Brianna has been training her son, Danielle, to become a sissy. She has selected romantic fiction for Danielle’s reading material. Appropriate literature is part of Danielle’s mental development, as he grows into an ideal sissy for his mother. Brianna calls Danielle into the room. Danielle has been dressed, head to toe in complete sissy garb. She wears a pink satin corset and pink garters to hold up her stockings. And of course, Brianna’s son has a pretty chastity to match the outfit. Brianna observes her son’s stride in high heels as she approaches. Danielle kneels beside mommy, and mommy pulls back her son’s wig to inspect the makeup application. Danielle has neglected to apply lipstick. Mommy corrects Danielle and reminds her that lipstick is very important for a good girl to wear. Brianna moves on to inspecting her son’s chastity. Danielle complains to her mother that she has been in chastity for a very long time. Brianna makes her son thank her for keeping her in the device. It’s for her own good. Danielle understands that mommy knows best, but doesn’t like that she must wear head to toe pink. She is especially frustrated with the pink stockings, which are sometimes itchy. Brianna is disappointed that her son has not yet learned to appreciate stockings. Brianna encourages her son to appreciate the softness of mommy’s stockings by massaging her feet. Danielle massages her mother’s feet. Brianna encourages her son to inhale the smell of her feet and kiss them. She reminds her son that training is necessary, because Danielle will be sent to her aunt, Alexandra for the summer. She wants Danielle to perform well at her aunt’s parties. Danielle complains. She hates spending summer with Aunt Alexandra. Alexandra spanks her, and it hurts. Brianna brushes aside Danielle’s complaints and starts to read to her from the romance novel. The novel helps mentally groom Danielle to be attracted to men. Danielle will appreciate the preparation once his mother and aunt start sending her out on dates. Danielle brings up the spanking again and complains to her mother that one-time Aunty Alexandra bent her over her knee and spanked her very hard. Danielle was upset and couldn’t sit for days. Brianna tells Danielle that she just needs to get used to receiving a hard spanking. Brianna pulls her son over her knee. She begins to strike her sissified son’s bottom one hundred times, compassionately, to prepare her for more extreme punishments from her aunt.

Penny Pax and Jane Wilde are attending Kenzie Taylor's Anal Academy. They sit at their desks in class, ready for their final anal exam. Before Professor Taylor shows up, the two have some nasty words with each other about who is the bigger slut on campus. Kenzie enters the room and yells at the girls to stop bickering at each other. The exam begins and Kenzie tells them to get on their knees in front of her and take her panties down only using their mouths. Kenzie tells them to lick her asshole and she judges who can do it better. Penny licks Kenzie's ass with the full length of her tongue while Jane watches, impatiently waiting her turn to tongue Kenzie's hole. Kenzie tells Jane to get on her desk and Jane quickly lays down on the desk and Kenzie sits on her face, smothering her nose and mouth with her asshole. Penny and Jane both lick her asshole while Kenzie uses an Hitachi on her clit and cums hard on their faces. Next, Penny gets bent over the school desk and Kenzie gets a big metal toy and pops it in and out of Penny's asshole while Penny licks Jane's ass. Jane, with her ass in the air, gets her ass filled with a clear acrylic toy, giving her big gapes. Kenzie puts matching purple butt plugs in each of their asses and face-fucks them with her strap-on until both butt-plugs come shooting out of their asses. They both get strap-on fucked in their asses deep and hard. After that, Kenzie gets huge gapes out of Jane's ass with a gigantic acrylic toy and Penny tongue-fucks her gaping hole. Jane fucks Penny with the slink while Kenzie masturbates in front of them with a vibrator. Finally, Kenzie gets five fingers inside Jane and five inside Penny and they both cum hard and lick their juices off of their Professor's hands.

Lily uses Pierce's big dick for her own please while squeezing and hurting his balls and shoving a sizable dildo up his ass.

I love seeing how far guys will go to please me, and I definitely have a sadistic side. I picked the biggest rubber cock I could find from the store to torment this gimp boy with, I am going to fuck his ass silly. Any time he protests I just stare at him with my big brown doe eyes and gorgeous doll face and he will literally do anything I want. I have a special way with getting whatever I want from men. I fuck his his ass while he moans and complains, but who cares? I am having fun! -Ariana Marie

Loser internet Troll Marcelo has irritated his mistress for the last time! The stunning busty brunette femdom goddess Chanel Preston will need to deliver severe punishment to this pathetic man loser. Tied up in restrictive rope bondage, Marcelo's face is gaged and covered. He is humiliated in sexy sheer women's stockings. His tiny cock pathetically hangs there as he is tormented with corporal punishment. The cane comes out and inflicts severe pain to Marcelo's saggy body. Clothespins are applied to his sensitive skin as he screams. He'll scream even louder when they are violently removed. Chanel delivers sharp pain to Marcelo's scrotum with the crop. This loser like's it! He is willing to do whatever it takes, whatever humiliations is needed, to please his mistress. Spread out on all fours and his ass in the air, Chanel Preston brings out a HUGE cock strap on. Marcelo's greedy man hole takes all of her packed heat deep in his ass. This anal whore will take a fucking for his goddess. Well if the strap on wasn't enough, Chanel Preston has more. Her fist! She punch fucks Marcelo's ass with her fist. He takes a deep anal fisting. All these screams is getting Chanel Preston hot. It's time for her to take true pleasure from this worm. A strap on cock is tightly positioned over Marcelo's face and he gets a front row view of his queen fucking his head. Tied up in tight rope bondage there is nothing he can do but pleasure his mistress to orgasm. After satisfying all her needs Chanel crushes her pathetic troll and stomps all over his body with her beautiful feet. Her black long stockings are gorgeous on her nude body. Finally extremely hot candle wax is poured all over this troll until he screams.

You get so jealous seeing my young, tight body dressed up in the sexiest lingerie wishing you could be me. Don't worry I want to help you become the cutest sissy slut you fantasize about being as I transform you into my whore. I am going to allow you to even be my dress-up dolly and wear this pink lingerie wrapped tightly around the curves on my body. Now rip those boy clothes off and throw them in the trash as you have no use for them anymore. I am going to turn you into my secret lesbian lover kept completely under my control and made to do the naughtiest of things a sissy only dreams about. Ohhh I see your cock loves the feeling of my panties gripped tightly around it as it begins to get extra hard for me. Now pull it to the side, grab it tightly and show me just how much you love being my sissy slut bent over ready to take any and everything I give you. Stroke for me sissy! -xxxo Mistress Emily Willis

Princess Mackenzie Moss only allows her slaves to cum when they are truly helpless without any control of their orgasms. Turning a boy into a frustrated mess as she edges and teases their bound cock's with vibrators brings great pleasure to Mackenzie. Cumming should never be easy on the slave as she loves to make him suffer before he gets the chance to relieve all that built up pressure. Princess Mackenzie jumps on the bound boy's face and rides his mouth making sure she gets her orgasm before he is allowed is a single one. The slave is finally allowed to blow his load by the grace of his Owners hand giving him one last orgasm before his cock gets locks right into chastity. Cocks are never allowed to be free in the house of Princess Mackenzie and she makes sure they never are.

Bobbi gets put on a stage and then is surrounded by three machines. She is instructed to pick a dick and start fucking. We follow her around her pedestal as she gets pounded and made to cum. Every orgasm makes her move to a different machine in search of the next orgasm. After she has given us everything she has, we move her into a standing position and fuck her until her knees get weak. The only thing left to do is to sit her down on a sybian and finish the job of blowing this girl's mind.

On all fours with their aching blue balls bound extra tight is exactly how Mistress Adriana likes her men. She knows just how badly he has been dying to cum and plays her favorite game of edging a helpless slave's sensitive cock. With enough pleading for mercy on his swollen purple balls, she gives him one last slippery stroke until he blasts a massive load. Adriana drains every single drop from his bound nuts to only scoop it right back up and hand feeds the sticky mess to her hungry slave.

The only way Mistress Valentina allows her slaves to cum is when they are torturously edged and crying for release. She gets great pleasure in watching her boys struggle in agony from complete sexual frustration while she cruelly edges out every last drop.

Kami Roberston is a bit of a chancer and takes an expensive taxi to get her home. The problem is she has no money but does not tell the driver. Once he finds out he is not best pleased. He gets into the back with her and pulls her over his knees. Then he removes her panties and spanks her bare bottom. Fortunately as you do, he found a wicked leather strap which he then used on her bare bottom and on her inner thighs.

Mistress Leigh Raven has her pet locked away in chastity. He is denied sexual pleasure, but that doesn't mean she can't have fun. Mistress straps on a dildo to her chastised slave, she orders he fuck her with the strap-on. The emasculated slaves thrusts the rubber cock into her wet pussy. He eagerly tries to please her as his cock throbs in its cage.

Submissive Hungarian brunette beauty Amirah Adara enjoys her first crowd BDSM session at the doctor's office where she's tied down in stirrups and fucked by the entire medical staff.

You are going to really learn to serve, and to please a woman. Get on your knees and worship my pussy, I want you to lick me until I cum. From my tight little ass hole to my clit licking back and forth giving me pleasure. Suck on my clit until I am dripping wet, make ME cum over and over. I want to use that mouth to masturbate myself because IT IS ALL ABOUT MY PLEASURE! Maybe if you learn to pleasure me properly I will let you cum next.

Mistress Mia takes strap-on to the next level and fucks her slave's hungry asshole like he has never been fucked before! He is literally just a hole to be fucked as Mia's big, purple cock splits his ass wide open turning him into a gaping whore and begging for more...