SafeSearch is filtering adult resultsTurn it off
Crossdressing in secretary outfit
0:56
Crossdressing in secretary outfit
22.4K views3 weeks ago
YouTubecrossdresser Nat
Living As Boss's Personal Secretary [Crossdressing Stories/MtF Transition
29:43
Living As Boss's Personal Secretary [Crossdressing Stories/MtF Transi…
549 views4 months ago
YouTubeFemme Vision
Office Feminization Program Made Me Secretary?! 👩‍💼💄 (Crossdressing Stories – MtF Transition)
41:09
Office Feminization Program Made Me Secretary?! 👩‍💼💄 (Crossdressing St…
2.5K views1 month ago
YouTubeKinda Cute
Forced Into a Feminine Secretary Role (Crossdressing Stories)
16:18
Forced Into a Feminine Secretary Role (Crossdressing Stories)
243 views2 months ago
YouTubeCross Vibe
Forced Into Feminization as the Perfect Secretary – Crossdressing Stories
29:23
Forced Into Feminization as the Perfect Secretary – Crossdressin…
139 views3 months ago
YouTubeSophia Diaries
My Boss Didn’t Promote Me She Reprogrammed Me as Her Secretary [Crossdressing Stories/MtF Transition
59:28
My Boss Didn’t Promote Me She Reprogrammed Me as Her Secreta…
983 views4 months ago
YouTubeFemme Vision
Trapped by My Boss’s Plan—I Was Never Just His Secretary Crossdressing Stories
19:12
Trapped by My Boss’s Plan—I Was Never Just His Secretary Crossdre…
265 views3 months ago
YouTubeDani’s GenderSwap Stories
53:23
Encouraged To Become The Sissy Secretary - Crossdressing Stories
12.7K viewsNov 14, 2024
YouTubeSissy Maya
50:05
✨ Sissy Secretary: From Clumsy Intern to Office Queen! ✨ | MTF Fi…
709 views5 months ago
YouTubeFemme Fantasy
0:09
Crossdresser Secretary Outfit for New Job
810 views9 months ago
YouTubeLeggy Veronica
1:05:31
“From Office Guy to Her Perfect Secretary… My First Day in a Skirt 👗💋”
575 views6 months ago
YouTubeMaya Stories
26:24
🔥 I Went Undercover Crossdressing as His Secretary! - Crossdressing …
429 views8 months ago
YouTubeCrossdressing Stories Untold
12:59
My Boss’s Lesson Reshaped Me Into His Beautiful Secretary Voice …
734 views2 months ago
YouTubeMy Sissy World
0:07
The Perfect Sissy Secretary Skirt ✨ Feminine Fashion That Turns Hea…
1.9K views3 months ago
YouTubeSissy Lux Crossdressing & Feminization Stories
20:12
Mind Control Made Me My Boss’s Perfect Secretary 👠🧠 Crossdressing …
283 views2 months ago
YouTubeCharlotte Crosses Over
47:12
My Boss Didn’t Know I Was His Secretary Sissy Crossdressing St…
546 views4 months ago
YouTubeSissy Empress
1:26
Crossdresser in Secretary Outift
39.3K viewsMar 31, 2025
YouTubecrossdresser Nat
0:09
Crossdresser in Secretary Outift
37K viewsApr 15, 2025
YouTubecrossdresser Nat
35:48
I Just Wanted a Raise… Now I’m Her Secretary Crossdressedstory,Boy…
11.2K views9 months ago
YouTubeMiss Charlotte
0:14
Crossdresser in Secretary Outift
34.3K viewsApr 17, 2025
YouTubecrossdresser Nat
28:03
🩷👄🌸My Boss’s Punishment Made Me His Perfect Secretary [Crossdressing …
134 views7 months ago
YouTubeFeminization Tale
3:20
Crossdressing secretary
9.9K views7 months ago
YouTubePaige Darling
48:42
My Boss Hypnotized Me Into Her Perfect Secretary Crossdressing S…
3.2K views6 months ago
YouTubeFEMININE VIBES
27:04
Caught In Heels Hired As His Favorite Secretary Crossdressing …
1.5K views7 months ago
YouTubeFEMININE VIBES
22:00
First Day As A SECRETARY... In A SKIRT! 👠🖨️ (Crossdressing Stories …
9.1K viewsNov 25, 2024
YouTubeKinda Cute
0:10
Crossdresser in Secretary Outift
16.1K viewsApr 21, 2025
YouTubecrossdresser Nat
0:09
Crossdresser in Secretary Outift
9.3K viewsMay 19, 2025
YouTubecrossdresser Nat
17:44
The Secret Office Girl (MTF Crossdressing Story)
4.5K viewsDec 7, 2024
YouTubeMy Life My Rules
0:14
Crossdresser in Secretary Outift
9.1K views1 year ago
YouTubecrossdresser Nat
21:46
First Day As A SECRETARY... In A SKIRT! 👠🖨️ (Crossdressing Stories …
3.8K viewsNov 28, 2024
YouTubeKinda Cute
See more videos
Static thumbnail place holder