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Slumber Party Sissies by SissyDemi Slumber Party Sissies by SissyDemi
I found this little gem while looking through old floppies. I had done a half dozen captioned images like this, but only this one seems to have survived the last decade. (The time-stamp on the file is November 2001.)

Being caught spying on a girls' slumber party is a common crossdressing theme. Usually the transgressing boys are dolled up in frilly lace lingerie, but honestly ... How many young, teen aged girls are going to have that kind of sexy lingerie?* Hence the more real world sleepwear these girl-clad boys are showcasing.

Anyhow, I hope you enjoy this artistic deviation (pun intended) from the BLSB style.


* I had an older sister and while we did grow up in a slightly religious home, she never had anything like corsets and garters or teddies and merry widows until she was around 17 and well past slumber parties. She did have frilly babydoll nighties which I put to good use on occasion, but 99% of her sleepwear and underclothes were more mundane.
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:iconsallyane:
sallyane Featured By Owner May 15, 2015
love this cap
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:iconsissydemi:
SissyDemi Featured By Owner May 16, 2015  Hobbyist Digital Artist
Thank you. It is a very old one I did almost 15 years ago, now. Time flies.
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:iconiluvgreggsulkin222:
iluvgreggsulkin222 Featured By Owner Feb 17, 2012  Hobbyist Writer
do you mind if i use this photo for a story.
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:iconsissydemi:
SissyDemi Featured By Owner Feb 18, 2012  Hobbyist Digital Artist
Go for it! :)

Let me know when you do so I can read it!
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:iconiluvgreggsulkin222:
iluvgreggsulkin222 Featured By Owner Feb 18, 2012  Hobbyist Writer
i deside not ot write a story
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:iconsissydemi:
SissyDemi Featured By Owner Feb 18, 2012  Hobbyist Digital Artist
okies :3
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:iconiluvgreggsulkin222:
iluvgreggsulkin222 Featured By Owner Feb 13, 2012  Hobbyist Writer
you must like photo of crossdressing or sleepwear.



cool photo . ok
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:iconsissydemi:
SissyDemi Featured By Owner Feb 13, 2012  Hobbyist Digital Artist
I like crossdressing. :)

Sleepwear is nice, too. ;)
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:iconiluvgreggsulkin222:
iluvgreggsulkin222 Featured By Owner Feb 13, 2012  Hobbyist Writer
are you straight or bi
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:iconsissydemi:
SissyDemi Featured By Owner Feb 13, 2012  Hobbyist Digital Artist
I am straight.
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:iconiluvgreggsulkin222:
iluvgreggsulkin222 Featured By Owner Feb 13, 2012  Hobbyist Writer
ok just wonder .i just want to why does christnia dress chris like a girl.
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:iconsissydemi:
SissyDemi Featured By Owner Feb 13, 2012  Hobbyist Digital Artist
The real reason is I am into crossdressing and Chris is my cartoon avatar.

The story reason is she is a bit cruel and started it off as a joke and a way to humiliate him. Then she realized she liked him dressed up and suspects he kind of likes it, too.
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:iconeleventhdr:
eleventhdr Featured By Owner Dec 1, 2011  Hobbyist Artist
i love the frist boys girlly nithgown and would love to be wearin this when i go to sleep and when i wake up in the moring and am still in this cute nithgown! yes please and feeling all girly!
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:iconsissydemi:
SissyDemi Featured By Owner Dec 1, 2011  Hobbyist Digital Artist
Yeah, I love it, too. I used to have something similar, but a bit shorter and with matching shorts.
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:iconffecchifan:
FFecchifan Featured By Owner Apr 1, 2011
Funny.
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:iconprincessjessica:
PrincessJessica Featured By Owner Feb 28, 2011
oh that's nice :)
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:iconsissydemi:
SissyDemi Featured By Owner Feb 28, 2011  Hobbyist Digital Artist
Thanks! ^.^;;;

I just wish I could find the other 5 or 6 I did around the same time. I had an old website I had put them on, along with the BLSB stuff that had been done by then. If I could remember the website, I'd do a wayback search for them. ::sigh::
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:iconsilverwing37:
silverwing37 Featured By Owner Mar 2, 2011
Try storysite.com. I remember your posting from that website a while ago.
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:iconsissydemi:
SissyDemi Featured By Owner Mar 2, 2011  Hobbyist Digital Artist
Crystal's Storysite. Yeah. I have the illustrated Story there, as well as other items, including images I made special for her postcard system. (Those will be posted here eventually, too.)

The website I mentioned was one on a geocities server, or something like that. I remember you had to pick an area and block location and the URLs were long and full of numbers. Without the URL, it would be near impossible to locate again. And, my little brain has trouble recalling last week, let alone almost 20 years ago. haha
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February 28, 2011
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