Including results for crossdresser in pencil skirts.
Do you want results only for Cressdresser in Pencil Skirts?
Feeling My Best: A Crossdresser's Lookbook of Pencil Skirt Outfits!
1:17
Feeling My Best: A Crossdresser's Lookbook of Pencil Skirt Outfits!
11K viewsJan 14, 2024
YouTubeNathar Sugarfree
Casual Vibes: Crossdresser Michelle Diaz's pencil skirt look!
2:24
Casual Vibes: Crossdresser Michelle Diaz's pencil skirt look!
7.4K views3 months ago
YouTubeMichelle Diaz
Crossdresser Out and About with Tight Pencil Skirt.
0:43
Crossdresser Out and About with Tight Pencil Skirt.
1.8K views1 month ago
YouTubejamie noir
Crossdresser Pencil Skirt | Glamour Boutique
0:23
Crossdresser Pencil Skirt | Glamour Boutique
36.3K viewsJul 4, 2022
YouTubeGlamour Boutique
Crossdresser, pencil skirt and high heels 💋
0:25
Crossdresser, pencil skirt and high heels 💋
2.4K views1 month ago
YouTubeSheila Velvet 💋
Leather Pencil Skirt and High Heeled Mary Jane Shoes - Glamorous Crossdresser #AlisonThighBootBoy
2:39
Leather Pencil Skirt and High Heeled Mary Jane Shoes - Glamorous Cro…
2.5K views1 month ago
YouTubeThe Sunday Girl - Alison ThighBootBoy
Leather Pencil Skirt #crossdresser #crossdressing
2:52
Leather Pencil Skirt #crossdresser #crossdressing
840 views5 months ago
YouTubeTrixy Deans
0:09
#crossdresser Laura wearing a pencil skirt. #mtf #boytogirltransfo…
23.6K viewsApr 25, 2025
YouTubeLaura
1:55
Leather pencil Skirt #crossdresser #crossdressing
671 views9 months ago
YouTubeTrixy Deans
1:04
Crossdresser in Pencil Skirt
28.3K viewsFeb 28, 2025
YouTubecrossdresser Nat
0:37
A very tight pencil skirt #crossdresser #m2fdressing #cro…
706 views11 months ago
YouTubeTrixy Deans
2:18
My favorite red pencil skirt #crossdresser #crossdressing
765 views6 months ago
YouTubeTrixy Deans
0:26
Crossdresser Pencil Skirt Beige | Glamour Boutique
4.9K viewsJul 4, 2022
YouTubeGlamour Boutique
2:40
Red Pencil Skirt #crossdresser #crossdressing
800 views7 months ago
YouTubeTrixy Deans
2:41
Pencil Skirt #crossdresser #crossdressing
509 views11 months ago
YouTubeTrixy Deans
1:25
Leather Pencil Skirt #crossdresser #crossdressing
906 views11 months ago
YouTubeTrixy Deans
1:08
Pencil Skirt and Slippers #crossdresser #crossdressing
595 views11 months ago
YouTubeTrixy Deans
3:10
Pencil Pusher (Transvestite / Crossdresser)
120.4K viewsAug 15, 2019
YouTubestarrynowhere
0:35
Blue Satin Blouse and pencil skirt #crossdresser #crossdressing
854 views6 months ago
YouTubeTrixy Deans
2:39
Rose Pink pencil skirt #crossdressing #crossdresser
447 views5 months ago
YouTubeTrixy Deans
36:00
Crossdressers in Dresses & Skirts Vol. 18 (Dec. 27, 2025)
50K views6 months ago
YouTubeFNewt's Crossdressing Lifestyle
7:38
Crossdressing: Black pencil skirt, corseted sweater, and leopard pri…
825 viewsJul 8, 2025
YouTubeSara Belle
3:40
Crossdresser Laura in a short denim skirt
8.8K views7 months ago
YouTubeLaura
4:50
Crossdresser Laura wearing an alluring maxi skirt
6.2K views10 months ago
YouTubeLaura
7:43
Crossdresser Laura wearing sexy leather skirt
29.8K viewsJul 9, 2025
YouTubeLaura
6:54
Crossdressers in Dresses & Skirts Vol. 10 (Dec. 1, 2023)
33.6K viewsDec 1, 2023
YouTubeFNewt's Crossdressing Lifestyle
0:26
Crossdresser in pencil skirt
11.9K viewsOct 2, 2024
YouTubecrossdresser Nat
0:16
Glamour Boutique- Crossdresser Pencil Skirt
6.6K viewsDec 5, 2024
YouTubeGlamour Boutique
0:43
Crossdresser pencil skirt
5K viewsMay 15, 2024
YouTubeInes Crossdresser
0:37
Crossdresser in Pencil Skirt
3.5K viewsMar 23, 2025
YouTubeVenusinleo
See more videos
Static thumbnail place holder

Short videos

1:17
Feeling My Best: A Crossdresser's Lookbook …
11K viewsJan 14, 2024
YouTubeNathar Sugarfree
2:24
Casual Vibes: Crossdresser Michelle Diaz's pencil skirt …
7.4K views3 months ago
YouTubeMichelle Diaz
0:43
Crossdresser Out and About with Tight Pencil Skirt.
1.8K views1 month ago
YouTubejamie noir
0:23
Crossdresser Pencil Skirt | Glamour Boutique
36.3K viewsJul 4, 2022
YouTubeGlamour Boutique
0:25
Crossdresser, pencil skirt and high heels 💋
2.4K views1 month ago
YouTubeSheila Velvet 💋
2:39
Leather Pencil Skirt and High Heeled Mary Jane Shoes - …
2.5K views1 month ago
YouTubeThe Sunday Girl - Alison ThighBootBoy
2:52
Leather Pencil Skirt #crossdresser #crossdress…
840 views5 months ago
YouTubeTrixy Deans
0:09
#crossdresser Laura wearing a pencil skirt. #mtf #boytog…
23.6K viewsApr 25, 2025
YouTubeLaura
1:55
Leather pencil Skirt #crossdresser #crossdress…
671 views9 months ago
YouTubeTrixy Deans
1:04
Crossdresser in Pencil Skirt
28.3K viewsFeb 28, 2025
YouTubecrossdresser Nat
0:37
A very tight pencil skirt #crossdresser #m2fdressin…
706 views11 months ago
YouTubeTrixy Deans
2:18
My favorite red pencil skirt #crossdresser #crossdress…
765 views6 months ago
YouTubeTrixy Deans
0:26
Crossdresser Pencil Skirt Beige | Glamour Boutique
4.9K viewsJul 4, 2022
YouTubeGlamour Boutique
2:40
Red Pencil Skirt #crossdresser #crossdress…
800 views7 months ago
YouTubeTrixy Deans
2:41
Pencil Skirt #crossdresser #crossdressing
509 views11 months ago
YouTubeTrixy Deans
1:25
Leather Pencil Skirt #crossdresser #crossdress…
906 views11 months ago
YouTubeTrixy Deans
1:08
Pencil Skirt and Slippers #crossdresser #crossdress…
595 views11 months ago
YouTubeTrixy Deans
3:10
Pencil Pusher (Transvestite / Crossdresser)
120.4K viewsAug 15, 2019
YouTubestarrynowhere
0:35
Blue Satin Blouse and pencil skirt #crossdresser #cross…
854 views6 months ago
YouTubeTrixy Deans
2:39
Rose Pink pencil skirt #crossdressing #crossdres…
447 views5 months ago
YouTubeTrixy Deans
Static thumbnail place holder