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Alan Carly is one very hot guy, and just perfect to be turned into a personal slave. That is exactly what his girl has in mind as he has him blindfolded, with his wrists shackled over his head. He wears only some see-thru underwear and some more shacles on his ankles. The girl approaches Alan who insists that he wants to be released, but his request is denied. The girl starts to torment him, trying to make him scream, but Alan resists, even when the whip is used on him. She whips his body and tries to make him scream, but still he resists. The girl then takes some clips and applies them to Alan's nipples. He certainly feels the pain from the clamps and the girl goes further, putting a collar around his neck. Then she pulls down Alan's underwear and start to slap at his cock and balls, before taking the whip to him again. She pulls the pubic hair too, making Alan squirm and wriggle. Then she has another idea, using clothes pins to attach to his cock and his valls. After that she puts a gag into his mouth as well. As she removes the clothes pins Alan feel the pain with each one. The wrist shackles are removed and Alan is pushed to the ground, where he is made to beg, like a dog. It seems that he is beginning to learn what he will have to do to please his mistress. A dog bowl is presented next with Alan made to drink from it. Then he is told to lay down and he goes down on his elbows, presenting his hot ass. The girl whips the ass and then inspects it closely, rubbing a toy against the hole. After whipping some more she turns the whip round, and shoves the toy end into that hot ass. With his ass full Alan is led around on his leash. He then gets some relief as he is allowed to stand, but is shackled again as the girl starts to suck on his cock. That dick quickly gets very hard indeed as she works on it. But she wont let him cum yet. First she wants to fuck his ass with her strapon and Alan lays on his back as she plows his ass. The rubber cock rams into his hole, working it good before changing position. Alan wanks his cock hard and fast as the dick continues to fuck his hole. He keeps wanking until his shoots his creamy load, with the girl still fucking him.
3 years ago
118971
4:00
IMMERSION THERAPY: A JAY TAYLOR STORY WOMAN AGREES TO INTENSIVE DP THERAPY SESSION TO CURE PHOBIAS Scene opens on Erin (Jay Taylor), a 25-year-old woman, as she sits on a couch immersed in herself. She's dressed in loose loungewear, her body language nervous and uncomfortable, while her therapist, Daniella (Angela White), talks to her. But Erin isn't listening. She's more engrossed in her own thoughts, her foot tapping, her fingers scratching an itch on her arm. Daniella addresses her more clearly, 'Erin?' The woman snaps to attention, but still remains closed off. The therapist continues, 'I really need you to pay attention and work with me today. If I'm being honest, I'm running out of ideas on how to continue. Now, did you do the homework I assigned last session?' Erin frowns. CUT to a flashback. Erin stands in front of a mirror and slowly undresses. Her naked body elicits no response from her. While she dutifully starts to run her hands over herself, she looks away as though trying to pretend something else more interesting is happening on the wall. She clumsily squeezes her own breasts, but when she tries to explore between her legs she recoils as if disgusted. CUT back to the therapist's office. Erin slowly responds to the question, 'Um... I went as far as I could.' Daniella is almost at a loss, and though her words are measured, she is frustrated, 'Okay ... What is it about your own body that repulses you?' Erin stiffens, she doesn't want to answer this question again. 'It's not MY body. It's anyone's body! They're so messy, so bestial. The way they look, feel, smell, sound...' Daniella interrupts her almost absent-mindedly, 'And taste? Erin, this is becoming almost beyond what I can help you with in my practice. I have one more technique we could try, but it is going to be more intensive than our other methods so far. So, I would need you to commit wholeheartedly.' Daniella's offer intrigues Erin. She sits up, focused. 'I don't want to go to anyone else. I'm willing to do whatever you think we need to do.' Daniella smiles, 'Excellent. I'll prepare the consent forms.' CUT TO TITLE PLATE Erin sits on the floor of the therapist's office, the desk pushed back, and a selection of pillows and blankets now artfully arranged around her. She seems curious but apprehensive, clutching the consent form in her hand as Daniella finishes laying out the space. 'Excellent, this should give us the comfortable setting we require,' she says, motioning to Erin to hand over the form. The patient does so, and Daniella scans it to confirm all the fields are complete. 'Good,' She says, putting it on the desk. 'Now, I need you to trust me. You want to get better, yes?' Erin nods, and Daniella continues, 'Good. Why don't we get a little more comfortable? Take your sweater off, and I'll do the same.' Erin hesitates for just a moment, before both women remove an outer layer of clothing. This leaves Erin in a tank top and Daniella in a bra. Erin tries not to stare at her breasts. She feels incredibly anxious but Daniella smiles, 'Wonderful. Look at how far you've come already. Now, just mirror what I do.' She starts caressing her own body, starting benignly with her arms and waist, then moving to her breasts. Every time Erin pauses or panics, she encourages her. They continue touching themselves, first their legs, then between them. Erin finally relaxes into this and they masturbate without touching each other. When they begin getting close to climax, a young man (Seth Gamble) enters the room silently and slips behind Daniella to fondle her breasts. Erin is startled, but Daniella quickly calms her, 'Don't mind him! He's just my assistant. An extra pair of hands. Focus on me!' Erin's eyes lock back onto hers and she continues cautiously masturbating. After a few moments of this, Daniella asks Erin to undress from the waist down. Erin complies and slips her leggings and panties off. She resumes masturbating as Daniella bends over and the man starts to go down on Daniella from behind. Erin is completely focused on Daniella and continues to masturbate. Erin can imagine what is happening to her therapist, but she can't see it, so Daniella describes it to her ... building up to asking Erin if she wants to know what it feels like too. Erin nervously says yes. Daniella gracefully crawls over to Erin. She spreads Erin's legs, eating her pussy as Erin shudders with pleasure. At the same time, the man begins to fuck Daniella from behind. Soon, all three of them are moaning with ecstasy when another young man (Codey Steele) enters. He walks up to Erin and asks if he can remove her top. Daniella reassures her again that he is another assistant, here to support them during their session. She should continue to focus on her and relax. Erin slowly says yes. The second assistant removes Erin's top, squeezing her tits. The first assistant slides his cock out of Daniella and she begins to suck it. When the second assistant walks around to face Erin, Daniella again instructs Erin to mirror her. Erin starts to suck the second assistant's cock, and Daniella talks her through it, getting her in touch with her carnal side, but their focus remains on each other. As Erin continues to suck the second assistant's cock, Daniella gets on top of her assistant and begins riding him as she faces Erin. She coaxes Erin down to get on all fours, close enough where the two women can almost kiss. The second assistant gets behind Erin and slides his dick into her. The second assistant fucks Erin as she squeals loudly. But unbeknownst to Erin, his dick isn't going to be the only cock penetrating her body today. Is Erin ready for the FINAL phase of her immersion therapy?
4 years ago
1511
6:14
Welcome to the second installment of Kink's School of Submission, this time featuring Kristen Scott. S.O.S. is four days of mental and physical torment and challenges. It's not for just any girl. Each one has petitioned to be here, and is then hand-selected by The Pope. The experience is as real as you will ever see. There is no acting of any kind, and the raw emotion of exactly what she is experiencing is something rarely captured on video. The intent of School of Submission is to show this, and to pull back the curtain to show you see the deepest and most personal of experiences of this performer. We begin with an in depth interview between Kristen and The Pope. This is a time for discovery for both of them, and it helps The Pope set a path for Kristen over the next 4 days. Kristen is found with a small grin, staring into a mirror in the dungeon, as if she were very pleased with where she is and what is about to happen. The Pope enters and immediately begins her journey by instructing her on basic expectations that he has for her. She is told to undress while being asked questions and expected to stay focused. As he inspects her body he pokes and prods her to find out what makes her purr, as well as squeal. Kristen is now very sexually charged and it is becoming more difficult for her to stay focused. This is his intent, and she will surely pay for her slip. The Pope slowly tears away layer after layer of Kristen's walls with hopes of getting deep inside of her mind and helping her grow from the experience. At this point she is putty in his hands, yet he has only just started. Her orgasms are held at bay until he sees fit to allow her any, and when he does she can barely stand. Every second is sexually-charged, from the tease and denial to the brutal caning, and everything in between.
4 years ago
60573
4:00
A chain leash is secured with a small padlock to the ornate metal headboard of a bed. This is connected to a collar, fastened around the neck of Cristin, a brown-eyed brunette from Ukraine. Runway-model tall, with a body and face to match, she is dressed in burgundy-lace lingerie, a sheer, burgundy robe and leather wrist cuffs. Her hair is loose and her face is free of make-up. She runs her hands up and down the chain, confirming that there is no possibility of escape. Kneeling on the bed, she discards the robe and strokes herself through her lingerie. She removes her bra to reveal small, perfect natural breasts. Then she takes off her panties to expose her shaved pussy. Nipple clamps are attached to the cuffs with fine chains, and Cristin clips these onto her stiff nubs, smiling as she feels them pinch. Sprawling back on the bed, she begins to tease her slit with neat, unpainted fingertips, stroking and stretching her lips and circling her clit. She moans with pleasure as her juices begin to flow, and splays her long, slender legs wide open. Next, she kneels on the sheets doggy-style, flaunting her bare feet and the tight pucker of her asshole as she reaches down in between her thighs to continue frigging her swollen pink. As she rocks back and forth on the bed, her cries become more urgent and her face twists in pleasure. She sits on the bed again and her fingers spread her juices all over her hairless crotch and, with the nipple clamps removed, her free hand tugs and squeezes her breasts. As she approaches orgasm, she clings to the chain leash at her throat, then caresses her breasts again as she takes herself over the brink. Virtually sobbing with pleasure she cums, spasms shaking her entire body. As the picture fades we see the padlock key lying on the covers near the corner of the bed Cristin could free herself at any time but instead, she chooses to ignore it completely...
4 years ago
2778
2:01
Sybil and Matty have been spending their time indoors together, and their relationship has deepened as a result. During one nice afternoon, Matty makes Sybil a cup of tea, and brings it to her. It's another kind gesture amidst a weekend of demonstrations of love. Sybil looks deeply into Matty's eyes and kisses him with passion, then unzips his pants so she can stroke his big cock. As Sybil teases Matty's dick, he caresses her perky tits, then she slides forward to give him a wet blowjob. In the heat of passion, Matty pushes Sybil back and tears off her shorts, then sticks his tongue between her legs to lick her pussy. Matty and Sibyl make sensual love, going from missionary, to doggystyle, and then to cowgirl. After multiple orgasms, Sybil lies between Matty's legs, and strokes his cock until he cums!
3 years ago
3571
7:00
THE PERFECT SON Teen Talked into Sex with Emotionally Unstable Mother and Son The scene opens on Jessy and Adam, two 19-year-old college sweethearts, as they sit awkwardly at a dining room table. The couple, who met at school, have been dating for several months and tonight Adam has brought the girl home to meet his step-mother, Mrs. Curtin. Jessy is an outspoken, liberal arts student, a sharp contrast from Adam, who dresses conservatively, studies economics, and still lives at home. But the two are in love and, despite Adam's reservations, Jessy has been the one pushing to meet his family. She is very serious about him and wants to take things to the next level. So, under the table, she squeezes his hand and assures him that everything will be ok. When Mrs. Curtin enters the room, carrying a tray of food, Adam drops his girlfriend's hand and stands up to help his mother. She is dressed immaculately and seems friendly but fragile -- there is something about the way she carries herself that is almost frantic. While her son dutifully helps her set the food down, Mrs. Curtin smiles and tells Jessy about what a good man Adam has become. Ever since she came into his life when he was a young boy, he has been just like a real son to her -- a perfect son. Jessy, bright and bubbly, tells Mrs. Curtin in turn all about how she met Adam and how much she likes him. His mother smiles and feigns interest, but you can tell she is very preoccupied with her boy. The moment he starts to move back over to Jessy's side, she comes up with some reason for him to come back to her. Adam seems aware of this and awkwardly tries to diffuse the situation but, after a certain point, Jessy begins to feel uneasy. She excuses herself to the bathroom. Once alone, Jessy closes the bathroom door and presses herself against it. She stares off into space ... something is very strange about Adam's mother! Jessy washes her hands and stares at herself in the bathroom mirror before returning to the dining room. She finds Adam sitting alone. He seems nervous and agitated. She asks him where his mother went but, before he can really reply, Jessy starts to candidly talk about how weird dinner has been. She can't believe how overbearing and clingy Mrs. Curtin is, especially since he is a grown man. Why is she treating him like a coddled child and why does he have to drop everything to care of her? It must be so annoying to still live at home; no wonder he is always so serious! As she laughs, she nudges closer to Adam to kiss him when she looks down and notices that Mrs. Curtin is under the table sucking her step- son's dick! Jessy jumps back in disgust and, after cursing at her boyfriend and his mother for being sick and disgusting, she storms out of the house. As she runs to her car and starts struggling to open the door, Adam follows apologetically after her. He begs her to stop and listen to him, he can explain everything. It's not what it looks like. It's not cheating and he doesn't consider it sex ... well not exactly .... he just has to take care of his mom this way. When Jessy accuses him of being a pervert, he reminds her that Mrs. Curtin isn't actually his biological relative ... she's just been his mom for most of his life. His father was horribly abusive and made their life a living hell so, ever since they split up, Adam has had to step in and take care of her. Mrs. Curtin is emotionally fragile and will spiral into panic attacks if he doesn't do things with her sometimes, especially when she is feeling threatened. It seems unorthodox but it is just how his family functions now. While Jessy cries and struggles to understand how her boyfriend could keep such a secret, Adam keeps trying to reassure her. 'I promise you I don't consider it sex,' he tells her. 'I just consider it being a good son. I'm helpingher keep calm. Nothing else has ever worked. Please, don't reject me because of this. I love you and I want to be with you. I swear!' Jessy asks if he will stop. Adam tells her he wants to stop and that's why he invited her over ... she is the first girl he's ever brought home. He begs her to just come inside and, together, they can explain to his mother how in love they are and, surely, she will understand that it's time to let him go. The frazzled Jessy finally agrees and follows him back inside the house. Mrs. Curtin is waiting silently in the living room when the couple arrive. Jessy is standoffish and Adam must plead with her to get her to sit down beside him. Arms crossed, she coldly tells him to start talking. Adam turns to his mom and meekly tells her that their affair will need to stop. As she hears this, Mrs. Curtin starts to cry and curl up in a ball on the couch. Adam rushes to her side to comfort her, while Jessy stands up in protest. She tells him that she's leaving right now if he doesn't make a choice. Adam looks desperate and conflicted. Through her tears, Mrs. Curtin makes a proposal: If her perfect son is really going to choose Jessy over her, she needs to at least understand why. She needs to see what Jessy has that makes her so special. She needs to watch them being together!THE PERFECT SON Teen Talked into Sex with Emotionally Unstable Mother and Son The scene opens on Jessy and Adam, two 19-year-old college sweethearts, as they sit awkwardly at a dining room table. The couple, who met at school, have been dating for several months and tonight Adam has brought the girl home to meet his step-mother, Mrs. Curtin. Jessy is an outspoken, liberal arts student, a sharp contrast from Adam, who dresses conservatively, studies economics, and still lives at home. But the two are in love and, despite Adam's reservations, Jessy has been the one pushing to meet his family. She is very serious about him and wants to take things to the next level. So, under the table, she squeezes his hand and assures him that everything will be ok. When Mrs. Curtin enters the room, carrying a tray of food, Adam drops his girlfriend's hand and stands up to help his mother. She is dressed immaculately and seems friendly but fragile -- there is something about the way she carries herself that is almost frantic. While her son dutifully helps her set the food down, Mrs. Curtin smiles and tells Jessy about what a good man Adam has become. Ever since she came into his life when he was a young boy, he has been just like a real son to her -- a perfect son. Jessy, bright and bubbly, tells Mrs. Curtin in turn all about how she met Adam and how much she likes him. His mother smiles and feigns interest, but you can tell she is very preoccupied with her boy. The moment he starts to move back over to Jessy's side, she comes up with some reason for him to come back to her. Adam seems aware of this and awkwardly tries to diffuse the situation but, after a certain point, Jessy begins to feel uneasy. She excuses herself to the bathroom. Once alone, Jessy closes the bathroom door and presses herself against it. She stares off into space ... something is very strange about Adam's mother! Jessy washes her hands and stares at herself in the bathroom mirror before returning to the dining room. She finds Adam sitting alone. He seems nervous and agitated. She asks him where his mother went but, before he can really reply, Jessy starts to candidly talk about how weird dinner has been. She can't believe how overbearing and clingy Mrs. Curtin is, especially since he is a grown man. Why is she treating him like a coddled child and why does he have to drop everything to care of her? It must be so annoying to still live at home; no wonder he is always so serious! As she laughs, she nudges closer to Adam to kiss him when she looks down and notices that Mrs. Curtin is under the table sucking her step- son's dick! Jessy jumps back in disgust and, after cursing at her boyfriend and his mother for being sick and disgusting, she storms out of the house. As she runs to her car and starts struggling to open the door, Adam follows apologetically after her. He begs her to stop and listen to him, he can explain everything. It's not what it looks like. It's not cheating and he doesn't consider it sex ... well not exactly .... he just has to take care of his mom this way. When Jessy accuses him of being a pervert, he reminds her that Mrs. Curtin isn't actually his biological relative ... she's just been his mom for most of his life. His father was horribly abusive and made their life a living hell so, ever since they split up, Adam has had to step in and take care of her. Mrs. Curtin is emotionally fragile and will spiral into panic attacks if he doesn't do things with her sometimes, especially when she is feeling threatened. It seems unorthodox but it is just how his family functions now. While Jessy cries and struggles to understand how her boyfriend could keep such a secret, Adam keeps trying to reassure her. 'I promise you I don't consider it sex,' he tells her. 'I just consider it being a good son. I'm helpingher keep calm. Nothing else has ever worked. Please, don't reject me because of this. I love you and I want to be with you. I swear!' Jessy asks if he will stop. Adam tells her he wants to stop and that's why he invited her over ... she is the first girl he's ever brought home. He begs her to just come inside and, together, they can explain to his mother how in love they are and, surely, she will understand that it's time to let him go. The frazzled Jessy finally agrees and follows him back inside the house. Mrs. Curtin is waiting silently in the living room when the couple arrive. Jessy is standoffish and Adam must plead with her to get her to sit down beside him. Arms crossed, she coldly tells him to start talking. Adam turns to his mom and meekly tells her that their affair will need to stop. As she hears this, Mrs. Curtin starts to cry and curl up in a ball on the couch. Adam rushes to her side to comfort her, while Jessy stands up in protest. She tells him that she's leaving right now if he doesn't make a choice. Adam looks desperate and conflicted. Through her tears, Mrs. Curtin makes a proposal: If her perfect son is really going to choose Jessy over her, she needs to at least understand why. She needs to see what Jessy has that makes her so special. She needs to watch them being together!
4 years ago
1646
6:14
Sit back and relax, because your beautiful Cybergirl of the Month, Olivia Preston is tugging on heartstrings as she gets ready to play you the sweetest of melodies in this new pictorial. She's classic and incredibly elegant on set with photographer, Cassandra Keyes as she poses in the most sultry ways atop a baby grand piano. This set was so classy, it was by windows and the curtains were coming up over the piano and over me as if we had trained them to do that, Olivia says with a bright and sweet smile, It was perfect. She's changed up her look a little in this one with her hair pulled back and big brown eyes staringly longingly into Cassandra's lens, it's hard to not get swept away into this musical daydream. Gaze as she slowly removes her black dress to reveal lace lingerie and her perfectly curvy figure. I have a very womanly body, she mentions. I have proportionate boobs I like them a lot, she says confidently as she cups her breasts. But I really like my hips the most. I have that skinny girl hourglass curve. I think it's mature and has its own kind of sex appeal. I think it helps me on photo shoots. We couldn't agree more; Olivia has been modeling for four years and has gained much popularity and success. I've been modeling nude since my third Playboy shoot. I kind of just naturally undress; I prefer being nude, I think I look better, and I'm really comfortable in my skin, she says. For Olivia, posing nude is a beautiful art form, and she's ecstatic to be doing it for a living. The lines and the curves of a feminine body are just so much better if there are no waistbands or bra-straps cutting that eye line. I think it's beautiful and classy. Get to know all the lines and curves of this beyond gorgeous Cybergirl of the Month, Olivia Preston, right here only on Playboy Plus.
4 years ago
1706
5:00
As soon as Chloe Lamour got in the Mean Orange Machine, I knew it would be a challenge not to crash the car. Her huge tits were practically bursting out of her pink tanktop, so I knew I really had to concentrate on keeping my eyes on the road. I went through the basics of car safety with Chloe, showing her the pedals, mirrors, and seat, and then we started driving. When I had to do an emergency stop, I shot my arm out to brace her by instinct, and my hand found its way on her boob! She had to remind me to remove my hand, but then asked me if I liked her tits. Of course I did, so she asked what I would give her if she let me play with them. I offered free lessons, and for ten, she let me motorboat her. For 15, she let me have her shaved pussy, then for 20 she sucked my cock! Finally, I asked her to fuck: we settled on 30 lessons, she rode my dick, and then I came all over those huge tits!
4 years ago
5466
6:59
After renting a cabin in the woods with some friends, Marc spends the weekend arguing with his wife, and after she spurns his attempts at reconciliation, he leaves to spend the night alone. In the morning, Marc sees Talia Mint in the kitchen, and the friends get to chatting. Talia tells Marc how sore her neck and shoulders are, and Marc offers to take her to the hot tub to give her a massage. Walking to the tub, Marc sits on the edge and Talia sits in the water. Talia removes her bikini top as Marc rubs her neck and shoulders, and then he reaches forward and massages her breasts. Talia tells Marc she has some tightness in between her legs, so Marc plays with her pussy. Turned on, Talia gives Marc a blowjob, then pulls her bikini bottoms to the side to sit on his thick dick. Talia fucks Marc in and out of the hot tub and he cums on the hot brunette's face...just as his wife walks in!
4 years ago
1736
6:59
I have a different take on massage, said Angelique DuBois, a first-timer at 60PlusMILFs and a professional masseuse in her personal life. "I think it's something very sexy and sensual. I love to work with my hands. I love the whole energy exchange. I love the feel of the skin and doing things with your hands to make people feel amazing." Angelique gets to demonstrate her skills on Rocky, a guy who's 37 years her junior. Rocky is 100% naked, no towel at all, which is not the way her professional massages usually start. Before long, Angelique is massaging his ass, which is the kind of massage we'd like to get from Angelique, then she's getting naked and rubbing her tits along his back, which just has to cost extra, then she's sucking his cock, which we know costs extra. And then she lets him fuck her, which knocks that price point right out of the park. Of course, you should always give your masseuse a tip after an enjoyable session. Angelique's tip is cum all over her face. Angelique was 60 when this scene was shot and turned 61 a few days later. She was born in South Africa and lives in Southern California, where she's a divorced mother of three and a grandmother. She can do magical things with her hands and her mouth. And her pussy. You don't find this kind of service in every massage parlor.
3 years ago
1396
5:24
