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MY SISSY BOYFRIEND
mysissyboyfriend

Welcome to the alternative reality. We know that you secretly dream about switching roles with your girlfriend, still you've never dared to. Have you ever delved in your girl's wardrobe? Have you ever wanted to try those sexy female clothes and provoking underwear? Wouldn't you like to know what it feels like to be a girl? Wouldn't you like to try and do all those things that real girls have to do? Have you ever fantasized about being fucked by your strap-on armed girlfriend, while dressed up as a sissy and treated as a whore? You know your girl is probably willing to switch the roles too! We aren't oracles, but we know your most intimate dreams. Are you still in doubt?



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mysissyboyfriend
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.


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Red-haired Ellie was in for a bit of a surprise. As she was drinking her champagne blindfolded with a sleeping mask, her sissified lover Anna brings in his beloved strap-on dildo begging Ellie to try it on. Once the girl has it on, Anna starts munching this fake cock before bending down to take it from behind. Ellie applies some lube and proceeds giving her pervy sissy boyfriend the anal pounding of his lifetime.


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mysissyboyfriend
Sarah wakes up her boyfriend bringing him breakfast and a curly blonde wig for some naughty play. She helps him into a womanly outfit with a tiny thong and white stockings and then makes him suck on her strap-on cock. First unwilling sissified Stephanie starts blowing it like a good girl before Sarah parts the sissy's ass cheeks and drives her tool into his rectum pumping it in every which way.


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mysissyboyfriend
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.


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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.


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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.


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mysissyboyfriend
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.


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mysissyboyfriend
Luscious Mary treats her co-worker like her sissy boy toy making him dress up in all-female clothes with a fair-haired wig and suntan stockings. They're freaking out right behind the closed doors in their office. Mary strips off and attaches her special abuse tool - her king-size strap-on, that is. It slides smoothly past sissy Elisabeth's red painted lips and then pierces his once very tight butt hole.


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mysissyboyfriend
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.


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mysissyboyfriend
This guy has prepared a special surprise for Valerie. He asks her to close her eyes and goes to the bathroom to change into his female outfit with a sexy corset and red stockings. At first Valerie is really shocked with Kelly's sissy looks and can't see the point of this crossdressing. But when a red dildo and a big strap-on are taken out and put to use, the things get really hot, and the girl feels involved too.


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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.


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mysissyboyfriend
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.


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mysissyboyfriend
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.


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mysissyboyfriend
It was New Year's Eve when Christine found her boyfriend Lilly dressed somewhat unusual in a woman's outfit. She also found a strange present under the New Year's Tree - a huge black strap-on. Surprised she still decided to use it and woke up her sleepy sissy guy. Christine lubed Lilly's back hole and pushed her big toy all the way in. She also made her sissy wear a wig for better resemblance to a naughty girl and gave him ass-to-mouth.


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mysissyboyfriend
When this guy was applying for a job, he could hardly imagine that it was his sissy skills that would be put to test. Blonde Beau helped him with his make-up and wig, before sending him to the bathroom to make him clean and ready for a strap-on workout. She dressed the sissy into a pretty blouse and a skirt with classy black stockings to match. Then Beau checked how deep Joan could take it into the mouth before spreading his ass cheeks.


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mysissyboyfriend
Gloria saw a strange dream. She was clad in a hot military-like outfit while helping her sissy boyfriend Hannah to turn into a girl. He was wearing a pair of sheer stockings and a long-haired wig, and she brought him a lace trimmed nighty and some matching lacy thong. She held a crop in her arms, and her big black strap-on dildo looked very threatening, while she was plunging a butt plug into Hannah's rear before putting to use her fake cock too.


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mysissyboyfriend
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.


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mysissyboyfriend
Dark-haired Gloria was surprised to see her boyfriend dressed like a girl, but soon he showed her what he was after. It wasn't some girlish talk, but hard strap-on fucking that this sissy had on his mind. So he made his best to lure the girl into giving it to him. Hannah displayed his great skills at giving blowjob and then spread his stockinged legs to lube his tight round-pussy for some proper banging that the girl was about to dish him.


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mysissyboyfriend
Dressed as a secretary, sissy Kathleen brings in some papers and gets a special strap-on assignment. Selma paints his lips with bright red lipstick and makes him suck on a rubber dick. The nasty sissy does his best smearing lipstick all over the rigid toy and his face. Then the girl pierces his ass from behind and makes the sissy guy spread wide his stockinged legs for the fierce anal workout.


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mysissyboyfriend
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.


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mysissyboyfriend
Kathleen should know better than using Selma's make-up things and trying on her sleepwear. When the girl finds out, she gets really pissed off, but then she thinks of the best way to punish this crossdresser. Selma takes out her beloved pink strap-on and makes this sissy put his mouth to work. Seeing as Kathleen is doing it so well, the girl gets aroused too, so she puts on that strap-on dick and plows her feminized lover's mouth and behind.


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mysissyboyfriend
Being curious what it feels like for a girl, this sissy guy applies some make-up, wears a blonde wig and puts on female undies. His bitchy teen girlfriend Michelle provides him with fine black stockings and some luxury clothes from her wardrobe before making him work them off with his mouth and butt. Sissy Joan is munching on the strap-on rod and readily parts his ass cheeks for some proper butt drilling taking up every inch of the sizeable toy.


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mysissyboyfriend
Emily is a rich girl with utterly perverted mind. Today she's decided to play and make a twin girl from her guy. She invites her own make-up artist, lends him her blonde wig and one of her dresses along with stockings and high heels. Then she asks her sissy Hilary to close his eyes for a strap-on surprise. Emily makes this sissy kneel down and gobble on her enormous black dildo before she plunges it into his back hole.


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mysissyboyfriend
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.


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mysissyboyfriend
Stephanie is a sissified maid and this pervy guy looks really good in this white-n-black uniform with a little red apron. As Whitney comes into the kitchen and sees the sissy going about his household chores she gets hot and starts groping Stephanie. She ties his hand behind his back with the apron spreading the sissy on the table and plugging his butt before letting him taste the dildo that's been in his ass.


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mysissyboyfriend
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.


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mysissyboyfriend
White stockings, high heels, a bit of make-up and a sexy wig turn this guy into feminized Melissa who badly needs to have something hard in the ass. To make him look even more feminine his girl brings him some lingerie, a skirt and a blouse. Once he puts them on, the game begins. The sissy guy and his girl change roles as Busy reveals her huge black strap-on toy and shoves it first into Melissa's mouth and then up the bum.


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mysissyboyfriend
While acting a girl in his blonde wig Dennis gets ordered to strip naked in front of his strict female mistress Chris. She's playing a bit with his cock and balls using clothes-pegs and a crop before making her sissy boyfriend wear a sexy female outfit with stockings and high heeled sandals. She spanks his ass and pushes her finger into his brown hole making it ready for a hard strap-on session he well deserves.


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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.


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mysissyboyfriend
When this kinky sissy guy is in a need of a really good fuck, he puts on one of his cute gowns, a blonde wig, high heels and plays girly. Now he's Hannah, a very submissive and obedient sissy, ready to fulfill any kink of rich and spoilt dark-haired Michelle. Hannah is getting kept on a leash and humiliated in every way possible before raw strap-on drilling of his eager throat and tight man-pussy.


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