Including results for day out crossdressed.
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Crossdressing - Ms Dee's Day Out Travel by Train To Shop until She Drops
3:34
Crossdressing - Ms Dee's Day Out Travel by Train To Shop until She Drops
9.6K viewsMar 30, 2024
YouTubeCrossdressing Lifestyle
Casual Crossdress Day Out ✨
0:18
Casual Crossdress Day Out ✨
3.2K views4 months ago
YouTubeKeira3327
A Day Out with Louise - Outdoor Transvestite Business Women
8:59
A Day Out with Louise - Outdoor Transvestite Business Women
68.8K viewsNov 10, 2018
YouTubeMira Murray
A day out crossdressing
0:47
A day out crossdressing
9K viewsApr 22, 2016
YouTubeAmber Auley
A Day Out In Manchester (Crossdressers / Transvestites)
4:50
A Day Out In Manchester (Crossdressers / Transvestites)
130.6K viewsJun 16, 2023
YouTubestarrynowhere
Crossdresser Goes Out - Gets in Trouble
16:50
Crossdresser Goes Out - Gets in Trouble
101.8K viewsMar 26, 2023
YouTubeCatch Queen
March Summer Sun for crossdressed day out
2:38
March Summer Sun for crossdressed day out
90.1K viewsNov 18, 2012
YouTubekayewinguk
2:36
M2F Katie's Crossdressing Adventure
108.1K viewsOct 28, 2021
YouTubeCrossdressing Lifestyle
12:22
5 Tips for Going Out While Crossdressed
15.7K viewsApr 22, 2023
YouTubeCatch Queen
3:39
Crossdressing in Public - Time for a night out!
134.2K viewsApr 18, 2022
YouTubeCrossdressing Lifestyle
6:00
Crossdresser Ana - Going outdoor day 117
64K viewsAug 30, 2025
YouTubeAna Hans
0:20
Crossdresser's Day Out
60.9K viewsAug 31, 2023
YouTubeCarly Blink
7:00
Daytime outing of a transvestite business woman
52.5K viewsMay 27, 2022
YouTubeMira Murray
2:40
First time out crossdressing
18.2K views5 months ago
YouTubeSam smith xx
5:06
Crossdresser Ana - Going outdoor day 92
62.8K viewsMar 13, 2025
YouTubeAna Hans
6:15
GailsFirstTripOutJan2016 (Crossdresser) Part 2
111.2K viewsFeb 27, 2016
YouTubeGail Jones
5:06
Transvestite Business Woman - May 2016 Daytime Outing
22.1K viewsNov 27, 2016
YouTubeMira Murray
4:26
Crossdresser Ana - Going outdoor day 67
9.5K viewsJan 25, 2024
YouTubeAna Hans
2:09
MY DAY OFF A Cross Dressing Mini Adventure
13.8K viewsJul 24, 2015
YouTubeBo Bo
2:14
Claire Bear's Day out
14.4K viewsSep 26, 2020
YouTubeClaire Watson
9:36
Crossdresser Ana - Going outdoor day 69
45.5K viewsJan 26, 2024
YouTubeAna Hans
1:55
Blue Dress on a windy day crossdresser
10.8K viewsFeb 19, 2022
YouTubeTrixy Deans
12:42
First Day Out at Work & Getting my Ears Pierced!!! ( MTF Transgender )
13.7K viewsJan 7, 2017
YouTubeIt's Emily!
2:53
Crossdresser Doki☆Doki☆Cosplay, Business Suit （Out of Office Work）
19.3K viewsNov 13, 2021
YouTubeCrossdresser Naomi
9:15
10 Joyful Activities Crossdressers Can Do
37.4K viewsAug 21, 2024
YouTubeAbout TG Life
21:18
The Day I Went Femme for a Business Trip [Crossdressing Stories / MtF Transition]
16.1K viewsNov 9, 2024
YouTubeBoys2Fem
6:29
Crossdresser Ana - Going outdoor day 73
17.9K viewsJun 9, 2024
YouTubeAna Hans
3:46
Moonlit Crossdressing: A Night of Elegance & Enchantment
12.4K viewsSep 28, 2024
YouTubeCrossdressing Lifestyle
3:01
One of the best days - Walking outdoor on high heels - Crossdresser
23.9K viewsApr 14, 2015
YouTubeHigh Hill
21:36
The Day I Logged In as Myself… and Logged Out as Janet
3.7K views8 months ago
YouTubeThe Gender Diary
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