Silvester



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: 1000x1505

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: 1000x1505

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: 1000x1505

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: 1000x1505

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


12.03.2022
Description: This horny sissy bitch in his hot pink outfit had his that libido up and needed his tight hot sissy butt fucked and that's just what his boyfriend is going to do. He jumped up and went to work to fuck that sissy ass and made him get on down to giving a blowjob so it would be hard and stiff enough to penetrate the sissy's sweet raw bum. Soon that rigid pulsing dick was destroying that horny sissy bitch.

Model(s): Paul A , Silvester | Number of pics: 51 | Resolution: 1505x1000

Model(s): Paul A , Silvester | Site: gaysissies.com | Category: Pictures


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: 1000x1505

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


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


30.01.2021
Description: Jacob was wearing a cute polka-dot dress and classy FF stockings craving to get screwed like a female by his gay boyfriend Silvester. The latter got so horny that he didn�t bother to take off his suit eager to nail down this pretty sissy on the spot. He kissed the crossdressed cutie on the mouth, worked her puckered hole and fucked her mouth before shoving his cock where the sun didn�t shine.

Model(s): Jacob , Silvester | Number of pics: 58 | Resolution: 1000x1505

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


01.08.2020
Description: Putting on a frock and having a womanly hairdo, Jacob acts like Silvester�s mistress. The sissy is so horny for a fuck that he doesn�t wait for his gay lover to get out of his office suit and goes for some bunny fuck instead. This fake mistress pushes her thong aside to get her butt licked in 69 while she gets busy gagging on a dick. In the end the sissified dude gets raw anal and tastes some cum.

Model(s): Jacob , Silvester | Number of pics: 52 | Resolution: 1000x1505

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


08.06.2019
Description: This sissy almost stampedes his boyfriend for that rigid pulsing dick and his boyfriend is all ready to deliver that rock hard penis to his sissy bitch boy. The gay sissy starts giving a blowjob so that his fat juicy dick will be slick and wet enough to slide into his tight slick butt without destroying it. However the horny sissy bitch didn't realize his boyfriend's dick was too big for his wet sissy butt and that leads to one gripping transvestite ass being blasted wide open.

Model(s): Silvester , Connor A | Number of pics: 48 | Resolution: 1000x1505

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


09.03.2019
Description: Gay sissies just love to get that gripping transvestite ass of theirs rocked open by a hard sturdy cock and that's what these two are doing right here. That sissy boy's nasty hot ass propped high in the air and his man starts fucking sissyboy's asshole like a jackhammer on cement. That whiney sissy asshole gets wiped out by the brutal butt banging and that's the life of a lusty submissive sissy.

Model(s): Maurice , Silvester | Number of pics: 55 | Resolution: 1000x1505

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


06.10.2012
Description: Nasty Ernie put on a girlie dress along with fashion holdup nylons and pumps to lure his gay boyfriend into a hot anal fuck. Silvester liked the looks of his girlified mate, and soon he was inspecting the x-dresser�s bum. He was surprised to find a toy plugging the sissy�s rear, but then he took it out replacing it with his sturdy meaty shaft instead. Man, they went bumming in the most twisted way!

Model(s): Ernie , Silvester | Number of pics: 68 | Resolution: 1505x1000

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


22.09.2012
Description: Being a real blonde, this sissy loved wearing pink; he was a cock-loving slut too. Watch Silvester getting all dolled-up for his hunky male friend Edwin and acting like his slutty blonde girlfriend. The girlified dude played it by the book going down to give head and then opening up his booty in sexy red thong for some pretty intense cornholing. In the end the sissy got his nasty butt glazed with cream.

Model(s): Edwin , Silvester | Number of pics: 53 | Resolution: 1000x1505

Model(s): Edwin , Silvester | Site: gaysissies.com | Category: Pictures


04.02.2012
Description: Hubert wanted to surprise his nerdy lover, so he made up his face and dressed up like a sassy call girl. Well, it was a surprise all right, and Silvester’s cock stirred into action at once. Then the dirty sissy bitch pulled down the guy’s pants and closed his puffy lips around his gay lover’s shaft. Finally the geeky boy slid the crossdresser’s red G-string aside and entered his eager backdoor.

Model(s): Hubert , Silvester | Number of pics: 75 | Resolution: 1000x1505

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


25.06.2011
Description: These two gays got real horny and the crossdressing one couldn't wait to have that thick meaty cock of his buddy's pounding into his tight slick butt in the bedroom. When the time came he fucked that ass with his hard sturdy cock and wore that dripping sissy asshole raw from the inside out. His gripping transvestite ass was so annihilated by that massive bulging boner you could see atomic steam coming from his steamy hot butt.

Model(s): Paul A , Silvester | Number of pics: 60 | Resolution: 1505x1000

Model(s): Paul A , 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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