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Musings of a Singaporean Transgender


These days, I almost exist entirely as my regular uncle self "Bob", since I don't dress up much. But Belle still lives rent free inside my head, reminding me of her presence in many different ways on a near daily basis. Which made me wonder...how would it feel as a "regular" guy, with no female alter-ego and no gender dysphoria? It is unfortunately, an entirely hypothetical question, since people with gender dysphoria will never get rid of it, and regular guys will never get to feel it. 

We spend so much of our waking hours thinking about gender matters; in youth, we wondered why we wanted to literally be in the shoes of the opposite gender, struggled with feelings that such thoughts were deviant and weird, yet circling back to think about them again and again.

We deal with the fervour of wanting to dress as our female selves on a regular basis and obsess over creating opportunities where we can do so. This fervour is especially bad when there are long dry spells, but the withdrawal post dress-up isn't great either. 

When we finally get to dress as our female selves, we fret about imperfections in our makeup and attire, overly magnifying all the masculine attributes we think will cause us to get clocked. We worry that our feminine-inclinations will be discovered by people we know and be branded by others as a pervert or a weirdo. 

We deal with varying degrees of body dysmorphia, being concered about appearance related issues that plague women, like weight, height, skin, attractiveness...except our base template is male, so the gap between our current and preferred looks is usually even larger. There's always unhappiness with certain parts of the body and the envy that comes along with it. Do you know how damn annoying it is to see a pretty girl on the train and think "I wish my skin/features/hair was as good as hers. But that will never be possible. Oh well."

In the pursuit of validation of our female selves, we turn to social media. But use it actively for a year and you'll realise that it's a horrible source of validation, a wellspring where drinking from it only sates you momentarily, but makes you thirst for validation even more (via comments and likes), leaving you feel a bit hollow inside.

So much of our time, energy, effort and mental bandwidth is spent because of gender dysphoria, soothing it in one moment and fighting it in the next. Life without gender dysphoria would be so much easier I think. Much less guilt, fear, discontent and obsessing over gender stuff. Just need to be a regular guy doing regular bro stuff. 

The short answer is, it depends.

Recent events triggered me to write this post. A close friend of mine in the community went for his first session of couples' counselling as he was facing some marital issues regarding his proclivity to wear women's clothes. While the counsellor did caveat that his (or her) understanding of the situation was limited, my friend's desire to wear women's clothes was described as an "addiction", and it was suggested for him to remove all sources of temptations in the short term while they work out the marital issues. As my friend's wife had also given him an ultimatum regarding his crossdressing, in order to preserve his marriage he decided that drastic measures had to be taken. A full purge was carried out; deletion of all his female alter-ego's social media accounts, giving away his hoard of women's wear built up over the decades, as well as cutting off all contact with friends in the community. 

I don't know who the counsellor was nor did I get the full story, but hearing the description above got me incredibly riled up. While I knew my friend was in a difficult situation and had to make tough choices, the callous commentary from the counsellor was setting my friend up for failure. By using the negative term "addiction", it labels the desire to wear women's clothes in a similar way as drug addiction, where the path to recovery is cold turkey. It also gives confirmation from a "professional" to my friend's wife that wearing women's clothes is something to be purged from his life. Even if the counsellor later becomes more learned about gender dysphoria and corrects the advice given, the damage is very likely done. Knowing my friend, he's quite a good way down the transgender spectrum even if he doesn't recognise it or care to admit. While he might be able to keep a lid on his urge to wear women's clothes for 1, 2, or even 5 years, the dam will eventually break and he will put on a dress once again. Should his wife discover it, he would be seen to have "relapsed", and the cycle of shame, guilt, disapproval, sadness, purging and suppressing will happen again. 

I was feeling angry for a day, but decided to reassess the event a bit more objectively. Merriam-Webster defines "addiction" as follows. 

Addiction: a compulsive, chronic, physiological or psychological need for a habit-forming substance, behavior, or activity having harmful physical, psychological, or social effects and typically causing well-defined symptoms (such as anxiety, irritability, tremors, or nausea) upon withdrawal or abstinence : the state of being addicted 

My own desire to dress does appear to fall within the definition above at times. While it has not affected my ability to function normally, nor did it cause harm to my personal being, not letting Isabelle out for extended periods causes me to be increasingly obsessive about creating opportunities to do so. The feelings of withdrawal were more apparent prior to coming out, when opportunities to dress was significantly limited; confined to periods where everyone was overseas. Missing an opportunity meant an agonising wait for weeks or months before the next window opened up. After a dress up session, my desire would be momentarily sated, before the urges gradually creep back again and I pine for the next opportunity. 

The desire to dress as a woman is also generally viewed as negative; "Men shouldn't wear women's clothing, it is unnatural / abnormal / perverted / a sin / an embarressment". So when I give in to the urge to do this "negative" activity time again and again, it isn't hard to view it as an addiction. Nobody ever labels a voracious reader as a book-addict, or an avid gardener as a plant-addict. But deny them their books or gardnening for months and they'll start to pine for it with great fervour. The difference is that reading and gardening are "positive" activities that one can do in copious amounts, even encouraged. 

It doesn't help that the urge to dress builds in tandem with sexual arousal, and wearing women's clothes is usually an incredible turn on. The result is usually a conflicted, struggling, self-shaming individual. If dressing as a woman is so bad, why does it feel so damn good? If it doesn't hurt anybody and makes me happy, why is it so wrong? How can willpower alone be the dam to hold back the rising water levels of desire?

A common argument is that "These men have a choice. They just chose the easy way out and gave in to their addiction to wear women's clothes.". 

But do we really have a choice? Sure, I can choose a shirt over a slinky dress today, tomorrow, weeks and months on end. But deep down, my identity is female and I yearn to be recognised as such. Denying myself the dress is tantamount to denying my identity, which I can do for some time without causing discomfort and pain to my being, but not forever. Most people who do not experience gender dysphoria do not even think about gender; it is a fact that does not need questioning. There is no need to deal with regular thoughts of wanting to look different from their assigned gender at birth. If I could, I would prefer not to have gender dysphoria. It would make life a hella lot more straightforward. 

So in my view, a guy's desire to dress as a woman has some hallmarks of what an addiction is. But when viewed through the lens of gender dysphoria, it becomes harder to label it as such. If the need to be female, even momentarily, is as essential as food for survival, then perhaps calling it an "addiction" isn't exactly accurate. Things aren't so black & white. 

As for my friend, I hope that in his new phase of life he is able to settle into an equilibrium that he is comfortable with. While I have doubts that his female alter-ego will fade into memory, perhaps she wouldn't torment his waking moments daily. 

Hello fellow sister,

This is a letter to you, especially if you're relatively new to crossdressing or have been in the closet for the longest time. 

While our origin stories and the winding routes that we take through life are different, we all share a single commonality; our penchant for wearing women's clothes. It may have started inexplicably when we were 5 years old, or it only started in our 20s as part of a dare. But regardless, the activity of dressing up as a woman brings us great joy.

There is an unparalleled thrill solely reserved for us crossdressers when we unwrap our online purchases, to slide that new little black dress up our body and step into a pair of stilettos. The heart thumping in the ears and the quivering fingers as you feel the rear zip enclose your body in the dress. How is something deemed so wrong by society able to feel so damn right?

We live in a world that isn't fully accepting of our proclivities, but it is slowly changing. For the Singaporean readers, while our country is conservative and generally does not encourage expressions of gender identity beyond the binary, it is a relatively safe place to be if you are a member of the LGBTQ community. Some domestic violence or ostracisation is still present, but we don't need to be worry about having a gun pulled on us if we go out in public. With easy access to information on the internet, each generation is becoming more aware of the gender spectrum and non-binary nature of sexuality; with awareness comes greater ease of acceptance and gradual normalisation. While the reality is that male to female crossdressers and others in the transgender spectrum face the biggest challenge, we are progressing forward, inch by inch. 

Take your time to figure our who you truly are, your likes/dislikes, your tastes and desires. You might identify as transgender, femboy, non-binary, sissy, genderfluid, crossdresser or any other labels that society has conjured up over the years. You might be sexually attracted to women, men, both genders and everything in between. Or you could be confused about your inclinations, swinging from one to the next. In your explorations you may realise that your sexual appetite is kinkier and more out of this world than what most folk can imagine in their wildest dreams.

And that's ok.

You might be much taller or larger than most cis-women and extremely self-concious about certain parts of your body that holds you back from going out in public. While being petite and slim does help in being passable, watch a few seasons of RuPaul's drag race and you'll realise that the biggest or buffest guys can slay on the runway. And remember that cis-women also come in all shapes and sizes.

Many of us carry around a mountain load of shame, built up over the years. Shame for seeing a pretty girl and wishing you were her instead of your rougher male self, only to chide yourself for not being a "real man", being weak for giving in to such sinful thoughts. Shame from passer-bys' lingering stares that confirms the niggling thought at the back of your mind; that you aren't passable and people easily recognise you as a guy. Shame for wanting to do what society deems as "depraved". It's very normal to feel that way after years of programming by society to behave a certain way. I'm still working through my shame, so continue to work on yours too. 

Remember, this is your life. While we are accountable to the people closest to us and have different responsibilities, this is the only life we have and we have to live it to the fullest (sorry readers who believe in the afterlife or reincarnation). So make plans to be financially secure and enjoy the female side of you, hopefully in public too. 

Most importantly, love yourself, always.

We are all cis-men who love to wear women's clothes, and that's ok. After all, women's outfits are f***ing gorgeous and better than boring men's clothes 😆

Yours truly,
Isabelle

I was only ever caught once by a family member for wearing a dress. The details of the day are a bit hazy; I was perhaps around 5 years old. I remember I was playing with my sister. One of us initiated that I try on one of her dresses. I don't remember how it looked, except that it was a white, red and blue flared dress. What I remember vividly to this day however were two distinct feelings. I felt very pleased and pretty when I wore my sister's dress. And I felt an incredibly intense shame when my grandmother caught me in it. I knew it was wrong; boys shouldn't be wearing dresses. I remember scrambling to hide in futility when I heard her coming from the living room, fearing that she would find out. When she told me that boys shouldn't wear dresses and asked me to remove the dress, I dearly hoped that she would not tell my father about it. The incident put me off so much, I never touched dresses or skirts for a long while after that.

A lot of the shame we feel as adults start off as simple boundaries that we learn as children and are reinforced over the years due to the way society is set up. Because these gender boundaries are so deeply rooted, the feelings of shame and the fear of deviating from accepted norms is typically intense. Both genders are subject to different types of "programming" from young, but for this article I will focus on boys, since that is my personal experience. 

Boys wear pants and girls wear skirts. Boys aren't supposed to like dresses and dolls. Boys aren't supposed to like pink or anything with ribbons or frills. Boys cannot cry because they should be strong. The list goes on. We praise little boys for feats of independence and bravery, chide them for actions or choices that are decidedly "female". 

Shame, is a natural result of shaming. And this shaming starts as early as kindergarden or primary school. Effeminate boys are ridiculed as gays, sissies, bapok*, ah-gua* and all manner of derogatory terms. "Why don't you dare to do <insert daring activity by children's standards>? Are you gay / a sissy?". Revealing any inclinations or curiousity in feminine accoutrements results in immediate teasing from peers and possible social ostracisation. Kids really are brutal. Only the bravest revealed their true selves and I was not one of them. I was a nerdy kid who just wanted to fit in and be liked. While I didn't partake in any shaming or bullying of others when I was at that age, I was fearful that hanging out with any who were slightly effeminate would cause me to be similarly ostracised. I also avoided anything that might suggest of my inclinations; no clothes with feminine colours, trying to be good at sports, etc. I even remember feigning boredom and pretending to be utterly uninterested when watching a transgender performance ("ladyboy show" as they were known) when holidaying with parents in Chiang Mai, though deep down I was enraptured! What beauty and what glorious outfits they wore! Note that these were the days of dial up modems, so I had near zero access to information to rationalise any of this. The media available on television or movies always portrayed transfolk as caricatures, perverted villians, or oddities to be gawked at. Talking to parents was obviously out of the question as well, since they were the ones who taught us the gender stereotypes in the first place. For those brought up in Christian or Muslim households where homosexuality and crossdressing is explicitly taught to be a sin, bringing up our "deviant" ways is out of the question; it might cause us to be scolded, beaten or thrown out of the house. Also, boys are supposed to be strong and they don't share their problems do they? They just grit their teeth, shove their feelings deep down and push on ahead (only for it to manifest as a kraken-sized monster that probably needs years of therapy to properly resolve). Because all this starts at such a young age, we build up decades worth of fear and shame. 

*(Bapok and Ah-gua are terms from the Malay and Hokkien language used locally to describe tranwomen. They tend to be used in a derogatory manner)


The fear of being labelled as gay is also tremendous for guys. It is somehow wrong to be gay, so any whiff from actions or words that might suggest one is such, is treated with incredible aversion. This can be being too close in proximity with another guy, taking too much care of your appearance, or even hesitating when being asked if you are gay. I thought this was hilariously captured in this short interaction between a stand-up comedian and his audience.


In Singapore, it is a running gag before enlistment and during basic military training (BMT) that you should not drop the bar soap in the toilet since the showers cubicles are without doors, lest you get boned in the butt by a horny homosexual hungry for sex. (This last bit is never explained, just left to be inferred after some immature chuckling by guys). In such an environment where being gay is met with derision, it is no wonder all guys who proclaim to be straight are immediately defensive of their sexuality.

You might wonder why am I bringing up the fear of being labelled as gay in a blog about crossdressing. In my view, shame of crossdressing is sometimes tied very closely with the shame of being gay, given how gender and sexuality are frequently confused with each other. Sexual shame is real. For a lot of us, I think we are terrified of being gay. For example, if I like wearing women's clothes and being a girl, does that make me gay? Does it mean i should like men? If I watch porn and I identify strongly with the actress, am I gay? If I am curious about butt play, does that mean I am gay? No, oh god no, I cannot be gay. Not only am I a pervert who inexplicably likes to wear women's clothes, I'm gay too? That is too much to deal with. It's like a double sin in Asian society or religious circles.

Shame is a huge issue faced by us guys who have a penchant for wearing women's clothes. We constantly ask ourselves, why does wearing something as simple as a pair of black stockings and a tight skirt feel so right, so good, so arousing? Why do our fingers tremble and hearts pound with excitement as we roll the hoisery up our legs and zip ourselves into a body-hugging dress? If it is so wrong, why do we love it so goddamn much? Why are we so deviant and perverted? The shame we feel is a significant hurdle that holds us back in our exploration to better understand our female selves. It delays our decision to come out to others, to experiment, to transition (if we want to). It is shame and fear that leads to over-compensation in the form of misogynistic, aggressive behaviour. It is this shame that creates immense guilt when we crossdress, leading to purging, self-loathing and depression. 

I have a fair amount of public interaction as Isabelle to date and I have made significant progress in being confident as her. Yet it is strange that i feel some manner of fear when people stare at me in public. When others walk past me I still look away, hoping not to see their quizzical gaze attempting to figure out if I am a guy under the makeup, wig and dress. Walking into the makeup aisle at Watsons (a local pharmacy brand) in guy mode still makes me embarrassed, especially if there is a sales person nearby. Somehow I have the irrational worry that I will be identified as a man in a dress. Even at home, despite my wife's acceptance of my alter-ego, I still feel very awkward dressing in front of her, especially when my outfit is too sexy or over the top feminine. It is as though I should be the proper guy she married, not a tart sashaying around the house in stilettos and a bodycon mini-dress. The emotion I think here, is shame. I admit that while a large part of this shame is from years of repression, it is also self-inflicted, since I am not being ridiculed by passersby, outed by sales assistants or judged by the wife. 

I decided to write this post because, while there are bold ones who don't feel this shame and are unabashed in pursuit of their personal happiness, I think many of us have experienced shame in our journey through life, to varying degrees. For those who have overcome it and are fully secure in your masculinity, I am truly happy for you. For those who still experience it like myself, there is a need to continue to work on rationalising and overcoming the shame, to achieve that inner equilibrium. It will take time and effort, but I believe it is all worth it. 

To end off this post, here's an entertaining and introspective video by Contrapoints about the topic of Shame. She explains the shame she felt, after dating a really great and good-looking guy post-transition, only to realise that she was actually a lesbian transwoman. She could only see herself in a long term relationship with a woman. Strange isn't it? That after overcoming years of shame and the social stigma of transitioning, she suddenly finds herself faced with the the greater shame of failing to be a model transwoman; i.e. one who likes men. As always, Contrapoints shares interesting perspectives with her own entertaining brand of dark humour, so do set aside some time to watch the video.

 
(Clarke Quay on the Halloween weekend can be pretty fun)

Crossdressers who are still in the closet usually tell me that although they want to go out in public, they are very afraid of doing so. I fully understand how incredibly scary taking the first step out in public can be. I was once in your shoes, overwhelmed with fear and constantly worrying that people will recognise that I am a guy (I blogged about my first time). Fast forward 3 years and after massive improvements in my hair, makeup and dress sense, people on the street still easily recognise that I am a crossdresser. But my anxiety is no longer a blaring siren in my ears nor does it paralyse me. It is still there for sure, but it is now just a niggling thought that I largely ignore. We are lucky that Singapore is a safe place to crossdress. The primary hurdle we need to overcome is the irrational fear that exists all in the brain. So fellow sister who is still in the closet. Assuming you have mustered the courage to finally take the plunge, here are some suggestions on where to go. (While some crossdressers do go to HDB carparks in the middle of the night, I'm not going to suggest it. You're unlikely to see anyone there, but it is a horrible first time location. What are you going to do? Walk up and down the carpark ramp in your stilettos while you melt in your wig?)


1. LGBT friendly bars. Or Clarke Quay on Halloween
This is an awesome starting ground. Although getting to the bar itself might be a bit more challenging, once you're in the venue you can really relax a bit and be yourself. My first time out in public was to an LGBT friendly bar on the Halloween weekend. Even though I was sort of dragged out there and was so scared I was barely conversational, it did feel like a safe space, especially after the drag queens turned up. Although you are unlikely to meet other crossdressers (the community is tiny), a friendly transwoman or drag queen might decide to chit chat and give you a bit of encouragement.

If you're feeling a bit more daring, you could head to Clarke Quay. Try to aim for the Halloween weekend, since it is an excuse to dress up and be a bit sexier. Do remember to practice walking in your killer heels at home and bring out some plasters, or you'll be holding your heels and walking barefooted before the night is over.


2. Shopping malls 
As scary as going out in bright daylight sounds, shopping malls are pretty ok places to crossdress. Most people are there on errands and will mind their own business. If you want to be a bit tactical, pick a large mall with big name brands (e.g. H&M, Zara) and go there on weekdays when the shops open (typically 10am or 11am, depending on the shop). There's barely a crowd because most people are working or in school, and sales assistant really don't care about whether you are LGBT or not. Boutique shops can be a bit more unnerving since it is smaller and the sales assistants might follow you around, but remind yourself that they are just being friendly.  


3. Selfie studio
Selfie studios are kind of a new thing in Singapore. While this is a confined space that isn't exactly a "public" location, you will still need to interact with the owners of the place and possibly give a shy smile to other customers you see there. The good thing is that the owners usually don't care whether you are male, female or transgender as long as you are a respectful, paying customer, and anyone you see there wouldn't bat an eyelid about your crossdressing, since they'll likely be in costume too. Note that selfie studios usually charge by the hour. 


4. Join an LGBTQ event in a public space
This might be scary, but it may just be the fastest way to make friends (I recently saw a Trivia night organised by the Katong Queers that looks really fun). I've also heard of group meet ups in the LGBTQ community for BBQ, board games and other very casual, non-bar/clubbing events. While I haven't joined any, with the LGBTQ community opening up more and more in Singapore, I think this could be a good starting point. 


5. Cosplay event 
I feel that cosplay is akin to a gateway drug for crossdressers going out in public. While I personally haven't gone to any events, quite a number of local crossdressers start off here. It can be a bit scary for a first timer, but with everyone just dressed up as their favourite anime character and having fun taking photos, it is a pretty safe starting point. Taobao has also significantly lowered the barriers of entry to cosplay since you can just buy off the shelf costumes. Might need a bit more courage than say....a carpark in the middle of the night. But you know, carpe diem right? 


6. Parks / Marina Promenade
I'd say, this barely made the list. Personally I don't like going out to non-air conditioned places because in Singapore's weather, wearing a long wig makes you sweat buckets, which then makes your makeup run. But going out at night is a lot more cooling so it could still be pleasant. The Marina Promenade area, including the area in front of MBS is a pretty place to walk around at night with its lights and cityscape, without being overly crowded. So that's a decent option.


7. Museums / Art Galleries
This wasn't in my original list but someone suggested it after reading a crossdressing reddit thread...and yes, it IS a great place to go. They're air-conditioned, generally empty, they're big so there's many areas to wander around. And the main ones in Singapore are really great places for taking photos (so many people go there to take their wedding photographs). So you could consider wandering around in a museum or art gallery.

While picking a place is important, the journey to your destination will be your first brush with other people. If you don't drive, public transportation can be a bit daunting for a first timer since you'll be in a confined metal vehicle with strangers for a duration. One way to avoid talking is to book a private hire vehicle using an App, so the ride is paid for and you don't need to tell the driver uncle in your deep baritone where you want to go. 

Another key tip is something I've mentioned this before and will repeat ad nauseam. For your first time out, please please do not wear your 5 inch stilettos, paired with a mini skirt and pantyhose. And don't overstuff your bras (deduct 1 or 2 cup size from what you think you should wear). While it might be a massive turn on for you, you'll stand out like crazy, which will make you even more nervous. Unless you've got an exhibitionist streak and enjoy people staring at you (yes, there are some who enjoy the attention), do try to dress a bit more simply.

Alright! So hopefully this post gave you some ideas on where to go for your first trip out in public. If you are still deep in the closet and still on the fence, make plans for it! Don't be like me and step out only when you're starting to get wrinkly. The younger you venture out, the more you can explore and have all the fun that crossdressing has got to offer.
I chanced upon this gem of an interview shared in the sgbutterfly facebook group by the admin. I watched a bit of it without too much expectations and ended up making it through the whopping 3 hours long interview (broken into 3 separate episodes based on the themes and because it was too long). Kudos to the host for asking many interesting questions and for Aerie to share her story, along with giving well-balanced and thoughtful answers about many topics that transwomen and crossdressers face. Even though it was a long interview Aerie was pleasant and even slightly positive sounding, which was easy on the ears for sharing what could have very well been a heavy topic.

Aerie Rei is quite an interesting character, with a growing up story that I think many crossdressers and baby-transwomen can relate with, and a bit more. She came from a staunchly Christian family, spent 10 years in an all boy-school, started being drawn to everything female in Primary school, went through the phase of over-compensating by embracing toxic masculinity before snapping out of it, went to army, university, had a few girlfriends, worked in the Government, came out to her friends, colleagues and her parents, got kicked out of the house by her dad. She started her transition in 2020, at some point chose to be a porn star because it is something she loves doing and even flew to America for her first professional porn shoot. She was also fortunate enough to find love and married a Transman in Singapore (they have a polyamorous relationship). 

You could say, she had the typical middle income Singapore guy experiences and life trajectory before doing a major direction change. 

I think the interview is well worth the watch, especially if you're starting out or in the middle of your journey. If you've got no time, you can skip along to the parts that you are interested in. The host conveniently put a whole bunch of chapter links for each of his questions. 

Part 1 of the Youtube video is embedded below, while Part 2 and Part 3 are linked. Do have a watch! Alternatively you can also hear it as a podcast.



In the daily grind, the brain regularly wonders how to get more sources of income. Other than buying the occasional lottery ticket and hoping for a moonshot, a common advice flung around ad nauseum is to monetise your hobby. There's good reasons for this advice. After all, if you love to do something and it is supposedly your "passion", isn't it great if you could make money from it at the same time? Then your job will no longer be a job. 

Of course things are a lot more complicated than that. If everyone could simply convert their hobbies into their regular and constant stream of income, we'll be seeing people do it left right and center. Not all hobbies have money generating potential, let alone be something that can earn you more than what the day job provides. Most will require a significantly high level of skill in order to generate decent returns (e.g. just because I enjoy football does not make me an English Premiere League level player).

It could be considered a bit sad, but when I am asked what is my hobby, I usually struggle to answer the question. I wouldn't consider crossdressing a hobby per say (it is a part of me), but I obsess about it a fair bit, I don't tire from doing it repeatedly and derive a lot of joy in doing it, which kind of makes it sound like a hobby. I've been asked more than once about monetising it, but I knew the the pressure to generate sellable products/services/content would lessen the enjoyment I derive from crossdressing. The only idea that I more seriously considered was monetising this blog via advertisements. Unfortunately after a 2 month wait following my application with Google Ads, Google decided my blog was of low quality content without bothering to provide any explanation why it was classified as such 😑. But oh well, it was worth the shot.

So if I really wanted to monetise my crossdressing "hobby", what were the possible avenues I could take it?

Storage service
Providing a storage service is a feasible business, although one that has very limited growth potential, since the local crossdressing community is really small. The amount of money one can potentially get from leasing out a room is also limited by the amount of free space one has. In addition, people renting my space would know where I live, which is something I couldn't come to terms with. There's probably better storage options out there.


Makeup / dress-up service
If I significantly improved my makeup skills, this could be a potential side business, although I'd likely have to undercut a lot of the existing makeup artists out there. It is an immensely competitive industry with low barriers to entry, and anyone with a bit of patience and willingness to pick up makeup won't want to seek out a makeup artist unless they're planning for a special shoot. When they do plan for a special photo-taking session, they'll want someone really skilled. There are amateur crossdressers who would be willing to meet a fellow crossdresser, and learn how to elevate their makeup skills in a safe space, but they also tend to be younger with lesser disposable income. Younger crossdressers are also a lot more daring nowadays, willing to come out to friends who could teach them makeup and provide the safe space to dress up, meaning that there isn't a strong need to engage special services to teach them how to transform into a woman.


Youtube / streaming
Youtube and streaming platforms like Twitch, Bigo, etc, are probably a feasible source of side income. The internet allows the potential to reach a huge global audience beyond Singapore. With consistent, quality content pushed out regularly, it is possible to The scene is however, immensely crowded with everyone essentially shouting for attention (figuratively speaking). Another downside would be the need to put myself in the public domain, where everyone can see and hear me. With enough videos/streams out there, I think it wouldn't be too difficult to put two and two together to figure out who my male self is. Maybe at some point when I'm ready to come out I could do it. Or maybe not. I think my transformation from the male self to Isabelle is quite drastic, so it could make for a couple of interesting videos, but that is probably about it.


Patreon / Kofi / OnlyFans
Patreon and Kofi are possible platforms if I ever decide to go down the route of cosplaying, taking superb photos and effectively selling them on an online platform. I've improved in my photography and posing skills quite a lot, but to do it as a professional cosplayer feels like next level stuff. Anyway I don't think I'm pretty enough to have hordes of fans wanting to buy my photos. 

As for selling NSFW photos/videos via OnlyFans, well this is something I'd never do (it is also illegal in Singapore if there is nudity, per the Titus Low case). But it seems to be a popular option among many many crossdressers to either fund their hobby or to *ahem* release their inner wild woman. I think crossdressing is a sexually charged activity for many in the community and wanting to monetise this is a win-win option in a sense. But whatever is uploaded onto the internet stays there forever, so got to be careful when one decides to supplement income via OnlyFans.
(So many long sexy legs in this OnlyFans photo 😆)

I'm sure there are more creative ways out there to make money from crossdressing beyond what I listed down above. There are many super successful folk out there (beauty bloggers who sell cosmetics especially), but the market for crossdressing services remain generally small and niche. Maybe if you do think of something interesting, add it in the comments so I can expand this article!


Although this seems to be an easy question to answer, I do get asked more frequently that I expected. They're mainly asked by those in the closet, although some who have a bit more experience dressing up do ask me occasionally as well. 

There are some dedicated clothing shops for crossdressers online, originating in the USA or United Kingdom. However, I do find that these shops seem to be a product of an older era, when it was much hard to buy items online and anonymous delivery or self-collect from delivery lockers (e.g. POPStations, Ninja Collect, Blu, etc) was not an option. Marketed towards crossdressers, the range of available styles are narrower and tend to be a lot pricier for equivalent items sold in regular brick and mortar shops for women. Nevertheless, they do have certain specalised products which can be very good (e.g. high quality silicone hippads), niche outfits that appeal to certain segments of the community (e.g. 100% satin or latex maid outfits, super frilly petticoats, ballet stilettos) or outfits for crossdressers with very large and masculine physiques. For regular day to day clothing however, you're better off buying from the large number of options that women have. I've tried to list down the various choices available to crossdressers and why you may want to go for them.


1. Easy to walk around  -  Big clothing chains
For crossdressers who have started to step out in public, big clothing chains such as Zara, Mango, Cotton On, H&M, Uniqlo, etc, are fantastic to shop at. The selection is massive, there are frequent discounts and the clothes are regularly refreshed so you can come back in a few months to whole new range (yes, fast fashion isn't great for the environment I know). One of the best parts is that sales assistants generally don't both you, and because of the large floor area you can do your shopping without bumping into other patrons. Not that it really matters too much, since the ladies in such shops are usually absorbed in picking out clothes, while the men are just wandering around in boredom or scrolling through their phones. 

Unfortunately, if you're still in the closet, you may need to purchase clothes without being able to try them, which is a real bummer as the clothes may not fit well. Return policies are quite liberal, but that means walking up to the counter staff again in guy mode to ask for your slinky sequin dress to be exchanged for a larger size. Very nerve wracking for the newbie crossdresser.


2. Personalised service  -  Small brick and mortar shops
I haven't gone into such small shops because I still feel nervous about interacting with sales assistants using my guy voice as Isabelle, and I know I will feel obliged to at least buy something if the sales assistant is super friendly and accommodating. To save my wallet, I've largely avoided such small shops. But I know crossdressers who have done so and they find the experience great. You'll get the full attention of the sales assistant who is eager to help you out and let you try on the clothes, in order to close a deal. I think sales assistants are also usually bored out of their minds.

Just because shops are smaller does not mean that you will not be able to find clothes that you like. The benefit of smaller shops are that the clothes could potentially be cheaper, negotiation is possible and they may hold certain range of clothing not typically found in the big clothing chains (e.g. Taiwanese styles, Evening/bridal wear, some can tailor make outfits if you're willing to pay for it, etc). 


3. Free returns  -  Zalora, Asos
Oh free returns are really the best when it comes to online shopping. Zalora and Asos were such important platforms that helped me to try on a wide range of outfits when I was still in the closet and unable to shop in person. I was able to order a larger selection of clothes and only keep the outfits that looked good on me, which helped to keep my crossdressing expenditure down. They helped me to gradually figure out the types of outfits that worked for my body shape and allowed me to explore styles that I would normally have not picked as a 1st or 2nd choice. In addition, the selection from these shops are massive and sells everything a girl needs; you can buy dresses, tops, skirts, pants, undergarments, sleepwear, accessories, makeup, brushes, bags, etc from either sites. Currently, around 80% of Isabelle's wardrobe is purchased from Zalora and Asos, which is pretty significant. Zalora has amazing delivery speeds locally; there were days that I got the package the next day even though I didn't sign up for next day deliveries. Buying from Asos will mean you get your goodies a bit longer, as they need to be shipped from overseas. Asos also tends to be more expensive than Zalora, although the quality and range of their clothes can be even larger (e.g. I could never find proper sequin dresses on Zalora, but Asos has loads of them).

Besides free returns, the next best thing is that you can deliver and return your parcels all via POPStations, which means you can make your purchases without worrying that your mother might "accidentally" discover her son buying women's clothing. Neither Zalora or Asos state the contents on the outside of the package, meaning that you can choose to deliver to your house without too much worry. 

Zalora did change it's free returns policy in 2021 to a conditional free returns policy of minimum $50 purchase however, probably due to the large number of people abusing the free delivery and returns policy. To make sure I qualify for free returns, I usually make a massive order from Zalora (like 15 outfits) and throw in some guy clothes I actually need for good measure. This way, all it takes is for me to keep 2 outfits to cross the $50 threshold. 


4. Local online shops  -  Carrislabelle, MGPlabel, Topazette, etc
I don't really buy from such shops as they usually charge a delivery fee for smaller orders and do not have free returns (yes, I go for value and buying something that doesn't fit properly or look good irks me significantly). However, the upside of local online shops is that they tend to fit the asian physique better (read: short). They could also be of decent value, as local shops tend to sell clothes in the price range of $30 - $50 for something that feels a bit better quality than some outfits sold in Zara (this depends on the brand too of course). I consider Love, Bonito to be in this category as they used to be an online only shop, though they have recently expanded aggressively into major shopping malls. I absolutely adore Love, Bonito's clothes as the material is heftier and feels high quality. I have also bought a white mesh dress from Carrislabelle, which turned out to be one of my favourite outfits because of how well it fits and they way it hugs the body. It was also a lined dress with material that felt more premium than what I would have normally got at that price point. 

(This is the model, not me)

Point of caution though, unlike Zalora and Asos, such shops may have fancier packaging and sometimes state the contents of the package within them. If you currently live with your parents and the shop you want to buy from is unable to deliver them to a self-collection delivery locker, you may want to give the shop a miss. 


5. Anything you can think of  -  Taobao, Lazada, Shopee, Shien
Taobao, Lazada and Shopee really brings the world to your doorstep. Anything that you can think of, they sell. Especially so for Taobao. Lolita dresses, cosplays, wigs, accessories, props, wedding gowns, school girl outfits, cheongsams, maid outfits (long victorian, cosplay, or even skanky ones), are all sold on these platforms. Large sized Louboutin stiletto knock-offs? No problem.

There are a few downsides with using these platforms though. If you don't like an item or there are defects, returning such purchases can be a pain in the butt, especially for Taobao. Although some crossdressers like to buy dresses from Taobao, I find shopping on the platform tiring as cheaper shops have the bad habit of using photos nicked from other places, while more expensive shops with better quality clothes can end up being pricier that buying locally. As such, I only buy items from Taobao that I cannot get from local shops, such as wigs, cosplays, breastforms, clip-on earrings, unique lingerie and large sized high-heel shoes (Local shops only sell up to size 41, while I am a size 43). I generally treat my purchases from Taobao as disposable. 

Do take note that Lazada and Shopee has this bad habit of stating the contents of the package on the delivery label, which is very annoying if you live with your parents and are delivering to your home. Taobao does not have this problem. The other downside of using Taobao, Lazada and Shopee apps, especially if you do so on your guy mode phone, is that ads for items your browsed on these apps will bleed all over the place. I've seen cheongsams and wigs recommended to me when I was reading the news on my BBC app. Not great if trying to be discreet.

I added Shien to this category, as it feels like an English-language site for clothes sold on Taobao; massive range of clothes and budget friendly, but quality is a dice roll and the photo of models look like it was nicked from somewhere. I personally haven't bought any clothes from Shein, but I have heard a mix of good and bad feedback from other crossdressers. 

(Photo of $27 sequin maxi dress sold on Shein. Looks fantastic, but I have my doubts on the quality. The model looks so glam, it looks like it may have been from a prom dress shop selling $100+ dresses. On Asos this would be $60 or higher, especially if the dress was lined)


6. Online 2nd hand  -  Carousell
Buying 2nd hand is recommended for crossdressers, considering how infrequent we wear our female attire. Carousell is a one stop portal that allows us to search for and buy 2nd hand women's clothes easily on our mobile phones. If you're afraid to meet up with the seller in person and reveal that you are a guy, you could easily arrange for the item to be sent via mail for a couple of dollars. This makes shopping via this app a very feasible option for crossdressers still in the closet. 

I've done my fair share of browsing on Carousell and find quite a number of clothes from popular local clothing brands being sold. This means that if you're hankering for a particular outfit from a local clothing brand, there is a chance you'll find it on Carousell. The downside of course is that the seller may not have your size. In addition, I find that the listing price has a tendency of being only at a slight discount from the original price it was retailed at. Nevertheless, being a 2nd hand online shop, a good deal is bound to pop up every now and then.


7. Cheap 2nd hand  -  Refash
Refash is a decent option for buying clothing on the cheap if you don't mind wearing something second hand. Their selection is decent and the price is wallet friendly too, which is very important for us occasional girls. The downside of Refash however is that you have to shop in person and it is like trawling through the bargain bin; you don't know what you'll be getting and if you do see something you like, it is the only piece and there's a chance it might not fit. So go in with zero expectations and you might turn out to be lucky.


After a while, you'll come to realise that buying clothes isn't the difficult part for crossdressers. It's making the most of your money and spending them on items that fit you properly, rather than wasting money on outfits that don't look good. It is important to know your body type, measurements and styles that flatter your body, rather than outfits that look great on a svelte, doe-eyed model in her early 20s. Pretty girls can wear a gunny sack and still pull it off, so if you do buy clothes online, try to cover the model's face, or try to imagine whether the outfit will still look good if it were 1 to 3 sizes larger. Takes a bit of practice and wasting some money buying stuff that doesn't work, but you'll get there eventually. 


I don't have statistics to back me up, but based on conversation with other crossdressers in the community, revealing to your girlfriend or wife that you crossdress is akin to playing Russian Roulette with your relationship (except there are probably 5 bullet rounds in the chamber rather than 1). There's a chance that you'll come out unscathed, but the odds aren't very high. 

I've heard too many stories of regular(?) relationships that crossdressers have ending in divorce or breakups. Or if the relationship continues, there is simmering unhappiness and discontent on both sides; the guy will be feeling constrained and unable to freely dress up, needing to take various measures to do it behind the wife/girlfriend's back, causing the crossdressing behaviour to go deeper underground. While the girl will either be constantly wondering if her husband/boyfriend is crossdressing behind her back, or be worried that he might decide to transition all of a sudden to live as a woman full time, which is way more than she had bargained for.

Vivienne, a New Zealand based blogger who writes about crossdressing, documented on her blog how her marriage began its downwards death spiral three years after tying the knot, when she revealed to her wife about the crossdressing. It was quite a sobering reminder that even in a developed nation fairly accepting of LGBTQ members in the community, when things hit close to home, acceptance may not be as easy. 

I can fully understand the conundrum that wives and girlfriends have to face when their special other owns more high heels than they do and prefers wearing dresses and lacy lingerie over regular men's wear. Their entire mental model of how their partner should be is thrown out of the window in an instant. Flip it around and it's easy to appreciate how challenging it is for wives and girlfriends to accept crossdressing. Imagine one day during dinner, your wife/girlfriend tells you that she prefers to bind her breasts, wear boxer shorts to bed and shave her beautiful long hair into a crew cut because it makes her feel whole when she dresses like a man. How many husbands and boyfriends will balk at such a revelation? Of course, women wearing men's clothes in society is more easily accepted than men in dresses, but if you turn the masculinity dial up a few notches (like the scenario I described), it requires a big shift in the guy's mental model of how his spouse should look and behave. 

The "woke" community can argue to say that gender is not as binary as society has led us to believe, people should recognise this fact and be more accepting if their partners want to dress in a certain way. They are right that there should be greater acceptance. But the harsh reality is that society is very clearly split into two genders; Male and Female. We have been raised for years to identify certain traits as male and female, boy and girl (even my kid at 18 months old could easily point out whether someone was an "Uncle" or "Auntie"). It is going to take a good number of decades before gender fluidity can truly be accepted in mainstream society....if it is ever going to be at all. Even as a member of the LGBTQ community, I struggle to get my head around the bearded lady or guy in a dress aesthetic that some in the community go for (e.g. Billy Porter, Conchita Wurst); let alone someone who is less immersed in the concept of gender fluidity. 

Not all crossdressers' marriages end in tragedy of course (although I believe they still remain the minority). Apart from myself, I know crossdressers whose wives accepts their husband's crossdressing. For a lucky few, their wives even partake and enjoy the crossdressing behaviour. Usually for such cases, the secret is revealed prior to marriage, meaning that it was a conscious decision by the wife to decide to marry the guy despite knowing his feminine inclinations. 

For younger crossdressers who have yet to commit to a relationship, it is a good rule of thumb to be upfront about your crossdressing inclinations from the start (perhaps on date 3 or 5?). It is heart-wrenching to see a potential partner do a 180 degree after you do your big reveal, but think about how much more painful it is when you have committed years into a relationship and have marriage looming ahead. Or worse, you have a house and kids, but are suffocating inside because you are unable to let your female self loose once in a while (trust me, once you move in together with your wife, the "oppressiveness" and latent stress you feel from the need to constantly hide is no joke.). Although society isn't 100% ready for gender fluidity, each generation is becoming more accepting and open. So be just a bit braver while you have youth on your side.  


Fetish: a form of sexual desire in which gratification is linked to an abnormal degree to a particular object, item of clothing, part of the body, etc.

Based on the definition provided by Google, I don't think it's too far off the mark to say that yes, crossdressing is a fetish for many in the community, whether they like to admit it or not. For many, wearing pieces of female clothing usually results in sexual arousal. I'll be lying if I said that dressing up in female attire doesn't get my engine revving as well. It is also one of the reasons why I think the urge to crossdress increases exponentially after the onset of puberty, when sexual desires emerge due to the new chemical cocktails swirling in the body. The desire to "get off" while crossdressed starts around that age too. 

I'm not saying that crossdressing is a fetish for everyone in the community. There are many reasons why one decides to crossdress and not all of them have their roots in deriving sexual pleasure. Some do it because it is fun, some do it to to feel whole and complete, etc. Our motivations to crossdress may also change as we grow older and more experienced as well; it could start off as a sexually stimulating activity, but the fires mellow over time and one crossdresses because it is a relaxing, fun activity to do. Shopping as a girl is undeniably more enjoyable by MILES compared to shopping as a guy. 

For crossdressers, it is important to realise that there is nothing wrong to feel turned on by wearing women's clothes (there is sometimes a lot of post-dress-up / post-release guilt involved). Just because something is a fetish does not mean that it is a perversion. These two words have a tendency to be confused together. As humans, we all have our different personal tastes and kinks. For a more mainstream example, guys like it when ladies with long legs show off their figure in short, tight bodycon dresses and high heels. Isn't that a fetish too? But it is never considered a perversion to have this preference (unless you're living in a super conservative part of the world, which in Singapore, we are not).

Perhaps in the definition above, "abnormal degree" is the part that we crossdressers need to be conscious of. It differentiates a healthy kink from an addiction that consumes your everyday thoughts, to the point of affecting your ability to function properly day to day as another member of society. 

There's nothing wrong if crossdressing turns you on. But always remember, everything in moderation 😉

Having chatted with multiple crossdressers in the past few years, I observe many parallels in their stories. Despite different backgrounds, ethnicities, nationality and upbringing, the majority of male crossdressers seem to have a similar starting point and go through the same phases. Age does not dictate which phase one is in, but it does have a big influence on whether one moves on to the next phase or not, due to financial independence, personal independence, or just an increasing sense of YOLO.

(Disclaimer: the following phases isn't based on research, but my opinions based on observations)


1) Initial Realisation
The first phase usually starts off young, around 7 to 12 years of age. Just like a switch is turned on, inexplicably strong feelings of desire and curiosity of hoisery, skirts, dresses and other feminine garments manifests itself. There's also a lot of confusion at this phase, since the newfound desires run contrary to society's programming of behaviour expected of males and females. Strangely, this phase seems to happens just before the onset of puberty and the awakening of sexual desire, which many of us find so intertwined with ladies' clothing.

For a minority, the realisation phase happens in the late teens / early 20s, usually triggered after a single crossdressing event (during halloween, due to a dare, etc), which helped to provide the first taste of how nice ladies clothes feel.


2) Closeted - Borrowing clothes
This second phase occurs almost in quick succession after the discovery phase. Because the crossdresser is usually a young child or teenager living with his parents, the only access to ladies' clothes will be those of his mother, sister or relative. Being in school also means very little spare funds to purchase his own clothes and wig, let alone makeup, lingerie and heels. However, because the crossdresser is so early in his journey, it doesn't take much to fulfil his desires to look like a woman. Just slipping on a silky chemise, a tight pencil skirt or feeling the tight constrains of a bra that's usually too small for his male chest is enough to get his motor going. The mind and imagination usually fills in the gaps that makes the crossdresser feel incredibly pretty. 

At this early phase of his crossdressing journey, it can be a very confusing period. He knows that crossdressing isn't normal, perhaps even wrong as society has ingrained in him. Men and boys shouldn't be wanting to wear dresses and wanting to feel....pretty. Yet strangely it feels so damn good and he cannot help himself. When there is a window of opportunity for him to crossdress coming up, he will obsess in the lead up to it. Usually, there is a constantly recurring feeling of guilt, as he struggles between his personal wants and what he thinks society requires.


3) Closeted - Owning clothes / tried makeup
Unless there's a fashionista in the house, borrowing clothes from either mum or an elder sister gets old really quickly. Mum's tend to have a more mature style, while sisters probably have a smaller frame and thus harder to fit once puberty hits. I remember not liking ANY of my mum's clothes, and not being able to properly zip up my sister's dresses (except the stretchy ones). Also, borrowing clothes raises the risk of being found out, in case of accidental ripping of favourite outfits, forgetting to put them back to the exact location, or *ahem* having accidental biological release due to extreme excitement. Mothers are especially attuned to things that are out of place. So it is only a matter of time before crossdresser move to phase 3 - owning a feminine wardrobe. After all, you cannot keep trying on your sister/mother's favourite outfits or lingerie. 

Nowadays, online shopping and delivery to pick up stations makes it very much easier to buy clothes and pick them up without even needing to speak to any person. All you need is a debit or credit card. Once a crossdresser has his own outfits, he will also take the effort to purchase essential accessories to complement his feminine look, such as wigs, breastforms, high heel shoes, hoisery, etc.

Crossdressers also begin dabbling in makeup after a while, as it is the next essential piece in trying to look pretty and convincingly female. It is potentially challenging though, as makeup is time consuming to apply and remove. Given that most Singaporeans live with their parents until they are married, they almost never have a truly private space to try on makeup at home. One can easily swap from female to male attire very quickly, but to remove a full face of makeup cleanly will take a lot longer. As such, being good in makeup can sometimes take a while.

I find that phase 3 usually lasts very long, because the mental hurdle that needs to be overcome in order to step out in public as a girl is very high. For some crossdressers, the fear holds them back and they never gets to phase 4 and 5, instead skipping on to the normalisation phase (phase 6). Some slightly more daring crossdressers do come out to their wife/girlfriend/friends, but they still do not go out in public as a woman. For these, they are also considered to be in phase 3.


4) First Time Out
Going out in public for the first time is very scary, but incredibly exhilarating. The chemical cocktail due to the fear of being discovered, guilt of doing the taboo, and desire to go out as a female, is a powerful, heady mixture. I still remember vividly the first time I stepped out in public how I could feel the thumping of my heart in my ears.  

For many in Singapore, the first step out in public seems to often be in the dead of night when the risk of being seen by others is very low. Another common venue for a first time out would be to one of the LGBT clubs in Singapore, either alone or egged on by other more experienced sisters. For those who are bolder, it could be a trip to the park or shopping mall in the day, the latter being based on the logic that it's easier to blend in with so many people walking around, since people are mostly too busy (read: self-absorbed) doing their own things that they don't really bother paying attention to others. Going out in public for the first time usually marks the crossing of the threshold into a new phase of discovery of the crossdresser's journey. 


5) Discovery
With going out in public as a woman no longer in the realm of fantasy, the flood gates are now wide open, showing a whole range of possibilities and new activities to try out. There's will be many firsts from here on out, such as shopping in girl mode for the first time, dining in a restaurant for the first time, taking that selfie in the ladies toilet for the first time, watching a movie as your feminine self for the first time, being addressed as "miss" for the first time, spending a few days in girl mode whilst overseas...the list goes on. 

For the sexually adventurous, it could be the discovery of new sexual preferences, through meeting like-minded people in the community or just due to a greater willingness to reach out and try. Perhaps one also discovers how incredible sex may feel when you are dressed as a woman, be it with your girlfriend, wife, other crossdressers or even men.

Personally, I think this discovery phase is the best phase of crossdressing. The simplest activities that we take for granted in male mode are now wonderous and exciting as a female. Although some of the experiences are viewed through rose-tinted glasses (e.g. thinking that every outfit looks extra pretty when trying out clothes in the fitting room for the first time), because everything is new and exciting, these make for great memories that we will reminisce when we are further along in our crossdressing journey.

The younger one reaches the discovery stage the better, as crossdressing is more fun with youth on your side. Also, discovering your own sexual orientation and whether you plan to transition early is helpful in avoiding future regrets in life. Based on personal observation, crossdressers do seem to be reaching this phase earlier, due to the proliferation of smartphones, online shopping and access to easily available information about crossdressing via the internet.


6) Normalisation / Plateau
After having tried most of the common activities that crossdressers tend to do, one reaches a normalisation phase. It's frequently described as a "been there, done that" phase, where the novelty of crossdressing has waned. This is just like any hobby / activity really. Take for example travelling. Your first few holidays overseas would be incredibly exciting, but after your 50th holiday, cities and natural sceneries start to look the same. It takes a really epic destination or unique activity to get you excited again.

Similarly, crossdressing can still be exciting, but it takes a really pretty outfit or a new, novel activity to trigger the same desire that one used to feel in the discovery phase. When all it took in the past was sliding on a pair of stockings up one's legs to get the motor revving, it now requires dehairing, a full-faced makeup, immaculate hairdo, a perfectly coordinated outfit with matching lingerie, and perhaps an annual themed crossdresser gathering to get one equally excited again. 

Frequency of crossdressing usually drops in this phase, due to the reduced interest in crossdressing, or that it simply takes a lot of effort. If the excitement derived isn't consummerate with the effort put in, why would you do so? A common reply to invitations to dress up might be "I'm too lazy to dress", when the you 5 years ago would have pounced on the same opportunity in a heartbeat.


7a) Retirement
Sadly, the fires of excitement that burned so brightly in the past will fade away with time, either due to age, fatigue from crossdressing or a lack of novelty. Once everything in his crossdressing to-do-list has been checked off multiple times, he may decide to hang up his stilettos, little black dresses and retire for good. 

Another type of retirement that is commonly observed is early retirement (usually after a bout of purging), brought about by personal reasons (birth of a child, wife demands swearing off crossdressing for good, etc), or guilt of living a double life and not being a "proper" man. However early retirement tends to be temporary, with the hiatus lasting from a few months to a several years, until a trigger event happens that plunges the crossdresser back into the thick of his feminine ways.


7b) Full time girl mode / Transition
For some crossdressers however, dressing as a woman reaches an inflection point; he realises that his gender dysphoria is so strong that the infrequent crossdressing isn't sufficient to meet his personal needs. He is transgender and wants to spend his time living as a woman permanently. Whether he undergoes hormone replacement therapy, feminisation surgery or SRS, this threshold is the largest one to cross, as he isn't a crossdresser anymore; she's now a woman. It is very challenging, as it requires her secret to be made known to relatives, friends and society. But despite its challenges, there are success stories of crossdressers who eventually live full time as women. 


Conclusion
For readers who have been following my blog posts and reading about my crossdressing journey, you probably can point out easily that I am currently in phase 6: normalisation. Crossdressing is still exciting, especially if I get to try a new outfit that I have been pining for the longest time that makes me look extra pretty. 

So dear reader, which phase of crossdressing are you at? Do you agree with my observations and rough mapping out of phases which mtf crossdressers go through? Do let me know if there are phases or key details I may have missed out, so that I can expand this article.

Short answer: No, wanting to crossdress doesn't mean that you are gay. But you could be (and that is independent of your love for crossdressing).

I presume the definition of "gay" here is being sexually attracted to other men.  There is quite a fair bit of fear among crossdressers that deep down, they are gay. This is likely due to how we have been brought up in society to shun that which is deemed not "normal". 

For most of the crossdressers that I know, they generally view themselves as straight. They find no sexual attraction to the male form, and are turned on by women. However, the confusion arises when the crossdresser is attracted only to women when wearing men's clothes, but when crossdressed, he has adopted his female persona and is willing to participate / turned on by sexual activities with other men. Or perhaps the crossdresser finds other crossdressers a turn on, regardless of the genitalia (sometimes especially because of genitalia). Throw into the mix the recurring question of whether to transition or not, and you've got yourself a really confusing state of affairs. 

I wrote a short post about the difference between "Gender Identity" and "Sexual Orientation", which are usually mixed up, and for good reason. These are non-binary, resulting in so many permutations (a sample list shown below). Our emotions and how society expects us to behave also tends to cloud our evaluation and cause us to conflate the two. 
  • Male ❤ Female = Heterosexual
  • Male ❤ Male = Gay
  • Crossdressed Male ❤ Female = Heterosexual? Or Lesbian?
  • Crossdressed Male ❤ Male = Gay? Or Heterosexual?
  • Crossdressed Male ❤ Crossdressed Male = Gay? Lesbian? Or Heterosexual?
  • Crossdressed Male ❤ Transwoman* = Heterosexual? 
(*To make it clear. Transwomen ARE women.)

My personal take is that you are likely to be bisexual if you are normally attracted to women, but are also willing to participate in sexual activities with men when crossdressed. Regardless, you shouldn't beat yourself up internally if you swing that way. Sexual tastes and preferences, as long as they aren't harmful to other people, should be more accepted (barring the truly bizarre ones...like *ahem* necrophilia). The good news about living in Singapore in this day and age, is that we can freely participate with members of the same sex  (I won't go into the whole issue about gay sex being illegal in Singapore, due to a very archaic law from the colonial days that has yet to be repealed. That subject is very incendiary and there's a whole range of polarising views on the matter).

I'm not an expert on the topic, so do take what I write here with a pinch of salt. There are articles on this question which you can find on google, such as here and here. Reading more might give you a bit more clarity on the matter. I do find that this site called the Genderbread Person on the differences between "Gender Identity" and "Sexual Orientation" is much more illustrative and may help you pinpoint where you call on the spectrum for sexual orientation.
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