Maid Dress
29,617 100%
Maid Dress
6 years ago
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in the long ago early on even before puberty i was taught to dress as a girl. mom and dad liked to dress me as a maid and serve their guests refreshments when they hosted a social gathering. they had me on something so i was able to function but totally relaxed and defenseless. i saw and experienced things you can imagine and you're probably right. i was so adept at the role i was soon being rented out or hired to other parties, sometimes large gatherings where i was part of a service team and sometimes one on one serving a usually older man or even woman who always wanted a boy to be a girl and wait on her needs. this served me well early on my time in the city. i managed to maintain a room in a fleabag hotel near penn station and i had a busy dance card of customers, usually frustrated husbands on their way home to long island and loveless marriages or closeted queers looking for a smooth young ass and frill dress.
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