13 Results Found:


06.04.2024
Description: Hold on to your seats as nasty dom bitch Jessica who has her passions red hot gets ready to totally destroy sissy boy Randolph's gripping hot sissy ass. With her strapon she's going to fuck that sissy ass and humiliate him by watching his sucking her strap on cock after it's been stuffed into his nasty hot ass. The degradation action almost breaks her hard sturdy strap on in half and the nasty dom bitch is finally satisfied with the durability of her hard sturdy strap on and the submission of her whiney man sissy.

Model(s): Jessica A, Randolph | Number of pics: 51 | Resolution: 1505x1000

Model(s): Jessica A, Randolph | Site: StraponSissies.com | Category: Pictures


18.10.2023
Description: Jessica is sleeping and whiney little sissy Randolph takes the opportunity to put on her clothes. She gets mad and they argue but the nasty bad twosome then become sexually aroused and soon a large scary strap-on is displayed. The cowering girlie boy can't wait to get that raw study strap-on stuffed up his snug little butt and next thing you know he's getting the ruthless hardcore fucking of his life. The reach total orgasm he feels almost melts that hard ripping strapon.

Model(s): Jessica A, Randolph | Duration: 14min 45sec | Type: SD | Size: 215mb

Model(s): Jessica A, Randolph | Site: StraponSissies.com | Category: Videos


20.09.2023
Description: Here comes Jess the nasty dom bitch who intends on slamming some tight hot sissy butt and none other than crossdresser Walter is her target. She starts the crossdresser off by his sucking her strap on cock getting it all wet and slimey so it can squeeze on into that gripping hot sissy ass of his. That rigid strapon dildo plows into that nasty hot ass or His and then she starts pounding that sissyboy's butthole until she totally owns it.

Model(s): Jess, Walter | Duration: 11min 59sec | Type: SD | Size: 174mb

Model(s): Jess, Walter | Site: StraponSissies.com | Category: Videos


26.07.2023
Description: Because dressing up like a lady got Randolph real fucking horny he made sure Jess was around to make him feel even hornier knowing she would treat him like a sissy boy fuck toy. She whipped out that thick meaty strapon of hers and taunted him like a puppy with a bone and when he was ready she plowed into that nasty iron grip ass of his and made him beg and whine like the bitch ass fuck he is. She enjoyed the fact that she fucked that ass of his until he became a cowering slave to her.

Model(s): Jess, Randolph | Number of pics: 44 | Resolution: 1505x1000

Model(s): Jess, Randolph | Site: StraponSissies.com | Category: Pictures


26.11.2022
Description: Randolph decided to give up that tight sissy boy butt to Jessica as her cowering butt sissy slave. She whipped out her rock hard strap on dildo and after he put on his dress and wig she tore into his tight hot sissy butt and worked him over big time. His anihilated sissy butt was totally destroyed and he submitted to the ultimate humiliation by doing some sucking ass entombed strapon cock action.

Model(s): Jessica A, Randolph | Number of pics: 64 | Resolution: 1505x1000

Model(s): Jessica A, Randolph | Site: StraponSissies.com | Category: Pictures


13.08.2022
Description: With her rock hard strap on dildo at her side, Jessica is intent on doing some slamming that sissy's bunghole of Randolph. The horny cruel dominatrix 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 slamming that sissy's bunghole she is doing.

Model(s): Jessica A, Randolph | Number of pics: 68 | Resolution: 1505x1000

Model(s): Jessica A, Randolph | Site: StraponSissies.com | Category: Pictures


18.05.2022
Description: Hot blonde Jess goes for broke to plow some nasty hot ass and when she gets her hands on Walter he'll get the business end of her hard sturdy strap on for sure. The nasty dom bitch knows no mercy when it ocmes to dishing out some hard sturdy strap on justice and poor dude just doesn't know what he's in for. She buries that massive strap on deep into his butt and then humiliates him by having him sucking her strap on cock.

Model(s): Jess, Walter | Duration: 12min 47sec | Type: SD | Size: 186mb

Model(s): Jess, Walter | Site: StraponSissies.com | Category: Videos


14.04.2021
Description: Here comes Jess the horny cruel dominatrix who intends on slamming some tight hot sissy butt and none other than crossdresser Walter is her target. She starts the crossdresser off by his sucking her strap on cock getting it all wet and slimey so it can squeeze on into that gripping hot sissy ass of his. That rigid strapon dildo plows into that nasty hot ass or His and then she starts pounding that sissyboy's butthole until she totally owns it.

Model(s): Tina, Nikola | Duration: 22min 40sec | Type: SD | Size: 332mb

Model(s): Tina, Nikola | Site: StraponSissies.com | Category: Videos


02.01.2021
Description: The young redheaded man has been blindfolded and told that he will be turned into a sissy by his bossy blonde lover. He is to submit to her desires and let her dress him in a dainty white top, a matching white skirt and a long brown wig. Once she has him all dolled up she’s going to put on a surprisingly thick strapon cock and show him what it’s like to be a real woman by fucking his ass so hard he can’t walk the next day. That’s how little bitches like him are treated.

Model(s): Jess, Walter | Number of pics: 70 | Resolution: 1505x1000

Model(s): Jess, Walter | Site: StraponSissies.com | Category: Pictures


29.08.2020
Description: Foxy ass Jessica with her suntanned ass is one nasty bitch slut and when she catches sissy boy Randolph trying on her wigs and clothes she breaks out that rigid strapon dildo to teach him a lesson! Their playing around gets horny passions up to the point they both enjoy the alter sexual playing and soon she's heading for his moist tight ass with that thick meaty strapon and goes to town on him tearing into that big meaty asshole until the both of them are almost collapsing from the frenzy.

Model(s): Jessica A, Randolph | Number of pics: 62 | Resolution: 1505x1000

Model(s): Jessica A, Randolph | Site: StraponSissies.com | Category: Pictures


27.03.2019
Description: Sissy Walter underestimated nasty dom bitch Jess and the power of her rigid strapon dildo! She 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 steel hard strapon. 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.

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

Model(s): Jess, Walter | Site: StraponSissies.com | Category: Videos


26.01.2019
Description: It's Jess planning to use her unmerciful rigid strapon dildo on Randolph the sissy has to give up that gripping hot ass just craving for a woman to do him like this. She breaks out that massive strap on and goes after dude in a friendly but stealthy manner and soon they're involved in some hot action that leads to her using that strapon in his moist tight ass.

Model(s): Jess, Randolph | Duration: 13min 24sec | Type: SD | Size: 195mb

Model(s): Jess, Randolph | Site: StraponSissies.com | Category: Videos


29.02.2012
Description: Jessica knew all about Gabriel’s man shaft fixation, so she brought a big rubber one for him to master his dick munching skills and take it up the ass. She really got kicks pushing her strap-on tool into his mouth and then making this sissy guy ready for anal. Being a good sissy, he eagerly took all the length of it up his anal passage and even volunteered for some ass-to-mouth in the end. What a dirty slut!

Model(s): Jessica, Gabriel | Number of pics: 70 | Resolution: 1505x1000

Model(s): Jessica, Gabriel | 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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