SATURDAY
I was finally able to spend a couple days out and about as Natalie. I mentioned in an older thread that I would be going to Chicago for a few days and that trip finally happened. My partner played a huge part in not only making this excursion happen but also making it a success.
I will note that we took plenty of pictures, and I want to share some with the community. I will be doing so in a different thread in the appropriate area of the forum to ensure this doesn't get bogged down with pictures.
We started off the weekend by going to Ulta for a professional makeover. I made the appointment over the phone and made sure they were fine with doing a makeover for me. They were fine with it and did recomment a Formal Application as opposed to their sort of Everyday look which I was fine with. Not really sure it mattered but it did take a while so I think it worked out.
I had a look in mind that me and my partner found and it may have been a little ambitious but I think Maria (the stylist) made it work reasonably well. The appointment took about an hour and 15 minutes and Maria was kind enough to write down a lot of the makeup she used so I could reference it later. My partner was allowed in the area as I was getting done up which was super nice and every person there, including at least one customer, just treated me like one of the ladies. The other customer even complimented me on my eye shadow!
From there, we went to Transformations by Rori. I had originally wanted to go to her for a makeover but I think there may be an issue with her website as I never heard back from her. And I sort of forgot about it until it was a little too late to try to squeeze in an appointment so Ulta made more sense. And, to be fair, I think I prefered that anyway as I really just wanted a "real girl" experience.
Anyway, Rori was super nice and we found a couple nice things there. I bought a new bracelet. One that actually fit over my wrists and was able to dangle instead of the ones I have that are a little tighter. A nice gold chain and a couple magnetic earrings rounded out the purchases. The magnetic earrings were a bit of a dud unfortunately as I couldn't get the magnets to stay on. But, they weren't expensive so no big deal. Rori did have a lot of wigs, a fair number of shoes (though none that were quite the style I was looking for), and a bunch of clothes. Also not quite my style I don't think. Which comes up later too.
After we were done there, we went to Water Tower Place downtown. It was a fun experience with a lot of people but not so many that it felt like too much hustle and bustle. That is, it felt right and I felt comfortable for the most part. I did spend a little more time than I would have liked looking for a wallet. I had a purse but never thought about a wallet to go in it so I wanted one. I ended up just getting it at Claire's because no one really had any that I liked.
After that, we went into Chico's to look at clothes. I tried a few outfits on that I or my partner picked out and I really fell in love with one outfit. I picked out the pants and she picked out the sweater which worked out well. The saleslady was exceptionally nice and even wrote my name on the fitting room door to reserve it as I tried things on and shopped around. I know she would do that for anyone, but it was fun to see "Natalie" written on the door. And then when we left, she seemed sincere in here question about what we got which was fun to see.
Soma was right next door so we stopped in there and I got a new bra, a new pajama set, my partner and I got some panties as part of their buy 3 get 2 free deal, and then she got two new bras for herself as well. We were the only two in the store and the salesladies were helpful but sort of hands off. Though, when we were looking through bras trying to find our size, they came up and offered help finding the right size in the drawers which was nice to see.
To cap the night off, we went to eat at Rosebud on Randolph and sat in the rooftop section. They had it covered and heated but it was still really nice. The waiter was courteous and we had a wonderful time eating there. I do admit, the atmosphere is great, but sitting in the rooftop was a bit of a mistake. Our food got colder quicker than it would have which affected the experience.
And then we went back to the hotel to wind down for the day. The only bad thing about the day was in the Mall where someone was videoing "something" but their phone was pointed at us. I don't know if he was videoing us or not. He seemed very quick on the trigger to clock me so he may have been videoing something else. I refused to look up into the camera so I can't say. My partner glared at him and he turned around so who knows. It did unnerve me but I got over it.
SUNDAY
The next day was a bit different. We decided to go to the Art Institute and we ended up spending about 3 hours there. This time, I did my own makeup which was daunting but I had some practice prior to this and this was a good test. However, I do admit I was a little less confident in my look that day which may have affected things. And, I didn't use any setting spray/powder so my makeup started coming off later in the day. But, I made it through the Art Institute with no issues and it was a really fun time.
The only thing that popped up was we couldn't get out of the parking garage! We paid for the ticket in the lobby but then it couldn't be read. And the intercom button was broken so we had to go back to the lobby and get assisstance from there and she had us go back to the exit to do the intercom button. I tried a different lane and luckily this button worked and she got us out of the garage but that was a bit stressful to deal with.
After that, we checked out the Woodfield Mall. I was a bit more uncomfortable here. First, my partner had to use the restroom and there was a line. I stood with her in line but didn't actually go in. I didn't feel too out of place and no one made any comments about me being in line which I will take as a win.
But I really wanted to go to Victoria's Secret since we have a bra from them my partner and I like and I wanted to get another. We walked around but it really felt like we were being ignored. I doubt that was completely it, but there was a bra I wanted but couldn't find the size and we were hoping someone would come over to help but no one did. So we never found it. There was a situation where we were looking at bras and a saleslady started talking to my partner but never once looked at me. I am sure I am manufacturing things here but it did make me a little uncomfortable. They were busy and it was only 45 minutes to close so it was probably just that, but it seemed odd that she wouldn't have spoken to both of us "ladies" if she was trying to make a sale.
In any case, the store was busy enough that we didn't want to stand in line that long anyway so we left. We went to Primark since I had never been to one and I found nice sweater. But I again felt a little more uncomfortable here and it seemed I got a few more looks. Plus, Primark really doesn't have a lot and definitely does not have my style so we did what we could and got out.
We checked out a shoe store and they had a sale on Hey Dudes which I was considering since my feet were killing my in the heel boots I was wearing. I might have been a bit too ambitious with those so I wanted something more comfortable for next time. The salesman here was awesome. He addressed us, introduced himself, asked our names, etc. Did what he could to make the sale and be polite. Unfortunately, the shoes I wanted were just on the tight size and they didn't do anything over a size 12 in women's so I couldn't try anything else on. But he was super nice when I said they were a bit too small. He even said that the men's come in larger sizes but aren't quite as cute as the women's so he understands not wanting to just go with men's. Overall, a very satisfying end to otherwise somewhat poor shopping experience.
On our way out, we did hear a young man shout "What the ****!" as we went by. My partner glared at him but he didn't seem to be doing much to point me out so it is possible (and probably) he was talking about something other than me. It is just hard not to assume those exclamations aren't about me.
On the flip side, as we got to the doors, a girl passed us and did a double take at me but then smiled and looked away. Who knows if it was sarcastic or genuine and it was clear she clocked me, but even just looking away without a look of disgust was empowering after the potential comment about my from the young man.
We finished off the night at Enterrium with dinner and arcade games. This was probably the most interesting interaction of the two days. The server was very polite and even asked if I was the librarian from a local library! I have a feeling she was trying to make me feel better but even the thought of making her think I was a different woman was endearing. And she made a very conscious effort throughout the night to address us both as "ladies" whenever she came to the table.
She did slip up at one point and called me "he" but immediately corrected herself. I am definitely not going to begrudge her that. My makeup was thinning and I am still working on everything and she immediately corrected herself so no harm no foul. Honestly, knowing she clocked me pretty easily and still going out of her way to treat me like a lady made me feel even better about things. I don't always have to be perfect as most people are likely going to be accepting and try no matter what.
We then headed back to the hotel to finish out the last night as girlfriends. I was back in boy mode for the next day and a half before coming home.
SUMMARY
All in all, this was a very successful outing for Natalie. No real issues popped up and even the ones I think may have occurred could have been me overreacting. Or I could be right but, in the end, I guess it doesn't matter. I had a good time and having my partner there to have my back during all of it made all the difference in the world. We are already talking about when Natalie is going to go out again and even some vacations where Natalie can make even more of an appearance. We can only do so much because my partner really likes taking and sharing pictures on Social Media and Natalie is definitely not ready for that yet.
I would say that I am still trying to find my style and, more importantly, where to shop for that style. As mentioned, Rori didn't quite have clothes that fit my style, Forever 21 isn't quite right either, and Chico's goes a little further the other direction from Forever 21. My partner mentioned that department stores are probably my friend right now and I have to agree so maybe the next time Natalie goes out, it will be to try those places out a bit more.
crossdressing...theirs an app for that 
, What a great story, I have yet to go Out, >Orchid**O
O**
