A cross-dresser supported by a crossdressing Friend | Crossdresser with cross-dressing partner.
5:49
A cross-dresser supported by a crossdressing Friend | Crossdresser with cross-dressing partner.
95.4K views7 months ago
YouTubeAsmitha Transgender Library
Dressing Your Age As a Crossdresser: To Look Sophisticated, Not Silly
9:14
Dressing Your Age As a Crossdresser: To Look Sophisticated, Not Silly
2.1K views7 months ago
YouTubeMy Life My Rules
Crossdressing - Mature women 3
2:45
Crossdressing - Mature women 3
80.1K viewsSep 5, 2025
YouTubejulie1tca Mckoy
Dressed As an Older Woman Over 60 👗💅 (Crossdressing Stories)
18:13
Dressed As an Older Woman Over 60 👗💅 (Crossdressing Stories)
13.6K viewsNov 28, 2023
YouTubeKinda Cute
Crossdressing - Mature women 3
0:04
Crossdressing - Mature women 3
10.9K viewsAug 29, 2025
YouTubealecia mckoy
Why Being an Older Crossdresser is Actually a Superpower
8:16
Why Being an Older Crossdresser is Actually a Superpower
918 views2 months ago
YouTubeMy Life My Rules
Living as a Mature Woman Was My True Calling [Crossdressing Stories / MtF Transition]
29:08
Living as a Mature Woman Was My True Calling [Crossdressing Stories / MtF Transition]
29K viewsDec 19, 2024
YouTubeBoys2Fem
8:56
Beautiful cross-dressers outing in public places | Tips for going out cross-dressing - Episode 1
45.9K views4 months ago
YouTubeAsmitha Transgender Library
9:43
Mother Supporting their Son for Crossdressing
44.4K viewsOct 16, 2023
YouTubeAbout TG Life
20:44
I Finally Dressed as a Woman After 68 Years (Crossdressing Stories)
33.9K views7 months ago
YouTubeBoys2Fem
3:07
A young gayman crossdressing as a woman for her work as an influencer
12.9K viewsSep 22, 2025
YouTubeBarney Bear's Channel
15:02
From Mike to Melissa: Living in My Mom’s Fantasy [Crossdressing Stories / MtF Transition]
236.5K viewsNov 11, 2024
YouTubeBoys2Fem
5:46
I’m 23 - And In Love With A 57 Year Old Trans Woman | LOVE DON’T JUDGE
65.1K viewsOct 28, 2022
YouTubeLove Don't Judge
11:05
My Husband Wears My Clothes - A Crossdressing MTF Story
99.2K views6 months ago
YouTubePride Pulse🏳️‍🌈
2:40
Mature crossdressing 2
161.5K viewsJun 27, 2025
YouTubealecia mckoy
1:06
elegant crossdresser as mature lady in satin bow blouse and pleated skirt
33.1K viewsApr 16, 2023
YouTubeChristina d ́Yvon
1:39
Crossdresser | Male to Female transformation | Rebecca | Dafni Girls
489.1K viewsJan 11, 2023
YouTubeDafni Girls | Crossdressing Studios | Spain
4:34
A boy living as a girl from The USA meet this young beautiful crossdresser Ms Blaine
7.2K viewsMar 11, 2024
YouTubeBarney Bear's Channel
2:15
60-year-old Crossdresser Feels Fabulous After Calibrating With Friends
88.4K viewsMay 30, 2021
YouTubeCrossdressing Lifestyle
8:19
Crossdressers in beauty pageants | Woman-less beauty pageant
18.6K views5 months ago
YouTubeAsmitha Transgender Library
20:18
I Finally Wore a Dress at 71 Years Old (Crossdressing Stories)
5.4K views7 months ago
YouTubeBoys2Fem
10:56
The Ageing Crossdresser's Tips
9.6K viewsOct 14, 2024
YouTubeAbout TG Life
2:54
Crossdress As Woman If You're Over 40 Years Old
35.9K viewsMay 17, 2022
YouTubeAbout TG Life
0:28
51 year old transgender woman. Close up. x
102.7K viewsFeb 2, 2023
YouTubeDiane McCrae
8:13
Summer Upstairs - A first time crossdressing experience
631.4K viewsAug 13, 2025
YouTubeBecoming Lacey
5:53
I WAS A WOMAN - A Day of Crossdressing
301.7K viewsApr 6, 2016
YouTubeJayme Antonio Sejean
8:33
My Sister Found Me Wearing Her Skirt | Club of Two Ep. 1
87.1K viewsAug 20, 2025
YouTubeBecoming Lacey
3:49
A Different Look (Crossdresser)
64.1K viewsApr 8, 2025
YouTubestarrynowhere
3:52
Miriam meets 80-year-old transgender woman Francine | Miriam Margolyes: Australia Unmasked
60.1K viewsJul 20, 2022
YouTubeABC Entertainment
10:39
Advice for Crossdressers Over 60: How to Look Fabulous and Feel Confident
5.7K viewsFeb 1, 2024
YouTubeAbout TG Life
See more
Static thumbnail place holder