petticoated1
2:10
petticoated1
444.3K viewsDec 4, 2007
YouTubesissysissy99
My First Petticoat
10:58
My First Petticoat
76.6K viewsFeb 4, 2021
YouTubeHead2Heelz
Transformation: Plumber to Princess
3:05
Transformation: Plumber to Princess
186.3K viewsMay 1, 2020
YouTubeheidiphox100
If Groomsmen Were Bridesmaids
7:49
If Groomsmen Were Bridesmaids
7M viewsOct 30, 2014
YouTubeBuzzFeedVideo
Little Boy Wears Dresses
0:31
Little Boy Wears Dresses
4.7K viewsOct 24, 2019
YouTubeCaters Video
Crossdressers in Prom Dress
2:25
Crossdressers in Prom Dress
479.3K viewsSep 16, 2016
YouTubeVanesa Tsukino
Crossdressing - Cute polka dot dress
2:31
Crossdressing - Cute polka dot dress
55.5K viewsApr 16, 2020
YouTubeSierra Romeo
0:44
Sissy Guy Bride Dress
22.6K viewsMar 15, 2013
YouTubeMsAngelgirl522
38:50
Silly Sleepy Sissy Simp | SLEEPYTIME TRAINING | Female Supremacy University
191.9K viewsFeb 9, 2021
YouTubeFemale Supremacy University
7:54
MEN should wear DRESSES | Crossdressing
41.4K viewsOct 27, 2020
YouTubeOlive La Strada
1:55
Boy Dressed as Bride
16.9K viewsFeb 27, 2020
YouTubeCrossdressing Transformations
9:24
Rules to being a Sissy
224.2K viewsJun 29, 2017
YouTubeDomme Nation
13:59
DRESS BOY AS BARBIE STYLE ♡ MEET SOESBE!!!
49.9K viewsOct 20, 2019
YouTubeAzusa Barbie
1:40
UP10TION Gets Girly in Maid Costumes [MEET&GREET]
68.2K viewsOct 16, 2015
YouTubeMwave
1:59
Boy Dressed as Flower Girl
7.8K viewsApr 30, 2020
YouTubeFOREVER CROSSDRESSING
0:33
Sissy-Boy Christmas 2018 - Fashion
94.8K viewsNov 12, 2018
YouTubeSissy-Boy
2:36
Crossdressing #5 in a wedding dress
181.2K viewsApr 20, 2021
YouTubeWoman Crossdressing
1:24:38
Boys in Makeup & Dressing up - 3
450K viewsSep 21, 2017
YouTubevjjohn
7:07
Crossdresser fashion show / 11 different dresses
117.8K viewsJan 5, 2019
YouTubeCrossDressingLife
1:11
Satin sissy dresses from Sissy Maid Outfits!
317.8K viewsNov 7, 2011
YouTubecrossdresserbetty
8:18
Fashion Haul: Crossdress Male to Female Transformation (Feminization)
110K viewsMay 24, 2021
YouTubeYoya Fabulosa
9:48
I Dressed My Little Brother As Myself To Prank My Boyfriend! *HILARIOUS*
240.3K viewsDec 21, 2019
YouTubeAR Life
9:15
H&M Fall Fashion Haul: Crossdress Male to Female Transformation (pt.1)
69.9K viewsOct 11, 2020
YouTubeYoya Fabulosa
16:57
Amazon prime wardrobe outfit challenge / crossdresser try on
83.6K viewsApr 9, 2020
YouTubeCrossDressingLife
0:48
how a sissy should dress
35.3K viewsApr 22, 2021
YouTubeAdult Baby Nursery
9:07
My BROTHER becomes a GIRL for a Day 😜
28.4K viewsFeb 17, 2021
YouTubeThe Siblings
3:10
Dressing up as a Girl by Sister
62.6K viewsJul 31, 2020
YouTubeFOREVER CROSSDRESSING
33:28
Crossdresser closet haul try on 31 dresses
79.7K viewsJan 9, 2020
YouTubeCrossDressingLife
2:38
H&M Fall Fashion Haul: Crossdress Male to Female Transformation (pt.2)
100.6K viewsOct 16, 2020
YouTubeYoya Fabulosa
9:32
Boys Dressed as Sexy Girls in Public
35K viewsApr 22, 2020
YouTubeCrossdressing Transformations
See more