Maid Anna Fetish Videos & Clips
I'm Maid Anna, and I'm here to put you through a proper sissy training program. I love the process of feminization and gender transformation. I'll make sure you're made to crossdress while you learn your place in a female supremacy world.
If you're a submissive, I'll keep you locked in chastity so you can focus on your transformation fetish. I specialize in ebony female domination and femdom pov clips that leave you feeling like one of the sissy sluts.
I'm a dominatrix who enjoys sissy humiliation and submissive / slave training. You'll spend plenty of time on the floor for foot worship and foot massage. I'll use my feet to keep you in line, and maybe I'll reward your hard work with some face sitting if you're a good sissy maid.
My femdom mistress style is a double domination approach to your gender transformation fantasies.
Maid Anna Fetish Videos & Clips
I'm Maid Anna, and I'm here to put you through a proper sissy training program. I love the process of feminization and gender transformation. I'll make sure you're made to crossdress while you learn your place in a female supremacy world.
If you're a submissive, I'll keep you locked in chastity so you can focus on your transformation fetish. I specialize in ebony female domination and femdom pov clips that leave you feeling like one of the sissy sluts.
I'm a dominatrix who enjoys sissy humiliation and submissive / slave training. You'll spend plenty of time on the floor for foot worship and foot massage. I'll use my feet to keep you in line, and maybe I'll reward your hard work with some face sitting if you're a good sissy maid.
My femdom mistress style is a double domination approach to your gender transformation fantasies.
Maid Anna XXX Latest Videos
Stepmommy's naughty panty sniffing sissy: custom
9/28/25 9:35 PM•20 min•1003 MB•mp4•720p
Stepmommy's naughty panty sniffing sissy: custom
9/28/25 9:35 PM•20 min•1003 MB•mp4•720pPrice$25.99 USDStoreMISTRESS AVA BLACKCategoryEbony Panty FetishRelated CategoriesBarefoot,Panty Fetish,Panty Heads,Panty Stuffing,Sissy SlutsKeywordsMistress Ava Black,Stepmom Fantasy,Foot Gagging,Foot Worship,Foot Addict,Foot Slave Training,Panty Humiliation,Foot Domination,Foot Sole,Foot And Feet,Foot Humiliation,Bnwo,Female Supremacy,Submissive,Barefoot HumiliationPerformersMaid AnnaDescription"
The video begins with you on the phone speaking with your husband who is out of town. He says that he'll be away for a while longer and that you would still have to look after your stepson. This disappoints you since you think your stepson is a pathetic loser.
Next scene, you tell him the news and that you're still in charge. Stepson gets an attitude by saying that you're not his stepmom and walks away. You sigh in calm frustration after he walks away.
Next scene, you walk to your bedroom and see stepson through the door sniffing your panties while masturbating.
You take a photo of him and tell him that he is now your sissy bitch or else you will expose him.
You make him strip, put on a chastity and change into a short sissy dress with his cage out showing for you to tease and poke.
You make him do humiliating sissy tricks and have him hump your leg while sniffing your panties to make his cage hurt.
Next, you walk him to the sofa to have him worship your feet.
Sniff your shoes, feet and lick your soles and inbetween your toes.
You gag him a bit as well.
You tell him that he sucks well and might have him suck cock for you on the streets for money.
In the end, you put a collar on him and tell him that he's yours forever and walk him away on a leash.
You verbally humiliate him throughout the whole clip. Tell him that you only married his stepdad for his money and cheat.
For the worship scene, have close enough camera shots with your face and him licking your soles in single shots"

Mistress gets footrubs and sits on sissy's face
7/22/25 9:15 PM•28 min•1412 MB•mp4•720pPrice$34.99 USDStoreMISTRESS AVA BLACKCategoryEbony Female DominationRelated CategoriesChastity,Ebony Ass Worship,Face Sitting,Female Domination,Sissy TrainingKeywordsC4scuckolding25,Mistress Ava Black,Bnwo,Femdom Mean,Sissy,Sissy Maid,Ebony,Sissy Exposed,Sissy Humiliation,Dominatrix,Domme And Sub,Femdom Mistress,Sissy Slave,Total Power Exchange,Female SupremacyPerformersMaid AnnaDescriptionIn “sissies know what Mistress’s feet want” Mistress received a footrub that made her smile.
So she sat on sissy’s face and made her worship her huge dominant curves
What a lucky sissy!

Mistress rides sissy face
7/8/25 8:15 PM•14 min•1177 MB•mp4•720pPrice$15.99 USDStoreMISTRESS AVA BLACKCategoryFace SittingRelated CategoriesChastity,Ebony Ass Worship,Ebony Female Domination,Female Domination,Sissy TrainingKeywordsC4scuckolding25,Mistress Ava Black,Bnwo,Femdom Mean,Sissy,Sissy Maid,Ebony,Sissy Exposed,Sissy Humiliation,Dominatrix,Domme And Sub,Femdom Mistress,Sissy Slave,Total Power Exchange,Female SupremacyPerformersMaid AnnaDescriptionSissy is going to get a treat today
Mistress wants to ride on her face
Not that sissy minds
In fact her clitty starts to rise at the very thought of it
That is, until Mistress drops the chastity bombshell!
- 7/4/25 1:45 AM•10 min•819 MB•mp4•720p

Happy 4th of July Facesitting
7/4/25 1:45 AM•10 min•819 MB•mp4•720pPrice$12.99 USDStoreMISTRESS AVA BLACKCategoryFace SittingKeywordsC4scuckolding25,Mistress Ava Black,Mistress Brianna Olivia,Ass Worship,Facesitters,Gimp,Dungeon,Face Sit,Bdsm,Dominatrix,Domme And Sub,BBW Face Sit,Femdom Facesitting,Total Power Exchange,Facesitting SmotherPerformersSaint Bull, Maid Anna, Brianna OliviaDescriptionWhat a lucky boi he is!
With that face that is quite literally made for sitting on!
Mistresses just can’t resist!
They want his face! And they want it now!
They ride him! They scissor his head and neck!
They trample him
Mmm! What a happy 4th of July facesitting it is for him!

sissies know what Mistress’s feet want
6/12/25 6:15 PM•14 min•1217 MB•mp4•720pDescriptionMistress has commanded her sissy to worship her feet
She must do a good job of it too
Will the sissy be pleasing and receive a facesitting reward?
Or will she disappoint and get caned?
Watch and find out
Sissypoo's first time in heels
5/30/25 2:15 PM•12 min•1038 MB•mp4•720p
Sissypoo's first time in heels
5/30/25 2:15 PM•12 min•1038 MB•mp4•720pPrice$15.99 USDStoreMISTRESS AVA BLACKCategoryFemale SupremacyPerformersMaid Anna, Brianna Olivia, poopooDescriptionLittle brave sissy
She's about to attempt walking in heels for the first time
What a brave feat for her
They're really not easy to stay upright in
Thank goodness she has Maid Anna to guide her through her first steps.
Like a protective sissy hen, she guides the young chick into the big brave world of sissification
No easy feat, especially as the two Bully Mistresses just want to hurt sissy
She is reprimanded for being too hairy, and Mistresses yank and pluck her hair
Humiliation follows as she is made to twerk for Mistresses while getting spanked
For failing to follow the rules sissy is in for a world of hurt!
Well deserved
- 5/26/25 2:15 AM•11 min•913 MB•mp4•720p

Maid Anna’s sissy assessment
5/26/25 2:15 AM•11 min•913 MB•mp4•720pPrice$15.99 USDStoreMISTRESS AVA BLACKCategoryMaid FetishRelated CategoriesDouble Domination,Female Domination,Made To Crossdress,Sissy Training,Submissive / Slave TrainingKeywordsMistress Ava Black,Mistress Brianna Olivia,Maid,Dungeon Session,Femdom Handmaid,Sissy Maid,Sissy Humiliation,Maid Uniform,Curtsey,Sissy In Heels,Sissy,Crossdresser,Feminization,Sissy TransformationPerformersMaid Anna, Brianna Olivia, poopooDescriptionMaid Anna is put through her paces by the stern double Domme team of Mistress Brianna Olivia and Mistress Ava Black
Will she make the cut or fall short?
Watch and find out
- 5/19/25 12:41 AM•23 min•1151 MB•mp4•720p

A sissy performance review
5/19/25 12:41 AM•23 min•1151 MB•mp4•720pPrice$21.99 USDStoreMISTRESS AVA BLACKCategorySissy TrainingRelated CategoriesCrossdresser,Female Domination,Feminization,Made To Crossdress,Submissive / Slave TrainingKeywordsMistress Ava Black,Mistress Brianna Olivia,Walking In High Heels,Sissy Assessment,Female Supremacy,Dungeon Sessions,Femdom,Femdom Chastity,Dominatrix,Femdom Porn,Sub And Dom,Femdom Humiliation,British Femdom,New Femdom Video,Femdom SlavePerformersMaid Anna, Brianna Olivia, poopooDescriptionIt's time for sissy Maid Anna’s performance review
She had been working very hard to please Mistress, and she hopes that her efforts to be more feminine are beginning to bear fruit.
As the review commences Anna’s clitty makes a surprising statement of its own. By rising once her lace knickers are lowered. That will never do!
Marks deducted for that!
Next is assessing for bodily hair
Then her feminine walk is under scrutiny, as well as her curtsey
Then Anna is asked to show how she would entertain Mistresses’ friends
Her general cleaning skills are also put under the microscope by these two demanding Dommes
Maid cuntybunty gets a sockful of humiliation - full clip
4/30/25 10:00 PM•22 min•1122 MB•mp4•720p
Maid cuntybunty gets a sockful of humiliation - full clip
4/30/25 10:00 PM•22 min•1122 MB•mp4•720pPrice$19.99 USDStoreMISTRESS AVA BLACKCategoryFemale DominationRelated CategoriesArmpits,Double Domination,Humiliation,Sock Smelling,SpittingKeywordsMistress Ava Black,Lady Mk,Verbal Humiliation,Sissy Humiliation,Sissy,Sissy Maid,Sissy Exposed,Sissy Training,Armpit Licking,Smelly Armpits,Made To Worship,Femdom Humiliation,Domme And Sub,Spitting On Face,Spit FetishPerformersMaid Anna, Brianna OliviaDescriptionCuntybunty is a filthy little slut
She is called in to get a mouthful of Mistress spit. She can use that as lube to suck on Mistress Ava's sock.
But she also has to put that tongue to good use licking Lady MK’s armpits.
All the filth
All the dirt
Right down the back of her throat
Humiliation upon humiliation
Cuntybunty soaks it up like the dirty bitch that she is
And when Mistresses shove both their feet in her mouth and ride her sissy face, cuntybunty gets a mega humiliation boner that just won't quit!
The true joy of a serving sissy maid
4/29/25 6:00 PM•13 min•1061 MB•mp4•720p
The true joy of a serving sissy maid
4/29/25 6:00 PM•13 min•1061 MB•mp4•720pPrice$14.99 USDStoreMISTRESS AVA BLACKCategorySissy TrainingRelated CategoriesDouble Domination,Female Domination,Humiliation,Spanking,Submissive / Slave TrainingKeywordsMistress Ava Black,Maid Anna,Mistress Brianna Olivia,Sissy Assessment,Sissy Spanking,Otk Spanking,Sissy Humiliation,Sissy Exposed,Dungeon Session,Sissy In Heels,Sissy,Femdom Humiliation,Femdom,Dominatrix,Female SupremacyPerformersMaid Anna, Brianna OliviaDescriptionWhat infinite joys may be realised by having a sissy maid. Mistress Ava Black and Mistress Brianna Olivia know just how to put their sissy maid to good use. From providing refreshments, giving footrubs, providing general entertainment, to providing stress relief when Mistresses give her a hard spanking.

Sissy’s peachy butt
4/27/25 3:00 AM•16 min•1375 MB•mp4•720p
