Sissy goes for a wild strap-on ride

Sometimes it’s sexy female clothes and something hard shoved up the ass that these sissy males secretly dream of. Just the feel and look of lacy, nylon and silky fabric can make them horny, and Melissa is the one who knows it very well. This sissy guy gobbles on the strap-on protruding from under Myra’s see-thru nighty and gets on top of it to ride the rubber cock with his lubed butt.
Male fucked like a female

When Teonna is in the freaky mood, her lover turns into a girl. Now with a make-up and clad in a short pink skirt, a sexy blouse and black stockings he is Veronica who loves to give head and take it up the ass. After a mouth-splitting blowjob Teonna bottle fucks Veronica’s behind before pushing her extra equipment into this loosened cornhole. Still the sissy does like it thrusting his bum onto the rigid fake cock.
Drunk sissy fucked as a femme

Emily and Hilary have a drink and go for some role play. Sissified Hilary changes his nighty for a stripy dress while the teen girl takes out her fake cock and soon wears nothing but a strap-on. Emily makes her sissy drunk and ready to show his cock-sucking skills. Then Hilary changes into a new outfit getting ready for a steamy anal fuck-fest. This naughty teen plunders the sissified guy’s rectum giving him an ass-fuck of his lifetime.
Bathroom fornication with a freaky sissy

Sissified Melissa is ready to worship and please pretty Myra who’s armed with a huge protruding strap-on. This sex toy is meant for the sissy’s throat, and the girl gives it to him sitting right onto his face. They do it on the floor in the bathroom, and Melissa tries to swallow the dildo deep down his mouth, so it will slide smoothly into his bung hole too.
Spoilt girl bangs a submissive sissy

A rich girl can have everything she wants, even a submissive sissy guy if she feels like having one. Clad in one of Beau’s evening dresses with matching stockings and a blonde wig Joan looks like a perfect strap-on whore. Well, he looks like one and he behaves like one blowing this sizeable fake dick and taking it up his lubed butt hole while riding on top.
Sissy Boys Naughty Bedroom Adventure

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.
Curious sissy maid tied up and fucked

Maids are usually too curious and they love trying luxury clothes that belong to their mistresses. This sissy maid couldn’t resist the temptation too, so Kelly got caught by Miss Valerie wearing her baby-doll. Such behavior couldn’t be tolerated, so Valerie demanded satisfaction and she had some dildo gender bender play on her mind. The girl tied up the sissy’s hands and had her way with him plunging her rubber cock into his mouth and butt.
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.
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.
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.

