Just How Happy were you the First Time in Girls Clothes

[Robbiegirl]

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 ?dresses.jpg1970s.jpg

[Alice Torn]

"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.

[DIANEF]

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.

[Jaylyn]

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.

[docrobbysherry]

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

[Aleca]

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.

[sara66]

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

[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

[Alice_2014_B]

I felt pretty good when I first fully dressed up!

[Janine cd]

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.

[Robin777]

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.

[DelilahGurl]

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

[Dana44]

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

[Vintage4sarah]

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.

[sarah_hillcrest]

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 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.

[irene9999]

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

[Ressie]

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

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.

[BrendaPDX]

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

[Angie G]

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

[NicoleScott]

Happy yes, but mostly very excited.

[LydiaL]

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.

[Chelsea B]

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.

[BLUE ORCHID]

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

[NancySue]

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.

[Sallee]

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