My Crossdressing Journey (Part 13) - Being more comfortable as Isabelle in public

by - March 27, 2022

It's been quite a few years since Isabelle first stepped out in public. I still remember the thumping in my chest, the fear of being recognised as a guy wearing a dress, the shame when someone stares at me for longer than usual and the euphoria of unexpected validation. But mostly the fear, which wells up from the gut up to your throat and paralyses both the mind and body. The first time out in public was so very scary. But I've gone out in public many times since that faithful Halloween of 2018 and I feel a lot less stressed when I do so now as Isabelle. 

Don't get me wrong, going out en-femme still has its stressful moments. Stepping out and returning home as Isabelle is always the most stressful because I really don't want my neighbours to see me. I still don't like eating out as Isabelle because I'll be seated in close proximity with other patrons who can gawk at me with impunity (more importantly, the long hair really gets in the way). And being stared by multiple uncles/aunties in quick succession at the shopping malls still throws me off a bit. But I'm no longer uptight about stepping out and feel relaxed most of the time. There are a number of reasons why this is so. I've gained more experience being out in public and honestly, Singapore's a pretty good place to crossdress since it is safe and people generally mind their own business. I've improved my skills since 2018 and confident that my style allows me to blend in the best I can. I'm also a bit older too, so there is the element of YOLO where I don't really care as much about whether people realise I am a guy in a dress or not. To top it off, mandatory mask wearing due to the Covid pandemic has allowed me to hide my manly lower jaw and larger nose, which helps me to blend in even more. 

Although being in public puts a crossdresser in a "riskier" position of being recognised as male, a lot of this risk isn't consequential unless it is a partner/friend/relative/colleague who recognises you. And usually if it is your friend, I'd think they'll generally be understanding and supportive of what you do. The upside of going out in public en-femme is that I get to do a lot more regular day to day things as a woman, with shopping right at the top of the list. It also creates opportunity for validation, which is something that so many of us crave. These moments are usually fleeting and insignificant to any other observer, but to us crossdressers who aren't fully out yet, it means a lot. Even something simple like being called Ma'am by the bouncer at the club during my first time out in public was validating. My makeup was middling at best, my wig was unnaturally shiny and I could barely navigate in my 4 inch heels, but it still felt great. 

I've since had multiple occasions where I interacted with other people who seem to be perfectly comfortable with Isabelle. A sales assistant giving me a small nod and smile when I picked out items to try in the changing room. The bridal studio's makeup artists and photographers who were casually chatting with me throughout the entire photoshoot, occasionally telling me that my female self looks pretty decent (service for the paying customer perhaps. But the comments didn't come across to me as fake). I've also had a lot more close encounters with random strangers recently when I visited iWan Selfie Studio in March 2022, due to the relatively small studio and the close proximity which I have to be in with other patrons. I don't attempt to use a "girl-voice", so whenever I spoke everyone else in the room would be able to clearly tell I was a guy, but none really bat an eyelid about it. Most of the ladies just gave me a smile when we occasionally made eye contact and went back to busy themselves with dressing up and taking selfies/tiktok videos. 

Two episodes at the selfie studio were especially validating. The first was when I overheard a bunch of 3 young chinese gals commenting among themselves about wanting to take photos in the 2D themed room I was in. I wasn't too keen on the room so I told them they could use it and one of the girls went "Ehhhhh, 你是男生!" (the Chinese equivalent of "Omg you're a guy?!"). Inside I thought to myself, YESSSS I passed 😆 (the ladies were quite self-absorbed so they probably didn't pay me much attention earlier). Another episode was during my 3rd visit to the selfie studio on a weekday, when a gaggle of aunties in their 50s who were just done with their session were hanging around the lobby and chatting with the owner about the package prices. I had picked out a sequined bodycon dress which fitted me surprisingly well and started taking photos in the kaleidoscope tunnel. A few of the ladies started observing, commenting to each other out loud about my slim figure, about the poses I did, how experienced I must be, about the more professional mirrorless camera used (It was very Singaporean auntie behaviour). I was so embarrassed and taken aback when 4 of them suddenly whipped out their own phones to take photos of me, that I stopped my own selfie-taking to engage in a bit of a conversation with the curious aunties. It turned out they truly thought my look was well put together and just wanted to take some photos (unacceptable from a personal privacy standpoint, but understandable when you view them as harmless Singaporean aunties with a compulsion to take photos of anything and everything). One of them requested for me to take a selfie with her, while another requested for me to do a twin pose with her in the kaleidoscope tunnel, both of whom I obliged. Another eagerly showed me the slow-motion view she took in the starry theme room and told me I absolutely had to do the same thing. They were also genuinely interested to find out how I remotely controlled my mirrorless camera using my phone. I resumed my phototaking, which got a few more ooos and ahhs from the aunties before they left for their belated lunch.

To suddenly have random people wanting to take photos with me because they thought I looked pretty was incredibly weird but trippy. I've never had so many compliments about my looks in my entire life, which threw me off but definitely felt validating. I know this all sounds superficial, but there is a tinge of pride when I think of the effort I put in to pass and how far I have come since my pre-coming out days. When I shared the strange episode with my wife later on, she quipped that I was the drag queen in a sequin dress that everyone wanted to take a photo of post-performance (LOL 😂). Perhaps that was the reason why they wanted to take photos of/with me. I'm uncertain if the aunties figured out that I was a guy or not though. Some of them surely did but never mentioned to me. But being able to just engage people normally without them sounding weirded out or giving me a puzzled stare is great. 

(Not me nor fellow friends, but I'll get here someday)

I wouldn't start putting myself in situations where I have close encounters with others, like going to a bar and actively chatting with others. Although most people wouldn't mind, not everyone is so accepting of crossdressing behaviour.  Nor do I want to be out to my family/friends yet, and sure as hell not to my work colleagues (Knowing about my dual-life as Isabelle still remain a "need-to-know-only" basis). But I'd continue to do more regular things as Isabelle and enjoy every moment of being her without a care of being clocked (up to a point). And if there is a need to strike up a conversation with others in my baritone, I definitely wouldn't mind doing so.

You May Also Like

0 Comments