Surprise while exploring dressed

I had been dressing at home for a while, taking pictures and enjoying myself. Usually whenever I had any sexual encounters I was not dressed and had a mixture of experiences as top and bottom. This is the day it all changed though.

For the first time I decided to get myself dressed and head out. I picked a nice outfit, not too slutty but the skirt was flowing and my top was cropped and tight. Showed off my figure nicely. Nice long black hair and decent makeup.

I decide I’m just going to head out and grab a coffee first to see where the day takes me. It had been late afternoon when I left the house so by the time I had my coffee and a nice walk around town looking in some shops it was getting to be dinner time. I decided that I would head in the direction of some restaurants/bars for a nice dinner.

I find myself at a local restaurant which has a bar too. I had not made any reservations so was having a drink at the bar waiting for a table. As I was drinking and on my phone all I could think was “this has been an amazing day!”. I had been out free just having a day and feeling sexy.

While waiting, I was approached by a very good looking guy who had just been shown to the bar to wait for a table and he asked me if the seat next to me was taken (it was a busy bar) and I said happily “No not at all, I’m just out solo today and I’ve been having a great day!”.

We started to talk and had a couple drinks together. He had complimented my looks a couple times and so had I. My heart started to go a bit faster when he complimented me. As we got into drink 3 something in me decided to reveal to him that I was out dressing for the first time. I had no idea what his reaction was going to be but just went for it. He was definitely surprised but then said “you should be out showing the world this side of you more! You’re beautiful” I blushed and said thank you. After this he didn’t draw back or end the conversation at the earliest possibility. Which was amazing. I found myself thinking “could I take this guy back?”