Including results for my crossdresser date.
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Dating a Crossdresser
11:53
Dating a Crossdresser
6.5K views2 weeks ago
YouTubeCatch Queen
Dating a Crossdresser: The Honesty That Changed Everything
22:32
Dating a Crossdresser: The Honesty That Changed Everything
7.9K views4 months ago
YouTubeLadies Into Crossdressing
Dating a Crossdresser Changed My Standards in Men
20:28
Dating a Crossdresser Changed My Standards in Men
1.7K views1 month ago
YouTubeLadies Into Crossdressing
I Dated Crossdressers for Years—Here’s What No One Understands
25:05
I Dated Crossdressers for Years—Here’s What No One Understands
2K views2 months ago
YouTubeLadies Into Crossdressing
Dared to Crossdress for a Date: A Crossdressing MTF Story
8:32
Dared to Crossdress for a Date: A Crossdressing MTF Story
24.2K views1 month ago
YouTubePride Pulse🏳️‍🌈
My First Date As A Woman | Crossdressing Story
8:08
My First Date As A Woman | Crossdressing Story
22.7K views10 months ago
YouTubePride Pulse🏳️‍🌈
My Most Romantic Crossdressing Date Night 💖 | Crossdressing Stories
42:32
My Most Romantic Crossdressing Date Night 💖 | Crossdressing Stories
1.4K views8 months ago
YouTubeGlam Shift
9:03
Dating as a Crossdresser: Where to Find Honest Partners
803 views1 month ago
YouTubeMy Life My Rules
15:33
Crossdressing & Relationships: When and How to Tell Your Partner
5.7K views2 months ago
YouTubeNastja Sherer • Your Favourite Crossdresser
23:44
Our First Date As Girlfriends 👩‍❤️ (Crossdressing Stories – MtF Transition)
2.3K views7 months ago
YouTubeKinda Cute
8:44
Dating a Woman vs. Dating a Man (Tips for MTF Crossdresser)
349 views3 weeks ago
YouTubeMy Life My Rules
10:30
Crossdressing & Relationships | How to Talk to Your Partner
3.8K views4 months ago
YouTubeNastja Sherer • Your Favourite Crossdresser
5:49
A cross-dresser supported by a crossdressing Friend | Crossdresser with cross-dressing partner.
63.6K views2 months ago
YouTubeAsmitha Transgender Library
7:40
How To Date Men as a Transgender Woman / Crossdresser
45.4K viewsOct 9, 2024
YouTubeYoya Fabulosa
18:25
Friend Saw Me In Drag, Now We Are Dating (MTF Crossdressing Story)
3.7K viewsMay 8, 2025
YouTubeMy Life My Rules
24:19
“The Day I Finally Met Myself 💫 | Crossdressing Story”
217 views7 months ago
YouTubeLuna Truths
33:02
“My Crossdressing Husband Ready For His First Date | MtF Transformation & Crossdressing 🌸”
1.1K views5 months ago
YouTubeSissy Fantasy World
30:36
The Secret Date That Changed My Life 🌷 | Transgender Romance Journey
395 views7 months ago
YouTubeSissy Fantasy World
11:05
My Husband Wears My Clothes - A Crossdressing MTF Story
67.5K views2 months ago
YouTubePride Pulse🏳️‍🌈
4:16
From Husband to Bimbo | A Wife’s Control | Crossdressing Story
21.8K views5 months ago
YouTubeLuna Truths
16:34
Every Month We Do This... A Couple's Transformation You Won't Expect - Crossdressing Story
13.1K views5 months ago
YouTubeThe Gender Diary
49:10
My Crossdresser Husband Dating A Trans, When I found, It Shocked Me, MtF & TG TF, Crossdressing 🌸
583 views4 months ago
YouTubeSissy Fantasy World
9:50
Truth Or Dare: A First Time Crossdressing Experience
8.4K views4 months ago
YouTubePride Pulse🏳️‍🌈
4:42
5 Best Cold Weather Crossdressing Tips Every Crossdresser Needs to See #confidenc #tarot #makeu
19.6K views3 months ago
YouTubeCrossdressing Lifestyle
8:13
Summer Upstairs - A first time crossdressing experience
494.4K views9 months ago
YouTubeBecoming Lacey
4:22
How to Date TRANSGENDER Women | Crossdressers | FemBoys
43.4K viewsOct 22, 2024
YouTubeYoya Fabulosa
4:04
Advantages of dating a Crossdresser
10K viewsApr 25, 2025
YouTubePaige Darling
20:53
Turned Into A Femboy To Date My Crush 👗❤️😳 (Crossdressing Stories)
6.6K views11 months ago
YouTubeKinda Cute
10:16
8 Compelling Reasons to Date a Crossdresser
3.4K viewsOct 3, 2024
YouTubeAbout TG Life
3:09
DATE ME? | Crossdresser Life
13.7K viewsDec 8, 2024
YouTubeAlexa Jane Smith
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Short videos

2:27
Crossdresser in a cute outfit for a date night – CrossDre…
36.3K viewsMay 26, 2021
YouTubeCrossDresser Carmen
0:11
Becoming My Dude Date #mtf #transformation crossdres…
22K views4 months ago
YouTubeThe Male-to-Fabulous Project
2:29
My Husband is now my Wife |Crossdresser Couple | Mal…
83.1K viewsDec 3, 2022
YouTubeTransgender and Crossdressing Hub
2:21
Crossdresser in bright pink dress, ready for a date – Cr…
50.3K viewsApr 29, 2021
YouTubeCrossDresser Carmen
1:40
Transgender Dating – 100 Romantic Date Night Ideas …
407 viewsJul 6, 2023
YouTubeMy Transgender Cupid
0:13
#crossdresser Date Outfits 🐆🖤 | #crossdressing #mtf #trans…
2.1K views1 month ago
YouTubeCrossDresser Carmen
2:22
Crossdressing Role Reversal Marriage || Crossdresser C…
69.9K viewsNov 9, 2022
YouTubeTransgender and Crossdressing Hub
0:06
Winks from a cute Crossdresser
6.3K viewsJan 7, 2022
YouTubeCDFling - Date a Crossdresser
0:12
My best friend is going on his first date as a woman... che…
1.4K views5 months ago
YouTubeQUEER GLAMOUR
0:26
Trans Dating In California Chat And Date With Local T…
168 viewsJun 8, 2023
YouTubeMy Transgender Cupid
0:18
Crossdresser Date Night Dress #mtf #feminization
95.3K views5 months ago
YouTubeSera Cross
1:51
Crossdressing vs Transition. Sneak Peek to my LIVE con…
12.3K views3 months ago
YouTubeNastja Sherer • Your Favourite Cross…
1:05
Male to female transgender transition. Hrt, crossdressing
5.8K viewsFeb 16, 2023
YouTubeJessie’s Time
2:34
This Beautiful Transgender Living the Best Time of her …
35.1K viewsJun 14, 2023
YouTubeTransgender and Crossdressing Hub
2:22
Crossdresser in red dress, ready for valentine’s day – …
57.1K viewsApr 25, 2021
YouTubeCrossDresser Carmen
0:07
My girlfriends turned up for tea in thigh boots and leath…
10.1K views6 months ago
YouTubeThe Sunday Girl
0:13
Transgender MtF: another from early in transition mo…
7.8K viewsSep 22, 2021
YouTubeJessie’s Time
1:39
Male to female transgender transition. Hrt, MtF, crossdr…
31.8K viewsDec 22, 2022
YouTubeJessie’s Time
0:20
Ladies Weekend for Crossdressers! 5 - 7 May 2…
11.4K viewsApr 25, 2023
YouTubeCrossdressing Shopping and Service …
0:23
MALE TO FEMALE BEAUTIFUL BRIDE - Ladie…
14K viewsOct 8, 2022
YouTubeCrossdressing Shopping and Service …
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