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
|
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
|
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
|
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
|
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
|
