Latest updates featuring Kai Bailey

Sophia Sweet in 'in DP Fantasy'

Sophia Sweet - in DP Fantasy

Dear diary, today I went for a workout, little did I know it would be a harder and hotter one then usual. Basically, two hot guys were having a private training session, I was aching to be a part of! All I want these two studs, Kair Bailey and Coach Cardher, to do is fulfill my most nasty fantasies, use me and shoot a hot batch of cum all over my face! I think I?ll dream that they are both here with me now, and play with myself! OMG dream fantasies do cum true, both of these guys are here with me now? what just happened? OMG there is cum all over my face! Wait, what?

Sully Savage in 'in Chained Hardcore Heat'

Sully Savage - in Chained Hardcore Heat

It's time for another hot hardcore scene! Hey all, Sully Savage here, that's right Kai Bailey, tell me what to do, lead me onto the bed with this chain wrapped around my mother fucking neck! I'll suck your cock till it nearly cums off! I love that big hard fucking cock, deep down my dirty, wet throat! I'll suck it like the freak I am! Fuck my face while you stand up, then I'll suck your cock while you're laying down. Then slap my face and fuck me good and hard! In the end, shoot a massive load of filthy, creamy cum all over my fucking face!


Scenes from other sites featuring Kai Bailey

Janie Blade in 'TS Janie Blade: Gaping, Orgasmic Anal'

Janie Blade - TS Janie Blade: Gaping, Orgasmic Anal

TS temptress Janie Blade flirts in sparkly fishnet lingerie. Adventurous stud Kai Bailey gives her a worshipful blowjob, swirling his tongue around the head of her red-hot she-dick. Janie returns the favor, licking Kai's thick shaft and shoving a finger up her tight asshole. Kai gives her a thorough rim job, and then he stuffs his man-meat inside her pulsing rectum. Janie screams in heat as Kai's cock pummels her sphincter. Janie's butthole gapes! She climbs on top and mounts Kai to indulge in an intense cock ride. Janie masturbates as she bounces on Kai's rod, and her boner spurts a load of girl cum. Janie sucks his cock ass-to-mouth, and she swallows Kai's hot semen.

Erica Cherry in 'TS Erica Cherry: Sex In Her Man's Car'

Erica Cherry - TS Erica Cherry: Sex In Her Man's Car

Blue-eyed, redheaded TS Erica Cherry flaunts her throbbing girl dick in the passenger seat of freaky stud Kai Bailey's car. He jerks her thick dick and wraps his lips around, giving her a worshipful head job. She returns the favor, sucking his veiny boner and then sliding his cock into her hungry asshole. Erica moans and screams, legs shaking, as Kai's meat thrusts inside her tight sphincter. He strokes her she-schlong as he works inside her, bringing her to the edge of orgasm. Erica gives Kai a sloppy, ass-to-mouth blowjob. She enjoys a dripping load of his sticky semen on her chin.

Gracie Jane in 'TS Gracie Jane: Curvy-Ass Anal Ride'

Gracie Jane - TS Gracie Jane: Curvy-Ass Anal Ride

Brassy blonde TS Gracie Jane has big boobs, thick hips and puffy blowjob lips. The pale, tattooed looker sports lush lashes and imposing, gold-sparkling nail art. Heavily inked stud Kai Bailey caresses her tits, spreads her big butt and deepthroats her she-dick, lapping balls too. They French kiss intimately. Gracie goes down on his big cock, gripping the boner at the base and sucking wetly. She services his scrotum. Slobber flows as he fucks her throat. Kai lubes his meat and fucks Gracie's asshole, saying, 'I love the way you grip that cock.' Her tight pink anus gapes. As Gracie takes an anal ride, her big, curvy butt cheeks envelop his meat. Lube oozes from her bunghole. She masturbates and tweaks her nipples as he laps her balls, soon pumping out droplets of jism. Kai enjoys a titty fuck, his erection frottaging her ample cleavage. He ejaculates two loads of cum, which Gracie rubs into her breasts and mouth.

Flowergoth Roze in 'TS Flowergoth Roze: Jacking, Bjs, Anal'

Flowergoth Roze - TS Flowergoth Roze: Jacking, Bjs, Anal

Flowergoth Roze is a tall, trim TS babe that loves driving men crazy. The slim vixen flaunts her fit, oiled body and long legs through a sassy intro. Flowergoth plays with her she-cock and spreads her tight asshole for the camera, soon joining lustful stud Kai Bailey for a hot anal session. Kai rims her bunghole and gives her a wet blowjob, choking on Flowergoth's thick prick throughout. Intense face fucking leads to passionate mutual masturbation. Flowergoth returns the oral favor. Kai bends Flowergoth over for a pounding buttfuck. The filthy sex session features passionate kissing, ass-to-mouth fellatio, and a messy cum facial.

Echo Screams in 'TS Echo Screams Spanked And Reamed'

Echo Screams - TS Echo Screams Spanked And Reamed

Echo Screams is a sassy TS babe that loves showing off her tight body. The blonde hottie's heavy metal look includes tight jean shorts, a puppy collar/choker, and large spacer earrings. Echo teases the camera and then welcomes bold stud Kai Bailey with passionate kisses. She holds their cocks and jerks them off together. Kai kneels to give a sloppy blowjob. Echo moans as Kai rims her asshole, and she drools as she sucks Kai's big cock. Kai spanks her as he porks Echo's tight butthole -- it's a rowdy spectacle! The freaky encounter features intense anal cock riding, ass-to-mouth fellatio and rectal gaping! Kai chokes Echo as she masturbates to climax. When he splashes his hot sperm over her chest, the cute TS collects the cum and swallows it down.

Chanel Noir in 'TS Chanel Noir Seduces Stud for 69'

Chanel Noir - TS Chanel Noir Seduces Stud for 69

Tight TS beauty Chanel Noir lounges seductively in cheetah print lingerie. She licks stud Kai Bailey's big, delicious cock. Hungry Kai gives Chanel a deepthroat blowjob and a rim job! They share 69, covering each other's meat in spit. Kai slides his boner up Chanel's puckering asshole, filling her up with man-meat. Chanel jerks her girl-dick as he fucks her, and her butthole gapes! She sucks his prick ass-to-mouth. Chanel shoots cum on herself! The male-on-trans anal fun climaxes with Chanel swallowing Kai's sperm.

Roxxie Moth in 'TS Roxxie Orally Dominates Male Slave!'

Roxxie Moth - TS Roxxie Orally Dominates Male Slave!

Wild TS Roxxie Moth has a special surprise in store for director Joey Silvera: The Amazonian trans babe arrives at his house with her personal male slave, Kai Bailey, and they're eager to perform a nasty oral show. Kai immediately gives Roxxie a sloppy blowjob, and dominant Roxxie barks orders at him through an intense face fuck. She takes off her sneakers so Kai can worship her perfectly pedicured feet. Roxxie whimpers as Kai lewdly rims her asshole. She jacks off and cums into Kai's hungry mouth. The dominant vixen rewards the slave by jerking his prick to creamy climax.

Jureka Del Mar in 'Anal Buffet 13'

Jureka Del Mar - Anal Buffet 13

Tattooed Asian cutie Jureka Del Mar hangs out in the kitchen, ready to perform raunchy anal shenanigans. The sassy butt babe stuffs oranges, apples, and lemons into her rectum, lewdly farting as her sphincter expels them! The crudeness continues when Jureka gives stud Kai Bailey a messy, saliva-slathered blowjob. Kai power-plows the young girl's asshole to gaping! He yanks his meat from her rectal clutch and fucks her throat ass-to-mouth! A vulgar display of sodomy features rabid bunghole reaming and a messy cum facial.


Micky in 'Trans-Visions 12'

Micky - Trans-Visions 12

White stud Kai Bailey admires young Thai ladyboy Micky as the lithe, tanned T-girl does the dishes. Micky exposes her round boobs; she and Kai kiss on the sofa. Cute Micky worships Kai's raging erection, and he rims her asshole while stroking Micky's little boner. Kai shoves his thick cock up her tight, young ass. He reams the petite T-doll anally, making her butthole gape and her she-dick spurt in orgasm! Finally, Kai cums in Micky's mouth.

Nonny in 'Trans-Visions 12'

Nonny - Trans-Visions 12

In striped stockings, high heels and a tiara, adorable, young Thai ladyboy Nonny plays with her sensitive nipples and pulls her stiff, uncut cock from her lacy panties. The all-natural T-girl stretches her lithe body and licks white stud Kai Bailey's throbbing boner. Nonny blows Kai; he pushes his hard-on deeply inside Nonny's tight, little asshole. She jacks her boner as he reams her rectum, till her cum erupts like lava. Seconds later, Kai ejaculates into Nonny's mouth.

Pony in 'The Trans X-Perience 7'

Pony - The Trans X-Perience 7

Pony is a cute T-girl with luscious tits and an adorable smile. The Asian doll joins stud Kai Bailey for a passionate anal plowing. She delicately slurps his Kai's thick cock and whimpers as Kai penetrates her tight sphincter. Pony pumps her prick as Kai drills her rump. The T-girl sucks dick ass-to-mouth and masturbates to an intense orgasm. After a passionate sodomy session, Kai jerks off and cums into the feminine ladyboy's mouth.

Jonelle Brooks in 'TS Playground 27'

Jonelle Brooks - TS Playground 27

Pale, dark-haired American T-girl Jonelle Brooks' gold lamé outfit shows off her firm tits, tight anus and stiff, raging she-dick. Stroking herself, Jonelle wraps her lips around tattooed stud Kai Bailey's huge cock. She mounts his shaft for an anal ride. Kai pulls his prick from her rectum so Jonelle can suck it ass-to-mouth. The rad dude ravages the TS slut's asshole and then splatters her open mouth with hot splooge.