Dear Diary: Catie’s Evening Out

Hi everyone! Here is another ‘Dear Diary’ blog post for you all! I had recently brought up the idea to my wife of me going out in fem mode and to my surprise she was generally cool with it. She is supporting my exploration of this lifestyle and was very open-minded about this next step. So luckily enough for me, my crossdresser friend, Devyn, invited me out with her and a few friends while I was in their area for the weekend.

Please read my last ‘Dear Diary’ update to give some context to the continuation of certain topics that I will discuss!

Preparing for the Weekend

I knew about the plans about 3 weeks in advance, so that gave me a lot of time to get myself fully prepared to go out, but I had to do plenty of shopping to prepare. The original plan was to attend a trans group meetup with the theme of it being ‘Pink Pony Club’, so I was on the lookout for pink clothes and accessories!

I surprisingly had nothing pink at all! So I spent a lot of my time thrift shopping for cheap options to wear for that night that would fit the theme. My thought was that I could do a more ‘androgynous’ style for my first time out, a mix of my guy clothes and just make them more fem!

I was able to find a really cute soft pink flowy blazer at Goodwill, which was the perfect option for my target look! I also picked out a few tops that I could potentially wear with it as well.

I was already planning on wearing a pair of skinny jeans that I already owned, so the last thing I needed to pick out was some shoes. I thought about heels, but I wanted a more casual look. I ended up finding a basically new pair of white Keds in my size that I thought would go perfect with my outfit idea.

Lastly, I needed to get accessories! So I found some cute pink press-on nails and some jewelry to go with them. All that was left was to pick the final outfit. That was easier said than done! It was mainly an issue with the tops that I bought. They either didn’t fit me well enough, or they didn’t match the vibes. I ended up overpacking shirts to have as many options as I could because I wouldn’t make the final decision until that night. Being fashion conscious is sooooo hard!

Time to Get Ready

My wife and I arrived at our hotel for the weekend on Friday night, and I had to immediately start getting ready as I planned to meet Devyn at 10 pm at the bar. Plans had slightly changed due to a few different reasons, so now it was just going to be the “after event” that I was going to. It actually worked out better for me, so that I didn’t have to rush to get out, but I had a lot to do before I felt good about my look. I showered and began putting on my outfit and packing my bag with my wig and accessories.

I was ready to leave and was so nervous that I actually forgot my car keys and had to go back to the room!

It was a 40-minute drive to the bar, so I had more than enough time (I thought) to get fully pretty for this outing. Time flew by as I found myself unpacking and putting on my wig while driving, I unpackaged and put on a full set of press-on nails, and applied mascara at the red lights along the way. I commend every woman finishing their makeup while driving, but please, ladies, that is much too dangerous! I almost crashed at least three separate times!

When I arrived at the bar, I put on the finishing touches of some lip gloss and feminized my outfit as much as possible. I looked in the car mirror probably 100 times, took a few selfies, and got ready to get out of the car and walk to the bar.

Stepping Out

I took a deep breath and stepped out of the car, and almost immediately had someone drive by me and roll down their window, which made my heart race. I couldn’t see the guy, but he just asked if the parking was free, and I told him that I thought it was, so I made it out of that interaction without anything weird happening.

I got a text from Devyn telling me that she and her friend Tiffy just got there, so I started walking towards the bar, feeling fully feminine, swinging my hips as I walked. From a distance, I saw who I believed to be Devyn and Tiffy, so I began walking quicker to catch up to them. Just as they got to the doors, I caught up with them and awkwardly tapped on her shoulder. Devyn turned around, and we greeted each other with a hug, and she introduced me to her friend Tiffy. Tiffy is a beautiful trans woman who seemed very nice from our initial interaction.

The Bar

As we walked in together, Tiffy knew some people who invited us over to their table. At this point in the night, drinks were flowing ,and karaoke was the focal point of the night. So as we sat down, I was introduced to everyone. Our table included: Devyn, Tiffy, a super cute gay man, a husband and wife, a cis-woman, and me. It was a pretty diverse table, if I have to be honest.

We all chatted and got to know each other as I was given drinks by members of the table. They all were super nice and complemented my look, including my beard, which I am always very self-conscious about. They also complimented my nails a lot, to which I kept brushing them off by saying that they were just press-ons and nothing special, but I loved the attention I was getting from the group. They also kept telling me that I would be a regular at that bar from now on, which felt a little unrealistic since it is 2 hours from where I live.

We all drank our drinks and sang along to the karaoke, most of which were songs that I did not know. I was just enjoying being out as Catie and having the social interactions that I had been missing. We were there for a couple of hours before I got up to go to the bathroom and finally took some selfies of my look for the night. I felt like I looked cute overall, but I definitely wished that I could’ve gotten a better shirt to wear with the outfit.

When I got back from my bathroom selfies, Devyn and Tiffy were about to leave, and it was getting late, so I decided to leave at the same time. We said our goodbyes to the group and walked out, talking briefly about the fun time we all had. We gave out goodbye hugs and said that we couldn’t wait for the next outing together.

I got into my car and began my drive back to the hotel, slowly transforming back into my standard guy look. It was so nice to lie in the bed when I got back, but I definitely wished that I could’ve spent a few more hours with everyone. There is always next time!

What Is Next for Catie?

I don’t know what’s next! Unfortunately, I had to cancel plans to go out to this bar a couple of weeks ago, so I don’t have any plans now. So I think for me it will just be about trying to get my life back stabilized so that I can have the free time to dress up regularly and start planning for other outings with all of the friends that I have made so far.

Look out for future ‘Dear Diary’ blog posts here to hear about my next outing or meetup with ladies in the community. I am so excited to continue exploring this side of myself and finding open-minded people that I can share it with!