https://www.freepornflix.com/categories/sissy-training/ Thu, 23 Apr 2026 09:33:15 UTC https://www.freepornflix.com/video/876913/i-customize-my-sissy/
I love to play with my sissies and i want to completely erase the masculinity of the one at my feet. i'll start by replacing her cock with a perfect little clit then change her as i desire from head to toes. i'll make a beautiful makeup and nails before dressing her like my doll. all for my pleasure and my satisfaction before playing with my toy. but i also love to see her happiness while slowly becoming herself and let her sissy side fully exist.? to keep things interesting, i recommend the following videos :makeup tutorial : do your makeup like urfavoritegoddessmy sissy offers me her anal virginityhis first cei? key words ?sissy, gentle, makeup, sissy task, softcore, first time, crossdressing encouragement, femboy, feminization, transformation ]]> Wed, 22 Apr 2026 10:27:31 UTC https://www.freepornflix.com/video/876913/i-customize-my-sissy/ https://www.freepornflix.com/video/875025/kinky-bitch-sissy-training-1/
Her new sissy slave has now been in captivity for several weeks. chained up, handcuffed, ankle cuffs, gagged and masked it is yet to meet it's mistress's exacting standards of servitude. mistress has it dressed in it's new uniform, high healed locked on boots, a heavy, itchy wool skirt, a strict formal blouse tightly buttoned up to the neck, an itchy hessian apron, and of course a permanant mask and itchy wig. see the latest cruel goings on at mistress's home.     ]]> Tue, 21 Apr 2026 10:47:54 UTC https://www.freepornflix.com/video/875025/kinky-bitch-sissy-training-1/ https://www.freepornflix.com/video/874343/sissy-training-task-april-26/
Do you know i've already planned enough sissy training tasks to see us through til 2029? that's how important i think your training is. some of these are more humiliating, some humbling, some more about exploring feminine experiences. this is a feminine experience for you and perhaps you'll make a habit of this, all good girls should. ]]> Tue, 21 Apr 2026 10:09:15 UTC https://www.freepornflix.com/video/874343/sissy-training-task-april-26/ https://www.freepornflix.com/video/872790/4k-femcock-vs-vibrator-round-8-intimate/
Cute girl + huge cock + vibrators + fuckable outfit + moan loud + cum bad = femcock vs vibrator round, it's perfectly lewd. the only thing missed is your cum, jerk to this set now i promise you will have an orgasm like me. ]]> Mon, 20 Apr 2026 10:42:04 UTC https://www.freepornflix.com/video/872790/4k-femcock-vs-vibrator-round-8-intimate/ https://www.freepornflix.com/video/872498/sissified-hole/
I like my playthings to be pretty! i dress this one up like a slutty bimbo for my entertainment before i fuck it's throat. it's going to need to learn how to use it's holes for my enjoyment ]]> Mon, 20 Apr 2026 10:19:14 UTC https://www.freepornflix.com/video/872498/sissified-hole/ https://www.freepornflix.com/video/872391/hot-girls-have-the-best-cocks-strap-on-pov/
There's no need for words, just my bbc hot girls have the best cocks.             for more strap on video's click here for more female  domination video's click here for more lesbian domination video's click here ]]> Mon, 20 Apr 2026 10:13:21 UTC https://www.freepornflix.com/video/872391/hot-girls-have-the-best-cocks-strap-on-pov/ https://www.freepornflix.com/video/867777/high-heel-sissy-slave-training/
This was a custom cliplisten well to this clip slave as i will be giving you a brief introduction to the luxury tights and pantyhose i like and enjoy wearing. and i expect you to follow suit and obey me. after the intro, i will be dressing you up all nice and pretty, as the perfect sissy, and i demand you to wear high heels and learn how to walk in them as we will be going shipping and don't want you slowing down my valuable shopping time. listen well as you will be evaluated very very soon. ]]> Sat, 18 Apr 2026 09:58:19 UTC https://www.freepornflix.com/video/867777/high-heel-sissy-slave-training/ https://www.freepornflix.com/video/867225/panty-dare-gone-wrong/
This started as a silly little dare, but then... you clearly loved it. your arousal is so obvious to me. i notice it all, and lucky (or not lucky?) for you, i'm quite experienced with this. more pairs of panties, more arousal, until suddenly you're completely lost and fully obedient. this is more than just a dare now, it quickly becomes your lifestyle. you belong in panties, and we both know it! ]]> Sat, 18 Apr 2026 09:22:11 UTC https://www.freepornflix.com/video/867225/panty-dare-gone-wrong/ https://www.freepornflix.com/video/861552/mp4-version-bimbology/
Mp4 version   welcome to a very important lesson in bimbology. what is bimbology? only the blueprint for the rest of your feminine life! take in the spirals, take in the mesmerizing glow of femininity. a glow you will maintain forever. your lesson will be learned through conscious and subconscious means as you listen to this file, ensuring your obedience and mindfulness as you experience your life through the eyes of a bimbo. stupid, air headed, pink obsessed, and utterly mindfucked. layered looping vocals included in this mind-numbing sissification file. ]]> Wed, 15 Apr 2026 10:33:49 UTC https://www.freepornflix.com/video/861552/mp4-version-bimbology/ https://www.freepornflix.com/video/860936/spanked-sissy-sucks-cum-off-dildo/
]]> Wed, 15 Apr 2026 09:45:45 UTC https://www.freepornflix.com/video/860936/spanked-sissy-sucks-cum-off-dildo/ https://www.freepornflix.com/video/860852/mistress-ayn-s-sissy-maid-fails-at-chores-so-she-punishes-his-nipples-and-ass/
This maid insists on dusting where mistress ayn is reading her book and then knocks over an important international femdom summit trophy. the sissy is banished to another room but when he knocks over a book, mistress ayn orders him to select a punishment tool, a riding crop, for his punishment. after repeated strikes with the crop to his nipples, she then pinches his slutty sissy nipples to add to his discipline. another round with the crop makes sure sissy understands how to properly perform his house cleaning duties. when he starts to cry, she knows he has learned his lesson and sends him off to complete his household chores. this clip includes: mistress ayn, sissy maid, humiliation, nipple play, domestic service, discipline, spanking, dominatrix, riding crop punishment, nipple pinching, femdom ]]> Wed, 15 Apr 2026 09:39:26 UTC https://www.freepornflix.com/video/860852/mistress-ayn-s-sissy-maid-fails-at-chores-so-she-punishes-his-nipples-and-ass/ https://www.freepornflix.com/video/860569/sissy-encouragement-i-know-what-you-are-wmv/
I'm wearing a dress that shows off my deep cleavage as i sit in front of you, gently smiling. in a soft voice i tell you, i know what you are: a sissy. with a calm and comforting tone i carry on, feminizing you and describing your deepest desires. i know you want to be pinned down by a real man, have your sissy slit filled by him, suck his musky, manly cock. i tell you all of this gently and encouragingly, looking at you endearingly and knowing your clit is straining at the thought of it all ;) wmv version ]]> Wed, 15 Apr 2026 09:08:06 UTC https://www.freepornflix.com/video/860569/sissy-encouragement-i-know-what-you-are-wmv/