Baby Steps in Sky High Heels: A Crossdresser's Guide to the Tgirl Lifestyle

By CiCi

"Baby Steps in Sky High Heels" is a compilation of blogs written by CiCi for the SuddenlyFem(TM) website. CiCi has been writing monthly blogs about the transgender/crossdresser lifestyle since 2007.

• Language: English
• Publisher: BookBaby
• Release date: Aug 20, 2013
• ISBN: 9781483508030

Book preview

CiCi

Baby Steps in Sky High Heels

Monday, December 10, 2007

A few months ago, a nice gentleman from this website contacted me and asked me if I'd be willing to write a monthly column for the site. Something with a bit of a personal perspective. Something that might add to the Suddenly Fem experience. Now, I like to write. And I love attention (ask any of my friends). So without really thinking it over, I said, Yes.

Silly me. I had no idea what I was getting myself into. I've been dressing for about seven years now - give or take a few years due to the time when I freaked out, swore off dressing, and tossed all my clothes in the trash. But for the most part, I think I've been making some progress in my feminization process. I'm getting out in the world. I'm getting more comfortable in my own skin. So by this point, I should know a little bit about girlworld. About dressing. About style. About important political issues facing the transgender community.

Um. Well. Actually. It seems. I don't.

Don't worry, said the gentleman who hired me. Just throw in some tips on how to do makeup. Or how to lace up a corset. Things like that.

That's when I really freaked. I have no idea how to lace a corset. And I'm still struggling with my makeup. I'm not the kind of person who can answer questions like that. I'm the kind of person who goes online to search for answers to questions like that! (To be honest, my best solution for both of those questions would be, Have a friend do it!) So I was forced to face the awful truth. I have no business writing a column like this. I'm just not an expert.

Then it hit me. That's when I accidentally stumbled upon the overriding theme for this column. I won't present myself as an expert. Instead, I'll present myself as a girl who's a lot like the typical reader. A lot like you.

Does this sound familiar? Am I still straight? Am I bi? If I like other t-girls, am I a lesbian? What if my family finds out? What if my girlfriend finds out? Oh my god, what if my mother finds out? Do I have to leave the closet? Do I have to tell my wife? Do I have to shave my legs? Can I still wear shorts in the summer? Is it autumn yet? Will everyone at work notice that I pluck my eyebrows? Is this too much makeup? Or is not enough? Will the girls at the MAC counter really be nice to me? Will the salesgirls at the mall realize that my wife doesn't have size 12 feet? And what if I get pulled over by the cops? And finally, how can I focus when I have all these questions zipping around my brain all at the same time – while I'm on deadline at work, my wife is on the phone, and I still have to get the kids to soccer practice by 6 p.m.?

It's not an easy life, is it? But we're doing it. If you're reading this column, I'm going to assume that you're a dresser of some sort. That you enjoy wearing ladies clothes. And you're hoping to get better at it. Well, that's exactly what I'm doing.

For years when I was online, people would ask me how I was doing. Had I gone out yet? Had I dated yet? Had I had sex as a woman yet? (People online can get pretty personal.) Anyway, I gave them all the same answer. I told them I was progressing, but that I was going slowly. I was taking baby steps. Baby steps in sky-high heels.

And I'm still doing it. And I'll bet you are too. So where are you in the process? Are you dressing head-to-toe? Or do you just do panties and nylons? Have you bought your first wig yet? Have you bought your first pair of heels? How big is your makeup collection? Or maybe you've started going out. Maybe you've shared your secret with friends or loved ones. Maybe you're even thinking about going full-time. Or transitioning through hormones or surgery.

The point is. We're all at different levels here. We all have different goals. But we're all wondering the same exact thing: Where does this all lead? Where does this all end? And that, my sisters, is a question I just can't answer for you. And I couldn't answer it even if I was the top expert in the field. But I can give you my opinion.

This never ends. There is no finish line. You may never come out of the closet. You may never be anything more than a cyber girl. On the other hand, maybe you'll end up having SRS surgery and becoming a brand new woman with a brand new driver's license to prove it. It's all waiting for you. You just have to decide what it is. There are so many options available to you now. So many ways to express your T.

And that's what I'm going to write about. The problems and the possibilities. The fears and the fantasies. The hopes and the hopelessness. Just don't ever think of me as an expert. Because I'm not. Nope. I'm right here next to you. Taking my baby steps. In a brand new pair of really killer sky-high heels.

Take care out there.

Be safe. Be smart. Be sexy.

xoxo,

CiCi

Dazzle Me

Monday, December 10, 2007

Or better yet, dazzle yourself! Come on, girls. We all know how hard this is. Looking femme. Looking good. (Looking good and femme.) But no matter where we are in our tranny transformation - from newbies, to closet queens, to professional showgirls - we all want to look our best. We all want to turn a few heads. Even if all you're ever going to do is show a few pix on the Internet, admit it, you still want to look a few clicks beyond fab.

And that's where the professional makeover comes in. I don't care where you live. I don't care how broke you are. I want you to get on the phone and make an appointment right now! It's an experience that will literally change your life. Because, unless you happen to be a professional makeup artist, there's so much to learn! The tips. The techniques. The new cosmetic products you didn't even know existed.

I know it's hard if you're closeted. I know it's hard to meet a total stranger and reveal your most closely guarded secret. But I've never had a bad experience with a professional makeup person or a photographer. I've never been treated with anything less than the utmost respect. And what a day you'll have!

You'll feel like a queen. (I know. I know. We're all queens! But with a makeover, for one day, you'll actually be treated like one!) You'll be doted on, pampered, and generally made to feel special. You'll get to try on a variety of clothes and wigs and shoes. (Yum. Shoes.) And you'll leave your session with a set of killer pix.

It usually all starts with a phone call. And for lots of girls this is no small thing. To pick up the phone and actually set an appointment. Because as soon as you make that call, it's official. You're a crossdresser. You're not just playing around any more, you're serious enough about your dressing to want to look your best. And you're serious enough to now present yourself to the world this way. (Okay, not to the world exactly. You're going to present yourself to just one makeup artist. But let me tell you, it will feel like you're telling the whole world.) So don't be surprised if you have to pick up the phone a few times before you get up the nerve. Or hang up on a few answering machine messages before you actually succeed in setting the appointment. It's all part of the process.

When you do get the girl on the line (they're almost always girls - or other tgirls), you'll be immediately surprised how relaxed and nonchalant she is about your dressing. After all, this is a big step for you. But it's just another day at the office for her. If she's good, and most of them are, she'll put you at ease right away and she'll let you know what to expect during your makeover session and photo shoot.

Some dressers like to bring photos of actresses or models they'd like to look like. Some bring photos of other tgirls they admire. For me, I wouldn't bring a thing. You already know how you want to look. But for this day, let the expert take the lead. Let her look you over, study your face, and try to achieve the look that's right for you. Chances are you'll look nothing like what you originally envisioned. But you'll still look amazing.

Once she's gotten the look down, it's time to pose. And let me tell you, it's not easy. When I started dressing I took all my own pix. I'd set up the camera, hit the automatic shutter, and then run like hell to get in position and pose. The whole process was downright comical. Fortunately there was never anyone else in the room. And no one ever saw the worst pix.

But posing for someone else is a whole different story. Even if she's made you feel comfortable by this point, you're going to feel a whole other level of awkwardness when it's time to pose. Because it's a totally unnatural act. You'll put your hands here, your legs there, your butt over there. Now try to look sexy!

It's uncomfortable. It's awkward. It's nerve-wracking. And you'll be so sorry when it's over. You'll never want it to end.

So go for the makeover. Go for the fashion shoot. I promise you. When you see those pix, you'll hold your head a little higher. You'll walk a little prouder. Even if you never show your photos to anyone else, you'll look at them again and again. You'll treasure them. Because you'll know, deep down inside, that that girl in the photo - the pretty girl in the hot outfit - that's the girl you were always meant to be.

Take care out there.

Be safe. Be smart. Be sexy.

xoxo,

CiCi

The Cyber Closet

Monday, December 10, 2007

I don't have any statistics. But I think we can safely say that most dressers are somewhat closeted. If not totally closeted. The truth is, even some of my most out friends still haven't told their closest friends or family members about their T-lives. And personally, I don't think there's anything wrong with that. We're all on our own paths to feminization. We all have our own personal boundaries and comfort levels. Some of us will go further than others. Some will go all the way to SRS. But odds are that most of us will stay right here where we feel safe - right here in the closet.

And hey, the closet isn't so bad. (There are some pretty cool shoes in here.) And just think how much better we have it than our sisters in the past. Just a few years ago, before the Internet became widely used, most crossdressers suffered alone. They had no one to confide in. No one to swap feminization tips with. No one to share the emotional highs and lows of being a T. The closet was a pretty lonely place back then. And very dark.

Then the Internet came along and it was like someone switched on a big bright light in the closet. Emboldened by anonymity, crossdressers, trannies, and femme freaks of every kind flocked to the chat sites. They chatted about clothes and makeup and dating and style. They compared notes on everything from politics to movies to sports. They found they could order clothes and accessories online. (And then they could chat about their new outfits.) They found they could secretly explore their lusts and fetishes. (And then they could chat about their dates.) But most importantly, they found that they weren't alone!

I remember when I first logged on as a girl. I think it was in the year 2000. I sat quietly in chat rooms and barely spoke. I spent hours studying profiles and photos - marveling at the other girls. The clothes. The makeup. The shoes! Back then, I was amazed that some girls showed their faces. I tried at first, but I just couldn't bring myself to do it.

I was one of the (many) girls who wouldn't show her face. And I wasn't alone. If there's one thing we crossdressers are really good at, it's taking photos that don't show our faces. We've got that down to an art. Photos of bodies with no heads. Photos of nice long legs and sexy high heels. Photos of cute butts. Photos of ugly butts. We'll show anything to avoid showing our faces.

Now part of that was for reasons of privacy. But for me, part of that was also because I sucked at doing makeup. Even when my makeup looked good in the mirror, some how, it didn't translate to the camera. So most of my early pix have my hair falling down over my face. Kind of sexy. Kind of mysterious. But mostly there to hide another botched makeup job. (BTW… the second thing we crossdressers are really good at, after hiding our faces, is using Photoshop - but that's a topic for another day.)

Fortunately, there were other girls out there who were not so shy. They showed their faces. The showed their bodies. Some even listed their hometowns!

Were these chicks crazy?! Thankfully, yes they were. A little crazy and a little bold. And maybe just a little tired of going it alone. I've kept in touch with some of the first girls I met online. And every once in a while, when I'm feeling sentimental, I shoot them an email and thank them (yet again) for being a friend to me when I was a newbie. For liking me when I felt unlikable. For accepting me when I had assumed that my behavior and desires were totally unacceptable.

Some people say you can't make real friends on the Internet. But that's okay by me, because the friends I've made online are absolutely unreal. In all the best ways. They're kind and considerate. They're helpful. They applauded my new pix… even when my new pix weren't that good. They invited me out. Although until recently, I never accepted their invitations. In short, they treated me with respect. And unfortunately, that's not something most of us tgirls are going to find a lot of out in the real world. (Heck, I even met the person who hired me to write this column online!)

Maybe I'll never be totally out. Maybe I'll never tell my co-workers and relatives about my girlie side. And maybe I'll never truly leave the closet. But at least now I'll never be alone. Because, thanks to the Internet, my once lonely closet now has a lounge. And the lounge has seating for millions. Best of all. So does yours.

Take care out there.

Be safe. Be smart. Be sexy.

xoxo,

CiCi

Hey Tgirl! What's Your T Stand For?

Monday, December 10, 2007

Here's a little insider information. In my boy life, I'm a writer. I've actually sold a few screenplays. And now, as I've started going out more and expressing my T-self a little more openly, I've decided to write a T-themed screenplay. I won't go into any details here, but there is one scene that I think is kind of cute. So I thought I would share it with you.

Now, for those of you who don't know much about Hollywood, don't go holding your breath waiting for this film to come to a theater near you. I have to finish writing it. I have to try to sell it. Someone with money has to like it. And someone with even more money has to decide to produce it. Let's face it, straight-themed scripts are a long shot at best. So the chances of a T-themed script getting made are pretty slim. (Ladies, we should all be that slim.) But I'm going to give it my best shot. I just keep thinking that if it ever does get made, the premiere party and the red carpet walk will be way beyond fab!

Anyway, right at the beginning of the script one cute little T-Kitten says to another, Hey tgirl, what's your T stand for? It's played off as a joke in the script. But I think it's an interesting question. It makes the girl in the script stop and think, and it just might make you stop and think as well. I mean, think about it, what does your T stand for?

Are you still shy about your dressing (Timid) or are you bold and confident (Tantalizing)? Is your look Tacky or Trashy or Tasteful? Are you feeling Terrific? Tremendous? Are you a Tease? A Tart? A little Ticklish. A little Tipsy? And don't sell yourself short if you identify best with words like Truthful or Trustworthy. There's way too little of that out there in girlworld.

It's a silly question, but it really gets to the heart of the issue for most of us. I mean, why in the world are we doing this? I remember how it was when I first started. There was a lot of sneaking around. There was a lot of frustration with the process. (That really never goes away. I'm still lousy at putting on fake eyelashes.) There was the fear and dread of being outed or caught. So there were secrets to keep. There were clothes that didn't fit right. Makeup that looked down right awful. And nights on the town where frankly I wished I'd just stayed home and watched a football game! (Yes. The boy in me is still strong.)

But here I am. Still dressing up. Still going out. And still wondering where the heck this all is supposed to lead. To be honest, I'm still not even sure where I want it to lead.