62 Results Found:


05.07.2025
Description: Ernest and Morgan had to show whose hard sturdy cock was the strongest but that whiney sissy asshole of his lost and soon the guy was slamming that sissy's bunghole like crazy. The sissy ended up with a ravaged raw rectum that looked like the Channel Tunnel. Since their roommates were out of town they knew no one would rescue the sissy's sissyboy hot asshole.

Model(s): Ernest, Morgan B | Number of pics: 73 | Resolution: 1504x1000

Model(s): Ernest, Morgan B | Site: GaySissies.com | Category: Pictures


31.05.2025
Description: none

Model(s): Christie, Ernest | Duration: 13min 30sec | Type: SD | Size: 196mb

Model(s): Christie, Ernest | Site: StraponScreen.com | Category: Videos


31.05.2025
Description: When a sissy came out clad in a long blue evening gown and a matching to the outfit wig his boyfriend was eyeing him open-mouthed. Later they found out that they both were wearing sheer pantyhose underneath, and sharing their nylon fetish they got down to cock swallowing and butt digging right away.

Model(s): Randolph, Ernest | Number of pics: 42 | Resolution: 1505x1000

Model(s): Randolph, Ernest | Site: GaySissies.com | Category: Pictures


28.05.2025
Description: These two friends have never turned into lovers but they’re both gay cock lovers and it won’t be surprising to anyone when they finally consummate their bubbling desire. It’s the pantyhose that bring them together. They both share a deep love of dressing in sensual nylons and as they try on pairs they can’t help but get hard enough to screw. When that much passion and need is flowing through their bodies they have to let it out in the form of a hard screw.

Model(s): Ernest, Randolph | Duration: 11min 30sec | Type: SD | Size: 167mb

Model(s): Ernest, Randolph | Site: TryPantyhose.com | Category: Videos


17.05.2025
Description: none

Model(s): Irene A, Ernest | Number of pics: 75 | Resolution: 1525x1013

Model(s): Irene A, Ernest | Site: LadiesFuckGents.com | Category: Pictures


07.05.2025
Description: Banging a sissy boy is just what this horny lady bitch Nora intends to do to her submissive but slave Ernest. She gets her that libido up just fantasizing what is going on and soon she's in there busting out that gripping hot sissy ass of his in an unmerciful fashion making sure to fuck that sissy ass and making him make sure he's giving her a strapon blowjob like the bitch ass he is. Soon his nasty hot ass is full to the brim with that rigid strapon dildo and Nora isn't about to stop.

Model(s): Nora, Ernest | Number of pics: 52 | Resolution: 1505x1000

Model(s): Nora, Ernest | Site: StraponSissies.com | Category: Pictures


26.04.2025
Description: none

Model(s): Melanie B, Ernest | Number of pics: 38 | Resolution: 1505x1000

Model(s): Melanie B, Ernest | Site: StraponTales.com | Category: Pictures


23.04.2025
Description: none

Model(s): Alice, Ernest | Number of pics: 59 | Resolution: 1024x681

Model(s): Alice, Ernest | Site: StraponSissies.com | Category: Pictures


22.03.2025
Description: Studying her real estate manual is dominatrix Jaclyn who wants to test out her new thick scary strap-on on the nearest victim. As luck would have it, gullible dumb sucker Ernest comes along and soon will see the power of her humongous terrifying strap-on the hard way. The cowering girlie man just can't believe how ferocious this nasty milf whore can be with that humongous terrifying strap-on as she slams his snug nasty butt with some crazy unmercifully harsh screwing.

Model(s): Jaclyn, Ernest | Duration: 16min 45sec | Type: SD | Size: 243mb

Model(s): Jaclyn, Ernest | Site: LadiesFuckGents.com | Category: Videos


15.03.2025
Description: These two guys Randolph and Ernest got real horny as they have the day off together and the gay sissy tells his boyfriend he wants that rock hard penis of his to be stuffed to the max inside his gripping transvestite ass. He gets the ball rolling by giving a blowjob so it will be slippery enough to slam into his nasty iron grip ass. The horny sissy bitch then prepared himself for the onslaught of his boyfriend's rigid pulsing dick.

Model(s): Randolph, Ernest | Number of pics: 52 | Resolution: 1505x1000

Model(s): Randolph, Ernest | Site: GaySissies.com | Category: Pictures


12.03.2025
Description: Jaclyn is so nasty a slut that she's on the hunt for some big meaty asshole and Ernest is the fool who will be her victim this time around. They work each to get horny passions up and then she breaks out the strapon actionf or to dig into that gripping hot ass. Ernest was almost ready to flee for his life as she whipped out thatfat juicy strap on dildo and headed straight for his nasty hot ass. She banged that butt until he became the ultimate victim.

Model(s): Jaclyn, Ernest | Number of pics: 63 | Resolution: 1505x1000

Model(s): Jaclyn, Ernest | Site: LadiesFuckGents.com | Category: Pictures


18.12.2024
Description: none

Model(s): Ernest, Randolph | Number of pics: 69 | Resolution: 1505x1000

Model(s): Ernest, Randolph | Site: TryPantyhose.com | Category: Guys & Guys


20.11.2024
Description: none

Model(s): Melanie B, Ernest | Number of pics: 49 | Resolution: 1505x1000

Model(s): Melanie B, Ernest | Site: StraponSissies.com | Category: Pictures


09.11.2024
Description: The hot chick in the beautiful black lace dress is enjoying a glass of champagne and thinking about what she’d like to do to her slave boy. He’s on his knees on the floor and he’s waiting for her to tell him her desires, her commands and her needs. She’s feeling a certain amount of aggression running through her body which means a strapon fucking for him. Whenever she has this powerful desire she needs to pump some ass to work it out.

Model(s): Christie, Ernest | Number of pics: 52 | Resolution: 1024x681

Model(s): Christie, Ernest | Site: StraponPower.com | Category: Pictures


26.10.2024
Description: He is a man made to service women. He lives to pleasure a girl, to know that what he’s doing is turning her on and helping her to get off. He also has a bit of a nylon fetish and he is often getting caught rubbing the sexy stockings of girls all over his cock. That tends to make them angry but when he offers to service their beautiful bodies in any way possible he finds that they often take him up on it. This sexy chick is just one of many that has accepted his offer.

Model(s): Mima, Ernest | Duration: 13min 22sec | Type: SD | Size: 194mb

Model(s): Mima, Ernest | Site: NylonScreen.com | Category: Videos


19.10.2024
Description: Black lacy nylons, a silky blouse and a flying skirt transform a guy into a sissy office girl. This girlie assistant is not only pretty, but also very qualified, well, at least in giving head and taking it up the brown. Watch him showing off his professional skills right on the desk in the office.

Model(s): Ernest, Morgan | Duration: 13min 13sec | Type: SD | Size: 192mb

Model(s): Ernest, Morgan | Site: GaySissies.com | Category: Videos


16.10.2024
Description: The humiliation of doing some ass to mouth has Hilda willing to dominate sissy boy Ernest and as soon as they start sexing things up she breaks out her rock hard strap on dildo and starts pounding that sissyboy's butthole like a wild woman. His nasty hot ass is conquered brutally by her as she continues her assault on his ripping sissy asshole. With their that libido up she contines to destroy his gripping hot sissy ass.

Model(s): Hilda A, Ernest | Number of pics: 58 | Resolution: 1505x1000

Model(s): Hilda A, Ernest | Site: StraponSissies.com | Category: Pictures


12.10.2024
Description: none

Model(s): Irene A, Ernest | Duration: 16min 9sec | Type: SD | Size: 236mb

Model(s): Irene A, Ernest | Site: StraponSissies.com | Category: Videos


25.09.2024
Description: none

Model(s): Christie, Ernest | Duration: 11min 37sec | Type: SD | Size: 168mb

Model(s): Christie, Ernest | Site: StraponScreen.com | Category: Videos


18.09.2024
Description: The sissy maid is wearing a sexy yellow top and a long skirt along with a pair of high heels and he’s trying his best to keep the house clean. When his mistress comes home she sees him prancing around in his slutty outfit and the first thing she thinks about is boning his butt. She always keeps her strapon cock handy and as soon as it’s around her waist she’s ready to drive it into his anus and fuck him hard. He’s going to love her forever for that big fuck.

Model(s): Melanie B, Ernest | Number of pics: 43 | Resolution: 1505x1000

Model(s): Melanie B, Ernest | Site: StraponSissies.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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