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/u/HovercraftMajestic51's
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/r/my_sissycaptions
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2024
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My best friend found out about my secret...
NSFW
240 upvotes
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Dude, lets go already...
NSFW
181 upvotes
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Your roommate caught you dressed up...
NSFW
141 upvotes
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You were a failing medstudent
NSFW
141 upvotes
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Your bro just came home from a date...
NSFW
139 upvotes
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Your roommate left for work...
NSFW
128 upvotes
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You thought it was just another stupid TikTok trend...
NSFW
126 upvotes
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It started with some innocent reddit messages...
NSFW
110 upvotes
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Dared to dress up as a girl and try out for cheerleader...
NSFW
103 upvotes
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Just making it wet - part 1
NSFW
96 upvotes
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My best friend found out about my secret...
NSFW
240
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10
9
8
7
6
5
4
3
2
1
0
Dude, lets go already...
NSFW
181
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10
9
8
7
6
5
4
3
2
1
0
Your roommate caught you dressed up...
NSFW
141
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10
9
8
7
6
5
4
3
2
1
0
You were a failing medstudent
NSFW
141
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10
9
8
7
6
5
4
3
2
1
0
Your bro just came home from a date...
NSFW
139
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10
9
8
7
6
5
4
3
2
1
0
Your roommate left for work...
NSFW
128
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10
9
8
7
6
5
4
3
2
1
0
You thought it was just another stupid TikTok trend...
NSFW
126
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10
9
8
7
6
5
4
3
2
1
0
It started with some innocent reddit messages...
NSFW
110
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10
9
8
7
6
5
4
3
2
1
0
Dared to dress up as a girl and try out for cheerleader...
NSFW
103
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10
9
8
7
6
5
4
3
2
1
0
Just making it wet - part 1
NSFW
96
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