25 Results Found:


14.05.2025
Description: Sissified Owen was only too happy whoring his asshole to Alana. He was wearing his girlish clothes along with a dark-haired wig and some pretty showy make-up ready for some strapon play. His girlfriend even found cool black nylons and hot tanga panties underneath his dress, so she groped his buns, slid his panties aside and aimed her dildo right into his waiting brown hole.

Model(s): Alana, Owen | Number of pics: 89 | Resolution: 1505x1000

Model(s): Alana, Owen | Site: StraponSissies.com | Category: Pictures


18.04.2025
Description: none

Model(s): Patricia K, Owen | Number of pics: 66 | Resolution: 1024x681

Model(s): Patricia K, Owen | Site: PantyhoseLine.com | Category: Pictures


12.04.2025
Description: Alana presented her boyfriend with a golden ass toy ready to go for some role play, and Owen readily got naked craving to take that pretty toy up his ass. However, it wasn’t the only surprise the kinky chick had prepared for the guy; she parted her legs and revealed a fat strap-on cock. The guy had to suck and jump on top of it before the freaky lass boned him from behind and slid the plug into place again.

Model(s): Alana, Owen | Number of pics: 76 | Resolution: 1505x1000

Model(s): Alana, Owen | Site: LadiesFuckGents.com | Category: Pictures


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


14.12.2024
Description: Owen and Baldwin decide to become sexually aroused and that means there's going to be some raw butt fucking that will freak you out. These dudes don't let up when they take out their big meaty dicks and then get them slick and gooey from some sloppy cock sucking and now they're ready to see one of them break his gay cherry. Now the former straight guy receives an unmercifully raunchy slamming into his fat juicy bum.

Model(s): Owen, Baldwin | Duration: 15min 11sec | Type: HD | Size: 359mb

Model(s): Owen, Baldwin | Site: GaysFuckGuys.com | Category: Videos


23.11.2024
Description: Owen has just come out of the bathroom; he feels all fresh and clean, while his bi-curious roommate wants him to get very dirty. Hubert unwraps the gay hunk’s towel and makes him blow his big raging boner. After that the guys start screwing in every anal position possible and then some until they both get ready to spit some joy juice. It seems that somebody will have to wash his sticky bod again!

Model(s): Owen, Hubert | Number of pics: 70 | Resolution: 1505x1000

Model(s): Owen, Hubert | Site: GaysFuckGuys.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


16.03.2024
Description: Tonight freaky babe Alana wants to switch the roles and know how it feels to have a cock, so she takes out her big rubber cock and makes her lover take it into his mouth. Then this salacious gal pushes down his trousers to get access to his tight ass. First she lets him jump onto her fake dick and then pounds his rear doggystyle making him scream blue murder.

Model(s): Alana, Owen | Number of pics: 64 | Resolution: 1505x1000

Model(s): Alana, Owen | Site: LadiesFuckGents.com | Category: Pictures


16.08.2023
Description: none

Model(s): Patricia K, Owen | Number of pics: 98 | Resolution: 1024x681

Model(s): Patricia K, Owen | Site: PantyhoseLine.com | Category: Pictures


13.05.2023
Description: Baldwin and and Owen know that some raw butt fucking is going to make their day and that's when these two nasty gay guys get together to get it on. It doesn't take long for them to become sexually aroused and soon they whip out their big meaty dicks like they're going to have a sword fight and that means you had better be very careful. With some messy wet blowjobs to start things off you'll soon see their fat pulsing cocks disappear into their hot holes.

Model(s): Owen, Baldwin | Number of pics: 60 | Resolution: 1505x1000

Model(s): Owen, Baldwin | Site: GaysFuckGuys.com | Category: Pictures


08.10.2022
Description: Hubert was always curious about man-on-man sex and lucky for him he had a gay roommate, so one day they went for a score. Once he was giving a shoulder massage to Owen and ended up kissing the dude on the mouth. Then Own gave his straight buddy a few cock-sucking tips and they both launch into heated oral sixty-nining. Hubert learned how to give a rimjob too before impaling the bum of the man-loving freak.

Model(s): Owen, Hubert | Number of pics: 67 | Resolution: 1505x1000

Model(s): Owen, Hubert | Site: GaysFuckGuys.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


02.03.2022
Description: When Alana the horny lady fem is on the hunt for some hot submissive ass every guy should be on the lookout except Owen here. He wants that boning and he starts sucking her strapon getting it all wet and slimey so it can squeeze on into that gripping submissive butt of his which is what she really wants. That hard strap on plows into that sweet raw anus and totally owns him.

Model(s): Alana, Owen | Duration: 13min 2sec | Type: HD | Size: 307mb

Model(s): Alana, Owen | Site: StraponTales.com | Category: Videos


29.01.2022
Description: Denis and Owen were both dressed in retro style resembling two ladies gathering for tea until they produced a sizable rubber dick. Holding it in his gloved hands, the sissy began blowing it greedily once it was put in place about his girl’s waist. Then he had his polka-dot dress hiked up revealing a pair of white lacy stockings while he got his itchy butt-pussy licked and rammed hard from behind.

Model(s): Denis, Owen | Duration: 13min 33sec | Type: HD | Size: 319mb

Model(s): Denis, Owen | Site: StraponSissies.com | Category: Videos


17.11.2021
Description: Denis was shocked to find out that her neighbor was into cocks; however, some cash made her eager to join a freaky game. Horny Owen shoved his double ended dildo into the girl’s pussy hole and began licking the other end. Finally, he was ready to take the dildo up the brown with the girl fucking him from behind and in every which way until she busted his nasty butt.

Model(s): Denis, Owen | Number of pics: 86 | Resolution: 1505x1000

Model(s): Denis, Owen | Site: LadiesFuckGents.com | Category: Pictures


10.04.2021
Description: Hubert gets all boozed up and unable to rebuff the cock-loving guy’s passes. Owen tries to make the most of this intoxicated hetero boy and finally get into his pants. First he undoes the boy’s pants and pumps his dicks into his mouth, then he undresses himself to have his itchy butt pounded hard. Obviously Hubert enjoys being the one in control, so he keeps digging into this willing male butt deeper and deeper.

Model(s): Owen, Hubert | Number of pics: 57 | Resolution: 1505x1000

Model(s): Owen, Hubert | Site: GaysFuckGuys.com | Category: Pictures


17.10.2020
Description: This straight guy is giving his gay lover a sloppy cock sucking because he wants to lose his gay cherry and soon he'll have to face the wrath of the gay dude's fat pulsing cock. The gay guy is always on the lookout for straight fat juicy bums to bang and when he's done you'll see these naughty homosexual men rolling around in their own filth. They get real horny and both of them use their fat pulsing cocks to have as much fun as possible.

Model(s): Owen, Baldwin | Number of pics: 79 | Resolution: 1505x1000

Model(s): Owen, Baldwin | Site: GaysFuckGuys.com | Category: Pictures


30.01.2019
Description: Pretty maid Denis loves to take a break and fuck male ass and here's emo dude Owen who is about to meet her thick strapon dick. When she plows that iron grip asshole into him he squeals with pain and delight and the nasty dominatrix slut just goes haywire on his hot submissive ass. That thick strapon dick gets all wet and slimey slamming that submissive's bunghole and the horny lady fem smiles with sinister glee.

Model(s): Denis, Owen | Number of pics: 59 | Resolution: 1505x1000

Model(s): Denis, Owen | Site: StraponTales.com | Category: Pictures


18.01.2013
Description: You might have to duck when Owen and Baldwin get ready to shoot some semen as these two naughty homosexual men don't hold back when they get horny. They live for banging some rough anal sex and when they get real horny there's no stopping them. They whip out their big meaty dicks and give each other some messy wet blowjobs that gets them all wet and slimey so their buttslam orgy goes easy.

Model(s): Owen, Baldwin | Number of pics: 49 | Resolution: 1505x1000

Model(s): Owen, Baldwin | Site: GaysFuckGuys.com | Category: Pictures


18.10.2012
Description: April B was exploring Owen�s backdoor entrance, parting his round buttocks and inspecting his little brown hole. She was equipped with a fat strap-on dick that was ready to penetrate and plunder the rear of that handsome pussy guy. The bitchy gal dominated the action and made her pussy guy whine and squeal while she got hell-bent on destroying his nasty boy pussy.

Model(s): April B, Owen | Duration: 12min 4sec | Type: HD | Size: 284mb

Model(s): April B, Owen | Site: LadiesFuckGents.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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