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/r/crossdressed50

OGIM! Business top, playful skirt! <3

2 upvotes • brianna_michelle69
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Little past 50 but staying focused

2 upvotes • missmailecd
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DATE NIGHT OUTFIT?? Or office??

2 upvotes • addison-clarke067
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My wife's lounger dress, my pink flip flops, my new guitar...triple win! <3

2 upvotes • brianna_michelle69
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Probably the last of my guitar sessions for now. I picture myself wearing this to a summer party (and jamming a bit too!) <3

1 upvotes • brianna_michelle69
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Morning at the beach NSFW

1 upvotes • Traditional_Major941
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I have a crush on my professor!! You think he will notice me in class today???☺️

1 upvotes • sissy-fantasyyy
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Almost forgot my favorite girls!! Have a great monday!

1 upvotes • RoxyMidwest
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Time for bed 🥰 NSFW

1 upvotes • amberkhu
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Words you never hear!

1 upvotes • Slight-Fly-6690
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