SissyTraining

Date Views
background Goddess Joules Opia - Pretty Privilege
12:15

2026/01/273K Views
background BaileyWilde - First Time Man Dressed as a Woman
10:00

2026/01/272.4K Views
background BaileyWilde - Drag Transformation
09:59

2026/01/272.4K Views
background BaileyWilde - First Time Guy Crossdressed
02:25

2026/01/242.7K Views
background Goddess Joules Opia - Sissy Tasks 4
06:56

2026/01/242.6K Views
background BaileyWilde - First Time Crossdressing
10:00

2026/01/243K Views
background BaileyWilde - First Time Guy Dressed as a Girl
02:50

2026/01/232.4K Views
background femoby69 - femboy anal training
02:34

2026/01/222.9K Views
background EmilyAnalAcrobat - XXL Dildo vs Prolapsed Sissy Pussy - Teaser
01:59

2026/01/222.5K Views
background BaileyWilde - Purple Hair Crossdresser
02:35

2026/01/212.9K Views
background BaileyWilde - Roommate Convinces Man to Crossdress for Girl's Night Out
02:15

2026/01/212.6K Views
background BaileyWilde - Roommate Convinces Man to join Girls Night Out
02:17

2026/01/212.1K Views
background Maxxxine_ - Transformation
02:33

2026/01/212.3K Views
background BaileyWilde - Woman Convinces Man to Dress as Woman to do Girls Night Out
02:15

2026/01/212.3K Views
background BaileyWilde - Guy Gets Makeover for Girls Night Out 2
04:29

2026/01/202.9K Views
background BaileyWilde - First Time Dressed as a Blonde Woman
05:25

2026/01/202.3K Views
background BaileyWilde - Feminization Transformation to Get Maid Job
06:18

2026/01/202.4K Views
background BaileyWilde - Crossdresser Putting On Eye Shadow
04:39

2026/01/202.1K Views
background BaileyWilde - Crossdresser Doing Fake Eyelashes
04:26

2026/01/202.1K Views
background BaileyWilde - Sissy Training for Hotel Housekeeping Job
01:35

2026/01/192.5K Views
background BaileyWilde - MILF Transforms Man into Goth Woman
01:29

2026/01/192.5K Views
background trinity_infinity - Packing Up My Sissy Starter Kit
02:33

2026/01/192.6K Views
background Sissy Hope - Sissy Hope, thanks for your love Daddy
07:41

2026/01/152.7K Views
background Ria_Bentley - Ria Bentley Riding Dildo in Hallway & Cumming
02:36

2026/01/142.3K Views