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Latest updates featuring Maddy O'reilly

Francesca Le in 'Sloppy Compilation - Jay Sin'

Francesca Le - Sloppy Compilation - Jay Sin

Ultimate compendium from director Jay Sin's sloppiest scenes featuring all your favorite pornstars. Watch these babes drool and slobber in one sticky compilation you will never forget.

0:00 - Pretty Sloppy #04 - Kelly, Proxy and Skyler
3:02 - Pretty Sloppy #05 - Mckenzie, Chanel and Jodi
6:12 - Pretty Sloppy #06 - Chastity, Kristina and Proxy
9:17 - Pretty Sloppy #05 - Chastity and Luna
12:28 - Pretty Sloppy #04 - Francesca, Julia, Ice
15:28 - Pretty Sloppy #05 - Vicki, Sarah, Lily
18:40 - Pretty Sloppy #06 - Holly and Adriana
21:43 - Pretty Sloppy #04 - Ellen, Logan  and Kid
25:15 - Pretty Sloppy #06 - Vicki, Maddy and Jillian
28:17 - Pretty Sloppy #06 - Gabi, Adriana and Jenna
31:43 - Pretty Sloppy #04 - Lara and Henessy 
34:18 - Pretty Sloppy #05 - Sandra and Roxy
36:58 - Pretty Sloppy #06 - Diamond and Kelsi
41:04 - Pretty Sloppy #05 - Holly and Sinful 
45:10 - Pretty Sloppy # 06 - Layla and Savannah

Maddy O'Reilly in 'Double Anal Divas'

Maddy O'Reilly - Double Anal Divas

Lovely redhead Maddy O'Reilly poses beside the pool, exposing her soft, natural tits and plump, jiggling booty. This sexy girl craves a nasty backdoor threesome with well-hung studs Mick Blue and Ramon Nomar! She gags giving the men blowjobs; their big cocks fuck Maddy's juicy pussy and thick ass. The studs treat this plush babe to a rude DP. A nasty double-anal penetration stretches her bunghole to the maximum! Ramon and Mick shower Maddy's pretty face with a messy cum facial.

Maddy O'Reilly in 'Oily Anal Big Cock 3'

Maddy O'Reilly - Oily Anal Big Cock 3

Butt-blessed redhead Maddie O'Reilly, tattooed tart Kissa Sins and thickly hung Manuel Ferrara share a passionate, oil-drenched anal threesome. The natural-bodied girls wear net lingerie; Maddie has a 'SLAVE' collar and a butt plug wedged in place. Slathered slick, the trio exchanges French kissing, intense choking and slobber. Manuel fucks both mouths and shaved pussies. As one slut rides his massive, uncut meat, the other sits on his face, licks balls, tongues his bunghole, sucks feet, eats pussy and/or rims the second girl. Amid more oil, the aggressive stud fucks Maddie up the ass, slapping face and tits; Kissa gives an ass-to-mouth blowjob. Manuel drills her to orgasmic frenzy. Soaked in oil and sweat, hair matted, the kneeling ladies trade semen-slurping kisses.

Maddy O'Reilly in 'Rocco and Kelly: Sex Analysts'

Maddy O'Reilly - Rocco and Kelly: Sex Analysts

Legendary Rocco Siffredi and his classic muse, buxom British blonde Kelly Stafford, explore the freaky, psychosexual crosses they bear. A visually striking orgy in a European mansion features Rocco, Kelly and porn rebel James Deen harshly dominating fishnet-clad sluts Maddy O'Reilly and Dahlia Sky. The girls provide slobbery oral worship amid gagging, choking breath play, slapping, spanking, hair pulling and foot sucking. Collared, leashed Maddy rides James' dick as Kelly rims her. The scene starts with Kelly dramatically splayed on a cross; by the end, she has naked Rocco bound to the cross as Dahlia sucks his load into her mouth.

Maddy O'Reilly in 'All Stuffed Up 02'

Maddy O'Reilly - All Stuffed Up 02

Pretty, big-assed Maddy O'Reilly says, 'Nothing's hotter than getting destroyed by two guys at once.' Her slo-mo booty clap invites director Toni Ribas and hung Ramon Nomar. They spank her natural tits, shaved cunt and fleshy cheeks red. Maddy gives a slobbery, double BJ; she shrieks and blushes through straight-to-anal reaming, face slapping, gagging, double vaginal stuffing, double anal plowing and double penetration! She joyfully chokes, gives A2M head, cleans feet orally and eats spit. Ramon fingers her to an orgasmic squirt. Her own juice splashes her face, followed by two thick loads.

Maddy O'Reilly in 'Dredd's Interracial Anal Destruction'

Maddy O'Reilly - Dredd's Interracial Anal Destruction

Adorable, all-natural white beauty Maddy O'Reilly craves interracial thrills -- she loves getting her thick, soft booty fucked by enormous black cocks! Stretching her sphincter with a glass dildo, she eagerly sucks on Dredd's massive meat pole, barely able to fit the head in her mouth. She mounts his monster dick and slides her pussy up and down the throbbing shaft. Dirty Maddy rims the black man's anus. Dredd fills the slut's juicy ass with his giant pole and cums in Maddy's mouth.

Maddy O'Reilly in 'Buttman Focused 11'

Maddy O'Reilly - Buttman Focused 11

John 'Buttman' Stagliano explores the mystery and timeless attraction of a woman's asshole in this epic-length (96 minutes!) series of hot anal fetish clips. Rectal supermodel Casey Calvert and cute Gabriella Paltrova masturbate with vibrating wands, stretching their expressive sphincters with huge toys and speculums. Gabriella employs pussy clamps and pushes the wand into her ass! Jodi Taylor, Savannah Fox, Abella Danger and Maddy O'Reilly get themselves off using various dildos, butt plugs and vibrators.


Casey Calvert in 'Buttman Focused 11'

Casey Calvert - Buttman Focused 11

When girls visit John 'Buttman' Stagliano's studio, they naturally expect lots of anal fun! These insanely hot tease clips showcase 55 minutes of Buttman's favorite asses, and some stunning models that enjoy making their sphincters gape open! Casey Calvert parts her adorable butt cheeks to flaunt her tender anus, Gabriella Paltrova winks her talented asshole, Jodi Taylor displays her outrageously big, beautiful booty, and Savannah Fox, Abella Danger and Maddy O'Reilly all tempt us with perfect rear views.

Maddy O'Reilly in 'Buttman Focused 11'

Maddy O'Reilly - Buttman Focused 11

When girls visit John 'Buttman' Stagliano's studio, they naturally expect lots of anal fun! These insanely hot tease clips showcase 55 minutes of Buttman's favorite asses, and some stunning models that enjoy making their sphincters gape open! Casey Calvert parts her adorable butt cheeks to flaunt her tender anus, Gabriella Paltrova winks her talented asshole, Jodi Taylor displays her outrageously big, beautiful booty, and Savannah Fox, Abella Danger and Maddy O'Reilly all tempt us with perfect rear views.

Maddy O'Reilly in 'Buttman Focused 11'

Maddy O'Reilly - Buttman Focused 11

John 'Buttman' Stagliano gets as close as his camera will allow to photograph the perfect pussies of stunning models. Casey Calvert puts clothespins on her exquisitely shaved cunt. Gabriella Paltrova queefs at will while using labia clamps! Jodi Taylor strokes her sensitive clitoris and shows off her furry snatch. Savannah Fox manipulates her plump, meaty cooch. Abella Danger and Maddy O'Reilly each masturbate their sweet spots in quivering detail.

Abella Danger in 'Buttman Focused 11'

Abella Danger - Buttman Focused 11

In this series of sloppy fetish clips, dirty girls gag on big dildos to create nasty rivers of messy drool. John 'Buttman' Stagliano documents the soaking action as Gabriella Paltrova blows spit bubbles, Savannah Fox bastes her tits in gooey expectorate, Maddy O'Reilly shoves fingers down her throat and slobbers all over her chest (with suction cups on her nipples), and kinky Abella Danger thoroughly ruins her makeup, slapping her own saliva-smeared face.

Maddy O'Reilly in 'Buttman Focused 11'

Maddy O'Reilly - Buttman Focused 11

John 'Buttman' Stagliano shoots video of insatiable young sluts using the finest in sexual technology to make themselves cum! Casey Calvert, Maddy O'Reilly, Jodi Taylor and the spit-slathered Abella Danger each climax with powerful vibrators while getting stuffed by various anal dildos. Gabriella Paltrova queefs in orgasm, fingering her juicy cunt, and redhead Savannah Fox squirts copiously while stretching her anus with a huge glass butt plug followed by a big vibe.

Savannah Fox in 'Buttman Focused 11'

Savannah Fox - Buttman Focused 11

In this series of juicy video clips, John 'Buttman' Stagliano shoots video of teasing temptresses as they squeeze, spread and stroke their sweet, plump pussies. Casey Calvert, Gabriella Paltrova, Savannah Fox, Abella Danger and Maddy O'Reilly wedge their panties between their cunt lips and tug their sensitive labia apart for our perverted perusal. Fans of these young ladies' most holy holes can bow and worship!

Maddy O'Reilly in 'Buttman Focused 11'

Maddy O'Reilly - Buttman Focused 11

Gorgeous young ladies show off their deep-throating skills for kinky director John 'Buttman' Stagliano, using various toys and gag-inducing phalluses. Huge, wall-mounted dildos stretch the throats of Gabriella Paltrova, Savannah Fox, Abella Danger and Maddy O'Reilly, making these orally skilled sluts regurgitate rivers of slimy spit. Adorable, big-assed Jodi Taylor chokes on rubber dick while she buzzes her juicy pussy to orgasm!

Maddy O'Reilly in 'Buttman Focused 11'

Maddy O'Reilly - Buttman Focused 11

John 'Buttman' Stagliano explores the contours and texture of several sets of gorgeous, all-natural tits in this series of teasing video clips. The director pinches and tweaks the sensitive nipples of stunning babes like Casey Calvert, Gabriella Paltrova, Jodi Taylor, Abella Danger and Maddy O'Reilly as they flaunt their sexy boobs for him. Redheaded cutie Savannah Fox gets her jiggling jugs stimulated with a pair of nipple-swelling suction bulbs.


Maddy O'Reilly in 'Buttman Focused 11'

Maddy O'Reilly - Buttman Focused 11

A true connoisseur of feminine beauty, director John 'Buttman' Stagliano trains his camera on a variety of gorgeous young ladies in his home studio. In this epic highlight reel of perversity, model-tier babes like Casey Calvert, Gabriella Paltrova, Jodi Taylor, Savannah Fox, Abella Danger and Maddy O'Reilly sloppily suck and masturbate with big dildos, huge butt plugs, suction cups, clamps and other outrageous sex toys. See all-natural sluts buzz their sensitive pussies with vibes, teasing the director to madness!

Maddy O'Reilly in 'Buttman Focused 11'

Maddy O'Reilly - Buttman Focused 11

In this provocative series of video clips, lucky director John 'Buttman' Stagliano gets to shove his nose into the alluring, thinly clothed butt cracks of a series of gorgeous young ladies. Casey Calvert, Gabriella Paltrova, Jodi Taylor, Savannah Fox, Abella Danger and Maddy O'Reilly sport a variety of sexy clothes, from sheer fishnet hose and tiny thongs to butt-hugging spandex. Casey even sits right on the director's face so he can inhale the delicious scent of her ass.

Maddy O'Reilly in 'Buttman Focused 11'

Maddy O'Reilly - Buttman Focused 11

In this hypnotizing series of video clips, John 'Buttman' Stagliano closely follows beautiful asses swaying from side to side as they strut. Stunning booty teases Casey Calvert, Jodi Taylor, Savannah Fox, Abella Danger and Maddy O'Reilly stride away from the camera, providing perfect views of their gorgeous butts -- clad in fishnet dresses, taut spandex, tiny thongs, leotards or nothing at all! Abella's walking rump is festooned with suction cups, and Casey's bare booty clutches a butt plug.

Maddy O'Reilly in 'Black Snake Oil 3'

Maddy O'Reilly - Black Snake Oil 3

Captivating, all-natural fuck-slut Maddy O'Reilly adorns her light-skinned body with slinky fishnets and classic stripper heels for an interracial anal date. The lusty harlot drools over Mickey Mod's stiff black cock in an intense blow job. Hung Mickey delivers throat choking and spanking; he fingers her cunt to squirting orgasms! He douses her plump booty in oil and plunges his thick prick into her sphincter for a ravaging anal fuck. Lust-addled Maddy babbles foul-mouthed rhetoric, guzzles greasy prick ass-to-mouth and swallows Mickey's cum.

Maddy O'Reilly in 'Squirtqueen'

Maddy O'Reilly - Squirtqueen

All-natural blonde beauty AJ Applegate teases the camera with her big, curvaceous ass and small, perfect boobs. Next, the leggy bombshell dominates young brunette Maddy O'Reilly in a lewd display of lesbian lust. She rips off Maddy's dress and makes her kneel; AJ diddles Maddy's shaved pussy and squirts messy girl cum all over the young slut's face! Maddy submissively laps up the fragrant liquid. The lovely minxes grind their tender cunts together. They share vibrators and dildos, face sitting, girl kissing and female ejaculation!

Maddy O'Reilly in 'Rocco's Intimate Initiations 2'

Maddy O'Reilly - Rocco's Intimate Initiations 2

Strawberry blonde Maddy O'Reilly's fleshy, all-natural body looks enticing in her fishnets-and-heels outfit as she re-connects with stud porn legend Rocco Siffredi. It's their private, very personal backstage reunion before a scene, and Maddy's excited beyond words because her last scene with Rocco was the best of her life. He teases and fingers her into masturbatory reverie. Maddy makes full, intense eye contact with Rocco's POV camera as she worships the gigantic cock she calls 'so perfect.' Her cocksucking, plus intense French kissing and brief fucking, make Maddy's cunt creamy. This backstage honesty leaves them primed to go shoot some porn.

Maddy O'Reilly in 'Anal Avenue Sluts 02'

Maddy O'Reilly - Anal Avenue Sluts 02

Beautiful brunettes Callie Calypso and Maddy O'Reilly demonstrate their love for nasty anal fucking in a three-way with director Mike Adriano. After some lewd ass licking, the girls orally pleasure the director's massive cock and ball sack in a wet, sensuous double blow job. The sluts take turns getting their sphincter stretched, each slurping Mike's meat straight from her girlfriend's gaping hole. Callie climaxes with a vibrator as her rump is reamed; finally, Maddy laps up Mike's splooge and shares it in a tongue kiss.

Dana DeArmond in 'Anal Buffet 12'

Dana DeArmond - Anal Buffet 12

Slender slut Dana DeArmond, adorable Maddy O'Reilly and gorgeous Asian sex bomb London Keyes are spotting one another in the gym. Of course, this workout is all about their round, sexy asses, and worshiping them with fingers and tongues! After a sensuous session of wanton butthole licking and anal probing, the ladies team up on Prince Yahshua and his massive black cock. Yahshua provides intense interracial reaming to their various orifices and splatters their sweet butts with hot semen.


Maddy O'Reilly in 'Up My Booty'

Maddy O'Reilly - Up My Booty

Auburn-haired slut-next-door Maddy O'Reilly poses poolside, showing off oiled natural tits and tugging her bikini bottom between shaved, puffy pussy lips. Inside, she spreads for stud Mark Wood, who spanks and rims her fleshy ass. He expands her butthole with a glass toy and a fat butt plug, which she tastes. (Maddy: 'It smells so good after it's been in there.') Mark's wood then slides straight up her booty with zero resistance. He plows pussy and asshole back-and-forth, choking her, smacking her tits and face hard. Mark pulls Maddy's red pubes as he porks her bunghole and grips her head for an ass-to-mouth face fuck with heavy spit. Orgasmic anal slamming makes her howl, buns flexing, and Maddy's butthole gapes. She swallows Mark's semen.

Maddy O'Reilly in 'Oil And Anal'

Maddy O'Reilly - Oil And Anal

Maddy O'Reilly thickly slathers her body in oil, from auburn hair to smoky eyes to natural tits to fleshy butt. She booty-claps as slick fluid sheets on her ass cheeks and floods her holes. Muscular, bearded Ramon Nomar stuffs three greasy fingers up her ass and feeds her the flavor. His big prick goes straight up her ass, pounding out moans and whines. Ass-to-mouth cocksucking makes Maddy gag. She talks dirty in a cheek-slamming anal ride, Ramon masturbating her clit. With her glistening legs pulled back, he alternates hammering butthole and pussy as Maddy blushes and cums. And she sucks his toes as he sodomizes her. Ramon pulls her oil-saturated hair and slaps her tits as he butt-fucks her. Maddy kneels for a cum facial.

Maddy O'Reilly in 'Buttman Toy Master'

Maddy O'Reilly - Buttman Toy Master

Auburn-haired, brown-eyed cutie Maddy O'Reilly visits John 'Buttman' Stagliano for a sensual exploration of her all-natural body and lustful soul. She shows off her shapely, fleshy butt -- with her dress tugged into her cheeks for a wedgie; twerking in a thong that forms a camel toe; and naked, outdoors. Buttman tests the depth of her crack with his nose. He torments her nipples with clothespins and wicked suction devices, one of which makes her clit throb visibly. Sucking huge dildos, Maddy's drool floods her face and body. A bejeweled metal butt plug expands her anus and Buttman captures cool ass imagery through a Lucite chair. Huge glass butt plugs plus a vibe on her clit give Maddy a howling orgasm; she sucks a plug ass-to-mouth. Soaking wet, she twerks good-bye, naked cheeks clapping.

Vicki Chase in 'Pretty Sloppy 06'

Vicki Chase - Pretty Sloppy 06

Auburn-haired Maddy O'Reilly, Latina beauty Vicki Chase and blonde superslut Jillian Janson are nasty girls in sheer white stockings and lacy lingerie. These sultry lesbians love nothing better than to gag themselves with dildos and drool wads of sloppy spit directly into each other's mouth! Each young lady takes her turn getting her asshole drilled with a fake cock ... as her girlfriends slobber with pleasure and lewdly lick her winking anus!

Maddy O'Reilly in 'Babysit My Ass 5'

Maddy O'Reilly - Babysit My Ass 5

Adorable butt-slut Maddy O'Reilly submits to a bare-assed spanking from director Joey Silvera before joining sultry blonde Carter Cruise and well-hung stud Xander Corvus in a nasty threesome. The girls double-team Xander's huge cock, orally worshiping his balls and bunghole. They take turns anally riding him, then slurping his greasy tool ass-to-mouth. Maddy even gets double-penetrated when Carter straps on a butt-reaming dildo! Using her tongue, Carter helps clean a mess of Xander's hot cum off of Maddy's pretty face.

Ava Addams in 'Rocco's Perfect Slaves 4'

Ava Addams - Rocco's Perfect Slaves 4

Young, cutie Maddy O'Reilly is really annoyed by her older housemate: Busty bombshell Ava Addams is constantly having outrageous sex! Ava enlists her big-dicked pal Rocco Siffredi to loosen up Maddy. Before long, the Euro-stud is cramming his enormous cock down sweet Maddy's throat, and both fishnet-clad sluts are riding Rocco's dick in a nasty anal three-way. After some relentless ass fucking and kinky foot worship, the ladies share a hot load of Italian cum.

Maddy O'Reilly in 'Anal Buffet 10'

Maddy O'Reilly - Anal Buffet 10

Adorable, auburn-haired doll Maddy O'Reilly may look innocent, but this soft, young cutie has a secret lust for huge, hard dicks. When white stud Erik Everhard and older black cocksman Sean Michaels come over, Maddy's in heaven, kneeling to worship their throbbing shafts with her mouth. The all-natural slut rides one boner while sucking the other and enjoys a passionate double penetration. Her plump ass well fucked and gaping, Maddy gets rewarded with two creamy facials.

Maddy O'Reilly in 'Lex Is Up Her Ass'

Maddy O'Reilly - Lex Is Up Her Ass

Auburn-haired Maddy O'Reilly wears a pink fishnet body suit; lush-lipped, freckled brunette Jodi Taylor sports tight, revealing leggings. The girls flirt, massaging their scantily clad, pale, all-natural bodies. Lex teases them with his huge boner hanging from his pants. He tears open the crotch of Jodi's leggings as the girls kiss, and they kneel to share cocksucking duties. As Jodi takes a doggie-style fuck, Maddy spits into her hairy ass crack. Maddy rides the big black cock, her fleshy cheeks bouncing. Lex alternates pounding Ms. O'Reilly's tight backdoor and her red-haired cunt; Jodi slurps Lex's flavored bone, gets her box bored out and eats Maddy's twat. After lots of shared cocksucking, spit play and boning, Lex creams Jodi and Maddy's faces, and they share cum kisses.