Maddy May has a reputation for being unafraid to push the boundaries when it comes to being a naughty slut. She is known for being very adventurous with her pussy and her asshole. This latest sexual adventure takes her to getting double penetration. She was not fully sexually satisfied with double penetration. She decided to take it to the next level with two dicks in her pussy at the same time. Maddy May doing double vag has sexually satisfied her for this sexual adventure.
Beauteous Maddy May gets charitable with her holes in this scene from 'Manuel Opens Their Asses 8'. The Bambi-like May, crushes it during the tease. Barely covered in a neon yellow spandex kit with black trim. Maddy makes her unshaved twat extra noticeable by sandwiching it between her fingers. She does some additional strutting then finds herself on a large white leather sofa built for fuck sessions... Manuel appears and begins sucking on her pierced nipples. Miss May crams her bulbous ass in his face and he munches on her backside. Maddy does a little oral of her own, spitting and slurping on Ferrara's dick. Manuel begins fucking May prone, then he folds her legs to the side producing a stellar view of Maddy's mentionables. Manuel gets on his back and May adds some sleaze to the scene by playing his trombone to the tune of 'tossed salad'... Now that things have dirtied up, Ferrara plants his meat in May's asshole. The sexy stalwart says 'That's your fucking asshole' and weaves some serious slobber. Manuel inserts his fingers into Maddy's pussy and churns until she squirts. This makes Maddy want more Manuel as she says 'I want you to fuck me'. Ferrara does, then Maddy delves so Manuel can distribute a huge load to her face and doe-eyes. May even puts on a little cum-bubble show to drive the point home...
When first observing Maddy May, there's a seed of doubt that she can physically handle the 'DICK of DREDD'. Low slung and hazel-eyed, during the tease you start to believe, she may indeed be able to weather the storm. Primped in black leather strapped lingerie with zebra print, Maddy bends. It's at this moment we see her full potential. For such a diminutive gal, her ass pops at first flex. She has a huge ornamental tattoo that runs down her fleshy thigh, complimenting her pierced nipples. Maddy begins flossing her pussy with her panties, while proclaiming she 'feels like taking a big fucking dick'. Dredd appears and makes her eyes bulge once she sees what she's asking for. Kudos to Miss May for trying, but she is so small she must two-hand Dredd's barrel-like member while fitting as much as she can in her mouth. Maddy finally yelps 'Oh my God! You have such a big dick!' And D-man compliments her on ball sucking... They begin fucking on a red love seat and May decides to straddle in reverse cowgirl. She ends up standing over Dredd while sliding up and down the mondo meat missile. Maddy moves into doggie and Dredd begins to stuff her twat. The visual is almost comical at first. You don't think it's possible, yet Maddy's pretty pussy opens and Miss May has to let out a disbelieving 'Oh Fuck' during the long strokes. Prone on her back Dredd continues with his mission. Maddy gets to her knees and sucks on the timber until Dredd is asking himself his own name while she feeds on his deposit.What a day for Maddy May...
Maddy May stops by her friend's place but she isn't home so she asks her friend's brother, Tyler, if she can go to her sister's bedroom and wait for her. Still, there is something off, and Tyler notices it. He asks Maddy what is going on and it turns out her boyfriend is gone to college and believes he is cheating on her, so she wants to get back at him and fucks Tyler's. He definitely doesn't mind getting some pussy so easily!
Maddy & her bestie Carlita are putting on a livestreaming makeup tutorial when Maddy's annoying new stepbrother David decides it's a fine time to prank them. David sharks the girls repeatedly – but as they're livestream blows up in response, they figure Maddy's stepbro is onto something. The next time David pranks the sexy duo, they trap him and use his cock to put on a perverse puppet show for their fawning audience. David loves it as they handle & manipulate his cock puppet to their liking. Eventually, the girls' figure there are better things to do with David's big dick and put on a wild threesome for their excited fans!
Maddy May is tied with a chest harness. Her hands are behind her back, ankles spreadwide and vulnerable. London spits on her face and rubs it all over Maddy?s tits and playswith her bratty sub?s wet cunt. Then Maddy is bent over and ass fucked with a strap-on bydominant London with plenty of face fucking ass-to-mouth to get more spit as slippery lube. London sits onMaddy?s face making her sub lick her holes and open her Dom?s ass with a dildo. London getsgaped doggy style with a big glass toy while Maddy spits in London?s asshole.
Kay Carter, Maddy May, & Megan Maiden are having girls night and the time has flown by. They didn't realize "last call" was announced and missed their chance for refills. The girls hit up the bar tender but he's not about to lose his license for them. To persuade him, the girls are willing to lock the door and have some fun around the bar, filling their wet thirsty pussies with his big hard cock.
Maddy has been alone for four months now since her husband went on deployment. It will be another six months till he is home and this girl is hankering for some cock. So when she finds out an old friend of theirs is in town she immediately invites him over for a visit. Little does Jax know this girl has nothing but a booty call on her mind. Her asshole needs a good fucking as nothing makes this girl cum like an anal orgasm. It's the rush that gets her tweenie shaking and her spokewheel spinning. At first Jax is not too into this having sex with a married woman thing but soon realizes if he does not do it somebody else will. A patriot if nothing else Jax takes care of his buddy's horny wife by pulling out his monstrous ass blaster of a cock and watching in awe as Maddy slobs all over it. This girl is plum needing some serious dicking. Jax quickly maneuvers his veined and swollen boner into her dripping cunt and proceeds to work up the juices. Maddy's sphincter is starting to twitch in anticipation as Jax aims the head of his man root at her waiting spokewheel and pushes through balls deep into a tight vacuum of love. It's an anal fuckfest as Maddy is shaking and squirming with orgasm after orgasm.
Wearing strappy yellow lingerie and a studded choker collar, busty brunette Maddy May exposes her pierced, pink nipples. She spreads her bubbly ass cheeks and reveals the thick pink butt plug lodged in her rectum. Top stud Rob Piper presents his big Black cock, and he douses Maddy's ass in slippery oil. He plunges his boner deep inside her slippery sphincter, and Maddy screams in orgasmic delight. Rob licks Maddy's pink clit, bringing her to a spasming climax. She masturbates as he reams her asshole relentlessly! Rob switches holes, fucking Maddy's juicy cunt. Her eyes roll back in her head as he strokes in her sweet pussy. He shoots oil inside her butthole! Maddy climbs on top to enjoy an intense anal cock ride. Lube-soaked sodomy includes expansive rectal gaping and an ass-to-mouth blowjob. Rob shoots a creamy load of semen onto Maddy's toned tummy.
From the balcony of a luxury home, hot Maddy May teases seductively in lacy fishnet stockings, bikini underwear and high heels. Inside the mansion, she takes on five ferocious fuckers in her first gangbang! Maddy reveals the clear butt plug in her anus. She sucks John Strong's hard dick. Alex Mack fucks her cunt from behind. The brunette vixen takes a bouncy buttfuck on the staircase, Codey Steele's big cock porking her asshole. Porn pros Mick Blue and Seth Gamble pummel her holes in a nasty double-penetration! The dirty girl blows Seth's prick ass-to-mouth. Hard dicks cram all three of her orifices at once, rendering her delightfully airtight! Maddy treats Codey and Mick to blowjobs while Alex slams her snatch and Seth provides anal railing. John bangs her fuzzy twat. Guys trade her holes like they're playing musical chairs. Maddy drops to her knees to orally service the quintet, draining dicks and wearing a spunky cum facial lathering.
In a tree-lined meadow, hot hippie Maddy May frolics in a beaded skirt and tiny top. Tall, blonde TS temptress Emma Rose joins Maddy, who experiences her first trans scene! The ladies make out playfully in the sunbaked, Eden-like setting. They gently kiss and worship each other's tits. The transsexual babe removes Maddy's panties to eat her pussy. Maddy gives a deepthroat blowjob, skillfully swallowing Emma's boner. Next, Maddy's glass dildo pries open Emma's butthole. Emma slides her she-cock into Maddy's twat, and they share an outdoor fuck. As she slams Maddy, Emma tastes the cis-girl's taut slit. Maddy rims Emma, and she stuffs a toy inside the T-girl's sphincter. Emma tongues Maddy's bunghole and then delivers an anal reaming! Maddy blows she-meat ass-to-mouth! The feral fucking climaxes as Emma cums inside Maddy's pussy. When the creampie filling oozes from Maddy's snatch, Emma laps it up! They share a sloppy semen kiss. Free love, Baby!
Overlooking a nighttime cityscape, beautiful Maddy May stuns in a glamorous, sequined evening dress. The breathtaking brunette teases lustily for the camera, showing off her delicate, round butt cheeks and baring her ample tits. Alpha males Seth Gamble and Mick Blue share the petite vixen's sumptuous body. The sharply dressed men offer their big cocks to Maddy for a blowjob. Maddy strips down to her birthday suit and takes Mick's prick in her twat, riding while she sucks Seth's curved rod. Seth poles her pussy doggie-style as she slops on Mick's meat. In spoon position, Mick fucks her asshole. Seth reams her rectum from behind. Both boners pack Maddy at once in a 'full-filling' double-penetration! Mick and Seth simultaneously stuff her twat -- it's Maddy's first double-vaginal drilling! Next, Maddy experiences her first double-anal cramming! She worships dick ass-to-mouth. Seth and Mick glaze her with a sloppy cum facial.
Cutie-pie Maddy May roller skates along the sidewalk. The dazzling doll rocks hot pants and bikini top, retro headphones and mirrored shades, like a disco babe straight from the 1970s! She pops out her round boobs and lovingly plays with her pierced nipples. In a warehouse, heavily hung porn studs Isiah Maxwell and Jax Slayher shove their big Black cocks in her face, and they receive dueling blowjobs. The guys spit-roast Maddy -- she takes Isiah doggie-style in her cunt and Jax in her mouth. Jax and Isiah trade off dicking her holes while she still wears her shiny platinum skates! Isiah rails her asshole while she sucks Jax's joint. When Jax provides an energetic anal reaming, Maddy sucks Isiah's meat ass-to-mouth. The dudes deliver double penetration, one prick nailing her twat as the other rails her butthole! It's Maddy's first BBC DP! The threesome climaxes as Jax and Isiah cream her chin, giving her a cum facial goatee!
Beautiful, impressively tattooed brunette Maddy May peels shiny lingerie from her big tits, showing off silver nipple piercings. She bends over and unveils the butt plug lodged deeply in her sphincter. Maddy pulls it out as Mick Blue showers her in oil. He slides his big cock inside her butthole from behind, sodomizing her relentlessly as drool dribbles down Maddy's chin. She sucks his dick ass-to-mouth, stroking his shaft enthusiastically. Spit covers her boobs as she climbs on top of Mick's pulsing pole and impales her pussy for a deep dick ride. Mick pounds her cunt and then switches holes, shoving his dick back up her tight asshole. Maddy has a frenzied anal orgasm! She rubs Mick's balls and gives him a worshipful rim job. She twerks on his meaty rod. Maddy's butthole gapes as she masturbates! The rectal recreation climaxes with Maddy swallowing a mouthful of Mick's hot semen.
Chantal Danielle, Kitana Montana, and Maddy May take a trip and visit their favorite tattoo artist to get some work done. Unfortunately, he's booked for months. The girls aren't leaving with out getting tattooed though. They bust out their tits and rub up on his cock persuading him to squeeze them in for a session. He can't help but give in. He'll squeeze them in between other clients as long as he can squeeze their tits and ass and they give some wet pussy while they're at it.
Adorable young couple Maddy May and Anthony Pierce have invited their neighbors over for dinner. Angela White and Keiran Lee are a smoking hot couple and, as soon as they arrive, they only have one thing on their minds. Spoiler: It's not dinner! Soon, busty Angela is deepthroating Anthony in the kitchen, right under Maddy and Keiran's noses. When petite Maddy finally catches them in the kitchen, she puts her jealousy aside and decides to join in the fun. Add Keiran to the mix, and this dinner party has just turned into a girlfriend-swapping party for perverts!
Sexy naughty girls, Eve Marlowe, Maddy May, and Quinn Wilde, enjoy a great Valentine's Day party at the club and everyone had a blast but now it's time to take the party to the hotel in THE luxurious Party Bus where things start to get kinky and wild. They want to see if you can handle 3 babes at the same time in bed for an unforgettable foursome!
The second part of swinger miniseries starts as the evening festivities finally get started with an all-girl threesome of guests. Angela hands off an empty bottle to party girls Maddy May, Jezabel Vessir and Nika Venom and it doesn't take too long before the trio starts playing a raunchy game of spin the bottle. The party is such a blast that they don't think twice before showing off their tits for some nipple worship. Aroused and in dire need of some intimacy, two of them sneak off in a quiet place for 7 minutes in heaven before the third girl finds them and partake in the steamy exchange . They will never forget the heavenly lesbian threesome that ensues.
The lusty Maddy May and lover, Dwayne Foxxx, are having fun with a vibrator in her living room when her husband comes back from work. Dwayne hides and Maddy quickly pulls her panties back up, pretending she was doing nothing. Mischievous Dwayne kept the vibrator's remote control and plans to tease Maddy while she's in front of her husband. After stimulated Maddy jerks and spills the glass all over herself, her husband starts suspecting something's wrong. It doesn't take too long before he realizes that her wife is a cheating liar. Right after the upset husband storms out, Dwayne can't help but undress the horned up Maddy and provide her with the pounding she deserves.
Glamorous brunette Maddy May has Hollywood-level looks. The petite beauty teases poolside in heels and fishnet stockings. She gives a glimpse of the fat cunt lips hidden behind her panties. Indoors, she frigs her snatch, making it wet for porn stud Seth Gamble. Maddy's sweet, young mouth takes his long dick in a blowjob. She pulls her ankles back, spreading her gash as Seth slides his pole inside. He pounds her hairy slit as the horny lass coos. Maddy mounts him, grinding her pussy on his tool as they fuck face-to-face. Alpha male Seth rams Maddy's asshole in multiple positions -- standing, doggie-style, spoon. He delivers an awe-inspiring anal pile-driving! Seth strips off her fishnets and twists them in her mouth as he buttfucks her from behind. The raucous carnality climaxes as Seth unloads a full sack, sending ribbons of jizz across her comely face! The young starlet is now ready for her cum facial close-up!
Mazee has just moved into a great new apartment with a couple of hot girls! The only problem? One of those hot girls, Maddy May is very particular about where her roommates are allowed to sit, and Mazee keeps running afoul of her seating chart. When Maddy catches Mazee in her seat one time too many, she snaps and decides that the only solution is to sit on Mazee's big dick instead.
Instead of calling her actual dad to bail her out of the county jail for shoplifting, Maddy May gets the help of her friend's dad. He reluctantly helps but is pissed and threatens to tell her dad - whom also happens to be his best friend. Maddy placates Brad by giving up her wet pussy and mouth! Besides, she's seen his dick once and ever since, couldn't stop thinking about how it would feel inside her. Brad is married man but it doesn't stop him from having some tight college pussy.
Busty, tattooed brunette Maddy May reveals her pierced nipples and plump ass in a plush hotel room. Pro stud Mick Blue shoots personal, POV-style footage. Maddy oils up her butthole, and Mick teases her clit with his big cock. He slides his meaty boner inside her cunt, and her eyes roll back in her head. Pretty Maddy wraps both hands around his uncircumcised dick and gives him a blowjob, drooling as she sucks. The dirty girl slurps his balls and gives him a worshipful rim job! She climbs on top and indulges in an orgasmic cock ride, and Mick douses her ass in oil. She masturbates while he plows her twat, and Maddy swallows a dripping load of jizz.
Petite Maddy May is having a bit of car trouble, and she knows just the place to get herself fixed up. She pulls up to the helpful Alexis Fawx's place - with overalls barely able to contain this fixer's curves - to take a look under the hood. Alexis looks around and feels like maybe a bit more than the engine needs some attention and she starts to subtle brush against Maddy, drop some flirtatious comments, and eventually make the move to taste and feel what's underneath her pretty little sundress! The sapphic duo fawns, fingers, and fucks around the garage until curious partner Van Wylde arrives to check in...
Sexy brunettes Maddy May and Kuleana are both present at the illustrious annual Blanket Bastion event (hosted by the Pillow King, Michael Vegas). The goal of the event is to find the King's scepter, in exchange for getting drilled by his big dick... an opportunity both girls want. Kuleana distracts Maddy by making out with her and sucking her tits, then finds the scepter. This leads to tension between the girls, which of course leads to a hot lesbian fuck, complete with lots of pussy eating and scissoring. After totally wearing Maddy out, Kuleana retrieves the scepter and starts her journey towards the Pillow King.
Nominated - Best Anal Sex Scene, AVN 2022
Under the sun, Maddy May teases in fishnets, heels and a latex bikini, showing tiny waist, awesome ass, and big boobs with huge, pierced nipples. The young beauty sports impressive tattoos, like the big lion on her hip. Pro stud Mick Blue interviews the first-year porn performer: A country girl from Arkansas, she's loved anal sex ever since her first 'assgasm.' Mick's POV camera captures Maddy's eye contact as she gives a slobbering blowjob. They kiss during a standing, face-to-face fuck. Mick rims her butthole and then stuffs his big cock up her greased sphincter. Maddy gasps and grunts through a serious buttfuck. She sucks dick ass-to-mouth; laps and sucks balls; and looks cutely into the camera as she eats ass. Her gorgeously shaped cheeks glisten as they caress Mick's meat. Maddy's butthole gapes. More anal fun makes her squeal in bliss. She kneels for a messy cum facial.
Maddy May was having a hard time concentrating on her homework. All because she was way to horny to pay attention. What she wasn't aware of is that her moaning was distracting her step dad who was trying to watch the game. After some time of trying to get her homework done, she talked to her step dad about her little problem. She begged him to fuck her so she could finally go back to her homework and focus. Not only did she want him to fuck her, she wanted it in the ass too. Her step dad, Richard Mann, was hesitant at first, but eventually he agreed. He started by stretching her tight little pussy. From there, he shoved his huge cock deep inside her tight asshole. Making her cum several times before her delivered a huge load all over her face.
Wearing high stilettos, tattooed cutie Maddy May peels pink panties off of her plump ass. She masturbates and plucks a rose-shaped butt plug from her hungry asshole. Pro stud Mark Wood shoves his big cock up her rear, making her gasp in heat. When she gives him an ass-to-mouth blowjob, he plunges his cock down her throat. Maddy bounces on Mark's meat and buzzes her clit with a vibe. Her pink sphincter gapes, and she experiences a screaming anal orgasm! The deep buttfucking climaxes with Maddy swallowing a creamy load of cum.
Petite cuties, Kylie Rocket, Maddy May, and Maya Woulfe thought there visit to L.A. was going to be chill with a beautiful rental unit and nice weather, but so far, its been lackluster. Luckily, they just met a hot stud at the bar the other night and decide to have him come over and brighten their day with his big hard cock!
