Including results for first time out crossdressing.
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"My First Time Crossdressing — I Never Expected This!"
2:09
"My First Time Crossdressing — I Never Expected This!"
79.5K views2 months ago
YouTubeTrans Girl🏳️‍⚧️
Clubbing In Heels: First Time Out (MTF Crossdressing Story)
17:34
Clubbing In Heels: First Time Out (MTF Crossdressing Story)
4.6K views8 months ago
YouTubeMy Life My Rules
Club of Two (episode 1) - A first time crossdressing experience
8:33
Club of Two (episode 1) - A first time crossdressing experience
62K views5 months ago
YouTubeBecoming Lacey
The First Time Wearing A Dress (MTF Crossdressing Story)
11:24
The First Time Wearing A Dress (MTF Crossdressing Story)
2.2K viewsOct 25, 2024
YouTubeMy Life My Rules
First Time Fully Dressed as a Girl Transformation Experience
0:06
First Time Fully Dressed as a Girl Transformation Experience
871.8K viewsAug 14, 2024
TikToktrappinbritt
Trying On Dresses for the First Time [Crossdressing Stories / MtF Transition]
18:30
Trying On Dresses for the First Time [Crossdressing Stories / MtF Tran…
23K viewsNov 20, 2024
YouTubeBoys2Fem
My First Time Out as a Girl [Crossdressing Stories / MtF Transition]
14:16
My First Time Out as a Girl [Crossdressing Stories / MtF Tran…
43.3K viewsAug 9, 2024
YouTubeBoys2Fem
14:38
The Mirror Moment - A first time crossdressing experience
6.4K views4 months ago
YouTubeThe Gender Diary
16:25
First Time As A Girl (MTF Crossdressing Story)
2.5K viewsDec 6, 2024
YouTubeMy Life My Rules
13:29
First Time Early Morning Park Walk As a CrossDresser
15.4K viewsJan 25, 2024
YouTubeAbout TG Life
17:20
How to Start Crossdressing - 5 Beginner Tips
17.9K viewsNov 22, 2024
YouTubeCatch Queen
19:49
My First Time Feminized (MTF Crossdressing Story)
9.7K views10 months ago
YouTubeMy Life My Rules
8:13
Summer Upstairs - A first time crossdressing experience
327.3K views5 months ago
YouTubeBecoming Lacey
5:22
How i started Crossdressing- bikini outfit
60.4K viewsJul 21, 2024
YouTubeMia Storm
11:21
The First Skirt That Was Truly Mine | Club of Two (episode 3) - A first ti…
16.4K views4 months ago
YouTubeBecoming Lacey
10:14
The Different Phases of Crossdressing
50.5K viewsAug 18, 2024
YouTubeAbout TG Life
6:58
Midnight Drive: First Public Outing - MTF Crossdressing Story (Summe…
6.1K views1 month ago
YouTubeBecoming Lacey
8:55
My first public crossdressing in London, 2024
7.8K viewsMar 26, 2024
YouTubeAbout TG Life
3:35
First Time Crossdresser in Hotel
5.3K views9 months ago
YouTubeLeggy Veronica
41:43
Glam Beyond Gender | My First Time Dressing as Her – An Unforg…
142 views4 months ago
YouTubeGlam Beyond Gender
15:02
From Mike to Melissa: Living in My Mom’s Fantasy [Crossdressing St…
185.3K viewsNov 11, 2024
YouTubeBoys2Fem
9:18
Day out Crossdressing with Wife
68K viewsNov 13, 2024
YouTubecrossdresser Nat
9:32
The Pros and Cons of Crossdressing at a Mature Age
106K viewsSep 14, 2024
YouTubeAbout TG Life
5:22
Crossdresser going out at night
63.9K viewsDec 27, 2024
YouTubeInes CD
14:08
Truth or Dare | The Day I Transformed - A first time crossdr…
23.7K views4 months ago
YouTubeThe Gender Diary
9:15
10 Joyful Activities Crossdressers Can Do
35K viewsAug 21, 2024
YouTubeAbout TG Life
15:10
First Time in Her Clothes - A Crossdressing Audio Story
10.2K views8 months ago
YouTubePride Pulse🏳️‍🌈
17:01
My Mom Wasn’t Supposed to Know - A first time crossdressing experie…
4.6K views3 months ago
YouTubeThe Gender Diary
4:39
Making Dreams Come True: A crossdressers Journey of self-dis…
22.9K viewsJun 16, 2024
YouTubeCrossdressing Lifestyle
30:35
He Said YES to Crossdressing Here’s What Happened
8.5K views4 months ago
YouTubeFemme Fantasy
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