Including results for crossdressed for first date.
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My First Date in Crossdresser Mode (Crossdressing Stories)
10:09
My First Date in Crossdresser Mode (Crossdressing Stories)
59.8K viewsDec 23, 2023
YouTubeSissy Maya
Crossdressing Transformation: My First Date Experience
22:56
Crossdressing Transformation: My First Date Experience
304 views8 months ago
YouTubeCrossdressing Stories
8 Compelling Reasons to Date a Crossdresser
10:16
8 Compelling Reasons to Date a Crossdresser
2.6K viewsOct 3, 2024
YouTubeAbout TG Life
My First Date as Greta – Wearing a Dress & Heels the First Time! Crossdressedstory,Boy2Girl,M2F,TGTF
22:19
My First Date as Greta – Wearing a Dress & Heels the First Time! Cros…
5K viewsDec 23, 2024
YouTubeMiss Charlotte
My First Date As A Woman | Crossdressing Story
8:08
My First Date As A Woman | Crossdressing Story
13.9K views6 months ago
YouTubePride Pulse🏳️‍🌈
Crossdresser’s First Date
4:31
Crossdresser’s First Date
95.3K viewsSep 1, 2022
YouTubeInes CD
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 …
53.2K viewsAug 30, 2021
YouTubeKeira3327
22:31
My First Date As Cross Dressed But** l #Crossdressing Stories l #t…
6.5K viewsJun 28, 2024
YouTubeTransformHER Stories💙
7:40
How To Date Men as a Transgender Woman / Crossdresser
42.6K viewsOct 9, 2024
YouTubeYoya Fabulosa
4:22
How to Date TRANSGENDER Women | Crossdressers | FemBoys
41.8K viewsOct 22, 2024
YouTubeYoya Fabulosa
4:09
Find in video from 00:46Opening Up to a Date
Dating Tips as a Crossdresser
11.6K viewsDec 11, 2021
YouTubeAbout TG Life
0:10
Blonde Crossdresser Gives Dating Advice
30.3K viewsDec 28, 2021
YouTubeCDFling - Date a Crossdresser
1:00
Crossdressing - My perfect Date night Dress
11.1K viewsMay 22, 2024
YouTubeCrossdressing Lifestyle
1:46
Find in video from 00:15James' First Glance
Dating a Crossdresser TG Romantic Story
8.5K viewsAug 21, 2023
YouTubeFlawlessly Fem
19:49
My First Time Feminized (MTF Crossdressing Story)
9.7K views10 months ago
YouTubeMy Life My Rules
18:30
Trying On Dresses for the First Time [Crossdressing Stories / MtF Tran…
23K viewsNov 20, 2024
YouTubeBoys2Fem
14:56
Find in video from 07:04The Impact of Public Dates
How To Find Dates as a Crossdresser
16.1K viewsJan 6, 2023
YouTubeRamada The Femme
17:20
How to Start Crossdressing - 5 Beginner Tips
17.9K viewsNov 22, 2024
YouTubeCatch Queen
17:14
Husband Tries on Dress for the First Time (MTF Crossdressing Story)
3.1K views9 months ago
YouTubeMy Life My Rules
1:40
How to Crossdress - Start Your Feminine Journey with Confidence
15K views9 months ago
YouTubeFitUstyle
8:35
Man as a housewife, An amazing CrossDressing Story
45.3K viewsSep 22, 2023
YouTubeAbout TG Life
15:08
Wives And Their Feminized Husbands (MTF Crossdressing St…
14.1K viewsDec 17, 2024
YouTubeMy Life My Rules
11:49
My First Date as a "Transgender" after HRT.
11.7K viewsApr 8, 2022
YouTubeAurorA
3:05
Transforming Love: How I Feminized My Husband 💖👗👠
55.2K viewsOct 24, 2024
YouTubeSissy Tanias Crossdressing and Feminization s…
4:16
Date Reveals She's Transgender | First Dates
677.4K viewsNov 21, 2018
YouTubeChannel 4 Entertainment
19:29
Wife Takes Control of Husband (MTF Crossdressing Story)
45.4K views10 months ago
YouTubeMy Life My Rules
3:46
Crossdresser Paul’s First Date As A Woman! | First Dates
139.3K viewsDec 17, 2018
YouTubeFirst Dates
9:31
Supporting My Husband on His Crossdressing Journey
34.8K viewsFeb 10, 2024
YouTubeAbout TG Life
1:12
Crossdresser getting ready for our date.
5.5K viewsJun 15, 2023
YouTubeSissy Boy28
33:02
“My Crossdressing Husband Ready For His First Date | MtF Transform…
536 views1 month ago
YouTubeSissy Fantasy World
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2:27
Crossdresser in a cute outfit for a date night – CrossDre…
35.6K viewsMay 26, 2021
YouTubeCrossDresser Carmen
1:00
Crossdressing - My perfect Date night Dress
11.1K viewsMay 22, 2024
YouTubeCrossdressing Lifestyle
2:21
Crossdresser in bright pink dress, ready for a date – Cr…
50K viewsApr 29, 2021
YouTubeCrossDresser Carmen
0:57
What was it like the first time you crossdressed in publi…
2.3K views4 months ago
YouTubeBecoming Lacey
0:06
First Time Fully Dressed as a Girl Transformation Experi…
871.8K viewsAug 14, 2024
TikToktrappinbritt
Helping My Husband Crossdress: A Fashion Twi…
1.6M viewsApr 4, 2022
TikTokhappygoliving
0:39
Transgender Early Transition: CK dress. Male …
3.3K viewsSep 20, 2021
YouTubeJessie’s Time
2:28
A Dream Transgender who Inspire Others | Male to Fe…
37K viewsJun 10, 2023
YouTubeTransgender and Crossdressing Hub
2:29
My Husband is now my Wife |Crossdresser Couple | Mal…
77.1K viewsDec 3, 2022
YouTubeTransgender and Crossdressing Hub
2:47
Boy Who Lives as a Girl | Boy to Girl Transition | Male to …
70.4K viewsApr 23, 2023
YouTubeTransgender and Crossdressing Hub
0:15
Transgender: Early in transition wearing a fave C…
3.9K viewsSep 21, 2021
YouTubeJessie’s Time
What’s life like being married to a Crossdresser? For me…
48.4K viewsFeb 19, 2023
TikTokthe_crossdressers_wife
1:42
Male to female transgender transition. MtF, crossdressi…
16.1K viewsFeb 21, 2023
YouTubeJessie’s Time
2:34
This Beautiful Transgender Living the Best Time of her …
34.2K viewsJun 14, 2023
YouTubeTransgender and Crossdressing Hub
0:13
Transgender MtF: another from early in transition mo…
7.2K viewsSep 22, 2021
YouTubeJessie’s Time
2:38
Transwoman with Supportive Wife and Daughter | Male t…
99.9K viewsDec 19, 2022
YouTubeTransgender and Crossdressing Hub
2:13
Transgender MtF. Male to female transition hrt cross…
34.1K viewsSep 22, 2021
YouTubeJessie’s Time
1:00
Crossdressing Summer, it's on its way? Time for the Sh…
9.9K viewsMay 9, 2024
YouTubeCrossdressing Lifestyle
2:36
Crossdressing #5 in a wedding dress
177K viewsApr 20, 2021
YouTubeWoman Crossdressing
2:22
Crossdressing Role Reversal Marriage || Crossdresser C…
63.4K viewsNov 9, 2022
YouTubeTransgender and Crossdressing Hub
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