SafeSearch is filtering adult resultsTurn it off
Dare Yourself with These Crossdressing Challenges: Pushing the Boundaries of Gender Expression
1:21
Dare Yourself with These Crossdressing Challenges: Pushi…
74.9K viewsApr 27, 2023
YouTubeMTF AI LifeStyle
£20 Crossdressing Challenge – Dress, Shoes & Full Try-On Haul
10:14
£20 Crossdressing Challenge – Dress, Shoes & Full Try-On Haul
7.8K views2 months ago
YouTubeCrossdressing Lifestyle
Surviving 24 Hours In a Dress!? (MTF Crossdressing Story)
18:11
Surviving 24 Hours In a Dress!? (MTF Crossdressing Story)
6.5K viewsApr 10, 2025
YouTubeMy Life My Rules
Crossdressing as a girl for a day. Exercise, housework, new outfits and more!
6:49
Crossdressing as a girl for a day. Exercise, housework, new outfits …
37.5K viewsFeb 23, 2021
YouTubeKeira3327
Guy Tries Going Out in Glossy Pantyhose — Crossdressing Challenge
2:27
Guy Tries Going Out in Glossy Pantyhose — Crossdressing Chall…
25.1K views4 months ago
YouTubeAyunNet
From Suit to Skirt My 24 Hour Transformation Challenge [Crossdressing Stories/MtF Transition
19:54
From Suit to Skirt My 24 Hour Transformation Challenge [Crossd…
687 views3 months ago
YouTubeBecoming She
Crossdressing Challenge! 👗😂
0:06
Crossdressing Challenge! 👗😂
105.6K views2 months ago
YouTubeMr Flippy
0:15
Become a Girl for a Day | MTF Challenge
709 views11 months ago
YouTubeLeggy Veronica
50:36
I Tried to Be a Full-Time Woman for 24 Hours It Broke Me! 😳💄 Crossdress…
350 views4 months ago
YouTubeFEMININE VIBES
20:22
Handcuffed Until I Dress as a Woman | Extreme Crossdressing …
66 views2 months ago
YouTubeZELIN
8:45
Transparent Dress Challenge Can You Actually Wear This?
6.1K views2 weeks ago
YouTubeCrossdressing Lifestyle
1:20
Crossdresser | Male to Female transformation | Cass | Dafni Girls
443.2K viewsMay 5, 2023
YouTubeDafni Girls | Crossdressing Studios | Spain
14:08
Truth or Dare | The Day I Transformed - A first time crossdr…
25.3K views7 months ago
YouTubeThe Gender Diary
32:05
Disciplined by Mom 👗🔒 (Crossdressing Stories – MtF Transition)
30.9K views7 months ago
YouTubeKinda Cute
9:50
Truth Or Dare: A First Time Crossdressing Experience
7.7K views3 months ago
YouTubePride Pulse🏳️‍🌈
25:06
Trapped In Skirts By Accident 😳👗 Crossdressing Challenge
370 views2 months ago
YouTubeGenderSwap Stories
8:13
Summer Upstairs - A first time crossdressing experience
479.8K views8 months ago
YouTubeBecoming Lacey
17:28
Can We Dress You Up!? (MTF Crossdressing Story)
48.2K viewsJan 28, 2025
YouTubeMy Life My Rules
20:31
Switching Places With My Wife (MTF Crossdressing Story)
12.9K viewsMar 21, 2025
YouTubeMy Life My Rules
18:12
I Made My Husband a Drag Queen , The Honeymoon Makeover - A cro…
20.7K views7 months ago
YouTubeThe Gender Diary
5:03
The Dare That Changed My Life Forever | Part 1 (Crossdressing St…
20.6K views7 months ago
YouTubeThe Transformation Diaries
18:46
Would my brother agreed to dress up as a girl for Halloween? | Male t…
3.4K views4 months ago
YouTubeCrossdressing Story
6:58
Midnight Drive: First Public Outing - MTF Crossdressing Story (Summe…
12.5K views4 months ago
YouTubeBecoming Lacey
9:41
Sissy Training Challenge: Can You Handle These Tasks?
28.9K viewsOct 12, 2024
YouTubeHelena
5:32
❤️ A task for SISSY for 1 day!
44.8K viewsJun 22, 2024
YouTubeJulia U
18:30
Trying On Dresses for the First Time [Crossdressing Stories / MtF Tran…
25.4K viewsNov 20, 2024
YouTubeBoys2Fem
10:10
My first public crossdressing in New York, 2024
145K viewsJan 17, 2024
YouTubeAbout TG Life
9:15
10 Joyful Activities Crossdressers Can Do
36.4K viewsAug 21, 2024
YouTubeAbout TG Life
4:21
Crossdressing Event | Dafni Girls
210.9K viewsMay 4, 2016
YouTubeDafni Girls | Crossdressing Studios | Spain
36:00
From Man to Woman in 24 Hours! [Crossdressing Stories / MtF Tran…
52K viewsSep 20, 2024
YouTubeBoys2Fem
See more videos
Static thumbnail place holder