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On the High Seas, (and low) crossdressed
15:18
On the High Seas, (and low) crossdressed
25.2K views3 months ago
YouTubeheidiphox100
All Good Things ....Crossdresser on Cruise
4:41
All Good Things ....Crossdresser on Cruise
8.1K views1 month ago
YouTubeheidiphox100
Crossdressing In Public on a Cruise Ship
1:10
Crossdressing In Public on a Cruise Ship
9.6K viewsSep 8, 2023
YouTubeElizabeth Andrews
Cruising as a Girl
9:08
Cruising as a Girl
42.8K viewsMar 15, 2024
YouTubeheidiphox100
Cruising Sundresses
8:05
Cruising Sundresses
13.4K views3 months ago
YouTubeheidiphox100
Crossdressing in Thailand: Bangkok to the Jungle (Custom Suit + River Cruise)
10:40
Crossdressing in Thailand: Bangkok to the Jungle (Custom Suit + River Cruise)
4.5K views1 month ago
YouTubeCrossdressing Lifestyle
A cross-dresser supported by a crossdressing Friend | Crossdresser with cross-dressing partner.
5:49
A cross-dresser supported by a crossdressing Friend | Crossdresser with cross-dressing partner.
61.8K views2 months ago
YouTubeAsmitha Transgender Library
Cruise Nights/Wife Comments
18:28
Cruise Nights/Wife Comments
94.3K viewsFeb 9, 2024
YouTubeheidiphox100
Hot Male to Female Crossdresser on a Cruise Ship
1:52
Hot Male to Female Crossdresser on a Cruise Ship
1.4K views7 months ago
YouTubeElizabeth Andrews
"Is 'HE' a Girl?"
6:55
"Is 'HE' a Girl?"
40.4K viewsMay 3, 2024
YouTubeheidiphox100
The Feminized Picnic, I Was Paid to Wear Her Dress - A Crossdressing Story
25:39
The Feminized Picnic, I Was Paid to Wear Her Dress - A Crossdressing Story
40.2K views5 months ago
YouTubeThe Gender Diary
We Are Family
12:38
We Are Family
27K viewsApr 19, 2024
YouTubeheidiphox100
I Finally Dressed as a Woman After 68 Years (Crossdressing Stories)
20:44
I Finally Dressed as a Woman After 68 Years (Crossdressing Stories)
18.2K views3 months ago
YouTubeBoys2Fem
A Feminization Story: New Roommate - Part 2
10:00
A Feminization Story: New Roommate - Part 2
36.7K views7 months ago
YouTubeBecoming Lacey
Rock'n the Boat
12:34
Rock'n the Boat
22.7K viewsMar 29, 2024
YouTubeheidiphox100
Another short walk crossdressed in the parking lot
0:20
Another short walk crossdressed in the parking lot
850 viewsJan 15, 2025
YouTubeDenise Yssis
Crossdresser at the bus stop
0:37
Crossdresser at the bus stop
12.2K viewsJan 22, 2025
YouTubecrossdresser Nat
Crossdressing-walking around hotel
12:59
Crossdressing-walking around hotel
11.3K views10 months ago
YouTubeSam smith xx
Crossdresser Walking Outside (Walk With Me)
5:16
Crossdresser Walking Outside (Walk With Me)
29.2K views8 months ago
YouTubeMatilda Maiden
crossdresser walking around hotel in heels
18:47
crossdresser walking around hotel in heels
119.1K viewsAug 22, 2024
YouTubeSam smith xx
Crossdresser shops for clothes
1:23
Crossdresser shops for clothes
90.1K viewsJan 31, 2025
YouTubecrossdresser Nat
Crossdresser @jezebelform out in public. Walk by the harbor in a red miniskirt and high heels
6:19
Crossdresser @jezebelform out in public. Walk by the harbor in a red miniskirt and high heels
28.8K viewsMar 29, 2025
YouTubeJezebel Form
The Surprising Perks of Late-Night Crossdressing Walks
2:17
The Surprising Perks of Late-Night Crossdressing Walks
10.2K viewsMay 30, 2024
YouTubeCrossdressing Lifestyle
Summer Upstairs - A first time crossdressing experience
8:13
Summer Upstairs - A first time crossdressing experience
494.4K views9 months ago
YouTubeBecoming Lacey
The Hidden World of Cross-Dressing in the 60s [Crossdressing Stories / MtF Transition]
40:53
The Hidden World of Cross-Dressing in the 60s [Crossdressing Stories / MtF Transition]
24.4K viewsJan 22, 2025
YouTubeBoys2Fem
Crossdresser walks outdoors at night
0:39
Crossdresser walks outdoors at night
12.1K viewsDec 16, 2024
YouTubecrossdresser Nat
Crossdressing in Public: MTF Crossdresser Explores Downtown Vancouver in a Green Dress & High Heels
26:09
Crossdressing in Public: MTF Crossdresser Explores Downtown Vancouver in a Green Dress & High Heels
10.5K viewsJul 20, 2024
YouTubeAnastasia Harris
Crossdresser walks in park
0:59
Crossdresser walks in park
5.2K viewsFeb 26, 2025
YouTubecrossdresser Nat
Crossdresser walking in publoc
7:01
Crossdresser walking in publoc
19.1K viewsDec 31, 2024
YouTubeAroma D
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