Free Spanking and BDSM Videos and Galleries with Rosie Ann, also known as Rosie and Rosy Ann. We have previews with Rosie Ann from 11 Premium Sites.
Rosie Ann Is Ready To PartyRosie Ann has been into the spanking scene for many years but hasn't made a film in almost 10 years. Imagine my excitement when she contacted me to ask if she could come and make some films with us. This is a lovely custom film where Rosie has been asked to go to a spanking party and wants to see if she will enjoy it.. She knows I have a very hard hand so asks me to give her a good spanking on her delightful bare bottom. I do not hold back and give her a blistering smacking but guess what? She loved it! So much so that she asked for ma to use a paddle as well. The hard Janus paddle is applied rather firmly to her bottom.Spanking Session ModelsThese are 2 hard working girls who live together and they return home and get ready for bed. They discuss their different spanking modeling assignments that day. They compare their work and each others bottoms before getting a little turned on... They both decided to warm each others bottoms up again so they can see their marks from earlier in the day!Upping Her Game - Part 2Rosie Ann is lucky enough to have a sponsor for promising future in ladies tennis. He spends an awful lot of money on his protege and Rosie is of course grateful. She doesn't even really mind the punishments that live alongside the rewards. As for him, the rewards are immense!Upping Her Game - Part 1Its Wimbledon fortnight again and we know what that means, don't we?! Rosie Ann is lucky enough to have a sponsor for promising future in ladies tennis. He spends an awful lot of money on his protege and Rosie is of course grateful. She doesn't even really mind the punishments that live alongside the rewards. As for him, the rewards are immense! He gets to mentor an affectionate and bright young lady who rather likes the little skirts and white panties... and the spankings!Spanking Interview With Chessie Rosie & MichaelMeet the girls and hear what Michael had to say about them in this long day's film shoot! They answer some questions and the girls can't wait to show off their red bottoms once more teasing Michael into spanking them again!A Series Of Unfortunate DisciplineWhere do we begin with this film? In this heavily redacted final edit (mainly to protect other guilty parties), we have some semblance of near normality as a seemingly innocuous tale of Rosie Ann being punished (for various cheering infractions) soon goes off the rails with some behind the scenes shenanigans that brings in another perpetrator to receive an impromptu spanking too! Rosie is spanked, strapped, and caned for foolishly doodling on the blackboard and her general sassy attitude. In an unseen break, a message that John had written on the blackboard is changed without his knowledge. He eventually discovers that the message he wrote on the board about her receiving punishment was changed to 'chocolate'. Everyone off-camera was in on the joke apart from him, who upon discovering the edit, the course of the narrative turns on its head as pandemonium ensues. Jadie Reece was the perpetrator and she is told to get on set and face a similar spanking, strapping and caning as Rosie. Despite her giggling protestations, John ensures she gets it hard, alongside Rosie who receives more punishments too. This is a good hard discipline film with a lot of laughs in between. Despite the mirth and mayhem, it's a great film with good hard scenes of hand spankings, leather reformatory straps, and of course, the cane! All used to great effect across naughty miscreants backsides!1970s Spanking DisciplineThis is a tale from the miracle modern age of the 1970s... Man has landed on the Moon, C90 cassette tapes make portable audio recording for the masses possible, Women's Lib and Flares are in fashion! What hasn't changed in this new decade though is the use of good old fashioned discipline! Spankings of miscreant young ladies are still carried out just as they were decades before! Stephen Lewis is the medical director of a care home facility and one of his student interns, learning how to care and nurse for the elderly, has been causing a stir with the frail folk. They might just suffer a seizure or cardiac arrest from the skimpy, short lewd skirt, revealing her pantyhose and panties that she is wearing as she bends over attending to patients! Her behavior is reprimanded and Doctor Lewis sees no alternative but to teach Nurse Rosie Ann the trusted lesson of an old fashioned, over the knee hand spanking. First, he spanks her over her slutty pantyhose and knickers but soon turns his attention to her bare reddening bottom. Rosie doesn't seem to be learning her lesson at all, despite her sore bottom... and forgets that there are several leather implements of correction on the table. He chooses a nasty double-tailed leather strap, placing her (bottom stuck out) over the table. Rosie cries out in pain and winces as the leather strapping she receives finally gets through to her. She will not be teasing or causing unnecessary medical issues with the obscene view of her very short, provocative, and highly inappropriate uniform in the future. This may be the exciting new decade of the 1970s, but professional standards must be maintained!Rosie's Punishment LinesInmate Rosie Ann Was called in by the Governor to write a report but instead of writing, she doodled. The Governor soon noticed and told her to write 50 punishment lines while he strapped her insolent 18 year old bottom.Uniform InfringementRosie Ann is back and it seems she never learns her lesson and only remains in the squad after receiving various punishments as she is by far the best cheerleader in the squad. However, when she turns up for competition in a spare uniform without the team logo, this really is the last straw. Her excuses are predictable and poor and Coach is having none of it. He spanks her as he has done previously, even spanking her hard on her bare, jiggling bottom. That certainly grabs her attention as his hand is mean and unpleasant, smacking her hard. As we said earlier, she never learns... and her attitude gets her into further trouble as this time Coach decides to use a wooden paddle and cane with her bent over a chair, her bottom and private parts on full, humiliating display. She isn't so cocky now and takes several swats and strokes of these implements which finally teach her a humbling lesson that being a team player is more important and she promises to do better in future.Rosie's Bedtime PunishmentRosie is having a bath and mommy has asked her repeatedly to get out as it is time for bed. Finally mommy has had it with her disobedient daughter and grabs her, pulls her out of the tub, drags her to the bedroom, and throws her over here lap for a spanking. Rosie cries in pain as mommy spanks her wet bare bottom with hand and hairbrush.Rosie's Humiliating PunishmentRosie's grades have slipped and this is unacceptable! She is sent to head sister, Sarah, to be dealt with. Punishment is in order for this naughty sorority sister. First it is over Sarah's knee for a hard hand spanking over her jeans, panties, and then bare bottom. Then, she is made to strip for the more humiliating part of the punishment. This includes having her hands tied over her head, being completely naked and fully exposed for her spanking and paddling.Learn To Say SorryHead cheergirl Chessie & bookworm Rosie Ann were caught fighting outside the school gates. This sort of behavior was most unbecoming such a school so both girls were told to wait in the cellar on the punishment bench. They knew that they were going to get a punishment, all the girls would talk about this room with dread. Looking into each others eyes as part of the rehabilitation that both girls hated - they were spanked again and again until the pain and embarrassment of being stuck together like this earned them a reprieve when they genuinely said sorry to each other.Inappropriate UniformsChessie and Rosie were in detention for wearing the sluttiest of uniform modifications. Their skirts were way too small and their shirts unbuttoned with their breats poking out and Chessie's make up was trashy at best! One by one the girls were given their punishment like the sluts they apparently seemed to like being until they learned that this had painful consequences. Look out for a good hard wooden paddling of Rosie's firm cheeks!The Snitch And The TrespasserChessie brought an outsider to her Head teacher, Mr Stamp. the girl was Rosie Ann, from the all girls school nearby. he wasn't impressed with how Chessie had so gleefully presented Rosie to him so he decided to punish them both as an example. First he caned Chessie in front of Rosie... then told Rosie she'd get the same but far more severely for daring to trespass on his school grounds!Caught StealingChessie and Rosie were caught stealing from the lockers red handed by Form Teacher, Michael Stamp. He marched them to the Detention Room for a short sharp shock punishment on the 'Spanking Horse'. The girls had a bare bottom spanking and strapping facing each other in shame after a hand tawsing for stealing from their classmates.SleepoverRosie is staying over at Chessie's only the girls disturb Michael downstairs who has already warned them to keep the noise down. A moist pillow fight is the last straw for Michael and he teaches the girls that they should have listened to him earlier rather than get the painful bare bottom spanking in front of each other!Chaise Long SpankingThis is Rosie Ann's induction in the Punishment Room. She reports to see Michael for her 5pm punishment. She is given a bare bottom OTK spanking and the chaise long is used to place her in various embarrassing positions as her bottom is given a good work out!Spanked in her JodhpursRosie helps out at the horse stables of her mother's best friend, Jadie Reece. She has a reputation for being a strict disciplinarian. Rosie secretly fantasizes that she would get punished by her and decides to see if Jadie's reputation is real or not! Instead of preparing Jadie's favorite pony she still has the saddle indoors and pretends that she is riding a pony! It's not long before an irritated Jadie catches Rosie in the act. Not only is the saddle not ready but she took her favorite riding crop and hat that she had been looking for. Jadie's tone changes, 'this is it!' Rosie thinks... she can barely speak, her throat is dry and her heart racing as Jadie scolds her, promising discipline there and then. Rosie is spanked still 'riding' the saddle, her tight jodhpurs stretched allowing Jadie's hard hand to smack her throbbing bottom! Rosie's head races with mixed emotions; fear, excitement, trepidation... her head is buzzing and barely hears the order to pull down her jodhpurs for a bare bottom spanking. She fumbles with the buttons... and trembling, does as she is told! With her bottom in the air, Rosie complies silently offering up her bared cheeks to the riding crop and a stinging leather paddle that Jadie kept for the stable boys! Now this paddle has a new victim. Rosie's bottom is red and visibly swollen at the end of this punishment. Jadie leaves her to compose herself and reflect on what had just happened, reminding the young girl that she still had a job to do. Get the pony ready for the morning ride!Exercise SpankingsRosie's personal trainer had only left the room for a few minutes and on his return he caught her performing some unorthodox balancing moves which could have injured her back. She was supposed to be doing more core exercises to strengthen her back, not ruin it! She knew the score when he was displeased and knew that various humiliating punishment moves would follow! Perhaps Rosie wanted to be caught? Who knows? She is a very naughty young lady! Rosie gets spanked in differing positions without too much complaint over her tight exercise shorts before these were pulled down and the harder spankings continued. Next followed more embarrassing positions, exposing the poor girl as her bottom was strapped and paddled. At the end you'll see her doing the exercises she was supposed to be doing with a sore red bottom on full display. Fans of Rosie Ann will love this video as she demonstrates how versatile and athletic she is whilst taking an unusual spanking punishment!Punished by the park keeperRosie takes a short cut home through the park after a Girl Guide church practice on a glorious Saturday afternoon. It is so warm and sunny that she finds a secluded area of the park where she dares herself to be very, very naughty! She starts to touch herself through her crisp, white cotton panties. Her legs spread wide as she continues to delicately finger her wet pussy. She thought it was a secret spot but the Park Keeper recognizes her when he is in the area and tells her off, scolding Rosie about her rude behavior! He knows her parents and decides that a spanking might make her realize this sort of lewd behavior deserves at least a bare bottom spanking. She feels embarrassed and knows that if he tells her parents she would surely get another spanking at home! The Park Keeper was going to let her go but her sassy mouth gets her into trouble! He pulls off his belt and bends her over the bench where she had been masturbating just 10 minutes earlier. Now he is really going to teach her a lesson in manners! Rosie yelps and takes stroke after stroke of his leather belt until only he was satisfied that she has properly shown remorse for what she has done! See cute Rosie Ann make her return to Triple A... One of our most popular girls at her very naughtiest best!The Ballgagged SchoolgirlRosie Ann faced her most humiliating detention punishment to date when her potty mouth got her into trouble. Mr Osborne wasn't going to listen to anymore of her 'F Bombs' and shut her up immediately by ballgagging her. This shocked schoolgirl then went through the rest of her punishment muted except for the muffled sounds of her cries of pain. He punished her for the other misdemeanors such as smoking, for which she received a hard and painful wooden ruler first on on her hands then later on her bare bottom! A hard OTK bare bottom spanking and a double thick heavy leather strap ensured this foul mouthed young lady learnt her lesson thoroughly in her after school detention. This was by far Rosie Ann's most humiliating spanking punishment to date!Rosie's RoutineYoung Rosie was in training and asked her coach to give her some unique reminders in strength building and holding poses while on the gym horse. She wanted to see if she could endure pain and embarrassment in various positions whilst carrying out her routine. If she could overcome this each time then performing without the distraction would make her a winner. We think Rosie is an absolute star, watch her get spanked and paddled in a variety of different, awkward and very revealing positions - another film taken from our 'Exercise Discipline' series.Fantasy or RealityThis is a schoolgirl discipline film with a difference. Rosie is waiting for her detention punishment & Has no idea what it will be...so she imagines two scenarios: The first is erotic & About as far from reality as possible when she gets turned on imagining that she gets a 'good girl' hand spanking & A riding crop used on her intimate parts (well, it was Rosie's weird fantasy punishment!). Then as she snaps out of that daydream, she fears that it is actually something far worse, & Probably closer to what she is about to get... A hard, painful wooden paddling on her bare bottom. This she doesn't like at all & As she comes back to her present predicament of waiting for her punishment... In walks her teacher with a heavy cane who promises Rosie that she will feel 12 hard strokes which you will see is done in an authentic & Traditional no nonsense 'matter of fact' way! You'll see this punishment film develop from Rosie's strange daydreams & Fears to what actually happens over the space of the 17 varied minutes!Rosie's Spanking ChairThis unique short sharp shock film stars stunning Rosie Ann, dressed in a cute, very sexy school uniform. It was her turn to be spanked over the chair but Mr Stamp had a special implement that he had decided to use this time... A hand paddle that hurt far more than a simple hand spanking! Rosie's bottom quickly turned red under her white panties and when they were removed the painful OTK spanking continued. This punishment was far from over, as he had decided she should receive a particularly humiliating end to this discipline session. He positioned her so that Rosie sat over the chair in reverse, with her bottom cheeks hanging out over the edge of the seat making her feel very vulnerable to yet more strokes of that nasty wooden hand spanking paddle! This film contains 3 different camera angles so that you won't miss a single part of this revealing and embarrassing session that poor Rosie endured!What Rosie WantsRosie wanted to be spanked and punished in a variety of positions of her choosing. Knowing Rosie, we knew that this would be interesting and you will not be disappointed. She started off getting spanked upside down in a cute pair of white open crotch bloomers... She suspended herself from a high bar using her arms and legs wrapped around it for support. This was a precarious position but her core strength and agility won out against John's hand as he reddened her bottom up nicely. This was only the warm up as Rosie next asked to be spread on a spanking bench and caned hard with fast and furious strokes mixed with some very thuddy ones which really got the endorphins flowing. Her third installment was on a St Andrews Cross that she had seen. She was tied to it and given two of the meanest heaviest straps in our arsenal. One was a rarely used double thick, double stitched leather strap with a lot of impact and the other was a never before used large rubber strap from Caniac that no girl had dared take on... Until now! Anyone who knows how horrible heavy rubber is will understand that you do not need much of a swing for this to hurt. John took large swings of it anyway and Rosie was just up to the task! Finally she was impressed by our addition of a brand new dense oak wooden spoon (very ouchy!). This final request was for a kitchen scene and where this awesome video ended with her getting countless swats and whacks with this implement. In all, there are 24 minutes of non stop hard hitting punishment action for you to view and this video features special 'slo-mo' scenes as well as bonus footage at the end!The Caught Short VideoRosie Ann was the last girl in her detention session on the school trip before they all had to catch the bus home and she begged to go to the bathroom early as she was aching to go. She is just 18 years old and should know better but she was caught short and made a bit of a mess in the bathroom, wetting her panties and the floor. Her teacher caught her trying to clear up the mess and punished her further with a humiliating bare bottom spanking followed by forced pantie washing and wearing of the wet cotton undergarments underneath her short skirt as a shameful reminder before she was sent on her way to the waiting school bus to take her and the rest of her classmates home from the weekend retreat!A Bad Place For Good GirlsA bus station is a bad place for good girls to hang out! When eighteen year old Rosie Anns parents got a call from her best friends family, letting them know that the girls were caught hanging out among the crowd of delinquents there, Rosy was definitely in trouble. Like most girls her age in the nineteen eighties, she was no stranger to getting her bottom smacked but, this time, she was in bigger trouble than that. This time, she was going to get the cane.Having mostly been a good girl, Rosie had never been punished this way before, and she was scared and nervous from the moment she saw the thick, rattan implement. Being mostly good, she did not protest against the punishment she knew she deserved. Her round little bottom was soundly spanked until it glowed red through her white school knickers while she grimaced and whimpered. Then she was ordered to kneel up on the bed, presenting herself for the harsher discipline she required for being such a wayward, naughty girl.What followed was a hard caning, with each stroke biting into her tender cheeks and making her lunge forward, trying to escape the pain that never seemed to stop growing. The strokes were hard, and they did not get any softer when she whimpered and cried out: she needed to learn a lesson.Once Rosie had been properly beaten, she collapsed on the bed, her red and swollen bottom sticking up.Detention Number ThreeRosy Ann finds herself in detention for the third time in a term. As Jenna, with whom Rosy was caught fighting, has just found out, in the third detention, your knickers are taken down and your bottom is introduced to the tawse. Rosy is not looking forward to her fourth detention.Monty's Missing DinnerRosy Ann has the mother from hell. More concerned with the impact on her social diary than Rosy or her little brother (Monty)'s welfare, Jessica shows her frustration by smacking Rosy's bottom, followed by an application of the hairbrush in an embarassing legs-up position. Rosy wishes she were an orphan. 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