Crossdressing in the office with my boss’s clothes
2:44
Crossdressing in the office with my boss’s clothes
3K viewsSep 13, 2022
YouTubeInes Crossdresser
Crossdresser executive outfits at work
2:27
Crossdresser executive outfits at work
16.9K viewsAug 6, 2023
YouTubeInes Crossdresser
Crossdresser outfits for the office
1:42
Crossdresser outfits for the office
4.3K viewsMay 6, 2022
YouTubeInes Crossdresser
Got a new dress.. boss thinks I look very good 🫢 #crossdressing #crossdresser #crossdress #femboy #mtf
0:24
Got a new dress.. boss thinks I look very good 🫢 #crossdressing #crossdresser #crossdress #femboy #mtf
3.9K viewsJul 1, 2025
TikTokcrossdresserfin
Office Sissies: Confidence is Key
1:03
Office Sissies: Confidence is Key
64.6K viewsMay 26, 2023
YouTubeSissyPink
Lady Boss Sassy Office Outfits
0:23
Lady Boss Sassy Office Outfits
28K viewsNov 16, 2021
YouTubeMel Cross
I went to the salon my boss recommends me #mtf #transformation crossdress #makeup #boytogirl #femboy
0:10
I went to the salon my boss recommends me #mtf #transformation crossdress #makeup #boytogirl #femboy
17.4K views11 months ago
YouTubeThe Male-to-Fabulous Project
1:40
Office Sissies: From Desk to Dinner Dresses
65.9K viewsFeb 21, 2023
YouTubeSissyPink
2:40
They caught their boss doing this... 💀 #Shorts
51.1K views4 months ago
YouTubeKiroTV
0:57
Helluva Boss but just Moxxie Cross-dressing #helluvaboss #fypシ #viral #moxxie #fypage
43.4K views3 months ago
YouTubemewnadja
0:06
Replying to @user9699516220231
29.3K views9 months ago
TikTokcrossda_boss
1:04
Office Sissies: Dress to Impress
16.2K viewsNov 5, 2023
YouTubeSissyPink
1:00
Crossdressing Let's Start The Weekend in style
12.3K viewsMay 17, 2024
YouTubeCrossdressing Lifestyle
0:52
Jessica Wearing Red Short Dress with Belt (Genderfluid / Crossdresser)
7.7K viewsApr 12, 2021
YouTubeJessica's Corner
0:22
Unleash Your Inner Stylist: The Ultimate Guide to Cross Dressing
1.4K views3 months ago
YouTubeThe Shadow Walk
0:16
A cross dressing Harley biker boss #funny
1K views9 months ago
YouTubeJameskamm
1:03
I asked the cross-dressing president some questions
474 views1 week ago
YouTube男装女子蔵馬くん
0:19
Dress to impress - crossdressing fun
649.7K viewsApr 19, 2023
YouTubeNastja Sherer • Your Favourite Crossdresser
0:36
Crossdressing Husband Caught By His Wife | Male to female transformation
57.7K viewsFeb 28, 2024
YouTubeCrossdressing Story
0:11
From Son to Daughter: Heartwarming MTF Transformation with Family Support
25.1K views8 months ago
YouTubeCrossdressing Story
1:27
Did Cross-dressing Help People Escape Slavery?
16.2K views11 months ago
YouTubePBS Origins
0:15
Dinner Dress Outfits for a Blessed Week
39.8K views5 months ago
TikTokcrossda_boss
0:23
When Mario and Link CROSS DRESS
19.6K views7 months ago
YouTubeGabasonian
0:48
Crossdresser outfit for the office
4.9K viewsMay 16, 2022
YouTubeInes Crossdresser
0:57
BRO HAD TO CROSS DRESS💔 #anime #shorts
7.6K views7 months ago
YouTubeOmoshiroi Recap
1:36
Man poses as executive woman
5.2K viewsMar 1, 2022
YouTubeInes Crossdresser
3:01
Why Cross-dressing Can Be Lucrative
158.1K views6 months ago
TikTokhaleesahbits
2:04
Coming Out as a Cross-Dresser | Why (or Why Not) to Share Your Truth
26.5K viewsApr 17, 2020
YouTubeHelene Barclay
0:58
Jessica Wearing Purple Low-cut Dress (Crossdresser, Genderfluid) #shorts
3.7K viewsMay 5, 2021
YouTubeJessica's Corner
1:00
Boy To Girl Transformation "Office Transvestite" 🔥🤎💛
12.3K viewsDec 30, 2021
YouTubeLiviah O.
See more
Static thumbnail place holder