It seems like everyone has done some kind of crossdresser timeline, except me. Not one to avoid a good ol’ bandwagon, let’s get this show on the road. A lot of these dates are estimates.
This is the earliest picture I can find of myself dressed up. I was at university at the time, but still living at home – it’s no wonder that there’s almost no pics from this time. I had a sort of defined style, insomuch as I remember reading how the goth community was very accepting about dudes wearing skirts, so I figured… I know! I’ll be a goth!
This also resulted in me hanging out with goth people.
One particular instance involved me going to a bar with some what-can-only-be-described-as-acquaintances, changing out of my pants and into a long, black, velvet skirt, having a few drinks, realising my bag was stolen, and then figuring out how to get home on the bus without anyone killing me for wearing a skirt. As it turns out, no one did – so, you know, bonus.
Ok so clearly, I was bad at this. Holding the camera is my then-fiancée-now-wife. This was the first time (I’m pretty sure) I’d tried anything resembling boobs. Notice, again, the stripy tights – I was super into those. I probably still have them somewhere. Also: black and white on black and white? Jeez. I hadn’t even really started seriously with makeup – the most I had done is smearing eyeliner over my eyelids and thinking maybe that looked ok :S
My first wig (shitty), nail polish for the first time (removed IMMEDIATELY), unshaven arms (NEVER AGAIN), no makeup, but a not-terrible outfit. Oh hey, and whaddya know – I think those are my breast-forms – finally!
GIANT GAP WHERE I TOOK NO PHOTOS
There’s a whole 2-3 years here where, as it turns out, I didn’t take any photos. I don’t really know why. I was definitely still accumulating stuff, desperately trying to push my own boundaries and doing things like taking out the trash at night wearing heels. We lived in a particular apartment which was reasonably nice, but yeah. no photos from then. Huh.
Hey, webcam! It was around this point where I decided I would make a website. I had no plan, no advice to give, nothing but a shitty layout and bad decisions. But, I suppose it was around this time I started to take things a lot more seriously. I already figured it wasn’t going away (I kind of work that out about 7 years previous!). But now I had for the first time in my life: a disposable income. Sweet :D I was obsessed with those earrings for a long time, and that god-awful sweater-dress. It looks good here, but yeah – god-awful.
I really liked this t-shirt. I actually wore it for a recent photoshoot, and it looked pretty good :D Hadn’t figured out foundation, or lipstick really…or eyebrows. Still in the webcam-era, for now…
BOOM DSLR COUNTRY. Eh. I guess that red thing isn’t awful. This pic, however – nightmare. Awful pose, unsure expression. Not-the-greatest wig. Still, clearly, work to be done.
Ah, lol – the first pic I ever took on public transport! This was me coming home from one of the first serious-pants instances of going out to a bar-or-something-while-dressed. I went to a friend’s house, got dressed there, and we went out to a few bars. Got back to her place and crashed, with the full intention of going back home in jeans. But when I woke up at like 6am (still in makeup) I thought…maybe I can do this? Skirt on, boots on, wig on… and a brief moment of hesitation by the front door before I say “Fuck it” and push myself out there. It’s not my place. I don’t have a key – now I’m just out on the street, dressed up, on a sunday morning. Made it home safely, so w00t :D
This is a better view of that outfit – it’s kind of… all over the place. A haphazard mashup of things that are basically designed to hide all of me. I’m still getting over that to some extent.
This… was a turning point. There was a costume-party at work coming up with the theme of “circus-freak” – and what better than a ringmaster/bearded-lady combo? I kind of went a bit nuts – BUT there I was, surrounded by lots and lots of co-workers, complimenting my outfit – a few jokingly mentioning that maybe I was a bit too good at this. Yeeeeeah.
…and then I did it again at another work party. Ok, this outfit was GREAT – apart from the really, really awful wig. I should’ve known better. I should’ve worn the longer one I already had, but nooooOOOoo I had to go for one that was consistent with the time period but made me look AWFUL. That’s ok. Clearly this was becoming kind of a theme with people at work.
And then something happened. I took this photo while dressed up at home, and it kind of floored me. It was like “Hey…that’s what I’ve been trying to get towards forever!”. I looked good. And I was SO FRUSTRATED. The number of people who I knew I could show this photo to was about 3 people. Here was this thing I was so proud of, but I couldn’t tell anyone. It was kind of heartbreaking. But. I’d made progress in recent months. People had seen me dressed up – maybe it wasn’t that big of a deal? With words of encouragement from my wife…I posted it to facebook… and got nothing but support. I’m out, baby.
This is kind of a milestone. The first day I dressed up to work. Wig/boobs/makeup – the works. No one said a thing. Nothing. It was awesome. Also kind of underwhelming. I’d spent so many years terrified of moments like this – the confrontation of people I knew with a new reality, and…nada. Zip. Why the hell hadn’t I done this already?! Imagine how much better I would’ve been sooner! Argh!
I started to get a bit more serious about my photos after that. This is from the first actually-trying-to-do-a-photoshoot shoot I ever did. Eyebrows are a bit weird, and lighting’s a bit off, but I look at that photo and I feel like I accomplished something :D
More photoshoots, better clothes. This may as well be called “THE YEAR I FIGURED IT OUT”. Figured out my style, figured out my makeup routine. Figured out how to take photos. Happiness increased to maximum levels.
I don’t really know if there’s much more to say. There’s nowhere else at this point I want to go (other than start getting lasered!)
2016’s a few months away, still. I should probably get to taking a few more photos :)
I enjoyed your timeline. How much you have change thru out the years. Good job. Can’t wait to see more story’s and pictures about your daily activity. :-)
I generally haven’t posted very much about my daily experiences, but I think that’s going to change soon :D
You are beautiful and deserve to feel good about yourself!
thanks! :D took some hard work, but I got there :) I think.
I’m just getting started …panties level.. Yet wanna desire to explore the feminine. Side
both your 5th and 7th pics are the best…and by the way, how did you make the website?
wordpress.org :) (also wordpress.com!)