My Journey (Part 6) - My first time in public as a girl
(I wore 4.5-inch heels the first time out. Highly NOT recommended if you lack practice)
Looking back, it is pretty amazing how far I have come on my crossdressing journey. If I were to ask my younger self if I would go out in public dressed as a girl, it would have be unfathomable. I've no regrets to do so, because it is very liberating to go out in public and do simple everyday stuff like shopping. The first step out in public is always the hardest, but one of the most memorable.
Since the eventful big reveal to my wife about my crossdressing on 16 June 2018, many things have happened. My wife saw my female self for the first time ever. I have my own wardrobe of girl's clothes (hung up and arranged according to colour), I started getting a bit better at make up after more practice and I started ordering clothes online to be delivered directly to the house. The next major milestone for me was stepping out into the public's eye as a woman.
This started with me going onto the now defunct SG Butterfly forum to chat with like-minded individuals who were interested in dressing up. It was great that the conversations were pretty decent (moderators clamped down hard on soliciting of sex and NSFW content), so it was just clean chit chat about crossdressing. Up to that point in time, I had never really communicated with local crossdressers, so I was pretty curious to meet up with a few in person to find out why they crossdressed, how they dealt with life and a bit more on the local community. Of course, I made sure to tell my wife about my intentions and got her approval to meet other sisters within the community before I did so.
The first time I ever met fellow crossdressers was on 27 Oct 2018. It was the halloween weekend (a.k.a the holiday season for crossdressers), so it was timely to plan for an outing in public. At that point in time, my goal was just to dress up and chit chat indoors and I had zero intention of going out in public. The organiser booked a small room in a 3 star hotel as a private place to transform ourselves from normal guys into girls. The room was clean, but was tiny and felt a bit budget. Nevertheless, it served its purpose as a base to dress up. Including myself, there were a total of four crossdressers during that meetup, and it was the first time anyone in the group had met each other. After a brief introduction, everyone started find a corner of the room with a mirror to put on their makeup, which was made slightly challenging with the dim mood lighting of the room.
I brought a few outfits that day, but my best outfit was my New Look black off-shoulder bodycon dress. The other sisters also gave a nod of approval to this outfit
(The exact dress I wore in public the first time)
By the time we finished dressing, it was around 7pm at night. Unsure if we were going to go out dressed, we decided to order in a large pizza for dinner, but even though there were four of us, we couldn't even finish it. Maybe everyone was more in the mood to dress up and less interested in eating. Also, pizza really isn't the best type of food to eat if you want to keep you makeup intact.
After about an hour of chatting, the mood started to feel like we couldn't be cooped up in the room for another hour. After all, everyone was dolled up and it was a waste not to go out. Two of the girls were also really keen on going out in public to one of the LGBT bars to check out the halloween festivities. After a bit of internal debate, I too felt that halloween weekend was really the best time to go out crossdressed. Despite the dress showing my rather broad shoulders, I still felt quite passable that night (looking back at photos of that night...I think I have improved a lot since).
When we all stepped out of the room, my emotions were a heady mix of excitement and fear. I was out in public as a girl! Nevermind that it was just a hotel corridor. As a dragged my suitcase and glided down the hallway in my LBD and 4-inch heels, I felt like I was an air-stewardess who was just about to check out of her hotel. But I was also incredibly nervous, which made me glance down slightly and away when the hotel staff suddenly appeared in the hallway walking towards me. Being in public also made me hyper self-conscious; of how my hair was like, how I stood, where I placed my hands, the way I walked, etc.
Fortunately, the lift lobby led directly to the carpark and within a few minutes we were all safely in my car. It was convenient since we didn't need to squeeze into a cab, which would have made me feel even more awkward. As my nerves calmed in the car, we set of to our intended destination, Tantric.
(Tantric bar. It was a bit emptier when we first arrived, but it gradually became this packed)
I parked in a nearby public carpark a short 50m away from the bar. But because it was my first time out, I had to steel myself for what felt like a really long distance to me. As I swung both legs out of the car and planted my heeled feet on the tarmac, it dawned on me that brisk walking was out of the question. Silently cursing my poor choice of shoes, I followed the lead of the other girls, teetering in my heels towards the club. The side walk was pretty narrow, so I pretend to look away or at my handphone when other people walked by in close proximity. Where were all the people in halloween costumes!? Everyone was dressed in very normal clothes.
Finally, we reached the entrance of the bar. The bouncer was checking everyone's bag prior to entry. When it was my turn, the bouncer said "Miss, your bag please." OMG. It was the first time another person called me "Miss". Although I was pretty sure the bouncer knew I was a guy, I still felt super validated! It was awesome. I held up my black handbag (very feminine, yay), which he shone a torchlight in it before waving me in.
(Inside the bar. We were just sitting in one of those booths and I was just feeling perpetually self-concious)
At the bar, we found a booth with high chairs and sat down, before we each ordered an alcoholic drink. Even though we were in a safe space (it is an LGBT bar after all), because everyone looked so normal and I didn't see any other crossdressers around, I was just content hiding in my booth, trying to have a conversation with my sisters over the loud music. The only time I left my seat was to drop by the unisex loo (it felt so weird waiting for that ONE stall) together with other male customerd in the same tiny toilet. We ended up spending 90% of the time at the table pretending to be invisible and 10% of the time walking around trying to look for a more comfy place to hang out and talk. Not the most fun experience as far as trips to bars go.
As the bar became more crowded, we noticed more people in halloween costumes and a few drag queens in the bar who were slated to perform later in the night. A very friendly drag queen dressed head to toe as a cheetah (I think she is Dahlia Rose. I remember her huge gold choker with "Dahlia" on it. She looked absolutely regal in her outfit) saw us and started chatting with our timid group, complimenting me on my shoes, look and how she loves her "fishy girls". It was the first stamp of approval from an experienced drag performer, which made me rather happy. It was pretty nice to actually try socialise with someone in the bar. We hung around to chit chat a bit more, but eventually though it got really crowded and warm around midnight, so I decided to call it a night.
Parting Thoughts
Although the outing went pretty well, on hindsight, it was probably not too great an idea to meet a group of strangers for the first time in a hotel room. It's probably the only place most crossdressers can dress up safely, but in a different country other than Singapore, such a scenario could have gone horribly wrong. Even in Singapore, it is probably better to be safe than sorry too. I've since adopted the low-risk policy of not meeting other crossdressers I've never met before in hotel rooms.
That having said, I was pretty happy that I got dragged out of the room despite my initial fear and misgivings. Tantric was a safe space, and I should have been more daring whilst at the bar and chatted with others (or joined in with those who were dressed up), since it was Halloween and people were definitely less judgemental. Perhaps the next time when Covid-19 has blown over and Halloween comes around again, the mousey Isabelle will be no more; instead, reborn as the sultry vampiress 🤣
6 Comments
Nice, maybe one day I will dress out when I ever muster the courage to. I guess I need to meet other sisters for that support.
ReplyDeleteIt's not a must to meet others, but it does give a bit of a push factor. I do think that starting with a safe space like an LGBT bar is always good
ReplyDeleteOmg! this is the bravest thing i have seen anyone do !
DeleteI really like your blog and your recent video on crossdressing, keep up the great work!
Great article. Congrats on your dress out. I was in SGButterfly for many years too. Very sad that it is defunct and I lost many contacts
ReplyDeleteYour outing story sounded very familiar to me, I met with a group of sisters at a hotel, some dressed up there, and we walked over to Tartaric and it was also Halloween time. Does it sounds as if we could have been there the same night? Haha ... as I check on my FB posts, I was there in 2017, the year before you. I remember looking forward to go back there the next year, but due to some reasons, we didn't get to arrange another Halloween program in 2018. Thanks for writing, it helps to bring some fond memories.
ReplyDeleteI can relate to quite many parts of your blog, except this part. Considering I never meet face to face any CDer till I already fully decided to transition. And even then, it was not much. Work on your voice bah. Its a make or break.
ReplyDelete