Latest updates featuring Ryan Madison

Roberta Gemma - The Wife and Boss

Roberta Gemma - The Wife and Boss

29th June - Roberta Gemma is a stunning MILF with big, natural, amazing tits. A bath is a perfect way to start the day before heading to her home office. She becomes distracted by porn, pleasuring herself before calling Ryan over to give her what she really needs. Ryan treats those big boobs and MILF pussy just right before unloading all over those tits. ...Read More
Marilyn Mansion - Static

Marilyn Mansion - Static

22nd June - Marilyn Mansion is back! In an epic hour and a half long fuckfest, you won't forget any time soon! Ryan captures the action in his trademark way as she swallows his cock and wraps her big naturals around his shaft. After pounding that young pussy mercilessly for over an hour he unloads a massive creampie deep inside her! ...Read More
Nina Skye - Bad Teacher

Nina Skye - Bad Teacher

8th June - Grade school teacher Nina should be spending her evening going over her students' papers. When Ryan calls her to come over to hang out by the pool and fuck, this cock hungry young teacher wastes no time! After swallowing his cock down her throat, Ryan pounds that fresh pussy by the pool, finally filling her cunt up with jizz! ...Read More

River Fox - Delivery Girl

River Fox - Delivery Girl

1st June - River started camming to make some extra money when she's not at her regular job as a delivery girl. She tells her viewers where she works and maybe they'd get lucky and have her deliver it. Never one to turn down some teen pussy, Ryan places an order for some juicy teen ass! He leaves a huge load in her pussy for the tip! ...Read More
Kali Roses - Manic Part 2

Kali Roses - Manic Part 2

9th March - The ups and downs come hard and fast for Kali. Transforming from crippling self-doubt to an exhibitionist nymphomaniac in a few hours. With Ryan's help, she works out her problems on his cock. Leaving her worry-free and full of jizz after a serious hardcore fucking. ...Read More
Moka Mora - More Moka

Moka Mora - More Moka

2nd March - Moka Mora has a banging body that she likes to keep in shape with her favorite pastimes. Hula hooping and fucking! She's got the ass and skills to prove it! With camera in hand, Ryan finds out exactly how good she is as he pounds her cunt and fills it with a huge load of jizz! ...Read More
Ivy Lebelle - The MatchMaker Part 4

Ivy Lebelle - The MatchMaker Part 4

19th February - With a manhunt underway for 'the matchmaker killer' and his female accomplice, an escape plan is needed. With James somehow surviving the gas, a scapegoat is made. Matched up with someone just as insane and homicidal, Ivy, they should tear each other apart and take the fall. ...Read More
Kendra Spade - Up My Ass!

Kendra Spade - Up My Ass!

16th February - Kendra loves to tease, flashing her perky tits and bubble butt in the parking lot and the hotel's hallway before they even get to the room. Once inside though, she puts her mouth to work on Ryan's shaft, making sure it's properly lubed up for her tight asshole! Ryan goes balls deep before unleashing a load all over her face and a second on her body! ...Read More
Vanessa Sky - SS Nurses 1

Vanessa Sky - SS Nurses 1

2nd February - Vanessa works hard all day and night as a nurse, but as soon as her shift ends, it's time to take care of her own needs. This normal looking girl hides dark desires that only Ryan can fulfill. Tied up and fucked hard in all of her holes, he leaves her full with cum and happy. ...Read More

Victoria June - Addicted

Victoria June - Addicted

19th January - Victoria just can't stop touching her pussy. When she wakes up, time to masturbate! When she takes a shower, time to masturbate! Getting a ride to the grocery store? Time to masturbate! Laying out in the sun, oiling up her huge tits? You guessed it! What she really needs is a hard cock pounding her holes and filling her with cum! ...Read More
Maya Morena - Extreme Sale

Maya Morena - Extreme Sale

12th January - Maya will do anything to sell this house that's been on the market for far too long. Luckily the Madison's are looking, and Ryan likes what he sees! She's hesitant at first but once she sees the size of Ryan's 'down payment' she's eager to please and close this deal! ...Read More
Riley Star - Double Trouble

Riley Star - Double Trouble

10th January - 300 EPISODES! To celebrate Ryan brought back Hannah Hays and she brought her friend Riley to help her out! These tiny teens get to work on Ryan's member, offering up their little pussies for him to fill with jizz. Hannah gets a big load deep inside her pussy, then licks up the second cumshot from Riley's body! ...Read More
Vienna Rose - Neghbor's Daughter 3

Vienna Rose - Neghbor's Daughter 3

13th December - People with cute, young daughters keep moving in next to the Madison's and Ryan couldn't be happier. Lord help them if he finds them in his yard. Vienna gets tied up and cuffed to an office chair, pleasuring herself with Kelly's vibrator as she sucks Mr. Madison's cock. With her legs up in the air Ryan pounds her young pussy until she's begging to be filled with cum. ...Read More
Ariana Aimes - Not For Sale 4

Ariana Aimes - Not For Sale 4

7th December - Agents are circling in on Ryan's accomplices, but they need to catch him in the act. Luckily The Madam has a new girl that will fulfill one of his fetishes perfectly. Ariana's tits are swollen with fresh milk and Mr. Madison just can't resist. This time it won't just be Ryan's cameras catching all of the action. ...Read More
Brooke Haze - Not for Sale 3

Brooke Haze - Not for Sale 3

1st December - Why go anywhere else when you know exactly where to find the perfect cum hungry teens? Brooke Haze is on the menu this week and Ryan brings his cameras to capture her begging for his hot jizz deep inside her eager young pussy! ...Read More

Nia Nacci - Make 'Em Sweat 14

Nia Nacci - Make 'Em Sweat 14

24th November - Nia is staying with the Madisons for a bit and was taking advantage of their gym room to get in her morning workout. Ryan decides to help her work up a sweat. They use the gym equipment in ways that were never intended before she begs for him to cum inside her multiple times! ...Read More
Amilia Onyx - Manic

Amilia Onyx - Manic

16th November - Amilia has been depressed for a while. Ryan has tried everything to help her, but she just hasn't responded to anything. Maybe all she needs is a good, proper fucking? She immediately cheers up once he whips his dick out and puts it in her mouth! As she sucks down that Vitamin D, she knows that what will really help is a hot load of cum inside her pussy. ...Read More
Alyce Anderson - Take the Condom Off 9

Alyce Anderson - Take the Condom Off 9

9th November - College loans aren't going to pay themselves, so Alyce takes her future, and strangers hard cocks, into her own hands to pay the bills. Condoms are necessary in this line of work, but one long time customer talks her into taking it off. Once it comes off, her inner slut comes out and she's begging for Ryan's cum deep inside her young pussy. ...Read More
Ella Knox - Neighbors Daughter 2

Ella Knox - Neighbors Daughter 2

6th November - Ella brings her big natural tits over to the Madisons to tease Ryan with a little wet t-shirt show. He takes the bait, and his cock is pumping in between those big boobs in no time! It's not long before she's riding his dick and begging for a huge load deep inside her pussy! ...Read More
Khloe Kapri - Devil's Creampie

Khloe Kapri - Devil's Creampie

17th October - Khloe has only ever wanted one thing, a baby of her own to take care of. Ryan, only wants to cum deep inside tight teen pussy. Luckily for both of them, the arrangement can be made for the right price. ...Read More
Amia Miley - Make 'Em Sweat 13

Amia Miley - Make 'Em Sweat 13

9th October - Amia Miley returns, 8 years after her first appearance on Pornfidelity! And WOW has she grown up! With a brand new killer body and a lot more experience, she works Ryan's cock to the limit. You won't last long watching her perfect curves go to town on this dick until Ryan fills her perfect pussy with a huge load! ...Read More

Hannah Hays - The Neighbor's Daughter

Hannah Hays - The Neighbor's Daughter

21st September - When Hannah's family moved in next door, it didn't take long for her to catch Mr. Madison's attention. With her ass hanging out of her tiny jean shorts, he knew getting that young pussy on his cock would be easy. As soon as she got comfortable at the Madison's, his dick was in her mouth and a load was placed deep in her teen cunt. ...Read More
Kimber Woods - 2RUFF4HER

Kimber Woods - 2RUFF4HER

14th September - Kimber's a sexy little piece of ass who comes over to Ryan's house for some fun and games. Ryan likes to push Kimber's limits but sometimes she just can't take it. She runs off and tells everyone how RUFF he is. Kimber will remember Ryan for a lot time to come... ...Read More
Sarah Banks - Beautiful Blessed

Sarah Banks - Beautiful Blessed

7th September - You'll be hypnotized watching her huge bubble-butt bouncing on Ryan's cock. With an ass like that it would be a waste not to fill up that tight hole with white dick and Ryan does not disappoint. He pounds her hard and fills her pussy with his white cream. ...Read More
Hime Marie - Not for Sale 2

Hime Marie - Not for Sale 2

29th August - Two tight teens are better than one! When Ryan was offered a steal on these sisters he couldn't turn it down. You've already seen Kenzie, now it's time to see Hime's skills on his cock. This petite babe can take a pounding and begs to be filled with a huge load of fresh cream. ...Read More
Kenzie Reeves - Not For Sale

Kenzie Reeves - Not For Sale

18th August - Needing to find some fresh talent, Ryan goes to some unsavory sources. She's a mess when Ryan picks her up, but she cleans up nicely. Rescue wouldn't be the exact right word to use, but Kenzie's life is about to get a whole lot easier, as long she keeps that pussy coming. ...Read More
Arya Fae - Boho Beauties 6

Arya Fae - Boho Beauties 6

13th August - Go behind the scenes as Arya and Giselle get ready for a hot threesome scene! We captured it all as they go through hair and make-up. All dolled up and ready to fuck, Ryan shows up to bang their brains out! These two girls couldn't keep their hands and mouths off of each other, even as they get fucked in their ass and Arya's pussy full of cum! ...Read More

Dakota Rain - Her First Time

Dakota Rain - Her First Time

3rd August - It's Dakota's very first scene! What better way to enter the industry than to have Ryan show her what a real fuck is? This might be her first time on camera, but she knows what she's doing. Ryan gives her a warm welcome and an even warmer load inside of her, fresh young pussy! ...Read More
Arielle Faye - Slut Tears

Arielle Faye - Slut Tears

27th July - Arielle is a tight, young slut who hasn't been pushed to her limits with a big dick until now! Ryan makes her take his cock deep down her throat until she tears up before punishing her pussy. She gets stretched out to the limit to make room for a huge load of jizz deep inside her snatch. ...Read More
Daizy Cooper - No B-Control Creampie 2

Daizy Cooper - No B-Control Creampie 2

20th July - Daizy loves to party, which often includes getting high and fucked hard and deep. She loves the feeling of being filled up by a thick cock while smoked up, and she doesn't care where the cum goes! She's not on birth control, but she wants Ryan's cock to pump her teen box full of his cum! ...Read More
Rina Ellis - TF's Real Life 24

Rina Ellis - TF's Real Life 24

12th July - Who wouldn't want to spend a day hanging out with exotic cutie Rina Ellis? She may be tiny at just over 5 feet tall and barely 100 lbs, but she makes up for it with enthusiasm! With perfect puffy nipples and a tight, round ass she works Ryan's cock until he can't help but fill her up! ...Read More
Honey Gold - Milk and Honey

Honey Gold - Milk and Honey

17th May - Honey Gold lives up to her name, sweet, delicious and a body that's priceless. She gets nice and sticky in a milk and honey bath before Ryan devours her pussy. He gives her a proper deep fucking before unloading two frothy creampies deep inside her honey pot. ...Read More

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Charlee Monroe - Play All Day Fuck All Night

Charlee Monroe - Teens Like It Big

20th August - Charlee Monroe put in a brand-new pool, and she can't stop splashing around in it. All through the summer months, she loves lounging nearly naked outdoors, soaking up the sun on her perfect teen body and big natural tits. At night, she calls up her favorite fuck-buddy Ryan to come over to have crazy little pool parties with his cock. ...Read More
Kelly Madison - Driving Mrs Madison Wild

Kelly Madison - Mommy Got Boobs

26th July - What do you get for the Milf who has it all? Start with a little adventure and romance, a road trip out to the ocean with a hung dude. Kelly Madison borrowed her husband's chauffeur and zipped out in their classic car on a one-way ticket to happiness. Once she seduced the driver with her huge natural tits, he opened her eyes to all the sexy fun she didn't even know she'd been missing. ...Read More
Rachel RoXXX - Drop the Bass On Her face

Rachel RoXXX - Baby Got Boobs

22nd May - Whenever Rachel RoXXX hears dark rhythms and the pounding bass of dubstep the music takes control, making her want to rip the clothes right off her big tits. There's nothing that brings her to the brink faster, except when a hung guy like Ryan Madison takes charge of her body. The two get off on playing rough, and fuck to the beat of their own drum. ...Read More

Melissa Matthews - A Roll in the Hay

Melissa Matthews - Teens Like It Big

16th April - It's just another day down at the ranch, and after some heavy lifting, Melissa is ready to climb into that pick-up truck and play with her pussy til the sun goes down. But Ryan knows just how to help her relax: by plowing her good and giving this little cowgirl a creampie surprise! ...Read More
Tiffany Tyler - Love in the Mud

Tiffany Tyler - Baby Got Boobs

13th March - It seems like gorgeous Tiffany has everything a young woman could want - beautiful clothes, gorgeous big breasts, and a house in the countryside. But she's missing something: the deep love of a wide cock. To escape it all she runs free through the mud, dirtying her toes and tits, until Ryan comes to deliver her from domestic boredom. ...Read More
Scarlet Banks - Can I Come Over

Scarlet Banks - Teens Like It Big

5th March - Scarlet is feeling horny, and finds herself online on ZZ Chat, flashing her young perky tits and breaking out her favorite toys. But soon toys aren't enough, and her chat room partner heads to her bedroom to finish the job. ...Read More
Mischa Brooks - Brooks Bouncy Birthday

Mischa Brooks - Teens Like It Big

22nd January - Little Mischa Brooks is celebrating her birthday in her very own bouncy castle! When the attendant, Ryan, tells her it's time to take it down, she pulls him in to show him just how fun bouncing with a horny teen hottie can be. ...Read More