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Tag: SissyTraining - found 43 videos
Ruby_Onyx - My Perfect Kitchen Maid
Oh, the joys of having a live in sissy maid! I walk into a spotless kitchen to find him cleaning away for me. As he wilts beneath my heels and licks at the floor with his tongue, there's solid proof
Houseofdebauchery - Sissy Cuck films us fuck in Chastity
Mistress Electra Santiago wanted to give her slave the pleasure of filming us fuck while in chastity with the promise the promise of playing it over and over while it sat it in its cage. So
Ruby_Onyx - NEW CONTENT! Interviewing For A Sissy Maid
Finally I am interviewing my last sissy maid of the day! So she better be up to scratch and capable! A series of questions prompt pleasing answers and this sissy has lots of potential. She is good
ladyanaconda - Gerth Vador X Lady Anaconda Sissy Traini
Gerth Vador X Lady Anaconda Sissy Training Sofia Bun
Axel Reigns - Axel Reigns - TS Sissy Maid Boot Worship
Axel Reigns orders his TS sissy maid to clean his boots, she licks every inch, top and sole before being dismissed.
Adreena_Winters - Transforming My Sissy Into A BBC Slut
I know exactly how to transform this sissy into a slut for big black cock, and it all starts with my giant veiny strap on! Oh, doesn't she look fetching!? All dressed up in pretty clothes and girly
Ruby_Onyx - Prepping My Sissy Whore
My submissive little bitch kneels before me with his cock standing to attention! He thinks he might be receiving some pleasure of his own, but I have some more sinister plans! I am going to make
Axel Reigns - Axel Reigns - Sissy Uniform Inspection & BBC Fuck
Sasha De Sade gets her uniform inspected by Master Axel and pays the price with her mouth and asshole when she's not up to scratch. Watch her get stretched, used fucked hard and filled with cum by
HayleyQuinnxx - JOI CHASTITY CAGE
For you sissy sluts who deserve to be locked AWAY
ladyanaconda - Worship Black Kings - Cuckold POV
Don't you dream of being the cucky pet at the foot of Lady Anaconda's bed? Kneeling beneath Her and Daddys feet, eager to be of use to ensure your Superiors pleasure. You listen eagerly for
ladyanaconda - QOS Training for sissys
Train the weak beta Sissys to learn on how to serve BBC
LaBellaDiablaX - Bi Sissy Training
Bi Sissy Training! I'm moving on to my next step in training my sissy, feeding him big cock, will get him so addicted to having his hole used up by all my friends when I desire it but ya'll know he
LaBellaDiablaX - Texas Sunset Pegging
Pegging my slut as I enjoy the beautiful scenery the downtown Houston, Texas has to offer!!!
Adreena_Winters - Queen Adreena's Pegging Academy
Oh, look who’s back for more! In this deliciously deviant pegging session, Slave TT is desperate to prove he's worthy of my attention and what better way than bending over and taking my strap on
Axel Reigns - Axel Reigns - Anal Training & Creampie for Sasha De Sade
Sasha De Sade gets collared, gagged, fucked and made to eat cum from a bowl while in chastity.