23.08.2025 |
Description: A couple was kissing on the sofa when their crossdressed friend appeared on the scene. The chick was curious to see the two guys play, so she let the dude in a blond wig and girlie dress take her place. The sissy went down to suck her lover’s dick like a sex-starved male whore and then put his ass in the air for some hot butt pounding. Looks like both of the guys enjoyed that gender bender play.
Model(s): Rosa, Hubert, Silvester | Duration: 15min 31sec | Type: HD | Size: 366mb
Model(s): Rosa, Hubert, Silvester | Site: GaySissies.com | Category: Videos
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16.08.2025 |
Description: It's so wrong that these dudes turned on to the max in the upstairs office hallway and they hunger for a massive bulging boner to embed into a tight hot sissy butt. Dude starts off on the man by giving a blowjob so it'll be hard enough to bust open his nasty iron grip ass. The nasty gay sissy takes every inch of that hard sturdy cock which really gets horny passions up big time. To finish off he even starts giving a blowjob after it's been deep in his steamy hot butt.
Model(s): Maurice, Silvester | Number of pics: 58 | Resolution: 1505x1000
Model(s): Maurice, Silvester | Site: GaySissies.com | Category: Pictures
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09.08.2025 |
Description: On the sofa we find Maurice and Silvester have a rigid pulsing dick to take care of and they'll use those rock hard penises of theirs for some gay sissy sex. The sissy starts sucking his cock and soon that thick meaty cock is buried nuts deep inside that sissy's tight slick butt. The horny sissy bitch squeals with delight as his dripping sissy asshole gets totally owned.
Model(s): Maurice, Silvester | Duration: 14min 52sec | Type: HD | Size: 352mb
Model(s): Maurice, Silvester | Site: GaySissies.com | Category: Videos
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26.07.2025 |
Description: Ernie really looked lovely in a halter-neck gown and black fashion holdups, so Silvester popped a boner for this sissy at once. He wanted to push down his pink lacy thong and shove his rod deep into the sissy bum, but first he felt like checking the cock-sucking expertise of the X-dresser. Ernie didn�t disappoint his gay mate blowing him really well and taking his dick up the brown like a champ.
Model(s): Ernie, Silvester | Duration: 16min 50sec | Type: HD | Size: 398mb
Model(s): Ernie, Silvester | Site: GaySissies.com | Category: Videos
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03.05.2025 |
Description: This hot stripy dress, black hold-ups and high heels along with a blond wig and professionally done make-up turned this sissy guy into a seductively looking babe. Roland looked so sexy in his womanly outfit that Silvester didn’t bother to undress him when they began getting it on. The gay guy made this fake chick swallow his meat really deep and then hiked up the sissy’s dress to shove it where the sun never shined.
Model(s): Roland, Silvester | Duration: 12min 7sec | Type: HD | Size: 287mb
Model(s): Roland, Silvester | Site: GaySissies.com | Category: Videos
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26.04.2025 |
Description: It's time he screws sissy's bung and this dude is going to take his hard sturdy cock and slam into that gay sissy. That dude in the red and white dress will get his cross dresser butt busted wide open as he started fucking sissyboy's asshole leaving the sissy with nothing more than a plundered sore asshole.
Model(s): Maurice, Silvester | Number of pics: 56 | Resolution: 1505x1000
Model(s): Maurice, Silvester | Site: GaySissies.com | Category: Pictures
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29.03.2025 |
Description: Owen and Silvester both enjoy sexy costume play, but the bottom guy loves to play a female part, so this time he has chosen a retro style gown with white stockings and silky gloves completing his costume with a lacy sunshade. The sissy seems good at playing a chaste lady, but then his horny nature gets the best of him and he sucks and fucks like a whore for some nice gooey load.
Model(s): Owen, Silvester | Number of pics: 61 | Resolution: 1505x1000
Model(s): Owen, Silvester | Site: GaySissies.com | Category: Pictures
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08.03.2025 |
Description: Silvester resembles a shy lass on her first day, what with his glasses, pretty dress, gartered stockings and high heels. After a few cocktails he and Jacob get drunk and ready to get dirty, and they begin kissing on the mouth. Then Jacob gets bolder and begins groping his sissified girlfriend before she goes down to suck him off. Finally, the girlified dude gets to dirty ass-to-mouth like a champ.
Model(s): Jacob, Silvester | Number of pics: 59 | Resolution: 1505x1000
Model(s): Jacob, Silvester | Site: GaySissies.com | Category: Pictures
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15.02.2025 |
Description: It's pink crossdresser fun as this one starts sucking his cock of his office boyfriend and that thick meaty cock of his boyfriend responds to the action. Not one to turn down a good thing he starts porking sissy's bum like it's going out of style and the nasty gay sissy is in sheer joy of it. Soon his gripping transvestite ass is busted open so wide that the neighbors can hear that tight hot sissy butt is gaping like a manhole uncovered.
Model(s): Maurice, Silvester | Number of pics: 65 | Resolution: 1505x1000
Model(s): Maurice, Silvester | Site: GaySissies.com | Category: Pictures
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25.01.2025 |
Description: Today it�s Silvester�s turn to dress like a sissy, so he chooses a pink polo-neck sweater together with a pretty black skirt and a showy blonde wig. Looks like Edwin is surprised to see his gay buddy all girlified, but he quickly sees the bright side of things. He gropes, kisses and butt fucks Silvester as his girlfriend without bothering to peel off his sissy attire.
Model(s): Edwin, Silvester | Number of pics: 64 | Resolution: 1505x1000
Model(s): Edwin, Silvester | Site: GaySissies.com | Category: Pictures
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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