Just How Happy were you the First Time in Girls Clothes

I was the shortest boy in every class I was in till high school . The good news was that by about age 12 my sister older than me and younger than me were about the same size . I will never forget the day they were all out and I put on my sisters new Mini dress and OMG ! It fit ! I put on one of her hats and looked almost passable Fun and funny. Then before I knew it I was into her new lacy training bra and bikini panty and it fit ! I looked silly but was having fun . Ended the dress up party wearing both of their new Mini tennis dresses and ruffle butt panties.

Thank god their were no hidden webcams back then ! LOL ! After that I was hooked !

What was your first real happy moment when something fit you pretty good and you looked and felt more girly than expected ?Attachment 283222Attachment 283223

"Borrowing" my sister, and mom's hose, and other clothes, was exhilarating , but i was so nervous and scared i would get found out! I ruined my sister pantyhose, and iimagine she guessed what happened. My mom did not say why, but she tried to get me to see a "shrink". It was sheer delight, but a t the same time, i felt very ashamed afterwards.

For a couple of years I had been wearing various items of my mums and sisters underwear, but one day I had the house to myself. I knew my sister had a new dress and I really liked it, so I tried it on (I was 15 at the time) and loved it. I felt so 'girly' in it I knew I had to do it again, and again.....The rest is history.

I guess that would be when I was around 12 - 16 I loved when my parents ran into town because that's when I would play in moms hose, heels and makeup. Those smooth old girdles, silky underwear and thigh high hose held up by garters. It just didn't get any better than that also could be that I was reaching my puberty. All this together was the perfect set up to feel very girly.

First time was in my 50's. The feeling was so amazing I promptly forgot about it for about a year!:straightface:

My first time, as a teenager it was like Wow!, Very erotic feel. Another first time-out of the closet, I felt freaked out, worried about my safety while feeling erotic at the same time. Attitude changed as I went out more.

I don't remember how I felt the first time I was 4 or 5. I do remember how exited I was when my sister got her first training bra. I was over the top, I faked a sick day just so I could dress up. Good times!
Sara :D

I am trying to make this thread a bit different than YOUR FIRST TIME OR THE FIRST THING YOU TRIED ON. Trying for that moment where it kind of all started to come together

I felt pretty good when I first fully dressed up!
:)

The first time was when I was 11. I tried on my mom's slip and nylons. It was a fantastic experience. The feeling of the material against my body was incredible. Soon after I dared to try on her panties ,girdle and bra. More excitement. Finally, I dared to try my mom's makeup. It was at that moment that I knew that I would never be satisfied unless I could dress totally as a woman.

The first time I fully dressed with a bra, panties ,slip and one of my mothers dresses was the first time I really felt really girly and I was hooked for life. I did it when my parents went to visit my older brother. I had the house for a full day. Before that it was couple of pieces of clothing here and there. that is when I really started questioning my gender. It took me years to make peace with myself and accept that I would never be a girl.

Hmm.. my sisters bra and panties at age 12 I believe.
I just remember being very sad that I had to take it off.
Was a perfect fit. A perfect look.

D

Really cant remember it was so long ago. But one of the first time out with my SO was absolutely fantastic.

I remember the event in great detail even to this day. Since my youngest days, I had a fascination with nylon stockings and slipped a pair up my legs when ever the moment was right. Around 14 (?), I started to dog sit for a neighboring family and I investigated the lingerie draws of the mother and daughter who were close to my size. Bingo, there laid out before me was all of the clothing items and shoes that could fit me! Of course it was try on time that led to being completely dressed. That was exciting. The next day, I smuggled my sister's hairpiece and then after some work on myself, I fell in love with my image in a full length mirror as how I would look as a female from head to toe with even a touch of make-up. The sexual arousal was intense one I sat down and crossed my nylon encased legs.

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Originally Posted by Robbiegirl

I am trying to make this thread a bit different than YOUR FIRST TIME OR THE FIRST THING YOU TRIED ON. Trying for that moment where it kind of all started to come together

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I know what you mean. I tired things on as a kid, but I never really put it together. I didn't have a sister and I never felt right putting on my Mom's clothes. I used to occasionally dabble with her makeup, but always felt bad about it.

All through my 20s I would occasionally go through my wife's closet and try on something, but I always hated it, and somehow she would always suspect that I'd been through it no matter how careful I was.

It wasn't until this June at the age of 38. I went shopping and got my own clothes and makeup. I got a wig, and when I got it all together I saw a completely different person in the mirror. The words, "Wow, I'm hot," actually came out of my mouth. I feeling was amazing, like sliding down a rainbow and landing in a pot of gold.

I didn’t fully dress until my late 20s, got all my stuff online and was able to get heels and a wig for the first time. Needless to say it felt amazing and I got hooked to that feeling

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Originally Posted by Robbiegirl

I am trying to make this thread a bit different... Trying for that moment where it kind of all started to come together

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I don't think I had one particular Aha moment. I've tried on many different outfits, wigs and makeup throughout the last 15+ years. It's a work in progress that keeps getting better (other than aging). I can look back at photos I've taken and see what has worked best. Maybe then I say "aha" to myself somewhat.

I had picked up a dress at the Goodwill, smuggled it into my room, and put it on that night. It fit perfectly, I remember it had a side zipper, I had never seen one of those before, but when I zipped it up it pulled itself around my body. I was in shock, it looked beautiful, it hung right, and had a nice flair when I twirled. I was hooked! Thanks for the memories, Brenda

I think the day I put on my first pair of panties and a bra. I was so very happy. :hugs:
Angie

Happy yes, but mostly very excited.

While trying on my Mom & sister's clothes as a teen I felt so sexy. Quite the alternative to this skinny (at the time), non-athletic nerd. But no dressing took place during college and married years.

It was after my divorce while in my early 30's that I rediscovered my feminine desires. Bought some clothes, but it was not until my first wig when it all really came together. That wig completed the change in appearance from guy to gal.

For me it all came together when, after months of panties and pantyhose, then bras and girdles, I finally fully dressed for the first time. I was an ecstatic moment! I was 15. From that point on, and to this day, I can only settle for fully dressed.

Hi Robbie:hugs:, It was 71years ago and I am sure that it must've felt wonderful although I probably didn't know why.>Orchid...:daydreaming:...

In my youth, the instant I was helped to put on my first pair of nylons by next door sisters playing dress up, “happy” wasn’t the first thing I felt. Happy came later as I progressed to dressing completely. With my wife’s support and help, I am now, very Happy.

I don't remember when the 1st time may have been but I was young. I do remember walking around dressed whenno one was home and saying to myself how happy I felt. Must have been early teens

I was really young the first time I put on fem clothes. It made me feel different, perhaps a little naughty.

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Originally Posted by Robbiegirl

I am trying to make this thread a bit different than YOUR FIRST TIME OR THE FIRST THING YOU TRIED ON. Trying for that moment where it kind of all started to come together

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I thought I had achieved that 'come together' moment with my wardrobe, a closet cd underdressing. Now I want a complete transformation including hair and makeup.

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.

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...

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....

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.

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Originally Posted by sarah_hillcrest

I got a wig, and when I got it all together I saw a completely different person in the mirror. The words, "Wow, I'm hot," actually came out of my mouth. I feeling was amazing, like sliding down a rainbow and landing in a pot of gold.

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The wig was it for me too. I liken it to plugging in the Christmas tree once it has all the lights on it. Although in my case, maybe more like plugging in Charlie Brown's Christmas tree, but it made me happy lol

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.

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.