Crossdressing 101 – How to Become a Sissy

[table id=2 /]

Crossdressing Clothes…  Here is one the simplest question for most aspiring crossdressers and yet also one of the biggest obstacle for any man who wants to indulge in the art of cross dressing.

I am a male in my normal life, but an aspiring woman in my other life.  A sissy for all intents and purposes, but I would love to be pretty sissy, all dressed up nicely!  Can you help, I am a newbie to this life style?  I really enjoy the feelings of women’s clothes on my skin, but don’t think I could ever go into a store and purchase women clothes.  I did find a place online where I bought some nightgowns, a couple of bras, some panties and  even a garter belt but I what I would really love to do is to walk into my local store, buy what I need to dress as woman without feeling embarrassed about it.

If this question is familiar to you, then you are alone. For many CrossDressers, crossing that psychological line can be daunting. As a crossdresser, the easiest option is always to order stuff online, but as much as I love online shopping, buying clothes can often lead to frustration, especially since in the beginning many crossdressers don’t know what size they are, how things will fit, how they will look etc…

So a trip to a store will eventually have to be made, and all the crossdressers I know will tell you the same thing:  They wish they had done this much earlier.  Indeed, a store that sells women’s clothing wants to do one thing:  to sell women’s clothing!  To the shop assistant, size doesn’t matter, and believe it or not, gender doesn’t matter either.  So leave your inhibitions behind, you are a sissy in training, you are special in many ways and don’t let anyone tell you otherwise!  Try those beautiful women’s clothes, look at yourself in the mirror, admire the sexy crossdresser who is looking back at you, enjoy, because you, my sissy friend, are a sissy slut, and there is nothing anyone else can do about it!

Crossdresser Wigs…  We all know it, you may be the pretties sissy slut around, the crossdresser who turns people’s heads, but without a proper wig, you ain’t finished yet.  A good sissy will have a range of synthetic wigs as well as human hair wigs for the most realistic, versatile and feminine look. There are a lot of places out there specializing in wigs that are adjustable and comfortable in size to fit the male head.  And don’t forget those wig care accessories, like shampoos, hairspraiys, wig caps etc…

The best look for crossdressers.  Of course, this is a personal opinion, but I think that all crossdressers should aim for the most subtle and feminine image.  By trial and error you will experience the joy of creating a look that works for you.

Crossdressers (CD) a misunderstood group? Contrary to popular belief, men who like crossdressing are rarely gay.  In fact, it’s quite the opposite as indeed many crossdressers are for the most part heterosexual (and bisexual) with an above than average need to express their feminine side.  And no, crossdressing is not an illness.  Try to tell any scrapping Scottish man  that he is wearing a skirt (a Kilt) because of some sort of illness and he’ll probably throw you around the room with his bare hands.

Crossdressers are one branch of the transgender umbrella.  Transsexuals typically do not consider CD’s as true transgenders.  Drag Queens are usually gay men and a group unto themselves.

Crossdressing Makeup Tips – When your sister was growing up, she got all the help she needed about makeup.  In fact, as a mom, I have been amazed at how easily young girls can start to put makeup on.  It feels like it is something they were born to be.  Of course, we all know that is not the case, but girls live in an environment where following the example of other girls is the rule.  So of course, put makeup on feels natural…  Not so for boys!  For them, the first time they apply makeup can be at best described as an “interesting experience”!  It follows that apsoring crossdressers often struggle with putting on makeup.  They don’t know what to us, hot to put it on to achieve that feminine look they crave.  There are no rules.  You will learn as you go. Here are some basic instructions though:

  1. Make sure that you cleanse, tone and moisturize first as you do not want to apply makeup on a face that is not cleansed.
  2. Then apply the foundation, concealer under your eyes and around your nose.
  3. Don’t forget the whole important area many crossdressers must tackle, beard cover for your neck area and face.
  4. Next put a base of foundation with a color that matches your skin tone.
  5. Apply eye liner.  This can be difficult in the beginning but remember practice makes for the pretties crossdresser!
  6. Clean up your eye brows, fill in any holes and…
  7. Finally apply eye shadow and mascara for that mysterious look!
  8. Now to your cheeks.  A light dusting blush as you work your way down to your lips and remember, less is more here.
  9. Onto the lips now, for the glorious shimmer

Et voila, a crossdresser properly made up and dressed to look like a gorgeous girl you know you really are!

Crossdressing phone sex

3 Replies to “Crossdressing 101 – How to Become a Sissy”

  1. Stephanie

    I was named Stephane when I was born. Later on, I knew that life as a man had to be more than your typical male existence and from an early age, took an interest in the theater, which provided me with an ideal platform to put on costume, for the sake of art. It is in theater that I first played the role of a man in drags, trying to pass as a woman with clever clothing and make up and I had a wonderful director who helped grow into that role. I was so good at it that the production lasted 6 months longer than it had originally been forcasted to run. I became a cross dresser then. In order to “become” the part, I was encourage to cross dress and act as a woman outside of the theater. When the production ended, I continued to go out dressed as a woman. My wife met me when I was dressed as a woman. She didn’t mind. We’ve been married for 11 years now. I spend a great deal of my life as a cross dresser. Our sex is as any sex would be between a man and woman. I am not the type of crossdressers that you cater for on your phone lines, although my wife and I sometime do toy with the idea of turning me into a sissy. So there is my story. I thought I’d share with you. 🙂

    Reply
  2. Veronica

    Looks like you have experience in sissification Karen. My wife and I had to learn by trial and error. More errors in the beginning though. I would have been nice to have seen your post when we started. I am pleased to let you know that Mistress has done a really good job on me though, even if I say so myself!

    Reply
    • Karen Post author

      There is more to crossdressing than putting on a woman’s clothes. There is also a difference between a sissy and a cross dresser. The first one has a submission/sexual undertone, whilst the second one may not be based on either of these feelings! So I’ll call you sissy Veronica then, shall I?

      Reply

Leave a Reply

Your email address will not be published. Required fields are marked *