Free Videos and Galleries with Case Cherry. Her videos presented on this page feature scenes in categories Spanking, BDSM and Lesbian. Case Cherry is also known as Cherry Winters. We have previews with Case Cherry from 6 Premium Sites.
Deception And DisciplineCherry, a defiant young lady, thought she could outsmart her mom with a web of lies. But after a night of sneaking out, her mom has caught her. Confronted, Cherry tries to downplay the situation, claiming it's 'no big deal.' However, this isn't the first time she's pushed the limits, and her mom has had enough. The punishment begins with a stern scolding, followed by a firm hand spanking Cherry's pajamas-clad bottom. But as the lies continue to unravel, Cherry's mom demands the truth - and a more severe punishment. Cherry is made to surrender her dignity, asking for the hairbrush and acknowledging she deserves it. The hairbrush spanking that follows is merciless, leaving Cherry's bottom a deep shade of red. But even that's not enough to satisfy her mom's anger. A hard strapping is the final act of discipline, a painful reminder that deception will not be tolerated.Cherry Winters Dishes It Out As Well As She Takes It - Making The Squad 2Earning her place on the Squad, Cherry must prove that she can dish it out as well as she takes it. Kiki switches places to test her new recruit , offering her bottom and pussy for testing. Skirt flipped up, sharp spanks give way to the stiff leather strap on her succulent bottom. Cherry spreads her legs and spanks Kiki's horny little pussy, punctuated by the crack of the leather paddle. Her juicy bottom jiggles as she takes her swats like a champ, the caption of the squad must always be impressive and able to take what she dishes out. Panties pulled to the side, her pussy is spread and spanked, Cherry enjoying her reactions. Flipping her over on her back with her legs spread, Cherry puts Kiki in the perfect position to torment her pussy she continues to spank. Expertly applying the vibrator directly to Kiki's clit, the leather paddle torments her flushed cheeks with her legs spread. Cherry is going to be the perfect addition to Kiki's Squad of slutty cheerleaders.Spanked For Owing MoneyCherry Winters has borrowed money from Claire Cummings and still cannot pay it back. Claire believes that Cherry needs some motivation and that comes in the form of a spanking and paddling over her knee. Cherry will find a way to pay it back.Making The Slut Squad - Kiki And Cherry Winters - FacecamKiki auditions Cherry for a spot on the Cheer Squad. Cherry is determined to pass the initiation, no matter how painful and humiliating. Kiki pulls up her top to inspect and grope her tits, before laying her on the bed to flip up her skirt. All the other girls have gone through a similar hazing, and are not strangers to a good spanking. Cherry's bottom is tight and tiny, her alabaster skin stinging under Kiki's sharp slaps. Pulling her white thong up into a tight wedgie, her hands slide to pet her pussy as the spanks continue. Kikis continues to put her through her paces, spreading her legs and sliding her panties down. She yelps as her pussy betrays her excitement, Kiki's fingers doing a full inspection. Girls on are squad need to cum and fuck and moan like a hot girl. Kiki spanks her throbbing pussy until Cherries excitement is all over her fingers, pausing to make her lick it off. Picking up a stiff leather paddle, Kiki spanks her bare bottom hot and pink as Cherry continues to moan and drip with arousal. Putting her on all fours with her ass in the air, the strapping and fondling continues. Positioning a small pink vibe, Kiki continues the humiliating spanking as Cherry begs for relief. Finally allowed to cum, Cherry is one step closer to earning her spot on the sluttiest squad on the west coast.Making The Slut Squad - Kiki And Cherry Winters - ButtcamKiki auditions Cherry for a spot on the Cheer Squad. Cherry is determined to pass the initiation, no matter how painful and humiliating. Kiki pulls up her top to inspect and grope her tits, before laying her on the bed to flip up her skirt. All the other girls have gone through a similar hazing, and are not strangers to a good spanking. Cherry's bottom is tight and tiny, her alabaster skin stinging under Kiki's sharp slaps. Pulling her white thong up into a tight wedgie, her hands slide to pet her pussy as the spanks continue. Kikis continues to put her through her paces, spreading her legs and sliding her panties down. She yelps as her pussy betrays her excitement, Kiki's fingers doing a full inspection. Girls on are squad need to cum and fuck and moan like a hot girl. Kiki spanks her throbbing pussy until Cherries excitement is all over her fingers, pausing to make her lick it off. Picking up a stiff leather paddle, Kiki spanks her bare bottom hot and pink as Cherry continues to moan and drip with arousal. Putting her on all fours with her ass in the air, the strapping and fondling continues. Positioning a small pink vibe, Kiki continues the humiliating spanking as Cherry begs for relief. Finally allowed to cum, Cherry is one step closer to earning her spot on the sluttiest squad on the west coast.Punished On Prom NightCherry thought she had the perfect post-Prom night planned: A hotel room paid for with her mom's credit card and a romantic long night with her boyfriend. However, Cherry's mom finds out, and her evening takes an unexpected dramatic twist. Mom shows up, upset, and confronts her sneaky daughter. Cherry tries to talk her way out of trouble, but that just upsets Mom more. She is taken over the knee for a proper punishment with a much-deserved spanking. Mom pulls down Cherry's skimpy panties, removing them completely and spreading her daughter's legs to humiliate the slut. Cherry was planning to open her legs for her boyfriend, but the only opening tonight will be for Mommy during her punishment. To complete her humiliating discipline, Cherry is bent over the couch and given a leather strapping for the deceit and upset that she has caused with her lewd behavior.Lexi Spanks Cheating CherryLexi has recently discovered that her boyfriend has been cheating with her supposedly trustworthy roommate, Cherry. What follows is awkward for Cherry as she tries to deny, deflect, and lie her way out of trouble but this only infuriates Lexi further since she has all the evidence to prove otherwise. The only thing Cherry can do is take the proposed punishment for her cheating, slutty behavior, or else be kicked out immediately! She chooses the spanking option and knows that Lexi has also been brandishing a hairbrush that she is aching to use on her behind later... this is going to be embarrassing but it will help set things right between the pair. Cherry's sexy bottom is spanked with stunning Lexi's hand over her lap and the sight of these beautiful leggy ladies is enough to raise the temperature to beyond 'hot' as the cheater's panties are peeled down revealing a reddening bottom. The red-haired temptress dangles her legs over her pretty roomie's lap for the hairbrush spanking which is mean and grabs the attention of the slutty roommate! Enjoy this incredible, hot, all-girl spanking punishment film - another to view and add to your increasing library of fine spanking erotica.Slutty Submissive Punished AgainCherry Winters has once more disobeyed Mistress by being a little slut and having fun with men! Mistress owns Cherry, especially her pussy, and she is the only one who should be sticking things inside that sweet honeypot. Cherry is also not wearing her collar which infuriates Mistress further. She has had enough of this behavior so it is time to teach her naughty submissive a lesson again! She begins by strapping Cherry's nipples and milky white breasts until they are glowing pink. Of course, other parts of this beautiful submissive's body are also dealt with including her slutty pussy. Mistress strips her girl and then straps her tight, pert bottom until it becomes pink and sore. Cherry is then placed on the couch sitting with her legs spread wide as a leather crop swats her pussy and the strap is used over her inner thighs making Cherry wince in pain. Her punishment ends with a caning on the bare bottom as well as the front of her delicate thighs. Cherry has learned a valuable lesson in respect and being a proper submissive.Order Through DisciplineCherry is at home lazing around, dressed inappropriately and with her boots on the couch. She is about to be rudely interrupted by her long-lost Aunt who makes a most unexpected appearance. After realizing it is her strict Aunt Clara from overseas, Cherry knows she is in trouble being sternly lectured and scolded about her demeanor and appearance. That is not all... the fact that she has been vexing her poor mother with her rude, selfish, and arrogant behavior at home is why Clara is there. This all stops today as Aunty has been asked to instill that much-needed order and discipline that Cherry so lacks. Spanking is a way of life for Clara and she introduces this to hapless Cherry, who ends up over the lap of this stern matriarchal figure and it isn't long before the rude girl's shorts and skimpy panties are pulled down for a richly deserved hand spanking that soon reddens her tight bare buttocks. Then the hairbrush is produced, which has Cherry gasping out in pain and shock as the Mason & Pearson implement strikes her soft tender nether regions with precision and pain. Order and discipline are about to be restored in this house as Cherry is left to soothe, caress, and rub her reddened bottom better.Cheating Has ConsequencesCase is waiting for her cheer coach to turn up and take her to practice but when she hears the doorbell and answers... it is her Headmistress, Miss Matthews. She invites herself in and approaches Mom (Miss Bernadette) informing the good lady that her girl has been caught cheating at a recent important exam and that this disciplinary matter needs immediate attention. There is no cheer practice today for this young lady, just discipline... which she is about to discover is painful and embarrassing! Headmistress learns that Case never receives spankings or punishments at home, just a stern chat from Mom (at best). This will not do and Case is taken over the educator's lap for a lesson she will learn and which her Mom will understand and follow through on afterward. Case is spanked in her cute cheerleader uniform and the spanking continues over Miss Matthews' lap with the girl's panties pulled down for added humiliation. This punishment deserves more than just a hand and a typical implement found at home such as the wooden hairbrush is used across the embarrassed cheater's reddening backside. This new lesson is learned twice as Case has the same treatment repeated over her mother's lap as the Headmistress encourages from the sidelines. From now on, this is the type of correction she will experience if her poor behavior warrants such actions at home as well as at school. Today, the lesson learned is that cheating has consequences!Case Cherry Spanks Stevie Rose Over RentStevie Rose and Case Cherry are roommates. When Stevie cannot pay her portion of the rent this month, Case has no choice but to spank Stevie over her knee as part of their agreement. Case uses her stingy hand plus a wooden paddle to drive the lesson home, turning that curvy bottom bright red.Stevie Spanked Over Room ChoiceStevie Rose tells new sorority girl Case Cherry that she will do anything to switch bedrooms with Case. It seems like Case has been dreaming about spanking Stevie ever since she joined the sorority and this is her big opportunity. She puts Stevie over her knee for a sound spanking, including the wooden paddle.Slutty Submissive's PunishmentCase Cherry and her Mistress, Miss Bernadette, are at a spanking party. Case is supposed to be on her Mistress's arm and only playing with her. Instead she has disappeared and decided to play with a cute guy. Mistress is less than pleased and plans to mark up her little submissive to show her who she belongs to. Case knows that the punishment won't be the fun and sexy play she enjoys. First, Case's legs are spread and her pussy is cropped. After-all it won't be anymore pleasure for her little cute pussy, just pain. Then she is stood up and given a hard strapping. legs spread and stripped. She knows that her punishment always ends in a caning. Mistress gives an already very sorry submissive 6 strokes of the cane on her bottom and then 6 more strokes on the fronts of her thighs. Case is forgiven for her naughty behavior and held.New Girl Case Cherry Spanked By Stevie RoseNew girl Case Cherry, in her first spanking shoot, gets spanked by Stevie Rose for stealing her favorite client. Stevie teaches Case a lesson with this long, painful spanking over her knee, with hand and large leather paddle. The cute perky bottom turns bright red and Case has trouble sitting after.Partygirl PunishedThis is a precautionary tale for those party animal hedonists who are too selfish to care about others when staying at busy hotel chains. Imagine, if you will, one such story of Case Cherry... who entertained far too many people by hosting a noisy, feral party... much to the annoyance of other regular guests at this particular hotel. Then on the morning after the night before... Case is confronted by one such angry guest who just happens to be Miss Bernadette! She barges into Case's room, the girl is unaware of just who she has royally upset but she is about to discover the hard way, just who! Bernadette chastises her how girls who selfishly party the night away will be punished for their sins! Bernadette then drags Case over her lap, the young girl is still in shock that she is getting spanked but the humiliation goes up a notch as her tight panties are quickly removed too. Her pert, tight bottom bounces and jiggles as she is given a thorough hard hand spanking by Miss Bernadette. The punishment is far from over, she is treated like a slut, and her legs are splayed as Bernadette admonishes Case, continuing with the bottom smackings. The leather strap that Bernadette brought with her into the room is used next across Case's reddening, sore behind... the hapless girl is placed over the couch and given a proper leathering that has her gasping out loudly in disbelief. Now she knows the hurt of payback for her party antics from the night before. She is left to contemplate more of the same, clutching and rubbing her sore, aching bottom... that there will be more of the same if she dares ruin any hotel guests' stay in the future!Exercise Takes DisciplineIn the latest of our popular 'Exercise & Discipline' series, Case Cherry and Alice Payne (aka Alice in Dallas) are sexy roommates who motivate each other to work out and get to the Gym as often as possible. Case has been telling fibs recently, avoiding Alice when it is time to go to their Gym appointments. Alice is the dominant partner in this relationship and reminds Case what happens when she behaves like this. She takes the super sexy long-legged Case over her lap as her firm hand connects to her friend's toned round bare buttocks. Alice is far from finished with her cute friend as she also uses a hairbrush with Case placed in 'The Plank' position, ensuring the sexy roommate's cheeks get properly tanned. Finally, she is placed over the couch, bared and exposed, as Alice inspects her work and continues to spank Case until she promises to go attend the Gym with her as agreed! These two ladies have great chemistry, Alice as an incredibly hot Top, and Case (the cute long-legged submissive) with a beautiful spankable bottom!Rules & ConsequencesPlease welcome Case Cherry, another new girl we discovered recently who we are sure you will adore getting spanked! Case has been called to CEO Johnny Lake's Executive Lounge as he has heard disturbing reports about one of his best new interns behaving inappropriately. he reminds her of the rules regarding professional attire and that there are rules and consequences when these are broken. Everyone knows Mr. Lake has a unique way of carrying out discipline... and he is about to teach her how to be 'professional'. She is scolded and taken over his lap for a hard hand spanking that has her delightful bottom redden quickly. her long legs are draped over his lap and sofa making for an alluring sight as she learns to repeat the mantra of being more professional. Next, she is introduced to his leather strap, and he bends her over the ottoman, with her tight peachy red bottom stuck out and presented as an inviting target. After many swats of leather, she is left to compose herself in the Executive Lounge, rubbing her aching sore red spanked cheeks better.Corrective Measures For CaseCase is lounging around in panties and a crop top when Johnny arrives home. She should know the House Rules by now and she is quickly reminded of them on his return: when she is in the Living Room or anywhere else in the house (besides the dungeon) she must wear appropriate clothing. Anyone could see her; The chef, housekeeper, or even other family members. Johnny is not happy at the state of her slutty attire for which the hired help could stumble across. He makes an example of his naughty girlfriend, taking her over his lap for a much-needed, corrective hand spanking discipline. her slinky legs draped across the couch and her reddening bottom do not distract Johnny from the task 'in hand'. Please welcome Case in her debut spanking performance on our sites... we are sure you will want to see more spankings of her soon! 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