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February 28, 2011
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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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:iconiluvgreggsulkin222:
iluvgreggsulkin222 Featured By Owner Feb 17, 2012  Hobbyist Writer
do you mind if i use this photo for a story.
Reply
: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!
Reply
:iconiluvgreggsulkin222:
iluvgreggsulkin222 Featured By Owner Feb 18, 2012  Hobbyist Writer
i deside not ot write a story
Reply
:iconsissydemi:
SissyDemi Featured By Owner Feb 18, 2012  Hobbyist Digital Artist
okies :3
Reply
: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
Reply
:iconsissydemi:
SissyDemi Featured By Owner Feb 13, 2012  Hobbyist Digital Artist
I am straight.
Reply
: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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