14 Results Found:


05.10.2024
Description: When a sissy loser like Donald sees a rock hard strap on dildo there's nothing he'd rather have is one stuffed up his tight sissy anus and slut Irene is happy to oblige him. The nasty dom bitch hops right onto that tight hot sissy butt of his and the sissy fool starts sucking her strap on cock and after being humiliated enough he then gets that rock hard strap on dildo stuffed up him royally. She then begins slamming that sissy's bunghole and wears his dumb ass out.

Model(s): Irene B, Donald A | Duration: 14min 37sec | Type: SD | Size: 213mb

Model(s): Irene B, Donald A | Site: StraponSissies.com | Category: Videos


24.08.2024
Description: After their last session where Rita tore that ladyboy ass wide open of Donald's the fool came back to take on her hard sturdy strap on again. Irene's strapon was more than a match for his ripping sissy asshole and she gave him a thorough pounding that sissyboy's butthole until all he had left was a anihilated sissy butt. It's a good thing their significant others gone for the day as she turned on to the max with the idea that she could use her rock hard strap on dildo again to humiliate his nasty sweet asshole and he even thanked her after she fucked that ass of his.

Model(s): Rita, Donald | Duration: 12min 46sec | Type: HD | Size: 277mb

Model(s): Rita, Donald | Site: StraponSissies.com | Category: Videos


05.08.2023
Description: Once a horny cruel dominatrix like Helga gets a brand new rigid strapon dildo she means to break it in by busting open a sissy boy's big meaty asshole and poor Donald is going to be her newest victim. She'll make the sissy boy do some nasty sucking ass entombed strapon cock after they're sexing things up for the ultimate humiliation. Soon she is firing up that steel hard strapon and gets to pounding that sissyboy's butthole like a piston, totally destroying his gooey funky butthole.

Model(s): Helga, Donald A | Duration: 16min 39sec | Type: SD | Size: 242mb

Model(s): Helga, Donald A | Site: StraponSissies.com | Category: Videos


19.07.2023
Description: Donald was getting ready for his tight sissy boy butt to get fucked crazy by Helga and soon as they got that libido up She zeroed in on his tight hot sissy butt. The poor fool took that rock hard strap on dildo so deep into his nasty hot ass that his howling scared the neighbors. She then banged that butt like a madwoman and soon she left him with nothing much left except a destroyed whiney boy ass.

Model(s): Helga, Donald A | Number of pics: 76 | Resolution: 1505x1000

Model(s): Helga, Donald A | Site: StraponSissies.com | Category: Pictures


10.08.2022
Description: Giant tranny Donald can't put that huge monster strapon down and he begs Trudy to bust his tight nasty ass open with it. The horny naughty couple get really horny after his begging and now it's time for the whiney little sissy ruthless hardcore fucking that will probably break that raw study strap-on in half. The action gets hotter as she plunges that huge monster strapon into his whiney little sissy tight nasty ass with a fury that frightens them both.

Model(s): Trudy A, Donald A | Duration: 12min 29sec | Type: SD | Size: 181mb

Model(s): Trudy A, Donald A | Site: StraponSissies.com | Category: Videos


16.07.2022
Description: Irene gets hold a of Donald again and being the ultimate nasty bitch slut she is that means Donald is in for some serious trouble as Irene is going to use her rigid strapon dildo and tear him a new one with it. She makes him do some sissy ass sucking ass entombed strapon cock after she plunders his backside and poor Donald knows he will not be the one getting a merciful lesson from Irene. Irene just wears out that thick meaty strapon on this foolhardy lad as she continues pounding that sissyboy's butthole like he stole all the cookies from the jar.

Model(s): Irene B, Donald A | Number of pics: 54 | Resolution: 1505x1000

Model(s): Irene B, Donald A | Site: StraponSissies.com | Category: Pictures


05.01.2022
Description: Donald is a big whiney little sissy and that means big as in tall and loves a good huge monster strapon ruthless hardcore fucking. Along comes cruel sneaky dom Helga who knows what he wants and the horny naughty couple become sexually aroused and go berserk. The whiney little sissy takes that hard ripping strapon all the way up his snug little butt and the steam rises. Just wait until Helga pours on the action and the whiney little sissy brutal nasty screwing has Donald begging for mercy.

Model(s): Helga, Donald A | Duration: 14min 30sec | Type: SD | Size: 211mb

Model(s): Helga, Donald A | Site: StraponSissies.com | Category: Videos


18.09.2021
Description: Sissy boy Donald gets to showing off his ripping sissy asshole and Helga takes him on and will leave him a cowering butt sissy slave when she gets done with him. She's got her rock hard strap on dildo and tools and she's going to go to work on his tight hot sissy butt leaving him with nothing left but a anihilated sissy butt. To add to the humiliation she'll have him do some ass to mouth just to prove who's boss around here. Dude is sorry he challenged her hard sturdy strap on as it has totally destroyed his tight hot sissy butt.

Model(s): Helga, Donald A | Number of pics: 80 | Resolution: 1505x1000

Model(s): Helga, Donald A | Site: StraponSissies.com | Category: Pictures


19.05.2021
Description: Horny Irene needed to break in her steel hard strapon and now that she had sissy Donald in her power, his big meaty asshole was good a target as any. He submitted to her power and soon she was deep into his tight hot sissy butt giving it a thorough workout. As they fucked they both got real horny and the furious session went into overdrive. Her rock hard dildo sure got broken in as she literally destroyed his nasty hot ass and they both came like crazy.

Model(s): Irene B, Donald A | Number of pics: 62 | Resolution: 1505x1000

Model(s): Irene B, Donald A | Site: StraponSissies.com | Category: Pictures


17.04.2021
Description: Sissy Donald underestimated nasty dom bitch Irene and the power of her rigid strapon dildo! Redhead Rita is quite the expert at dispensing justice with her massive strap on and to prove his unworthiness, he is tested by giving her a strapon blowjob beginning his journey into total humiliation at that business end of a steel hard strapon. she dives into that nasty sweet asshole of his and the horny cruel dominatrix tore into his gripping hot sissy ass destroying it totally with her victious steel hard strapon. After slamming that sissy's bunghole of his, they both climaxed uncontrollably wild.

Model(s): Rita, Donald | Number of pics: 42 | Resolution: 1504x1000

Model(s): Rita, Donald | Site: StraponSissies.com | Category: Pictures


17.02.2021
Description: With her steel hard strapon at her side, Rita is intent on doing some slamming that sissy's bunghole of Donald. The nasty dom bitch stuffed that thing deep into his tight hot sissy butt and to prove his worthiness he wasgiving her a strapon blowjob as well after that thing was deep into his tight hot sissy butt and destroys it. That hard sturdy strap on tears into the sissy's nasty hot ass and he can barely withstand the pounding that sissyboy's butthole she is doing.

Model(s): Rita, Donald | Duration: 12min 12sec | Type: HD | Size: 264mb

Model(s): Rita, Donald | Site: StraponSissies.com | Category: Videos


09.12.2020
Description: Irene, the horny cruel dominatrix needed to break in her latest rigid strapon dildo and when she met up with sissy boy Donald she knew she'd hit paydirt. He didn't know she had such a massive strap on and tried to back off by giving her a strapon blowjob to brign some mercy but she and her steel hard strapon have no mercy in mind. Soon she's crotch deep in his tight sissy anus and wearing it out. The nasty dom bitch just dominates Maurice's gripping hot sissy ass and no mercy is given.

Model(s): Irene B, Donald A | Duration: 13min 2sec | Type: SD | Size: 189mb

Model(s): Irene B, Donald A | Site: StraponSissies.com | Category: Videos


31.03.2010
Description: Rita needs to test out her rigid strapon dildo and there's no test like stuffing it deep into a tight hot sissy butt and poor fool Donald is her next victim. She got real horny at the sight of that rock hard dildo and had sissy dude giving her a strapon blowjob to moisten it up so that it would enter his nasty sweet asshole with ease.

Model(s): Rita, Donald | Number of pics: 67 | Resolution: 1504x1000

Model(s): Rita, Donald | Site: StraponSissies.com | Category: Pictures


28.09.2009
Description: Rita is into tight crossdresser butt if it's the last thing she does and getting hold of Donald in his maid outfit and slamming that sissy's bunghole is just what she's going to do. She wants nothing short of a anihilated sissy butt for all her troubles and poor dude is going to get the worst of it. She got real horny and whipped out her steel hard strapon and went to work on his tight sissy anus. She banged that butt until that rigid strapon dildo almost melts from the fury.

Model(s): Rita, Donald | Number of pics: 61 | Resolution: 1504x1000

Model(s): Rita, Donald | Site: StraponSissies.com | Category: Pictures

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All models were at least 18 years old when they were photographed or videotaped

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