That first time

[Jessica Brown]

Hello Ladies,

I got the opportunity to dress up for a little while today and while I was, i started to think about the very first time I wore something. My cousin and a couple of her friends were all about 16, we were in the mall shopping one evening,  and were in one of the department stores when one of her friends pointed at this dress and said “you would look gorgeous in this dress!” Well, I was pretty embarrassed at the time because a couple other folks I didn’t know heard it, and chuckled a bit as well. Even though it got me embarrassed, it got me thinking I wouldn’t mind trying something on… I text me cousin K and her friend a few days later and told them I was going to try on one of my moms bras when she wasn’t home…  They neither one believed me until I had text them a photo of me.. both of them were pretty surprised but really got a kick out of it… it wasn’t long and I was adding a dress and lipstick… They convinced me to dress as a woman for Halloween that year and many times since then, I would dress up when we’d all hang out at one of our houses. My cousins house was always most fun because her mom knew I was dressing up and always played along/enjoyed it.

Thanks to whoever read, I’d love to hear the story of your first time as well!

 

xoxo

jessica

• This topic was modified 2 months ago by Jessica Brown.

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[J J]

The more I think about such things, the more little bits of memory come back. No doubt there is selective memory involved, and after so many years a lot of them are not even accurate, but they are still fun.

So, I dressed the first time when I was somewhere around 12 to 14. It was definitely in my middle school years, and I only did it twice that I can recall. At least once it was full head to toe things from my mothers closet including a wig. At that time my own hormones were coming on, as were all the girls so we were developing both physically and emotionally. I remember loving the development of all the girls’ boobs, and sneaking a peek down their tops was always a goal of mine. I also remember them starting to wear nylons and showing off those lovely legs. I suspect that lead me to trying things own because I wondered if I had good looking legs as well.

I did not dress for many, many years after that. I had no desire to, nor even any thought of it that I can recall. It was pretty much a one (or two) off kind of thing. I put on a pair of my soon to wife’s panties many years later, and that has led me to where I am today.

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Stephaniewy, Stephie Terrill, Jessica Brown, Leah

[Anonymous]

I remember being really young and watching girls in my class start to develop

Boy, was I jealous when I noticed their boobs begin to take shape over the pubescent years.

I then decided to try on my aunt’s bra I found in her bedroom at my grandmother’s house.

Since then, I wanted to have something to fill a bra with.

Now that I had implants put in, the fun never ends

 

 

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Stephaniewy, Stephie Terrill, Lynda Jones, Jessica Brown, Leah, Arora Scott, Deborah Sullivan, Willa Rose

[Paula Here]

Hi Ladies

My first time I was home alone and went into Mom’s room.  Pulled on her marching bra and panties garder stockings, shoes, and proceeded to put on makeup.  I was 15.

I heard a knock on the door and then the voice of my best freind.  Frantically remove everything and wash my face.  Talked with my freind.  When he left put everything away as best I could.

It was several years before I tried again.  My girlfriend,  now wife, was over 18yo house to our selves.  She went to the bathroom and laying on the floor was her skirt and tights.  So on they went.  She came back in the room and told me my legs look good, now get my stuff off.

Next time was years later.

Those first memories sit fresh in my mind like they were yesterday.

Paula

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Stephie Terrill, Leah, Arora Scott, Willa Rose, Lynda Jones

[Wanda Ovahear]

Sounds like fun times, dear. A real treat to dress so much at that age.

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Jessica Brown, Stephie Terrill, Brittney Andrews

[Author]

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