satban
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Sissy page boy fantasy
#1
   

Adam
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#2
A very attractive Stepmother, and with a presence that would make any little boy go weak at the knees, I'm sure. Thanks for posting.
Know thy self, sissy.  Don't whine, don't pine, learn to expand your mind.   
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#3
I've never been lucky enough to do it, but I've always dreamed of being a bridesmaid, especially one like this:

https://imgur.com/3jfLl6R

The thought of sitting in my silky lingerie and white patterned stockings while having my hair and make up done, with the other bridesmaids chattering away, makes me go weak at the knees.
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#4
I could imagine being treated as a sissy page boy with a white sailor suit top/onesie and thick terry nappies and plastic pants with white tights pulled up and then a navy pair of elastic waist/leg velvet shorts.

Shiny black leather mary jane shoes and a little sailor hat with elastic under my chin to hold it in place, dummy attached with a safety pin and navy satin ribbon.

Having to behave myself as everyone fusses over me, pinching my cheek, patting my nappied bottom, warning me not to scuff my shoes, the page girls taking charge of me for the wedding, before I'm lead off by a strict Nanny who babysits me for the afternoon, getting me ready for wedding photos, keeping me under control with baby reins and a firm grip until the photos are done and she leads me away to dinner and bedtime.
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#5
Being dressed as such a little sissy page boy would indeed be thoroughly humiliating, especially if you were made to use your nappies and then have them changed in front of the bridesmaids.

I would find it even more humiliating to be dressed like one of the bridesmaids, maybe in one of these outfits:

https://imgur.com/65FClX3

Nanny would find it much easier to check and change my nappy if I had a little dress on.
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