13 Results Found:


16.11.2024
Description: On the hunt for some thick meaty cock are legendary gays Desmond and Lewis and this dude is going to satisfy that tight hot sissy butt of his sissy friend. The sissy is hoping to end the day with a plundered brown eye and even do some extreme nasty sucking ass entombed cock that they both enjoy. Dude whips that rigid pulsing dick around like a sword and destroys that tight hot sissy butt and then shoots some cum deep inside him.

Model(s): Desmond, Lewis | Duration: 16min 50sec | Type: SD | Size: 246mb

Model(s): Desmond, Lewis | Site: GaySissies.com | Category: Videos


31.08.2024
Description: Fancy a bit of crossdressing and gay uniform fuck? In this case you’ll love to see the most fuckable sissy ever, wearing his cute curly wig, miniskirt and pair of net stockings with a plain welt, getting drilled by a policeman from behind and in cowgirl style with a massive cum explosion on cheeks.

Model(s): Desmond, Lewis | Number of pics: 76 | Resolution: 1504x1000

Model(s): Desmond, Lewis | Site: GaySissies.com | Category: Pictures


09.09.2023
Description: Wanna see a frisky sissy guy seducing a gay chap while wearing his frivolous dress and barely visible tights? They go slowly at it, but soon this heated sissy starts fishing for the guy’s dick and pumps it into his mouth before they’re ready to try anal pile driver. This scene will rock your socks!

Model(s): Frank B, Lewis | Number of pics: 40 | Resolution: 1505x1000

Model(s): Frank B, Lewis | Site: GaySissies.com | Category: Pictures


11.03.2023
Description: A sissy gay guy always is after some thick meaty cock to pound into his big meaty asshole and these two, Lewis and Hugo intend on it. The sissy's cross dresser butt is just ripe for the plucking and dude just whips out his hard sturdy cock and dives right into that gripping transvestite ass totally annihilating it. Their actions got intense as they got real horny and guy just stuffs his rock hard penis deeper into the sissy's nasty hot ass.

Model(s): Lewis, Hugo | Number of pics: 49 | Resolution: 1505x1000

Model(s): Lewis, Hugo | Site: GaySissies.com | Category: Pictures


04.03.2023
Description: Lewis and Connor had to show whose rigid pulsing dick 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 gone for the day they knew no one would rescue the sissy's sissyboy hot asshole.

Model(s): Lewis, Connor C | Number of pics: 40 | Resolution: 1505x1000

Model(s): Lewis, Connor C | Site: GaySissies.com | Category: Pictures


08.08.2020
Description: Watch Frank and Lewis in his gay sissy costume turned on to the max and the sissy just had to have himself some massive bulging boner or he would just burst. He started sucking his cock and gobbling that knob so it would slip into his tight slick butt where it would hopefully turn this nasty gay sissy inside out. Soon that rigid pulsing dick was doing it's job and with their naughty libido up there was no mercy on that steamy hot butt.

Model(s): Frank B, Lewis | Number of pics: 51 | Resolution: 1505x1000

Model(s): Frank B, Lewis | Site: GaySissies.com | Category: Pictures


18.07.2020
Description: Lewis and Hugo are craving a fat juicy dick to be rammed deep up his gripping transvestite ass, this gay sissy invites his neighbor. He didn't realize that he'd soon be left with a ravaged raw rectum that would look like an exploded mineshaft. Duds so degraded the sissy he forced him to do some sucking ass entombed cock action and the gay sissy gobbled down that hard sturdy cock after it had been buried deep inside his tight hot sissy butt and fucked it raw.

Model(s): Lewis, Hugo | Duration: 12min 1sec | Type: SD | Size: 174mb

Model(s): Lewis, Hugo | Site: GaySissies.com | Category: Videos


24.12.2009
Description: Lewis and Connor know that a sissy's gripping transvestite ass needs some fucking and the sissy starts giving a blowjob so that that fat juicy dick will be ready for slamming that sissy's bunghole and showing him who is the boss. The horny sissy bitch gets his gripping transvestite ass royally annihilated and even after that cock has been in his ass he starts sucking his cock for the ultimate humiliation.

Model(s): Lewis, Connor C | Duration: 10min 38sec | Type: SD | Size: 154mb

Model(s): Lewis, Connor C | Site: GaySissies.com | Category: Videos


30.05.2009
Description: It's Lewis and Connor sensing a hard sturdy cock nearby this gay sissy just had to have that meat up his nasty hot ass and his lucky boyfriend agreed. After some passion play, dude was in there pounding that sissyboy's butthole and wearing that sisssy out and as he slammed that cross dresser butt the howls and whines were proof he was seriously being turned into a lusty submissive sissy that should have thought twice before taking on that thick meaty cock.

Model(s): Lewis, Connor C | Number of pics: 36 | Resolution: 1505x1000

Model(s): Lewis, Connor C | Site: GaySissies.com | Category: Pictures


14.05.2009
Description: Two men alone Jack and Donald and one of them is going to get his cross dresser butt busted wide open as soon as they get their horny passions up. The one man goes for haywire headed for the other dude's tight hot sissy butt with his thick meaty cock whipped out and ready. Soon the man's sweet raw bum is totally destroyed and the other man is so happy that hebanged that butt into oblivion.

Model(s): Bobbie A, Lewis | Number of pics: 61 | Resolution: 1504x1000

Model(s): Bobbie A, Lewis | Site: GaySissies.com | Category: Pictures


08.06.2008
Description: This red-haired sissy is way too sexy and bossy. He cannot go on for too long without getting his tight rear thoroughly dicked and filled, so he puts on an expensive office suit with a tight fitting skirt, shiny nylons and high heels - just to show who’s the boss here and get pumped by his employee.

Model(s): Desmond, Lewis | Number of pics: 65 | Resolution: 1504x1000

Model(s): Desmond, Lewis | Site: GaySissies.com | Category: Pictures


25.04.2008
Description: Crossdressing is much fun when a sissy puts on a jolly red wig and hot lace top stockings, his feminine blouse and short skirt add to the splendor. You are in for still more fun when you can see this sissy getting fondled and fucked up his bum with a stiff meaty tool after some proper oral warm-up.

Model(s): Bobbie A, Lewis | Duration: 13min 47sec | Type: SD | Size: 200mb

Model(s): Bobbie A, Lewis | Site: GaySissies.com | Category: Videos


25.02.2008
Description: Am I the cutest sissy in the world? If that mirror could talk it would certainly reply - "sure, you are!" Why, with his long-haired wig, flowered nightie and sheer white stockings he looks like a "Miss Cuteness". So his horny gay friend goes for morning oral-anal exercises right in his blue pajamas.

Model(s): Desmond, Lewis | Number of pics: 72 | Resolution: 1504x1000

Model(s): Desmond, Lewis | 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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