The 10 Best Sissy Videos on SweetFemdom

Molly and Alex at Home

28 minutes Jun 2019 Top 1

Molly Jane

Alex Adams

Molly is in the living room playing with a new rocking chair sex toy thing when her boyfriend, Alex, walks in. "You like this baby?" She's planning on fucking him later on it with a strap-on, then getting fucked by lots of other guys on it... The idea gets her so wet, she needs to cum, and that means Alex's tongue and mouth need to get to work. Molly orders Alex to strip …

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Last Fuck Before You’re a Sissy Eunuch w Lola Fae

24 minutes Apr 2020 Top 2

Lola Fae

Tony Orlando

Lola is at home smothering her slave's face with her crotch when she gets a call from her favorite stud. She was supposed to have some big dick come over and fuck her right, but he canceled. Lola decides to make do with her slave. "But if you fucking cum, I'm going to cut your balls off..." She makes her slave worship her pussy over her pantyhose and thong before she rips h…

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Kat Fucks Lance in Chastity Part 4

17 minutes May 2021 Top 3

Kat Dior

Lance Hart

Kat Dior can't get enough of pounding her chastity sissy's ass. Now she's wearing shiny tan pantyhose and a thong while she fucks him deep from behind. Her big perfect tits bounce with every thrust and she presses them on his back when he whimpers. She thinks he's earned a release. She unlocks his cock. But, he's not aloud to cum unless he has her giant black dick all the…

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Double Pegging Office Work

17 minutes Mar 2020 Top 4

Brittany Andrews

Whitney Wright

Tony Orlando

Whitney Wright is slacking at her office job with her feet on her desk. Her boss, Britney Andrews, confronts her about her pour performance, and tells her that her job is on the line unless she starts working hard and immediately fucks a guy in the ass with a strapon. Tony Orlando overhears what's going on so he walks into Whitney's office in just panties and lets them both k…

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Kat Fucks Lance in Chastity Part 1

17 minutes Apr 2021 Top 5

Kat Dior

Lance Hart

Kat Dior has Lance Hart locked in chastity. His blue balls are aching. She has him well trained at this point to crave a huge dick up his ass. She smiles when he begs her to fuck him deep, then she pounds his ass and makes him prostate cum like a sissy about 15 times. She leaves him dripping in his little cage. She'll be back for more.

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Get Used to My Strapon, Hubby Part 2

13 minutes Apr 2019 Top 6

Sarah Diavola

Lance Hart

Sarah Diavola just got home from an EDC Festival. She's wearing a bright leotard and shiny pantyhose and sneakers and looks hot AF. She's glowing and bragging about all the hot guys that fucked her in the ass. Her bitch hubby crawls into the room. He's wearing fishnets and has been waiting all night for her to come home and fuck his man pussy with her strap on, hoping she'l…

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Bunny Teases and Fucks Her Sissy Bitch

21 minutes Sep 2018 Top 7

Bunny Colby

River Enza

Bunny Colby has her sissy, River Enza, locked in chastity and dresses slutty for her. She toys with the idea of unlocking her sissy, but knows she never will. Bunny lets River worship her feet and her pussy, making her sissy clit rage against the chastity device and her balls ache. "What if I just chop off your sissy clit and balls...? Wouldn't that be easier? Don't you wa…

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Play with My Sissy Girlfriend

44 minutes Sep 2020 Top 8

Jade Indica

Sissy Fina

Lance is traveling and looks up a girl he had a crush on back in High School. He's passing through her town and is hoping for a hook up. He figured it was a long shot, but worth a try. She tells him she'll meet him at his hotel, bring a girlfriend and get kinky... Jade Indica walks into his room with a her sissy rubber maid slave on a leash and a strap-on swinging between he…

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Fabiana Puts Lance Under a Chastity Sissy Spell Part 3

13 minutes Jun 2021 Top 9

Lance Hart

Fabiana Fox

Fabiana has temporarily unlocked Lance's steel chastity cage to inspect the shrinking progress. After being very pleased, Evil Fabiana decided to step up the anal training and fuck him in the ass with a huge black strap on cock for 2 weeks straight until his mind and soul are putty. To be continued....

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Fabiana Puts Lance Under a Chastity Sissy Spell Part 2

13 minutes Jun 2021 Top 10

Lance Hart

Fabiana Fox

Evil Fabiana has now completely enslaved Lance Hart. Even without wearing the magic crystal collar, his brain and soul have been converted into a cock craving chastity sissy who believes his dick is worthless. The longer he is under the spell, the smaller his dick gets. Fabiana straddles Lance to toy with his steel cage and humiliate him, revealing the master plan of enslavi…

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