TopVintage - 50s Cross Dress in Black
0:12
TopVintage - 50s Cross Dress in Black
28.4K viewsMar 5, 2015
YouTubeTopvintage Boutique
Stylish & Bold: Watch a Crossdresser Shine in a Vintage Red Dress!
4:10
Stylish & Bold: Watch a Crossdresser Shine in a Vintage R…
11.4K viewsNov 8, 2024
YouTubeCrossdressing Lifestyle
Crossdressing a Retro Look – How to Crossdress in Vintage Style from Start to Finish!
5:31
Crossdressing a Retro Look – How to Crossdress in Vintage Style fro…
15.6K viewsMar 2, 2025
YouTubeCrossdressing Lifestyle
Exploring 1950s Vintage Crossdresser Fashion
0:28
Exploring 1950s Vintage Crossdresser Fashion
1.5K viewsSep 13, 2021
TikTokdannybeaton
Crossdresser's Bbonlinedress's 1950s Vintage Polka Dots Pinup Retro Rockabilly Dress Try on Haul
5:20
Crossdresser's Bbonlinedress's 1950s Vintage Polka Dots Pinup R…
354 viewsNov 24, 2022
YouTubeMy Feminacy Complement Plan
Vintage Feminine outfit for Crossdressers
0:55
Vintage Feminine outfit for Crossdressers
105.2K viewsApr 24, 2020
YouTubeMiss Cookie Monster
Crossdresser in a disco outfit, ready to revive the 70s – CrossDressing with Carmen
2:55
Crossdresser in a disco outfit, ready to revive the 70s – CrossDressing …
17.5K viewsJun 5, 2021
YouTubeCrossDresser Carmen
1:28
Vintage Dress crossdresser
2K viewsNov 7, 2022
YouTubeTrixy Deans
1:41
Beautiful Crossdresser Trying Out Vintage Dresses | Carla Navarro
6.4K viewsMay 14, 2023
YouTubeSomething New
0:55
Jessica wearing 1950s Style Halter-neck Dress (Crossdresser / Trans…
8.1K viewsApr 15, 2021
YouTubeJessica's Corner
1:49
Retro Fashion of a Crossdresser 15
149 viewsDec 29, 2022
YouTubeMy Feminacy Complement Plan
1:59
Retro Fashion of a Crossdresser 13
260 viewsDec 27, 2022
YouTubeMy Feminacy Complement Plan
0:29
Jessica wearing 1950s Style Halter-neck Dress 2 (Crossdresser / Tran…
3.7K viewsApr 22, 2021
YouTubeJessica's Corner
1:47
Retro Fashion of a Crossdresser 9
168 viewsDec 9, 2022
YouTubeMy Feminacy Complement Plan
1:24
Gorgeous Vintage fullslip crossdresser
3.2K viewsNov 2, 2022
YouTubeTrixy Deans
5:14
I Tried Vintage Fashion with Heels and Corsets
32.9K viewsNov 30, 2021
YouTubeCrossdressing Lifestyle
2:02
Crossdressing Vlogger Just Kate 1950s Style Red Dress fashion loo…
1.1K views10 months ago
YouTubeKathleen Dawson
6:05
Classic pinup outfit idea for crossdresser
63.5K viewsJul 14, 2020
YouTubeMiss Cookie Monster
6:35
Elegant Crossdresser Ep.46 - Classic 80's Secretary Style - Blou…
8.7K viewsFeb 22, 2025
YouTubeYours Since Sheerly
3:06
Crossdressing Glamour Vintage Style - Goodwood revival 2025
10.1K views5 months ago
YouTubeCrossdressing Lifestyle
4:07
Crossdressing Outfit of the Day A touch of Classic Art Yankel Feather
22.3K viewsMar 21, 2021
YouTubeCrossdressing Lifestyle
5:05
Vintage Crossdressing and having fun!
3 months ago
YouTubeBobbie's Beautiful World
0:12
Vintage Crossdresser and Femboy Style Exploration
10.1K viewsNov 6, 2021
TikTokand_mayhem_ensued_
1:45
Elegant long Dirndl with blue apron (Crossdresser)
1.5K viewsMay 29, 2020
YouTubeIsabelle Labelle's Fashion
1:13
50s Dress Crossdresser
4.3K viewsSep 17, 2021
YouTubeTrixy Deans
17:31
A 1953 Crossdreamer
5.9K viewsJun 25, 2019
YouTubeJack Molay
4:50
3 50s-style Dresses - Crossdresser Trans LGBT
2.6K viewsJan 11, 2025
YouTubeemily shadows
5:54
Transformation: One Man’s Cross-dressing Wardrobe
30.7K viewsNov 5, 2015
YouTubehomotopiafestival
2:11
Crossdresser modeling 1950's style dating dress on first day of 2024
6K viewsJan 4, 2024
YouTubemdolivetti
7:36
Vintage Outfit for crossdressers part II
60.9K viewsAug 20, 2020
YouTubeMiss Cookie Monster
See more videos
Static thumbnail place holder