18 Results Found:


28.04.2018
Description: Foolish Jack should know better than to take on a nasty dom bitch like Irene who is renowned for using a rigid strapon dildo to enslave her sissy boy victims. With their passions red hot they begin by him sucking her strap on cock to get it slimey enough to penetrate his moist bitch boy ass. Soon she has that rock hard strap on dildo drilling his tight helpless butt and the sissy fool howls in degradation. She totally destroys his gripping hot sissy ass and soon damn near breaks that massive strap on off in his nasty hot ass.

Model(s): Irene B, Jack | Duration: 15min 56sec | Type: SD | Size: 233mb

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


07.03.2018
Description: Jack was doomed to get his tight hot sissy butt destroyed by Irene who got real horny when she realized she would finally get to use her rock hard dildo. He got ready by sucking her strap on cock making it slippery enough to dig into his tight sissy anus. The nasty dom bitch bore down hard with her hard sturdy strap on and with both their horny passions up they both savored the power of getting his steamy hot butt fucked stupid.

Model(s): Irene B, Donald A | Number of pics: 78 | Resolution: 1505x1000

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


10.02.2018
Description: Irene is hunting for some ripping sissy asshole and when she gets hold of Jack she gets horny as fuck. She knows he needs to have his tight hot sissy butt boned to the brim with a rock hard strap on dildo and she humiliates the fool by stuffing one deep into his sweet raw bum and fucking him silly. She doesn't let up and the wild girl just tore that ladyboy ass wide open and then made him blow her hard sturdy strap on.

Model(s): Irene B, Jack | Duration: 11min 47sec | Type: SD | Size: 171mb

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


31.01.2018
Description: The sissy boy is sitting in the black leather chair when he finds a beautiful flyaway baby doll and a strapon dildo underneath his ass. Since there’s no one around he figures he might as well try it on. As it turns out there was someone watching and now she’s going to punish him for being a naughty, snooping boy and poking his nose where it shouldn’t have been. He’s going to have to take that strapon cock up his asshole and he looks like such a little slut in his lingerie.

Model(s): Marion, Jack | Number of pics: 93 | Resolution: 1505x1000

Model(s): Marion, Jack | Site: StraponSissies.com | Category: Pictures


14.10.2017
Description: For a sissy boy he sure looks good and the girl in the red stockings thinks he should be rewarded for making himself so pretty. She knows that he loves it when there’s a big strapon cock in his asshole and she can certainly make that happen for him so she pulls hers out and introduces it to his butt. It slides in easily and it starts fucking him deep, pounding him hard and making him squeal like a bitch. It’s the kind of hardcore loving that this young man really needs.

Model(s): Marion, Jack | Duration: 14min 43sec | Type: SD | Size: 214mb

Model(s): Marion, Jack | Site: StraponSissies.com | Category: Videos


23.09.2011
Description: Jack deserves to be banged that butt so he pleaded with Evelina with her long black ponytail to whip out her rigid strapon dildo bust his butt open like the sissy he is. Soon the scent of tight crossdresser bunghole fills the air as she pounds his gripping hot sissy ass like mad as she uses that rock hard dildo to destroy that moist transvestte ass of his. The nasty dom bitch just loves to get passions red hot and nothing pleases her more than fucking a tight hot sissy butt.

Model(s): Evelina, Jack | Number of pics: 74 | Resolution: 1505x1000

Model(s): Evelina, Jack | Site: StraponSissies.com | Category: Pictures


03.09.2011
Description: Jack in his rose print skirt cowering butt sissy slave who stops by Evelina's to taste her steel hard strapon which she'll stuff into his tight hot sissy butt and that's just what she wants to do. This sissy has to have a anihilated sissy butt and Evelina in her ponytail is stuffing that rigid strapon dildo deep into his tight hot sissy butt is more than he desires. The two turned on to the max and then she stuffed that massive strap on all the way up his bum and humiliates him more by watching him giving her a strapon blowjob tasting his own ass sauces.

Model(s): Evelina, Jack | Number of pics: 54 | Resolution: 1505x1000

Model(s): Evelina, Jack | Site: StraponSissies.com | Category: Pictures


18.08.2011
Description: Jack remembered the las time Evelina had fucked that transvestite butt ferociously of his and left it steaming from her hard sturdy strap on and now it's time for round two. She so enjoyed banging a ripping sissy asshole and as soon as she got him in position she started pounding that sissyboy's butthole of his and again steam erupts from his destroyed whiney boy ass busted open like a melon. She was getting real fucking horny stuffing that rock hard strap on dildo of hers into his tight sissy anus and owned it.

Model(s): Evelina, Jack | Number of pics: 90 | Resolution: 1505x1000

Model(s): Evelina, Jack | Site: StraponSissies.com | Category: Pictures


02.08.2011
Description: To prove his submissiveness, sissy Jack lets Inessa put makeup on him while he's sucking her strap on cock which she'll then stuff all the way up that gripping hot sissy ass and make him her slave. The rigid strapon dildo that she is weilding is just right for digging into a sweet raw bum and as soon as she's ready she starts pounding that sissyboy's butthole with glee. His tight crossdresser butt is soon destroyed leaving him nothing more than a cowering butt sissy slave.

Model(s): Inessa, Jack | Number of pics: 66 | Resolution: 1505x1000

Model(s): Inessa, Jack | Site: StraponSissies.com | Category: Pictures


21.07.2011
Description: This nasty dom bitch Evelina is so happy to use her rigid strapon dildo on sissy Jack who is known for doing nasty a2m action action. That rock hard strap on dildo of hers began pounding that sissyboy's butthole turning him into jelly. she uses that rigid strapon dildo to thoroughly destroy his tight hot sissy butt and she got real horny and poor dude is sorry that met up with that massive strap on.

Model(s): Evelina, Jack | Number of pics: 63 | Resolution: 1505x1000

Model(s): Evelina, Jack | Site: StraponSissies.com | Category: Pictures


30.04.2011
Description: Watch the tranny action heat up as Madeleine and Jack get on down to some large scary strap-on ruthless hardcore fucking. The nasty bad twosome become sexually aroused fast and the whiney little sissy figures things will be alright until he sees the size of that raw study strap-on. Madeleine then forces him to give her a sloppy oral sex getting it all wet and slimey so she can stuff it up his snug little butt and do some brutal nasty screwing that will please them both.

Model(s): Evelina, Jack | Duration: 14min 6sec | Type: HD | Size: 334mb

Model(s): Evelina, Jack | Site: StraponSissies.com | Category: Videos


01.10.2010
Description: After their last session where Irene fucked that ladyboy butt ferociously of Jack's the fool came back to take on her rigid strapon dildo again. Irene's strapon was more than a match for his tight sissy boy butt and she gave him a thorough slamming that sissy's bunghole until all he had left was a destroyed whiney boy ass. It's a good thing their significant others gone for the day as she got real horny with the idea that she could use her steel hard strapon again to humiliate his nasty sweet asshole and he even thanked her after she banged that butt of his.

Model(s): Irene B, Jack | Duration: 14min 51sec | Type: SD | Size: 216mb

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


06.05.2010
Description: Stupid sissy fool Cyrus is the latest victim of nasty dom bitch Trudy as she means to try out her rigid strapon dildo on him. She'll make him endure some degrading sucking ass entombed strapon cock action after they're done sexing things up she'll make sure he does. That rock hard strap on dildo of hers is viciously slamming that sissy's bunghole like a jackhammer and his gooey funky butthole is humiliated and brutalized. She smiles at destroying his tight hot sissy butt!

Model(s): Trudy, Cyrus | Duration: 16min 29sec | Type: SD | Size: 241mb

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


14.01.2010
Description: Irene helps Jack with his sissy makeup before delivering her massive strap on deep into his nasty hot ass and shows him what a nasty dom bitch she really is. That hard sturdy strap on just destroys his butt and then makes him degrade himself by having him do some ass to mouth. They then go into a marathon session of sexing things up and the sissy fool suffers the punishment of that steel hard strapon.

Model(s): Irene B, Jack | Duration: 16min 25sec | Type: SD | Size: 240mb

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


02.01.2010
Description: Blonde Irene turned on to the max after teasing sissy boy Jack and then whipped out her steel hard strapon so that she could show him who was boss and stuff his tight sissy anus. He in his lady dress and makeup howled as she banged that butt of his with her hard sturdy strap on. Her wet hot lady pussy oozed all over as she pounded his gripping hot sissy ass and then made the fool lick her rock hard dildo after it had been in his steamy sissy butt.

Model(s): Irene B, Jack | Number of pics: 63 | Resolution: 1505x1000

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


10.07.2009
Description: Irene is so the big horny fuckmeister that she's on the prowl for some tight helpless sissy boy butt and Jack is the guy she's zeroing in on and he doesn't care because he needs a mommy to get that libido up. Soon the blonde bombshell Irene is whipping out the dildoes and strapons for plowing into that tight hot sissy butt of Jack's and his sissy self loves it. Soon that fat juicy strap on dildo has plundered that sweet raw bum until Jack is her ultimate slave.

Model(s): Irene B, Jack | Duration: 13min 22sec | Type: SD | Size: 194mb

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


06.03.2009
Description: Nora is one nasty bitch slut and she means to tame poor Ernest by slamming him silly in his backdoor with a hard sturdy strap on that she brought with her for just this special occasion. Ernest thinks he can take that full measure of that massive strap on and even begins giving her a strapon blowjob to lessen the pain of the power of what Nora is going to do to him. Soon that fat juicy strap on dildo is going to work like a jackhammer in Ernest's nasty iron grip ass until both of them cum in delight.

Model(s): Nora, Ernest | Duration: 14min 52sec | Type: SD | Size: 216mb

Model(s): Nora, Ernest | Site: StraponSissies.com | Category: Videos


20.05.2008
Description: For a little sissy boy he looks pretty good and this sexy long haired brunette is hungry to penetrate his asshole. She has a strapon cock that’s always ready to go and she throws it around her waist and makes him suck on it to get the shaft nice and wet. A little lubrication on his asshole and he’s ready to be fucked like a bitch. It’s what he dreams of and it’s what happens as the dominant girl shoves her cock up his butt and really pounds him hard like a sissy.

Model(s): Marion, Jack | Number of pics: 81 | Resolution: 1505x1000

Model(s): Marion, Jack | 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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