Finally found some time today to blog about my first "real" dress out experience. If you may recalled, I did tried dressing out around end of 2021 with the help of Winnie. However, that experience was more like a 15 minutes of "fame" where I walked around the building where my lair is located. Winnie and I walked around industrial estate and as it was the first time I tried walking in heels plus my first time dressing out, I was pretty nervous and my feet was hurting. So after a while, I got to call it a quit. I have to admit that I was pretty disappointed with myself back then for not leveraging on that opportunity to dress out and explore more.
Fast forward to yesterday (27th Mar), the stars were aligned. My wife is in overseas and I made all the preparations to be "single" again for about a week. Happening at the same time, I joined a Telegram group for SG CDs recently. It is an active and fun group where CrossDressers (CDs) or Transexuals (TS) can chat and share and of course, to organise outings and gatherings. It just happened that there is a CD friendly pub/bistro around Chinatown area that is closing down and the organiser Jacelyn (another of my CD idol that I will love to meet) decided to have a gathering there. Sensing that this is the one chance for me to dress out. I decided to pluck my courage and take the purge to join the gathering.
Preparation for the meet up started a few days before. In fact, on the weekend when my wife flew off for her business trip, I went to my lair to practice my dress up and find suitable clothing for the gathering as it has been months since I last did a real proper dress up. It just happened that there was a meet up over that weekend also. I planned to step out from my lair and drive down to meet my fellow CDs at the pub/bistro. I was all dressed and ready to step out from my lair when I heard my neighbouring unit tenants coming back to work... I was thinking, who would work on a weekend night around 10pm... That really dampened the spirit but I held steadfast, hoping that my "neighbours" will somehow leave soon. Ended up, I can hear them packing and sorting things outside the common area... In case you were wondering, why I never just walked out. The problem is, my "neighbour" saw me before when I was moving in to my recent unit (read about my recent move in my last blog post here...). Ended up, I waited till 12am in the morning and decided to give up waiting and started to dress down and remove my make-up... I just packed my clothing into a cabin size luggage and went home.
For me, first time dressing out is no easy feat. I have to check if there are any hotels nearby the meeting place for me to dress up and walk over. I was quite lucky to find one that was just a stone throw away from the gathering location. Without thinking much, I just booked the hotel. On the day of the meet up, I was all excited and ready. Luckily it was a Monday, so I decided to Work From Home instead. Around 4:30pm or so, I just grabbed my cabin luggage that I packed over the weekend and drove down a carpark nearby the hotel and parked there. I quickly checked into the hotel and checked my phone for any updates regarding the gathering.
Not long after checking in, I decided to prepare for dress up as I sensed that I might need more time as the hotel room was quite small and does not have a proper table for me to do my makeup. I took a shower first and do a quick shave down before working on my makeup. First was the contact lenses, that took me a long while. After that, I started working on my face. All these while, I was sitting on the floor and using the bedside table to put my mirror for my makeup. In the end, I gave up and decided to do my makeup using the bathroom mirror as it is larger and in a brighter area. After doing up the face, I realised that the other sisters would not be there until 9pm. So I decided to take a short nap with all my makeup still on. Haha...
As time slowly ticked by, I decided to start dressing up and make sure I was all ready and set for my first dress out as Francesca. I was all excited. Initially, I was liaising with Jacelyn to meet me around the hotel and walk over to the pub/bistro as it was my first time dressing out, I was not that confident. So I thought that if there is another sister around, it will definitely boost my confidence. However, after a while, seeing that some of the sisters had arrived at the location and not wanting to trouble Jacelyn. I decided it is make or break. I checked and made sure that I was not conspicuous and can blend in easily into the night, I put on a face mask (all thanks to COVID, wearing of face mask is no longer weird) and took my first stride out of my hotel room door.
As I walked towards the main hotel door exit, my heart was pounding hard. I told myself, "I am all okay. I got my face mask on and I am not overdressed, no one will notice me." As I stepped out of the hotel door exit, I did get a bit of anxious. I just looked down on the floor when I walked, tried to avoid eye contact or making too much movement that would get attention onto me. I walked like less than 100m and I reached the meeting place. At first, I was a bit lost as to who to look for, but I guessed the waitress knew that I am a CD and meeting up with other CDs. She just led me inside where I saw some of the sisters who were already there. They were drinking and singing KTV. I was still quite nervous and shy about this whole experience that my mind was a bit blank. Once there, I removed my face mask and introduced myself and I just ordered a Coke to drink and took a seat with them. There I saw Ashley, Lulu, Candy and Stephanie. As the music is a bit loud, plus my poor hearing due to prolonged exposure to loud noise at work, it was a bit hard for us to chit chat there. So I do apologise here if I appear unapproachable that day.
As time went by, I started to get more comfortable with my first dress out experience. After a while, Jacelyn came and we decided to move to an area away from the KTV singing towards the drinking area at the front of the pub. I was just enjoying the music and taking photo of my first dress out experience while we waited for others to arrive. In the meantime, we chatted and enjoy the drinks and light tidbits.
Not long after, another CD sister, Chanel joined us but in guy mode. It was also her first night dressing out. She was all shy and quiet initially but when another sister Yuki arrived. She really brought up the mood and atmosphere. We encouraged Chanel to go to the toilet to dress up while the rest of us just enjoy the night with the drinks, music and each others company. Throughout the session, we were chatting about our CD experience, the CD community in Singapore as a whole.
After a while, Chanel completed her transformation and join us at the table, she is so slim and petite size. Really admire her. I was really amazed with all the sisters there that night, they all looked great. I was still in awe how sister Yuki could walk in that 5 inch stiletto heels. However, as the night drew to a close plus tomorrow is a working day for most of us. Yuki and I got to leave early. Just coincidentally, Yuki also gotten the same hotel as me.
We bid farewell to the other sisters before proceeding back to our hotel room. I was walking behind Yuki when heading back to the hotel. I found out that Yuki's room was just next to mine. Such a coincident. We retired back into our room respectively while I did a bit of selfies before removing my make up and calling it a night. I had decided to stay for a night and wake up really early next morning to go back home for work.
It had been wonderful first dress out experience for me as I managed to meet up with a few sisters in the CD community in Singapore (especially Jacelyn!!!) and the gathering place is really conducive for CDs to meet as the boss is really welcoming and does not discriminate against CDs or TS. Unfortunately, the pub/bistro is closing down soon...
Anyway, I really hope to have more opportunities for me to dress out next time. I do not know when will that be, but I really do hope that somehow I can find the opportunity and time to do so. Really nice meeting up with the sisters, namely Stephanie, Lulu, Candy, Ashley, Jacelyn, Yuki and Chanel. Hope to be able to dress up and meet up again soon. Cheers.
Just to share some of the photos taken on my first dress out session.
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