Including results for crossdressers playing dress up.
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Crossdressers in Dresses & Skirts Vol. 14 (Mar. 18, 2024)
24:58
Crossdressers in Dresses & Skirts Vol. 14 (Mar. 18, 2024)
285.4K viewsMar 19, 2024
YouTubeFNewt's Crossdressing Lifestyle
Crossdressers in Dresses & Skirts Vol. 11 (Dec. 6, 2023)
12:56
Crossdressers in Dresses & Skirts Vol. 11 (Dec. 6, 2023)
33.3K viewsDec 7, 2023
YouTubeFNewt's Crossdressing Lifestyle
A crossdress plays with her new dress
0:47
A crossdress plays with her new dress
42.6K viewsNov 5, 2024
YouTubeNatasha Xdress
Crossdresser Summer Fashion Haul: Dress up With Me! (Feminization)
5:52
Find in video from 01:00Mod Style Dress
Crossdresser Summer Fashion Haul: Dress up With Me! (Feminiza…
58.8K viewsJun 18, 2021
YouTubeYoya Fabulosa
Crossdressing Party | Pass The Wig | Dafni Girls
3:08
Crossdressing Party | Pass The Wig | Dafni Girls
237.2K viewsApr 13, 2016
YouTubeDafni Girls | Crossdressing Studios | Spain
Two crossdresser guys enjoying themselves and getting dressed to go out 💅🏼
1:49
Two crossdresser guys enjoying themselves and getting dressed t…
108.6K viewsOct 24, 2024
YouTubeferya.acosta highheels
Crossdresser fashion show / 11 different dresses
7:07
Crossdresser fashion show / 11 different dresses
117.8K viewsJan 5, 2019
YouTubeCrossDressingLife
0:37
crossdressing Sissy dress up dressing like a little sissy princes…
176.8K viewsNov 22, 2014
YouTubeTamara Heidi
4:22
Crossdressers in Dresses & Skirts Vol. 4 (Nov. 7, 2022)
54.9K viewsNov 11, 2022
YouTubeFNewt's Crossdressing Lifestyle
1:00
DRESS UP! DRESS OUT! Crossdressing Confidence!
36.6K viewsFeb 12, 2022
YouTubeJasmine Page
10:47
The Dress Up Duo 👗 (Crossdressing Stories) PART 1
11.2K viewsJun 18, 2023
YouTubeKinda Cute
9:15
10 Joyful Activities Crossdressers Can Do
36.3K viewsAug 21, 2024
YouTubeAbout TG Life
2:08
Outfits for Crossdressers | Best of
42.1K viewsMar 11, 2022
YouTubeOlive La Strada
1:12
Sissy Feminization Task 2 Patreon - Beautiful Sissies & Crossdresser…
74.9K viewsSep 12, 2022
YouTubeTheSissyGuide-Feminization Training- Sissificat…
0:19
Dress to impress - crossdressing fun
618.1K viewsApr 19, 2023
YouTubeNastja Sherer • Your Favourite Crossdresser
5:14
Incredible Photos Of Feminine Crossdressers And Sissies That L…
205.5K viewsSep 19, 2021
YouTubeTheSissyGuide-Feminization Training- Sissificat…
2:39
My new favorite sissy dress 💕 👗
78.7K viewsJun 17, 2023
YouTubeChristy C
4:10
The Beauty of Crossdressers Genders | Cd Girls ♥
36.9K viewsMar 9, 2021
YouTubeCd Girls
6:56
Dress Up Time! Stream Highlights - Transgender / Crossdresser
13.8K viewsDec 8, 2017
YouTubeAvona Star
4:21
Crossdressing Event | Dafni Girls
210.7K viewsMay 4, 2016
YouTubeDafni Girls | Crossdressing Studios | Spain
3:05
[Lookbook] Crossdresser ladyfish with pleated skirt & high heel, fash…
407.3K viewsMay 12, 2023
YouTubeLadyFish's Horizon
1:44
Find in video from 01:08Dressing Up
A very girly Dress crossdresser
2.3K viewsNov 21, 2022
YouTubeTrixy Deans
4:31
Aunt’s Dress-Up Magic 🎀 Crossdressing Stories
28.3K viewsApr 9, 2025
YouTubeFitUstyle
10:08
Femme Boys Who Love To Dress Like Girls || Transformation Life
470.8K viewsMar 23, 2017
YouTubeTransformation Life
8:02
Outwitted into CROSSDRESSING [CROSSDRESSER STORY]
57.3K viewsJan 10, 2023
YouTubeLuna's Crossdressing Stories
1:41
Dressing Up: Crossdressing from Male to Female | Sami Lawrence
17K viewsApr 5, 2023
YouTubeSomething New
8:17
ROLE PLAY: Sister Caught You Crossdressing in Dress and Panty…
6.7K views7 months ago
YouTubeSoft Silky Secrets
2:17
Amazing Men Dressed As Women #7
27.3K viewsOct 3, 2022
YouTubeCrossdressing Shout-out 💋
1:29
Crossdressing | Dressing Service Valencia | Dafni Girls
216.6K viewsSep 9, 2019
YouTubeDafni Girls | Crossdressing Studios | Spain
2:01
Having some fun dressed in a dress and heels (Crossdresser/Transves…
7.8K viewsSep 20, 2021
YouTubeClare
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1:49
Two crossdresser guys enjoying themselves and g…
108.6K viewsOct 24, 2024
YouTubeferya.acosta highheels
0:50
Dress Up, Dance Up: Cross-Dresser's Solo Show
1.1K views2 weeks ago
YouTubeYue's Dance Power
1:00
DRESS UP! DRESS OUT! Crossdressing Confidence!
36.6K viewsFeb 12, 2022
YouTubeJasmine Page
0:47
Sissy boy in a frilly pink princess dress
43.5K viewsSep 22, 2020
YouTubeSissy F
0:06
Boys, Auntie Jenny is bored and wants you to play dres…
54.9K views4 months ago
FacebookJenny Raven Author
1:00
DRESS OUT! FEEL BEAUTIFUL! Crossdressin…
22.4K viewsFeb 11, 2023
YouTubeJasmine Page
1:23
Crossdresser Raquel - Wet look animal print dress.
56.5K viewsDec 31, 2022
YouTubeRaquel Steele
2:27
Crossdresser in a cute outfit for a date night – CrossDre…
36.1K viewsMay 26, 2021
YouTubeCrossDresser Carmen
0:27
Striking Crossdresser Showcases Stunning Gree…
945 viewsJun 3, 2023
YouTubeAnastasia Harris
2:39
My new favorite sissy dress 💕 👗
78.7K viewsJun 17, 2023
YouTubeChristy C
0:23
Crossdresser in Ultimate Sexy Office Party Dress #fe…
28.3K views3 months ago
YouTubeJoann Abernathy
0:16
feminized elegant crossdresser outdoor in sk…
8.7K views10 months ago
YouTubeChristina d ́Yvon
1:00
crossdresser in floral dress dancing for you!
13.2K viewsFeb 5, 2022
YouTubeirene dfgdf
1:48
beautiful crossdressers and travesties , men dressed a…
81.5K viewsJan 10, 2021
YouTubeLiliana Rosas
1:21
sexy Crossdresser
231.6K viewsApr 13, 2023
YouTubeCrossdresser laurence
0:07
Sissy French Maid Try-On 💖 Obedient & Adorable! Siss…
3.3K views3 months ago
YouTubeSissy Lux Crossdressing & Feminizati…
0:29
elegant crossdresser lady Christina d´Yvon shows of…
77.6K viewsJul 24, 2017
YouTubeChristina d ́Yvon
0:27
Bold and Beautiful: Crossdresser Stuns in Blu…
763 viewsJun 4, 2023
YouTubeAnastasia Harris
1:31
Crossdresser - girly summer outfit
10.9K viewsAug 4, 2023
YouTubeIsabelle Labelle's Fashion
1:46
Dressed for the night CD
20.3K viewsJan 11, 2023
YouTubeJolly CD
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