22 Results Found:


23.03.2024
Description: On spotting a sissy in the process of putting on female clothes along with fishnets and heels, a hunk develops a big bulge in his jeans. Then the sissified guy goes right after it using his hungry mouth and sticks his ass in the air welcoming the fat cock thrusting up his rear passage at full force.

Model(s): Cyrus, Randolph | Number of pics: 54 | Resolution: 1504x1000

Model(s): Cyrus, Randolph | Site: GaySissies.com | Category: Pictures


17.02.2024
Description: These two mates Cyrus and Randolph know that a sissy's gripping transvestite ass needs some fucking and the sissy starts giving a blowjob so that that thick meaty cock will be ready for fucking sissyboy's asshole and showing him who is the boss. The nasty gay sissy gets his gripping transvestite ass royally destroyed and even after that cock has been in his ass he starts giving a blowjob for the ultimate degradation.

Model(s): Cyrus, Randolph | Number of pics: 54 | Resolution: 1504x1000

Model(s): Cyrus, Randolph | Site: GaySissies.com | Category: Pictures


27.01.2024
Description: A gay sissy craves some thick meaty cock to pound into his big meaty asshole and these two horny guys Randolph and Lesley intend on it. The sissy's whiney sissy asshole is just ripe for the plucking and dude just whips out his hard sturdy cock and dives right into that gripping transvestite ass totally annihilating it. Their actions got intense as they turned on to the max and man just stuffs his rock hard penis deeper into the sissy's sweet raw bum.

Model(s): Randolph, Lesley | Duration: 10min 42sec | Type: SD | Size: 155mb

Model(s): Randolph, Lesley | Site: GaySissies.com | Category: Videos


16.09.2023
Description: This nasty gay sissy had his that libido up and needed his gripping transvestite ass fucked hard so Randolph and Desmond decided to get it on. He jumped up and went to work to fuck that sissy ass and made him get on down to sucking his cock so it would be hard and stiff enough to penetrate the sissy's sweet raw bum. Soon that rigid pulsing dick was destroying that horny sissy bitch.

Model(s): Randolph, Desmond B | Duration: 14min | Type: SD | Size: 204mb

Model(s): Randolph, Desmond B | Site: GaySissies.com | Category: Videos


05.08.2023
Description: Randolph and Anthony know that when some gay whore wants some thick meaty cock stuffed up his tight hot sissy butt there's not much that will stop him. He needs to have his plundered brown eye owned and then do some degrading sucking ass entombed cock action to show his submissiveness. Dude whips out his hard sturdy cock and sends a barrage of cock deep into that gripping transvestite ass and then busts a wad to top the desert.

Model(s): Randolph, Anthony | Duration: 10min 11sec | Type: SD | Size: 147mb

Model(s): Randolph, Anthony | Site: GaySissies.com | Category: Videos


08.07.2023
Description: Randolph and Anthony hook up and the gay sissy is so horny he pounces on his mate by giving a blowjob before the man even has a chance and soon that fat juicy dick of his is doomed. Not one to turn down a good thing he starts fucking sissyboy's asshole like it's going out of style and the horny sissy bitch is in sheer joy of it. Soon his gripping transvestite ass is busted open so wide that the neighbors can hear that gripping transvestite ass is gaping like a manhole uncovered.

Model(s): Randolph, Anthony | Number of pics: 52 | Resolution: 1505x1000

Model(s): Randolph, Anthony | Site: GaySissies.com | Category: Pictures


09.10.2021
Description: This blonde gay sissy loves having his tight hot sissy butt fucked wide open on the blue chair and returns the favor to his boyfriend. A hard sturdy cock is what these two desire up one another's sweet raw bum is captured and the other man starts porking sissy's bum like a jackhammer on cement. That whiney sissy asshole takes a brutal pounding leaving him nothing more than a lusty submissive sissy.

Model(s): Benjamin, Randolph | Duration: 12min 19sec | Type: HD | Size: 291mb

Model(s): Benjamin, Randolph | Site: GaySissies.com | Category: Videos


27.02.2021
Description: This sissy looks dazzling in a little spotted dress, black tights and panties snugly covering his bulging dick when the skirt is hiked up. This fuck-doll is such a tease that only looking at him makes his gay friend want to jack off. After a short foreplay the sissy is heartily pumped up the brown.

Model(s): Randolph, Ernest | Number of pics: 53 | Resolution: 1505x1000

Model(s): Randolph, Ernest | Site: GaySissies.com | Category: Pictures


13.02.2021
Description: Randolph and Anthony is an expert at buttfucking gay sissies and when he rolls up on this gay sissy he whips out his rigid pulsing dick and gets busy busting open that cross dresser butt. As he's pounding that sissyboy's butthole that gay sissy is howling and squealing as his gaping, ravaged raw rectum starts moaning for mery. Soon his sissyboy hot asshole is so full of thick meaty cock it spews excess cum.

Model(s): Randolph, Anthony | Number of pics: 61 | Resolution: 1505x1000

Model(s): Randolph, Anthony | Site: GaySissies.com | Category: Pictures


21.11.2020
Description: Behold Randolph and Desmond as his boyfriend's rigid pulsing dick exploded out of his pants, this gay sissy grabbed hold of that rock hard penis and started sucking his cock right then and there. That thick meaty cock then drilled into his nasty iron grip ass and went to work like a jackhammer. Soon the nasty gay sissy was whining and squealing as his dripping sissy asshole gets totally owned.

Model(s): Randolph, Desmond B | Number of pics: 66 | Resolution: 1505x1000

Model(s): Randolph, Desmond B | Site: GaySissies.com | Category: Pictures


04.07.2020
Description: Time for a fat juicy dick and these two, Randolph and Ernest delight in that tight hot sissy butt getting totally annihilated. His sissy plundered brown eye is opened up bigger than a cave and he even does some nasty ass to mouth making sure all his ass sauce is tasted on that hard sturdy cock. The nasty action sees that gripping transvestite ass of his further owned.

Model(s): Randolph, Ernest | Duration: 11min 40sec | Type: SD | Size: 169mb

Model(s): Randolph, Ernest | Site: GaySissies.com | Category: Videos


18.04.2020
Description: Randolph and Desmond know when a gay sissy wants his tight hot sissy butt busted open right he'll start off with his lover by sucking his cock so that his fat juicy dick will be slicked up enough so his man will be porking sissy's bum. The nasty gay sissy had no idea that his tight hot sissy butt was going to be so owned and he kept giving a blowjob hoping for some penetration ease but no luck as dude's rigid pulsing dick owns him and busts a wad.

Model(s): Randolph, Desmond B | Number of pics: 77 | Resolution: 1505x1000

Model(s): Randolph, Desmond B | Site: GaySissies.com | Category: Pictures


15.06.2019
Description: You may scream as dude takes his hard sturdy cock and slams it into his sissy boyfriend's nasty hot ass and busts that nasty hole wide open. He's totally fucking sissyboy's asshole and soon that cross dresser butt is busted open so wide that you could drive a truck through. Soon the cowering butt sissy slave is getting that fat juicy dick almost stuck inside the sissy's gripping transvestite ass.

Model(s): Randolph, Lesley | Duration: 11min 24sec | Type: SD | Size: 165mb

Model(s): Randolph, Lesley | Site: GaySissies.com | Category: Videos


18.05.2019
Description: It's like a three ring circus when Randolph and Dan's thick meaty cock targets the dark big meaty asshole of his gay sissy buddy. The whiney sissy asshole he is after gets rammed and crammed and the sissy's gripping transvestite ass gets so plowed in that they both turned on to the max! That massive bulging boner just doesn't stop when his nasty hot ass gets mowed, making the horny sissy bitch quite happy.

Model(s): Randolph, Dan | Number of pics: 56 | Resolution: 1504x1000

Model(s): Randolph, Dan | Site: GaySissies.com | Category: Pictures


14.10.2017
Description: Randolph and Anthony were so hungry for a rigid pulsing dick to slam into his sweet raw bum that he didn't realize what was about to happen. Without hesitation his mate started pounding that sissyboy's butthole and soon that cross dresser butt was broken open wider than a subway tunnel. The sissy is so worn out he's nothing more than a lusty submissive sissy writhing about in his own filth.

Model(s): Randolph, Anthony | Duration: 12min 58sec | Type: SD | Size: 188mb

Model(s): Randolph, Anthony | Site: GaySissies.com | Category: Videos


26.11.2009
Description: Randolph and Desmond turned on to the max at the tought of a thick meaty cock pounding into that sissy's nasty iron grip ass. When the moment came he banged that butt with his hard sturdy cock and wore that dripping sissy asshole raw from the inside out. His tight hot sissy butt was so annihilated by that massive bulging boner you could see smoke coming from his steamy hot butt.

Model(s): Randolph, Desmond B | Duration: 13min 2sec | Type: SD | Size: 189mb

Model(s): Randolph, Desmond B | Site: GaySissies.com | Category: Videos


19.09.2009
Description: These two guys Randolph and Anthony got real horny as they have the day off together and the gay sissy tells his boyfriend he wants that rock hard penis of his to be stuffed to the max inside his tight hot sissy butt. He gets the ball rolling by giving a blowjob so it will be slippery enough to slam into his nasty iron grip ass. The nasty gay sissy then prepared himself for the onslaught of his boyfriend's rigid pulsing dick.

Model(s): Randolph, Anthony | Number of pics: 80 | Resolution: 1504x1000

Model(s): Randolph, Anthony | Site: GaySissies.com | Category: Pictures


26.05.2009
Description: Cyrus and Randolph like the swashbucklers of old whips his thick meaty cock around as a sword as he means to get a piece of this gay sissy's tight hot sissy butt. Soon the battle was on and the sissy's ravaged raw rectum was getting a royal fucking and to simmer things down he did some sucking ass entombed cock action. That didn't stop dude's hard sturdy cock from plowing back into his tight hot sissy butt and owning it.

Model(s): Cyrus, Randolph | Duration: 14min 26sec | Type: SD | Size: 210mb

Model(s): Cyrus, Randolph | Site: GaySissies.com | Category: Videos


24.04.2009
Description: Both of these guys Randolph and Rudolf have a rigid pulsing dick to take care of and they'll use that rock hard penis of theirs for some hardcore sex. The sissy starts giving a blowjob and soon that thick meaty cock is buried balls deep inside that sissy's tight slick butt. The nasty gay sissy squeals with delight as his dripping sissy asshole gets totally owned.

Model(s): Randolph, Rudolf | Number of pics: 58 | Resolution: 1504x1000

Model(s): Randolph, Rudolf | Site: GaySissies.com | Category: Pictures


27.02.2009
Description: Randolph and Dan will see his cross dresser butt annihilated right before your eyes so watch as this dude tears into his gripping transvestite ass like crazy. They both got real horny and then dude whipped out his rock hard penis and made a bee line for the gay sissy's sweet raw bum. The action ramped up as that nasty gay sissy took every throbbing inch of that hard sturdy cock and then did some nastier sucking ass entombed strapon cock to top things off.

Model(s): Randolph, Dan | Duration: 14min 19sec | Type: SD | Size: 208mb

Model(s): Randolph, Dan | Site: GaySissies.com | Category: Videos

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All models were at least 18 years old when they were photographed or videotaped

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