CiCi’s Top Ten Things to Think About Before Going Out (for the first time)

“Going Out” and “Coming Out”

It probably goes without saying, but I like to start columns like this with the same disclaimer: I’m not an expert. If you want an expert opinion on any of these matters, please see a therapist or a counselor. Counseling referrals are generally available through any LGBT Center -- perhaps somewhere in the nearest large city.

But if you want the advice of a friend... that’d be me... then maybe my totally unprofessional thoughts can help out a confused and nervous newbie... that’d be you. Of course, all I can really tell you is what’s worked for me and my friends. I’ve been on the scene now since about 2001... give or take a few years here and there for career, family, and self-confidence issues.

Here are my top tips for going out for the first time. This is something that we all go through at some point. And I’m very aware that the first-timers reading this might be 22 or they might be 52. It doesn’t matter. You’ll still be anxious and unsure of yourself and full of self-doubt. And if you’re not... if you have that much self-confidence... I doubt very much you’d be reading a self-help column like this one!

Oh, and one last thing. Congratulations! You have no idea how much I respect you for even thinking of taking this step. I don’t think we’ll ever know the exact percentages, but I’m pretty sure that most cross dressers never go out (or come out). You’re a rare breed. Never forget that. Never forget to give yourself props for daring to live the life you dream of.

Okay, here are some tips...

1. Don’t go alone!

That’s a really bad idea. Find a friend (preferably an experienced friend) to tag along with. The first reason for this is simple safety. I think the world is, in general, a much safer place for transpeople today. Of course your country/state/town/neighborhood might not be as progressive as sunny Southern California where I live. Still, no matter where you live, just as I’d advise any woman or young person to never go out alone, I’m telling you the same thing. There’s safety in numbers. The second reason to never go alone is obvious... it’s a heck of a lot more fun! You don’t know it now, but you’re about to meet some of the most amazing people you’ve ever met in your life. Try and get one of them to take you along.

2. Do it soon. Seriously.

Go now. Are the bars closed yet? Go tonight! Why am I adding such ludicrous urgency? Because cd/tv girls are notorious for finding reasons NOT to go out. We are the ultimate procrastinators. We want to wait until we can afford those cool shoes, fit into that hot dress, perfect our make-up technique, feminize our voices, and learn the newest dance craze.

To which I say, Great! We’ll see you out at the clubs in 2027. If ever. My point is that there is no good time to go out for the first time. And while I hate to burst your bubble, you will never achieve any of the goals above. Your income level, your weight and fitness, and your make-up skills are what they are. And they’ll probably be pretty much the same two years from now, five years from now, and ten years from now. That’s the hard, cold reality. Sure, you can fine tune as you go along. You can hit the gym, you can follow some fad diet... but most people only last a few months. And then you’re right back where you started. You can also certainly improve your dancing, your make up, and your feminine gestures through practice and experimentation. But the best way to do that is to go out and observe how others do the very same things. And then get out on the dance floor and do them yourself.

I’ve met or conversed with literally hundreds of transgirls over the years, and when it comes to the topic of “first time out,” every girl -- bar none -- has told me the same thing, “I wish I did this years ago.” Yet, I’ve never met one who said, “I wish I’d waited eight more months.”

As one of my life mentors, Arthur Fonzarelli, once said, “You can’t learn to swim if you’re standing on the dock.”

Correctamundo, Fonz!

3. Don’t confine your prospects to bars and clubs.

Maybe you’re not a bar or club kinda girl. Maybe you’d feel totally out of place there. I understand that. I like clubs, but when I started going out as CiCi (in my 40’s), I hadn’t been to a night club in nearly 20 years. I’d hit the clubs as young adult, but then I moved on to more “mature” pursuits. Like starting a career and raising a family. So the club scene took some adjusting. Please remember that it’s not your only option.

Other cool places include restaurants, shows, plays, concerts, museums, bookstores, and gallery openings. As you can see from my list, I like the arts. I also happen to think that the artsy crowd is a little more accepting of people who are different. Your results may vary. (And BTW... I don’t go there as CiCi a lot, but everyone at my local Stater Bros. and Trader Joe’s have always been very kind to me.)

I’ve also heard of many girls whose first time out consisted of nothing more than driving around town, or walking their dog at 3 am, or hitting the late night drive through fast food joint. That doesn’t really count as “going out” to me. But I understand its purpose. It’s a way of getting your feet wet without diving in all at once. Cool! At least you’re taking your baby steps. And a little progress is better than no progress at all.

4. Go for a professional makeover.

Make up artists are so talented! And there’s probably one somewhere nearby. They’ll make you look awesome and, while you sit there in their chair, you’ll learn tons about make-up products and techniques and styles. It’s a pretty amazing experience... and well worth the expense. Many make up artists will also take photos of you, and some will even “escort” you out for a night on the town. You couldn’t be in better hands!

Another side benefit? The make up artists are very tapped into the transgirl social scene. They can tell you about the hot clubs, fun events, and little known alternative outing opportunities. They are very good people to get to know.

5. Forget about sex for once.

And romance. I know the scene. I know how this works. You go online. You show a few pix. And then you spend the next couple of months (or the next couple of years) engaged in highly erotic sex chat on social media. Or at the very least some high octane flirting. Maybe a few of us have skipped this step, but for most of us... been there, done that.

And why not!? This is a whole new persona for most of us. A whole new chance to present a whole new face to the world. What kind of deviant, repressed human being would we be if we didn’t want to take our new persona out for a test drive? Especially when the internet provides such a safe, anonymous means of exploration and experimentation.

Still... no matter how real it feels, cyber sex is not real. Cyber romance is not real. Cyber stuff might lead to real stuff later on. But things are about to get very real for you right now. When you start going out to bars, you’re no longer in Second Life. So if you’ve been presenting yourself as the world’s biggest CD slut around, believe me, the people in the bar are going to be expecting that from you. Are you prepared for that kind of welcome when you walk in the door of your local pub for the first time? Perhaps you are.

But for most of us, I’d advise taking it slow. Just going out in public for the first time is ordeal enough. My first few times out, I was too nervous to talk to anyone. I sat at a table alone all night. If I nodded or said hi to someone who wasn’t my waitress, I considered that a victory.

I remember being too terrified... paralyzed really... to get up from my table and walk to the bar to refresh my drink. And my table was literally three steps from the bar! So prepare for a night of debauchery if you like, but don’t be surprised if you find yourself dealing more with social paralysis than unbridled sex.

And, in case you haven’t been out in the dating scene in a while, please remember, “No means no.” You should never do anything you don’t feel ready for... and you should never pressure anyone else either.

6. Check your car. Check your route. Check your destination.

I know, I know. It sounds like I’m talking to my teenaged kid. But I kinda am. Like a teenager, you’re going to be out at night in strange surroundings feeling totally out of place and awkward. So prepare for that. If you have a GPS device, set it well in advance. I like to go to a gas station earlier in the day... when I’m still in boy mode... and check the tires and the oil and fill up the tank. The point is, you don’t want to have car trouble when you’re in girl mode. It’s bad enough in boy mode, so why take chances.

To be honest, several of my friends have had car trouble when in girl mode, and none of them have ever had any problems with the cops or tow truck drivers. Everyone has been very kind and helpful. But as always, your results may vary.

I shouldn’t even have to mention it, but don’t drive under the influence. There are strict penalties and, even worse, you might hurt someone. Also, don’t forget, you may be driving for the first time with high heels or big boobs or a giant wig. Steering and braking may feel very different. And something as small as your lovely fake eyelashes could hamper your vision. So drive safely. Give yourself plenty of time to get to where you’re going.

7. Dress appropriately.

I don’t care what kind of style you want to rock on your first night out... but be sensible. You might be shocked to learn this, but what looks good in your bedroom or on cam with your pervy internet friends might not work in public or in a particular bar or restaurant.

Just remember, it’s relatively easy to take a few photos in good light from a flattering angle, photoshop them, post them on the internet, and get a good reaction. But life ain’t like that. There is no good lighting in a bar. There are no flattering angles in public. People see you from every angle -- whether you like it or not. And you don’t get to photoshop or enhance a thing. Sure, you can hold your breath when you take a photo, but try holding in your tummy for 6 hours straight. It can’t be done. So think about that before you decide that you don’t need outerwear over your sexy lingerie. People online tend to be very kind with their comments in response to your photos. People in the real world are often not that kind.

Also, if you haven’t walked a lot in high heels, prepare for a soreness like you’ve never experienced before. (Perhaps the six inch stilettos aren’t such a good choice for your first night out.) You’d think that walking around your house for a few years in heels would help. But believe me, it does little to prepare you for uneven pavement, cracked sidewalks, and slippery bar floors. I’ve gone down more than a few times crossing the street! Almost ruined a pricey latex catsuit that way. So watch your step. And wear some sensible heels.

8. Check the restroom policy.

Check with your friends online or with the venue itself. And remember, just because a certain law says that you can do something, that doesn’t mean that that’s the way things work out in the real world. If you’re in a gay- or trans-friendly club or community, chances are you’ll be fine using the ladies room. But in mainstream venues, you may not feel welcome in the ladies room. Use your best judgement. 

I’ll probably get criticized for this. Many trans girls believe they should always use the ladies room and that it’s their right to do so. I am honestly not sure what the actual restroom laws are -- or if they vary from community to community. But here’s my bottom line. I’d never advise anyone to walk into a bad situation in a private space away from the public eyes... and that includes restrooms. It’s just not worth it.

9. Bring back-up.

I always pack a duffel bag of boy clothes just in case. Just in case of car trouble. Or a torn dress. Or if maybe I just have a bad night and want to tear off all my femme clothes and be a boy for the ride home. (It happens.) I usually just bring my gym bag with some sneakers and sweats, along with some make up remover and a few towels and handiwipes.

Important note: I’ve never ever used them! I’ve always driven home en femme. But I bring back-up every time. I guess I just like to be prepared.

10. Have fun!

You’d think that would go with out saying, but sometimes it’s hard to enjoy yourself on your first night out. So many things can go wrong. So many things will go wrong. Expect them. Be ready for them. And roll with them when they happen. If you brake a heel, dance in bare feet. If you miss your ride, take a cab. If the cover is twice what you expected, pay it! It’s one night. It’s your first night. Breathe in every moment of it. Your life will never be the same again.

Like I said at the beginning, only a small percentage of crossdressers ever go out. But I’d bet that when they do, a very large percentage keep going out again and again. It’s very addicting. It’s very liberating. And it can be more fun than you ever thought you’d have on Earth.

One more thing: Never let the loud-mouthed drunk in the corner get you down. Remember, his best years are far behind him. While the best years of your life are just getting started!


  • Cassandra Jade

    Cici you look amazing! I'm in the early stages of my cross dressing. So far my make-up artistry is dreadful, however I got potential to conquer it. I can't pass yet, but I look & feel beautiful. I've been wanting to feel myself for years. I can't wait to get out there, especially the mall. After that, boystown honey! EnFemme helped me get there. Hugs & Kisses – Cassandra Jade

  • Angela

    CiCi thank you for the wonderful tips! I want to go out in the worst way!
    I know, I know, just DO IT. I am working on the courage but will have to go alone as I haven't told anyone (my wife caught me though) and I don't know any sisters that live close to me. Maybe the next time I am alone for a while I will take the leap. CiCi please write more articles as I love what you write. By the way, you are GORGEOUS!!!
    Hugs and kisses, Angela

  • Rain

    Hi CiCi. I've always like reading your articles. And to quote you "I like the arts. I also happen to think that the artsy crowd is a little more accepting of people who are different." In my own experiences, people who are in the arts are fairly accepting of us. When I was in college and working on my associate's in fine arts, I once wore a pair of leggings and high heel boots. It was Halloween and I said it was part of my costume. When they asked why I wasn't in complete costume, I lied and said do you really want to see me wearing a corset. Actually it was exactly what I wanted to wear and was not my costume. I even wore them to work that night when worked the over night shift at a gas station. Got a lot of good comments. Usually I work alone, but Halloween that year fell on one of our stocking days so I had coworker. She loved it. She loved hearing the sound of my heels on the floor as I walked around and stocked the shelves.

  • Jamie Rhodes

    CICi, great tips for everyone. As I read your tips I reflected back and every tip is spot on.

    Friends, I know this lady, she is not only gorgeous but she is a good person as well. The tips she suggests for newbies are valid tips for any girls whether you are a newbie or experienced veteran. I highly recommend that everyone takes advantage of this advice.


  • Julie

    CiCi – These tips are wonderful. I'm about to go out for my first time tonight and I will be following your suggestions. Thanks.

Leave a comment

Please note, comments must be approved before they are published