Steppin’ Out

Time to exhale. It’s been a very busy four days and now finally this evening I’m dressed up for the first time in over a week. It feels good, relaxing. I’m trying a technique to slim my eye brows using white eye liner and a small concealer brush. From a distance it works pretty well, but the illusion is ruined up close. Practice makes perfect.

The real reason for this post, though, is not my thick eyebrows, (which, to be quite honest, I could wax poetic about – negatively of course.) I write, tonight, because I feel like I have hit a wall – or a door, if you’re going to be literal.

I’ve been dressing up, with mild success, for just about two months now. I’ve purchased new things. Told new people. Experienced new feelings. I think, however, that I have hit a plateau. What else is there to do? Where is there to go? The answer, is simple – outside.

An outdoor excursion is perhaps even scarier than coming out of the crossdresser closet. When I told my girlfriend and subsequently some of my friends, I was in control. I knew who I would be talking to. I could gauge their reactions, predict what they might say, and terminate the event in case of an emergency.

Leaving the confines of my house is a completely opposite experience. The only thing in my control? Me. Every person I pass by, in my head, is a coin flip – will they react or won’t they. I’m only concerned about negative reactions – and not in the “you’ve been read” sense, but the name-calling, violent-acting sense. I can handle stares, I just don’t want to put myself in danger.

I realize, yes, I live in New York City, the liberal-mecca of the world – but that is a stereotype, like any other. There are people you want to avoid here if you’re crossdressing, and neighborhoods you probably want to stay out of.

One of the things I do have some control over is setting. Only in terms of destination however. I’ve done some research on bars in NYC that would be accepting of crossdressers, and also meet the criterion of what I’m looking for. I want a bar that is LGBT-friendly, low-key, non-dancey and would also be welcoming of a few friends, since I would like my first time out to be with a group. I don’t want to have to travel too far by subway. I only live two stops away from Manhattan, but it’s quite a bit farther if I want to go to the more LGBT-friendly west village.

I think it would be wise if I took some small steps, before great bounds. I want to take a walk around my block. I want to walk over to a friends apartment. Little victories that boost confidence towards larger ones. I need to keep telling people I’m going to go out, and keep telling myself.

In order to talk myself up, I think it would be prudent if I listed my fears, what I think will happen, and what will probably actually happen.


My Imagination

Probable Reality

Recognized by landlord or neighbors on way out of house Kicked out of apartment, tormented by neighbors It will be dark out and no one will see.
Harassed on subway Called names/assaulted by intolerant jerk No one will say anything. Who talks to people on the subway?
Bad bar experience Bar patrons are jerks because I’m the T part of LGBT. No one will care. I will complain about price of beer.
Long subway wait back at night in shady area. Train doesn’t come for hours and I’m drunk and stupid. I can take a taxi.

Alright. I feel a little bit better after writing that. I have to focus on the realistic. Focus on the positive. I am a crossdresser, with an accepting girlfriend and friends, and may be slightly passable enough to go out for a few drinks. That needs to be my mantra.

If anyone reading this has any suggestions, tips or pointers about going out let me know. Whether it’s a certain attitude to take, or places to go in NYC. I’m all ears.

On a less serious note, I’ve been marathoning Doctor Who, and would like to dress up like Amy Pond. Minus the red hair. That is all.


2 comments on “Steppin’ Out

  1. Justine says:


    Hey there! First of all – I must apologize. I got your e-mail a few days ago and my inaction towards it has been inexcusable. I would like to say it was because I’ve been busy at work, which is true, however the real reason is as follows: I’m terrified. I feel like going out is an enormous leap, and mentally I want to be ready, but I’m not quite there yet. I would like to grab a drink with you one day, but a few things need to happen first. Mainly, I need to go out on a smaller, more private excursion first (probably with my girlfriend) so that I can build some confidence. I promise I will get back to you when I am ready. (Hopefully sooner than later.)

    I would totally love to pick your brain about your ventures en femme. Your pictures make it look like a lot of fun. Right now I just have trouble imagining going out and not getting strange glares on the subway or rude comments from passerbys. One day I hope to have a confidence that rivals your own.

    So again – I’m sorry about ignoring your first message. Do not forget about me – with some time my day will come (or night…. like you said, the daylight trips come later.)


  2. “Justine…whatever you do….don’t blink!” Yes, another DW fan here.
    Now, about stepping out. I really don’t know how I got up the nerve to go out those many years ago, I just remember really enjoying it. It may have been because I knew I would be leaving the area in a short time, or just passing through, so who cares what they thought. But now, living in a small rural community, the job I used to be in and having a family, have made me more cautious. I sometimes regret not having been able to get out more when I was younger. I’m more than sure you will have a fantastic time when you do (if you have not already, I’m reading your posts chronologically). M.

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