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Crossdressing Photographic Evidence

by Jessica De Leon on July 31, 2010

Although my cross-dressing career has spanned about 20 years, there is no hard evidence to confirm this aside from my colorful testimony. This is probably for the best, as my early time in drag was nothing to be proud of.

As a teenager, I always wished to dress up and take pictures of myself, but the fear of actually having film developed at the drug store made my blood turn cold. This, of course, was the era before digital photography. This leads to the conclusion that once I got a digital camera, I’d go nuts with the “femme” pictures, right?

Photo Albums Full of Crossdressing?

One would assume that within a few days of acquiring their first digital camera, a cross-dresser wouldn’t waste any time in snapping shots of themselves en femme. This is probably the case most of the time, but for me it was much different.

My mother bought me my very first digital camera (HP) for Christmas 2001. She knew that I loved taking pictures and thus helped usher me into a new technological age. I immediately made use of my new toy taking pictures of my family, my pets and my house.

The possibilities began swirling about my head, and I began finding another cool use for my camera — taking pictures of myself before I headed out for the day. This way, I would get a better look at myself and also record what I was wearing that day.

A cross-dressing photo shoot was something I considered, but because I lived in a house full of guys this was a no go. Thus, my first pictures in drag would not come until the next year, when I moved into my own apartment.

Shame & Purging of Transvestite Pictures

Between the years of 2002 and 2004, I know for a fact that I did attempt to snap some early images of Jessica, but I don’t have good memories of this. Why? Well, because I promptly deleted them, as this was still the days of feeling embarrassed about my feminine persona.

Of course, when I reflect upon this, I realize that there was no reason for me to do this. The digital photos went straight from my camera to my PC and could be easily hidden in a protected zip file. Alas, my frequent purging was not limited to clothes. My pictures also fell victim to this heinous action.

A New Day

As you may have guessed, my wife was instrumental in producing the very first “full femme” pictures of me. Full femme, as I define it, is clothes, wig, bare face and makeup. But before this, we had a couple of shoots where I sported my facial hair. I still do have these in a safe place, and they will likely never see the light of day — though I do look at them every once in a while.

So here it is, from April of 2005, Jessica’s first ever professional-type picture.

Looking Back

I would have liked to have some photographic evidence of my earliest days as Jessica, but it will be okay. Do you still have any of your early drag pictures? If so, what feelings do you experience when you view them? Do you feel pride, shame, happiness or something else?

One thing’s for sure, digital cameras were probably one of the best inventions for cross-dressers. Ever.

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{ 9 comments… read them below or add one }

deja true August 5, 2010 at 9:29 am

Well, the answer to taking pictures in the pre-digital age was to sign up for photography classes. I spent hours in the dark room at school, late at night, developing and printing black and white prints. Still have a few arty 8X10′s (that, of course, never showed face just in case anybody else ever ran across them … lol!) :D

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Nathalie Landree August 5, 2010 at 3:12 pm

My earliest recollection was when I was 11, and my mom foraged through my schoolbooks only to find some pencil skeches of myself in southern belle dresses. The look on her face was priceless, all the while terrifying. and I think that’s were the same started. I was too scared to grab my dad’s Polaroid . ….but Polaroid was what most CD’ers used.

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Rebecca R August 5, 2010 at 4:02 pm

I’ve still got some ones of my high school days, but then, I’ve only been out of high school for 5 years. When I purged my clothes the first time (about 2 years ago) I did not purge my pictures which were on Photobucket. I think that I forgot at the time and also I know that I forgot my password for the longest time.
A lot of my pics I really don’t like, but that mainly has to do with the fact that it was my first time in makeup and my stash of clothes was extremely limited as well as the fact that I didn’t like the way I looked back then. The pictures I have are of my first purchases, which came from the clearance area of Target. Although I don’t have as much of a timespan as many individuals (I’ve been crossdressing for about 8-10 years), I can tell over the years I’ve progressed in my focus, knowledge, and interest in crossdressing.

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Leslee August 6, 2010 at 12:11 am

My cousin made me up when I was about 16 and took pics. They never turned out, how disappointed I was. I always wanted to have someone take my high school graduation picture and add some feminine touches to see what I looked like but never followed through. Funny how these things bother you later on in life and wish you could have done things so different if one had a second chance to do it again. Still had the cloths but no place to go.

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Lynn Jones August 6, 2010 at 3:48 pm

The only ones I deleted where the truly iffy ones where I’ve got my eyes closed, or I’ve not positioned the camera properly. Some are truly awful – in terms of outfit (bad skirt or iffy wig choice), but I think you’ve got to start somewhere and learn from your mistakes. At least I hope so :) I’ve not deleted them as they are a part of my tranny history.

Nice piccy BTW.

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Penny August 6, 2010 at 7:21 pm

I’ve only recently started taking pictures, but I’ve never been a very visually-oriented person. I’m using it more as instrument to see where I need improvement. Unfortunately, I need improvement in most areas. :/ And I’m definitely thankful for my digital camera. It never would have happened without it.

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Tanya August 8, 2010 at 12:04 pm

Technology is a wonderfull thing yes and Photoshop is a great tool, whenever
im not happy with a pic and its one that cannot be redone for whatever reason into photoshop it goes lol.
Hwever i always keep the origionals just to remind me of what it actually looked like.
Tanya

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stephaine kayleen delight(glen) August 8, 2010 at 1:52 pm

when i started to cross dress there wasnt much info out there for me to use and my generation really had it tough because all the info out there was bad cross dressing was a dirty word and if a person did cross dress then that person was queer ( for give me for useing that word but that was what we were called) i had a mother and father that beat me when they caught me dressing up and from that point on i had to be very carefull, i went throught two wifes and four kids because of my cross dressing, so at the ripe old age of sixty my present wife of 22 years as of today , does not mind me dressing up she even buys me clothes and make up etc, but today there is still a lot of bigotary out there. and cross dressing is mild to other things that people do!!!!! good luck to all that is into crossdressing and it was my generation that started to change the way people think of us.. love to all stephaine

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Julie M Shaw December 26, 2010 at 6:56 am

I had a Super 8mm Sound Movie Camera back in my teen years, and I shot lots of Julie footage. But alas, the urge to purge sent all of that film into the trash at various times. Now the only “record” I have of that time is – - – my memories. But you know what, the colors are more vivid and the excitement more thrilling in my memory than I’m sure it ever could be on film.

Julie Michelle

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