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I just spent 3 days in the Hospital.
11:13
I just spent 3 days in the Hospital.
9.2K viewsMay 7, 2023
YouTubeJessie Pharaoh
I wore a new red dress and stockings to the Mall
10:03
I wore a new red dress and stockings to the Mall
49.7K viewsJan 25, 2024
YouTubeJessie Pharaoh
A Unique New Dress
12:05
A Unique New Dress
10.8K viewsJul 20, 2023
YouTubeJessie Pharaoh
He Liked My Outfit
9:29
He Liked My Outfit
24.9K viewsSep 2, 2023
YouTubeJessie Pharaoh
Crossdressing in another $14 Dress From Walmart
10:28
Crossdressing in another $14 Dress From Walmart
43K viewsSep 17, 2022
YouTubeJessie Pharaoh
New Dress and a White Lace Trimmed Slip (Crossdressing)
14:27
New Dress and a White Lace Trimmed Slip (Crossdressing)
5.8K viewsOct 31, 2022
YouTubeJessie Pharaoh
Crossdressing on a Rainy Day
9:21
Crossdressing on a Rainy Day
3.7K viewsJun 19, 2023
YouTubeJessie Pharaoh
15:21
A rusty colored dress for a rusty old crossdresser
8.6K viewsOct 14, 2024
YouTubeJessie Pharaoh
12:20
Tan Pantyhose with a Long Skirt
2K viewsApr 7, 2025
YouTubeJessie Pharaoh
12:39
New Blue Dress
4.5K viewsJun 28, 2023
YouTubeJessie Pharaoh
12:40
My last shopping day before the big winter blizzard hits, and Christma…
3.7K viewsDec 24, 2022
YouTubeJessie Pharaoh
12:57
Fishnet Tights with Ripped Jeans (Crossdressing)
4K viewsApr 27, 2023
YouTubeJessie Pharaoh
14:13
I had a high heel blow out
14.1K viewsJul 21, 2023
YouTubeJessie Pharaoh
12:57
Doing What I Do Best. Shopping.
4.9K viewsNov 22, 2023
YouTubeJessie Pharaoh
12:29
Jessie's Crossdressing Bloopers, Blunders, and Outtakes #7
6K viewsDec 9, 2024
YouTubeJessie Pharaoh
12:57
New Dress, New Hair Color, Pantyhose and Boots (Crossdress…
10.3K viewsNov 23, 2022
YouTubeJessie Pharaoh
10:25
Shopping in Comfortable Heels (Crossdressing)
6.2K viewsJan 26, 2023
YouTubeJessie Pharaoh
1:57
Can I ride a Boogie Board across the pool while wearing pantyhose
5K viewsAug 14, 2023
YouTubeJessie Pharaoh
5:08
Hedge Clippers
4.8K viewsMay 8, 2023
YouTubeJessie Pharaoh
5:27
Human Interactions
19K viewsDec 12, 2023
YouTubeJessie Pharaoh
13:59
Do You Like Pantyhose ?
10.4K viewsAug 24, 2023
YouTubeJessie Pharaoh
10:32
He Asked Me If I Was Transgender
4.3K viewsAug 8, 2022
YouTubeJessie Pharaoh
13:44
He Gave Me His Coupons Because I Wore Pantyhose
10K viewsJul 26, 2023
YouTubeJessie Pharaoh
11:05
I suck at Pool
4.6K viewsOct 30, 2021
YouTubeJessie Pharaoh
26:22
Jessie J - Who You Are Collection (Live At Troubadour / 2019)
3.8M viewsFeb 25, 2021
YouTubeJessieJVEVO
2:29
H.A.P.P.Y
157.3K views6 months ago
YouTubeJessie J - Topic
11:52
Let's Go Shopping
9.7K viewsJul 22, 2023
YouTubeJessie Pharaoh
14:05
Dressing Room Try On and Shopping
14.5K viewsJul 13, 2022
YouTubeJessie Pharaoh
0:50
Crossdresser Gets Asked Out on a Date
10.1K viewsMar 5, 2023
YouTubeJessie Pharaoh
9:36
Same outfit as before, but I lost my heels
3.9K viewsMay 28, 2022
YouTubeJessie Pharaoh
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