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Hot photo session with a sissy model


Christine is known to be a talented photographer with somewhat twisted imagination. Today she needs a sissy model for her new photo session. Dressed in an all-female outfit Lilly makes for a perfect model. He poses for her cam flashing his cute thong, sexy black fishnets and finally his rigid hard-on. Then Christine wants to make a few hot shorts with a strap-on, so Lilly kneels down to suck on it and takes it up the ass in every which way.

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!

Sissy guy begs for strap-on assault


Crossdressed Melissa hikes up a dress showing off black stockings and a thong trying to prove that he’s not a guy, but a girl now. Then this sissy takes out a strap-on dildo and asks a girl for assistance. First unwilling Busy soon gets curious enough to try it on admiring her extra equipment. The sissified guy wets the rubber cock in his mouth before spreading his cheeks for some nice butt plowing, and it looks like Busy begins to enjoy it too.

Dolled-up sissy guys get overpowered and pummeled by extra-equipped divas. Pervy role play, sore throats and butts!
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Collared sissy used like a fuck toy


Dennis changes his outfit for a short stripy dress and black stockings that along with a tiny thong give full access to his rear. His new attire is spiced up with a collar and cuffs, so you’ll know who’s gonna get fucked. Chris is armed with a sizeable strap-on and she aims it for the sissy’s butt. The girl forces her fake cock really deep into the sissified guy’s asshole making him whimper like a slut.

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!

Sissy’s secret uncovered


Finding a strap-on dildo on the shelf in her guy’s closet, Ellie can’t resist trying it, so she shoves the toy right into her itchy pussy. However, she gets watched by her crossdressed boyfriend willing to join her. Ellie bends down feminized Anna using rubber gloves and some lube to fist the sissy’s ready ass. Then she puts on this big pink strap-on and thrusts it into the sissy guy’s throat and well lubed butthole.

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!

Sissified coed takes up the ass


Spoilt teen Whitney brings a cute blonde wig for her sissy boyfriend, adds a short tartan skirt and white knee-highs, and he turns into raunchy coed Stephanie. However, that’s not everything she’s got for him, a long and hard surprise is hidden under her tiny skirt and it’s reserved for the sissy’s ass. Whitney pushes a big strap-on dildo into Stephanie’s butt from behind, letting him suck on it and ride it before she’s done with him.

Feminized males switch roles with their strap-on armed girlfriends who don’t take no for an answer.
Cum and let these sissy guys bring to life your most daring dreams!

Sarah And Her Cross Dressed Lover Boy

cross dressed lover boy
With an amazing set of tits like that it’s no wonder why this hot femdom babe has her sissified boyfriend on all fours barking like a dog! Watch what happens when she decides to have an afternoon of fun and humiliation with her favorite cross dressed boy toy!
Click here to watch the exclusive videos from My Sissy Boyfriend!

Sissy and his girl share one dildo toy


Michelle was spending a romantic evening with her sissified boyfriend who did look like a girl in his blonde wig, stripy dress, suntan stockings and black pumps. On having some wine both of them were ready to go even further. Sissy Joan took out his handy double headed dildo showing his glamour teen lover what he liked to do with it, and soon they were sucking and fucking it together.

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!

Sissy begs for strap-on abuse


You won’t have to show this sissy who wears the pants, as he obviously prefers skirts, stockings and blouses. Now we should call him Stephanie and see him trying to talk his cute teen girlfriend Sarah into giving him strap-on fuck. He helps her fit this equipment and then goes down on her fake cock. Sarah really becomes involved and now it’s time to lube Stephanie’s ass and break right in.

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!

Crossdressing bedroom affair


This guy enjoys role playing, so once he stays home alone, he uses make-up and wears female sleepwear turning into his other self. So meet Elisabeth, Mary’s sissy boyfriend and see what they’re doing in the bedroom. Mary finds her guy crossdressed again, so she slips into her strap-on harness and gives this sissy the treatment he well deserves. She fills his mouth and drills his tight ass until he screams like a girl.

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!

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.

Dolled-up sissy guys get overpowered and pummeled by extra-equipped divas. Pervy role play, sore throats and butts!
Make one click and you’ll be brought to the alternative world of your fantasies!