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Sissy Boys Naughty Bedroom Adventure

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Ms. Hannah has been one disobedient sub today and Mistress Michelle knows just how to make a good sissy out of her careless boyfriend. First off you need to get the little worm into some clothes more be-fitting a demure girly boy. After a quick look see in the closet our femdom goddess issues a wig, a nice dress and a pair of stockings and high heels and here you are – meet our girl Hannah. What’s more, a good sissy is an obedient sissy, so a collar with a leash and a crop will come in handy. Now sissy Hannah will obediently take any punishment and humiliation dished out by kinky Michelle even if it’s a toe or a strap-on shoved up the ass.
See more Sissy Boys and the FemDom Girls who Train Them exclusively from My Sissy Boyfriend.

Coffee and strap-on for breakfast


Sarah brings her cross-dressed lover breakfast and offers him to change his sexy yellow sleepwear for some smart outfit. She helps her sissy toy Stephanie into black suspender tights and takes out a pink strap-on dildo from the bedside-table. Sarah makes this unwilling sissy blow the fake cock like a good girl, then she orders him to fondle her nipples before she can start working his nicely lubed asshole.

Cross-dressed dudes are treated like filthy sluts forced to swallow and ride strap-on cocks of spoilt rich chicks!
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Sissy’s strap-on kitchen encounter


Whitney spotted her sissified boyfriend going about household chores in the kitchen. He looked really impressive in his blonde wig and elegant outfit with matching high heels. Being in playful mood Whitney approached Stephanie from behind and hiked up the sissy’s skirt for a hard strap-on surprise she hid in her jeans. The naughty girl pierced the guy’s bum right by the cupboard before nailing him on the table ready to be pleased in return.

Submissive males eagerly live female lifestyle and get fucked by their dominative girlfriends!
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Behaving sissy boy gets strap-on reward


Teonna knows what kind of treatment her sissified boyfriend needs. Armed with a strap-on she makes him worship and pleasure her before he can get even a taste of her extra equipment. Finally getting fully dressed sissy Veronica gives proper head and spreads ass cheeks for the full-on hardcore anal. The raunchy sissy takes it from behind and jumps on top thrusting his ass on this rigid fake cock.

Cross-dressed dudes are treated like filthy sluts forced to swallow and ride strap-on cocks of spoilt rich chicks!
Get it all with 100% exclusive and totally kinky x-rated pics and vids!

Fisted and strap-on sissy boyfriend


Gorgeous redhead Ellie finds a strap-on dildo on the shelf and can’t help testing it with her pussy. When a sissy guy comes in wearing a bright stripy dress and a red wig while eager for some strap-on treat, the girl makes him open up his ass first. She puts on gloves, applies some lube and starts fisting sissy Anna’s butt until it gets loose enough for her rubber dick. Then Ellie makes Anna swallow this strap-on cock and impale his bum on it.

Sissy guys clad in women’s wear blow and take up the brown the fake cocks of their kinky girls!
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One unforgettable experience


Selma is a spoilt rich girl and she can do whatever she pleases with her older acquaintance. Today she’s decided to turn him into sissy Kathleen, so she applies some make-up and dresses him into a long gown along with black lacy stockings and pumps. Then she takes out her black strap-on and fits it on while stripping to her undies. Now Selma is ready to give her sissy friend an oral-anal lesson that he won’t ever forget.

Sissy guys clad in women’s wear blow and take up the brown the fake cocks of their kinky girls!
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Dolled-up Sissy boy for the shoot


The right make-up and a nice wig can make a pretty girl even out of a plain looking guy. The right lighting and a sexy outfit can make wonders, so now feminized Lilly looks like a model ready to pose for her inventive photographer. Christine takes on cam every moment of the sissy’s transformation and humiliation, ordering him around and making him swallow her fake cock before pushing it up his once virgin butthole.

Feminized males switch roles with their strap-on armed girlfriends who don’t take no for an answer.
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Rich girl’s kinks revealed


Rich girls have lots of kinks, and gorgeous brunette Busy is no exception. However, you won’t guess that one of her kinks includes a big strap-on dildo and a sissy boyfriend. Busy isn’t willing to admit it at first, but Melissa is a master of negotiation, so soon this strap-on is put in place and Busy is ready to probe and poke Melissa’s hairy butt until it gets loose.

Sissy guys clad in women’s wear blow and take up the brown the fake cocks of their kinky girls!
Get in and enjoy thrilling plots and top-notch quality content!

Pajama party went wrong


Emily and Hilary were having a pajama party, and after a few glasses of wine and drinking Bruderschaft they got to deep mouth-to-mouth kisses and the party went out of control a bit. When blonde sissy Hilary changed his blue nighty for a red-n-black stripy dress, the things got even hotter. Emily took out her massive black strap-on toy and made Hilary beg for the feel of it while pleasuring her in every which way.

Submissive males eagerly live female lifestyle and get fucked by their dominative girlfriends!
Cum on in and see it on awesome hi-res pictures and videos!

Kept on a leash and treated like a femme


What makes a good sissy? Michelle knows how to make a good sissy out of her boyfriend. You need a wig, a nice dress and a pair of stockings and high heels and here you are – meet our girl Hannah. What’s more, a good sissy is an obedient sissy, so a collar with a leash and a crop will come in handy. Now sissy Hannah will obediently take any punishment and humiliation dished out by kinky Michelle even if it’s a toe or a strap-on shoved up the ass.

Sissy guys clad in women’s wear blow and take up the brown the fake cocks of their kinky girls!
Get in and enjoy thrilling plots and top-notch quality content!