21 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


04.11.2023
Description: Cyrus and Morris are notorious for buttfucking gay sissies and when he meets up with this sissy here he whips out his hard sturdy cock and goes to town on him. Soon this cross dresser butt is ripped wide open as the dude starts porking sissy's bum and leaves him witha smoking, annihilated gaping rectum. The sissy's sissyboy hot asshole was then filled as dude spurted hot cum.

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

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


29.07.2023
Description: This time a handsome police officer gets seduced by a gorgeous sissified guy dressed in a long gown with a green feather boa and raunchy fishnet stockings. High heels and a blonde wig add to the officer’s excitement and soon this sissy gets pumped into his mouth and butt in the horniest positions.

Model(s): Cyrus, Tommy | Duration: 14min 22sec | Type: SD | Size: 209mb

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


22.04.2023
Description: Cyrus and Walt team up and the horny sissy bitch and his lover are bigtime turned on and of course his tight hot sissy butt is going to be annihilated. His boyfriend starts to bang that sissy butt of his after the sissy was giving a blowjob and soon the popping sounds of a nasty hot ass echo around the room like a cavern. Dude's hard sturdy cock lets go and busts a wad deep into that horny sissy bitch.

Model(s): Cyrus, Walt A | Number of pics: 48 | Resolution: 1504x1000

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


31.12.2022
Description: Cyrus and Anthony had a dream this guy tore that transvestite asshole open and they knew what to do with a rigid pulsing dick. Thatwhiney sissy asshole was busted wide open as he started pounding that sissyboy's butthole leaving the sissy with nothing more than a plundered brown eye. Their passions increased and that sissyboy hot asshole was annihilated as the two turned on to the max.

Model(s): Cyrus, Anthony C | Duration: 14min 53sec | Type: SD | Size: 217mb

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


16.07.2022
Description: This long-haired sissy in his flowered blouse and skirt skips foreplay getting down to a deep throat job right away. Then he puts his legs in barely there pantyhose up having his butt cheeks parted for a meaty dick. See him getting nailed on the table and pumped hard from behind right in the cafe!

Model(s): Cyrus, John K | Duration: 12min 1sec | Type: SD | Size: 174mb

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


07.05.2022
Description: Some guys like Cyrus and Anthony can't resist busting open a tight hot sissy butt and this dude is going after his gay sissy pal with his hard sturdy cock. In no time dude is stuffing that sweet raw bum of his sissy boyfriend and then starts pounding that sissyboy's butthole like a cowboy riding a wild bronco. That cross dresser butt started gaping as his lover shoots some cum deep inside the cowering butt sissy slave.

Model(s): Cyrus, Anthony C | Number of pics: 53 | Resolution: 1504x1000

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


12.02.2022
Description: The sissified guy in a pink suit with sheer nylons and high heels makes it quite clear that he’s ready for some anal fun while seducing his neighbor into a romp on the sofa. He starts with a nice sloppy blowjob to prepare this boner for his tight ass. Don’t miss this outrageous ass-splitting frenzy!

Model(s): Cyrus, Tommy | Duration: 9min 20sec | Type: SD | Size: 135mb

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


23.10.2021
Description: This dressed to kill blond sissy in his silky attire with suntan fishnets lets his roommate get under his skirt for some warming up ass-licking right in the bathroom. Getting all steamed up he gags on the dick of his buddy preparing him to plow his itchy asshole. See the sissy getting jizzed cheeks.

Model(s): Cyrus, Desmond | Number of pics: 66 | Resolution: 1504x1000

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


10.04.2021
Description: Red lacy panties, barely black stockings, bright red silky dress and a Cleopatra wig turn this sissy into an absolute temptress. Check him out as he keeps his thighs spread wide to get anally pumped and flashes his neatly groomed ball sack just to have it creamed with gooey cum of his gay boyfriend.

Model(s): Cyrus, Tommy | Number of pics: 58 | Resolution: 1504x1000

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


16.01.2021
Description: Behold Cyrus 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 fat juicy dick then drilled into his tight slick butt 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): Cyrus, Desmond | Duration: 15min 14sec | Type: SD | Size: 221mb

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


12.12.2020
Description: It's Cyrus and Morris with his hard sturdy cock at the ready, this dude goes after his gay sissy friend's sweet raw bum and his friend isn't afraid. Soon dude is slamming that sissy's bunghole and that girlie boy is so getting his whiney sissy asshole blasted open. He ends up nothing more than a cowering butt sissy slave as his boyfriend busts a wad deep in his bum totally degrading and dominating his gay sissy flunky.

Model(s): Cyrus, Morris A | Number of pics: 49 | Resolution: 1504x1000

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


30.05.2020
Description: Check out Cyrus and Walt as he got real horny and then turned on his gay sissy boyfriend and whipped out his fat juicy dick to stuff into his nasty iron grip ass like crazy. He banged that butt and the sissy took every centimeter of that dude's hard sturdy cock so deep into his dripping sissy asshole that cum almost came out of his ears. The sissy howled as his gripping transvestite ass took the full power of his boyfriend's rock hard penis.

Model(s): Cyrus, Walt A | Duration: 18min 36sec | Type: HD | Size: 405mb

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


07.12.2019
Description: Cyrus and Tommy turned on to the max at the tought of a fat juicy dick 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 wet sissy butt raw from the inside out. His gripping transvestite ass was so annihilated by that massive bulging boner you could see smoke coming from his steamy hot butt.

Model(s): Cyrus, Tommy | Number of pics: 60 | Resolution: 1504x1000

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


13.07.2019
Description: Cyrus and Douglas know a hard sturdy cock anywhere in his vicinity gets to slam his cross dresser butt and wear it out. Soon his man is slamming that sissy's bunghole and working up a sweat that just destroys the sissy's plundered brown eye with gusto. It's a good thing their girlfriends were out of town or the sight of that tight little bum would have made them faint.

Model(s): Cyrus, Douglas A | Number of pics: 60 | Resolution: 1504x1000

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


23.06.2018
Description: Cyrus and John knows a gay sissy has a tight slick butt so they seek them out like this guy does with this nasty gay sissy and whips out his rigid pulsing dick and goes for broke. With their naughty libido up and that gay sissy sucking his cock dude aims his boner right for that moist tight ass. Soon his thick meaty cock is in full destruction mode for the gay sissy's tight helpless butt.

Model(s): Cyrus, John K | Number of pics: 42 | Resolution: 1505x1000

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


18.02.2010
Description: Cyrus and Walt get hot as his lover's rigid pulsing dick sent off it's radar, this gay sissy grabbed hold of that rock hard penis and started giving a blowjob 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 begging for mercy as his wet sissy butt gets totally owned.

Model(s): Cyrus, Walt A | Duration: 13min 19sec | Type: HD | Size: 289mb

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


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


21.04.2008
Description: This sizzling hot sissy wearing a maid uniform has got it all to make his boyfriend horny as hell. The best thing about him is his control top tights making his booty yet more desirable. Watch this fuckable slut go nasty as he kneels down to blow his buddy and puts his ass up for some backdoor work.

Model(s): Cyrus, John K | Number of pics: 45 | Resolution: 1505x1000

Model(s): Cyrus, John K | Site: GaySissies.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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