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/r/crossdressed50
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2024
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Am I too old to wear this?
124 upvotes
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carriebtv
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Pretty in Pink!
81 upvotes
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AshleyinHeels
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Just a girl nextdoor
81 upvotes
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amber_gemstatediva
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Happy Hump day!💋💋
74 upvotes
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CelebrationAway4433
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50 vs. 60. Same dress.
72 upvotes
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carriebtv
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Glasses and dark hose anyone?
65 upvotes
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Electrical_Car_1507
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59 years old x
64 upvotes
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ResolveUpper
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Apparently……On Wednesday…..
63 upvotes
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Hot_Summer_Breeze
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Happy Monday!💋💙💋
60 upvotes
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CelebrationAway4433
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New dress.
58 upvotes
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Loose_Ad603
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Am I too old to wear this?
124
carriebtv
--
10
9
8
7
6
5
4
3
2
1
0
Pretty in Pink!
81
AshleyinHeels
--
10
9
8
7
6
5
4
3
2
1
0
Just a girl nextdoor
81
amber_gemstatediva
--
10
9
8
7
6
5
4
3
2
1
0
Happy Hump day!💋💋
74
CelebrationAway4433
--
10
9
8
7
6
5
4
3
2
1
0
50 vs. 60. Same dress.
72
carriebtv
--
10
9
8
7
6
5
4
3
2
1
0
Glasses and dark hose anyone?
65
Electrical_Car_1507
--
10
9
8
7
6
5
4
3
2
1
0
59 years old x
64
ResolveUpper
--
10
9
8
7
6
5
4
3
2
1
0
Apparently……On Wednesday…..
63
Hot_Summer_Breeze
--
10
9
8
7
6
5
4
3
2
1
0
Happy Monday!💋💙💋
60
CelebrationAway4433
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10
9
8
7
6
5
4
3
2
1
0
New dress.
58
Loose_Ad603
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10
9
8
7
6
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4
3
2
1
0
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