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.
