27 Results Found:


06.04.2024
Description: These guys Jack and Morgan got together and soon a fat juicy dick got whipped out and headed straight for some nasty iron grip ass. Without hesitation he banged that butt with his hard sturdy cock and went to work. Soon that gripping transvestite ass was being screwed brutally by that rock hard penis and soon there was nothing left of that gaping steamy hot butt.

Model(s): Jack, Morgan B | Number of pics: 67 | Resolution: 1504x1000

Model(s): Jack, Morgan B | Site: GaySissies.com | Category: Pictures


02.03.2024
Description: Remembering the time he screwed sissy's bung Leonard and Jack see who has the rigid pulsing dick to get the job done. That whiney sissy asshole is so destroyd as he's porking sissy's bum leaving the sissy with nothing more than a annihilated gaping rectum for all to see. If you've everseen a sissyboy hot asshole destroyed like this you'll see how he got real horny.

Model(s): Leonard, Jack | Number of pics: 60 | Resolution: 1505x1000

Model(s): Leonard, Jack | Site: GaySissies.com | Category: Pictures


03.02.2024
Description: Both of these guys Jack and Donald knew the horny sissy bitch was due for a rigid pulsing dick to destroy his butt and make him do some degrading sucking ass entombed strapon cock. As soon as they get to fucking like fiends he takes out his thick meaty cock and begins porking sissy's bum and his conquering of that sissy's nasty hot ass is complete.

Model(s): Jack, Donald B | Number of pics: 65 | Resolution: 1505x1000

Model(s): Jack, Donald B | Site: GaySissies.com | Category: Pictures


09.12.2023
Description: This dude remembers this sissy and the last time he banged that butt with his hard sturdy cock and both were ready for another round. That dripping sissy asshole of his gets banged raw by his boyfriend who obviously knows what to do with a gripping transvestite ass when he gets hold of one. The sissy takes every inch of his boyfriend's rock hard penis and you might see smoke coming from his steamy hot butt.

Model(s): Leonard, Jack | Number of pics: 54 | Resolution: 1505x1000

Model(s): Leonard, Jack | Site: GaySissies.com | Category: Pictures


23.09.2023
Description: This sissy boy just can't wait for a fat juicy dick to slide into that gripping transvestite ass of his and that's just what he wants. He doesn't feel like a day is good unless it ends with a ravaged raw rectum and to add some of the more nastiness, some sucking ass entombed cock too. Soon he's got that hard sturdy cock deep into his gripping transvestite ass and that makes him a happy camper.

Model(s): Leonard, Jack | Number of pics: 70 | Resolution: 1505x1000

Model(s): Leonard, Jack | Site: GaySissies.com | Category: Pictures


15.07.2023
Description: Jack and Morgan know a nasty gay sissy loves to get his naughty libido up by waving his gripping transvestite ass all over the place and the guy there just had to bang that sissy butt. The gay sissy starts off by giving a blowjob so that it would squeeze easily into his nasty hot ass but the other guy has a hard sturdy cock that isn't about to show any mercy on the sissy. Soon the horny sissy bitch is howling from the punishment of that hard sturdy cock.

Model(s): Jack, Morgan B | Duration: 13min 58sec | Type: SD | Size: 203mb

Model(s): Jack, Morgan B | Site: GaySissies.com | Category: Videos


24.06.2023
Description: Wearing a dark wig and a light chiffon blouse along with red stockings this sex-starved sissy goes on the prowl for a hung guy. He starts with nasty cock-tease eager to give his lover both rimjob and blowjob until the last gets hot nuts. Now prepared for a hardcore doggystyle frenzy he enjoys anal!

Model(s): Jack, Morgan B | Number of pics: 76 | Resolution: 1504x1000

Model(s): Jack, Morgan B | Site: GaySissies.com | Category: Pictures


24.12.2022
Description: Wearing a female nighty with raunchy red hose and a thong, Horatio was about to shove a lubed butt plug into his itching sissy asshole when he was spotted by a horny gay boy. Jack was sure there was a better way to have fun than toying with a glass dildo, so he put down his pants and showed his meaty little buddy. Then this sex-starved sissy bitch started swallowing and thrusting his butt on it like mad.

Model(s): Jack, Horatio | Number of pics: 60 | Resolution: 1505x1000

Model(s): Jack, Horatio | Site: GaySissies.com | Category: Pictures


10.12.2022
Description: A gay sissy loves to have his gripping transvestite ass fucked wide open and soon a hard sturdy cock is what these two Anthony and Sebastian are going to break out. That sissy's sweet raw bum is captured and the other man starts porking sissy's bum like a jackhammer on cement. That cross dresser butt takes a brutal pounding leaving him nothing more than a cowering butt sissy slave.

Model(s): Anthony, Sebastian | Number of pics: 48 | Resolution: 1504x1000

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


29.10.2022
Description: Wanna see a raunchy crossdressing scene? Check out this frisky sissy wearing a long curly wig and a hot silky skirt that happens to barely cover his lace top stockings. He gladly opens his cheeks and positions himself to have his tightest butt banged from behind after some cock-blowing and rimming.

Model(s): Jack, Morgan B | Number of pics: 85 | Resolution: 1504x1000

Model(s): Jack, Morgan B | Site: GaySissies.com | Category: Pictures


15.10.2022
Description: Jack and Monty know a nasty gay sissy loves to get his horny passions up by waving his gripping transvestite ass all over the place and the guy there just had to fuck that sissy ass. The gay sissy starts off by giving a blowjob so that it would squeeze easily into his nasty hot ass but the other guy has a rigid pulsing dick that isn't about to show any mercy on the sissy. Soon the horny sissy bitch is howling from the punishment of that rigid pulsing dick.

Model(s): Jack, Monty B | Number of pics: 53 | Resolution: 1505x1000

Model(s): Jack, Monty B | Site: GaySissies.com | Category: Pictures


24.09.2022
Description: Two men alone Jack and Donald and one of them is going to get his whiney sissy asshole busted wide open as soon as they get their that libido up. The one man goes for haywire headed for the other dude's gripping transvestite ass with his thick meaty cock whipped out and ready. Soon the man's nasty hot ass is totally annihilated and the other man is so happy that hefucked that ass into oblivion.

Model(s): Jack, Donald B | Number of pics: 63 | Resolution: 1505x1000

Model(s): Jack, Donald B | Site: GaySissies.com | Category: Pictures


16.10.2021
Description: It's wild as Alan and Hugo see a tight hot sissy butt busted open right he'll start off with his boyfriend by sucking his cock so that his thick meaty cock will be slicked up enough so his man will be slamming that sissy's bunghole. The horny sissy bitch had no idea that his gripping transvestite ass was going to be so destroyed and he kept sucking his cock hoping for some penetration ease but no luck as dude's hard sturdy cock owns him and shoots some cum.

Model(s): Alan, Hugo | Number of pics: 50 | Resolution: 1505x1000

Model(s): Alan, Hugo | 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


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


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


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


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


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


26.10.2019
Description: These gay sissies must have their tight hot sissy butt fucked wide open and soon a hard sturdy cock is what these two blondes Elliot and Sebastian are going to break out. That sissy's raw sissy bum is captured and the other man starts porking sissy's bum like a jackhammer on cement. That tight crossdresser butt takes a brutal pounding leaving him nothing more than a cowering butt sissy slave.

Model(s): Elliot, Maurice | Duration: 12min 40sec | Type: HD | Size: 298mb

Model(s): Elliot, Maurice | 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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