Mary is a real office bitch that has her male coworkers terrified. When a skinny new boy starts work, the girl is eager to break him in with a forced fem sissification. The boy doesn’t know how to respond when Mary tells him to put on a dress and blonde wig. He gets one look at her big strap on dildo and knows that bitch is serious. Even though his ass regrets it, this sissy boy can’t resist being fucked like a girl.
Before Beau can get the job at this fashion agency, he has to prove he knows how to relate to the girls. His final test is a forced sissy makeover and nasty anal fucking. His sexy boss does the honors of applying his purple eye shadow and fixing his pretty hair. Beau looks scared when he sees the big rubber cock but has no choice against the dominant babe. Since the office boy is already feeling like a bitch, he really gets fucked like one too!
Whitney always gets what she wants. Today, the spoiled girl wants to play with a sweet blonde schoolgirl. She tells her boyfriend to come over and makes him dress up for sissy training. The boyfriend becomes Stephanie and even starts to act like an innocent babe. He shrieks when he feels the oil dripping down his ass crack and then gives a girly scream while a strap on slams his tight hole.
“Valerie” has always had a passion for wearing panties and sexy outfits. The naughty cross dressing maid can’t help but admire the luxury clothes in his mistress’s closet. When she goes out, the boy gets himself all dolled up and struts around feeling sexy. The mistress walks in on the prancing boy and decides to give him a real sissy training. She ties him up and gets her strap on cock for a hard rear pounding.
A good assistant is hard to find, especially for top fashion photographers. When Christine is short a model for her shoot, she calls over her bitch and decides he will be perfect to model the outfit. She gets him all dressed up like a pretty sissy boy. As lovely as the assistant looks, he still isn’t getting the poses right. Christine decides that the only way for this sissy to learn is a forced fucking in his tight manhole.
When sissy boy “Kathleen” gets caught playing in his girlfriend’s closet, Selma is pissed. Kathleen clearly lacks the style sense it takes to really get gorgeous and glamorous. The only way to teach the cross dressing boy is to let him feel like a girl in all ways. Selma gets out her strap on dildo for a real forced sissy fucking that will teach this guy who it feels to be pumped like a bitch.
Emily is convinced that she can fuck better than her boyfriend. To prove her point, the bitchy girlfriend calls over her stylist for a forced sissy makeover. The skinny lad is transformed into a glamorous party girl slut in a shiny outfit. He obediently helps his girlfriend adjust the strap on dildo and sucks the rubber cock to make it all slippery. This sissification gets really kinky when the boy sits right on the beast and slams his man-gina.
Dennis gets turned into Denise in this forced fem sissy training. The boy’s sexy girlfriend decides that he is too much of a bitch to use his cock on her. Instead, the kinky babe decides to play cruel games with the tiny man pole. She tortures his dick with clamps but the real torture is the humiliating sissification that comes next. The mistress puts her boy toy in a slinky dress and stockings and tells him how beautiful he looks as a girl.
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