19 Results Found:


02.12.2017
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


28.10.2017
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


02.02.2011
Description: Rita turned on to the max after teasing sissy boy Donald and then whipped out her fat juicy strap on dildo so that she could show him who was boss and stuff his nasty iron grip ass. He in his lady dress and makeup howled as she banged that butt of his with her rigid strapon dildo. Her dripping tight lady pussy oozed all over as she pounded his tight hot sissy butt and then made the fool lick her massive strap on after it had been in his moist tight ass.

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

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


09.01.2011
Description: Irene needs to bang that sissy butt on a dialy basis and she finds Donald a real sissy boy and gets him to giving her a strapon blowjob to start things off. She loves to bang some nasty hot ass like it's going out of style and the nasty dom bitch really knows how to use a hard sturdy strap on and there's nothing he likes more than having a massive strap on stuffed up his backside. To make the humiliation even worse after screwing him she makes him engage in giving her a strapon blowjob.

Model(s): Irene B, Donald A | Number of pics: 50 | Resolution: 1505x1000

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


05.01.2011
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


20.12.2010
Description: Donald is such a sissy boy that he must have a ripping sissy asshole stuffed deep into his gripping hot sissy ass and horny Helga would like nothing better to do. The two of them turned on to the max and soon Irene was breaking out her rock hard dildo and heading straight for his sissy sweet raw bum. The horny cruel dominatrix whipped out that hard sturdy strap on and went to work. He was famous for doing some nasty ass to mouth and after sexing things up he proved himself.

Model(s): Helga, Donald A | Duration: 14min 43sec | Type: SD | Size: 214mb

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


25.10.2010
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


13.10.2010
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


27.09.2010
Description: Sissy Donald underestimated horny cruel dominatrix Irene and the power of her rigid strapon dildo! Helga is quite the expert at dispensing justice with her massive strap on and to prove his unworthiness, he is tested by sucking her strap on cock beginning his journey into total humiliation at that business end of a rock hard strap on dildo. she dives into that tight sissy anus of his and the nasty dom bitch tore into his tight hot sissy butt destroying it totally with her victious rock hard strap on dildo. After slamming that sissy's bunghole of his, they both came like crazy.

Model(s): Helga, Donald A | Number of pics: 92 | Resolution: 1504x1000

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


03.06.2010
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


08.04.2010
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


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


22.01.2010
Description: Helga was going to put her rigid strapon dildo to good use on Donald's gripping hot sissy ass and the sissy fool was ready to accept his punishment. They both got turned on to the max and when she broke out her massive strap on he showed his submissiveness by giving her a strapon blowjob after it had been embedded into his nasty sweet asshole for some really nasty action. The nasty dom bitch she really knows how to use a hard sturdy strap on!

Model(s): Helga, Donald A | Duration: 12min 46sec | Type: SD | Size: 185mb

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


10.01.2010
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


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


24.04.2009
Description: Blonde babe Irene is going to tear into the tight helpless sissy boy butt of Donald who is all dressed up like a woman hoping to get away with something. Soon Irene has that big fat dildo buried into Donald's gripping hot sissy ass and he's helpless to resist as that's all he wants being the kinky fucking whiney boy he is. Irene turned on to the max feeling the power of having a guy like Donald as her submissive sissy slave and she really poured it on with that massive strap on buried deep into Donald's. sweet raw bum.

Model(s): Irene B, Donald A | Number of pics: 56 | Resolution: 1505x1000

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


10.04.2009
Description: Seeing a guy dressing up like a woman gets horny passions up and when you get Helga here alone with Donald who is dressing up in women's clothing, you know his gripping hot sissy ass is doomed. Helga is breaking out the thick meaty strapon and starts going to work on this whiney boy in ways you can't imagine. She really goes to work on that sweet raw bum of Donald's and the poor fool just doesn't know what he's in for. She fucked that ass so hard that Donald almost passed out and Helga gleamed at being his dominatrix.

Model(s): Helga, Donald A | Number of pics: 89 | Resolution: 1505x1000

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


16.01.2009
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


09.01.2009
Description: This time Donald gets Helga to bust out a rigid strapon dildo and give him a lesson as after they try on some dresses and makeup he needs a lady like Helga to dive into his tight hot sissy butt and pound it good. Donald got real horny when he got all his lady makeup and dress on and then Helga knew it was time to break out that rock hard dildo and Donald started sucking her strap on cock and after he made good she started pounding his tight slick butt until he begged her for mercy.

Model(s): Helga, Donald A | Number of pics: 81 | Resolution: 1505x1000

Model(s): Helga, Donald A | 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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