Not as expected

Hi girls. This will be a long one, so pass if you like.
I've recently started going out as Val, having attended a Rori's Tea Party in Chicago, and my first shopping visit to a local Kohls. Last weekend I decided to attend a social event run by Chi Chapter of Chicago, which I've recently joined. This is held at a hotel bar, which is fairly well populated. I made reservations at the hotel so I could get ready without a lot of fuss.
I still do not have my feet under me as far as going out, but its quickly improving. A fantasy has been to go to restaurant, either by myself or with my wife. I envision myself relaxed, dressed appropriately, but in a dress, and attracting some attention, but not much.
As I got ready for this Chicago social, it occurred to me to suggest a dinner to the organizer, and while she had to decline, she connected me with another CD who has also wished for a sit-down dinner, instead of bar food. I'll call her Janet, because I don't want to use her actual femme name here. We texted, shared photos, she reassured me I looked good enough to go out, and we set up time and place to meet.
Things started to go off the rails as soon as I got to the hotel registration desk. My reservation was for the wrong date, and getting that sorted out took a long time. By the time I was in the room, I only had two hours left before Janet would pick me up. I'm still not skilled at makeup, so it seems to take forever to get to where I can barely accept it. Even though I've had some laser treatments, I still have beard on the upper lip, and I must've painted a pound of red lipstick and concealer on it, and it STILL showed through! Yes, I've successfully put on the magnetic lashes at home a couple times, but when the time came now, I failed miserably and could not make them reliably stay in place. As the clock ticked down, I had to dress, and gave up on putting my carefully painted press on nails, and almost forgot my jewelry. Wig on, quick brushing, some wig spray, pick up purse and out the door. I'm sure this panic to get ready, has only happened to me.
So, yes, out the door. Out in a hotel third floor corridor, as Valerie, and I'm going to the elevator. I don't have time to hesitate, I'm late for Janet. No time to think about - I'm in a small elevator with a man I don't know. No time to think about walking across a crowded lobby, but remember posture and manage the purse. Holy cow, I'm at her car and I climb in, hopefully as a lady would.
Janet was awesome, a couple years my junior, but she's been out and about a lot. She again reassured me, and off we went to the restaurant, which was close by. As we drove by, I realized it was in a cluster of nice restaurants which are tied to a shopping mall. It was absolute chaos outside, with the restaurant entries packed with people waiting. Janet had made reservations, so we step out of the car (I'm in broad daylight as Val in a crowded shopping mall parking lot), walk to the restaurant, chatting as we go, and we are seated! Its as if nothing is unusual. Now, I do not even come close to passing. But the wait staff, and more interestingly, the rest of the people, paid no attention to us, at all. I know this is written in many other threads, but really, nothing at all. Janet thinks of these outings as sort of an outreach opportunity to the community, so she made sure we were not in some dark corner. We were out there!
I was beginning to come down from the panic of getting ready, and tried to process where I was, how I was, and the events around me. It was far from the fantasy I had of a demure woman at a restaurant; I was pretty wound up and at times I felt like I was stumbling talking to Janet. She shared a lot of her experiences, and constantly was trying to make me laugh, which helped a lot.
Well, dinner over, and up we stand, walk out to the car, passing a lot of people, and again, it was all just pleasant. Off to the hotel, where we walk to the bar. There are several girls there already, and we had to keep adding tables through the night and by the end we were around twenty girls strong. The bar had the usual clientele, but no adverse interactions. I had some great conversations with girls who are all over the spectrum, from fully transitioned to CD's like me. Everyone was willing to share their experiences and steps they had taken on their journeys, and I felt like I was among my tribe. Along the way, I had to refresh my lipstick (some good-natured coaching), so more lobby and elevator time with people I don't know. I passed a young man sitting on a bench outside the elevator, and as I approached, he looked up at me and then right back to his cell phone. I think I got by him!
The bar closes early, so we all said our goodbyes, and I went back up to the room to change for the long drive home. None of it went as I expected. No harassment, and great company with Janet and the girls; but also I had not achieved the happy relaxed feeling I imagined in my fantasy. I think that means I need more practice! I've attached a pics of me in the room at the end of the night, and just outside the bar. I had the blue shrug on most of the evening.

Not everything goes to plan in life Val . Sounds like you had a wonderful time. It helped having the support and companionship of Janet.Would love to do what you did. Give yourself credit for going through with it. Also your photos look great. Love the outfit.Thanks for sharing your experience. I enjoyed reading it.

Thank you for sharing both the photos, (you look lovely) and the detailed story. You painted a wonderful portrait of the evening and the exciting as well as natural pieces that I am sure will give you added confidence and serve as a road map for many of us. I look forward to your future adventures.

Tiffany

I think you look like any other lady out for the evening. I'm glad you had a nice time. I just wish I looked as nice as you.:hugs:

Rarely do things go as you might expect, but it sounds like a wonderful evening! That happy, relaxed feeling will probably come with time and more experience. I think you will see in time how memorable this experience was, in its own way. I hope my first outside experiences go as well. And, I must say, you look great!

Congratulations Valerie
You look very confident & natural.

Thanks for sharing the experience.
I hope to do something similar in future & your story
& those of others give me confidence it can be done .

Wow! Congratulations Valerie!
You never forget your first! :daydreaming:

Reminds me very much of my first time really going out except mine was at night. Like you, there wasn’t a lot that went right as far as me getting ready but once I was with friends, all of whom I’d interacted with here, my nerves calmed down significantly.

Good for you on getting out. Keep practicing as you can and you’ll feel better about your makeup skills, gathering everything together that you need and have that relaxed time you’re aiming for. Muah!

Wren

Fantasies are part of what gets us to the point of making those first steps out the door, and for that we should be grateful. Of course, nervousness is seldom a feature of a fantasy, but most definitely a part of the first few real life experiences, and honestly, as I found after months of covid-related isolation, the nerves come back again for a while. I liken it to stage fright. Some performers never manage to fully shake it. But eventually, you get into the moment and the nerves pass. Next time will be better, as will the time after that!

Congrats Valerie Louise! What a wonderful evening and you look beautiful! I am looking forward to your next adventure!

Thanks for taking the time to share your very interesting Chicago adventure. You did great, and next time will be even better!

Valerie, please amend the title of your comment to "Not as Expected, BUT EVEN BETTER!" It reads as the tale of a fellow CD who took full advantage of an opportunity to be out there and while you may have run into the same sorts of problems we all have getting ready, you still went forth and enjoyed it. I know I have run into each and every hiccup you wrote about, with the addition of a fire alarm at a hotel just seconds after having gotten completely ready as well as giving up on the little things to make the schedule work.

I have had opportunities to get out and really want to thank all those who have been supportive as well as one special friend who met me out twice this summer. Having someone else to "share" it with is an awesome thing as well, taking you under her wing is something I'm sure you will one day pass on the favor.

The pics show a beautiful woman out on the town, thanks for sharing!

The best laid plans of mice and men...

But, in spite of the hiccups, you did great! I look forward to the day I get out as you did. Thank you for sharing. BTW, you look wonderful and quite charming in the pictures.

Val you look amazing, deep breath, Ive been there several times, cant get eyelashes on, put them in the bin, masscara will do, makeup horrendous, keep it simple, god Val wish I had a dollar or a uk pound when I found myself in your situation, clothes, yes forgot to pack !!!!, deep breath use what you have, dont get flustered, head up high , walk on a pencil line when out, it works believe me. your nobody's business only your own, wear it girl , be confident.

Nothing ever goes as planned. But you did it, congratulations!

We should all be so courageous.

Val, Congratulations. Sounds like a great evening. Makeup always fails when you are nervous. It will be easier next time.

As a reminder to everyone here. When you go out in the public. Nobody cares. They are wrapped up tight in their cell phones, lives, and what is going on in their heads.

We are free to move about. Just yesterday I went in front of my home to collect the trash bins from the curb. 12 noon, full daylight. I looked fab in my new heels and dress. I just do not care and people do not care.

My toes and nail are done 100% of the time. As a matter of fact. I asked my wife if she needed to do her toes again last night and she does not have time. So, I am doing mine this morning alone. What color should I pick this time?

The first step is really the hardest. Good job and looking great. Please keep it up.

Natalie

Val first you look lovely. I remember my first time out enfemme, I was a nervous wreck but at the same time I felt liberated. Keep going out girlfriend it does get earier and that relaxed feeling from your fantasies will become reality.

Practice makes perfect!! Keep going out and doing normal things and that calm relaxed feeling will come. During covid I was working from home. I dressed everyday in what I considered proper office attire (dress or skirt and blouse). I got up to go to the bathroom and walked by a full length mirror. I was startled by the image I saw. I had forgotten I was all dressed up. Took many years but it finally happened.

Nothing is ever how we expect it to be the first time out.
Your account of the evening is quite normal actually and many of us have had that happen more than once.
You look fabulous in the pics and love the outfit.
Next time will be more relaxed I am sure.

Nice to read about an adventure that ended up going well. You look lovely in the pictures.

Thank all of you for your kind responses, and words of encouragement. I definitely feel more ready to get out there on a regular basis now that I made it through the restaurant trial.
I?ll address this to all of you who are putting off the time to go out.
The time is now. We only get a small number of revolutions around the sun, and every day is one lost where you could have experienced something you really want to do. Believe me, if I can do it, you can as well. I?m looking forward to posts from some of the sisters on this thread of their adventures, and I?ll add mine in the future as they come.
Best regards to all!

"The rest of the people paid no attention to us at all. It's as if nothing was unusual. "
That pretty much sums it up. Keep pushing boundaries and expanding your comfort zone.

Valerie,

You may have had trouble with your make-up, nails and lashes but it is certainly not evident in your photos. You look like a lovely lady out for a nice evening. And there is no way you were ever going to be relaxed on your first big trip out in public. It is simply much too exciting an event. The excitement will gradually lessen as you go out more frequently and believe me you will - it gets very addicting. And thanks for posting your story. It was through reading stories like yours that finally enabled me to go out for the first time in public en femme back in April and I am so happy I took that step.

My most recent adventure was going away for a 3 day/2 night trip to a casino/resort where I was en femme the entire time. You can read about it & see a few pics here: https://www.crossdressers.com/forums...-Trip-En-Femme

Hugs,
Fiona

Congratulations, it takes a lot of courage to do what you did. I must admit a fantastic choice of the dress, it's a pure fit in the crowd dress. You look beautiful and looking forward to reading more positive outting stories. Thanks for sharing