Including results for crossdress update.
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My First Date in Crossdresser Mode (Crossdressing Stories)
10:09
My First Date in Crossdresser Mode (Crossdressing Stories)
70.2K viewsDec 23, 2023
YouTubeSissy Maya
Let's dress up and go out together! Dating with a crossdresser ❤️
4:08
Let's dress up and go out together! Dating with a crossdresser ❤️
48.2K viewsJan 30, 2021
YouTubeKeira3327
8 Compelling Reasons to Date a Crossdresser
10:16
8 Compelling Reasons to Date a Crossdresser
4.3K viewsOct 3, 2024
YouTubeAbout TG Life
Dating with a crossdresser: Dress up as a girl in my floral dress
4:26
Dating with a crossdresser: Dress up as a girl in my floral dress
25.7K viewsSep 13, 2021
YouTubeKeira3327
Crossdresser Love Story: ESP02 First Date as a Girl...OMG We are holding hands
4:01
Crossdresser Love Story: ESP02 First Date as a Girl...OMG We are holding hands
57.7K viewsAug 30, 2021
YouTubeKeira3327
Dating with a crossdresser ❤️ Have a fun day with me🤗 walking in tube dress in the city
6:26
Dating with a crossdresser ❤️ Have a fun day with me🤗 walking in tube dress in the city
55.1K viewsMay 11, 2021
YouTubeKeira3327
Dating with a crossdresser: Meet me at the lakeside...I find my love 😝
5:05
Dating with a crossdresser: Meet me at the lakeside...I find my love 😝
28.3K viewsJun 19, 2021
YouTubeKeira3327
3:16
Dating with a crossdresser: Hold my hand, stay with me! In my leather skirt and ankle boots
23.6K viewsJul 24, 2021
YouTubeKeira3327
21:32
Friend Saw Me In Drag, Now We Are Dating 👗😘 (Crossdressing Stories)
17.2K viewsFeb 12, 2024
YouTubeKinda Cute
3:01
Dating with a crossdresser: Will you spend your Sunday morning with me? Let's have fun!
8.8K viewsJul 18, 2021
YouTubeKeira3327
3:33
Dating with a crossdresser: Dress up as a girl for a coffee. Care to join?
7.4K viewsFeb 2, 2023
YouTubeKeira3327
8:13
Summer Upstairs - A first time crossdressing experience
631.4K viewsAug 13, 2025
YouTubeBecoming Lacey
7:40
My First Time Cross Dressing Story Time WITH PICTURES | Casey Blake
521.4K viewsOct 18, 2016
YouTubeCasey Blake
1:38
CAUGHT CROSSDRESSING BY NEIGHBOR
187.1K viewsMay 24, 2023
YouTubeAlexa Bree
5:49
A cross-dresser supported by a crossdressing Friend | Crossdresser with cross-dressing partner.
102.4K views7 months ago
YouTubeAsmitha Transgender Library
10:14
The Different Phases of Crossdressing
55K viewsAug 18, 2024
YouTubeAbout TG Life
9:31
Supporting My Husband on His Crossdressing Journey
39.1K viewsFeb 10, 2024
YouTubeAbout TG Life
3:22
Crossdressing time 👏 I am dressing up as a girl again 🤣
15.3K viewsJun 11, 2022
YouTubeKeira3327
7:02
Dating with a crossdresser: ❤️Let's go for a walk❤️
38.8K viewsJun 29, 2021
YouTubeKeira3327
2:36
M2F Katie's Crossdressing Adventure
108.1K viewsOct 28, 2021
YouTubeCrossdressing Lifestyle
1:12
Crossdresser getting ready for our date.
5.7K viewsJun 15, 2023
YouTubeSissy Boy28
16:15
Magical Dress Changed My Gender (Crossdressing Stories)
71.1K viewsMar 25, 2023
YouTubeKinda Cute
0:10
Blonde Crossdresser Gives Dating Advice
31.5K viewsDec 28, 2021
YouTubeCDFling - Date a Crossdresser
4:41
crossdresser 18 - new dress like a bridesmaid coctail night
113.1K viewsFeb 19, 2016
YouTubeAnyaa Brook
5:53
I WAS A WOMAN - A Day of Crossdressing
301.7K viewsApr 6, 2016
YouTubeJayme Antonio Sejean
2:21
Crossdresser Outfits Vol 02
183.3K viewsSep 30, 2014
YouTubeArt AM
1:00
DRESS UP! DRESS OUT! Crossdressing Confidence!
37.2K viewsFeb 12, 2022
YouTubeJasmine Page
4:51
Dating with a crossdresser: Is this dress too short?🌸Crossdressing in Spring Festival, embarrassing
16.3K viewsNov 16, 2022
YouTubeKeira3327
8:02
Outwitted into CROSSDRESSING [CROSSDRESSER STORY]
60.5K viewsJan 10, 2023
YouTubeLuna's Crossdressing Stories
3:46
Crossdresser Paul’s First Date As A Woman! | First Dates
143K viewsDec 17, 2018
YouTubeFirst Dates
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