Hey guys as many as you know I haven't transition YET!
I wanted to know when was the firts time you guys dressed up as girls or boys and who was the firts one to see you and how did they took it?
If you will like to share please I'm very curious about these. 

Nikki

The first day I dressed as a girl was my first day fulltime and my first day at Seminary.

Before then, I was getting ready by taking HRT, learning makeup, learning to relearn my voice and buying all the clothes. Before I went fulltime, I was androgynous.

I was pretty nervous the first day as Annah at school. Within the first 15 minutes of sitting through orientation, I was so nervous I threw up in the bathroom. That was on a Monday.

Then the next day I gathered the courage to wear a skirt where monday i wore a pair of slacks.

After that, it became completely natural.

I go androgynous (as far as that works) full time, but the first time I've gone out all girly was last Saturday. I was rocking the sunglasses and handbag with my friend Whitney, and it was totally awesome.

We got quite a few crazy looks but everyone was super nice to us.

I'd love to do it again, now that I have a decent haircut. I didn't realize long hair would be so difficult to manage.

Properly? About a month ago - I've done a lot of androgynous wear in my time (especially in my 20's) but last month I went clothes shopping in women's departments, got jeans, underwear, tops... and my girlfriend was the first person to see me in the whole outfit, which turned out well . Now I'm very confident about what I wear, and about going out and buying it. Of course, I don't present as very feminine, so it's less challenging than it would be if I were into more obviously feminine clothing and appearance - but I ain't .

The first time I presented as female was my first day of full time. I plucked my eyebrows and got my hair cut, and that was it. It was strangers who saw me first, walking home from the hair dressers, and the main thing I noticed was the absence of "what the ->-bleeped-<- are you?" looks which I'd been getting more and more frequently for the last 2 months at that point. I'd been on hormones for 6 months, but had no girl clothes. I went shopping a lot the next 2 weeks to expand my wardrobe.

I think I always dressed like a boy. For bio girls, though, nobody gets that as a flag.

The first time I went as male and used a boy name (really an androgynous street name, as I was a homeless gutterpunk at the time) was in the late nineties. I was so happy. It didn't last long though.

The first time I bound my chest and tried to act completely like a guy as an adult was I think less than a year ago. I was elated. I passed more easily than I expected, and everybody thought I was babysitting my little sister when they saw me with my daughter. I love my daughter and I'm proud that she's my daughter, and I'm absolutely not a teenager, but it was such a relief to be a boy and have people be so nice to me that the particular mistake made me happy.

I've almost always worn boy clothes because the only sibling I have is a brother, so the hand-me-downs I got were for boys.

I have a unisex name and I've looked androgynous for almost my entire life, but when I had long hair people almost always pegged me as female. However, the first time I got "mistaken" as a boy was in seventh grade when I still had waist-length hair. It seems I always had male body language/social cues.

When i was a young teen i always dressed as a girl because i had long blonde hair and wore my sisters hand me downs and i had no facial hair, but people thought i was being more than a hippy which i was so they put me in the local state mental hospital for wearing womens clothes. There i met a neighbor who was there for being gay. That was a long time ago back in the late 60's when being gay was a mental disease and being gender queer was even crazier. .. 

The first time I fully dressed with clothes, makeup, and wig I hadn't even started my transition. I was at my sister's house. It felt a little awkward but good at the same time. She was always supportive. That was also the same time I went out in public.

Me and my sister went to this nightclub. No one really said anything except the bouncer of the club who told me I should stick with male clothing.

I even took pictures which I dread looking at today.

The very very first time?  I was 5 and in a few weeks I guess about to get sent off to kindergarten. So I went and put on my sisters school uniform.  Not cool. I got the message loud and clear from mom.

First time out in girl mode was mid teens to sneak a walk around the block. First real time out in public was after getting my drivers license. That gave me freedom needed to leave town, walk the streets and hit up some stores. BTW this was the 1970's

The first to ever see me was my sister. She came home early one afternoon when I thought I had the house all to myself. After the two of us freaking out for different reasons and I finished crying and begging her not to rat me out, it was sort of nice realizing she had no clue whatsoever who that strange girl was!

Quote from: JoanneB on October 13, 2011, 05:49:22 PM
The very very first time?  I was 5 and in a few weeks I guess about to get sent off to kindergarten. So I went and put on my sisters school uniform.  Not cool. I got the message loud and clear from mom.

First time out in girl mode was mid teens to sneak a walk around the block. First real time out in public was after getting my drivers license. That gave me freedom needed to leave town, walk the streets and hit up some stores. BTW this was the 1970's

The first to ever see me was my sister. She came home early one afternoon when I thought I had the house all to myself. After the two of us freaking out for different reasons and I finished crying and begging her not to rat me out, it was sort of nice realizing she had no clue whatsoever who that strange girl was!

Now I'm really interested ... how did your sister react when the whole situation settled down? Was she supportive? Did she rat you out?

Kinda interesting story, first actual time would have been when my mom would dress me up when I was a baby. just don't know if it was true or not.

But my own self dressing was when my wife encouraged me not to hide it anymore.

Fortunately she never ratted me out. By that time mom had already found my stash of clothes twice and I was sent off to the shrink. Once my cover was blown my sister told me to go clean myself up and get changed. We didn't talk much. Just wasn't the way our family operated, the dysfunctional by product of alcoholic household. Basically she calmed me down, swore she wasn't going to tell mom, and ended with "No blue eye shadow".

After that day not another word was mentioned. Although I've come close to it twice now this past year

I dressed male even as a small child, except for the rare occasion where my mom would put me in girls-specific clothing. Around middle school my mom stopped buying me male clothing, which I didn't particular like, but had to deal with simple because I had no money to buy my own. But I always picked the more andro clothing. In my 20's I had a short stint of what I would call "cross dressing" simply because I'd tried actual women's clothes and wore some. Then I gave that up for awhile, but have since gone back to andro clothes from whatever department (mens or womens) as long as it looks good one me and I like it.