Including results for mature sissy.
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Crossdresser Party Dress #genderfluid #mature #mtf #legs #fashion #dress #heels #tights #cute #short
1:01
Crossdresser Party Dress #genderfluid #mature #mtf #legs #fashion #dress #heels #tights #cute #short
1K views3 months ago
YouTubeKathleen Dawson
How My Mom's Fantasy Is Changing Me Crossdressing Stories
6:16
How My Mom's Fantasy Is Changing Me Crossdressing Stories
1.8K views2 months ago
YouTubeSissy Candy
Stepping Into Sissyhood: Is It Right for You?
9:40
Stepping Into Sissyhood: Is It Right for You?
16K viewsJun 1, 2024
YouTubeAbout TG Life
60-year-old Crossdresser Feels Fabulous After Calibrating With Friends
2:15
60-year-old Crossdresser Feels Fabulous After Calibrating With Friends
91.1K viewsMay 30, 2021
YouTubeCrossdressing Lifestyle
elegant crossdresser as mature lady in satin bow blouse and pleated skirt
1:06
elegant crossdresser as mature lady in satin bow blouse and pleated skirt
33.1K viewsApr 16, 2023
YouTubeChristina d ́Yvon
Crossdressing Vlogger Comfortable Casual Dress
2:24
Crossdressing Vlogger Comfortable Casual Dress
300 views3 weeks ago
YouTubeKathleen Dawson
Crossdresser Hot Party Dress #genderfluid #mature #mtf #legs #fashion #sexy #dress #heels #shorts
1:01
Crossdresser Hot Party Dress #genderfluid #mature #mtf #legs #fashion #sexy #dress #heels #shorts
4 views1 month ago
YouTubeKathleen Dawson
20:50
Aunt Fulfilled My Lifelong Dream Of FEMINIZING Myself (Crossdressing Stories)
43.6K viewsJun 15, 2024
YouTubeSissy Maya
4:54
Crossdressing in dress and high heels #crossdressing #maletofemale #crossdresser #femboy (Myriam_cd)
11.6K views2 weeks ago
YouTubeMyriam_CD
13:02
Conditioned Into Becoming a Sissy by Mom - Feminization Stories
59.4K views7 months ago
YouTubeFem Life
7:54:18
8 Hours of Sissy Hypnosis | Feminization Affirmations Overnight
33.7K views10 months ago
YouTubeCrossdressing & Self Help Hypnosis Videos
5:10
Stop Confusing Crossdressers with Sissies
9K views7 months ago
YouTubeNastja Sherer • Your Favourite Crossdresser
1:32
Mature crossdresser wearing a blue hydrangea dress with a cardigan
135.8K viewsOct 5, 2018
YouTubeTammy Brown
12:07
Sissy Brainwash Loop | Deep Hypno Mindwipe & Sissy Programming
21.3K views1 month ago
YouTubeSissy Club
3:47
The Pink Frilly Knickers A True life story 1of2
8.8K views2 months ago
YouTubePetSissyMissykins
0:27
feminized sissy maid, boy to girl transformation
6.9K viewsMay 18, 2025
YouTubeChristina d ́Yvon
2:14
Crossdressing Vlogger Slinky Little Number
615 views2 months ago
YouTubeCrossdressing Vlogger Kathleen Dawson
1:36
My Son is a Crossdresser... PART 2 #crossdressing #femboy #comicdub
226.8K views1 month ago
YouTubeGenderPlay Books
16:39
Become a Woman |👠|Mesmerizing Sissy Hypnosis for Instant Femininity
27.9K viewsSep 18, 2025
YouTubemaeve sissyverse
13:08
My Teacher's Humiliating Punishment Transformed Me Into a Girl | Sissy School Story
16.1K views11 months ago
YouTubeSissy Lux Crossdressing & Feminization Stories
3:37
Ultimate Sissy Hypno Transformation | Obey and Embrace Your True Self
15.1K viewsOct 31, 2024
YouTubeGODDESSTEX
29:21
Sissy Hypno for when you're in Denial
58.3K views8 months ago
YouTubeSarah Black
0:09
🌸💙 Happy Toesday, my lovely sissies! 💙🌸
17.5K views2 months ago
YouTubeSissyTania
3:56
Crossdressing Vlogger I'm an Awful Human Being
293 views3 months ago
YouTubeCrossdressing Vlogger Kathleen Dawson
2:25
Natural Older Women Over 55 - Elegant Fashion for Older Women Part 304
42K views2 weeks ago
YouTubeTimeless Elegance
0:15
sissy maid training
51.3K views11 months ago
YouTubeJentheinnocent
6:07
Your Mistress Takes Control: Time to Be Feminized
32.8K viewsFeb 4, 2025
YouTubemaeve sissyverse
21:07
Male To Female - Are You Trying Turning Me Into A Sissy
21.5K viewsMar 29, 2024
YouTubeTransgender & Crossdressing Stories
12:51
Mom Found Son Wearing Her Clothes (Crossdressing Stories)
57.3K viewsApr 12, 2024
YouTubeSissy Maya
18:54
Mother's Pretty Sissy Part 2 - A Crossdressing Audio Story
14.9K viewsFeb 14, 2025
YouTubeJen Occasionally
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Short videos

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