Including results for crossdresser date.
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8 Compelling Reasons to Date a Crossdresser
10:16
Find in video from 0:00Introduction to Dating a Crossdresser
8 Compelling Reasons to Date a Crossdresser
2.3K viewsOct 3, 2024
YouTubeAbout TG Life
How To Date Men as a Transgender Woman / Crossdresser
7:40
How To Date Men as a Transgender Woman / Crossdresser
42.2K viewsOct 9, 2024
YouTubeYoya Fabulosa
How to Date TRANSGENDER Women | Crossdressers | FemBoys
4:22
How to Date TRANSGENDER Women | Crossdressers | FemBoys
41.5K viewsOct 22, 2024
YouTubeYoya Fabulosa
DATE ME? | Crossdresser Life
3:09
DATE ME? | Crossdresser Life
13.4K viewsDec 8, 2024
YouTubeAlexa Jane Smith
Crossdressing - My perfect Date night Dress
1:00
Crossdressing - My perfect Date night Dress
10.9K viewsMay 22, 2024
YouTubeCrossdressing Lifestyle
Advantages of dating a Crossdresser
4:04
Advantages of dating a Crossdresser
9.2K views8 months ago
YouTubePaige Darling
My First Date as a Crossdresser 💖#mtf
20:09
My First Date as a Crossdresser 💖#mtf
12.1K viewsOct 5, 2024
YouTubeTransformHER Stories💙
11:22
🌈✨ TRANSFORMATIVE NIGHT OUT! 🌟👠 My Crossdressing Sissy Date Adv…
8.1K viewsFeb 28, 2024
YouTubeSissy Tanias Crossdressing and Feminization s…
23:44
Our First Date As Girlfriends 👩‍❤️ (Crossdressing Stories – MtF Tran…
1.7K views2 months ago
YouTubeKinda Cute
22:19
My First Date as Greta – Wearing a Dress & Heels the First Time! Cros…
4.8K viewsDec 23, 2024
YouTubeMiss Charlotte
9:15
10 Joyful Activities Crossdressers Can Do
34.7K viewsAug 21, 2024
YouTubeAbout TG Life
8:08
My First Date As A Woman | Crossdressing Story
13.7K views5 months ago
YouTubePride Pulse🏳️‍🌈
3:28
Sissygram Stories: Crossdress on Date with Girl (Crossdressing Stor…
3.8K viewsNov 10, 2024
YouTubeSissygram Stories
21:32
Find in video from 01:17Transformation into Crossdressing
Friend Saw Me In Drag, Now We Are Dating 👗😘 (Crossdressing Stories)
15.6K viewsFeb 12, 2024
YouTubeKinda Cute
0:12
Crossdresser Can't Decide on Dress for Date Night #feminization
54.7K views5 months ago
YouTubeJoann Abernathy
11:53
Sissy's First Date Part 2 - A Crossdressing Audio Story
25.3K views10 months ago
YouTubeJen Occasionally
9:39
6 Essential Ways to Commit to Crossdressing
19.3K viewsSep 5, 2024
YouTubeAbout TG Life
20:53
Turned Into A Femboy To Date My Crush 👗❤️😳 (Crossdressing Stories)
5.2K views6 months ago
YouTubeKinda Cute
1:52
Crossdresser Veronica in Hotel: Quick Dates
3.6K views8 months ago
YouTubeLeggy Veronica
9:32
The Pros and Cons of Crossdressing at a Mature Age
105K viewsSep 14, 2024
YouTubeAbout TG Life
9:31
Supporting My Husband on His Crossdressing Journey
34.4K viewsFeb 10, 2024
YouTubeAbout TG Life
10:29
What I LOVE About CROSSDRESSERS! (Crossdressin…
13.4K views4 months ago
YouTubeSoft Silky Secrets
5:26
Crossdresser's First Date: Tg Transformation Stories | tg tf | mtf …
63.5K viewsSep 10, 2024
YouTubetg transformation stories
3:23
A Beautiful Crossdresser 'Now Boys Will be Girls' | Boy to Girl | MTF Tr…
13K views4 months ago
YouTubeTransgender and Crossdressing Hub
8:13
Summer Upstairs - A first time crossdressing experience
313.6K views4 months ago
YouTubeBecoming Lacey
8:25
💃 "Your Fabulous Beginner’s Guide to Crossdressing!" 💖 Become the gi…
5.6K views10 months ago
YouTubeSissy Tanias Crossdressing and Feminization s…
4:31
Crossdresser’s First Date
95.1K viewsSep 1, 2022
YouTubeInes CD
4:09
Find in video from 0:00Introduction to Crossdressing
Dating Tips as a Crossdresser
12K viewsDec 11, 2021
YouTubeAbout TG Life
10:09
My First Date in Crossdresser Mode (Crossdressing Stories)
59.7K viewsDec 23, 2023
YouTubeSissy Maya
1:40
How to Crossdress - Start Your Feminine Journey with Confidence
15K views9 months ago
YouTubeFitUstyle
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Short videos

10:16
8 Compelling Reasons to Date a Crossdresser
2.3K viewsOct 3, 2024
YouTubeAbout TG Life
7:40
How To Date Men as a Transgender Woman / Cros…
42.2K viewsOct 9, 2024
YouTubeYoya Fabulosa
4:22
How to Date TRANSGENDER Women | Crossdressers | F…
41.5K viewsOct 22, 2024
YouTubeYoya Fabulosa
3:09
DATE ME? | Crossdresser Life
13.4K viewsDec 8, 2024
YouTubeAlexa Jane Smith
1:00
Crossdressing - My perfect Date night Dress
10.9K viewsMay 22, 2024
YouTubeCrossdressing Lifestyle
4:04
Advantages of dating a Crossdresser
9.2K views8 months ago
YouTubePaige Darling
20:09
My First Date as a Crossdresser 💖#mtf
12.1K viewsOct 5, 2024
YouTubeTransformHER Stories💙
11:22
🌈✨ TRANSFORMATIVE NIGHT OUT! 🌟👠 My Crossdressing Si…
8.1K viewsFeb 28, 2024
YouTubeSissy Tanias Crossdressing and Femi…
23:44
Our First Date As Girlfriends 👩‍❤️ (Crossdressing Stori…
1.7K views2 months ago
YouTubeKinda Cute
22:19
My First Date as Greta – Wearing a Dress & Heels th…
4.8K viewsDec 23, 2024
YouTubeMiss Charlotte
9:15
10 Joyful Activities Crossdressers Can Do
34.7K viewsAug 21, 2024
YouTubeAbout TG Life
8:08
My First Date As A Woman | Crossdressing Story
13.7K views5 months ago
YouTubePride Pulse🏳️‍🌈
3:28
Sissygram Stories: Crossdress on Date with Gi…
3.8K viewsNov 10, 2024
YouTubeSissygram Stories
21:32
Friend Saw Me In Drag, Now We Are Dating 👗😘 (Crossdres…
15.6K viewsFeb 12, 2024
YouTubeKinda Cute
0:12
Crossdresser Can't Decide on Dress for Date Night #fe…
54.7K views5 months ago
YouTubeJoann Abernathy
11:53
Sissy's First Date Part 2 - A Crossdressing Audio Story
25.3K views10 months ago
YouTubeJen Occasionally
9:39
6 Essential Ways to Commit to Crossdressing
19.3K viewsSep 5, 2024
YouTubeAbout TG Life
20:53
Turned Into A Femboy To Date My Crush 👗❤️😳 (Cross…
5.2K views6 months ago
YouTubeKinda Cute
1:52
Crossdresser Veronica in Hotel: Quick Dates
3.6K views8 months ago
YouTubeLeggy Veronica
9:32
The Pros and Cons of Crossdressing at a Mature …
105K viewsSep 14, 2024
YouTubeAbout TG Life
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