Taking photographs of yourself while cross-dressed takes a certain amount of nerve. These pictures are evidence of the activity even after you have returned to male mode. This evidence is fine as long as the photographs are kept secret. If these pictures are shared, they become a public record of crossdressing. Photography can be a good way of ‘coming out’ – it allows us to show a family member or friend a depiction of our “other selves” without presenting her in person.
Taking good photographs are challenging at the best of times. Presenting our best looks can be difficult even when not dressed . But if the urge is there to show our girly selves off, we will find a way.
Most cameras have a self-timer, which ticks down until the shutter clicks. This gives around four to ten seconds to ‘transition’ from photographer to model, adopting a swift pose. This can be a fun, and highly addictive, way of obtaining images. Left to one’s own devices, hours can be spent changing clothes for varied pictures, making the best of what might be a rare and stealthy session.
Years ago, in the early 1990s, I never dared photograph myself cross-dressed. My feminine self, who I now refer to as ‘Polly’, was at the time a nameless and ephemeral being. She only existed in the moment, seen by myself in a mirror or by others on an occasional night-time stroll. I had accepted my cross-dressing, was not ashamed of it, but felt unwilling to document it just yet.
However, as I embraced my girly side in the mid to late-1990s, a parallel interest in trans-photography was equally difficult to resist. My attraction to trans-photography has ebbed and flowed over the years, much like my interest in crossdressing. After all, if cross-dressing is more of an activity than a lifestyle, photographs are both an archive of one’s activity and an achievement in themselves.
In 1996, my first trans-pictures were taken on film and, subsequently, needed to be processed. Since I did not want these pictures mixed with unrelated strips of negatives, I felt the best way option would be to shoot a whole roll of film dedicated to my dressing. If the results were awful, the whole lot could be junked without any real loss.
I waited for springtime sunlight to fill my home, then posed by windows using a self-timer. There was also a shared garden, which was a riskier prospect. But I donned a cute outfit – a summery floral dress with white tights and pink shoes – then threw a blanket on the grass and snapped myself relaxing.
The images displayed two undesired truths. Not only was I a male, I was hardly relaxing. Seconds later, terrified at the thought of discovery, I was folding the tripod and dashing upstairs.
Having taken thirty-six shots, I had to have them developed. What would happen when I collected the pictures? Would a lab technician giggle, would sirens go off and a klaxon yell, “Tranny alert!”
Excessively cautious, I sent the film to a postal lab at the far end of the country. Whatever they thought, I wouldn’t know! A week later, the pictures came back. No trouble, they had passed muster. Any good ones?
Tentatively, I peeled open the envelope. Not too bad I thought. There were a few bad poses or poorly framed efforts, but also some rather charming images. The garden photo was the best, even if I was a bit too far from the camera. It was odd to behold the pictures as a male, seeing myself as a girl after the event for the very first time. And of course, the photos would last. There would always be a version of my girl-self as long as they existed, whether I cross-dressed again or not.
Later, I bought a compact camera with flash that was great for more casual images. As I came out as a cross-dresser, I would have it available for party snaps when it was handed to some stranger. Unfortunately, these shots were often badly framed by eager but less than proficient helpers. I often wished I could be both the photographer and model, able to see how I looked through the viewfinder.
One good trick is the mirror image, something fairly easy to frame. One can shoot oneself clearly taking the photograph, or move the camera carefully away from one’s eye while retaining the composition. Pictures snapped in mirrors or shiny shop windows have a special magic, putting the viewer in the head of the trans-photographer. We can see the subject as if gazing back at ourselves, becoming both the subject and the viewer.
I still love using film, but digital imagery has massively enhanced trans-photographic possibilities. While one cannot be in two places at once ( photographer and subject) – digital photography offers the ability to take many pictures and chose the favorites.
Seeing the photos of other cross-dressers has encouraged me to expand background options, sometimes in corners of my home or against drapes to give a more neutral background. Pictures can also be cropped and collaged in a creative way, and I have learned far more about photo editing while taking such images than any other kind. They have also been a comfort when I have been unable to cross-dress, but wished to visit my alternative self. She will always be there if I cannot be her, fashionably framed, preserved in pixels or photographic grain.
I was introduced to black and white printing a long time ago. The second reel of film I processed was pictures of me in women’s clothes. Gosh it was so exciting. I hid everything in the sealed box that should only be opened in a dark room.
Sadly I lost the best ones.
That progressed to mail order colour printing.
And that was my second discovery. My future wife found a negative strip of a girl in stockings on our bed!
Digital is such a godsend for girls like us.
Discovery though can be catastrophic.
@Sandra Roberts Thanks for that, good you could take pictures even with a few alarming moments!
Hi Polly…Oh wow…thanks for your piece on photos. I’ve a newish love of modeling, just recently. Your love of trans photos is something I love to know I am not the only one…(as if). My “now" gf got me into trans modeling… I love fashion sooo much via my pinterest boards, it’s catching. I followed your story with excitement! Everything you describe is what I’ve come to love & live each time new clothes arrive, we imagine some ideas, this after early concern about 1 or 3 pics whereabouts, I bet I’ve 25,000 now. I could careless. Many are on… Read more »
@Kyra Marin Thanks, this is quite inspiring. I am looking at how to get more out of photography at home.
Anna x
Just love it! Keep writing on this, it’s so lovely to see ideas on how girls can get results from gradual experimenting! Super stuff. big luv, kyra
@Kyra Marin They may also be a couple of outdoor photoshoots for me too. We’ve got a couple of good locations in mind, just need to work out timing as they will be weather-dependent.
Anna x
@Anna Redhead Oh, outdoor, is fun stuff! Hope it co-ops, look forward to news! (seek Gothic-like places to shoot; and access certian “very large" homes of friends (as they shut down their inside sec. cams!lol). Nice to have privacy when wished! luv, Kyra
I’ve certainly got some locations with fantastic potential
@Anna Redhead Thanks, Anna. One way I am exploring is doing shoots as a kind of character – secretary, schoolgirl, etc. Context makes it easier to choose look & locale or backdrop.
@Polly Jocelyn I did a shoot recently with me as a bride which was a lot of fun. I’m looking at a location using one of the many ruined buildings in our area, also a seafront art-deco building with period dress style.
Seafront – I think Worthing and the shelters along the prom would be brilliant.
@Anna Redhead That sounds a good idea. Of course, real wedding photos are often done with the couple away from the church and reception too.
@Kyra Marin Brilliant words, Kyra, I think you need to do an article. All my online pictures on this site show me in my 40s & 50s so I don’t have the advantage of youth, just clean-living to remain fairly pretty!
Thanks so much, Kyra, you should do an article too (having read your profile now) – you have great insights & experiences!
Aw…merci for the kind words…I’d like to. My gf runs the camera, taught me about lighting; involved more in the process now as video takes hold
Love your outings, in “locations", is in ways the coolest and a genre, of situational spontaneity! So fun.
She, reloads pics with backgrounds: castilles gothic era, etc 🙂 Incredible adding of context, the forsight of production, & creativety. My bad, it’s so nice to talk you as a video-photographer. Luv, Kyra
Nice to hear this, Kyra! I have written an article about my 1998 Halloween, first ever X-dressed, but need to do a new picture for it. So am planning a creative photo-shoot soon, kind of simulating the past as I took no pictures – best wishes, Polly
I wish I’d saved some of the non-digital pictures from way back when, and very much regret purging them along with my clothes. Who knew that “never again" meant “this too will pass!"
@ek01 Even actors and comedians get photographed dolled up and are not necessarily TV or CD. So no shame in keeping pictures
”Crossdressing is more of an activity than a lifestyle.” I totally believe that Polly. I realize some of us girls on here have deep seated callings to be female 24/7, or as much as possible. But for me and many others I do believe it’s an activity we engage in from time to time. Much as I love to visit, I don’t want to live in the pink fog full time. And it’s definitely all about the pictures! Since coming back to this cult of Crossdressing a second time in my retirement, it is so much more enhanced by the… Read more »
@Grace Palmer Thanks for those interesting thoughts. It’s odd sometimes to have fun doing pictures then, as a man, tweak and Photoshop them as if now becoming some tech guy detached from the whole thing. It’s a kind of art, though of course the actual dressing is still the most fun part. Oddly, too, when we die we shall leave our girl selves in some form, no less permanent than our male memories. Perhaps more so!