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Showing 1-60 of 133 Results

Dommey Mommy video from Madisyn Wood

Dommey Mommy I walk in about to go to the gym and I catch you masturbating! Mommy owns you and you know it's against the rules for you to touch yourself without permission, I verbally reprimand you and tell you now I'll have to use your cock however I wish. I put you in your place while I suck and fuck your cock, you belong to mommy completely. (loosely a part 2 to my video "You Belong to Mommy"). I decide that since you're a good boy you can fill me (implied), after all I do love you sweetie.

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Cheating Mommy Blackmailed video from Madisyn Wood

Cheating Mommy Blackmailed DISCLAIMER: anal is with my small glass dildo, watch the teaser. I come home late, your dad is out of town, and you tell me you know "the truth" I play dumb but you blackmail me that if I don't strip you'll tell my husband. So I strip, embarassed. Then you demand that I get on my knees, and you shove your cock down my throat. I gag on it as you roughly use my throat, I beg you to find another way. But then you punish for my cheating further and use my pussy. I wish you would let this go but you don't... you shove your cock in my ass and not even your dad has fucked me anally!!! You cum in my ass despite my protests. It feels good, but it's so wrong.

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FATHER FIGURE video from Madisyn Wood

FATHER FIGURE [slow burn beginning; flirting; slow buildup; taboo sorta] we are actors on a tv show where we play DAD and DAUGHTER. But we've known each other for years, it's like I'm one of your own... we are like famil...we spend so much time together. There's an intro scene where we are about to shoot the last scene of the season and some setup of the video. Then, We are celebrating the end of a season and I'm in your trailer after the party. It starts innocent, then gets sexually tense slowly but surely, it's late and we're alone. I love you but sometimes I love you a little different. Like a step-DAUGHTER. But one that really wants to fuck you. [first kiss 12 MINUTES IN] Then we get passionate fast. We use taboo terms for one another. We do a few positions [all virtual sex]. We take it all out on each other all this pent up passion for each other. we cum together and i beg you fill me.

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Your Best Friend's Little Sister video from Madisyn Wood

Your Best Friend's Little Sister [slow burn, lots of talking,, virtual sex] [FIRST SEXUAL ACTION 15 MINUTES IN] You are my older brother's best friend. So we've known each other for years but nothings ever happened between us of course. my brother told you to never make a move on me... But tonight you've just gotten back from a long 18 month work assignment. It's your welcome home party, i tease you and we chat at the beginning, about you coming back and I asked if you met any girls while you were gone... And then I mention I will be staying there at my step-brothers that night and not at my boyfriend's because we're on and off. But because you just got back you were going to stay here too... It's after the party, everyone's gone. We're in the guest bedroom. And we end up talking about my boyfriend, I ask you to sit on the bed and shut my door I don't want to be overheard. I start talking about it slowly, hesitantly... the spark is dying, he doesn't want m enough. I try to avoid saying that "we aren't having sex" without saying IT. I lightly flirt with you, asking you if you're going to get a 2 bed apartment, I sit closer, joke that you can crash in here, and I start leaning forward (inching closer) as I talk about when I was younger maybe I had a crush on you and the other boys.. but I definitely wouldn't now. Then i kiss you. But you pull back (15 MINUTES IN). You tell me to stop but I start getting naked. I show you my body. You just don't want to get in trouble. You want to stay true to your friend who told you not to touch me. But You can't hold out forever. Not with me showing off my holes. I sit and grind in your lap before fingering. Dirty talking as well. I'm so pent up and it seems you are too. I get in prone and move my ass on your cock while you fuck me. I cum hard and then get on top and ride out your creampie. I've been wanting to be filled so bad. I want to leave my boyfriend for you, a real man who will fuck and fill me.

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Neighbor Squirts in Your GF's Clothes video from Madisyn Wood

Neighbor Squirts in Your GF's Clothes I'm your new neighbor and this is a bit of a slow burn. I come over and we chat and I learn you have a girlfriend but she's always at the gym and not with you. I'm on the college cheerleading team. But I come over a few days later and tell you I got injured so I can't be on the team... so I'm trying out for more clubs/sports BUT I don't have any clothes! Could you girlfriend lend me one??? You reluctantly let me try one of hers on at your apartment but I find her stash of sex toys... why does she even need these if she has you? I start touching myself and then rush home to finish myself off, squirting multiple times in her clothes. You had given me your keys to return the clothes, but instead I come over to borrow another since I soaked the first one. I try on more of them, read her diary and soak another one of her outfits. She doesn't deserve you! I want you secretly, so fucking bad, I squirt in your bed before rushing to try-outs. I want to be a homewrecker so bad

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Cheer Slut's Rich Cock video from Madisyn Wood

Cheer Slut's Rich Cock Part 3!! I was representing our program at a charity / benefit event where I run into you at the rooftop bar. You and your wife run some big company, and you start confiding in me. I recognize what i can do, I can be there for you: a rich, wealthy man who's wife doesn't care for him. [[ FIRST 5 MINUTES OUTSIDE OUTDOORS ON A BALCONY WATCH PREVIEW ]] We're laying on the bed and I seal the deal - some type of I give you something, you help me out with college sort of deal, wink wink. No need for your wife to know. I stroke your cock with my feet and tell you how you will have to fuck me raw and creampie me, you must. I talk about how you much you've needed a tighter pussy like mine, how much you want to fill me. I'm determined to take it raw. We fuck prone for a while before i ride your cum out. The next morning you left a goodbye note... and I charge room service to your card. --- --- series description --- Welcome to the life of a fiercely ambitious college cheerleader, perpetually stuck in second place in competitions, academics, and life, who’s determined to claim the top spot in everything. She pushes the boundaries of seduction, corrupting each of 4 men into cheating and creampieing her, even though its unprotected and risky. She becomes obsessed with every man's release inside her, manipulating desires and risking everything to seize pleasure, power, and victory.

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Creampied by Coach to Make Cheer Captain video from Madisyn Wood

Creampied by Coach to Make Cheer Captain Part 4!!! FINALE!! ITS THE COACH! I'M FINALLY GOING TO GET CHEER CAPTAIN! But this requires the most manipulation and seduction. This is the most slow burn of them all. I've honed my craft as a whore now. I've been spying on coach to get intel on his girlfriend. I slowly wear him down about him as I tease and push him, flashing my panties, then my tits, then my pussy, then fingering myself, until he finally gives in. I ride the coach's cock in reverse cowgirl esque before taking it missionary / legs up. I get his creampie and put my panties back on so they're soaked with cum, perfect for practice right after this. I convince him how I will help this team, just like I will help his relationship by fucking him. I get everything I want, finally. --- series description --- Welcome to the life of a fiercely ambitious college cheerleader, perpetually stuck in second place in competitions, academics, and life, who’s determined to claim the top spot in everything. She pushes the boundaries of seduction, corrupting each of 4 men into cheating and creampieing her, even though its unprotected and risky. She becomes obsessed with every man's release inside her, manipulating desires and risking everything to seize pleasure, power, and victory.

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Railed By the Quarterback video from Madisyn Wood

Railed By the Quarterback Part 2 of Cheerleader Confessions: Quarterback. I'm walking to cheer practice and I "coincidentally" see you in your car about to go to football practice (they're at the same time). I chat you up and slip in a few digs about your sorority princess gf. I realize I forgot my top for practice!! I ask you to take me back to my dorm super fast to get it. (first 5 minutes in my car) When we're there you come up with me. I flash you and continue seducing you until I've appealed enough to your alpha male ego to fuck me. I tell you to use me and get on my knees. I can cheer hard for you,, and I can get fucked hard for you. I lay on my side and fuck you. then we fuck missionary until you creampie me, i can't wait for it to drip out onto the field.

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Girlfriend Surprise Move-In video from Madisyn Wood

Girlfriend Surprise Move-In I surprise you by moving in, and I'm already redecorating your apartment when you come in!! [PART 3 OF 5] You are Pookie, I am your one and only. Why are you upset? can't you see this will bring us closer together?? We go back and forth but i know you can't resist me! I suck on you and then stroke you with my feetsies. we belong together pookie! I ride you to convince you, all cowgirl pov until you fill me, no protection needed between us. creampies only for your one and only. so happy we're living together now!

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Your New Clingy Girlfriend video from Madisyn Wood

Your New Clingy Girlfriend Your new girlfriend is a bit fanatical. Obsessed. Over-the-top cute. and, annoying! Maybe a bit crazy...[ PART 1 OF 5 ] She calls you Pookie. Her pussy is the honey pot and she wants your cummies!! She gives you a new outfit to wear for your special anniversary and seduces you with her cute toesies. After eating her honey pot, she licks your penis... to her "mr.wiggles" and then gets on top cowgirl pov to ride you. Of course you can cum in her without a condom, you are sooooo close now!! Nothing could go wrong messing around with this girl right...

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Cheerleader Raises Her Grade video from Madisyn Wood

Cheerleader Raises Her Grade Part 1 of the cheerleader's quest for everything. She comes to her math professor's house. Flirts a little and sees his wife is gone. Claiming she's sweaty after practice she takes her panties off in his living room and invites herself into his bedroom. They make a deal that she'll fuck him for a better grade. She's very forward about it and takes his cock out, sucks it, takes it in missionary, rides it reverse and fowards before begging to be filled, claiming it's "safe". During sex she talks about cheating, creampies, how shes better than his wife, shes a slut cheerleader, and how bad she wants her A. After filling her, she mentions she's not actually on birth control.... --- series description --- Welcome to the life of a fiercely ambitious college cheerleader, perpetually stuck in second place in competitions, academics, and life, who’s determined to claim the top spot in everything. She pushes the boundaries of seduction, corrupting each of 4 men into cheating and creampieing her, even though its unprotected and risky. She becomes obsessed with every man's release inside her, manipulating desires and risking everything to seize pleasure, power, and victory.

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Meeting Her Family video from Madisyn Wood

Meeting Her Family PART 2 OF 5 - Your new girlfriend is a bit fanatical. Obsessed. Over-the-top cute. and, annoying! You are Pookie, I am your one and only. I just worked out and surprise! you're meeting my family today! My step-mommy and step-daddy! get ready for dinner... you don't want to??? but we've been together for 3 WHOLE MONTHS. We go to "dinner" and I give you a footjob under the table and OMGG you say "I love you" for the first time. Back at home we fool around, you eat my honey pot and I suck on "mr.wiggles" before we have sex in missionary, my feet in your face with cute little toe rings. You fill me, and get rid of any old condoms you might have, cummies are for inside only.

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Cheerleader Confessions video from Madisyn Wood

Cheerleader Confessions ***INTRO PART TO MY NEW CHEERLEADER DIARIES*** First 5 minutes you see me coming up with a plan as I get ready for a game, I'm thinking to myself about how I'm going to fuck my professors, the quarterback, some man with money, and eventually the coach. The rest is a compilation of sexting images and short videos I'm sending to these men, this video is the "curtain pulled back" from the rest of the series, the POV you don't see unless you're me. --- Welcome to the life of a fiercely ambitious college cheerleader, perpetually stuck in second place in competitions, academics, and life, who’s determined to claim the top spot in everything. She pushes the boundaries of seduction, corrupting each of 4 men into cheating and creampieing her, even though its unprotected and risky. She becomes obsessed with every man's release inside her, manipulating desires and risking everything to seize pleasure, power, and victory.

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Riding My Biggest Toy video from Madisyn Wood

Riding My Biggest Toy I ride with my ass facing you in two positions, reverse cowgirl and a "side ride", kind of like spooning riding. I'm obsessed with the feeling of my biggest toy, stretching me, wrecking me, ruining this pussy. I ride my biggest dildo and cum a couple times from the feeling of it stretching me out so well. I keep my ass oily and twerk my ass all over my thick dildo. This is a bad dragon medium mystic dildo, for those wondering.

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Caught Rubbing My Pussy video from Madisyn Wood

Caught Rubbing My Pussy I'm playing with myself, watching porn and riding my fingers, rubbing and grinding on them, after about 4 minutes as I'm about to cum I see you. But it's too late - I can't stop myself - so you watch me cum as I'm embarrassed and mortified. it's implied that you're my roommate. You're super hard even though I'm embarassed so even though I'm feeling a bit shy, I take it out for you. I suck you off and you cum in my mouth (implied). I start riding you, all shyness gone now, from behind and then cowgirl and we cum together as you fill me once again. I guess I'm glad you walked in on me after all.

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Your Worst Student video from Madisyn Wood

Your Worst Student I'm a freshman, only 18, and you're my professor. I'm failing your class and come to your office hours to discuss it. But I've heard that you have a weakness for dumb sluts, and I know how to get my A. I talk very dirty and slutty about myself: dumb, stupid, idiot, bimbo, whore, slut, bitch. I ride you (virtual sex) and sit right in front of you and degrade myself for 5 straight minutes until you cover my face. I'm going to go from your worst student to your best student!

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Twerk Party Slut video from Madisyn Wood

Twerk Party Slut [all dildos/cum implied] We are getting ready to go to a party but I don't know what to wear! I try on a bunch of slutty outfits and twerk in them because I need to make sure my ass can still shake in them. You start to get hard at me changing so i let you jerk it to me while I twerk and beg you to cum in my mouth before we leave (first 13-14minutes) Then we're at the party!! My boobs keep popping out and boys keep looking at me, soon there is a bunch all around me, you included. I let them all take it out and jerk it to me, encouraging them. I love twerking in the center of all these cocks. I beg to be covered in their cum (no dildo or cum shown, just implied). Filmed during cicada summer, watch the preview.

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Under Your Wife's Control video from Madisyn Wood

Under Your Wife's Control THE FINALE OF THE CRAZY GF TAKEOVER, except now I'm your wife. [ PART 5 OF 5 ] We have been married for a few months and now I hold all the cards. I'm in control now, there's been a power shift. You answer to me. Of course I'm still your cute young wife, but things have changed. Each day this week we have our little interactions, but you aren't being the perfect husband yet. So on friday before you leave for "guy's night" I tell you that you're not going. You haven't earned it. Maybe once you make it up to me you can go tomorrow. I start by riding your face, making you taste me and show me you're sorry (pov face riding). This is soft femdom, not harsh or humiliating. Then, I ride you because of course I have to be in control of our pleasure. And, because I'm nice and you seem sorry I let you creampie me. See? that wasn't so bad. I know you love me. [ PART 5 OF 5 ]

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Breed Your Boss for Your Bonus video from Madisyn Wood

Breed Your Boss for Your Bonus I'm your boss and you've been underperforming, I can't just give you the same bonus as everyone else for nothing. So you have to do something for me: get me pregnant. I try to keep it professional but you won't have that. You convince to fuck in doggy even though I think its a bit demeaning. Your cock is bigger than I thought, too. I guess I thought I'd have more control in this situation than I actually do. I ride you until you cum in me, but after you creampie me, you request that instead of getting the bonus you want to cum on my face, and I reluctantly agree. I mean its easier for me technically but it doesnt mean I dont think you're a bit sick for wanting to facial your boss instead of taking the money. You shoot it all over me and I tell you if I dont get pregnant you're fired. Or if you try and tell anyone about this!

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GF Wins You Back - Two Ways video from Madisyn Wood

GF Wins You Back - Two Ways [PART 4 OF 5] THIS VID IS LIKE 2 VIDEOS IN 1! Your new girlfriend is a bit fanatical. Obsessed. Over-the-top cute. and, annoying! You are Pookie, you are her one and only. I find you were cheating on me, but I won't confront you. Not like other girls. I have two options... play it nice or play it rough. The angel and the devil on my shoulder. In the first clip I am sooo sweet, I draw you back in. I am the good sweet angel. I use my feet and my mouth on you before you fuck me missionary and creampie me. In the next alternate ending, I am intense. I am rough. I spank myself, gag myself, I'm kinky. I draw you back in with the rough excitement of kinky sex. I ride you hard with body writing until you creampie me again. In the very end, it's the same. You're mine and only mine. forever.

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Neighbor's Wife Needs Breeding video from Madisyn Wood

Neighbor's Wife Needs Breeding I'm your neighbor. You and your wife seem so happy together, and I'm over to clean your house. I clean houses around the neighborhood for extra cash. But I slowly start to explain how my husband and I are having a problem. We've been trying to get pregnant, and nothings working. The problem is him. So I gently seduce you so you can impregnate me. I dirty talk about how I'm better than your wife. Your dick is hugeeee so it must mean my husband has a tiny dick and I never knew. You are so much bigger, I beg for your creampie... we'll have to keep doing this until I get pregnant ;)

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Coworker Caught Stealing video from Madisyn Wood

Coworker Caught Stealing i followed you home from work because you saw me doing... NOTHING AT ALL -_- anyways. I slowly seduce you so you don't go running to HR, flirting and making it obvious but not too whore-ish that I will do what it takes to keep you quiet. I flash you again and again before touching myself, then I suck your cock before riding you front and back, begging for your creampie. If you want to feel this pussy again, you'll keep your mouth shut.

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Stealing Daddy for Myself video from Madisyn Wood

Stealing Daddy for Myself [100% VIRTUAL SEX NO PENETRATION SHOWN] we're on a trip together that I invited you on. I heard about you and my friend, did you think she wouldn't tell me? that's messed up you'd fuck my friend... instead of me. I mean we're both the same age and look kinda similar. Why don't you just admit you want ME? You try to resist but I am confident. I show you my body and I see you getting turned on. I don't bother with foreplay and sit on your cock, virtual sex cowgirl and reverse cowgirl. I face you so I can watch your face while you fill me up, of course I'll let you fill me, we're related after all. The closest we could possibly be.

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Falling For Daddy video from Madisyn Wood

Falling For Daddy MULTI PART TABOO ROLEPLAY - I come in and start putting on my suntan lotion to go tanning, we've gotten close since mom cheated on you and left. You help me after a bit by putting the lotion on my back, I notice that your dick is really big in your pants but I don't say anything, but I'm shocked... A bit later and I'm looking for my sunglasses before I go tan, but accidentally walk in on you stroking your dick with my panties!!!! I'm so confused and embarrassed. I run away and think about it in my room. It was hot but I'm feeling so confused,..... Later that night and i've avoided you all day. I can't stop thinking about your cock daddy. I start touching myself to the thought of you and use my vibrator until I cum (for real)..... Then, [for the last 10ish minutes] I sneak into daddy's bedroom and take out his big hard cock, start sucking on it until he wakes up. I ride him and then we fuck in missionary until he pulls out and cums on my pussy.. We're closer than ever now.

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Pornstar Siblings video from Madisyn Wood

Pornstar Siblings 100% VIRTUAL SEX BUT HOLES SHOW - naked the entire video - 3 parts Part 1: I'm nervous to ask you but you're my last resort. I make amatuer porn and I need to get a video out NOW, please help me. We'll just do something easy like a handjob and no one will know it's REAL taboo, they'll think its roleplay. During the video I'm "acting" for the camera doing intentional bad acting because we are actually family. You cum in like 2 minutes and when you hit "stop" I'm super pissed, I need content not 2 second clips. Part 2: I'm back a couple days later and apologize, the video actually blew up. And even though I'm nervous to make another with my step-brother, I need you. So I ask for us to do a BJ and if you cum this time we'll keep going. I suck your cock and again it's more bad porn acting for the camera, and then I ride you. Even though I'm fake enthusiastic for the camera, I whisper not to cum in me. You do. I'm upset but not as upset as I could be... something is shifting... Part 3: Surprise, our video is going viral!! another? I'm not nervous this time and my dirty talk is getting a lot more natural. I'm fucking you harder (I was twerking hard my camera loses focus a couple times super brief). I'm actually moaning for real and beg for you to fill me for real. I want to continue the video even after you cum, little bro. I've fallen in love with fucking you, I can tell you're attracted to me, (and this dirty talk gets fucking hot I'm not gonna lie). It's so fucking wrong I can't stop fucking you. It's not an act anymore, I don't even care if it's filmed or not

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Making You Mine: Female-Led Seduction video from Madisyn Wood

Making You Mine: Female-Led Seduction 4 parts [ALMOST AN HOUR LONG SEDUCTION MOVIE] SOFT FEMDOM / FEMALE-LED TONE TLDR: We are close friends, you are still a shy virgin but start dating this girl Kayla. I hatch a secret plan: I try to "help" you with her, getting you comfortable with sexual acts that get more explicit.... but really I want you for myself. Finally she breaks up with you and you see, I'm the one you really need. Give yourself to me. I am very confident and a bit bratty, this is the start of a female-led relationship. Part 1: You're texting this girl trying to go on a date with her, Kayla. I help you while you massage my feet as a thank you. I text her for you and she's going to come over soon! But, everyone knows you can't go on a date without cumming first. I'll just help you. It's what friends do. I give you a footjob until you cum on my feet, you're welcome. Part 2: I ask you about the date the next day, you said she wanted to do more but you felt "drained". Well, I think it's just because you don't have enough experience and you're nervous. I coach you on making out and touching me, and I suck your cock with my feet in your face. BUT KAYLA'S AT THE DOOR!! She comes in and talks to you while I secretly suck you off behind the couch and you cum in my mouth. Oops! Part 3: After another date with her, you come talk about it with me, again she wanted to do more but you felt "spent" after cumming in my mouth. I think it's time you lose your virignity and what better person then your best friend?? You eat me out, we have sex and you creampie me. You'll be able to seal the deal now! Part 4: sadly, she broke up with you! I comfort you at first, before turning up the heat. I mean, I made you cum more than she ever could. I give you what you need, I know all your kinks and love how you are weak for my feet. We can just be together. Give yourself to me, pledge yourself to me. I squat ride you with and without my big heels on. And you creampie me big this time. You were meant to be mine.

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Nonstop Squirting and Sucking video from Madisyn Wood

Nonstop Squirting and Sucking 15 minutes of sloppy sucking and 45 minutes of squirting! Need a break from the roleplays and ready to get right to the point? I show you what a slut I am! I use a bunch of toys and play with myself a ton!

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Lingerie Store Homewrecker Returns! Part 2 video from Madisyn Wood

Lingerie Store Homewrecker Returns! Part 2 I'm here to be your new babysitter! Didn't think you'd see the lingerie store girl you cheated with ever again? Well now you can hire me and we'll see each other allll the time! I try on a few different bodystocking outfits for the first 12 minutes and seduce you until we have rough dirty talk sex where I ride you in a few different positions, and beg you to fill me. I talk bad about your girlfriend and how I'm better than her, it's just the truth.

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Lingerie Store Homewrecker video from Madisyn Wood

Lingerie Store Homewrecker You come into the lingerie store and I am working. You want to see some outfits for your girlfriend and I try them on so you can get a better idea of what they look like but I am revealing my body to you. I like how you look at me and I tease you about it, tease you about if I look prettier than your girlfriend, building the tension between us. After about 9 minutes I confront you straight up because I know you want me and you should just forget about your GF. I suck your cock then turn around and we fuck in doggy until I cum on your thick dick. I lick my juices off and lie down, you fuck me in missionary and pull out to blow your seed on my pussy lips

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Lingerie Salesgirl Sex video from Madisyn Wood

Lingerie Salesgirl Sex You need help picking something out for someone special and I'm new here but I would love to help you! You come to the back but when I show you some pieces you insist that I TRY THEM ON. I don't know but I guess that's okay, I try on a couple outfits, when you insist that I cum for you, so I rub my pussy until I cum. But now I'm sooo turned on I beg to fuck you! I ride you until you cum inside me (implied), but your cock is still HARD! So I suck you off until you cum again and I swallow it all up. now we better clean up before someone finds us!

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Neighbor Squirts in Your GF's Clothes PART 2 video from Madisyn Wood

Neighbor Squirts in Your GF's Clothes PART 2 [all solo female no interaction with a pov, technically voyeur all the way] this video picks up right when part 1 ends; I'm running back into my apartment, an armload of your girlfriends stolen clothes and leggings soaked in squirt. I throw them all down. Cheer tryouts are coming up in an hour buttt... i'm still horny. I strip off the wet outfit and finger and rub my pussy until I squirt. Then I quickly get dressed in a new outfit and go off to tryouts. In the next scene I'm re-entering my bedroom.... I got rejected. My cheer bestie calls me, two girls already got injured on the team and I hope she's about to say they need a replacement but nope. they might be looking for a massage therapist though and physical therapist. I lie. hard. I will take anything to be on the college cheer team. I start trying on outfits for my masseuse audition tomorrow - still your girlfriends outfits i stole - when you CALL ME. I decide to go back over to your apartment with your keys and snoop some more. I look for more normal clothes, she has none. But i do find some bikinis. I try some of those on and steal those too - along with her DIARY. I read it at home and confirm she's cheating on you. I start touching myself again and this time put back on the yoga pants outfit and squirt through the leggings, so hard I soak my comforter underneath me.

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HAUNTED video from Madisyn Wood

HAUNTED [[MY FAV RELEASE OF 2025]] This film is about a horny young woman. She hungers for self-pleasure above all else. Though, her perverse desires clash with the expectations of those around her. Guilt, from making herself cum instead of seeing friends, having sex with her boyfriend, or even stepping outside, unravels her mind. This is her descent. **** one of my only detailed SELF--SCRIPTED films to exist*** ALL SOLO FEMALE MULTIPLE ORGASMS, VOYUER/WATCHER - STYLE MOSTLY ~detailed summary~ She starts getting ready to see her best friend, determined to leave this time. Until she talks to her friend and decides she'd rather stay and touch herself. As she starts to do just that, the phone rings again: but it isn't friendly.... She hangs up and keeps going. Nothing really keeps her from cumming anymore. Next day, she's dancing seductively in her apartment, feeling her own self. Her boyfriend calls. She'd rather feel her own body than suck his cock so she blows him off, still though, some weird things keep happening. She strips and dances more, though her paranoia remains. Another day, she's about to cum on her countertop in the kitchen; she's riding one of her many dildos. After she finishes she starts making popcorn. She can't even wait for it to be done before she starts fucking herself AGAIN. Before she can cum the phone rings. Who is it? Someone. In. The. House. in the drawer, the dvd says "Play Me" SPOILERS AHEAD SPOILERS AHEAD SPOILERS AHEAD We watch on the TV as not just anyone, but the nympho herself is on the TV voyuer-style, masturbating. Suddenly, She stares through the TV and degrades the female watcher. Exposes her. The scared viewer loses it. Goes into her bedroom to find tons of sex toys out (she didnt put them there). And gives in. She degrades herself as she cums mulitple times and plays intensely. She gives in to her guilt, admits her shame. Touches her pretty pussy. Cums. Cums. Cum. Cum. Have you cum yet? Vibrator, dildos, pussy fucking, grinding, fingering, voyuer , erotic, plot based, story driven slow burn

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Secret Stripper Daughter video from Madisyn Wood

Secret Stripper Daughter two towns over and you still found me. fuck. we go into one of the private dance rooms so we can talk privately. I feel so caught, here I am barely old enough to be a stripper and working here, oh no. But then... what's HE doing here??! I realize we both have secrets. I slowly seduce him, dancing and flirting, pushing it further and further until I'm naked and moving my body above him (lap dance pov-style esque). I need to take my time, I can't give up this chance to finally get stepmom out of the way and have you for myself. and then you can't resist anymore. I suck on your cock before riding you (all cowgirl all forward) I beg for your cum, i dirty talk about your cock, about the taboo-ness, about how jealous i was of MOM and how much hotter i am than her. Guess we both have a secret now to share.

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Train My Tight Ass video from Madisyn Wood

Train My Tight Ass I'm dressed up with my socks heels, tiny skirt and g-string.. and buttplug already! I dirty talk about how much i need it to be trained while I tease with my holes, ass, and feet. I want to be your anal-loving slut. I'm still an anal virgin, your cock would be the first (true!!) I take the plug out 8min in and then start fingering my ass. It's so tight it grips my finger so good. I don't do deep fingering, instead focusing on rubbing and shallow fingering in and out to get those wet lubey noises in a few positions.(14:00-21:00) I start with my glass dildo, again shallowly. Training it makes me soooo wet. I keep fingering it and loving it so much.

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Free Use Bitch Roomie Part 2 video from Madisyn Wood

Free Use Bitch Roomie Part 2 PART 2 !! - I've been your free use bratty roommate for a bit, so that you'll let me live here as long as I want. but then one day you say you have a date later? WTF?? I satisfy your needs, why are you trying some other bitch out? I am clearly jealous and I don't want you to have an excuse to try to kick me out again so I make you drain your balls for me before you leave. I suck you just the way you like, reverse ride your cock and twerk on it before you bend me over on my hands and knees and let you fuck me deep. I keep riding you and make you late for your date, I talk bad about her, talk about how much better I am and bitch about her. I cum with you inside me as you cum for me.

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Free Use Bratty Roomie part 1 video from Madisyn Wood

Free Use Bratty Roomie part 1 I'm your roommate and we've lived together for 6 months. but you just got a new job and pay bump and want me to move out because you can afford the whole apartment for yourself. I'm not moving out!! forget that!! I'd do anything to avoid that, I'd even fuck you before i left this. Unless.... I mean I never see you with girls at home. You must be hard up or something. We come to our little arrangement. I give you a sensual blowjob and sass you a little, I might let you fuck me now but it doesn't mean I'm not a brat. You fuck me on my side and in missionary before i let you cum in me. PART 1 OF 2!!

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Mommy Takes Your Virginity video from Madisyn Wood

Mommy Takes Your Virginity You book a session at a massage parlour/brothel type place but to your surprise YOUR MOMmmy walks in!! You’re so embarrassed and she is too! She’s sorry you had to find out this way that she’s a whore, and she awkwardly tells you that since you paid already and you’re both already there…. you both might as well go through with it anyways. She strips and teases you before sensually sucking your big cock. You stick it in, in missionary when she realizes SHE’S YOUR FIRST and taking your virginity. She praises you and encourages you sweetly. When she starts riding she starts getting more intense, dirty talking and riding hard. Mommy cums on your cock as she begs for your creampie (implied). But you paid to cum twice, so she strokes out the second and swallows it!!

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Sharing Daddy with My Bestie video from Madisyn Wood

Sharing Daddy with My Bestie After inviting my bestie over, daddy comes into the room and we get her to play with us! She's shy at first but she's my best friend! I suck daddy's dick and show her how, and she takes a turn. Then we take turns fucking his huge dick, I knew he would love her young tight body, it's so much like mine! [this was shot during cicada summer, listen to the preview]

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Desperate Degraded Mommy video from Madisyn Wood

Desperate Degraded Mommy Heavy Explicit Dirty Talk**** Your step-Mommy has been to a bunch of job interviews but I have come up with nothing, I need money desperately to make rent. You agree to give me the money if I play with myself and say nasty things... I do, I finger and rub my pussy about you fucking me, but then you actually want to do it! I agree IF you give me two months rent, more money for step-mommy. I get back into it as you fuck me, a little mortified at first that we're actually doing this. I play the part of your degrading nasty talking step-mommy and then you want to actually put it in my asshole! Again, more money and I agree. (Using my glass dildo as a stand-in I fuck my ass as if it's your cock in me.)

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Mommy Loves Your Tiny Dick video from Madisyn Wood

Mommy Loves Your Tiny Dick You got mommy a present! (for mothers day) you're so sweet, and it's some lingerie! I try it on for you and tell you to take out your itty bitty little cock. It's the kind of cock only a mommy could love. I tease in the outfit before rubbing myself over my thong and then eventually underneath, encouraging you to rub your tiny penis. I am sweetly humiliating you, pointing out how subpar it is and won't pleasure a real woman. Good thing you'll always have me. we cum together while i'm rubbing under my panties - fyi you never see me fully naked please watch the preview.

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Misogyny Student Learns to Behave video from Madisyn Wood

Misogyny Student Learns to Behave I'm a student in Miss Wood's Misogyny Class. And in this THREE PART video, I get better and better at pleasing you - my boyfriend. In the first part I'm awkward, it's after my first day. my bra and panties are boring. I give you a weird blowjob - i havent blown you in a month. And you give up and just ask to fuck me. it ends with me laying there "ready to go". Next, i'm doing better in my class and I am being more sexy. I blow you better, talk dirty this time. call myself a slut. and then I ride you to make you cum. Finally in part 3, I am the ultimate slut. I am just a cock sucking hole for you. 100% submissive. I degrade myself. gag hard. i am a fuck toy, guess the class really worked.

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Magic Spell to Grow my Small Tits: Choose Your Ending video from Madisyn Wood

Magic Spell to Grow my Small Tits: Choose Your Ending I got a spell to grow my small tits! But I need cum on them to make it work! You’re just my friend, I don’t have a partner to help me so I ask you to help. I get you to agree, but you say you can only get hard if you look at my boobs. I’m embarrassed, but I kiss you and you play with my small tits. Then I ride you and dirty talk begging you to pull out and cover my boobs BUT WAIT YOU CHOOSE WHAT HAPPENS NEXT!!! You can keep going and pull out and cover my tits orrrrrr decide that we should just keep fucking and you Creampie me (implied) instead in missionary (virtual sex).

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Rave Slut Daughter video from Madisyn Wood

Rave Slut Daughter I'm about to leave for my rave but you say my outfit is inappropriate. I'm a huge brat to you. We engage in a lot of conversation - you try to tell me how to behave with boys and I don't care. You 'check' my outfit and we engage in lots of upskirt teasing. Finally it's clear that you just want to fuck me. You fuck me for only **** 2 minutes*** before creampieing me! (10:30-12:30) I'm sooo mad. I get dressed and sass you before leaving for my rave, ugh gross

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Rave Slut Daughter PART 2 video from Madisyn Wood

Rave Slut Daughter PART 2 You're very critical of all my slutty outfits, so I decide to try some options on for you before I go out partying with my friends - last time I did this you creampied me so I throw that back in your face. I tease you and show off for you, but I still think you jerking to me is gross and weird, my step-daddy is such a pervert. I bet you wanna feel me up again and fuck me, too bad I have to go out! byeeeee (no sex, no penetration)

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Rave Slut Daughter PART 3 video from Madisyn Wood

Rave Slut Daughter PART 3 I'm back trying on outfits for daddy. This time it's a halloween rave and I try on another 3 outfits, teasing and showing off. I'm still a brat but I start to see the benefits of letting daddy get off to me. this time i bargain for cab/uber money and even purposefully not look while he does whatever he wants behind me. I still think you're a pervert but I guess I'm getting used to it, gross but kinda fun getting attention from daddy .

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Impregnate ME Instead video from Madisyn Wood

Impregnate ME Instead I heard you and your wife are going to start "trying" soon... but I've had my eyes on you for a while. I want you to get me pregnant instead! I strip and seduce you, convincing you to breed me instead. Then I suck your cock, ride you, take it in doggy, and then ride you nice and hard again until I cum and then make you creampie my pussy!

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Sex Ed video from Madisyn Wood

Sex Ed We're classmates in a college class on History of Sex. It's an easy A, except for the last day of class, two students are chosen at random to have sex while the rest of the class watches and writes a report. We're about to have sex when you tell me to get hard I need to take off my bra, NO WAY!! **I'm embarrassed of my small tits!!** I tell you to "cover them" the whole time while we fuck and that way no one has to see and we'll still pass the class, hopefully... |. VERY LITTLE PENETRATION, ONLY AT END FOR CREAMPIE Tags: virutal sex, missionary, POV , riding , pigtails, brunette, college girl , dirty talk , roelplay, classmates, kissing , cumshot

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Dirty Mind video from Madisyn Wood

Dirty Mind You're my roommate, and I'm trying to talk to you but I notice you aren't listening.. wait, are you imagining me NAKED?? You start to imagine all kinds of dirty things with me, unable to break out of your day dream. I'm so embarrassed, but maybe it starts to turn me on, too! I start to get into it too, and soon I think it's super hot watching you thinking of fucking me.

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18th Birthday Virgin's Creampie video from Madisyn Wood

18th Birthday Virgin's Creampie I’m turning 18! You’re my best friend and I was hoping for my 18th you’d finally give me your cock! But you don’t… and I guilt/convince you into playing with me since I’m a virgin and I’ve been saving myself for you. You’d be the first person to ever fuck me. You play with my boobs, then finger my pussy, and then I ride you. My tight virgin pussy feels so good for you, when you start fucking my missionary I tell you the real present I want is a CREAMPIE!! (missionary beginning is virtual sex pov, then rest is dildo visible pov through creampie) You fill me as I cum and it’s so, so much cum. Best present ever

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The Dumbest Blowjob Girl video from Madisyn Wood

The Dumbest Blowjob Girl I know I'm dumb, I'm the dumbest whore you've ever met. I know my purpose now, just to offer my mouth for you and anyone else. I dirty talk the entire video, stripping and teasing you with my body while I tell you everything I love about sucking cock and how stupid I am

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I Get Off to Being Dumb video from Madisyn Wood

I Get Off to Being Dumb Tell me how dumb and stupid I am. I confess to you when I realized how much hearing it gets me off. Telling you so many dirty things, I tell you about when three guys blew their cum on me and from then now getting used, getting cummed on and hearing men talk down to me turns me on so much. I'm addicted to cum and having my throat used. Stupid blowjob slut, cum dumpster, dumb whore. That's my purpose. For the first 20 minutes I talk and strip and show off my body, at the very end I rub my clit and cum.

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Blowjobs Are My Purpose video from Madisyn Wood

Blowjobs Are My Purpose I'm as stupid as they come, as dumb as it gets. And I love when you tell me, love when you humiliate me and show me how much of a dumb bitch I am. Especially while I suck your cock, my mouth is a useless hole for you. I get wet when you fuck my mouth and call me stupid. I strip and show off my body while I talk and at the end rub myself to orgasm. ----- [[ If you like my videos "I Get Off to Being Dumb" and "The Dumbest Blowjob Girl" then you'll like this, very similar!! ]]

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You Belong To Mommy video from Madisyn Wood

You Belong To Mommy You and Mommy used to fuck around, but now you have a new dumb ugly girlfriend and you've been ignoring your mommy. I've been thinking of you every night while I touch myself, and I heard you having phone sex with your girlfriend through the wall. I've had enough, dump her and be with me. You protest that you're with her, but Mommy knows best. I know what you need. I jerk your cock getting it hard until you fall in line, then I suck it the way you need, you're step-mommy's fuck toy and you love it. I ride you until we both cum and beg you to fill step-mommy's pussy. (implied creampie). See? You don't need anyone else besides Mommy.

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Barely Legal Pussy video from Madisyn Wood

Barely Legal Pussy I start by stripping and showing you my tight holes while you beat your dick to me, talking about how I'm only 18 and you're so much older and how much you craveeee teen pussy like mine. then we have sex (VIRTUAL SEX) cowgirl and missionary while I taunt you about how you're cheating on your wife and you're such a perv for girls like me and you want to dump your old man cum inside me. I'm a bit of a brat and lightly humiliate you for being old.

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Nurse & Doctor Cum Extraction video from Madisyn Wood

Nurse & Doctor Cum Extraction Nurse Madi greets you and gets you all set up and comfortable before Dr.Wood comes in. Dr.Wood goes through the questionnaire about your sexual preferences while Nurse Madi strokes and sucks your growing cock. The Dr has some time so she helps with the first extraction and you cum in her mouth, overflowing it with cum while the Nurse touches herself to the side. The Doctor agrees to help more, taking your cock in missionary while the nurse teases you, they both dirty talk. Then the nurse goes into doggy until you bust your load all over her ass. But, you still have more cum!!! The nurse rides you cowgirl and then reverse because she knows you love her ass, even though we aren't supposed to be creampied... she makes an exception and lets you fill her tight pussy anyways. See you next time at the clinic!

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Mommy's Anal Confession video from Madisyn Wood

Mommy's Anal Confession ***NO ANAL PENETRATION SHOWN, VIRTUAL ONLY *** I'm sitting down with you (my husband) and I decide I have to come clean. I talk naturally and unrushed. I tell the story of how our step-SON blackmailed me for my asshole. I had to do it. And he has been fucking me anally ever since behind your back. He degrades me, makes me do ass to mouth. And I hated it at first but now I can't stop. This confessional on the couch is interspersed with short "flashbacks" to times when he fucked me ALL VIRTUAL SEX / CLOSE UP FACE. I love it now. I start stripping while I confess about 6 minutes in. And then at the end I see you're hard hearing me talk about this so I spread my stretched out used asshole and encourage you to beat off to it and cum for me. I think you actually like that I'm getting my s***hole fucked by him now. [[ AGAIN, STRONG ANAL LANGUAGE USED ]]

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The Day After Graduation video from Madisyn Wood

The Day After Graduation It's the day after graduation. I come back to visit you, my fav teacher. I'm BL (18, just graduated high school) and use my ID card to get in. No one's around I decide I want you. it's okay now that i'm not your student anymore. You're kind of unsure because you've crossed a line like this before but I've gotten it in my head that I was your favorite and I know ultimately you won't say no to a pretty fresh girl like me. I suck your cock and then I demand to fuck you. I ride you to make you fill me, I've never been creampied before (implied cum). Definitely bratty tone "I get what I want" vibe. Reverse ride, then frontal squat riding. the fact that i am 18 is a theme but not the only thing talked about, just a neutral fyi.

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Demeaned by my Cheer Team video from Madisyn Wood

Demeaned by my Cheer Team [[ IF YOU LIKE MY OTHER VERBAL HUMILIATION VIDS YOU WILL PROBABLY LIKE THIS TWIST OF DISCUSSING BEING DEGRADED BY WOMEN ]] I talk very dirty throughout as I strip and pose. I'm the cheer team at my college and the girls there do nothing but humiliate me and use me. They are all women, they degrade me verbally and physically. They call me names, squirt down my throat, make me lick their dirty sweaty holes. They don't shower on purpose just to get to me. They spread rumors to the football players, they make me look like an idiot. I really lean into the smell fetish in this video, armpits, feet, cunts, etc. Anyways, Some of it I like, some of it is unbearable but I'm in too deep. I just have to tell you everything, but quit??? I could never.

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Misogyny Class 101 video from Madisyn Wood

Misogyny Class 101 this is the first chapter of miss wood's misogyny class. She breaks things down pretty clear for all women in her class: how women should treat a man, how women are inferior to men, his pleasure comes before anything, all women are dumb whores, never waste a man's time by making yourself cum, all your holes belong to all men. She gives personal examples and calls out classmates. She isn't afraid to degrade students and herself, including the smell of their fucking cunts. There's no one better versed in misogyny than miss wood, this is just chapter one, there's so much more to learn.

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Misogyny class 102 video from Madisyn Wood

Misogyny class 102 class is back and even better, i'm excited to keep molding these dirty bitches into good little whores. This time we start with flashcards! I degrade them, I'm catty. then I strip. It's time to practice some positions so we can please men. i critique my class on how to make men cum, their worthless cunts need a lot of work. Then for the last 4 minutes, I show some porn (me), three examples for their homework (the female students are supposed to show their at home clips in front of the whole class for feedback next class lol). I degrade myself technically by pointing out what i'm doing wrong on these video examples

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