Tips/Advice for a Beginning Crossdresser

[jimmy_woods]

I'm a male in his late 20's and have been interested off and on about crossdressing ever since I was a teenager. After becoming a member of this board and reading a lot of threads about crossdressing, I've finally decided to go ahead and try it out. I was just wondering if anyone has any good advice to get me started. Are there any good websites/videos/books that I should check out? What's a good place to buy clothes? Any and all advice would be much appreciated.

 

[amylin456]

I'm a male in his late 20's and have been interested off and on about crossdressing ever since I was a teenager. After becoming a member of this board and reading a lot of threads about crossdressing, I've finally decided to go ahead and try it out. I was just wondering if anyone has any good advice to get me started. Are there any good websites/videos/books that I should check out? What's a good place to buy clothes? Any and all advice would be much appreciated.

just check out / search for 'sexy clothes' and look at what you really really like.. then, depending on why you are CD'g ( want to be a girl, feel like a girl, sexual, etc...
get a start on things...

 

[Layne]

It can be a lot of fun

Not only dressing and playing dressed, but aquiring the clothing as well. I did at first, order everthing; however as time passed I began to find it more intriguing to actually go shopping for my things. Strange sensation that everyone is watching you is really erotic - but the truth be known, few if any retailers really care. Have fun.

 

[meflash]

I like to buy alot of my cloths from crossdresser.com suddenly fem. I also shop at reg stores once i found the right size for me.

 

[Hermes13uk]

How serious are you about crossdressing?

How much effort are you willing to put in to become passable?

 

[amylin456]

I like to buy alot of my cloths from crossdresser.com suddenly fem. I also shop at reg stores once i found the right size for me.

The type of clothes really makes all the difference- depending on what you are wanting.. If you think sexy and get some frumpy stuff or heels that don't fit right, then it is hard to achieve the feeling.
If you get a few high quality items and some thing you feel are very sexy , slutty, whatever you are wanting. it makes all the difference in the world..
if you shop online , they you should get a very good selection and if you know the sizes then that is a winner..

 

[emap]

Oh my guys, bad form you forgot one of the biggest thingys, makeup.

For the love of all things, do not cake it on like you see in magazines, choose it carefully and go with less is more. Now the colors really depend on two things, your eye color and your hair color. Your skin type plays a part though that is more in determining what kind of makeup you get, unless you happen to be a black man, at which point well you want light colors.

If you have blonde hair, you want darker colors, anything else you want light colors, though redheads can go with either, we are so lucky.

When it comes to rouge, what you put on your cheeks for those not paying attention, you want a pink, though you can go with other colors depending on the look you want and the time of year, in winter you want a little darker and in summer you want pink. You also want darker if you are going out at night, so your cheeks stick out more basically.

Eyeliner you can skip though black is more or less the only color you want unless you are doing an airy summer daytime look then you can match the eyeshadow. With eyeshadow, red is the black of clothes, it works on everyone for everything. Besides red though, it depends mostly on your eye color and hair color, the darker both are the lighter the color, and the reverse of course. Now eyeshadow is especially good for the less is more mentality, if you lay it on thick you look like a whore and for the most part that isn't a look you want, unless you are doing that of course.

Lipstick is the fun one, you can buy every shade under the sun if you want. I'm not gonna tell you how to put it on, there are thousands of websites with methods of applying. I'm just going to say lipstick is where you put your own personal spin on your look. If you are feeling light and airy, put on a light and airy lipstick, skyblue, pink so on so forth. Red is still the works with everything of course though unless you are a black man you want a darker red.

Just in case, a black man the only colors that will work are the lighter ones, the darker the color the more it blends in with his skin. Granted this is variable, I know not all black men are black they are brown and sorta tan, but basically the darker the skin the lighter the colors must be.

 

[amylin456]

Oh my guys, bad form you forgot one of the biggest thingys, makeup.

For the love of all things, do not cake it on like you see in magazines, choose it carefully and go with less is more. Now the colors really depend on two things, your eye color and your hair color. Your skin type plays a part though that is more in determining what kind of makeup you get, unless you happen to be a black man, at which point well you want light colors.

If you have blonde hair, you want darker colors, anything else you want light colors, though redheads can go with either, we are so lucky.

When it comes to rouge, what you put on your cheeks for those not paying attention, you want a pink, though you can go with other colors depending on the look you want and the time of year, in winter you want a little darker and in summer you want pink. You also want darker if you are going out at night, so your cheeks stick out more basically.

Eyeliner you can skip though black is more or less the only color you want unless you are doing an airy summer daytime look then you can match the eyeshadow. With eyeshadow, red is the black of clothes, it works on everyone for everything. Besides red though, it depends mostly on your eye color and hair color, the darker both are the lighter the color, and the reverse of course. Now eyeshadow is especially good for the less is more mentality, if you lay it on thick you look like a whore and for the most part that isn't a look you want, unless you are doing that of course.

Lipstick is the fun one, you can buy every shade under the sun if you want. I'm not gonna tell you how to put it on, there are thousands of websites with methods of applying. I'm just going to say lipstick is where you put your own personal spin on your look. If you are feeling light and airy, put on a light and airy lipstick, skyblue, pink so on so forth. Red is still the works with everything of course though unless you are a black man you want a darker red.

Just in case, a black man the only colors that will work are the lighter ones, the darker the color the more it blends in with his skin. Granted this is variable, I know not all black men are black they are brown and sorta tan, but basically the darker the skin the lighter the colors must be.

Wow emap, that was great.. really good information..
would be nice to have someone around who is so experienced and helpful.
Thanks.

 

[emap]

No problem though you don't need someone around who can do makeup, you just gotta practice, hence the keep it simple and less is more. Unless your job is to put makeup on people it is difficult at first, just try to not get frustrated, everybody has ended up with a clown look at one point or another.

Mine was the first time, though my mom at the time was heavy into the bases and such, when she stopped laughing. Took way to long mind, though I laugh about it now, she taught me how to do it and without the bases. I did wear them but I was a teenager and breaking out and bad time over all. Anyway, just make sure less is more is your mantra, you really only need three peices of makeup in your purse, eyeshadow, rouge and lipstick, the rest of it is for actresses and whores.

 

[amylin456]

should one use foundation ?? not sure how it works, sequences etc. have done a little rouge and of course lipstick... tried eye shadow and couldn't get it right- but it starting looking sexy,, lost patience

No problem though you don't need someone around who can do makeup, you just gotta practice, hence the keep it simple and less is more. Unless your job is to put makeup on people it is difficult at first, just try to not get frustrated, everybody has ended up with a clown look at one point or another.

Mine was the first time, though my mom at the time was heavy into the bases and such, when she stopped laughing. Took way to long mind, though I laugh about it now, she taught me how to do it and without the bases. I did wear them but I was a teenager and breaking out and bad time over all. Anyway, just make sure less is more is your mantra, you really only need three peices of makeup in your purse, eyeshadow, rouge and lipstick, the rest of it is for actresses and whores.

 

[infinity706]

No problem though you don't need someone around who can do makeup, you just gotta practice, hence the keep it simple and less is more. Unless your job is to put makeup on people it is difficult at first, just try to not get frustrated, everybody has ended up with a clown look at one point or another.

Mine was the first time, though my mom at the time was heavy into the bases and such, when she stopped laughing. Took way to long mind, though I laugh about it now, she taught me how to do it and without the bases. I did wear them but I was a teenager and breaking out and bad time over all. Anyway, just make sure less is more is your mantra, you really only need three peices of makeup in your purse, eyeshadow, rouge and lipstick, the rest of it is for actresses and whores.

That's great and all, but what about the guys like me that prefer women without makeup? There's something really nice about that natural look. Of course, if it helps your confidence to wear makeup, go for it. It's not that big of a deal.

 

[amylin456]

That's great and all, but what about the guys like me that prefer women without makeup? There's something really nice about that natural look. Of course, if it helps your confidence to wear makeup, go for it. It's not that big of a deal.

well, it can us gurls to look a litter hotter, but guess it depends on what you are looking for..

 

[infinity706]

I actually prefer the natural women that don't feel like they need makeup, fake fingernails, waxing, and all that. Of course, like I said, it's certainly not a deal breaker, so if it helps your confidence, go for it.

 

[amylin456]

I actually prefer the natural women that don't feel like they need makeup, fake fingernails, waxing, and all that. Of course, like I said, it's certainly not a deal breaker, so if it helps your confidence, go for it.

do you understand what thread you are on and the subject ??

 

[infinity706]

Yes, I understand. It would apply to guys dressed in women's clothing, as well. I don't just mean actual women.

 

[emap]

should one use foundation ?? not sure how it works, sequences etc. have done a little rouge and of course lipstick... tried eye shadow and couldn't get it right- but it starting looking sexy,, lost patience

Sorry I wasn't clear, foundation, base, there is another name I can't think of at the moment are all makeup you put on before anything else. Really the only time you need one is when you have blotchy skin, a bruise or zits. You know stuff you don't want to be showing. It is also good if you are cursed with oily skin because most rouges and eyeshadow won't hold to oily skin without a base.

They do make rouge and eyeshadow for oily skin with no base, I don't recall what it is called. Foudnation or watever you want to call it are only need to hide something, or to change your skin color, goths use foundation, or was it emo now I can never remember. Unless you are going for a specific look, or have blemishes you want to hide, do not use foundation, just get the rouge powder, eyeshadow, powder is best because it does not block your pores and lipstick. Look at each kind of lipstick as well, some are only good for certain things, like daytime use or nighttime use, some are safe to eat/drink with some are only safe to drink with, I don't know how that worked. they come in powders, brush on and the classic tube now, usually the best choice is the classic tube, Revlon makes an all day that works quite well if a little limited in the color category.

If you don't want to look through oodles of online sites selling lipstick, go to a store, walgreens is good for this and simply ask about the different ones, you can say it is for you or a girlfriend. The staff is mostly not caring one teeny iota if you are a guy dressing as a woman, they just want something to do and well talking to you and answering questions is better than standing around or being told to do something by the manager.

 

[naughtyinsilk]

If you look on Youtube there are a number of How To make up instructional videos.
thus is a simple but good one and there are many others

http://www.youtube.com/watch?v=aHDJDyZXKG0

Becareful of your eyes if you spend a whole evening trying out different makeup looks, too much eye makeup remover may cause you to get irritated or even infected eyes. Sounds obvious but always wupe off makeup away from the eyeball to the outside of the eyearea, dont just rub all over the eye area.

Buy the branded makeup if you can, a few good buys will look a million dollars, alot of cheap stuff, may cause allergic reactions and spots.

Liquid eyeliner i find better than pencils, a plumper lipstick improves a look too. But before you buy any look at women with similar skin colors and hair color to you, see what looks good on them, use the people you meet as a color guide, and remeber if you wear a wig that isnt your natural hair color you will need to alter your makeup colors accordingly.

If your nervous about buying makeup , use ebay, same goes for lingerie etc, it can be much cheaper than specialist sites.

 

[amylin456]

Sorry I wasn't clear, foundation, base, there is another name I can't think of at the moment are all makeup you put on before anything else. Really the only time you need one is when you have blotchy skin, a bruise or zits. You know stuff you don't want to be showing. It is also good if you are cursed with oily skin because most rouges and eyeshadow won't hold to oily skin without a base.

They do make rouge and eyeshadow for oily skin with no base, I don't recall what it is called. Foudnation or watever you want to call it are only need to hide something, or to change your skin color, goths use foundation, or was it emo now I can never remember. Unless you are going for a specific look, or have blemishes you want to hide, do not use foundation, just get the rouge powder, eyeshadow, powder is best because it does not block your pores and lipstick. Look at each kind of lipstick as well, some are only good for certain things, like daytime use or nighttime use, some are safe to eat/drink with some are only safe to drink with, I don't know how that worked. they come in powders, brush on and the classic tube now, usually the best choice is the classic tube, Revlon makes an all day that works quite well if a little limited in the color category.

If you don't want to look through oodles of online sites selling lipstick, go to a store, walgreens is good for this and simply ask about the different ones, you can say it is for you or a girlfriend. The staff is mostly not caring one teeny iota if you are a guy dressing as a woman, they just want something to do and well talking to you and answering questions is better than standing around or being told to do something by the manager.

Really helpful advice.... thank you...

 

[emap]

Listen to naughtyinsilk as well, those video's are great for new people to applying makeup, I believe you can on occassion find make up tips from the professionals, those are very good when you are dealing with zits, blemishes or bruises. Also keep in mind, the more makeup you put on the more chemicals seep into your skin, you want at least one entire day makeup free a week. More is better of course but that is rather easier said then done for a crossdresser or transsexual, I don't think they can feel like a woman without makeup.

Trust me on this, they are not alone there are women who do not go a day without makeup from the time they are 12 until they die basically. They are easy to spot, if you see a 30 year old with zits they never go without makeup, I have seen them in the pool, with the skull cap for their hair and swim with their head above water.

 

[amylin456]

emap, you are very sweet and helpful. for those of us who don't dress everyday. and it is not a daily makeup routine it is easier on the skin.. Getting the right tones seems so hard. i have practiced a bit.. I'm asian, so I have a different starting skin tone. I think my eyes come out okay with pencil and lash- easier I think because my eyes have aslant and extending out and some blue eye shadow ( which I find frustrating to apply) come out pretty good- but it takes a long time it seems..
Foundation / rouge , highlights I find much harder, trying to accent parts.. lipstick-- ummm that is the easiest and kinda the funnest as well. Using the Kleenex the old fashioned way to daub lips is so sexy....
I continue to thank you for your tips etc..

Listen to naughtyinsilk as well, those video's are great for new people to applying makeup, I believe you can on occassion find make up tips from the professionals, those are very good when you are dealing with zits, blemishes or bruises. Also keep in mind, the more makeup you put on the more chemicals seep into your skin, you want at least one entire day makeup free a week. More is better of course but that is rather easier said then done for a crossdresser or transsexual, I don't think they can feel like a woman without makeup.

Trust me on this, they are not alone there are women who do not go a day without makeup from the time they are 12 until they die basically. They are easy to spot, if you see a 30 year old with zits they never go without makeup, I have seen them in the pool, with the skull cap for their hair and swim with their head above water.

 

[emap]

Oh careful of the mentioning of slanted eyes, that is apparently offensive.

Anyway, like I mentioned red is the color of choice for makeup when you are not sure go red. How long it takes depends on where you are going, if it is a day trip just a couple dabs of rouge and you are set, if you try and highlight your cheek bones you will look like a whore. Which could be nice if you want sex I suppose.

I digress, lipstick, well really you sorta just outlined it, you apply it to one lip, press your lips together and then take the paper towel or toilet paper, toilet paper leaves more and press your lips together again, gives you a sort of wet lip not lipsticked look. Well depending on the color, most colors scream lipsticked anyway, though it is rather the point.

Ok, asian is actually fairly easy, you are either pale skinned or slightly yellowish, more or less equals out to the same depends on where your ancestors came from, Mongolians are darker skinned than Chinese and Japanese are practically white. In between is a mixture though I don't think china or japan would admit to being related let alone any of the small countries in between.

I digress again, I am bad today. So since you have dark hair, unless you dye it then feel free to ignore me and light skin you are fairly easy, you want lighter colors, sky blue base red at most, the light colors are what you want at any rate, pink is especially good, eyeshadow is really any light color you want though blue, green and red/pink are the best, rouge you want pink, lipstick you can go with any color really, dark is especially good if you want to bring eyes to your lips and breasts. If you want them to look you in the eyes you want a light color to complement the eyeshadow, if you say get large fakes or a boob job, still fake just internal fake then it won't matter what you put on your face besides maybe a neon sign.

 

[amylin456]

Thank u emap.. gosh, I have slanty eyes , and I'm not offended at all..
anyway, I tried just a bit and found that light rouge, pinkish, with touch of almond on my cheekbones looks pretty good .
On the eyes, accentuating a bit seems to look sexy ( hard to judge by yourself).. and lipstick is so easy. I can go from fiery red to a soft almost orange gloss..

Oh careful of the mentioning of slanted eyes, that is apparently offensive.

Anyway, like I mentioned red is the color of choice for makeup when you are not sure go red. How long it takes depends on where you are going, if it is a day trip just a couple dabs of rouge and you are set, if you try and highlight your cheek bones you will look like a whore. Which could be nice if you want sex I suppose.

I digress, lipstick, well really you sorta just outlined it, you apply it to one lip, press your lips together and then take the paper towel or toilet paper, toilet paper leaves more and press your lips together again, gives you a sort of wet lip not lipsticked look. Well depending on the color, most colors scream lipsticked anyway, though it is rather the point.

Ok, asian is actually fairly easy, you are either pale skinned or slightly yellowish, more or less equals out to the same depends on where your ancestors came from, Mongolians are darker skinned than Chinese and Japanese are practically white. In between is a mixture though I don't think china or japan would admit to being related let alone any of the small countries in between.

I digress again, I am bad today. So since you have dark hair, unless you dye it then feel free to ignore me and light skin you are fairly easy, you want lighter colors, sky blue base red at most, the light colors are what you want at any rate, pink is especially good, eyeshadow is really any light color you want though blue, green and red/pink are the best, rouge you want pink, lipstick you can go with any color really, dark is especially good if you want to bring eyes to your lips and breasts. If you want them to look you in the eyes you want a light color to complement the eyeshadow, if you say get large fakes or a boob job, still fake just internal fake then it won't matter what you put on your face besides maybe a neon sign.

 

[jimmy_woods]

Wow, lots of good advice about applying makeup. That should really help out since that's something I have completely no experience with.

Anyone have any advice on any other aspects of crossdressing? Are there any tricks to picking out clothes or do I just go with whatever makes me feel/look good?

 

[emap]

Well clothes is a little easier, if you want to dress up and look like a gal going out on a date or looking to hook up, you should check out the plus size sections of the regular stores or the crossdresser websites. Unless you are a petite guy of course, if you are a petite guy you can easily wear just about anything, otherwise you need to wear the larger clothes. Crossdresser specific stores would be easier to get clothes from that fit you, though really any walmart or sears or whatever would carry dresses that fit.

 

[amylin456]

Well clothes is a little easier, if you want to dress up and look like a gal going out on a date or looking to hook up, you should check out the plus size sections of the regular stores or the crossdresser websites. Unless you are a petite guy of course, if you are a petite guy you can easily wear just about anything, otherwise you need to wear the larger clothes. Crossdresser specific stores would be easier to get clothes from that fit you, though really any walmart or sears or whatever would carry dresses that fit.

excellent insight and advice...