Category Archives: Kendra James

Miss Kendra Punishes You with Her Pink Strap-On Cock

When Miss Kendra gets a call from her friend Rhianna that you were seen back snooping in a ladies’ lingerie shop, Miss Kendra takes swift, severe action to punish and humiliate you. We’ll see how fascinated you are with all things pink and girlie when Miss Kendra gets through with you. Spread your legs for Mistress, naughty sissy.

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Cuckold Condom Cleanup Session for Miss Kendra’s Bullcock Boyfriend

Miss Kendra’s massively-endowed boyfriend knows all about you – that you’re a panty-wearing sissy cuckold. He thinks you’re a laughable little joke. He left you a pile of hot gooey presents from his last sex session with Kendra. And now Miss Kendra is going to use his cum-flooded condoms to put you in your place and humiliate you.

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Miss Kendra Strips Your Manhood and Snaps You into Sissy Panties

Strip off your ridiculous real man costume! Miss Kendra has found a real man to take your place. You’re staying home – in sissy panties. Slide the emasculating panties up your legs – as Miss Kendra belittles you. Then get down on your knees and show your glamorous goddess who owns you. Beg to piddle the worship goo into your panties like an obedient sissy!

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Miss Kendra Torments Your Caged Cock into a State Beyond Suffering

As you can see from the look of pure delight on her face, Miss Kendra loves to see you suffer. Kendra asked to do a session with you after you’d spent a week in your chastity cage, so that she could taunt, tickle, and torture you into a state beyond suffering. After this session with Miss Kendra, you will be nothing but a babbling, begging, pleading puddle of precum.

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Miss Kendra Catches You Sniffing and Stroking Her Sexy Stockings

Aha! What a pathetic little worm you are. You know that Miss Kendra regards you as nothing but a simpering sexless sissy, so you steal her stockings to sniff and fondle. Well now you’ve gotten caught by Miss Kendra – wearing sexy white seamed fishnets – just as you’re about to soil her silky nylons with your sissy slime. Prepare to be emasculated, wussy.

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Miss Kendra Permits You to Cuckyfuck Your Humpypillow

You were an obedient little sissy cuck all week long for Miss Kendra. So now it’s time for your reward! Miss Kendra kicks your humpypillow out from the closet so you can give it a good cuckyhump while she towers over you and ridicules you. Kiss Miss Kendra’s polished toes and sissy-squirt your pillow. Hurry up, humpycucky, her boyfriend will be over any minute!

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Sorority Slave: Miss Kendra Assesses Your Toilet Scrubbing Skills

You know your punishment prospects can’t be good when Miss Kendra comes to inspect your toilet scrubbing task while wearing a strap-on cock. Get down on your hands and knees, sorority slave. Stick your face in the girls’ toilet and raise your sassy sissy ass in the air so Miss Kendra can teach you what happens when you disobey your mistress.

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Miss Kendra: Black Glove Sissy Cummy Humiliation Session

You already know that when Miss Kendra pulls on her shiny black gloves that you’re going to be humiliated. Maybe you’ll have your face slapped. Maybe you’ll be violated and shamed like the naughty sissy you are. Maybe Miss Kendra will make you spit out the worship goo in the most humiliating way you can imagine.

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Cucky Cummie Carpet-Humping Under Miss Kendra’s Bed

Kendra is bringing over one of her studs for a blistering night of sex – and you get to experience it from beneath Kendra’s bed. When Kendra strips each overflowing condom off her lover’s cock, she’s going to toss them to you, like table scraps to a puppy. You can slide the cum-filled XL over your XS winkie, make pretend and hump the carpet as your mistress gets her pussy pounded up above you.

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Spit Out the Sissy Boot Polish for Miss Kendra

Imbecile! Miss Kendra left you one task: to give her dominatrix boots a thorough cleaning. You couldn’t even do THAT right. She’d kick you in the balls if you had any. Instead, you’re going to clean her boots with your tongue, and then wax them – by reaching inside your sissy panties and squeezing out every last drop of your wussy boot polish for mistress.

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