30 Results Found:


30.11.2024
Description: It's stairway love with Maurice and Silvester's rigid pulsing dicks seek out their cross dresser butts of theirs and soon one was fucking sissyboy's asshole like crazy. The sissy ended up with a plundered brown eye that looked like a blown up mine shaft. Since their roommates gone for the day they knew no one would rescue the sissy's tight little bum.

Model(s): Maurice, Silvester | Number of pics: 55 | Resolution: 1505x1000

Model(s): Maurice, Silvester | Site: GaySissies.com | Category: Pictures


28.09.2024
Description: Both of these guys knew the horny sissy bitch in his lingerie was due for a hard sturdy cock to destroy his butt and make him do some degrading sucking ass entombed strapon cock that's so filthy. As soon as they get to sexing things up he takes out his thick meaty cock and begins fucking sissyboy's asshole and his conquering of that sissy's gooey funky butthole in the bedroom there being narcissistic in the mirror.

Model(s): Paul A, Silvester | Duration: 15min 3sec | Type: HD | Size: 357mb

Model(s): Paul A, Silvester | Site: GaySissies.com | Category: Videos


24.08.2024
Description: Sylvester and Connor get together and soon his thick meaty cock gets ready to destroy the other's tight slick butt. Without hesitation he fucked that ass with that rigid pulsing dick of his and owns that dude. Soon that tight hot sissy butt is so busted open by that massive bulging boner that the only thing left of the sissy boy is a destroyed steamy hot butt.

Model(s): Maurice, Silvester | Number of pics: 71 | Resolution: 1505x1000

Model(s): Maurice, Silvester | Site: GaySissies.com | Category: Pictures


20.07.2024
Description: When Owen wears a womanly gown with nylons and has his face made up, you won�t recognize a boy in him. Today this sissy feels like going for some costume play, and his boyfriend Silvester is game too, so they put on vintage attires before getting it on. You�ll see the sissified dude gobbling on his gay buddy�s cock before spreading his nyloned legs to get ass fucked too.

Model(s): Owen, Silvester | Duration: 21min 30sec | Type: HD | Size: 509mb

Model(s): Owen, Silvester | Site: GaySissies.com | Category: Videos


06.07.2024
Description: Watch as this sissy gobbles the thick meaty cock of his boyfriend who then goes for that tight slick butt of the sissy in his purple shirt. Without hesitation he fucked that ass with his rigid pulsing dick and went to work. Soon that tight hot sissy butt was being screwed brutally by that rock hard penis and soon there was nothing left of that gaping moist tight ass.

Model(s): Maurice, Silvester | Duration: 11min 49sec | Type: HD | Size: 279mb

Model(s): Maurice, Silvester | Site: GaySissies.com | Category: Videos


29.06.2024
Description: Now look at these two smartened up crossdressers Silvester and Jacob taking out a carton filled with dildos and getting ready to put them to good use. They both wear make-up and cute woman�s frocks completed with fine nylon holdups and thongs eager to wrap their hot mouths around some hard dildo toy before pushing to the side girlie panties and getting ass fucked by turns.

Model(s): Jacob, Silvester | Duration: 19min 18sec | Type: HD | Size: 456mb

Model(s): Jacob, Silvester | Site: GaySissies.com | Category: Videos


01.06.2024
Description: Today Silvester is wearing a pretty blue dress and sexy spike heels completing his girlie outfit with a string of beads and a flower in the hair to surprise his handsome male date. As soon as Jacob feels the sissy�s painted lips lock around his stiffening cock, he begins enjoying this pervy gay-sissy sex too. Then he slides aside the sexy lacy G-string of the sissy guy and gives him more than he�s bargained for.

Model(s): Jacob, Silvester | Number of pics: 54 | Resolution: 1505x1000

Model(s): Jacob, Silvester | Site: GaySissies.com | Category: Pictures


27.04.2024
Description: When this dude starts porking sissy's bum the room starts to sweat and pretty soon the sissy here will end up with a plundered brown eye that will look like the Grand Canyon. The sissy gives up that sissyboy hot asshole as they both turned on to the max and was met with his boyfriend's fat juicy dick that almost gets stuck in his nasty iron grip ass.

Model(s): Maurice, Silvester | Number of pics: 57 | Resolution: 1505x1000

Model(s): Maurice, Silvester | Site: GaySissies.com | Category: Pictures


16.03.2024
Description: This nasty gay sissy punk rocker had his horny passions up and needed his gripping transvestite ass fucked hard so Maurice and Silvester rock things up. He jumped up and went to work to bang that sissy butt and made him get on down to giving a blowjob so it would be hard and stiff enough to penetrate the sissy's gay sissy ass. Soon that hard sturdy cock was destroying that nasty gay sissy.

Model(s): Maurice, Silvester | Number of pics: 71 | Resolution: 1505x1000

Model(s): Maurice, Silvester | Site: GaySissies.com | Category: Pictures


30.12.2023
Description: This sissy in pink puts down the pool cue and picks up a fat juicy dick to pound into his big meaty asshole and these dudes get it on. The sissy's cross dresser butt is just ripe for the plucking and dude just whips out his rigid pulsing dick and dives right into that tight hot sissy butt 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 nasty hot ass.

Model(s): Maurice, Silvester | Number of pics: 63 | Resolution: 1505x1000

Model(s): Maurice, Silvester | Site: GaySissies.com | Category: Pictures


21.10.2023
Description: Nasty Silvester used this sissified boy as his personal assistant, so he preferred him to smoke his cock instead of a cig. On undoing his pants this bossy dude pushed his rod right into the dolled-up sissy�s mouth before spreading his male-to-female sec on the sofa to get access to her sissy ass. Ernie got butt fucked in the most twisted way right in his stockings and high heels.

Model(s): Ernie, Silvester | Number of pics: 63 | Resolution: 1505x1000

Model(s): Ernie, Silvester | Site: GaySissies.com | Category: Pictures


01.07.2023
Description: Sylvester and Connor will see who the horny sissy bitch is as they get horny passions up and jump into that gripping transvestite ass. Watch as he starts to [fuck that sissy ass|bang that sissy buttsucking his cock. This is the filthiest action that shows that sissy boy getting his nasty hot ass totally busted open and totally owns that horny sissy bitch.

Model(s): Silvester, Connor A | Number of pics: 56 | Resolution: 1505x1000

Model(s): Silvester, Connor A | Site: GaySissies.com | Category: Pictures


29.04.2023
Description: These dudes got real horny as they play around the house and soon a massive bulging boner pops out and the fun really begins. Dude so burrows his boner into that tight hot sissy butt and further humiliates the sissy by making him to giving a blowjob so it'll be hard enough to bust open his nasty iron grip ass again. The nasty gay sissy takes every inch of that rigid pulsing dick and soon there's spuzz splattered deep into that moist tight ass.

Model(s): Silvester, Connor A | Number of pics: 43 | Resolution: 1505x1000

Model(s): Silvester, Connor A | Site: GaySissies.com | Category: Pictures


08.10.2022
Description: Dude in the powder blue hoodie is all up in that tight hot sissy butt of that gay sissy and he's even giving a blowjob after it has been in his ass. That thick meaty cock will be ready for fucking sissyboy's asshole and showing him who is the boss. The horny sissy bitch gets his tight hot sissy butt royally annihilated and even after that cock has been in his ass he starts giving a blowjob for the ultimate degradation.

Model(s): Benjamin, Silvester | Number of pics: 72 | Resolution: 1505x1000

Model(s): Benjamin, Silvester | Site: GaySissies.com | Category: Pictures


27.08.2022
Description: It’s hard to recognize a guy in this sexy hottie clad in a retro green gown, yet it’s Owen, a dirty crossdressing kinkster who feels like going for some pervy costume play. Taking a good jolt of booze from his flask he picks up a receiver and dials his friend’s number. Soon Silvester joins this dressy sissified boy and makes him wrap his painted lips around his dick before jumping on top of his cock.

Model(s): Owen, Silvester | Number of pics: 71 | Resolution: 1505x1000

Model(s): Owen, Silvester | Site: GaySissies.com | Category: Pictures


15.01.2022
Description: Wearing this dark-haired wig with a pretty summer dress and a pair of black stockings, sissy Rubio was sure he looked very pretty and ladylike. However, Silvester felt like going for a score, so he didn’t bother to behave gentlemanlike, but paid the feminized dude for a quickie. Rubio took the money and bobbed his head up and down blowing the gay guy’s dick before opening up his pussy guy butt for him.

Model(s): Silvester, Rubio | Duration: 11min 33sec | Type: HD | Size: 272mb

Model(s): Silvester, Rubio | Site: GaySissies.com | Category: Videos


13.11.2021
Description: In the bedroom, this sissy takes on a thick meaty cock and these two dudes Maurice and Silvester delight in that gripping transvestite ass getting totally annihilated. his sissy ravaged raw rectum is opened up bigger than a cavern and he even does some nasty sucking ass entombed strapon cock making sure all his ass sauce is tasted on that rigid pulsing dick. The nasty action sees that gripping transvestite ass of his further owned.

Model(s): Maurice, Silvester | Number of pics: 57 | Resolution: 1505x1000

Model(s): Maurice, Silvester | Site: GaySissies.com | Category: Pictures


02.10.2021
Description: Dressing up like a freaky alt gal, Hubert tried to put the moves on Silvester and the last finally gave in to the sissy guy’s heated kissing and fondling. Finally Hubert went down and whipped out the gay guy’s cock to pump it into his hungry sissy mouth. He sucked him stiff and then got his footless tights and red thong pushed down for some vigorous butt pounding from behind.

Model(s): Hubert, Silvester | Number of pics: 89 | Resolution: 1505x1000

Model(s): Hubert, Silvester | Site: GaySissies.com | Category: Pictures


17.07.2021
Description: Jacob was wearing a hot summer dress together with black seamed stockings and high heels driving Silvester crazy with his sexy crossdresser outfit. They didn�t even make it to the bedroom as the passion hit, and these kinky gay men were all over each other. Then the sissy knelt on the sofa to suck off his buddy before opening up his thong clad butt for him. They both loved such hit-and-run sex.

Model(s): Jacob, Silvester | Duration: 10min 49sec | Type: HD | Size: 255mb

Model(s): Jacob, Silvester | Site: GaySissies.com | Category: Videos


24.04.2021
Description: Two men alone, both in their orange outfits and one of them is going to get his cross dresser butt rammed unmercifully as their horny passions up and the blue sofa will hold up to the action. The one man goes buck wild for the other dude's tight hot sissy butt 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 hebanged that butt into oblivion.

Model(s): Benjamin, Silvester | Number of pics: 56 | Resolution: 1505x1000

Model(s): Benjamin, Silvester | 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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