I was really young the first time I put on fem clothes. It made me feel different, perhaps a little naughty.
I was really young the first time I put on fem clothes. It made me feel different, perhaps a little naughty.
At about 11-12 I was home alone and tried on one of my Mom's slips, it felt wonderful so next came the bra, panties and stockings. From then on any chance I had I was being girly.
I had the exact same experience/feelings as Janine at the age of 11. It is a small world.
I actually felt really good...it was beyond my expectations of what I thought I would look like. And as I get better at putting it all together the better I feel about me.
Life is too short to be boring...Alexandra
Before I started crossdressing, I liked to cosplay as Princess Peach in the privacy of my own house, but I definitely did not consider myself to be a crossdresser and didn't even know what one was at the time. When I put the princess outfit on for the very first time, I felt very happy.
Many years later in 2016, I received my first order of feminine clothes. When I put them on the first time, I suddenly felt very girly and feminine, and I realized that I was a crossdresser. I loved it so much and felt so great, like a new chapter in my life had just opened up, one that was already proving to be very exhilarating and exciting. I couldn't wait to purchase more clothes.
I was 5 so I really don;t remember. My 'Aha moment' was about ten years ago(I hadn't dressed for about 25 years at that point.) in the midst of a very dysfunctional and abusive marriage; I found a great feeling of normalcy and peace when I started dressing again. OK, a little bit of revenge, too because I was wearing my now ex wife's things...
I am Me and Me is OK!
Shelby
It felt really great, and it was releasing tension sensation lie nothing before.
First time I recall I was 10 or 11. It was my sister's cast off one piece swimsuit. I was hooked for life.
I haven’t every really fully dressed yet, I’m just hooked on panties. But I remember what exactly the pair of panties I tried on looked like. I was around 10 years old. They were my cousins and I was hooked ever since!
First time must have felt better than eutopia because here we are over 50 years later and I am still dressing and enjoying.
As a child it simply felt great. As a teen it helped me through puberty. In my 20's I realized that wearing women's clothing wasn't a phase. Then I found out that I wasn't the only guy wearing women's clothing but according to what was public guys that wore women's clothing were gay. I went to a lesbian friends marriage ceremony and met a few cross dressers that were straight like me. Years later with the internet I discovered that I didn't have to totally dress in guy clothes at work etc. I began under dressing and have been since.
Again, I don't know what my exact feeling was but I have been, I am and I always will be happy that the first time made me the person that I am today. A happy life long cross dresser.
Mmmm!
Not very happy at all.
I was four and dressed in baby clothes, shoved into a pram and given a bottle of milk to suck on.
Funny, I got used to it and even got to like it later. :-)
They even let me have flavoured milk after I complained....
Work on your elegance,
and beauty will follow.
I wore my mums underwear. I wore my friends sisters underwear, I wore my friends mums underwear. Girls I house shared with, I wore their underwear and dresses. I took every available opportunity to dress as a girl. I was like an addict. I kept buying odd clothes but then throwing them away. Finally I bought seriously. And I bought shoes. Shoes made me really happy, more so than I had ever expected. That was a surprise. My first pair completed my ensemble. Gloriously happy and super sexy.
Like the others who have replied, the first time I was dressed in a long-line corset and the pleasure and fascination was remarkable. I was very young, perhaps 5 or 6. I loved the feel of the silky facings, the tightness of the corset and the look of the shiny material.
However, the first time it all came together was much later when I was with some friends. They dressed me up and put on a wig and carefully applied makeup. They said I looked a little like Doris Day (gosh that dates me) and when I looked at my image in the mirror I was overwhelmed by what I saw. I was looking at a new person but one I felt comfortable with. I felt joy and also liberation. It was as if I had finally arrived at my true self.
Michaela
If you choose not to decide, you still have made a choice. - Rush
I wouldn't call it happy. First time was as a toddler, so I didn't know what I was supposed to be wearing or NOT wearing until my dad came home and made a stink that I was wearing one of my sister's dresses (mom dressed me in my sister's old clothes, supposedly to keep me from ruining my 'good boy clothes'). The next was a single episode when I was 4, when I envied all the attention my sister was getting when mom was getting her prettied up to go to school. I put on some of her clothes and went in and said that I was ready to go to school, too. Mom just got me back to being dressed normally, and we walked my sister to school. When we got back home, mom asked if I really wanted to wear her clothes, but in such a way as to imply that I should say no, so that's what I said.
The next time it was by the guy who molested me, and by that time, I knew that it was the worst possible thing for a boy to be girly in any way. The fact that he further used the knowledge that his little sister's clothes fit me perfectly as proof that I was supposed to be born a girl, left me in shock, and a bit of horror.
So happy wasn't a feeling involved in any of those episodes.
Some causes of crossdressing you've probably never even considered: My TG biography at:http://www.crossdressers.com/forums/...=1#post1490560
There's an addendum at post # 82 on that thread, too. It's about a ten minute read.
Why don't we understand our desire to dress, behave and feel like a girl? Because from childhood, boys are told that the worst possible thing we can be, is a sissy. This feeling is so ingrained into our psyche, that we will suppress any thoughts that connect us to being or wanting to be feminine, even to the point of creating separate personalities to assign those female feelings into.
For me, my happiness in girl's clothing was a slow progression.
I must have been may 4-5 years old, it was a school thing and we all went to a swimming pool. I don't remember the details, but I didn't have a pair of swimming trunks so at that time pools would have swimming trunks/suits you could use (of course they don't do that anymore). As luck would have it, they didn't have anymore boys trunks so they gave me a girls' swimsuit to wear. Maybe that I why I now have a serious girls' swimsuit addiction.
Later on I tried on my mom's panties, which then progressed to her shapewear (that is probably how my shapewear addiction started too) and then her dresses/blouses/skirts. My mom never used makeup, so at that time I never truly transformed into the woman I wanted to be.
I think when I was able to buy my own clothing that was when I was happy in girls' clothing. Fast forward to now, and I am extremely delighted to be Wendy given a chance.