FiLF Extra – E11 Maddy Oreilly

Sunday, September 23rd, 2018
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Anal Squats

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Girls Way – Maddy OReilly, Penny Pax And Lexi Belle

Thursday, August 16th, 2018
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Wrong Room
Video Description: responded to an ad for a casual hook up. She instructed the girl to be in her bedroom waiting for her. When she finds blindfolded, in her bed playing with her pussy, she walks in and starts kissing her. Earlier that day, Maddy O'Reilly walks into her new house and wonders if anyone's home. Penny comes down the stairs to greet her and gives her a big hug welcoming her new roommate. Penny tells her if she needs anything, she just has to come find her. She excuses herself and tells Maddy she'll see her later. Penny goes back to her room and is floored at how hot her new roommate is. She's so hot that the very idea of living with her is actually turning her one. She lies down and starts playing with her pussy. Maddy who is just as attracted to her new roommate as Penny is, would love to dyke it out with her. The only problem is that she's never been with a girl before and doesn't want to make things awkward with her new roommate. Perhaps she could find someone online to help her? When she posts an add looking a casual hookup, Lexi answers it almost immediately. The thing is, is when Lexi comes to the house she goes into the wrong bedroom! When Maddy lies on her bed playing with her pussy, she finds herself waiting longer than she anticipated. When she gets up to investigate and hears moaning coming from Penny's room, she walks in to see what's going on. When she realizes that the girl she called, to get better acquainted with the female form, is eating her roommate's pussy, she realizes she has some explaining to do. When she clears up the confusion the girls laugh it off as a simple misunderstanding. Lexi goes to excuse herself but Maddy asks her to stay, stating that two girls could provide her with the experience she needs, and you know what they say...two girls are better than one!

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Girls Way – Maddy O’Reilly, Penny Pax, Lexi Belle

Thursday, August 16th, 2018
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responded to an ad for a casual hook up. She instructed the girl to be in her bedroom waiting for her. When she finds blindfolded, in her bed playing with her pussy, she walks in and starts kissing her. Earlier that day, Maddy O'Reilly walks into her new house and wonders if anyone's home. Penny comes down the stairs to greet her and gives her a big hug welcoming her new roommate. Penny tells her if she needs anything, she just has to come find her. She excuses herself and tells Maddy she'll see her later. Penny goes back to her room and is floored at how hot her new roommate is. She's so hot that the very idea of living with her is actually turning her one. She lies down and starts playing with her pussy. Maddy who is just as attracted to her new roommate as Penny is, would love to dyke it out with her.

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Big Butts Like It Big – Maddy Oreilly

Wednesday, August 15th, 2018
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Free Anal 5
Maddy O’Reilly hates it when guys come in to her bar not knowing what they want, but is here for the secret menu, the one with FREE ANAL! Xander heard about this place from a friend, but getting blindfolded and taken to a backroom to find out he’s free to anally fuck Maddy any way he wants is more than he expected! With this busty redhead ordering him to stick it in her ass or get our Xander does as he’s told! Bending her pale ass over, spreading it wide and filling her to the brim with big dick, Xander pounds her tight little ass as hard as he can!

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Big Butts Like It Big – Maddy Oreilly

Tuesday, August 14th, 2018
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Maddy O’Reilly hates it when guys come in to her bar not knowing what they want, but is here for the secret menu, the one with FREE ANAL! Xander heard about this place from a friend, but getting blindfolded and taken to a backroom to find out he’s free to anally fuck Maddy any way he wants is more than he expected! With this busty redhead ordering him to stick it in her ass or get our Xander does as he’s told! Bending her pale ass over, spreading it wide and filling her to the brim with big dick, Xander pounds her tight little ass as hard as he can!

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Evil Angel – Maddy Oreilly And Kissa Sins

Tuesday, August 14th, 2018
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Oily Anal Big Cock 3-Way Clusterfuck
Butt-blessed redhead Maddie O'Reilly, tattooed tart 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.

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Black Pay Back – E05 Maddy Oreilly

Tuesday, August 14th, 2018
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I Have Black Friends
Who knew such a pasty becky could turn into the best whore of all for some black dick! “I’m such a dirty Fucking slut” she squeals, as the cracker was taken by rolling orgasms during a thorough ass ramming. Whitey assumed that having ‘black friends’ means she can’t be a racist like her ancestors. Ignorant cracker. However, the righteous endeavor to correct her was fruitful, a wonderful transformation occurs. The dirty whore from within emerges, and you can see the pleasure deep behind her snake eyes as she crawls to lick her new masters boots. After being taken by the pussy and anus, she exclaims her newfound distaste for ‘white boys’ and preference for a man with more melanin in his skin. She then eats a cigarette butt, like the proper ash tray she is. These snow bunnies don’t get ashy skin, but they get ashy mouths. In the end the bile covered bird turd becomes a sort of a butterfly, enlightened, and turned into chattel.

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Evil Angel – Maddy O’Reilly, Kissa Sins

Monday, August 13th, 2018
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Butt-blessed redhead Maddie O'Reilly, tattooed tart 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.

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Pure Taboo – Maddy Oreilly

Thursday, August 2nd, 2018
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The Rectal Exam
Family doctor exploits favorite patient into anal sex exam

SCENE opens with the camera focused tightly on the exposed back of a woman with a stethoscope pressed against her skin. The camera travels as the doctor's hand slowly moves the stethoscope lower down the patient's back, which elicits a light gasp and giggle from the patient without us ever seeing her face. She exclaims that the metal is a bit cold. A close-up of just the doctor's mouth, biting his lip nervously, shows us that the exposed skin and flirty noises of his patient are distracting him. 'Sorry,' Dr. Sumner says with a bit of a dorky laugh, 'just one more deep breath please?' We watch her exposed back rise and fall slowly as she breathes deep, and Dr. Sumner stares at her mesmerized. 'Gooood,' he exclaims softly. Catching himself staring, he clears his throat and lifts the stethoscope off her back. As he turns back to stand across from his patient, we see she is a strikingly beautiful woman, Yvette. In fact, Dr. Sumner finds he has trouble taking his eyes off of her as he speaks. 'Well, your breathing checks out, blood pressure is normal, and your vaccinations are all up to date... was there anything else that's been worrying you that you wanted me to look into?' Yvette looks uncomfortable as she tries to broach the subject. Actually, yes, there was something else that's been bothering her recently, but it's a bit uncomfortable to talk about. Dr. Sumner assures her that no topic is off limits, especially not for his favorite patient, and Yvette gets a bit more relaxed. Well, she elaborates, she's been feeling some discomfort in her... well, her you know, ('butthole' she mutters hurriedly), ever since she tried anal sex for the first time with her boyfriend a couple of days ago.

Dr. Sumner is visibly taken aback, and he stutters over a response as he fidgets with his coat and tie. Yvette looks let down, she had hoped that Dr. Sumner would react more professionally than this, but he apologizes - it's simply because he's been treating her and her family since she was a little girl, sometimes he forgets she's a 22 year old woman now. But she's right, there's nothing to be ashamed of, what two consenting adults do in the privacy of their homes is not any of his business. He remarks that it's not uncommon for anal virgins to experience some pain and discomfort afterwards, and that the pain should subside after a day or two as long as she was careful, they went slowly, and used plenty of lubricant. Yvette, however, doesn't seem to have been put at ease - she's read about anal fissures and tearing and the like. Isn't he even going to take a look to make sure it isn't something more serious? Dr. Sumner starts to say that it's not necessary since her level of pain doesn't seem too severe, but then he cuts himself off. Actually, yes, she's absolutely right, he should perform a thorough examination. Just to be safe. So if she can just please lift up her dress, remove her underwear, and bend over the table...

CUT TO TITLE PLATE

CUT back to just a few seconds after, only now in a male gaze perspective from behind Yvette as we stare straight onward at her bent over ass. Her pussy and butthole are on full display as she waits patiently for her doctor to take a look. He kneels down close, placing one firm hand on each cheek to spread them wider, and stares transfixed for several seconds.

'Um... doctor?' Yvette asks timidly. 'Is everything ok back there?' Dr. Sumner snaps out of his reverie and stutters that yes, he's just making a preliminary visual inspection before he runs more extensive tests. He periodically spreads her ass cheeks wide to provide the camera with ample close-up shots of her winking hole - this goes on for almost a minute, though the doctor is now more conscious to make it seem like a proper inspection by adding authoritative sounds like 'mm-hmm', 'ok', 'so far so good', etc. to keep Yvette feeling assured.

'Well, at first glance everything seems in order, but I'll of course have to palpate the inside of your rectum next, so you should brace yourself for some mild discomfort.' 'Palpate?' Yvette asks nervously, but Dr. Sumner explains that palpate just means examining by touch. It's just a clinical way of saying he'll be inserting his finger. With lubricant, of course. He asks her to remain in position while he dons his medical gloves - as he does this, we see that unbeknownst to Yvette, the doctor's attention remains fixated on her ass on display. He smears some lubricant onto his index and middle fingers, and then gets back into position behind her.

He reminds her that as he said, she might feel some slight discomfort - and then makes a bad joke about how he's sure it will be nothing compared to how it must have felt with her boyfriend sticking it in the other night. Yvette laughs nervously, not because it was funny but to make things less awkward. The doctor sticks one gloved finger in slowly, asking Yvette to describe the sensations as he does so. She describes the initial pressure, a dull ache as his finger goes deeper in, and then finally a yelp of surprise when he sticks the finger all the way in, though it quickly subsides, and she remarks that she doesn't notice much pain now that he's all the way in. He remarks that he's going to keep his finger there for a few moments, and suggests she takes a few deep breaths. He places his other hand on her ass cheek again and spreads it idly as they wait.

Dr. Sumner begins to ask Yvette questions about her first anal experience. Though as he asks his questions, Dr. Sumner coyly pulls his finger in and out, pretending it's part of the process. Did she use lube? (Yes.) Did she work her way up to the night in question by using any smaller toys to start? When Yvette says no, the doctor suggests that if she wants to continue having anal sex she should consider it, in fact he's read about women who wear butt plugs for hours at a time to stretch themselves out, even in public. Yvette blushes and says there's no way she could be bold enough for something like that. Dr. Sumner changes the subject and asks if Yvette's boyfriend fingered her first to ease her into it, and she confesses no, he didn't. Dr. Sumner explains that that may be why she's experiencing some pain now, and that it's generally better to start slow and work her way up to bigger objects. As he says this, he tells her he'll be putting in a second finger to test her elasticity. The second finger is clearly more difficult for Yvette to handle than just the one, but he eases her into it with a sense of relish.

After he satisfies himself with having fit two fingers into her hole and wiggling them around to make her squirm a bit, Dr. Sumner pulls his fingers out gently and then tells her that while things seem normal inside, he would like to get a final deeper visual inspection using a speculum. He lays Yvette on her side on the table, ass peeking out towards him, and he pulls out a rectal speculum from a nearby drawer. He inserts it carefully and uses it to expand her asshole slightly wider. Yvette remarks that the sensation is very uncomfortable, but the doctor remarks that the sensation should pass and that he promises it's absolutely necessary. However, he is clearly enjoying himself, even inserting his finger into the opening of the speculum to tease and toy with the rim of her hole. He tells Yvette that she's lucky that a 'complete amateur' like her boyfriend didn't injure her, and that they should really take better precautions next time. Yvette, slightly weirded out, remarks that Dr. Sumner really seems to know a lot about anal sex. Like, a lot.

At this, Dr. Sumner gets very embarrassed. He takes the speculum out of Yvette and removes his hands from her, putting them between his legs sheepishly. He was just offering her some advice, that's all. Yvette asks where he even gets all this advice from, she's sure it's not stuff he learned at medical school. Dr. Sumner tries to evade the question, but Yvette coaxes him - he's been a friend of the family for years now and he's helped her through some very tough times, she won't judge him. Dr. Sumner bashfully answers that he watches a lot of anal porn. Yvette grins, it's almost cute how nervous the doctor looks. She asks Dr. Sumner if he's ever had anal sex and he admits that he hasn't but has always wanted to. Yvette gets bolder, she bets that he must get awfully tempted sometimes with all the pretty girls he must have to look at as part of his job. In fact, he's always said she's his favorite patient, is that because he likes her or is it just because he's always wanted to fuck her? Dr. Sumner stumbles over his words and Yvette takes advantage of this to coax him further. He's right that her boyfriend is a complete amateur. In fact, having anal sex with him hurt like hell. But she bets that if a real man showed her how to do it, a man who's completely obsessed with anal sex, he'd know how to do it right. She reaches for his crotch and he pulls back, it would be unethical. She gets up off the table and approaches him seductively, insisting that no other patient of his is ever going to go along with something like this, this is a once in a lifetime chance and he'd be an idiot to turn it down. She wants it, he wants it. What could be more ethical than that? She leans in for a kiss and he hungrily kisses back, his hands going straight to gripping her ass cheeks tightly as they embrace.

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Pure Taboo – Maddy O’Reilly

Thursday, August 2nd, 2018
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SCENE opens with the camera focused tightly on the exposed back of a woman with a stethoscope pressed against her skin. The camera travels as the doctor's hand slowly moves the stethoscope lower down the patient's back, which elicits a light gasp and giggle from the patient without us ever seeing her face. She exclaims that the metal is a bit cold. A close-up of just the doctor's mouth, biting his lip nervously, shows us that the exposed skin and flirty noises of his patient are distracting him. 'Sorry,' Dr. Sumner says with a bit of a dorky laugh, 'just one more deep breath please?' We watch her exposed back rise and fall slowly as she breathes deep, and Dr. Sumner stares at her mesmerized.

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Everything Butt – Vienna Black , Maddy O’Reilly, Dana DeArmond

Saturday, July 14th, 2018
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is a fierce boss bitch and she runs a strict anal modeling agency. Dressed in a tight black dress and high heels, she demands loyalty and respect from her obedient employees. Her ASSistant, the curvy natural beauty Maddy O'Reilly know exactly how to serve her boss. She will do anything to kiss Dana's perfect ass. The new girl, petite anal newbie , is looking to work in the industry and needs to land this job. Her showing up late to the interview gets Dana worked up and ready to deliver a brutal punishment to her new intern. Starting with rimming, Vienna is made to use her long tongue to fuck Dana's asshole wet. Maddy then brings out the metal dildo to pop Dana's asshole right gaping open. Eager to please, Maddy is next inline for the metal dildo to show Vienna how it's done. Maddy cums hard right away from the anal fucking and it's now time for Vienna to get to work. Stuffed with a butt plug, Vienna's face is bound with a strap on dildo to fuck her new boss. Vienna has a front row view of her bosses perfect gaping asshole as she is made to fuck Dana deep. Maddy is again eager to show off and cum for her boss and she takes the first fist before both girls are stacked ass to ass ready for the bosses huge strap on cock. Both the girls get their asses rammed which causes Maddy to scream with body shaking orgasms. Looks like Dana found the perfect assistant for Maddy.

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Everything Butt – Vienna Black, Maddy Oreilly And Dana Dearmond

Saturday, July 14th, 2018
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's Anal Agency: Boss Bitch Trains Anal Newbie
Dana DeArmond is a fierce boss bitch and she runs a strict anal modeling agency. Dressed in a tight black dress and high heels, she demands loyalty and respect from her obedient employees. Her ASSistant, the curvy natural beauty Maddy O'Reilly know exactly how to serve her boss. She will do anything to kiss Dana's perfect ass. The new girl, petite anal newbie , is looking to work in the industry and needs to land this job. Her showing up late to the interview gets Dana worked up and ready to deliver a brutal punishment to her new intern. Starting with rimming, Vienna is made to use her long tongue to fuck Dana's asshole wet. Maddy then brings out the metal dildo to pop Dana's asshole right gaping open. Eager to please, Maddy is next inline for the metal dildo to show Vienna how it's done. Maddy cums hard right away from the anal fucking and it's now time for Vienna to get to work. Stuffed with a butt plug, Vienna's face is bound with a strap on dildo to fuck her new boss. Vienna has a front row view of her bosses perfect gaping asshole as she is made to fuck Dana deep. Maddy is again eager to show off and cum for her boss and she takes the first fist before both girls are stacked ass to ass ready for the bosses huge strap on cock. Both the girls get their asses rammed which causes Maddy to scream with body shaking orgasms. Looks like Dana found the perfect assistant for Maddy.

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Squirtamania #21

Wednesday, July 11th, 2018
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Cast: , , , , Maddy O'Reilly

Description: WOW! These girls squirt more than all the water in the world! Ain't no party like a squirting party!

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Allgirl Massage – Charlotte Stokely, Luna Star, Maddy O’Reilly

Monday, July 9th, 2018
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has just hired to work at her massage parlor and is in the process of training her. One of the regulars, Maddy O'Reilly, is coming in for her afternoon appointment and Charlotte would like Luna to give her the massage. Charlotte excuses herself, instructing Luna to man the reception area while she attends to some things. Maddy walks in and introduces herself to Luna and the girls hit it off. When Charlotte walks back in the room she notices the chemistry between them almost immediately. As she checks out both of these beauties, she suddenly realizes that she doesn't want to miss out on any of the action. She approaches them and informs Maddy that since she's such a great client, they're going to give her a 4-hand massage.

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All Girl Massage – Maddy Oreilly, Charlotte Stokely And Luna Star

Monday, July 9th, 2018
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Two Is Better Than One
has just hired to work at her massage parlor and is in the process of training her. One of the regulars, Maddy O'Reilly, is coming in for her afternoon appointment and Charlotte would like Luna to give her the massage. Charlotte excuses herself, instructing Luna to man the reception area while she attends to some things. Maddy walks in and introduces herself to Luna and the girls hit it off. When Charlotte walks back in the room she notices the chemistry between them almost immediately. As she checks out both of these beauties, she suddenly realizes that she doesn't want to miss out on any of the action. She approaches them and informs Maddy that since she's such a great client, they're going to give her a 4-hand massage. Maddy is ecstatic and eager to get started as she tears off her clothes in anticipation. She lies on the table and the girls start massaging her feet. They work their way up her legs while massaging her thighs. When Luna's hands get close to Maddy's pussy, she starts wondering if she should be so close to it. She asks nervously if Maddy should turn around now. Charlotte and Maddy chuckle at her comments, remembering that she is indeed a newbie! Maddy turns around as Charlotte massages her inner things and Luna focuses on her breasts. When Charlotte starts massaging Maddy's pussy, Luna starts understanding what her job actually entails. When she finds herself getting turned on, she realizes she made the right decision taking this gig!

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Girls Way – Maddy Oreilly And Jenna Sativa

Monday, July 2nd, 2018
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Hold The Phone: Conference Call
is on the phone with a client. She's working from her office at home and is eager to get off the phone. While she explains the pros and cons of branding to her client, Maddy O'Reilly walks down to see her and she looks incredible. Wearing nothing but sexy pink lingerie, she walks up to Jenna and starts massaging her shoulders. Jenna is busy talking to the client but it's clear that Maddy just wants to have some fun. She starts running her hands-on Jenna's chest and squeezing her tits. Jenna looks at her and asks her to stop but Maddy is having way too much fun to do that. Maddy picks up a pen and starts running it on Jenna's skin as Jenna tries to push it away. She runs it down her chest and then starts running it up Jenna's leg. Jenna moans as she moves the phone away from her mouth telling Maddy how bad she's being. The client overhears her and Jenna has to correct herself as she asks Maddy to stop. Maddy smiles indicating that she's not done having fun just yet! Maddy spreads her legs open and runs her hands in between her thighs, she grabs her tits and squeezes them as Jenna gets so turned on she barely is paying attention to the client on the other line. When Maddy starts eating Jenna's pussy, it clear to Jenna that it's high time she put an end to this call and pay attention to Maddy who's got her face deep in wet pussy!

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Girls Way – Maddy O’Reilly, Jenna Sativa

Monday, July 2nd, 2018
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is on the phone with a client. She's working from her office at home and is eager to get off the phone. While she explains the pros and cons of branding to her client, Maddy O'Reilly walks down to see her and she looks incredible. Wearing nothing but sexy pink lingerie, she walks up to Jenna and starts massaging her shoulders. Jenna is busy talking to the client but it's clear that Maddy just wants to have some fun. She starts running her hands-on Jenna's chest and squeezing her tits. Jenna looks at her and asks her to stop but Maddy is having way too much fun to do that.

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Yoga Pants

Tuesday, June 12th, 2018
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Cast: , Maddy O'Reilly, , , , , ,

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Get Your Knees Dirty – Maddy Oreilly

Sunday, June 10th, 2018
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Get Your Knees Dirty – Maddy Oreilly

Saturday, June 9th, 2018
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