Most crossdressers require a wig. Only the very fortunate of us can afford to keep our hair long . . . and even then there is the threat of a job interview or new significant other, etc that would necessitate chopping off those gorgeous locks. So before that day comes, you might as well be prepared with a wig. And who knows, you might find that the wig suits you better than your own hair!
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Once upon a time I had long hair myself. And I will tell you, the one thing a wig can never replace is the confident secure feel of your own hair. But a wig can let you change your hair length or color whenever your heart desires. I think those are the primary tradeoffs.
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Ok, so if you’re looking into a wig at this point there are two things to consider: natural or synthetic, and full wig or extensions. If you have moderately long hair, you might want to look into extensions. You can find clip in extensions made of natural hair that will look incredibly realistic for cheap. They take a bit more skill to apply, and they can be a bit awkward to style in some cases (especially if you want pigtails or something of the sort). Generally speaking they work best for straight hair, and if you have a lot of volume in your natural hair they will look a bit stringy and thin. So let’s assume for the moment that you’ve decided to go with a full wig. More on extensions some other time.
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Natural hair wigs provide the ultimate in realistic look and feel and can be styled to your heart’s content. They last longer than synthetic wigs, and will not get split and frazzled at the ends nearly as much. That said, natural hair also requires a lot more care and is ~10x as expensive. If you’re going to buy a natural hair wig, expect to invest some time keeping it nice (just like you would your own hair), expect to go to a salon to have it styled the first time (they usually do not come pre-cut and styled), and expect to own only one. Natural hair wigs typically cost several hundred dollars or more.
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A comparable synthetic wig can be picked up for $30-$100 (just don’t buy cheap costume wigs as they never look realistic and the fibers break quickly) and will last you several years if you treat it well. If you use and abuse it (like I do for my website), or wear it frequently (daily), plan on replacing it every year. Even with yearly replacement though, synthetic wigs will work out to be cheaper than a natural hair wig. Don’t get a synthetic expecting it to last forever though – synthetic hair pieces wear out, especially with aggressive brushing or styling. Synthetic wigs also come pre-styled . . . which can be both a blessing and a curse. You don’t have to worry about cutting them or going to a salon (you can wear a synthetic hair piece “out of the box”), but if you try to style it too much you will likely be frustrated – synthetic fibers are stiffer than natural hair and start to look like plastic (that’s what they’re made of afterall) if you pull them too far out of their preferred alignment.
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All said, I would start with a synthetic wig. Try it out, wear it a few times. Remember that you can afford to buy a few of them for the price of a natural hair wig. And if at the end of the day you decide that you really need that extra realism, then go for the natural hair . . . just make sure you know what style you want before you shell out that kind of cash!

Edit 4/28/12: YouTube shut down my channel But the good news is that I just reposted the video today – check out my updated post.
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Just uploaded, check out my new YouTube video: Makeup for Crossdressers. This instructional video goes through the how-to steps of tgirl makeup from shaving through finishing touches in high def detail. I know I’ve posted before on individual makeup tips, but I thought this video might be really helpful for any visual learners out there
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If nothing else, it’s worth taking a look at the before and after photo below to see what a difference some well-applied makeup can make. And let me tell you, I’m not a professional makeup artist, this is stuff that anyone can do at home!
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Crossdresser Makeup Before and After

At some point in time, most crossdressers will be faced with this problem – an unsightly bulge in their panties that they just can’t hide. There are many types of outerwear that eliminate the problem without any effort, but what if you want to wear that sexy mini skirt or those really tight jeans? Well don’t worry, there is a tried and true method of tucking that will eliminate all your panty bulge concerns.
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If you’ve ever tried tucking just your penis between your legs to hide the bulge, you’ve probably been quickly confronted with the issue of what to do with your testes. They’re much bigger than you realized, aren’t they? And there’s really no comfortable place to move them out of the way. Luckily, for most crossdressers there is an amazingly convenient solution – all you have to do is tuck your testicles back where they were before you were born.
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When you were born your testes were hidden safely away inside your abdominal cavity, and at some point they descended into scrotum (which is literally just a pouch of skin that holds the testes – it’s not really attached to them). They descended because sperm cells develop best at a temperature lower than body temperature. But otherwise there is no reason the testes can’t be slipped back up inside the abdomen temporarily. If you do this regularly for long periods of time, the only documented side effect is temporary sterility until your body has a chance to produce a new batch of sperm at a more optimal temperature. Don’t count on this for birth control!
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So you’re ready to try tucking for the first time? Ok, relax, lay down, and spread your legs. This will ensure the opening between your scrotum and abdominal cavity is as wide as possible. As you gain practice, you’ll likely be able to do this without any effort though. Now feel around a little to learn where the opening is. If you press your fingers gently at the base of your scrotum (“under” your penis and a little to the side) you will probably be able to feel the opening into your abdominal cavity. You may even be able to press a finger into it a good ways (obviously it’s covered by skin though, so it’s just an internal hole). You should also be able to pinch the skin of your scrotum above your testes and find what will feel like a little tube. This is your vas deferens, and you can follow that tube up to where it enters your abdomen through the same hole.
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Ok, now that you know where your testicles will be going, press the fingers of one hand against one of your testes and align it with the hole into your abdomen on the same side. Keep your fingers flat so that you are distributing pressure evenly across your entire testis and press it gently through the hole. It will likely deform a little in the process, but pop right back into shape once it’s through. No big deal. Now close that leg towards your body (this will help close off your abdominal hole on that side of your body) and open your other leg to do the other side.
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Once you have tucked your testes safely inside your abdomen, you will probably be able to feel the slight bulges of them above your pubis (the lower bone of your pelvis that crosses just above your penis). Now to keep everything in place, pull your penis tightly back between your legs. With a little luck this will work like a lid of sorts, closing off half of each hole into your abdomen – sufficient to keep your testicles inside.
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Now to hold your penis in place. I really really don’t recommend using tape. It can hurt quite a bit coming off. Duct tape for example sticks to skin astonishingly well after an hour or so and will be quite painful. Instead, just try a tight article of clothing with some spandex in it. One of my personal favorites is a good pair of pantyhose (again, go for a pair with lots of lycra / spandex). Or find some nice tight panties with a wide crotch like boyshorts, or try a gaff – a wide crotched thong made for crossdressers.
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In any event you should be quite comfortable now and have a nice smooth femme panty line. And when it comes time to let the boys back down, just untuck your penis and press gently against your testes where you can feel them bulging above your pubis. They should pop right back out and be good as new