much, I don't think it would be half bad of an idea for me to wear something like just the eye liner and lip gloss at a gay bar or something like that. Anybody have any opinions on that? Good idea? Bad idea?
     
  18. maverick

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    Dude, for your first try, I don't think you did bad at all. I'm into femmes and I would have batted eyes at you if I saw you in the club. And what the hell is wrong with bedroom eyes, might I ask? :icon_wink

    I can tell you're wearing concealer, and I think it looks good. I'm not entirely sure what "drag eyes" are, but if it's over-the-top colorful eye makeup, then yeah, that's pretty draggy. If you read any Cosmo or girly magazines, you'll see that makeup is trending these last few years towards "natural" looks, but I think that they might end up being a little too natural on you - that is, I don't think they're going to make you look feminine enough. You need night makeup, not day makeup, to pull off drag. Otherwise you're just going to look like a very pretty boy. :grin:

    What color did you use? It's kind of hard to tell. For your eye color I would suggest looking for a dark brown eye liner, and just using it on the top lid (I personally think eye liner on both top and bottom looks like overkill, but if you can work it, go for it).

    Black, pink, and silver? Weird color combo...did it come in one shell? I'm just curious, I've never seen that mix together before.

    I think this actually would have looked better without the black in the crease. As you blink your eyes, whatever color is on the crease gets distributed, and if it's black getting dusted over light colors like silver and pink, you're gonna get smudgy... :stuck_out_tongue_closed_eyes:

    Yeah, this might be part of it, it's probably more obvious in person. My only suggestion here is to probably give your lashes a few coats, especially if they're light-colored or sparse. Barring that, you could always give falsies a whirl for fun too.

    Cheap way ($2): Slices of cucumber on your eyes.
    Expensive way ($15+): Can't go wrong with Olay products, they are really good quality in my opinion and actually work. Olay Definity is what I use for my eyes (and yes, that is the girliest thing you will hear me say this month):

    [​IMG]
    [$15.99 retail]

    Sounds like a plan to me. Honestly, I don't understand why more guys don't try wearing concealer/foundation, eye liner, and lip gloss. Those three products look good on almost everyone, regardless of gender.

    [​IMG]

    I rest my case.

    Granted, I don't wear any makeup like eye shadow and all that girly stuff anymore, but as far as the "age-saving/beauty routine" products like Olay puts out, straight up both men and women should use those. The lotions and moisturizers really do help protect your skin and keep it looking fantastic. Plus a lot of them have sunblock in them.

    Oh, one thing I forgot - do NOT sleep in your makeup, even if you get home drunk at four in the morning and don't feel like taking two minutes to get it off. It's bad for your skin and gets your pillow dirty. *bleck*

    Hope that helps. :kiss:
     
    #18 maverick, Aug 29, 2011
    Last edited: Aug 29, 2011
  19. Veronica

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    I thought you looked pretty good for a first try.

    I'm no expert on this anyway, but got a bit inspired to be honest :stuck_out_tongue_closed_eyes:
     
  20. SaphireMoon

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    well if you want some tips there is an amazing drag how to video that i can try and find again for you