My Early Life as a Crossdreamer

I know that, as a young boy, I used generally to wish—not intensely, not praying desperately to God, but regularly—to become a girl. Which is to say, I have a general memory of having that sort of a wish regularly. I didn’t have them all the time, not obsessively—not, as many trans women describe, in a way that seemed to flood my whole self leaving nowhere to stand—but recurringly. They were not rare and thus not surprising when they happened.). But I have only a few specific memories of specific incidents.

The earliest memory I have of crossdreaming1—at least, the one which I am best able to pin down, and give a specific upper bound for the date—had to have been when I was ten years old or younger, because my family moved when I was ten, and this happened in the old place.

I don’t have a very specific memory of what caused this, nor did anything in particular happen. But somehow the thought occurred to me that if a woman on television—I was imagining, I think, a talk show, where guests sat in chair next to the hosts, like the old Johnny Carson show (although I don’t remember watching that one in particular)—if, as I said, a woman on television were wearing a skirt, and was careless, one might see her underwear. Not that this had (of course) ever happened; it was an entirely theoretical notion for me. Nor did the idea that of course women who wore skirts would be conscious of this problem and avoid it ever occur to me (I suppose I wasn’t the brightest of children). But the idea fascinated me, and I thought about it, to the best of my recollection, intensely and for quite a long while. And I remember hoping, really hoping, that somehow I would become a woman, or just wishing I had been one—I am not sure that the precise differences between various subjunctivities had clarified for me.

I am not sure to what degree this was a sexual thought; I was, again, ten at most, and I don’t think I was a sexual being yet.2 But it had the intensity of sexual longing, even if it wasn’t, quite, sexualized longing. I found the idea of that sort of embarrassment, of being seen, deeply, overwhelming fascinating. And what I thought about, what excited me, wasn’t the idea of seeing up a woman’s skirts on television. My thoughts were entirely consumed with imagining that I was a woman, and thinking that if I were, and got to go on television I would make sure to wear a skirt, and maybe even show my underwear on purpose. The idea thrilled me (typing it now, four decades later, it still sends a thrill through me, even as I recognize it as juvenile and silly).

As I said, nothing came of this; it was just a moment, or possibly more than one (I think I recall it being a recurring thought, but have little confidence in that memory). But it shows that the idea of my becoming a girl or a woman (I was a boy then, and knew I would become a girl; but what I dreamed of was later, when I was grown) was old in me. Not just an idea: a longing.

—This memory is interrupted by another, this not precisely crossdreaming-related (let alone autogynephilic)—or, at least, I can’t remember that it was—but is psychologically related, so I shall relate it here. Once, and only once, when I was a little kid—I think I was about five—I had one of those “show me yours and I’ll show you mine” moments that young kids reportedly have with the opposite sex. I remember I asked her where her pee came out, and explained where ours did. But somehow the game ended up in a sort of pretend, and I remember that what I wanted to do was have her pretend to show me to other people—still exposed—so that I would be embarrassed. And this was not an idea I had at the moment, I’m certain of that; this was a long-standing scenario (being seen naked, being embarrassed) that I finally had an opportunity to turn into play. Here the notion of sexuality is even more distant. But the longing for embarrassment was there even at that young an age.

Returning to more strictly cross-dreaming memories, I have one other—another moment of longing and fantasy, one which was, I think, one of the most intense of my entire childhood—which I can date, this one quite precisely, to my fourteenth birthday, during my eighth grade year. By the age of fourteen, of course, I was no longer young enough not to be a sexual being.3 But my sexual desires were all pretty inchoate—I wanted, wanted desperately, but what I wanted wasn’t even the slightest bit clear to me (I don’t think I had yet masturbated, nor had enough sex ed to understand the basics of what I was desiring). So what role this budding sexuality played in my desire to become female is unclear to me, certainly from this vantage point. I don’t think it was entirely sexual; I don’t think it was not at all sexual, either.

But I know that, at the time, I used to have regular fantasies that I would, somehow, magically transform into a woman.  These were not, certainly, the only fantasies I ever had.  I was a pretty dreamy kid, I guess, and I used to imagine all sorts of magical transformations — that I would somehow become smarter, even super-smart; that I would instantaneously learn things I wanted to learn (another language, an instrument); and the like.  So the idea of imagining a magical transformation was hardly unusual for me (I have no idea, really, how unusual it is broadly speaking, although I have gotten, from hints and asides and stories, the idea that I am far from the only one).  But the fact that these dreams included (often included? always included? As with so much, I can't at this distance say) the idea of my transforming in sex seems, at least, notable.

And I think I would often pick some moment when I hoped this would happen. The most common, I believe, was falling asleep, I hoped (not prayed: we weren’t a religious family) that I would wake up in a girl’s body. I don’t know how seriously I took these fantasies. I think, if you’d asked me, I would have said that of course I knew they were foolish and impossible, and that on some level I really did believe it, but on some deeper level I let myself hope that I would be surprised, that I was wrong in my realism. You never know for sure, I would have (and did) whisper to myself. Pseudo-mature certainty wrapping an even-deeper maybe.

But one of these times was, I think, the climax of them: the climax, because unlike most such fantasies, it was not fleeting, but fixed in my mind as the date it would finally happen weeks in advance: my birthday. I somehow gathered up all the earlier fantasies and took them as minor and preparatory, and built up in my head a detailed scenario. At the specific moment in the afternoon when I had been born (i.e. not only my birthday, but my birth minute), I would fall over in some sort of a coma, being instantly wrapped in a magical cocoon. When it broke open—a minute, hour or day later, I forget what I was envisioning—I would be a girl, forevermore.

So while this wasn’t a new desire—it had very specifically been a long-time one, although how long I couldn’t say (six months? A year? All the way back to my ten-or-under wishing to have my girl’s underwear seen on national TV?). But this was, in my mind, the big one: I took the birthday date was set as a for real this time moment: a way to pretend, and perhaps half convince myself, that it was going to happen at a particular moment, not the next morning, but at a date which was still week or two (or more?) out.  That way, you see, the fantasy could persist for longer.  Rather than hope one night, and wake up disappointed in the morning, I could fall asleep hoping and wake up still hoping.  This clutched straw became the cornerstone of a large edifice of desire. The persistence of this one date made it a point of fixation and, therefore, all-the-more-intense hope.

Again, I wasn’t delusional; this was a fantasy. If asked if I believed this was possible I would have said, and meant, no. But I also hoped it would anyway. On some level—deeply and partially enough not to rise to the level of clinical delusion, but still a level that made it a very strong, childish4 anticipation. I didn’t expect it. And yet I did, in the same oh-I-know-it-won’t-but-maybe way that you watch the lottery on TV, clutching your ticket in your hand.

It was a Saturday, but I was at school: I was in the eighth-grade play (as many of us were), and there was a Saturday rehersal.5 I was not on stage at the key moment, but was sitting, along with others not in the scene, where the audience was to sit.  (Perhaps it was a dress rehearsal?)  And I remember, as the kids on stage strutted and fretted their hour, and other kids watched, or whispered, or were bored, I watched the clock approach the fateful moment. I remember as the second hand swept towards twelve on the school clock sending a mental good-bye to my girlfriend, from whom, I supposed, I would now be parted. (I suspect that I had not, at the time, ever heard of homosexuality; certainly the very concept of a lesbian had never entered my mind: this was the 1980s, and “the past is a different country: they do things differently there”.) The clock on the wall (I think I didn’t yet wear a watch) clicked on. The minute hand, and then the second hand, approached their marks.

To say that nothing happened is, perhaps, the least necessary sentence ever written.  But I also don't recall for certain what reaction, if any, I actually did have to that fact, although I have a vague sense that I was embarrassed at taking it even as seriously as I had.  And, I suspect, a sense of deep disappointment, as well, one which I hardly let myself feel, since to do so would just be to take it seriously, and compound my embarrassment further. But I had, this time, hoped longer, desired more intensely (since many weeks’ desiring was heaped onto one particular point)—hence the intensity of this particular disappointment, which translates to the intensity of my memory of it.

In memory, the long train of earlier fantasies that I would wake up the next morning as a girl stopped after that. I doubt they really did; I remember them happening later, although only significantly later—possibly high school, but certainly and often in college and after. But memory wants to put a pause after this particular Great Disappointment which (as such Great Disappointments are historically known to do) changed rather than caused me to abandon my particular fantasies.

It's not that I would have said, if you had asked me then, or even decades later (but before a few years ago) that I thought that such fantasies were rare or unique to me.  Since I was (of course) never asked, it never even occurred to me to wonder about their rarity at all.  I felt them, but I never, as far as I can remember, thought about them.  It's not that I was ashamed of them, nor that I felt weird or alone or anything.  I didn't think about them beyond the having.  It was simply something I dreamed of.  Something I knew was impossible, just as I knew that magically becoming smarter or fluent in French or more organized or myself but better was.  Yet I also knew that, if I were to be granted some set of personal transformations, a change of sex would be on the list.

Strange as it seems in retrospect, I even mentioned my crossdreaming to a friend once.  Shortly after the stumbling on transgender porn made me realize that I was not alone (which I discussed last week), throwing a spotlight on this strand of memories which suddenly stood out like the alternate possibility in a gestalt pattern—

Famous gestalt image which can be either an old or a young woman
This famous image (which can flip from old to young woman) stands out in my mind both as a symbol for the mental transformation that the realization caused in my view of my own past, but also for the sort of magical flip I hoped, as a child and teenager and, yes, frequently as an adult, would happen bodily to me.

—I would have sworn I had never mentioned these thoughts to anyone.  In fact, I said to someone once (pseudonymously, on the internet) that I had never spoken of this to another soul (I will return to this exchange later), but eventually, as I explored the newly-lit terrain of my past, I realized that that was wrong. I recalled that I had, in fact, mentioned it to a friend. Once.

He was my best friend in college (and later my best man at my wedding, and still a very dear friend to me); he had just come out as gay to me,6 and we talked often about this as he processed the life he was entering (so very different in the early 1990s than even a decade later, it is hard to accurately convey), so we had been speaking of fantasies and desires often. In the course of one of those discussions I must have mentioned — I can barely credit it, even as I remember it — that sometimes I just wished I had been a woman.  I don't recall my friend's response.  I then asked (with some sense, I think, that everyone, or rather every man, must want this, at some level) if he didn't feel the same way.  "No," he replied, "I like my cock too much."  Well, I said, I wish I had been a woman.  "You can make that happen if you really want it," he said, gently, kindly.

But while I don’t recall what I answered, I did not take the idea seriously. I think I had a vague sense that the surgeries that were done (and there was never the slightest doubt in my mind that if I were to contemplate it, it would mean surgery) were not good—that I couldn’t really achieve what I would have wanted.

Would I have taken it seriously if I had been told it was in fact a real option? I don’t know. I can’t imagine. It does make me glad for people today who are inevitably more aware of it than I was then.

At the time, however, I simply never seriously contemplated the possibility. I poo-poohed what my friend said and forgot about it. Even as I continued to yearn.

Next Week: My Life as Brittany York.

(Recurring) Notes on practical matters

This newsletter is a part of Confessions of an Autogynephile, an ongoing memoir in the form of a Stack of Sub essays (with occasional bonus politics thrown in). At least for the foreseeable future, this newsletter will post once a week on Wednesdays, and will be free.

If anyone wishes to contact me, I am reachable by email under the handle YorickPenn at gmail, and am on twitter as PennYorick (the reversed name was Twitter’s doing).

At the moment I am known to no-one, having been just (re)born as poor Yorick: so there is no one to promote this newsletter to.  (For what I rather hope are obvious reasons, I will not send a link out to my friends and family!)  Therefore, if you know anyone who might find it of interest, I would be grateful if you would send it there way.

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Since I just found myself in a big argument with a lot of people who didn’t like the word “autogynephilia” (because they, unlike I, think it can’t be stolen away from Blanchard’s specific theories and repurposed for more general use), I should perhaps remind the reader that I use “crossdreaming” to mean the general phenomenon of fantasizing and dreaming about being the opposite sex, and the term “autogynephilia” (and its opposite, autoandrophelia”) to mean specifically erotic fantasies about being the opposite sex. All autogynephiles are thus crossdreamers, but not all crossdreamers are autogynephiles. My crossdreaming has been centered on, but not limited to, autogynephilia; the incidents in this essay (particularly the first) are some of the clearest examples of that, given the age they happened.


"For heaven's sake, Alvie, even Freud speaks of a latency period."


I even had, at the time, a girlfriend of sorts, although I don't think either of us ever used the term.  But we went on a number of dates, largely going to movies at a local theater and wandering around the city afterwards.  It never went beyond the chastest of kisses.  We broke up (not in any acknowledged way; we simply lost touch and I didn't see her any more) when I switched schools the following school year. But in a very real way, this was the only girlfriend I ever had until, years later, I began dating the woman who is now my wife.


Though that sort of childish that even adults can have: how many times as an adult have I had a similar oh-I-know-it’s-just-a-fantasy-but-still… moment?


The fact that my birthday was, in fact, on a Saturday that year (I just checked) helps reassure me about the correctness my memory.


He came out to me two years after I berated him for saying he “tolerated” gay people, since (I, a liberal, pointed out) by what right did he arrogate to himself the superior position to pass judgment, even a favorable one?