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.
And you thought girls demanded a lot of attention! This sissy boy is pestering his girlfriend for some sweet playtime. He even gets out her strapon dildo and starts to beg. The girl decides the only way to teach the cross dressing bitch is with a proper sissy training in his tight asshole. She lets the horny boy slobber all over the rubber cock and then slams him so hard that he shrieks like a tight virgin girl.
Sissy boy Elizabeth loves to get all dressed up like a girl and fucked in the ass. He makes sure that his mean girlfriend catches him in her closet and wearing her favorite silk teddy. Mary is pissed and gets ready for a real forced sissy fucking that will make her boyfriend’s asshole repent. She straps on her rubber cock and bangs the sissy’s tight manhole while he shrieks like a schoolgirl.
“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.
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