Everyone dreads a bitch female boss, right? So when this businesswoman decides to turn her male secretary into a sissy and pulls out her strapon, it's time to cover your asshole and run for the elevator! Could you stand being the feminized assistant to this bitchy boss? Or would you rather spend your days sodomized and humiliated as her little sissy slut secretary?!!
sissy secretary picture

Her Sissy Slut Secretary

"Martha ran a thriving home-based business, and like any hard working businesswoman she needed a secretary so she hired Jim. But when he came to work he was shocked to find she had already laid out his clothes for him - all female clothing at that! Complete with lipstick and a wig! He was shocked to say the least, but he needed the money to support his wife and three kids, so he put them on and went about his secretarial duties. Martha was a strict boss, but fair, she paid well and never abused him or made any unsavory comments. Her only thing was her insistence that he dress as a pretty girl when in her office..."

Sissy Sexual Harassment!

"Then one day while he was filing some letters, Martha came up behind him and stuck her hand under his skirt and right into his panties! "You KNOW you want this, my little sissy secretary" she purred as she grasped his penis "You come in here everyday shaking your cute little ass in a short skirt and prancing about tying to turn me on! I think you should get this little penis hard for me!" Jim was shocked to feel a hard poking on his leg, he turned to see the strapon jutting from beneath Martha's skirt. "N-No, I-I-" he began to stammer but she cut him off "Shut up! I pay you to do what I say, now get this little cock hard NOW!" Martha roared "It's time you REALLY earned your pay!" But Jim couldn't get an erection under these circumstances, dressed as a sissy and with his female boss shrieking at him..."
sissy secretary picture
sissy secretary picture

Forced Sissy Suck!

"Martha was pissed that her sissy secretary Jim couldn't get an erection for her upon command, so she threw him to his knees and grasped her strapon. "Since you don't seem to be a REAL man, I think you can suck MY cock like a little girl then!" she hissed as she grabbed him by the hair and thrust the strapon into his mouth "That's it, suck it deep and hard like a good sissy would!" Jim tried to pull away but her grip was too strong. "Quit struggling, slut!" she yelled "You should be paying ME for the sissy suck training I'm giving you here today!" She thrust the rubber cock into his mouth time and time again. "Good boy" she cooed "If that was a REAL cock you'd be choking down my hot jizz load right about now!"..."

Virginal Sissy Asshole!

"Get up and bend over!" Martha hissed "Time to inspect that sissy asshole!" She practically yanked Jim to his feet and bent him over. She raised his skirt and spread his ass cheeks roughly with her fingers. "Yep! Just what I thought" she said "A virgin asshole. Well, I can take care of THAT for you. I'm going to make you into a REAL WOMAN!" Martha was out of control now, she reached for a jar of lube on her desk and smeared a cold daub into his clenching anus. Working two fingers in, she stretched and spread his stinging asshole. Jim groaned. "Stop it!" Martha sneered "A good sissy secretary willingly takes DICK-TATION! LOL!"..."
sissy secretary picture
sissy secretary picture

Sodomized By His Female Boss!

"She then pressed him down and savagely mounted him from behind with the hard strapon. "NOOOOOO!" he cried out in shame and pain, but she just started to thrust her pelvis violently against his bare ass again and again, driving the strapon deeper and deeper with each hammering blow. "Let me hear you moan, bitch!" Martha hissed "You better LOVE it, because you're going to get sissy FUCKED like this EVERY DAY from now on!"

Man Feminized And Sodomized By Strict Businesswoman Picture Gallery!

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