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paola_gemi
01-31-2015, 12:12 PM
One day when I started to have the urges of dressing up, I decided to carefully plan my first time out.
It took probable a few months to get everything ready. For one thing I had yo coordinate it when my wife would be away; So I started to buy a few things, since I had nothing then.
Little y little I got all the essentials like make up, some clothes, high heels, a wig, etc. 10 years ago the internet was not as full of information as it is today, but you could still find a lot of knowledge, tricks and tips.
I wasn't worried about make up because I have three sixtes so I always knew how to do the basics, tucking was a bit of a challenge, but I managed to learn a few tricks and practice a few times before my big plan.
I learned that it really takes a lot to do the right tucking, I only got two techniques that I felt confortable with and stuck to it.

The anticipation of everything was always a thrill, weeks before I went out, I tried to master my techniques because I really wanted to pass as much as possible.
I tried to figure out what the first step would be, and shaving my body was the first, then doing my manicure and pedicure, fro then on it was mostly a piece of cake. The tucking was in the bag so I did it before make up, to make sure everything was in place while I move and would be conformable as possible.
Make up and clothes followed then the wig, but for some reason the last part has always been to slip into my heels, for me that is what sealed the deal to complete my transformation.

When i put the heels on, I was already prepared to go out, I had already all my items prepared. I had my purse with the touch up make up items, cash, an spare key to my car, and an id.
In a gym bag, I had more emergence make up stuff, some panties or anything else that I would think would be useful such as nail polish remover, wet towels, etc.
Also I had my set of guys clothes, shoes etc.

Once I was ready, I grab all my stuff and took a big breath before crossing the door, of course after picking thru the window to see if any neighbors were out.
I felt a little bit of a rush, walking across the parking lot going to my car, and it was the greatest feeling when my feet touched the ground with my high heels, clicking all the way for about 50 feet from my door.
Little breeze refreshing my legs going up to my mini skirt and coolness clashing into my thong, wow not having anything hanging from your body and your butt almost naked felt great.

I got in my car and there was another feeling, driving with the heels on.
I put some relaxing music and drove my self about 25 minutes to NYC, once in the city, was another story, every red light I was a little concern, I felt that people look at me, but I wasn't sure because I thought I look good or because the masculine side would sneak out of my face.
Anyway, I knew where I was going and there was no nervousness, more a sense of excitement and accomplishment.
When I arrived to the night club I was going I saw a line of people standing there. It was I gay club, I though I would be safer from judgement there. When I got to the door, Knew I passed, or at least I though I did, because I had to show my ID to the doorman, as he compared almost in disbelief my picture and ran his eyes up and down and said "VERY CUTE" as he handed back my id.

I was at the club for may be an hour, I had only water because I didn't want to expose my self to any trouble.
Then I drove back to my vary satisfied and happy of what I had done. I broke the ice, and it really was a milestone for me.

After that time I did it again the next day and went to a private party, and from then on every time was much easier.

But nothing like the first time out, it was a mix of nervous, excitement, and triumph, but the most important thing was how feminine I felt and how goo felt being in my skin.


It was a real thrill, please share your stories.


Hugs,


Paola.:daydreaming:

Isabella Ross
01-31-2015, 12:45 PM
Nice story, Paola. I hope I can offer up a similar tale sometime soon...

Karolyn
01-31-2015, 01:26 PM
The first time feels incredible! The longer you prepare for that event, the more you build fears to be honest, but excitement at the same time. The doorman saying "very cute" probably gave you a huge confidence boost.

You are really going to enjoy the next outings too, minus the fear, and it will become so good you will regret to not have done it earlier. You should do clothes shopping en femme and go to the woman section and dressing rooms (if you think you are passable), and enjoy! It has been my best experience so far.

Persephone
01-31-2015, 01:48 PM
What a great post, Paola! You really captured the feelings and flavor of a first time out.

My own was so long ago that it is shrouded in the mists of time. My first outings were of the scared little girl type. I was doing some work out of town and my spouse and I would stay overnight in our motorhome. It was off-season and we were the only campers in the park. I would get dressed and she would take the com, equipped with a two-way radio she would scan the surroundings from the motorhome as I walked around the park for a while.

Then came Halloween and I dressed for my first time out in public. Went by a friend's house, totally forgetting that his elderly Mom was visiting him! He was a bit speechless, terrified that his Mom was seeing me. She looked me over, smiled, and said, "Nice legs!"

Here we are, about 40 years later, and I am rather out-and-about. Take this weekend so far for example. I was out for dinner with people Thursday night, meeting a business associate's wife and mother-in-law for the first time. Friday, errands all day and religious services in the evening. All, of course, en femme.

Life is good!

Hugs,
Persephone.

Eryn
01-31-2015, 02:01 PM
Paola, thanks for sharing your story! Your success will point the way for others.

I had two "firsts." The first time I went out of my house was to a CD dinner at a LGBT-friendly restaurant. I had to drive 60 miles each way, but the driving and dinner were relatively cloistered even though the restaurant was public. I had a great time!

The Second "first" was an overnight trip to Solvang with Persephone, her spouse, and Mimi. Solvang is a Danish-themed tourist town. That one was really being out, all 6'2" of me walking with hordes of tourists, eating at mainstream restaurants, shopping, and going to live theater. I was nervous and it is a bit of a blur, but I remember that I was complimented twice by GGs on the dress I was wearing, once by a waitress and once by the usher at the theater. It was this outing that I think of as my first real experience out in the world.

paola_gemi
02-01-2015, 03:10 PM
Thank you all for your comments: Isabella: I am sure that you will not be able to wait to tell us when you have a outing story, It is very exciting when you live it in flesh and bone.

Karolyn: Indeed the doorman sealed the assurance that what I had done that knight so far was a real mission accomplished, I am not sure if people who work in gay clubs are all gay, I don't know if that would make a difference in people's perception, but I realized that the first thing he saw was a woman, only until he saw mi id perhaps his compliment came from his surprise.
And yes I have going shopping in femme, well kind of... The first time I did it was one of the first times when I went during the day, and I went to a huge shoe store in NYC, and the biggest thrill was when I parked my car and walked over to the corner. Waiting for the longest red light to change while a group of about 6 police officers were hanging out on the other side, and a couple of them were looking at me. My thought were that they were looking at a hot girl, or... they were wondering is she?..
As I passed them by, I felt their eyes piercing thru my back, but I proudly walked bay hoping that I passed. Then I enter the doe store and tried some shoes comfortably.
The second time was las summer also in NYC and I went to a clothing store and tried some stuff on, it was great.

Thank you Eryn, for sharing too, I sure many more times could feel like the first and that is awesome.

Persephone: I guess I did really capture the feelings and flavors of the first time, I think that when you really love to do something it tends to stick for ever.
And your comment makes me realized that indeed, I was missing that point, and re assures me what I am and where I should continue to go with my feelings, because every time I remember any outing, it is like it was yesterday, and I enjoy the thoughts every time and that is why I love to share them with people whom really understand it.


Thank you all.


Hugs,


Paola.