Ashley Adams at NaughtyAmerica.com

Maddy May,Tyler Cruise in 'Naughty America' - My Sister's Hot Friend (My Sister's Hot Friend)

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!

Released : May 6th, 2023
Tags : Ball licking, Big Dick, Big Fake Tits, Big Tits, Blow Job, Brunette, Bubble Butt, Caucasian, Deepthroating, Facial, Fake Tits, Hairy bush, Hand Job, Hazel Eyes, High Heels, Long Hair, Masturbation, Medium Ass, My Sister's Hot Friend, Orgasm, Outie Pussy, Piercings, Straight, Tattoos

Ashley Adams at NaughtyAmerica.com
Ashley Adams at NaughtyAmerica.com
Ashley Adams at NaughtyAmerica.com

Pictures from Maddy May,Tyler Cruise in 'Naughty America' My Sister's Hot Friend

Maddy May in 'Naughty America' has revenge sex with her friend's brother (Thumbnail 1)
Maddy May in 'Naughty America' has revenge sex with her friend's brother (Thumbnail 12)
Maddy May in 'Naughty America' has revenge sex with her friend's brother (Thumbnail 24)
Maddy May in 'Naughty America' has revenge sex with her friend's brother (Thumbnail 36)
Maddy May in 'Naughty America' has revenge sex with her friend's brother (Thumbnail 48)
Maddy May in 'Naughty America' has revenge sex with her friend's brother (Thumbnail 60)
Maddy May in 'Naughty America' has revenge sex with her friend's brother (Thumbnail 72)
Maddy May in 'Naughty America' has revenge sex with her friend's brother (Thumbnail 84)
Maddy May in 'Naughty America' has revenge sex with her friend's brother (Thumbnail 96)
Maddy May in 'Naughty America' has revenge sex with her friend's brother (Thumbnail 108)
Maddy May in 'Naughty America' has revenge sex with her friend's brother (Thumbnail 120)
Maddy May in 'Naughty America' has revenge sex with her friend's brother (Thumbnail 132)
Maddy May in 'Naughty America' has revenge sex with her friend's brother (Thumbnail 144)
Maddy May in 'Naughty America' has revenge sex with her friend's brother (Thumbnail 156)
Maddy May in 'Naughty America' has revenge sex with her friend's brother (Thumbnail 167)

More 'Naughty America' scenes from Maddy May,Tyler Cruise

Kimmy Kimm in 'My Sister's Hot Friend'

Kimmy Kimm - My Sister's Hot Friend

Hot perky Asian, Kimmy Kimm, missed her cruise ship spring break trip, and her friend's brother Tyler didn't get to go on his trip with his friends because of bad grades in college. Now that it's only Kimmy and Tyler all by themselves in an empty house, why not have some fun and get it on?!

Rachael Cavalli in 'Wives on Vacation'

Rachael Cavalli - Wives on Vacation

Two horny MILFs, Rachael Cavalli and Reagan Foxx, are on vacation, far away from their husbands on a resort surrounded by spring breakers. Now that it's their last day, they both confess that they secretly had sex with a guy also staying their resort and turns out it was the same guy! The girls want to end their vacation with a hot threesome!

Andi James in 'My Friend's Hot Mom'

Andi James - My Friend's Hot Mom

Andi James is home after a hard day of work and walking in heels all day is really rough. She finds her son's friend Tyler waiting alone. Andi immediately takes advantage of the situation knowing her son won't be back for a good couple of hours. After a foot massage from Tyler, she decides to do some massaging herself, cock massaging that is. Andi couldn't ask for anything better, a hard cock in her wet pussy to relieve all her stress from work.

Shay Sights in 'My Friend's Hot Mom'

Shay Sights - My Friend's Hot Mom

Shay Sights gets an unexpected dick pic from her son's friend Tyler by accident. It was meant for a someone he's trying to hook up with. She tells him that you shouldn't just send a picture of your dick to someone and expect anything to happen. Shay shows him how to set the tone in person, paying attention to que's, and then taking action on ultimately pleasing her.

Rachael Cavalli in 'My Friend's Hot Mom'

Rachael Cavalli - My Friend's Hot Mom

Rachael Cavalli is given the task of taking care of her son's friend, Tyler. He's managed to injure himself and is in need of some tlc. Lucky for him Rachael has some nursing experience. After having Tyler get undressed for a sponge bath, Rachael realizes how her nice big tits and her sensual hand work is making Tyler rock hard and now she can't resist sticking that cock in her wet holes.

Sara Jay in 'My Friend's Hot Mom'

Sara Jay - My Friend's Hot Mom

Sara Jay arrives home after a long day at the gym and is super sore. Luckily her son's friend, Tyler, is there to give her a massage. Sara is so impressed by how good Tyler can make her feel that she decides to have him make her pussy feel good too.

Hot Ass Hollywood in 'is in need of some dick and her son's friend is in the right place, at the right time!'

Hot Ass Hollywood - My Friend's Hot Mom

Sexy MILF, Hot Ass Hollywood, has her son's friend over to do some yard work to earn money for his vacation. He's been out in the sun and heat for a long time now, so Miss Hollywood asks him to come inside and cool off. All of a sudden, the lucky guy has her sucking his cock and her big set of tits sliding up and down his shaft before she shoves it in her wet pussy.

Keely Rose in 'My Sister's Hot Friend'

Keely Rose - My Sister's Hot Friend

Keely Rose is thinking about her future since her friend went away to college. She's getting help moving into a different room by her friend's brother Tyler. One thing leads to another and Keely's big natural tits come out and so does Tyler's big cock.


Bunny Madison in 'My Friend's Hot Mom'

Bunny Madison - My Friend's Hot Mom

Bunny Madison comes home and finds her son's friend Tyler upset because her son got to a girl that he was interested in first. Bunny schools Tyler at how to get a girl and what to do with one once he gets her naked.

Reagan Foxx in 'My First Sex Teacher'

Reagan Foxx - My First Sex Teacher

Reagan Foxx is waiting for Tyler to finish up his exam but he is taking too long and Ms. Foxx catches him reading what it looks to be the answers to the test. She snatches the note and reads it but it turns out to be a letter from a girl that wants to fuck him. Now that Ms. Foxx knows he is a lady's man she wants a piece of that cock for herself.

Casca Akashova in 'Dirty Wives Club'

Casca Akashova - Dirty Wives Club

Casca Akashova doesn't like her daughter's boyfriend, Tyler. Casca's husband isn't too fond of Tyler either, so he gives Casca permission to do whatever it takes to have Tyler dump their daughter. Unfortunately, no matter how hard she tries, she can't convince Tyler to leave her daughter alone. So Casca pulls out the big bribe and promises to fuck Tyler like he's never been fucked before. That's one deal Tyler couldn't say no to -- banging the ultimate MILF.

London River in 'Naughty Office'

London River - Naughty Office

London River was doing a little Cyber Monday shopping at work when her computer gets hit with a virus. The IT guy stops by to take a look and finds out that London's computer went down because she visited a no-no site while trying to get a deal on a vibrator. The IT guy fixes her computer, but she still has no vibrator, so she has the IT guy give her a hand with that by pounding her pussy in her office.

Maddy May in 'hooks up with her friend's big dick dad to ensure he keeps quiet about her shoplifting'

Maddy May - My Daughter's Hot Friend

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.

Jordan Maxx in 'My First Sex Teacher'

Jordan Maxx - My First Sex Teacher

Jordan Maxx found out that one of her students was selling answers to tests. She was a bit upset at first, but after chatting with him she realizes he actually has a lot of drive. So she does what any good teacher would and promises to help him achieve success, but first she helps him achieve his dream of banging the school's hottest teacher.

Desiree Nevada in 'Perfect Fucking Strangers'

Desiree Nevada - Perfect Fucking Strangers

Desiree Nevada notices that the guy working on her jacuzzi and deck is passed out. He can explain it. Seems like some lady walked over and got him drunk. That lady happened to be Desiree's mother and her mother was trying to fuck this dude. Desiree can see why. He's not a bad looking guy, so Desiree decides to ride that dick herself.

Haley Spades in 'loves to masturbate and fuck her friend's brother in the bathroom'

Haley Spades - My Sister's Hot Friend

Haley Spades stayed the night at her friend's house. The next morning, she stumbles upon her friend's dildos and decides to go to town with them in the shower. There is only one bathroom working in the house. Her friend's brother, Tyler, has to use it and walks right in only to find her all horny and ready to for real cock!


Laney Grey in 'fucks her friend's brother on a brand new couch!'

Laney Grey - My Sister's Hot Friend

Laney Grey is getting ready for a house tour but she cant find a vase. Luckily her friend had it and she sent her brother to drop it off, but Laney has always had a crush on her friend's brother. Well Laney is finally single and ready to try out the new couch by fucking her friend's bro on it.

Jane Rogers in 'My Sister's Hot Friend'

Jane Rogers - My Sister's Hot Friend

Jane Rogers is in art class and gets a visit from her friend's brother Tyler. She's been eyeing him for some time now and finally gets her chance to fuck and suck his big cock.

Dee Williams in 'My Friend's Hot Mom'

Dee Williams - My Friend's Hot Mom

Dee Williams heard a lie. Apparently her son's friend, Tyler, has been spreading a rumor that he fucked her. Dee invited Tyler over to confront him about said lie, but she suddenly gets really horny and decides to let her son's friend fuck her and live the lie.


Scenes from other sites featuring Maddy May,Tyler Cruise

Maddy May in 'Is Finally Sexually Satisfied With A DP And Double Vag Penetration'

Maddy May - Is Finally Sexually Satisfied With A DP And Double Vag Penetration

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.

Maddy May in 'Prank On, Wank Off'

Maddy May - Prank On, Wank Off

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 in 'See You Later'

Maddy May - See You Later

Is your girlfriend really out with her friends? Maddy makes up lies so easily, your girl might be doing the same. Would she look as good as Maddy does doing it?

Maddy May in 'Breaking in the New Girl: London River and Maddy May'

Maddy May - Breaking in the New Girl: London River and Maddy May

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 in 'It's Girl's Night Out for Kay Carter, Maddy May, and Megan Maiden and they're craving some hard cock to share'

Kay Carter - It's Girl's Night Out for Kay Carter, Maddy May, and Megan Maiden and they're craving some hard cock to share

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.

Jordan Maxx in 'The Mover'

Jordan Maxx - The Mover

Snooping mover finds Jordan's vibrator in her bedside table. Instead of getting upset, she asks him to use it on her. He gets her pussy ready for his hard cock and blows a load on her face.

Queenie Sateen in 'A New Years Virgin No More - S17:E10'

Queenie Sateen - A New Years Virgin No More - S17:E10

Skylar Snow and Queenie Sateen are getting ready to go to a New Years bash. The girls are nice and flirt with one another, getting dressed together amidst light touches and passionate gazes. Things are nice and hot when Skylar realizes that her roommate's younger brother, Tyler Cruise, is watching them through the open door.The girls comment about how cute Tyler is as they mock his young age. They chat him up and extend their flirting to him as they ask him about his plans for the evening and his resolution for the new year. Both ladies are shocked when they learn that Tyler wants to lose his virginity, but they have an idea of how to make Tyler's night. Queenie tells Tyler that they've just now decided their new year's resolution will be taking his virginity.Pushing Tyler to his back, the ladies tag team his dick. Skylar and Queenie begin by working together, but eventually they move to taking turns as they each pull their big boobies out. Topless, the girls to ahead and each deliver a titty fuck to get Tyler harder than ever. That just makes it nice and easy to move things forward.Queenie takes the D first on her back with Tyler buried between her thighs. Kneeling beside her friend, Skylar makes out with Tyler. Then she gets a turn of her own as she kneels with Tyler banging her in doggy as Queenie kisses Tyler.Putting Tyler on his back, Skylar rides his cock while Queenie mounts Tyler's tongue. He demonstrates that he's not half bad at pussy eating. His reward is to bang Queenie as she lays with her thighs spread wide open.The girls let Tyler finish them off as Queenie stays on her back with Skylar on top of her. The double pussy stack is perfect for Tyler to pick and choose, leaving him free to get his dick wet until he's ready to blow his load. Once he pulls out and nuts on Skylar's back, the girls can play with the cum as they discuss their updated resolutions to keep doing this in the new year.

Maddy May in '- Blacks On Blondes'

Maddy May - Blacks On Blondes

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.


Maddy May in 'Oil-Soaked Anal Gaping!'

Maddy May - Oil-Soaked Anal Gaping!

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.

Anna Claire Clouds in 'Heavy Hitters Get Jaxd Up'

Anna Claire Clouds - Heavy Hitters Get Jaxd Up

I just had to get my boy Jax on Rickysroom, but I also knew that he needed to be paired with some heavy hitters. A team made up of Maddy May and Anna Claire Clouds would be too much for anyone to chew, but I had a feeling Jax was up for the task. And he was. Enjoy!

Maddy May in 'Caution - Slippery When Wet'

Maddy May - Caution - Slippery When Wet

Maddy May in 'Maddy May's Mayhem Sc. 4: Gangbang!'

Maddy May - Maddy May's Mayhem Sc. 4: Gangbang!

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.

Maddy May in 'Maddy May's Mayhem Sc. 3: TS Emma Rose'

Maddy May - Maddy May's Mayhem Sc. 3: TS Emma Rose

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!

Maddy May in 'Maddy May's Mayhem Sc. 2: DVP and DAP!'

Maddy May - Maddy May's Mayhem Sc. 2: DVP and DAP!

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.

Maddy May in 'Maddy May's Mayhem Sc.1: DP and Facial'

Maddy May - Maddy May's Mayhem Sc.1: DP and 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!

Maddy May in 'Big Boobs, Orgasmic Anal!'

Maddy May - Big Boobs, Orgasmic Anal!

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 in 'Tattooed babes, Chantal Danielle, Kitana Montana, and Maddy May visit their favorite artist to persuade him into squeezing them in for a session'

Chantal Danielle - Tattooed babes, Chantal Danielle, Kitana Montana, and Maddy May visit their favorite artist to persuade him into squeezing them in for a session

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.

Lily Larimar in 'Glamping Gloryhole DILF-Hunter Duo'

Lily Larimar - Glamping Gloryhole DILF-Hunter Duo

Lily Larimar & Penelope Kay are staying at their friend Tyler Cruise's place since their college dorm got flooded. But Tyler's strict new stepdad Jovan Jordan won't let them stay in the bedrooms, so they decide to have a indoor glamping event instead. Madness ensues as the girls toy with the guys & hunt their ultimate prey, major DILF Jovan.

Maddy May in 'Biz Up Front, Party In the Back'

Maddy May - Biz Up Front, Party In the Back

Lily Lou, Maddy May and Van Wylde work at a bakery together... which means there's obviously a whole lotta sex going on in there! These sluts and himbos are sneaking around, scissoring, sucking and fucking, and their customers are none the wiser.

Maddy May in 'Seasons Of Sexy'

Maddy May - Seasons Of Sexy

April and May have never been hotter. April Olsen and Maddy May get down and dirty in this sexy lesbian fuckfest.

Nadia White in 'DILFs Get Her Wet'

Nadia White - DILFs Get Her Wet

Coco goes over to study for her college exams with Tyler, her new boyfriend. When Coco sees Tyler's new stepdad & veritable DILF, Alex– she instantly becomes infatuated with him! Coco hunts Alex through the house, exacting her filthiest fantasies upon him while Nadia - Tyler's new stepmom - gives him a few tips on how to handle the ladies.

Maddy May in 'A Hot Day In May'

Maddy May - A Hot Day In May

Maddy May likes to put on a show. The sexy stunner does a sensual strip tease before getting down to business--and dicked down-- by Mick Blue.

Destiny Cruz in 'Dirtier'

Destiny Cruz - Dirtier

Two women compete to show who is dirtier when they realize they're vying for the attention of the same man

Maddy May in 'Oil Slick 5'

Maddy May - Oil Slick 5


Angela White in 'Botched Dinner'

Angela White - Botched Dinner

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!

Maddy May in 'Perky brunette hottie, Maddy May, can't wait to fuck you in VR!'

Maddy May - Perky brunette hottie, Maddy May, can't wait to fuck you in VR!

Maddy May brought you a bottle of oil so you can see her ass and tits nice, wet and shiny. She brings along her favorite toy so you can watch her play with herself. The party isn't over until she makes you cum by sliding her meaty pussy on that big cock of yours.

Eve Marlowe in 'Naughty Party Girls Eve Marlowe, Maddy May, and Quinn Wilde want to celebrate Valentine's Day with a hardcore foursome!'

Eve Marlowe - Naughty Party Girls Eve Marlowe, Maddy May, and Quinn Wilde want to celebrate Valentine's Day with a hardcore foursome!

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!

Osa Lovely in 'House Cleaning Serviced'

Osa Lovely - House Cleaning Serviced

Slovenly Tyler & his lazy girlfriend call a cleaning service to take care of their disgusting loft while they do what they do best – watch TV & play video games. As curvy Osa Lovely dips, bends and crouches to pick up the filthy mess they have left everywhere, Tyler can't help but have his interest piqued by her amazing assets. Boldly, he makes offers to & moves on Osa when his girlfriend naps. Osa is a little shocked at first, but is fairly impressed with this slacker's cock, so she decides to have a little fun herself; on their dollar!

Jezabel Vessir in 'Angela's House Of Hedonism Part 2'

Jezabel Vessir - Angela's House Of Hedonism Part 2

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.

Maddy May in 'Naughty Wife Wets her Shirt'

Maddy May - Naughty Wife Wets her Shirt

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.

Maddy May in 'Anal and Facial Star Quality!'

Maddy May - Anal and Facial Star Quality!

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!

Maddy May in 'That's My Seat!'

Maddy May - That's My Seat!

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.


Maddy May in 'BJ, Rim Job, Orgasmic Fuck'

Maddy May - BJ, Rim Job, Orgasmic Fuck

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.

Alexis Fawx in 'Femme Falls For The Fawx'

Alexis Fawx - Femme Falls For The Fawx

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...

Kuleana in 'Blanket Bastion: Part 1'

Kuleana - Blanket Bastion: Part 1

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.

Maddy May in 'Country Girl Loves Anal Fun'

Maddy May - Country Girl Loves Anal Fun

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 in 'May Day'

Maddy May - May Day

Is this a fever dream, or is Maddy for real? This brunette's luscious curves and sexy attitude will have you burning up, and when she plays with her toys you just might break out in a sweat.

Maddy May in 'Manuel Opens Their Asses 8'

Maddy May - Manuel Opens Their Asses 8

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...

Richard Mann in 'Mom's Not Home'

Richard Mann - Mom's Not Home

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.

Jenna Fireworks in 'Jenna Fireworks, Kayley Gunner, and Maddy May arrive early to the Memorial Day party for a pre-game fuck fest'

Jenna Fireworks - Jenna Fireworks, Kayley Gunner, and Maddy May arrive early to the Memorial Day party for a pre-game fuck fest

Three sexy babes Jenna Fireworks, Kayley Gunner, and Maddy May get invited early to the Memorial Day party, for a good reason though. The host likes to invite his favorite girls early so that they can all have a foursome fuck fest before the actual party starts!


Maddy May in 'Orgasmic Anal, Gaping and A2M'

Maddy May - Orgasmic Anal, Gaping and A2M

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.

Maddy May in 'May I have a giant black cock'

Maddy May - May I have a giant black cock

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...

Kylie Rocket in 'Vacationing college babes, Kylie Rocket, Maddy May, and Maya Woulfe share the big cock of a local boy they just met'

Kylie Rocket - Vacationing college babes, Kylie Rocket, Maddy May, and Maya Woulfe share the big cock of a local boy they just met

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!

Kayley Gunner in 'Find out why these sexy friends, Maddy May, Madelyn Monroe, and Kayley Gunner, were given a huge discount at the infamous Dressing Room'

Kayley Gunner - Find out why these sexy friends, Maddy May, Madelyn Monroe, and Kayley Gunner, were given a huge discount at the infamous Dressing Room

Maddy May takes her friends, Madelyn Monroe and Kayley Gunner, to her favorite lingerie store. They try on various lingerie pieces and and invite the salesman in for his opinion... and his hard cock!

Maddy May in 'Maddy May's Messy Day'

Maddy May - Maddy May's Messy Day

With her big tits squeezed into a little leather top and her neck adorned with chains, Maddy May is a smoke show. This sultry sex fiend makes a mess of her makeup when she goes hard on Jason Moody's impressive member.