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Free porn pictures 10 25 50 100 150 results per page   Search for: Filter by: Any size Small Medium Large Huge Anytime Today This week This month  Gallery Name   Images   Quality   Added    Sissymaid Shaunte with Mistress Jess    12   2025-09-27  Sissymaid Shaunte being used by Miss Jess cc_demented <30 fans>   Sissy Maid Michele - Pretty in Pink    3   2025-09-20  Sissy_Michele <175 fans>   Fake Magazine Covers    10   2025-09-11  Sissy_Michele <175 fans>   Sissy Maid Michele    8   2025-09-09  . Sissy_Michele <175 fans>   AI Sissy Maid Captions and Images: Cucked and Brainwashed    32   2025-08-23  Beta boi's bad spouse spices up their miserable marriage by making him a he-she slave for her big black bull. Mix of AI images with text of spotty spelling and captions with a loose narrative at best. ViennaSheraton <1,480 fans>   Sissy and Feminization Captions 43: Pansies in Peril 7    20   2025-08-16  A few reposts here. ViennaSheraton <1,480 fans>   Mistress Madeline's 30 days of feminization challenge Sissy mai    4   2025-07-28  A Sissy task thirty day feminization challenge that will be updated every day Mistressmadeli <30 fans>   Sissified and Feminized Cuckold Captions    24   2025-06-30  Sissy spouses and beta boyfriends are bested by belligerent bulls and forced to feminize by the wicked women in their lives. Their cringing cuckold condition isn't even their greatest shame as many meek males become tormented trannies, cucked... ViennaSheraton <1,480 fans>   Sena Sissy Maid    6   2025-06-28  Pics of feminized Sena as a Sissy Maid. Caption and repost are welcome senna106288 <79 fans>   Sissy Maid Rehabilitation AI Images - Rehab Facilities    72   2025-06-24  AI generated images and captions inspired by FEMINYZE-CAPTIONS' better captions, about a fantasy dystopia where sissy maids are being taught and brainwashed at rehab facilities. ViennaSheraton <1,480 fans>   Sissy Faggot Maid Humiliation    10   2025-06-11  tamis_demise <156 fans>   Sissy Cuckolds 41    314   2025-06-10  Feminized Sissy Cuckolds under the care and control of Cuckoldresses who have their best interests at heart engaging the help form other ladies with vested interests in seeing that any masculinity in the sissy cuckold is totally stamped out! sissycarla49 <2,425 fans>   AI Sissy Maid and Feminization Captions 4: Dominated by Dames    16   2025-05-30  Beta bois are forcibly feminized and frocked by fiendish females. Males made maids submissively serving superior senoritas. ViennaSheraton <1,480 fans>   AI Image Captions: Cuckold and Reluctant Sissy Maids    20   2025-05-11  Cuckolds are made meek maids are debased in the basement by dominant daddies and mocking mistresses. ViennaSheraton <1,480 fans>   Trapped in My Own Caps 2 - Neighbors    24   2025-05-04  Always take the time to get to know your neighbors. Except that weirdo tranny who makes bad porn captions. Avoid them. ViennaSheraton <1,480 fans>   Sissy Task #2 - Light up my life    5   2025-04-06  Master ordered me to slip a flash light up my bum then go outside at night and take photos of myself for his amusement! Maid_Teri <709 fans>   Sissy Task #1 - Light up my life    5   2025-04-06  Master ordered me to slip a flash light up my bum then go outside at night and take photos of myself for his amusement! Maid_Teri <709 fans>   Sissy Maid Rehabilitation AI Images - Indoctrination 2    48   2025-03-07  AI generated images inspired by FEMINYZE-CAPTIONS' better captions about a fantasy dystopia where sissy maids being taught and brainwashed. More garbled text. ViennaSheraton <1,480 fans>   French sissy maid Wanda    8   2025-02-18  Here are some of my pictures as a french maid.nAs you can see I like to wear french maid outfit, my clit is locked in chastity and I wear a steel anal plug.nI like bondage, so my high heels are locked too, I'm ball gagged and collar. Wanda_W <462 fans>   Elite Sissification and VIP Femdom Experience with Sissy Susy    28   2025-02-05  Step into a world of forbidden pleasures and surrender to the exquisite art of sissification. Sissy Susy (www.SissySyusy.com), the meticulously trained sissy maid, caters exclusively to VIP clients seeking an unparalleled blend of seduction and... escuelaparasis <1,259 fans>   My Life as a Sissy Wife for Daddy/Husband digger1989    690   2025-01-21  These pictures are most of my fantasies of being a sissy wife of Daddy/husband digger1989. If any picture violates your copyrights, pls. msg. me, I'll remove it without question. kendo2010 <970 fans>   AI Sissy Maid and Feminization Captions 3: Cucky Maids 2    16   2025-01-07  Medicore maid cuck captions of mediocre original AI images prompted by me. ViennaSheraton <1,480 fans>   AI Sissy Maid and Feminization Captions 2: Cucky Maids    16   2024-12-18  Captions of original AI images prompted by me. ViennaSheraton <1,480 fans>   Sissy Hilda's Chastity Maid Fun    10   2024-12-10  Sissy Hilda, locked in chastity, having fun as a sissy maid Sissy_Hilda <39 fans>   AI Sissy Maid and Feminization Captions 1    16   2024-12-10  Captions of AI images prompted by me. Yay. ViennaSheraton <1,480 fans> :: prev :: | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | :: next ::