Musings of a Singaporean Crossdresser

(Me when I see that beautiful evening gown)

Crossdressing is such an expensive hobby. 

I can imagine some of you girls are already nodding in agreement. The amount of money spent on kitting out the female wardrobe and trying to look convincingly female adds up to a surprisingly substantial amount.

Some of you may argue that, no, crossdressing can be done on a budget. All you need are a dress, a wig from Taobao, undergarments from Cotton-On, stuff the bra cups with socks, a pair of simple flats and Voila! Guy to Girl in under $60. Well, that does count, but how long before another pretty dress or gorgeous pair of high heels captures your attention? And you'll need a daily outfit, a formal outfit, an OL outfit (or maybe 3 🤣), etc. The costs add up! Not to mention, guys need additional paraphernalia to properly achieve a more feminine look.

Of course, you may also argue that there are even more expensive hobbies out there (e.g. vehicle modification and detailing, skiing, skydiving, collecting luxury handbag, raising a child 🤣), but for an activity that is done so infrequently, crossdressing ain't cheap! 

Let's do a very rough breakdown of money I have spent over the years to feed the woman inside:

Clothes = $4500 (too many to properly count. I may have underestimated)

Lingerie = $400 (I'm guilty for having way too many lingerie sets)

Wigs = $600 (I've 15 cheap Taobao ones, and 1 expensive Girl Hairdo one)

Makeup = $400 (drugstore. Includes brushes)

Shoes = $500 (8 heels, 5 flats)

Breastforms = $250 (4 forms, 1 breastplate)

Padding = $350 (1 taobao pads, 1 dresstech hips)

Accessories = $150 

Photoshoot = $938 (did 1 in japan. Results were meh. And a bridal shoot in Singapore)

I'd say my expenditures might be in the medium range. Some sisters who go for branded rather than drugstore makeup, regularly rent hotel rooms to crossdress or undergo permanent hair removal will see their costs shoot way higher. And most would have purged their perfectly functional female wardrobe at least once during their journey, which further adds to the costs.

But like my dad likes to say: "钱赚来就是要拿来花的"。(Loosely translated: We work to earn money, so it is only right that we spend it"). Despite being an expensive hobby, crossdressing makes us really happy and we are very willing to spend on the inner woman. Life is short, so we should try to create as many happy moments as we can. 

Nevertheless, I believe it is important to focus on what the guy mode does to grow our finances properly. Only when we are well able to meet our basic human needs do we have the mental and financial bandwidth to properly spend on our hobbies without worries. Swap out "crossdressing" with any other hobbies or whims in life and it still generally holds true.

(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.

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 🤣

This is a post to any wife / girlfriend who stumbles onto my rather obscure blog (no no no please don't leave! I promise some insights!)

You're likely reading this post, because somehow you just found out that your Prince Charming actually prefers to be the princess, and life as you know it is crumbling before your eyes. There's a million questions in your mind and you're not sure if you know the answers to them. 

I will be upfront and tell you that your situation isn't unique, but it is undoubtedly  complicated. So let this fledgling blogger and life-long crossdresser attempt to answer your questions. Please note that these are all my opinions and I hope I do not inadvertantly offend anyone. If you want to read about my coming out story, you can find it here.

No, your husband / boyfriend is not a pervert just because he likes to wear women's clothes! There are a myriad of reasons why men likes to wear ladies clothes and makeup to feel like a woman; some just want to look pretty, some do it as a form of escape, some want to destress, some are turned on by crossdressing, some view it as an expression of themselves, some just do it for fun to confuse people, while some are transgender. What is common is that crossdressers tend to experience the urge to do so from a very young age (around 10) and they have been doing so in secret because this behaviour is frowned upon.

Although crossdressing may be viewed as a perversion by some, it shouldn't be! Women crossdress all the time, by wearing clothes which are supposedly masculine, such as boyfriend shirts or pants, but don't get any flak for it. Society is still largely unable to accept why a man would want to degrade himself by putting on lacy undies and wear a dress.

Personally, I view crossdressing as a hobby like any other. It brings joy to the individual, there are amateurs and professionals in the field, and as long as it is not illegal, done obsessively or cause grievious hurt to others, it should not be seen in such a negative light as it is now. 

It depends. Loving to crossdress and looking like a woman does not automatically make one gay. There are many crossdressers who are straight and cannot fathom to get it on with another guy. However, there is also a possibility that he is afraid of tell you of his interest in men, or he could be in denial of his sexuality.

Do consider broaching the topic gently to tease out an honest answer to your question. You need to be aware that there is a broad spectrum of sexualities and for your partner who has been a closet crossdresser since young with no one to talk to about his secret, it has been an extremely confusing journey.

Probably not, if he says so explicitly. If your partner came clean to you about his crossdressing, it means that he wants to continue his relationship with you and has decided to confide in you in hopes of gaining your acceptance of his occasional crossdressing.

However, there is a possibility that he is so deep in denial that he does not realise that he is actually transgender at the point of coming out to you. Once he becomes more honest with himself, he may "come out" to you again some point in the future. It is important that you sit down with him and calmly understand his motivations for crossdressing. To be fair to yourself, if you are uncomfortable with your spouse transitioning, it should be made clear right from the start. 

NO! As much as you are emotionally hurt and feeling betrayed, telling a 3rd party about your husband / boyfriend's crossdressing has massive repercussions. Not everyone has the discipline to keep such a juicy secret under wraps and it can spread like wildfire. Society generally frowns upon a man in a dress; as such, crossdressing behaviour can potentially damage careers or wreck family relationships. Your husband / boyfriend may have struggled for years and finally decided to trust you with his deepest, darkest secret. It is only right to treat his confidence in you accordingly.

 

I repeat, please DO NOT spread his secret to 3rd parties.

Unfortunately, that is a promise that he will not be able to keep. He probably said this in the heat of the moment, so as to stop you from crying/screaming at him/convince you not to leave him. He might be able to purge his ladies' clothes completely and bottle up his emotions and urges for weeks, months, even years. But all it takes is a trigger and his crossdressing will come back with a vengeance. It sucks for him because he is in a conundrum; he cannot dress openly or you will know he has broken his promise, which will shatter for a second time the illusion he had rebuilt. The only way is thus to do it in secret and hope you do not find out

Sorry fellow crossdressers. You all know this bit is true.

This is a situation where I think there is a need to separate (i) the act of crossdressing and (ii) actions of infidelity. 

Although some religions may disagree, the act of crossdressing in itself is not wrong or harmful. It is simply wearing of clothes that are normally associated with the opposite gender. However, actions of infidelity wander into the realm of betrayal which I think should not be condoned. Yes, crossdressers can be sexually confused, but it is not an excuse to go around trying to hook up with other people when you are married / attached.

If your partner is a great person, is straight and dresses as a woman occasionally, you could consider setting ground rules such that you do not need to see him enfemme. It will be a compromise position, which is a win-win for both parties. He would appreciate your acceptance of his crossdressing and bring his crossdress into hiding, and you will not need to break the mental image of him as a masculine guy.

However, everyone is entitled to their opinions. If the mere thought of your partner wanting to crossdress repulses you so much that your normal life / love life is affected, perhaps it may be best for both parties to go separate ways.

Firstly, calm down and don't freak out. You are in a situation where the best course of action is to have a frank sit down talk just between your partner and yourself. It might be difficult and potentially long, but this is the only way to properly understand the situation. If you need some time and space to clear your thoughts, let him know.

He is telling you because he is trusting you to keep his secret and hoping for some form of acceptance. To be able to crossdress freely, in the comfort of his home without the need to hide it from you. It may come as a shocker but chances are your partner is more terrified than you are. Remember that he has probably never told anyone his secret and is extremely worried about your reaction to him coming out, especially if you are married with children. 

You are under no obligation to accept his behaviour of course, but it is important to view it objectively. Just because he likes to wear silkier, lacy clothes at home does not make him a totally different person.

I think it is important to ask about his sexuality and whether he intends to transition. These are important issues that can be deal breakers for many relationships.

Ask about his crossdressing story. When did he start doing so, how did he start, why does he do it, where does he keep his ladies' clothes, whether he has gone out in public enfemme before, whether he has told anybody. You should also find out why he is choosing to share his secret with you.

If you're feeling bold, ask him to show you how he looks like enfemme. However, be careful not to mislead him into thinking that you are accepting his crossdressing if you feel otherwise. Honesty is the best policy, but the situation should be handled delicately.

There are many articles and resources in the internet answering questions from distressed wives / girlfriends about their partner's crossdressing, especially on forums like reddit and quora. Do take what you read with a pinch of salt as everything is someone's opinion.

However, you can take some comfort in knowing that you are not alone in the world out there. And if your husband / boyfriend is an awesome person whom you want to spend your life with, accepting his crossdressing will definitely make him cherish you even more and enhance your relationship further.

I decided I had to come clean to her. Honesty in a relationship is important, and if I had to face an enraged spouse, I rather control the parameters of the confrontation than be caught in an uncontrolled explosion.

With the internet at our fingertips, there is a wealth of information on transgender issues, gender dysphoria, challenges of being transgender, how to present oneself as female, youtube videos on makeup and crossdressing, etc, which makes it easier to "level up" and be more knowledgeable about the subject. Most of these are generic and applicable regardless of which country one is in. Resources in the English language however, tend to be be largely originating from the US or the UK, which also meant that the struggles or coming out experiences were in the context of their society.

It meant that it was hard to read or hear the struggles or coming out experiences in a local context. To make matters worse, crossdressers who don't identify as transsexual (i.e. don't intend to transition) form an even smaller slice of the transgender pie. The majority are usually so deep in the closet no one knows about them (I know, I used to be one).

As expected, resources on crossdressing in a local context (Singapore / Malaysia) are extremely sparse. Search "Singapore Crossdresser" on Google and the top few results are about dating crossdressers, news reports of crossdressers being arrested for some crime, or some porn site (Don't get me wrong, I've got nothing against porn). It is really not difficult to understand why crossdressers are very easily viewed by society as perverts or deviants (fortunately, there is always Wikipedia, a very neutral and informative, if not overwhelming source of info)

There used to be a forum called SGButterfly, which I understand that in its hey day, was an active online platform and safe space for exchange of information and experiences between CDs/TS both mtf and ftm. It has unfortunately been shut down, but we've got to accept that forums are a medium of the past. In its place there are facebook groups for crossdressers, but these tend to contain superficial content (i.e. posting of photographs)

I hope this blog on my crossdressing journey and answers to common questions serves as a decent guide to some of you readers. 

As an easy reference, I also list some of the local resources on crossdressers (and some transgender) that I have come across in the past.