Planning my first outing.... eeek!

[Fnndiap]

So, I haven´t dressed in over 2 years... (OH MY GOD!), and since it´s something my GF and I love doing (it´s kind of our private thing), we decided to check into a hotel next weekend and having a little "holiday".
I recently found a seamstress who is also a CD and had a dress done (my GF and I are into the whole little girl thing), he also does makeovers, and after he did me up a few weeks back and perfectly hid my eyebrows, I decided to book him(her) for the weekend.
Our plans are simple... have her check in on saturday while I get a makeover, then both the seamstress and I will be going out for an hour or so wo get my nails done. After my nails are done (I will of course be dressed to the nines), he (she) will drop me off at the hotel, where my GF will be waiting for me.

I have never been out "dressed" and of course I am very scared, all sorts of question come to my head. Will someone I know see me? Will I get harassed? etc...
My seamstress asked me what wordrobe I have and as many of us, I love wearing mini skirts... he immediately said no! and told me that since it´s winter, I should get some leggins, long sweater and flats... I of, of course, purchased all that he suggested. So I will definitely be posting (pics included) of my adventure.

Can anyone give me some tips about going out and being discrete? Also, has anyone been out wearing leggins? Should I buy a jean mini skirt or dress and wear that over them?

Thank you in advance for all of your advice and if possible, stories about your "first time".

XOXO
Stacy!

[Michelle (Oz)]

You are so fortunate to have a GF who encourages you. Treasure her.

You will have a fantastic time. All your fears won't be realised but it does pay to have some contingency plans, e.g. your GF walking away briefly if someone comes by that knows you both. She will be more recognisable.

One thought on your outfit for the first outing. Wear something that generally allows you to blend in with those around (by style and age). This way you will feel more comfortable and less self-conscious. Leave being out there until you have greater confidence.

[Kelley]

Sounds like fun Stacy. Let us know how it all the detail when you get back.

[Noel Chimes]

As far as clothing, dress for the weather. When you arrive at the hotel, just act like you belong there. If you don't look conspicuous no one will notice. You have to remember bellhops are suppose to greet guests as they enter. A quick reply and keep moving. You will do fine. If you have a cell, call ge as you arrive. If people think you are on the phone they are less likely to say something to you.

[Sara Jessica]

Advice? Sure. Read the article linked in this thread about wearing leggings...

www.crossdressers.com/forums/showthread.php?188897-The-great-legging-debate!

Take note of the length of tops that are worn in the "yes" photos (I don't recommend the "maybe" look, that would take some very advanced "hiding" techniques and you'll have enough to worry about for your first outing).

[I Am Paula]

If you don't wear a skirt , tunic, or long sweater, you need a perfect tuck. Practice your 'flat front' in the mirror. The male ballet dancer look is not great.-Celeste

[Beverley Sims]

Don't dress over the top and try and blend in and dress age appropriate.
Do not call attention to yourself all the time, it can get boring to others.
Also go out and have a good time without being too girly either.
When you are passing well you can up the ante and REALLY enjoy yourself.

[Fnndiap]

Thanks you all for your kind words and advice. I will def be sure to practice tucking and dress my age. I will post pics this saturday after my adventure.
Thanks again!!!!

[Alice B]

The being scared part will quickly pass. Just be your normal self with your GF and enjoy the experience. When ypu act normal, people see you as normal.