How does it feel the first time you dress as a woman?

[Sinead]

So tomorrow, I have my makeover, I've bought female clothes to wear and I will try on a wig and have my makeup done (basically be a woman for the first time). But my gender dysphoria has magically disappeared over the last couple of days - making me confused about my gender identity once again.

I was just wondering what it felt like for everyone the first time they dressed as a woman? I'm not expecting everyone's first time to feel the same, but I would like a rough idea of how it feels, I'm struggling to work out my gender, so I'm using tomorrow to see if I'm actually trans or not

[JessiCalypsoƸ̴Ӂ̴Ʒ]

So tomorrow, I have my makeover, I've bought female clothes to wear and I will try on a wig and have my makeup done (basically be a woman for the first time). But my gender dysphoria has magically disappeared over the last couple of days - making me confused about my gender identity once again.

I was just wondering what it felt like for everyone the first time they dressed as a woman? I'm not expecting everyone's first time to feel the same, but I would like a rough idea of how it feels, I'm struggling to work out my gender, so I'm using tomorrow to see if I'm actually trans or not

The first time I wore feminine attire was when I was in elementary school & I played "dress up" w/ my baby sitter's daughter, & I remember it just feeling RIGHT. Whenever I wore girl's - & later women's - clothing, it brought out the real me, the girl I always was inside. I behaved femininely, & I felt feminine... & HAPPY!!

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[Lynne]

Gender dysphoria sometimes comes and goes and that can really confuse the issue, but usually it's not something that disappears for a long period of time. Don't be fooled by the absence of it, it doesn't necessarily mean that you are not on the right path.

For me it's difficult question to answer about my first time because it was more like a gradual process and I have to think about what constitutes as my first time. If I have to choose I would say that my first real outing as a woman was when I visited another trans girl in another city which was 2 hours away by train.

I already had long hair but did not have much clothes and there was nothing like a makeover, just my assumption that if people thought I was a girl even when I was trying to be a 'man' then maybe I'll pass if I wear more feminine things.

I was really tired because I was after a night shift with no sleep. I had to change in the storage room of the garage to make sure nobody sees me leaving at the front door dressed in women's clothes and high heel shoes.
At first I was really nervous about walking on the street in broad daylight as a woman but when I realized I was late for the train I had to concentrate on getting there as fast as I could, the next half hour was an adrenaline rush for sure. I got my first real life lesson on what's it like to be a woman when I had to walk 2 kilometers in high heels quickly on bad pavement to reach the train. All that because I wouldn't take the shortest route to make sure my father's co-workers wouldn't see me.

The train was full with college kids and I had to walk up and down on almost the whole length of the train to find a place to sit. So everybody there saw me and I thought that they will eat me alive when they see me but nothing happened.
After a I while I started to relax and enjoy the fact that I'm traveling on a train as a woman and nobody seems to have any problems with that.
When I got to my destination we had another journey ahead to reach my friend's flat and even though my feet hurt like hell by that time and I was really tired, I got eased into the feeling of "I'm just another woman in the crowd" pretty quickly which felt great and somehow natural.
People's reaction towards me changed. They did not see a confused and confusing looking guy but just another girl. That made people a lot more comfortable around me and in turn that made me more comfortable in my own skin as well.
In the next few days we went on a shopping spree in the city and it was like a dream come true. It was a wonderful experience and after some time it was even a little frightening how natural everything was because I knew I had to go home in a few days and be a guy again.

[ToriJo]

I just did that this weekend. Previously I've dressed androgynous or partially (I.E. no makeup, so beard shadow was obvious, or only in a very safe place like my therapist's office).  I forced myself to do some routine shopping.

What did it feel like?  Scary as all.  But frankly, nobody did anything horrible, and I got no more than one stare while out.  I dressed pretty casual and conservative - jeans, a feminine but not frilly or sexy top, a pink cap to cover my way-too-short hair, makeup that might as well be stage makeup to cover my beard shadow but done as much as possible to appear natural.  I definitely wouldn't make all the guys do a double take or win any fashion awards!  I was kind of going for "don't stick out", although I'm sure I still did and I'm sure I was anything but passing.  But as awful as I must have looked, nobody said anything.

What got me through it, and even smiling once I finished, was that I reminded myself: Nothing bad is happening, and this is basically the worst you'll ever look and feel dressed, it's going to be easier than this next time.

And how I see it now?  I'm making an effort to be myself every weekend going forward. It is so worth being myself.

[KathyLauren]

So tomorrow, I have my makeover, I've bought female clothes to wear and I will try on a wig and have my makeup done (basically be a woman for the first time). But my gender dysphoria has magically disappeared over the last couple of days - making me confused about my gender identity once again.

I was just wondering what it felt like for everyone the first time they dressed as a woman? I'm not expecting everyone's first time to feel the same, but I would like a rough idea of how it feels, I'm struggling to work out my gender, so I'm using tomorrow to see if I'm actually trans or not

Good luck tomorrow!

Being nervous the first time is normal.  I know I was.  But I very quickly discovered that no one particularly cared about me.  I looked like I belonged where I was and tried as best I could to act the same way.  If you dress like others dress and act like others act, you will blend in.

The dysphoria disappearing is normal and predictable.  No need to be confused about it.  It tends to reduce whenever you take steps towards transition.  If nothing is progressing for a while, it will come back.  Then, the next time you make progress, it will reduce again.  Right now, you are taking some significant steps forward, so you are getting a major reduction in dysphoria.  Enjoy it while it lasts.

[Tammy Jade]

Like most people have already said. Being nervous was my big thing...

Realistically something you will notice quite quickly is most people are to busy in their own world to even notice.

And everything else (ie confidence) comes with time

As someone else said as well, even with the nerves it felt right, and it was that feeling of rightness that kept me going and not turning around in the carpark.

Good Luck and I hope it goes well.

-Mara


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[SailorMars1994]

A mixture of nervousness of ''wtf am i do'' and sweet euphoria of ''omg i am doing it!'', my first day out to the word was in May 2014 (excluding halloween 2007 when i dressed up as a girl) .. and omg, just recalling that day gives me the fuzzies

[AnonyMs]

The first time I wore female clothing was before I knew I was trans and I felt truly awful. I figured it wasn't my thing. That might have been one of the biggest mistakes in my life as it turns out it's dysphoria and I didn't realize it until decades later.

So tomorrow, I have my makeover, I've bought female clothes to wear and I will try on a wig and have my makeup done (basically be a woman for the first time). But my gender dysphoria has magically disappeared over the last couple of days - making me confused about my gender identity once again.

I usually find it goes away when I take steps towards transitioning, and what you're describing would be typical for me. It always comes back though.

[DawnOday]

It felt like a seven year old asking Mom to dress me in Sisters costumes and makeup. I felt as pretty as my sister who was twelve at the time. That was 59 years ago.

[Dani]

I cross dressed a few times when I was much younger. The feeling of my genitals in tight elastic girdles was uncomfortable. I have rarely crossed dressed since.

For me, clothing was a minor part of my transition. My transition was driven by my personal need to BE a woman.

Today, the clothes I wear are usually shorts and t-shirt, but sometimes I do dress up. It just feels natural.

[FinallyMichelle]

Amazing, terrifying, best day of my life up to that point. I knew that I was nowhere close to passable and that my dysphoria would no longer let me present as male so I had to but I was afraid.

Turns out that it wasn't that bad, there were a few stares nothing more. What is that quote?
Life begins at the end of your comfort zone.

[MollyPants]

I felt absolutely perfect the first time. Like everything was the right way round. I spent so long swinging the dress from side to side.

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[Charlie Nicki]

First time was in Halloween 2011 and I felt liberated and happy. Being able to act as feminine as I wanted to.

As others said, dysphoria comes and goes. And it can go when you are doing something to ease it.


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[noleen111]

Amazing and exciting,,

My first time dressing fully up was an amazing evening.. up to that point i worn pantyhose, even a little cheer leader skirt... but I had never actually dressed fully as a woman,

I wore blue long sleeve dress which down to my knees, with stocking and heels.. I wore makeup and a wig with clip on earrings... all firsts for me.. I even wore a bra with forms (home made made from bean bags) for the first time that evening. I shaved my legs for the first time that evening.

The evening was so magical, a good female friend helped me get dressed and she applied my makeup... we had a ladies dinner party.. it was so fun.. the worst part... was when it was time go back to boy mode.. I realized that night that I might just be female at heart...

[Sinead]

I echo what everyone else has said, it feels completely natural,like this is the person I am meant to be. The makeover was amazing, the woman was so understanding, I love my wig. I'm out in public, I've had plenty of people looking, but I don't care, I feel like myself for the first time in my entire life

[Roll]

Well, I haven't gone out in public yet but my first time I was really, truly dressed was amazing. It just felt right. Just over a month ago actually, so not too long. A lot of my confusion and fear just instantly evaporated, and I immediately attended my next therapy appointment (online, so not technically in public) dressed which felt even better. It was just so... natural, so comfortable, and made me feel so much more positive about myself. I didn't hate looking at myself in the mirror, and I would find myself spending 30 minutes just obsessively combing out my wig. I've never looked at myself that long before in my life.

[Angela Drakken]

I was 17 or so, I'd borrowed some clothes from some of my gal pals and went to Yorkdale mall in Toronto to make a day of it. It was pretty great, until I guess I passed TOO well and some creepy suit stalked me around the mall confessing I was 'the prettiest goth girl he'd ever seen' and offered to buy my lunch, my books ect. I tried explaining to him that I wasn't QUITE what he was looking for, and when he tried to check (by grabbing for my crotch) I had to bend his arm in ways its not supposed to move and put him on his face.

I ran crying back to the bus terminal, as this obviously ended my trip right then and there.

Scumbag had a wedding band on too..

Later, I was much more bold, going to classes and such.

[RavenMoon]

My first time was on Halloween back in the 80s. It was exciting and a bit scary!

Funny moment was me talking to my drummer's sister, whom I was pretty close with, and she had no idea who I was! lol


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[Thea]

It's so liberating! I noticed a definite reduction in dysphoria as soon as I determined to dress in public. It only gets easier. My first time was on Halloween several years ago. I no longer limit myself to one night a year and go out regularly.