21 Results Found:


09.03.2024
Description: Freakin' fine ass Rita sure knows how to handle a rigid strapon dildo and she means to work over sissy boy Maurice with it. She gets her wet hot lady pussy so worked up when she cornholes a sissy boy in his gripping hot sissy ass that she almost cums everytime she stuffs that plastic dildo into him. She holds on tight as she pounds that massive strap on again and again into his steamy sissy butt and turns him into a whining, quivering, submissive ass slut sissy.

Model(s): Rita, Maurice B | Duration: 13min 6sec | Type: SD | Size: 190mb

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


27.12.2023
Description: Barbara was horny to use her new rigid strapon dildo and bust open a gripping hot sissy ass so who shows up but crossdresser Maurice. She whips out that massive strap on and heads straight for his steamy sissy butt like it was a bullseye. The horny cruel dominatrix got her hormones boiled up by treating the sissy ass jerk and then stuffed his tight hot sissy butt like it was a hotdog bun. She loves to fuck that sissy ass and further degraded him by making him do some sucking her strap on cock tasting his own ass.

Model(s): Barbara, Maurice | Duration: 17min 45sec | Type: HD | Size: 420mb

Model(s): Barbara, Maurice | Site: StraponSissies.com | Category: Videos


19.08.2023
Description: Trinity is going to make good use of her massive strap on on sissy boy Maurice and he submits himself by sucking her strap on cock to make sure that rock hard strap on dildo slides easily into his nasty sweet asshole. The nasty dom bitch then tears into that tight hot sissy butt of his and gives that rock hard strap on dildo a real test run. Next she starts pounding that sissyboy's butthole like crazy totally owning her whiney man sissy.

Model(s): Trinity, Maurice B | Duration: 15min 8sec | Type: SD | Size: 221mb

Model(s): Trinity, Maurice B | Site: StraponSissies.com | Category: Videos


02.08.2023
Description: Rita just loves the idea of tackling Maurice's gripping hot sissy ass and Maurice won't be complaining any as he really wants foxy Rita to be his mommy for today and give him a real good cornholing. The thought of their pending action showed that Rita got real horny and soon she took that massive strap on and started teaching Maurice a good lesson since he was such a sissyboy who didn't obey his mommy. She worked him over and made him her slave as she tore into his sweet raw bum leaving him nothing more but a wallowing sissy.

Model(s): Rita, Maurice B | Duration: 12min 54sec | Type: SD | Size: 187mb

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


15.07.2023
Description: Trinity is pissed that tranny Maurice has been stretching out her clothes and using her makeup. The whiney little sissy will have to pay and that means he'll meet the wrath of her huge monster strapon. She makes him give it a messy wet blowjob and then has him bend over doggystyle so she can shove that raw study strap-on deep in his tight nasty ass. The tranny brutal nasty screwing is fast and furious.

Model(s): Trinity, Maurice B | Duration: 12min 11sec | Type: SD | Size: 177mb

Model(s): Trinity, Maurice B | Site: StraponSissies.com | Category: Videos


13.05.2023
Description: Cute Trinity's hard sturdy strap on needed a new challenge and Maurice's tight hot sissy butt would do just nicely. She breaks out that massive strap on and starts boinging his steamy sissy butt. The horny cruel dominatrix had her hormones boiled up and soon she was plowing into his gripping hot sissy ass and began to bang that sissy butt like there was a test afterwards.

Model(s): Trinity, Maurice B | Number of pics: 70 | Resolution: 1505x1000

Model(s): Trinity, Maurice B | Site: StraponSissies.com | Category: Pictures


14.01.2023
Description: Trinity was on a bend to use her rigid strapon dildo and bust open a tight hot sissy butt and Maurice is going to be her next victim. She breaks out that rock hard dildo and heads straight for his moist tight ass like it was a bullseye. The horny cruel dominatrix got her horny passions up by treating the sissy like a bitch and then stuffed his gripping hot sissy ass like it was a sausage casing. She loves to fuck that sissy ass and further degraded him by making him do some sucking her strap on cock tasting his own ass.

Model(s): Trinity, Maurice B | Number of pics: 50 | Resolution: 1505x1000

Model(s): Trinity, Maurice B | Site: StraponSissies.com | Category: Pictures


31.08.2022
Description: Cora, the nasty dom bitch needed to break in her latest rigid strapon dildo and when she met up with sissy boy Harry 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 rock hard strap on dildo 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 tight hot sissy butt and no mercy is given.

Model(s): Cora, Harry D | Duration: 12min 12sec | Type: HD | Size: 264mb

Model(s): Cora, Harry D | Site: StraponSissies.com | Category: Videos


16.04.2022
Description: Dolled-up pussy guy Maurice behaved like a prim and proper girl when he saw Hetty’s big strapon dick; however, he had to take it into his mouth anyway. His dominant girlfriend used this kinky sissy guy like her bitch, so she wanted to slam his pooper too. So she grabbed his butt brutallygot hold of his bottom and impaled it onto her stiff rubber cock drilling the sissy until she was fully satisfied.

Model(s): Hetty, Maurice | Number of pics: 51 | Resolution: 1505x1000

Model(s): Hetty, Maurice | Site: StraponSissies.com | Category: Pictures


12.01.2022
Description: Hetty watched Maurice gagging on her rubber cock while wearing a girlie dress, a wig and nude lacy stockings. Then she hiked up the sissy guy’s skirt and lowered his sexy G-string to lick Maurice’s itching pooper before penetrating it with her scary thick strapon. The girl positioned her pussy guy and butt fucked him hard turning him into her submissive bitch.

Model(s): Hetty, Maurice | Duration: 17min 15sec | Type: HD | Size: 408mb

Model(s): Hetty, Maurice | Site: StraponSissies.com | Category: Videos


18.08.2021
Description: Freakin' fine ass blonde Trinity sure knows how to handle a hard sturdy strap on and she means to work over sissy boy Maurice with it. She gets her wet hot lady pussy so worked up when she cornholes a sissy boy in his tight hot sissy butt that she almost cums everytime she thrusts that strapon dildo into him. She holds on tight as she pounds that rock hard dildo again and again into Maurice's steamy hot butt and turns him into a whining, quivering, submissive ass slut sissy.

Model(s): Trinity, Maurice B | Number of pics: 50 | Resolution: 1505x1000

Model(s): Trinity, Maurice B | Site: StraponSissies.com | Category: Pictures


19.06.2021
Description: Turn about is fair play for a horny cruel dominatrix like Rita gets a brand new rigid strapon dildo she means to break it in by busting open a crossdresser's big meaty asshole and poor Maurice is going to be her newest victim. She'll make the crossdresser do some nasty ass to mouth after they're fucking like fiends for the ultimate humiliation. Soon she is firing up that rock hard strap on dildo and gets to slamming that sissy's bunghole like a piston, totally destroying his gooey funky butthole.

Model(s): Rita, Maurice B | Duration: 17min 39sec | Type: SD | Size: 258mb

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


15.05.2021
Description: Maurice remembered the las time Jessica had fucked that ladyboy butt ferociously of his wide open and she made sure she had her rigid strapon dildo to make a return engagement. She thoroughly enjoyed banging a ripping sissy asshole and as soon as she got him in position she started slamming that sissy's bunghole of his and the fool languished with his destroyed whiney boy ass busted open like a melon. She was getting real fucking horny stuffing that steel hard strapon of hers into his nasty sweet asshole and owned it.

Model(s): Jessica A, Maurice B | Duration: 11min 44sec | Type: SD | Size: 170mb

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


12.05.2021
Description: Gloria, the horny cruel dominatrix needed to break in her latest rigid strapon dildo and when she met up with crossdresser Cyrus she knew she'd hit paydirt. He didn't know she had such a rock hard dildo and tried to back off by sucking her strap on cock 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 tight hot sissy butt and no mercy is given.

Model(s): Gertie, Cyrus | Number of pics: 43 | Resolution: 1504x1000

Model(s): Gertie, Cyrus | Site: StraponSissies.com | Category: Pictures


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


07.12.2019
Description: With his tight sissy boy butt ready for some action, Maurice decided to get Rita's horny passions up and that's when his troubles start. She was all ready and willing to bust her open some gripping hot sissy ass and with her steel hard strapon in tow she proceeded to own his nasty hot ass. She banged that butt of his and the fool sissy started to beg for mercy. She smiled as she fucked that ladyboy butt ferociously with her hard sturdy strap on.

Model(s): Rita, Maurice B | Number of pics: 79 | Resolution: 1505x1000

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


09.02.2019
Description: It's getting Goth around here when Barbara whips out her steel hard strapon so she can beat down on crossdresser Maurice and start pounding that sissyboy's butthole of his. They're both in black with Maurice's gooey funky butthole in his leopard skin skirt and as the two get their passions red hot the girl gets busy on that gripping hot sissy ass of his. Her rock hard strap on dildo just destroys the nasty hot ass of the crossdresser and soon she's so thoroughly banged that butt that both of them pass out in sweat.

Model(s): Barbara, Maurice | Number of pics: 42 | Resolution: 1505x1000

Model(s): Barbara, Maurice | Site: StraponSissies.com | Category: Pictures


18.08.2018
Description: Rita is going to do the best she can to reduce Maurice into a cowering butt sissy slave bitch boy and if she has to take a fat juicy strap on dildo to put him in his place she'll be more than happy to do it. Maurice thinks he can just dress up and not pay the price but Rita is all geared up for banging him in that gripping hot sissy ass of his. Now he's a quivering whining sissy boy with a ravaged raw rectum and Rita is now the queen sissy boy banging bitch.

Model(s): Rita, Maurice B | Number of pics: 52 | Resolution: 1505x1000

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


19.09.2011
Description: Blonde Barbara is geared for tight crossdresser butt and using crossdresser Maurice in his rainbow tie dye skirt is when she started slamming that sissy's bunghole on the leopard skin sofa. He loves nothing more than having a anihilated sissy butt at her command. Since their significant others gone for the day the two got real horny and that's when she broke out the steel hard strapon and bones his nasty sweet asshole.

Model(s): Barbara, Maurice | Number of pics: 46 | Resolution: 1505x1000

Model(s): Barbara, Maurice | Site: StraponSissies.com | Category: Pictures


30.10.2009
Description: Trinity goes for broke to plow some sweet raw bum and when she gets her hands on Maurice he'll get the business end of her hard sturdy strap on for sure. The horny cruel dominatrix knows no mercy when it ocmes to dishing out some rigid strapon dildo 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 giving her a strapon blowjob.

Model(s): Trinity, Maurice B | Number of pics: 61 | Resolution: 1505x1000

Model(s): Trinity, Maurice B | 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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