Top Ten Things to Think About Before Going Out (Male to Female Transgender / Crossdressing Tips)


Top Ten Things to Think About Before Going Out (Male to Female Transgender / Crossdressing Tips)

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. 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 crossdress. The second reason to never go alone is obvious… it’s a heck of a lot more fun!

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.

Arthur Fonzarelli, once said, “You can’t learn to swim if you’re standing on the dock.”

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.”

Don’t confine your prospects to bars and clubs.


Maybe you’re not a bar or club kind  a sissy girl. Maybe you’d feel totally out of place there. I understand that. Please remember that it’s not your only option.

Other cool places include restaurants, shows, plays, concerts, museums, bookstores, and gallery openings. 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.

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…
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.

Forget about sex for once.


And romance. I know the scene. 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.

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.

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.

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


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 transgender girl mode. It’s bad enough in boy mode, so why take chances.
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.

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.
People online tend to be very kind with their comments in response to your sissy photos. People in the real world are often not that kind. And wear some sensible heels.

Check the restroom policy.


Check with your friends online or with the venue itself. And remember, just because acertain 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. Or ask the management what standard policy is.

I’ll probably get criticized for this. Many transgirls 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.

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.

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 crossdressing, 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.

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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!


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