Tag Archives: Princess Skylar

Clubstiletto – Princess Skylar – Bathe Me Daddy

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Princess Skylar has blackmailed her step-dad into becoming her slave. After catching him in the act of violating her worn panties, she has video evidence to show Mom, and he has no choice but to agree to anything she wants. Today, she needs daddy to bathe her. She makes him wear a hood with no eyeholes because he doesn’t deserve to see her lush young body. While being bathed, she tells him she’s so happy she found him sniffing her panties and how nice it is knowing he has to do everything she says. She tells him he will be greeting her boyfriends at the door from now on, taking their jackets, serving their drinks, “and when they leave, you will shake their hands and say ‘thank you for fucking my daughter’”. Poor daddy groans but knows he has no choice but to do whatever she demands. To humiliate him further, she says “In fact, you can tell my boyfriend that Mom, your wife, is pretty hot too, and that next time he comes over, he can fuck her as well”. She says that maybe Mom, she, and the young stud will have a threesome. She makes him tell her he likes the idea and has him say “I’m looking forward to your boyfriends fucking Mom”. Poor dad! He’s dying but does as he’s told. Skylar turns on the jets and tells daddy to wash her entire body while she relaxes. Daddy goes over her breasts, ass, and pussy with the washcloth, now that he’s nothing but her helpless slave.

Mistress: Princess Skylar
Category: Blackmail Fantasy, Taboo, Bathtub Fetish, Princess, Humiliation, Family Fantasy
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Clubstiletto – I’m Thinking of My Black Studs Cock, hubby

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Princess Skylar can’t get enough sex, sometimes she’s so horny that she needs to get fucked from her cuck before her hung boyfriend gets there. Her cuck is not good enough or endowed enough to use his real cock of course so she locks him to the cage and fits him with a big mouth dildo that will get her off until her stud arrives. She lays down and touches herself, teasing him with her pussy, then tells him to stick it in. The slave gets a nice steady rhythm going and she touches her clit and thinks of her black stud. “What would your mother say if she saw me deliver a black bay?”, she asks him. “You’ll be home taking care of the little one while I’m out on the town getting fucked and maybe pregnant again, she says with a laugh… and a moan. She tells him that if he eats her out good enough after he cums in her she might not get pregnant and adds, “When you fuck me with the dildo, I like to imagine my black boyfriends fucking me and making you watch, each one fucking the out of me. Then they’ll watch you suck out all their cum.” She is getting so aroused and tells him to fuck faster, as he goes faster, she moans harder, starts to thrash until she has a mind blowing orgasm. Then there’s a knock on the door.

Mistress: Princess Skylar
Category: Cuckolding, Bbw, Dildo Fucking, Black & White, Cuckold
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Clubstiletto – Comfortable to sit on and cleans Boots too

Filed under Face and Body Sitting
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The Femdom world is both exciting and natural. In this completely unscripted clip Mistress Skylar introduces Jasmine to her girlfriend and novice Domme Tawny. They are sitting on a comfortable and practical human couch openly discussing the many pros and cons of slaves. The best furniture is versatile enough to keep their asses warm and also cleans shoes. Training low IQ slaves can be a lot of work but entertaining as well. Every slave has specific talents like taking beatings, cleaning cum, serving as domestic maids. Human toilet is probably the most natural. Just three Dommes sitting around chatting!

Mistress: MissJasmine, Princess Skylar
Category: Human Furniture, Humiliation, Double Domination, Toilet Fetish, Shoe Fetish, Female Domination
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Clubstiletto – Miss Jasmine, Princess Skylar – It’s a Thing Not a Person

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Princess Skylar and Miss Jasmine invite a new Domme in training, Miss Tawney over for a drink. They are all wearing gorgeous boots and put a human carpet to use. His cock and balls are tied and they each take turns yanking on the rope. Jasmine loves working out her arms this way. Mistress Skylar confesses that she has used the slave as a cuckold before. The 3 of them discuss the ins and outs of slave training and how every woman needs about 6 slaves for different uses. Slaves are tiered and the lowest, most stupid ones end up on the floor licking dirty heels and boots.

Mistress: Miss Jasmine, Princess Skylar
Category: Boot Domination, Boot Fetish, Humiliation, Double Domination, Human Furniture, Cuckolding
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Clubstiletto – Princess Skylar – Lick Then Fuck My Feet, Brother

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Skylar gets home after soaking up the heat outside and her brother is there on his knees, blindfolded, with arms bound behind his back. She reminds him how as kids he used to bully her but now that she recently found him sniffing her panties she is in control, or she will be telling m0m. She makes him suck her heels and says later it might be her boyfriends cock so he better do it well. Watch as Skylar makes him worship her feet and toes, then humiliates him by ordering him to stick his cock between her feet and fuck them because it’s as close as he’ll ever get to pussy again. Includes foot worship, cock kicking, verbal humiliation, tease and denial. Great family fantasy scene!

Mistress: Princess Skylar
Category: Footjobs, Foot Domination, Taboo, Foot Worship
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Clubstiletto – Princess Skylar – Go Ahead and Jump

Filed under Trample/Trampling
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Skylar has just got home from military training, she wants more advanced training to deal with evil doers in the world, namely the stupid slaves that long to serve her. After being screamed at all day she decides to take it out on her human carpet. The thing you will notice most in this clip is that Skylar does not really care where she steps on the slave, on several occasions the corner of her heels dig deeply into the ribs of the slave and the pain is so severe on one occasion that he instinctively shifts and almost throws her off. She severely admonishes him and decides to jump on him as punishment. Boot licking, squats, ball crushing, jumping, hand standing, nipple twisting, and walking all over his legs, stomach and chest, this slave is well worked over and may be happy when she finally tells him to get up and crawl to his dark room where he will be sequestered for the next 24 hours.

Mistress: Princess Skylar
Category: Trampling, Military, Bbw, Skylar, Trample
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Clubstiletto – Princess Skylar – This Big Ass of Mine

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The scene opens with young pretty and fleshy Princess Skylar talking to you, explaining that a slave must understand he gives up all control to his Mistress. “You even give up the right to breath.”, she says. It’s in her control and you can see by the slave under her ass that she plans to make him kick for air as he is already doing so. To add to his anxiety, she then starts to tickle his stomach which really gets him kicking, likely using his last molecule of air in the process. Skylar looks super sexy in her pink baby doll and you’ll notice the slaves arms are bound behind him to insure he is not going to push her away when in a state of panic. After a full minute she stands up and the slave gasps for air but before he can fill his lungs again, her big beautiful ass has again smothered him into silence. She loves seeing how the tickling makes him kick and continues to do it through the scene. She bounces up and down allowing only a fraction of a second each time to get air before again sitting down. To keep the slave off balance she throws him a curve and after another tickle gives him a nice little swat in the nuts. This slave is very sensitive in this area, not at all into ball busting, so the slaps really make him jump, but with his head cemented under Skylar’s big ass, he’s not going anywhere, lol. After all the tickling and ball slapping she sort of forgets he has to breath and when she does finally get up again, he gasps desperately for air. When she reaches in his shorts and pulls out his cock and balls he seems to relax and maybe thinks he’ll get a hand job… but no… another slap in the balls and he kicks like he’s reaching for the sky. He almost knees Skylar in the face but luckily for him she backs away and saves him the wrath that would surely come from such an occurrence. After more tickling and ball slapping and the odd breath of air she starts to mock him for his little penis saying it’s no bigger than a baybees, or a birds, Eventually Skylar turns around to give you a great view of her backside before again sitting on the slaves head. She almost falls off the facesitting box and says, “We need a bigger seat for this big bum.”, giving it some sexy slaps. Eventually she decides it’s time to sit on the slave until he stops kicking. As he thrashes, she puts her head back and laughs and laughs as the slave goes limp.

Mistress: Princess Skylar
Category: Face Sitting, Ass Smothering, Ball Abuse, Face Sitting, Tickling, Small Penis Humiliation
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Clubstiletto – Princess Skylar – Big Beautiful Babydoll Trampler

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Princess Skylar looks delectable as she walks down the steps in nothing but a babydoll outfit and stiletto’s, after a great nights sleep. On leave from army duties she has had her slave locked up all night, in the cold room, after trampling him the night before. She calls him over and he crawls to her and kisses her shoes as she sticks them through the rails on the stairway. She tells him that she did not like his complaining yesterday and today he has a chance to prove himself… again. Skylar is not a light girl and she shows no mercy walking over his chest and stomach. She asks him if he appreciates her weight and when he says yes she decides to dance on him. Nice camera angles, from the slaves perspective and others looking down from above. If you enjoy seeing a slave suffering under the heels of a heavier domina, you will really want this clip.

Mistress: Princess Skylar
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Clubstiletto – Foot Sucking and Fucking Brother

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Princess Skylar comes into the house to find her brother waiting on his knees for her; blindfolded with hands cuffed behind his back. She has left him there and told him not to move until she returns. She takes hold of his leash, and as she sits down, she tells him how the heat outside has made her all hot and sweaty, especially her feet. She looks at the bottoms of her shoes and says “Oh , they’re filthy…and that’s why we have you, isn’t it?”. He obediently responds “Yes, Mistress”, and as she seductively raises one shoe towards his face, he starts to lick the sole. She shoves a stiletto into his mouth and tells him how disgusting he is. She asks if he recalls their younger days when he treated her so badly. “Well guess what? It’s my turn now.” She makes him suck both heels, and when she explains how this will be good practice for sucking her boyfriend’s cock later on, he gets instant wood. Throughout the scene she makes the slave lick her feet and suck her toes; she spits on him, kicks him right in his hard little cock, and torments him further by allowing him to fuck her feet. The only lube is his own spit between her feet. You can see Skylar really loves being in control as she’s very demanding and demeaning towards her big brother. As he fucks her feet she tells him that this is as close to fucking her as he’ll ever get. She then demeans him further by telling him how small his cock is compared to her boyfriend’s. Then just as he’s about to cum, she pulls her feet away and tells him he will cum only when she decides to allow it. Totally bl@ckmailed, he can only accept that this is just the way things will be from now on.

Mistress: Princess Skylar
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Clubstiletto – Breast Worship Cum Shot

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Skylar tells her brother that although he is older she feels, now that she has turned him into her slave, that the roles have changed and she is more like a mommy to him. As he has pleased her lately she decides to reward him by letting him suck on her full breasts and drain the sweet milk from them. She tells him her good boy even gets to touch his cock. “Nice and slow.”, she tells him, “Enjoy your reward because it will not happen often.” She asks him if he enjoys sucking the sweet milk and when he replies, “Yes Mistress.”, she tells him that does not sound right and asks him again if he enjoys sucking her breasts. This time he correctly replies, “Yes Mommy.”, which makes Skylar smile as she sees how deeply devoted Her brother is becoming to her. She is so pleased she feels he has earned a release but tells him he has to come in the count of 10… and like a good boy he comes right on command. “Now go lick it up.”, she tells him. “Yes Mommy.”, he replies!

Mistress: Princess Skylar
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Clubstiletto – Worship My Sweaty Feet and Creamy Thighs

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Princess Skylar looks so sexy in her cute baby doll and stiletto’s which are resting on her slaves back who is acting as her stool. She’s been in training and her legs are sooo sore. “They just need a massage and some kisses to make them feel better.”, she tells the slave, asking him if he is capable. The dumb naturally says yes. As there is no one else around she decides to promote him from stool to service slave. She laughs at his mask which has no eye holes then criticizes him for just kissing her legs rather than massaging them. Skylar wants to finger fuck herself and tells the slave that is why he is blindfolded, he’s not good enough to see her divine Pussy. The slave presses her fleshy thighs and kisses and while he does Skylar works her pussy vigorously, the pleasure evident on her face. She has the slave remove her stiletto’s and makes him worship her feet while she continues to pleasure herself. She dangles her panties in front of the slave and then puts them on his head so the fabric that was over her pussy is now over his nose. Lucky dawg, sniffing her smelly panties while sucking, licking and rubbing her feet. Skylar is a bit ticklish and giggles while the slave sucks her toes, but soon gets lost in her sexual pleasure. Soon she starts to orgasm, the pleasure all over her face, but then graciously takes her fingers and places them in the slaves mouth. She laughs and says that’s as close as he’s ever going to get to her pussy.

Mistress: Princess Skylar
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Clubstiletto – Princess Skylar – Big Nasty Surprise

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Princess Skylar has recently blackmailed her older brother into being her full-time slave and taken some incriminating photos that she threatens to show his football buddies, if he doesn’t do exactly as told. The scene opens with Skyler on the couch a coy smile on her face, as she spreads her legs you can see cum has dripped out of her pussy all the way down her legs right down to her ankles. She comments what an amazing fuck she just had and then calls her brother from the next room. She tells him that she has a task for him and she makes him get naked. He resists at first but she reminds him that he has no choice. He reluctantly gets undressed and crawls over where she shows him all the cum on her legs. She tells him how awesome her Stud was and mocks him about how little his cock is compared to her lovers. He seems to be rushed licking up the cum, probably just wanting to get it done, but she tells him it’s a privilege and she wants him to slow down and see that he’s enjoying it. She describes her sex in detail, how her boyfriend made her get on all fours, how she loves it when he takes her from behind and fuck her hard. She points to spots he’s missed on her legs and it’s clear that he is going to have to lick up every single drop of the massive load of cum that has leaked from her.

The dynamics of her relationship with her brother get Skylar so aroused that she slides her panties to the side exposing her pussy which she starts to play with. She scolds her brother for wanting to look and tells him that is not appropriate. Again she talks about her lovers big fat cock and how maybe next time she’ll make her brother watch. “Watching your sister get railed by a big black cock, imagine that.”, she laughs. “Maybe you can clean his cock with your mouth after he fucks me.”, she tells him, adding that he’s a “gross dirty little man. “Maybe I’ll have him fuck me in the ass and when he pulled his cock out you’ll have to lick that clean also.”, she giggles. As her brother diligently licks she laughs and says “The funny thing is you have no choice you have to do everything I say, from now on, and for the rest of your life.

Mistress: Princess Skylar
Category: Male Cum Swallowers, Cum In Mouth, Cum Play, Humiliation, Brother Sister, Family Fantasy, Forced Cum Eating
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Clubstiletto – Princess Skylar – Just a Foot Boy

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Princess Skylar is very horny and is about to indulge herself while making the slave suffer. She has him handcuffed to a reclining chair, his head positioned at her feet. She orders the slave to worship her feet while she satisfies herself with a vibrator. As she gets increasingly aroused, the slave is having a hard time concentrating on his task, and she taunts him with the fact that the only vantage point he will ever see her pussy from is from behind her feet. Skylar further teases the slave by playing with her huge tits, asking him if he’d like to suck on them, and then denying him the privilege. The only thing he gets to do is watch, as she she works her way up to a very satisfying orgasm!

Mistress: Princess Skylar
Category: Tease & Denial, Femdom Sex, Vibrator, Foot Worship, Orgasms, Bondage Device
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Clubstiletto – Earn Your Way Up to My Feet

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Princess Skylar is all decked out in her sexy, strappy sandals, but the weather has turned and she has to abandon her walk. Instead, she uses the time to train a slave. He has a foot fetish, but must earn his way up to her feet by worshiping her shoes first. He is made to lick the heel, the dirty soles, and then is permitted to lick the tops of her feet through the lacing of her sandals. Of course, he must take care not to get the leather of her expensive shoes wet! Then Skylar orders her slave to thoroughly lick her toes and consider any toe jam he may encounter between them, his lunch. Next, she makes him remove her shoes with his teeth- and he struggles with both the zipper and the laces. Skylar is left to finish the job, but informs him he will be punished. First he must lick her bare feet clean, then as punishment, he must lick an even dirtier part: her ass.

Mistress: Princess Skylar
Category: Foot Domination, Shoe & Boot Worship, Sandals, Foot Worship, High Heels, Foot Slave Training
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Clubstiletto – Princess Skylar – Learn How to Get Me Off

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Princess Skylar is horny, and she wants her slave to get her off. Since he hasn’t yet earned the right to lick her pussy, he’s got to do it in a more labor-intensive fashion: He’s got to lick ass and use a vibrator on his Mistress. Skylar has him start with ass licking, reminding him that slaves don’t get to lick pussy, but they sure are handy to prep a girl for the arrival of her lover! Next, the slave is made to use the vibrator on her pussy, while continuing to service her ass. The slave fumbles with this multi-tasking challenge, but eventually gets it right. Skylar then tells him to jerk off while continuing to use the vibrator on her clit. Perhaps they can cum at the same time!……Well, fat chance of that. Our princess has a very satisfying orgasm seconds later; the poor slave never had a hope in hell of catching up!

Mistress: Princess Skylar
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Clubstiletto – A Slave for your Sis and Me

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Princess Skylar hasn’t kept her promise of keeping your newly-wed sex life secret. She told your baby sis every nasty, kinky detail. How you’re lucky to even be allowed to lick her feet. How you never see her pussy and tits, but merely serve as a fluffer to her many boyfriends. You’re not a husband; you’re a cuck! The only penetration that occurs in your bedroom is your wife plunging her dildo inside your ass! Upon hearing just what a loser you are, your sis was initially disgusted, but then she became increasingly amused… especially when Skylar suggested they both use you as their slave. Imagine! Your baby sis joining your wife in dominating you 24/7. By the way, wifey even revealed the nastiest detail of all… that you serve as her full toilet. Guess you’ll be doing the same for your sister as well!

Mistress: Princess Skylar
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Clubstiletto – Princess Skylar – Cuckie’s Nasty Duties

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Princess Skylar is a young lifestyle cuckoldress who is new to Club Stiletto. She loves hung studs, especially black men but dont worry; she married you for a reason! She needs a cuckold… and thats you. In this scene, she fleshes out what it means to be a cuck. She exposes her big breasts to you, but informs you they’re not for you to lick. She teases you with the sight of her pussy, but again, your cock is not penetrating that! What is left for you to do then? The dirty work! If you’re not bankrolling her lifestyle, you’re cleaning the grit off her sweaty feet, cleaning her dirty asshole, or licking the stench off her pits before one of her boyfriends arrives to fuck her. Yes, other men will be fucking her; guys with big dicks who actually turn her on. Your job is to prepare her body for these sexy encounters, and fluff those big dicks so they (and she) can cum! You are a cuckold!

Mistress: Princess Skylar
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