Category Archives: anal

It’s Time for Your ‘Yoga Class for Sissies’ with Sadistic Stephanie

Leave a reply

“I’ve seen you staring at me at yoga, you pathetic little dreamer. Well, I’m starting a Sissy Yoga class for wimps and rejects – like you. First you need to put in your butt plug and ball gag. Then you can put on your panties before I put you through a series of humiliating poses I put together just for you, wussy…”

ste29_81213_still_0000_Layer 8 ste29_81213_still_0001_Layer 7 ste29_81213_still_0002_Layer 5 ste29_81213_still_0003_Layer 3 ste29_81213_still_0004_Layer 2 ste29_81213_still_0005_Layer 1

humiliatrix.com/join

High Risk Sissy Humiliation with Sadistic Sorority Bitch Missy

Leave a reply
“I’m home for winter break and you’re gonna be my sissy slave. You will do all the degrading tasks I have planned for you or I will expose your sissy ass to everyone. You can start by lubing your new butt plug with the cum from my boyfriend’s dirty condom. Be a good sissy for Missy and I will let you frig off like a girl..” 15 minutes
Princess Missy from www.humiliatrix.com
Now showing at Humiliatrix.com

Missy Threatens to Turn Your Precious Princess into Her Cock Slut

Leave a reply
“I met your precious princess at a college party. I got her drunk, fingered her, spanked her, and fucked her with my strap-on. Now she wants to go lesbian for me. She’ll do anything – lick dog food off my boots, quit school… But I won’t dump your little whore unless YOU take over for her. Bend over, dahdeekins…” 11 minutes
Princess Stephanie from www.humiliatrix.com
Now showing at Humiliatrix.com

Miss Kendra Makes You Do It Like a Sissy

Leave a reply
When Miss Kendra snaps on a latex glove you know you are about to have your must vulnerable places invaded and manipulated. Miss Kendra has used her latex-gloved fingers to interrogate you, violate you and break you. Today, Miss Kendra is going to make you orgasm without touching your ‘boy bits.’ You will learn to cum by being finger-fucked from behind – like the squirming sissy you are. 7 minutes. 
Kendra James from www.humiliatrix.com
Now showing at Humiliatrix.com

Meet Princess Missy’s Wicked Middle Finger

Leave a reply
When a humiliatrix puts on spike heel boots and shiny black gloves you know you are about to be severely humiliated. You might get your face slapped raw, your cock and balls abused, or you might experience THIS. Missy brings you into her bedroom to challenge your masculinity. Pass the ‘glove test’ and you can fuck Missy. But if Missy’s middle finger wins, you will experience the ultimate emasculation. 14 minutes. 
Princess Missy from www.humiliatrix.com
Now showing at Humiliatrix.com

Panties and Punishment Fucking by Jaycee

Leave a reply
Your gym trainer Jaycee warned you. Act like a little bitch and you’re gonna get treated like a little bitch. And then you dumbly decided to get all ‘macho man’ in front of Jaycee’s girlfriends. Well, you’re not so tough when kickboxer Jaycee is strapping on a dildo. Are you, little mister sassy mouth? Better put on your wussy panties and apologize. Cuz you’re about to get schooled and fucked by a girl. 5 minutes. 
Princess Jaycee from www.humiliatrix.com
Now showing at Humiliatrix.com

You Will Cum Like a Girl for Miss Kendra

Leave a reply
Miss Kendra continues to prepare you for your sissy punishment fucking by teaching you to cum like a girl. Miss Kendra forbids you from touching your silly, worthless “boy parts.” Instead, Mistress makes you use a penis-shaped vibrator to deeply penetrate your sissy-clitty, until you begin to squirm, squeal and beg to make a girlie cummy for Miss Kendra, as she teases and encourages you. 10 minutes.
Kendra James from www.humiliatrix.com
Now showing at Humiliatrix.com

Strap-on Punishment Prep with Miss Kendra

Leave a reply
To prepare you for the punishment fucking she’s going to give you with her massive strap-on dildo, Miss Kendra is making you wear a big fat butt plug. You can either try to impale yourself – to entertain Miss Kendra with your comical struggles. Or you can learn the meaning of the word ‘humiliation’ and ask Miss Kendra to insert the plug for you. Either way will leave you no ‘wiggle room’ for humility. Not when Miss Kendra commands you to ‘sit.’ 7 minutes. 
Kendra James from www.humiliatrix.com

Now showing at Humiliatrix.com

Shave and a Tampon: Miss Kendra Leaves You Smooth & Emasculated

Leave a reply
Miss Kendra shreads you of your last vestiges of manhood. She shaves your legs and pubies sissy smooth – and then impales you with a tampon. You are about to become 100 percent girly from the waist down! Add stockings and a pair of panties and you are all ready to be sent out into the world – as a swooshy-silky sissy beneath your laughable manly exterior.  5 minutes.

Kendra James from www.humiliatrix.com


Now showing at Humiliatrix.com

Dr. Kendra Coerces You to Confess Your Most Embarrassing Secrets

Leave a reply
Dr. Kendra knows that you have been less than candid in your therapy sessions. Dr. Kendra puts on a pair of elbow-length black gloves while encouraging you to tell her the truth – no matter how embarrassing and how humiliating. Otherwise, Dr. Kendra will need to “extract” your confession using the traditional method. By lubricating her middle finger and… 
 
Kendra James from www.humiliatrix.com
 
 
Now showing at Humiliatrix.com