Come as you “are”…


I haven’t updated in a good while, though I think that may be that the previous updates had let me settle some elements of my “hobby” with myself more comfortably. I’m genuinely coming closer to grips with my crossdressing habit. It feels less and less like a shameful secret and more and just a very personal and periodic fantasy. With this, I’ve begun to make shallow but definite efforts to actually sharing myself dressed in my feminine outfit with other people in a real space. Oh my…

It’s actually been a little while since I’ve dressed… hard for me to part with facial hair 😛

There are lots of things I’m considering in this. Being the crossdresser I am, I’m remarkable a control-freak about how to engage this kind of encounter. Here’s a list of things I’m thinking about… excuse me while I publicly ask myself these things… I appreciate your replies and input as well:

Do I show my crossdressing to people I already know, or to new people?

This one I feel more or less sure about. If the purpose of my meeting is for crossdressing, I’m much more prone to engage with “new” people, in a crossdressing club or circle or sorts (actually, the country I live in is quite friendly to crossdressers in this regard).

But I also consider the idea of, say, going out en-femme for Halloween as an option — or to a costume party, or concert, or other “themed” event. This would make the event much more immediately accessible and also give me the comfort of passing off dressing as a one-time thing or “just for fun” (which, honestly, it most likely only is).


Do I share myself with other crossdressers, or around non-crossdressing people ?

This one I also feel more sure about. Other crossdressers seem much more approachable than even trans-friendly guys or women. General transgendered folk also seem like a safe bet (assuming “transgender” is different from “crossdressing”), though there is a kind of intensified sensation I would feel around someone “openly” transgendered (i.e. they live their normal life as the opposite sex) – as there is this vague sense of “Oh, well he/she can walk outside freely – I have to change… perhaps he/she looks *down* on my secrecy…”.

For first-time encounters, at least, probably other crossdressers would be more comfortable – but what if said person has done it hundreds of times before?

(God, I sound worse than a virgin 16 year-old)

Where do I actually do this… in my own home? In some shared-but-private space?

I live in a country where there are many small privately-owned spaces available for patrons and customers to engage in the kind of behavior I wish to. There are even dedicated “crossdressing bars” to get started at – you can go inside, get dressed up, have a few drinks, even some “play” rooms. This seems like the right kind of place to start, but what if even that feels like a lot to go forward with. Sharing my living room with one other person, just chatting and watching a film or taking pictures together seems like a perfectly fine idea to me, ah.. but…

Do I go one-to-one, or with a group?

As tall and frightening as I am without heels, I’m not really afraid of what can happen in a one-on-one encounter. I’m more concerned about how quickly things can get out of hand. See below…

What do I actually do in this kind of situation?

Crossdressing is still largely a ‘sexual’ activity for me, so I feel like I need to ask “will doing this around another person I’m attracted to lead to sexual activity?” or “Will I be able to control myself… and will doing that make other people uncomfortable, or end badly for myself and/or someone else?” – ugh, and that by itself is a big enough question. I’m actually quite conservative about engaging in sexual activity – well, not in the activity itself, but in the partner(s) I do it with (I’m a terribly emotional sucker).

Writing these ideas out helps me more or less “feel” what I want, and I think that is a good thing. I’d like to get the opportunity to try at least, but I want the decision to go forward to be a free choice. Obviously there are risks involved in doing this, but I feel like sharing it with someone could help me greatly and finally give a sense of “completion” in the emotional and psychological mindfuck experience of crossdressing. Furthermore, having more confidence in this aspect myself makes me more accepting of the risk of it becoming public knowledge.

Will these things continue to be an issue for me? Or will I lose interest?

I’d welcome any and all thoughts on the issue D:

Healing through comedy. Dress to Kill

The above video comes form Eddie Izzard’s “Dress to Kill” DVD. The first time I watched this routine was in my high school years sitting with a few friends, including my then-girlfriend. At this time I was still a bit early into my crossdressing habits, but I had long been confused by that point as to how sexuality delineated from my behavior. After all, I liked girls, but I also liked wearing girl’s clothing — so clearly there must’ve been something wrong with me… right?

It was with great anxiety I started watching this video as my friend introduced the act by saying “He’s funny and he tells jokes while wearing women’s clothes”. In fact, before watching, I thought a great deal of the humor would be played ON Izzard, somehow pointing and laughing at the ridiculousness of himself being dressed as a woman — and I would subsequently sit and laugh awkwardly about it.

It was barely 1 miute into the video and I absolutely fell in love with Eddie Izzard’s wisdom — conveyed through comedy, of course.

To my surprise, he came out straight and cleared the air not only about his own crossdressing habits, but also the sexuality involved. Hell, I shared a great deal with Izzard — I too loved outdoors activities (“running, jumping, climbing trees”), I too wanted to be in the military as a child, I too was worried about being conflated with all sorts of “weirdo” transvestites, I too fancied girls, I too was terribly afraid of my habits being discovered on the school yard. Holy shit… so much became clear to me, and I wasn’t laughing AT Izzard…. dear god… I am laughing WITH him… and the laughter came from deep within my heart as I knew full well that I understood EXACTLY what he was saying.

Everything Izzard said rang loud and clear for me. I started to imagine that “Hey… maybe there ISN’T anything wrong with me. Maybe this is natural. Maybe this is just WHO I AM.” — and he conveyed all these ideas with such candor, wit, aplomb, and clear-cut confidence that I suddenly had a sense of a distant, kindred spirit who had undergone the same EXACT confusion as I had.

I hope future generations of crossdressers — of all kinds — find Eddie Izzard somewhere in their journey. There are many great writers, paragons, and moguls of transvestism, but few I have found to have the same remedial effect on my heart as the first time I saw this act.

The Fear of Being Caught

Perhaps nothing in the world tops the lengthy list of a crossdresser’s worries than the fear or “getting caught” crossdressing. It is perhaps the single largest life-ruining event that has undoubtedly resulted not only in terrible shame, but broken marriages, families, even suicide among those who practice crossdressing behavior privately.
First of all, let’s look at the terminology crossdressers tend to use when describing the situation where their dressing habits are revealed. “Getting caught” is the same word used when describing an act that is generally against the law, or against the rules in general — i.e. “I got caught stealing a candy bar from the supermarket” or “I got caught skipping work to play golf” yadda yadda.
By using the term “getting caught”, crossdressers are implying that there is a illicit or “wrongful” nature of the act they are practicing — prolonging the misguided idea that dressing is something they, in fact, SHOULDN’T be doing. While sometimes it this very reason that drives one to crossdress, one should be wary of the way they interpret an incident where they are seen crossdressing.
This can be particularly harmful psychologically. Crossdressing is and mostly never has been a socially acceptable behavior, but that does not mean we should feel it necessity to assume the blame for our behavior being observed. 
Almost anyone who inadvertently witnesses a person crossdressing would likely know that said individual doesn’t want others to see or know about it. This is not to say an individual is to blame for seeing something they cannot “unsee”, but in the case of crossdressers, particularly of the private variety, the most likely person to witness your behavior is going to be someone you know personally.
There are a multitude of ways this can be dealt with, but to illustrate my point I will use my own personal example — the time I was “caught”.
When I was undergoing a rather confusing time in adolescence — somewhere around 13 or 14 years old, I took a weekend trip with my friends. Meanwhile, my parents decided that, while I was away, they would rearrange the furniture in my room. When searching underneath my bed, they discovered my boxes of skirts, pants, dresses and other items in had collected from storage in our attic and crawlspaces — clothes my mother no longer wore but kept anyway (I have a family of pack rats). Central to this collection was a pair of high-heel boots that I had modified by cutting out the back heel so my big, boyish feet would slide inside.
Perhaps moreso than the girly clothes collection, my parents were furious that I would so wantonly destroy their property. 
When I returned home from my trip, I endured a severe staring-down from both my parents at once who demanded an explanation. They even locked the room we were in. I was mortified. It was like an interrogation of the worst kind. I broke down and sobbed all the fears out. I sincerely couldn’t feel any worse. As they looked on, still completely bewildered as to why I would cut up my mother’s old boots, I blurted out in both anguish and fear that I had worn them while masturbating. I’ll never forget how they stepped back after this. They even asked me to repeat myself more calmly. After I did, my parents looked at each other and my mother left the room. My father sat down next to me, and calmly told me that during this age, I would go through a lot of sexual feelings, and sometimes I would feel the need to experiment. He then said that they were only upset because I damaged their property, and ended the conversation there. I had to reimburse them, but after that, my parents never made issue of this incident again — they never mentioned it or brought it up.
As I got older, I sense my parents continued to know what I was doing when they went away on trips — but they never mentioned it and never alluded to it in any way. 
In retrospect, this seemed the best possible outcome. Sooner or later, someone finds out you are a crossdresser — whether you disclose it willingly or you are “caught”. Some people understand that this kind of deviancy is prevalent in society, that — while a bit abnormal — is not any more abnormal than if someone likes to smell feet or wear silly hats.
I’m glad the upbringing I had neither encouraged or discouraged me from discovering these sensations for myself. I’m also glad that I learned the value of having to confront that fear of being “caught” without it ruining my life.
These days, I feel less “shame” about my crossdressing habits — though I do retain the right to keep it a private matter and I would expect individuals I know personally to keep it that way should they become privy to this aspect of my life.
After all, “Let he who is not a freak in some way cast the first stone — so we may know better the plain and unimaginative among us.”Image

Being a man being a woman.

IMG_0860Both images above are of me, separated only a few minutes apart (it takes a good 20-30 minutes to put on my whole outfit :3)

I may be self-absorbed, but I do try not to be too arrogant. I have worked hard on my body though, since being in university I’ve been working out very consistently — weightlifting, circuit training, two-four miles runs and jogs — dragging my sorry ass into the gym while my friends went out to parties, etc. The good news is that I can maintain good health and ‘decent’ physique with what I may qualify as ‘relative’ ease of maintenance — i.e. I don’t need to go on a lengthy diet to lose weight, etc. Oh yeah, and I never have to worry about getting sex — if that’s what is motivating me (read: it’s not).

So what is it? Can I be both masculine and feminine at once? Are these things so inherent different? What nature of my persona, through working out and crossdressing. is projected onto either male or female identities?

Both of these behaviors may be simply classified as “hobbies” (as it relates to conversation), but are more accurately understood as “lifestyle choices”. Both involve a great deal of time and energy. Both are activities undertook alone. Both involve little speaking and thus little reliance on the will of others. Both are self-indulgences. Both are narcissistic at heart. Bother require the prominent use of mirrors to fully benefit from (see my earlier post).

For one, it comes with to little surprise to find many of the ‘gym rats’ I surround myself with have a plethora of sexual identity crises — seemingly enhanced by the exceptional seriousness with which they approach the notion of their masculinity. Working out is itself a very sexually charged activity — so the hormones get flowing and suddenly we’re all down the river without a paddle. It is a cesspool of sexual deviancy — and I don’t just mean homosexuality.

Truth is that, for the muscle men, exercise (and weightlifting in particular, I may add) is a very self-loathing and self-punishing activity. With great passion we seek to destroy our current selves, through little more than sheer force of will, and create a new self — all the while being absorbed wholly in our own physical existence.

Crossdressing, by contrast, is a self-loving activity. We reward ourselves with excitement, self pleasuring, the general satisfaction of wearing hosiery, skirts (women have it fucking MADE in that department), and other forbidden articles. The longer we can sustain this excitement and maintain the feminine illusion, the more we can attain pleasure. Some men even take it a step further to crossdress under their regular clothes (i.e. the image of the CEO who wearing women’s panties under a suit, etc.) to feel closer to the self-love associated with dressing up.

But most importantly, both these activities are unified by being modes of physical sexual expression. Both are intimately related to our physical sensations — I desperately love the female figure so that I want to actually adopt it as my own from time to time (no, I’m not trying to kill you or wear your skin, we are talking about clothes here… if that is at all less creepy :P). Both working out and crossdressing carry a quasi-sexual element to them — both are motivated by sexual desires but ultimately succeed in achieving our focus and commitment not in the end result, but in the actual processes . Both activities make us at least feel sexy to ourselves. Both ready us for sexual arousal (ever have sex after a long workout? Great sex, mmm… good times.). Both charge us with sexual feelings and a desire to acquiesce to sexual desires. Both permit us to exhibit alternative behaviors.

I find little irony in being able to spend the morning doing bench presses and super sets and then spend the evening powdering my face and slipping on a skirt. These activities don’t seem in any way opposed to each other as gendered behaviors in my mind. –they are both parts of a passionate, narcissistic sexual expression — one that is not reliant on the provisions, emotions, or attitudes of another person. If anything, I think they just show that I am an individual motivated by intense sexual desire.

the NSFW story of developing crossdressing habits

IMG_0810My adventure with crossdressing began as early as I can recall the first development of what would become sexual urges in my youth. I think it hit me fairly early, at least a year or so before what is generally average. I’m not sure on the data, and others with knowledge on the subject would be invited to comment on it. In the 3rd and 4th grade (ages 9-11) I developed what would become a mild fetish for wearing what I considered “dorky” or “geeky” clothing – khaki pants and button-down shirts (of the male variety). In fact, much in the way a young boy may actively resist the company of girls (and I did that as well, for my part), I actively disliked wearing any shirt with buttons from a young age (6 to 8 or so). I felt such clothing made me look “dorky” and therefore, in some ways “vulnerable”. I would refuse to put on “nice” clothing at the bequest of my parents for Sunday church services.

However, as I entered the 3rd and 4th grades, and as my time to spend alone grew after a move from one state to another, I began to experiment with wearing these “dorky” clothes more often. I would feel a sudden urge, upon increased time spent on my own, to wear the clothes that otherwise made me feel “weak” “vulnerable” and “open” – as if my friends who caught me wearing such things would ridicule me to no end (in middle class white society, I now understand they wouldn’t even notice). Part of these outfits would involve pulling up my pants so the waistband would exceed my belly button, and tucking my shirt in. At some point, these urges grew and I became what I would later understand to be sexual arousal. At the time, I was drawn to violently rub my crotch up and down, using both hands in rhythmic body movements using the fingertips to stimulate my penis, often best performed in front of a mirror. These kind of episodes resulted in my first ejaculations, which were mysterious things to me as any young child. I would, however, require the utmost privacy for these, embarrassed to be seen in such clothing. Immediately after ejaculation, the flush of intense stimulation would leave me feeling quite embarrassed and I would immediately remove this clothing. I believe this type of feeling would be well-understood by my fellow crossdressers.

As I got slightly older, these experiences became intertwined with general fantasies of intercourse with girls. General episodes of donning “dorky” clothing would be mixed with late night or early morning episodes of rhythmic “pillow humping” or any sort of base ejaculation method. Sometime around the development of more clear sexuality (and a ready identification with these feelings as that), I began to simultaneously fantasize of having sex with women while also wearing their clothes. As I reached age 11 or 12 or so, an age where daily socialization and general attraction to girls began in my adolescence, this lead me to alter my own male clothing to appear more feminine, as well as wearing old, tighter clothing of my own. This was the first time I was readily identifying my dress as something distinctly “feminine”, and I would adopt a feminine person in these clothes. Above all, the act behaving girly was seemingly an expression of the great mystery of the opposite sex – something perhaps I could come to understand through imitation.

Over time, I played with idea of searching for my mother’s old clothes as I made a late night sneaking mission to recover some lost article of clothing to fit myself into. The first moment of putting on a true to form piece of women’s clothing – as I’m sure any crossdresser would tell you – is an emotional rush unlike any other. It was as if the entire resistance to project myself as weak and vulnerable was lost and I was finally 100% into the act – a performance to dress rehearsal (excuse the pun). Over time, I collected these items with increasing regularity, paying close attention to the times I would be left home alone and become suddenly aroused when those moments came. I organized the pieces into small collections and outfits and would experiment with the feelings of mixing different articles on.

Meanwhile, the urge to resist this embarrassing behavior was also strong, and I felt a duality grow in my actions. Often, however, the sexual element of crossdressing would outweigh the asexual element of remaining “strong” in the face of such urges – at least when time allowed it – as if some unseen observer were watching me perform my crossdressing sessions with great disdain. In fact, having been raised in a marginally religious household, I felt God disliked my behavior, and even punished me for it with negative feelings and general confusion (at which point, I ask whoever was at first not confused at the onset of their sexuality to cast the first stone).

The greatest times to my memory are then the times when my parents and brother would be gone for extended periods of time. Once my family was from early morning to the next early morning, and I recall awaking early to put on my clothes, only then to enjoy the simple bliss of everyday activities conducted in women’s clothing (often a tight pair of pants and a tight turtleneck, later with a pair of rolled socks to serve as ‘breasts’).  Even the simple act of eating breakfast and watching television was blissful in this state, while the urge to sexual please myself was equally strong, I was equally held in limbo by the desire to try new clothes or simply “play” in these outfits.

As I grew older and my independence also increased, I actually made the considerable leap to purchase my own sets of fetish female clothing – the type I frequently fantasized about both wearing and engaging in intercourse with women dressed in – aided in no small part by the relative anonymity of the internet and online auction sites. This process allowed me to taste the actual act of shopping for my own clothes, as if I were a woman, within the safety and confines of my own private space.

As this behavior increased with regularity, the desire to wear these clothes in private over extended periods grew over time as well. Few things excited me more than to don a full outfit (which, to wear properly, took considerable time to put on correctly) and to engage in the simple act of cooking eggs, watching a movie, or even playing video games. On rare occasions I would talk on the phone while ‘dressed’, delighted in some strange way that the person on the other line was completely unaware of my particular clothing.

Narcissism = Crossdressing


The central item to any crossdressing session is no particular piece of clothing. While everything from high-heel boots to corsets, bras, panties, wigs, lipsticks, powders, and various pantyhose took their proper place, nothing is more important to the process of crossdressing than the almighty mirror. In fact, without a mirror, the whole act seems purely as a personal means to obtain an orgasm.

The act of crossdressing, therefore, as far as it may concern myself I may contend, is at heart an expression of a self-indulgent narcissism – a subconscious belief in personal beauty and adaptability — a superiority in beauty to the desired sexual object (a woman or other fantasy).

As I have gained more confidence in my ability to appear feminine (subjectively, as I share my hobby with precious few), I have begun to record these sessions with a camera or video camera, and would obtain exceeding pleasure from time spent experimenting with various photo-editing methods to give my feminine self a more developed persona – incorporating various poses and peripherals to aid me in developing an increasingly feminine appeal.

It is wholly possible that I am projecting my own rationale over others, but I would wager that all crossdressers — from young to old — weak and powerful — those who dress in private or public — all share a common need to indulge the self-absorption that comes with the act of crossdressing.

I am a crossdresser.

IMG_0762With some trepidation do I even type these words. It is long the secret I have lived with much of my life. Now that I am older I feel more confident in my feelings related to this aspect of my life.

I am a crossdresser. Not at all times, but periodically I don women’s clothing (or men’s clothing in a womanly fashion) and place a wig on my hair and generally make my appearance to be as feminine as possible. I do this in the privacy of my own home, in my own space, and without the intent to do harm to others – except perhaps the self-destructive harm I inflict upon myself in the process (which is debatable to begin with).

My experience with crossdressing is certainly not unlike many others who experience such feelings. Though I feel alone in the “real world” of daily life with these thoughts and feelings, I know through other outlets (namely the internet, where this record is published) that I am not alone and likely in considerable company worldwide.

To clear the minds of the curious, I want to dispel a few misconceptions this confession may bring forth. To start, no, I am not a closeted homosexual, and I do not necessarily consider crossdressing to be a homosexual act. I point to British comedian and public “executive transvestite” Eddie Izzard in his diagnosis that a our type is more akin to a “male lesbian” – yes, I do fancy girls. I even try to be one.

Creepy though that may seem, I do not feel at this particular time a desire to crossdress in the presence of others . That is, at least in the degree to which I would be readily identified as a crossdresser. It would be lovely if I could remove the inconvenience of having to control my urges to dress with time that I would otherwise be able to spare alone. I do enjoy chatting with others in my dressed state. Maybe some form of interaction through that means would be a first step to “dressing out”, but I prefer the comfort and privacy of my own home for the time being.

I do not have any plans or strong desires to ‘become’ a ‘real’ woman (i.e. hormone therapy or surgery, etc.), though I do consider the act of crossdressing a transgender act. Nor do I incorporate feminine aspects of behavior or mannerisms into my “public” life. I am as masculine and ‘boyish’ as they come on any given day.

Finally, I feel not particular need nor desire to “come out” to my friends. It is not that I fear what they would think, but much as one might not wish to dig into someone else’s porno stash — I don’t think they’d be particularly interested in what I do during my free time.