03.04.2021 |
Description: Jack and Donald love screwing sissy assholes and when he rolls up on this sissy here he whips out his hard sturdy cock and goes to work on him. Soon this whiney sissy asshole is ripped wide open as the dude starts pounding that sissyboy's butthole and leaves him witha smoking, ravaged raw rectum. The sissy's tight little bum was then filled as dude spurted hot cum.
Model(s): Jack , Donald B | Duration: 18min 34sec | Type: SD | Size: 271mb
Model(s): Jack , Donald B | Site: gaysissies.com | Category: Videos
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17.03.2021 |
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: 1000x1505
Model(s): Evelina , Jack | Site: straponsissies.com | Category: Pictures |
23.01.2021 |
Description: Evelina was a true dominatrix at heart and she decided that her nude male sub Jack needed some disciplining. She took out her whip and wore her strapon cock to punish and fuck this pussy boy silly. She pounded the guy from behind, did it side to side, nailed his backdoor to the bed and made him go for a steamy butt ride before she was fully satisfied with her job.
Model(s): Evelina , Jack | Number of pics: 70 | Resolution: 1000x1505
Model(s): Evelina , Jack | Site: straponpower.com | Category: Pictures |
16.01.2021 |
Description: Sex filthy young whore Jessica is laying in wait for the unsuspecting Jack with her massive fat strap-on at the ready. The woman can't wait to stuff that humongously scary strap-on in his nasty tight ass and give him the rough merciless fucking he deserves. She will just totally own him with a ferocious butt screwing adventure that will have him reaching an awesome total orgasm that he'll never forget. The filthy butt fucking proves right as that big thick strapon almost breaks.
Model(s): Jessica A , Jack | Number of pics: 54 | Resolution: 1000x1506
Model(s): Jessica A , Jack | Site: straponpower.com | Category: Pictures |
05.01.2021 |
Description: Sweet in her yellow skirt and sexy elegant pantyhose is Gwendolen who is showing off that girl's tight booty to geek boy Jack. Because she's such one horny show off she has lucky his throbbing rigid dick ready to explode and he hasn't even stuffed it in her face yet. That didn't last long as she now has that fat dick stuffed inside her snug sweet cunt and he gets to tearing that sweet stuff up to the point the room is beginning to sweat. Soon he's pumping a ton of his gooey white cum deep inside that good pussy.
Model(s): Gwendolen , Jack | Number of pics: 71 | Resolution: 1505x1000
Model(s): Gwendolen , Jack | Site: pantyhoseline.com | Category: Pictures |
14.11.2020 |
Description: In a contest these two Jack and Monty had to show which hard sturdy cock was the strongest but that cross dresser butt of his lost out and soon the man was porking sissy's bum like crazy. The sissy ended up with a ravaged raw rectum that looked like a blown up mine shaft. Since their roommates gone for the day they knew no one would rescue the sissy's sissyboy hot asshole.
Model(s): Jack , Monty B | Duration: 14min 29sec | Type: SD | Size: 211mb
Model(s): Jack , Monty B | Site: gaysissies.com | Category: Videos
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30.09.2020 |
Description: It doesn't take these boys long to be turned on as they exchange roses for some thick meaty penis and that green bedspread is like fertile ground for them. He plowed into that tight slick butt and he was helpless to resist as they both worked themselves into a fury of horniness as he used that cock and fucked that pantyhose ass.
Model(s): Jack , Leonard | Number of pics: 90 | Resolution: 1000x1505
Model(s): Jack , Leonard | Site: trypantyhose.com | Category: Pictures |
25.07.2020 |
Description: Regina is a fat butt mature who is about to fulfill young Jack's fantasies of bagging some nasty mature cunt. She shows that fat juicy ass of hers off and he wants every bite to count so he whips out his rock hard boner and plows right into that tight soft pussy and delicious meaty ass of hers until he can't hold his cum in any longer. He goes a few more thrusts and kapow! He busts a hot wad of spuzz deep inside her tight pussy and butt.
Model(s): Regina A , Jack | Duration: 14min 55sec | Type: HD | Size: 354mb
Model(s): Regina A , Jack | Site: actionmatures.com | Category: Videos
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08.04.2020 |
Description: Older mom babe Regina is horny for a hard youngman's dick and of course a dose of a fat juicy load so she seduces young Jack. The dark haired nasty nylon pantyhose slut props those big tits and big ass up against that throbbing youth's cock and she gets to work on his young, pulsing hunk's cock. Soon he's is deep inside that dripping tight pantyhose pussy and fucking her silly.
Model(s): Regina A , Jack | Number of pics: 84 | Resolution: 1000x1505
Model(s): Regina A , Jack | Site: maturesandpantyhose.com | Category: Pictures |
14.03.2020 |
Description: This fiery mommy was clad in fishnets from top to toe, she hoped this revealing outfit would help her to seduce her sexy toy boy. Jack was about to leave, but Isabella didn’t want him to go until he fucked her itching mature ass. She munched on his fresh meat sticking up her tasty bottom part eager to make him ready for a deep anal plunge. Watch this lusty red-haired milf getting plowed really hard.
Model(s): Isabella A , Jack | Duration: 11min 44sec | Type: HD | Size: 278mb
Model(s): Isabella A , Jack | Site: momsgiveass.com | Category: Videos
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26.02.2020 |
Description: Two guys playing on the green bedspread has one whipping out his rigid meaty cock and zeros in on him so that the room will be rocking. He has only one thing in his imagination and that's going for broke on his gripping pantyhose ass and of course his boyfriend falls prey to his dominant ways and he doesn't stop when he takes that massive hard dick and tears into him. Soon he is owning him and his moist tight ass and he is reduced to a quivering sissy fool who loves it when a man dominates him like this.
Model(s): Jack , Leonard | Duration: 18min 51sec | Type: HD | Size: 447mb
Model(s): Jack , Leonard | Site: trypantyhose.com | Category: Videos
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10.08.2019 |
Description: These two mates Jack and Donald know that a sissy's gripping transvestite ass needs some fucking and the sissy starts sucking his cock so that that thick meaty cock will be ready for porking sissy's bum and showing him who is the boss. The nasty gay sissy gets his gripping transvestite ass royally annihilated and even after that cock has been in his ass he starts sucking his cock for the ultimate degradation.
Model(s): Jack , Donald B | Duration: 11min 58sec | Type: SD | Size: 173mb
Model(s): Jack , Donald B | Site: gaysissies.com | Category: Videos
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19.07.2019 |
Description: You've got to hand it to Jack because he's about to get it on with this fine babe Gwendolen and that means his throbbing hunk's cock is going to go slam dunk into that nasty nylon pantyhose whore cunt of hers that will make both of them cum in waves. After some tonguing nylon pantyhosed legs he starts slamming that nylon pantyhose whore pussy and the juices are really flowing now. Her tight juicy nylon pantyhose vagina is devouring every centimeter of cock he's got and soon the two are swimming in their own sex sauces.
Model(s): Gwendolen , Jack | Duration: 14min 19sec | Type: HD | Size: 339mb
Model(s): Gwendolen , Jack | Site: pantyhoseline.com | Category: Videos
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10.07.2019 |
Description: Poor Jack is going to get a steel hard strapon stuffed up his tight hot sissy butt by sex hungry vixen Irene. She won't stop until she rules over his anihilated sissy butt and forces the sissy to do some nasty sucking ass entombed strapon cock humiliation. With that hard sturdy strap on in tow she begins banging that gripping hot sissy ass of his and she's gotten got real horny by her feat. . The massive strap on action is now complete giving her a strapon blowjob tight sissy anus.
Model(s): Irene B , Jack | Number of pics: 75 | Resolution: 1000x1505
Model(s): Irene B , Jack | Site: straponsissies.com | Category: Pictures |
22.06.2019 |
Description: Horatio is a cock loving transvestite who enjoys dressing up like a madam and getting dirty with male friends. His outfit seems very elegant with those pearls, elbow long gloves and black hosiery, so Jack is soon all over him groping and touching his hot sissy butt. The guys start with mouth kisses and then this sissified fuck-mate has to give head and eventually open up his backdoor like a good sissy slut.
Model(s): Jack , Horatio | Duration: 14min 24sec | Type: HD | Size: 341mb
Model(s): Jack , Horatio | Site: gaysissies.com | Category: Videos
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13.04.2019 |
Description: Here's another nasty bitch slut, brunette Jessica who finds a rigid strapon dildo while doing some house cleaning. The sex toy gets her horny passions up and she then starts thinking of Jack's steamy hot butt meaning the dude was doomed. The woman takes that fat juicy strap on dildo and rams it into that big meaty asshole of his until he's squealing like a pig and she makes him suck his own ass sauce off that fat juicy strap on dildo.
Model(s): Jessica A , Jack | Number of pics: 54 | Resolution: 1000x1506
Model(s): Jessica A , Jack | Site: ladiesfuckgents.com | Category: Pictures |
23.02.2019 |
Description: The nasty domina in red gloves and tights belongs to law enforcement authorities, so any disobeying will be severely punished. Jack tries to do his best but still can never satisfy this dominatrix, so despite his quite nice mouth jobs, he has to open up his butt too. Being Madeleine’s sex pet, he does whatever she asks him to do, and if it must be anal, so be it!
Model(s): Madeleine , Jack | Duration: 11min 16sec | Type: HD | Size: 266mb
Model(s): Madeleine , Jack | Site: straponpower.com | Category: Videos
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04.08.2018 |
Description: Horatio had dressed up like a lady finishing this female attire with long lacy gloves and suspender tights, however, deep inside he remained a dirty sissy slut craving for a raw butt fuck. He wrapped his gloved hands around Jack’s eager dick and went for some profound cock sucking before welcoming his lover’s stiff boner up his greedy sissy asshole. In the end he was happy to leave in the jizzed nylons.
Model(s): Jack , Horatio | Number of pics: 68 | Resolution: 1000x1505
Model(s): Jack , Horatio | Site: gaysissies.com | Category: Pictures |
01.08.2018 |
Description: Ponytailed Rosa needs to screw man butt and in comes Jack seeing her black strapon starts sucking her strapon to start things off. She loves to bang some nasty hot shitter like it's going out of style and the nasty dominatrix slut busts out that phat strapon dildo. Dude so loves a stone hard dildo rammed up his backside that he even degrades himself by blowing her strapon after it was buried in his asshole.
Model(s): Rosa , Jack | Duration: 14min 27sec | Type: HD | Size: 341mb
Model(s): Rosa , Jack | Site: straponscreen.com | Category: Videos
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07.07.2018 |
Description: Naughty horny sniveling punk Jack is craving a something up his snug little butt and here comes dirty milf slut Madeleine to satisfy him. She breaks out her massive fat strap-on and goes to work on the dirty submissive guy. They go sexually aroused and get into some filthy butt fucking that causes steam to rise in the bedroom. In her fishnet body stocking the filthy young whore rips into his snug little butt with that humongously scary strap-on big time.
Model(s): Evelina , Jack | Duration: 12min 50sec | Type: HD | Size: 304mb
Model(s): Evelina , Jack | Site: straponpower.com | Category: Videos
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