An interesting proposal

[jessica_brink]

However...its mysterious...most lesbians do not own a dress. Nor a wig. Nor makeup. Pantyhose--not likely.
High heel shoes--not a chance. Bring your own.

Does she know the truth? Will she guess the truth about your "hobby"? Are you ready for that?
Will your deep voice be a problem at the venue?
When you go to the bathroom--sit down.

She might be lesbian but is not a stereotype. She does wear dresses, makeup etc. She doesn't know the truth, no one does, and I don't see this as coming out. And yes I will mind my voice and sit down in the bathroom like a proper girl

You've been given a lot of suggestions to "just do it" and someone even said it was a "no brainer".

I suggest you engage your brain and think about this. Do you have the wig, breast forms and hip padding to pull this off, to actually pass as a woman? When you dress up and with your wig on, are you recognizable as your male self? What about your voice?

What is the likelihood of people you know seeing you? What is the likelihood of them recognizing you? What is the likelihood of word of this getting back to people you know or family members?

This is a bit like the "dressing as a woman for Halloween" thing. If you do a lousy job of presenting with a costume wig, rolled up socks for breasts and no hip padding, it will be taken as a one time joke. On the other hand, if you have a good wig, good forms, good butt padding, good makeup and carry yourself as a woman, people will easily figure out that this isn't the first time you've dressed as a woman.

Someone mentioned that you are young and at the age where experimenting may be OK. This is true up to a point. At your age and situation, this is less likely to affect your career than if you did it at age 40 with a career and family.

It's something you have to decide for yourself. Don't look at the posts on this forum as a vote, people here will not be affected by you following their advice, you will. Think about it.

To us it's not all about being able to pass as a woman. If I do, that's wonderful but that's not what the night is about. It's just for fun, at least for her.
There might be people to recognize me or not, depends. Thing is because it's just for fun, I can use that as an excuse.

This sounds like a good opportunity. I'm guessing that you and your friend have discussed LGBT issues before, and you have identified yourself as an ally. Have you ever talked about the transgender side of LGBT with her? If so, has she expressed any feelings on that subject matter? If she appears to understand how to be an transgender ally, you may want to think about coming out to her before you visit the LGBT meeting. Having someone who knows and is supportive is invaluable. If you haven't talked about it, a possible opening is: "I want to make sure that I won't offend anyone who is transgender." Then you can discuss "what you've seen online" about being a transgender ally.

Another possible step, is to ask that you give the outfit a trial run in the privacy of one of your dorm rooms, in order to make sure that you feel comfortable before committing (reassuring her that you'll still attend with her regardless, but you may be more comfortable in boy clothes). If that goes well, that could be an opportunity to come out. Regardless, please don't expect that this will turn into anything other than a friendship. Don't think that since she's lesbian, that seeing you in drag will suddenly make her attracted to you.

The last thing you may want to discuss is how you will get from one of your rooms to the meeting without being seen, especially by people who know you. If that is a big concern, maybe you can find a single occupant restroom near the meeting place, and change there? And have a story prepared in case Murphy's law rears its ugly head and you can't avoid running into someone.

If you don't do this, you will likely regret it later in life. But, you should still play it safe, and make sure you have taken sufficient precautions that you won't be outed before you are ready. Regardless of whether you decide to dress or not, I do encourage you to regularly attend the meetings with her. Remember as an ally, that you should listen more than you speak. But as you get to know people in the organization, hopefully you'll get to a point where you'll be comfortable coming out to them. And know, that these groups have strict rules about not outing someone else.

Please keep us updated.

EDIT: I just looked back and realized that I might have misread "LGBT Club." I assumed you were talking about an on-campus student club, but you are probably talking about a night club. That changes some of the advice. There's no guarantee that you won't be outed by someone you meet there. Especially if straight people sometimes attend the club.

She just knows I have no problems with LGBT people and I wanna support her. I have no intention of coming out to her as a CD, at least not at the moment.
I also don't expect to get into a relationship with her just because I'm dressed as a girl. She's a friend to me and that's all. Maybe a kiss, who knows, but no more.
Also yes, it's not an LGBT club, just a night club.

How should I act, both towards the dressing up and once as a girl?
Just be yourself, saying you took a dare. Ask laughingly, "So, how do I look?"

That's cute! I can imagine myself twirling around like a princess and asking her that question

So Jessica, you've been very quite. What are your plans? When is this going to happen?

I've been away for some time, I'm just now reading and replying, but I'm going to write an update in a sec!