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PG My Crossdressing Story!! xxx
How I got into crossdressing
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Hello all!

I wanted to share this for a while with someone, and what a better place to write it than here!

It all started when I was around 10, there was a fancy dress day at school, and my mum thought it would be good if me and my 2 brothers all dressed as girls.
I can't remember what they wore, but I wore a leopard print skirt, crop top and a little jacket. My brothers weren't really into the idea, but I even asked if I could wear makeup, so she put a little bit of lipstick. I was just thinking why not try something new?

After school, my brothers straight away went and got changed, but I decided to keep my outfit on. It was a really nice experience, especially wearing a skirt which looked cute and made me feel "free".

It was from that day where I really got into it. I imagine that is what kick-started it, as I'm sure curiosity would of got the better of me eventually.

Over the years, I started sneaking into my little sisters room to try on her clothes. She is  a little over 4 years older than me though quite mature, also I was fairly small for my age.
I remember one of the early ventures, I found Barbie bra and panties in her draw, they were cute, bright pink in some sort of fleece material, so they were kind of fluffy.
Soon I went for a full outfit - bra, panties, black tights, a skirt and a cute purple top. I  took them back to my room and just hid them in my bed, and when night time came, I carefully put them on when my brothers were sleeping. I got out of bed and went downstairs when my parents went to bed and put on a pair of stilettos. They were very small, so I didn't wear them for too long.
Looking in the mirror, I really liked what I was wearing. I enjoyed feeling girly and I loved the feel of the tights especially.

That went on for a little while, trying on different things as I did it. One day, I was wearing pretty much the same things and just enjoying myself wearing, when to my horror, my mum started to walk downstairs. In a panic, I ran to the bathroom and got undressed, putting on my own underwear. Knowing I couldn't just leave my sisters clothes in there, I walked out and just said "I found these in the bathroom". I can't quite remember what my mum said, although I know I was thinking "oh god!!"

That experience never stopped me, if anything it made me want to do it more. I liked the sense of danger as well as feeling girly.

Another little panic I had was I kept a bra and a pair of panties in my pillow case, I liked to wear them in bed sometimes and just put them in the wash when I woke up. Soon, my brother found them in there, though I just replied I wanted to know who keeps stealing my money so I hid them there to find out. He didn't reply luckily!

As I grew older, so did my sister and her clothes just got better. I found in her draws a Playboy bra and thong, which I did wear a few times. Didn't want to wear it too much as it was her best pair, and I figured she would get suspicious.
I also tried on a few dresses and put a bit of lipstick on for the fun of it. Oh the thrills!

I even wore her panties to school a few times, although I had to be careful the frilly top weren't visible, and made sure I didn't wear them when I had to do PE.
My final years of secondary school was at the time when I did have a girlfriend, so I didn't really dress up much. However, in the final years it was Christmas fancy dress. I opted for a fairy costume, which was a knee length dress with wings, and I wore a cute blue bra and black thong, which had at the back the design of a butterfly.

Although we separated months later, dressing up still remained fairly rare, mostly as I also had college. I did sometimes wear panties at home and wore my sisters corsets and skirts when everyone was asleep, and when my sister was out.

Soon I got back into it again, wearing my sisters stockings and suspender panties, and the usual cute bras, skirts, tutus and tops. I even tried to put on makeup, although found it very hard to do, so typically stuck with lipstick while I tried to learn about the rest.

Over the past 2 or so years, I have remembered trying on her big, pink prom dress, and oh did I love that! Also tried on a cute red dress and a blue, sailors dress.

Eventually I decided to buy my own clothes, and the first was a sissy tutu thong. The frilly tutu part was pink and black in satin.
I soon bought more panties, though just some really cheap ones to try it out. Soon I started buying nice lingerie - panties, thongs, stockings and a few bras. I bought a few cute nightdresses too, which I just love sleeping in!

More recently, I got a few corsets with matching skirts, as well as more sissy panties and other lingerie. A cute and silky black dress was also next!
Adding to my collection, I got 2 very nice babydolls with matching panties/thongs. That any my black dress are the things I love to wear the most... complete with some nice heels!

Post will hopefully arrive in the next few days to deliver more sissy panties and a leotard/tutu, which I just cannot wait to dance around in!!

Right now, I'm just wearing a big, cute pair of pink and very frilly panties. I just love the feel of them!

Soon I hope I will post pictures of some of my favourite outfits, though for now I hope you enjoyed my story. Feel free to ask any questions you have!

~hugs and kisses~ xxx
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Jennifer Funshine
While your post reads more like a diary entry I thought it was all very cute hun.
Never is easy retelling or even remembering our childhood memories or expressing our love to be frilly and feminine but here you've done a fine job. I can just imagine how thrilling your experiences were... I've had a few close calls myself! *giggles*

For future reference, such lovely reflections are really more suited to
the  "All About You" forum opposed to "Story-time."

~*Gentle Hugs*~
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Baby Butch

I read your story last night but for some reason I could not approve it. I tired 3 times but it did not work. I was going to suggest this could have been posted in Princess Diarys where true stories are posted. It is just fine here in Storytime.

 

I liked the growing up memories that ypu posted. It sort of reminds me of myself, although I was not as daring as you were. I thought the part about all 3 boys dressing as girls was cool. I see you are the one who liked it.

 

I occasionally dared to steal a pair of panties and wear them. I also liked leotards and pantyhose. My problem was they stretched a bit too much and I had to put them back. Never had anyone say it was me who did this.

 

Have a great day!

Baby Butch : )

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