Including results for crossdressing date.
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Dating a Crossdresser
11:53
Dating a Crossdresser
13.8K views5 months ago
YouTubeCatch Queen
Is It Possible to Date Openly as a Crossdresser?
3:31
Is It Possible to Date Openly as a Crossdresser?
5.5K views1 month ago
YouTubeAbout TG Life
Dating as a Crossdresser: Where to Find Honest Partners
9:03
Dating as a Crossdresser: Where to Find Honest Partners
1.1K views5 months ago
YouTubeMy Life My Rules
Crossdressing friends create more intimacy then girlfriends | How to find a cross-dressing friend.
8:08
Crossdressing friends create more intimacy then girlfriends | How to find a cross-dressing friend.
48.3K views2 months ago
YouTubeAsmitha Transgender Library
My First Date As A Woman | Crossdressing Story
8:08
My First Date As A Woman | Crossdressing Story
34.2K viewsJul 18, 2025
YouTubePride Pulse🏳️‍🌈
Crossdressing & Dating: How Do Women REALLY React?
0:36
Crossdressing & Dating: How Do Women REALLY React?
403 views1 month ago
YouTubeNastja Sherer • Your Favourite Crossdresser
Our First Date As Girlfriends 👩‍❤️ (Crossdressing Stories – MtF Transition)
23:44
Our First Date As Girlfriends 👩‍❤️ (Crossdressing Stories – MtF Transition)
2.6K views11 months ago
YouTubeKinda Cute
3:13
How I started crossdressing 💄
153K views4 months ago
YouTubeKlara N
8:08
Beautiful Cross-dressers have fun with their boyfriends | My girlfriend is a boy.
82K views2 months ago
YouTubeAsmitha Transgender Library
15:33
Crossdressing & Relationships: When and How to Tell Your Partner
9K views6 months ago
YouTubeNastja Sherer • Your Favourite Crossdresser
5:49
A cross-dresser supported by a crossdressing Friend | Crossdresser with cross-dressing partner.
95.4K views7 months ago
YouTubeAsmitha Transgender Library
8:32
Dared to Crossdress for a Date: A Crossdressing MTF Story
32.5K views5 months ago
YouTubePride Pulse🏳️‍🌈
10:09
My First Date While Crossdressed (Crossdressing Stories)
8K views6 months ago
YouTubeSissy Maya
22:32
Dating a Crossdresser: The Honesty That Changed Everything
10K views9 months ago
YouTubeLadies Into Crossdressing
25:05
I Dated Crossdressers for Years—Here’s What No One Understands
2.6K views7 months ago
YouTubeLadies Into Crossdressing
1:22:21
Dating a Crossdresser: Would I Do It?
1.5K views4 months ago
YouTubeSoul Kink
3:59
Crossdresser Wearing Red Dress - Ready for Date Night
82.4K views7 months ago
YouTubeDee
8:08
Cross-dressers who enjoy meeting and socializing with friends who also cross-dress.
49.9K views6 months ago
YouTubeAsmitha Transgender Library
1:05:18
i met my wife while crossdressed: a love story
22.7K views5 months ago
YouTubeSoul Kink
27:28
I Dated Men Who Crossdress—Here’s What Surprised Me Most
4K views6 months ago
YouTubeLadies Into Crossdressing
20:28
Dating a Crossdresser Changed My Standards in Men
2.2K views5 months ago
YouTubeLadies Into Crossdressing
8:56
Beautiful cross-dressers outing in public places | Tips for going out cross-dressing - Episode 1
45.9K views4 months ago
YouTubeAsmitha Transgender Library
59:11
Crossdressing made me a better man
29.4K views4 months ago
YouTubeSoul Kink
10:18
I Crossdressed for My Boss for the First Time | A Crossdressing MTF Story
49.2K views3 months ago
YouTubePride Pulse🏳️‍🌈
11:05
My Husband Wears My Clothes - A Crossdressing MTF Story
100.5K views7 months ago
YouTubePride Pulse🏳️‍🌈
10:09
My First Date in Crossdresser Mode (Crossdressing Stories)
70.2K viewsDec 23, 2023
YouTubeSissy Maya
14:56
How To Find Dates as a Crossdresser
19K viewsJan 6, 2023
YouTubeRamada The Femme
21:32
Friend Saw Me In Drag, Now We Are Dating 👗😘 (Crossdressing Stories)
17K viewsFeb 12, 2024
YouTubeKinda Cute
10:30
Crossdressing & Relationships | How to Talk to Your Partner
4.9K views8 months ago
YouTubeNastja Sherer • Your Favourite Crossdresser
10:16
8 Compelling Reasons to Date a Crossdresser
4.3K viewsOct 3, 2024
YouTubeAbout TG Life
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