My Life as Brittany York

Content notice: This entry discusses sexual fantasies (reasonably vaguely). It also has a picture which is

—in, I should say, a mild sense; nothing to extreme. But it’s there. (I put the letters “NSFW” in as a photo in the hopes that Substack will consider it, and not the actual NSFW image, as this post’s image to accompany the link.) Only proceed if that will not bother you.

My fantasies of being transformed into a woman continued after I graduated from college, although at this point they merged into another set of fantasies, brought upon by an entirely separate set of shames and desires, namely, the fantasy of being able to redo my college education.  I felt (fairly or not) that I had not learned nearly what I ought to have; and I used to fantasize about being brought back in time to an earlier part of my life, and being allowed to proceed forward from there.  These fantasies, I should say, were pretty detailed; I still probably have, somewhere on some disk, a list of the classes I would take (similar, but far from identical, to the list of classes I in fact took) were I to be able to redo college, carefully compiled from the course catalogs I retained from my college years, checking to make sure that the classes I wanted to move were in fact offered in the semesters I slotted them in and that the new schedule would still fulfill all major requirements.

Often these fantasies stood on their own: the regret about achievement (that central site of bourgeois transference for the sex drive) was, in its own way, at least as strong, if not perhaps stronger, than the regret about being someone who was not desirable, who could not be desirable,but who nevertheless, intensely, desired.  But they did stir.  So sometimes I would imagine being thrown back to the summer before my freshman year just as I was; sometimes as I would have been, in an alternate universe in which I was female.

(I have noted previously the way that the contingencies and specificities of history have shaped the history of my desires and fantasies.  I should perhaps note here the way that the very specific culture of science fiction and fantasy did so.  These concepts — being thrown back into my past, or into an alternate history — might, just possibly, have occurred to someone who was unfamiliar with those concepts, but certainly it is far easier to do so when those ideas are laying around in the public mindspace of the culture, available and ready to hand.  We are all the product of so many things — our personal histories, our place in global histories, our genes, our specific experiences, our desires, the history of our culture, the accidents which make up what part of each of those we happen to see — but each also affects, if only minutely, the other, just as the baseball arced to the outfield draws the Earth back towards it at the same time that the Earth, more visibly, draws it.)

These fantasies were complicated by the fact that I was, by this point, in a steady relationship, but somewhat less than you might think.  The main reason for this was simply double-think: I was able, and did, to put the current reality beside the fantasy and somehow will both of them.  But sometimes I would make specific allowances, too.  I would fantasize that I would be sent back to a particular time, and then, prior to the time I would (again) meet my now wife, be forced to engage in some amount of sexual behavior — forced, of course, so that I would not be (in the fantasy) being unfaithful by my own will.  Then I would meet her, on schedule, and we would have a lesbian relationship — that she was not lesbian seemed a comparatively trivial matter in which I was already twisting the laws of space and time and physics about in order to tidy up the frayed edges of my life and psyche.  If I could be transformed in sex and hurled through time, surely her desires could be rearranged.

Sometimes the fantasies were about doing specific sexual acts — sleeping with some quota of men (and yes, in the fantasies it was usually men) before I met my wife and settled down.  But, at least through my early twenties, far more common were fantasies of exposure.

These themselves were not new—as I wrote before, they went back to before I was ten. (For anyone who did not read the earlier entry, the earliest fantasy I can remember about being a woman was of being on television, and sitting casually so that the audience could look up my skirt.) But by this point the desires had shaped themselves to something more specific: I fantasied about being seen naked.  In particular, I fantasized about becoming (through time-travel) a woman, and posing for Playboy.

Playboy was, after all, pretty much the only porn I ever looked at (there were a handful of exceptions—at least one copy of Penthouse, a few pornographic comics, a magazine at a friends house, one or two other things—I’d guess less than 10% of the total, or even less than 5%, probably).  This would remain true until my early thirties, when we finally got a real internet connection at home (i.e. not just a dial-up) and I branched out.1 But it was true for well over a decade. So for me, erotic desire — that is, purely in the realm of desire, and separate from that of being a body in contact with another body — was wrapped entirely up in that magazine.

I buzzed at the thought that people might look at me the way that I, and so many others, looked at the naked women in playboy.  I lusted for that embarrassment, that exposure, that being revealed, as hard as I lusted for the models themselves.  (There was, I should say, always some of both, at least over any significant period of time; it was never wholly autogynephilia.  I wanted them, and I wanted to be them, and the two desires were hard to separate.)

And just as I was systematic in imagining what courses I might take in my fantasy do-over, I was systematic about when, precisely, I would go and try out and become a playmate of the month, the centerfold in the magazine.  I decided that (given various factors and timetables which were doubtless implausible, but by the standard of "going back in time and magically changing sex" hardly registered) that I would be the centerfold in the October, 1990 issue, displacing the real-life Brittany York.

(Brittany York, incidentally, was not her real name; it was a pseudonym adopted for posing nude, a common enough practice for obvious reasons.  Despite this (and I certainly learned it at some point), it never occurred to me until writing this chapter that I could have fantasized that I could literally be Brittany York, i.e. not that I could magically inhabit her body, but that my own, magically-transformed body could pose, but that I could use the same pseudonym.  But there was a reason that it never occurred to me: I, when I posed, would use my own name, since after all the exposure, the titillating embarrassment, was precisely the point.)

It's not that I particularly liked her pictorial, although I did like it.  Her centerfold was sort of eh, but then the centerfold was quite rarely the best picture of any of the centerfolds.  But in general, while I found her attractive enough — she was certainly what I would fantasize I would look like, brunette, a generous but not bizarrely large bust, etc — the photography was not quite as good as it was in various other issues: I simply didn't think the photographer (who was veteran Playboy photographer Arny Freytag) did a good job.2 It wasn't that I wanted to look like her: it's that I wanted to usurp her place.  And while she became one of my favorite centerfolds (I had a list, with five or six names on it), it wasn't because of the photography.

There was, however, one exception to this — one set of photographs (one can tell that they are photographed in batches, given locations and outfits) — one which, if the internet is to be trusted, were in fact from her playmate test, and thus presumably with a different photographer.  These were the images that I looked at and thought, most intensely, I wish that was me:

Two nude pictures of BY side by side
Brittany York, Miss October 1990—Yorick I. N. Penn, in his dreams. These two photos, by the by, are © by Playboy, and are used under the fair use doctrine.

It is hard to describe the sort of physical longing that that would be my vagina, photographed just like that is.  Wanting to fuck some beautiful woman is, by comparison, far more psychologically straightforward.  But the desire I felt — still, in some ways, feel — looking at these images is far more the former than the latter.  Some of the latter is there too: it needs to be, since so much of the desire to be her is in the reflected desire I feel for her.  But it is the be, not for, that is paramount.

Brittany York would not be the last model that I thought of as (in some way) myself; there would be many others. Indeed, it was not all that long before, thinking over my imaginary timeline, I decided that, given my age, progress through school, etc, trying to pose by October 1990 was a bit quick, and maybe I ought to imagine myself as usurping the place of Wendy Hamilton in December 1991. So she, too, became someone I would look at and think, I wish that was me. Indeed, sometimes I would look and think: that is me. So I would flip through one of Playboy’s newstand specials and, seeing either Ms. York or Ms. Hamilton, I would think, O, I’m in this one. Which in one sense was basically short for: if I had gone back in time, and been a woman, and posed, I would have been in this one. But in another sense meant: I wish that was me. And in yet another sense was letting my sight blur, the way you relax your eyes to see the hidden photo in a magic square, and seeing it, somehow, impossibly, as myself.

So no, Ms. York was not my first avatar in the world of nude pictures. But she was the first.

Next Week: Identity, Privacy, Perversion, and Public Speech

(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 (I don't know why twitter wished that backwards).

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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There probably is a really good, closely-observed social history of porn and how it wove into its users lives, talking about the sheer change in what pornography is like from, oh, WW2 to the present, through all the many changes and eras. Certainly my own porn consumption was very micro-era specific, and would have been very different if I’d been born either ten years earlier or later.


Interestingly, I found out while I was confirming some details (and, of course, looking at some images — I would never claim to read the internet only for the articles) that I was not the only one to think so.  A review of her pictorial that I came across (I swear, it had never occurred to me that such things existed although, as with the existence of a whole class of people whose desires follow patterns similar to my own, I really ought to have thought of it) said that "Brittany clearly deserves better".