Category Archives: sissy training

Miss Kendra Cuckolds You in Her Closet and Commands You to …?

After you spend the night in her closet, tending to her shoes and lingerie while she beds her boyfriend, Miss Kendra allows you to collect your reject’s reward: one of her boytoy’s loaded condoms! Miss Kendra makes you tug the XL rubber over your tiny nubber. Will she command you to spurt your spoogie into his massive manload after she finishes laffing at your peepster?

000592_11kencloset_still_enlarged_0007_layer1 000592_11kencloset_still_enlarged_0006_layer2 000592_11kencloset_still_enlarged_0005_layer3 000592_11kencloset_still_enlarged_0004_layer4 000592_11kencloset_still_enlarged_0003_layer5 000592_11kencloset_still_enlarged_0002_layer6 000592_11kencloset_still_enlarged_0001_layer7 000592_11kencloset_still_enlarged_0000_layer8

humiliatrix.com/join

 

Princess Cee Cee Tranforms You into Her Emasculated Sissy Maid

Glamour girl Cee Cee has noticed you nervously snooping around her high fashion custom lingerie shop. Cee Cee knows you’re shopping for yourself, Miss Fumble Fingers. Now Cee Cee has decided to turn you into her personal sissy maid. If you can’t meet Cee Cee’s impossibly high standard of feminine perfection, you will be humiliated in front of her fashionista girlfriends.

000593_ceecee01_still_enlarged_0007_layer1 000593_ceecee01_still_enlarged_0006_layer2 000593_ceecee01_still_enlarged_0005_layer3 000593_ceecee01_still_enlarged_0004_layer4 000593_ceecee01_still_enlarged_0003_layer5 000593_ceecee01_still_enlarged_0002_layer6 000593_ceecee01_still_enlarged_0001_layer7 000593_ceecee01_still_enlarged_0000_layer8

humiliatrix.com/join

Bedroom Shame Session: Inadequacy Drills with Princess Selena

Because you lack the tools and ability to do the job like a real man, Princess Selena is going to put you through an intensely humiliating bedroom shame session. Selena is going to make you violate yourself with a sissy vibrator, as she stares you in the eye and taunts you unmercifully, refusing to let you stop until your pitiful little sissy nipple squirts and spasms. Bzzzz… LOL!

000600_41selvibe_still_enlarged_0006_layer1 000600_41selvibe_still_enlarged_0005_layer2 000600_41selvibe_still_enlarged_0004_layer3 000600_41selvibe_still_enlarged_0003_layer4 000600_41selvibe_still_enlarged_0002_layer5 000600_41selvibe_still_enlarged_0001_layer6 000600_41selvibe_still_enlarged_0000_layer7

humiliatrix.com/join

Princess Isobel Takes Your ‘Sissy Temperature’ with Her Pink Probe

Pulling your pants down for the nurse has never been more humiliating than when Isobel pins you down to take your ‘sissy temperature’ with her pink probe. Isobel is going to find out the hard way whether you’re a man – or a sputtering sissy who makes piddle-puddles while getting penetrated.

000606_80isotest_still_enlarged_0005_layer1 000606_80isotest_still_enlarged_0004_layer2 000606_80isotest_still_enlarged_0003_layer3 000606_80isotest_still_enlarged_0002_layer4 000606_80isotest_still_enlarged_0001_layer5 000606_80isotest_still_enlarged_0000_layer6

humiliatrix.com/join

Caught, Chastised & Caged: Goddess Rhianna Locks You into Chastity

You. Pathetic. Dreamer. When Goddess Rhianna discovers you’ve soiled her panties with a feeble expression of your unrequited lust, Rhianna’s resolve is swift and severe. An emasculating dressing down leads to the ‘strip and present’ command. You are about to be shamefully exposed and mercilessly punished by a key-dangling ice princess whose beauty is matched only by the depths of her cruelty.

000609_44rhiachas_still_enlarged_0006_layer1 000609_44rhiachas_still_enlarged_0005_layer2 000609_44rhiachas_still_enlarged_0004_layer3 000609_44rhiachas_still_enlarged_0003_layer4 000609_44rhiachas_still_enlarged_0002_layer5 000609_44rhiachas_still_enlarged_0001_layer6 000609_44rhiachas_still_enlarged_0000_layer7

humiliatrix.com/join

Poker Night Emasculation: You Are Miss Kendra’s Sissy Servant

Miss Kendra has arranged a night of poker for her dominant girlfriends. Guess who’s going to light their cigars and buff their spike heels? You are, sweet cheeks, in a frilly lace sissy maid uniform. The guest list includes your ex-girlfriend and one of your female co-workers. Any lapses in sissy decorum will result in an attitude adjustment session – with your panties pulled down in front of the ladies.

000610_53kenpoke_still_enlarged_0008_layer1 000610_53kenpoke_still_enlarged_0007_layer2 000610_53kenpoke_still_enlarged_0006_layer3 000610_53kenpoke_still_enlarged_0005_layer4 000610_53kenpoke_still_enlarged_0004_layer5 000610_53kenpoke_still_enlarged_0003_layer6 000610_53kenpoke_still_enlarged_0002_layer7 000610_53kenpoke_still_enlarged_0001_layer8 000610_53kenpoke_still_enlarged_0000_layer9

humiliatrix.com/join

Swallow Like a Slut: Your Cocksucking Lesson with Princess Isobel

You feeble fuckwit. Since you can’t do it like a man, Isobel is going to tart you up and teach you to take it down your throat like a cum-craving slut, as the back-up BJ bitch to her blueballed sugardaddies and studbull boytoys. You will learn to suck and swallow like a submissive slut – or get your face slapped raw by your cock mistress, Princess Isobel. Double session!

000620_85isosuck_still_enlarged_0010_layer1 000620_85isosuck_still_enlarged_0009_layer2 000620_85isosuck_still_enlarged_0008_layer3 000620_85isosuck_still_enlarged_0007_layer4 000620_85isosuck_still_enlarged_0006_layer5 000620_85isosuck_still_enlarged_0005_layer6 000620_85isosuck_still_enlarged_0004_layer7 000620_85isosuck_still_enlarged_0003_layer8 000620_85isosuck_still_enlarged_0002_layer9 000620_85isosuck_still_enlarged_0001_layer10 000620_85isosuck_still_enlarged_0000_layer11

humiliatrix.com/join

Office Intern Aly Blackmails You Into Panty Slavery

When does your 19-year-old intern become your boss? When she finds the career-threatening stash of submissive sissy porn you keep hidden on your work computer. OMG! Now snarky Aly knows all your embarrassing secrets. Will she use them to enslave you – or destroy you? All you can do is whimper for mercy as you obey every one of Aly’s humiliating commands.

000621_35alyoffice1_still_enlarged_0004_layer1 000621_35alyoffice1_still_enlarged_0003_layer2 000621_35alyoffice1_still_enlarged_0002_layer3 000621_35alyoffice1_still_enlarged_0001_layer4 000621_35alyoffice1_still_enlarged_0000_layer5

humiliatrix.com/join

Miss Kendra Gives You A Brutal Punishment Fucking

When she finds out from her friend Rhianna that you were caught fondling the panties at Rhianna’s lingerie boutique, Miss Kendra offers to punish you herself: the kind of emasculating punishment fit for a simpering sissy with a secret fascination for all things feminine. Pull your panties down for Kendra, missy. You’re about to learn what it’s really like to ‘be the girl.’

000623_27kenfuck_still_enlarged_0004_layer1 000623_27kenfuck_still_enlarged_0003_layer2 000623_27kenfuck_still_enlarged_0002_layer3 000623_27kenfuck_still_enlarged_0001_layer4 000623_27kenfuck_still_enlarged_0000_layer5

humiliatrix.com/join

Miss Kendra Makes You Swallow Your Pride, His Cumload

Miss Kendra knows you’re jealous of her stud boyfriend. He thinks you’re a pathetic sissy joke! To prove it to you, Miss Kendra is going to teach you to fluff his cock and unfurl an XL condom over his manhood. After he pleasures Miss Kendra, you can meekly ask permission to remove his condom and dispose of his hot steamy real-man residue like a good sissy cuckold.

000628_25kendrink_still_enlarged_0004_layer1 000628_25kendrink_still_enlarged_0003_layer2 000628_25kendrink_still_enlarged_0002_layer3 000628_25kendrink_still_enlarged_0001_layer4 000628_25kendrink_still_enlarged_0000_layer5

humiliatrix.com/join