Tag: Miss Anna

Triple A Spanking – AAA Spanking – MP4/Full HD – John Osborne, Miss Anna –

Triple A Spanking – AAA Spanking – MP4/Full HD – John Osborne, Miss Anna – Anna Never Learns

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Triple A Spanking – AAA Spanking – MP4/Full HD – John Osborne, Miss Anna –

Anna has been caught out lying to John over a missed payment to a company that they had agreed terms with for a specialist new vacuum cleaner for their carpets and rugs. They had been impressed by the demonstration which cleaned one particularly dirty rug so they agreed a payment plan. However, Anna pocketed the cash John had provided and spent it on lingerie and personal grooming products instead and kept this a secret for quite some time until they contacted him directly! He presented the evidence of a lack of new vacuum cleaner and irate calls from the company but she continued to deny any wrongdoing! He was angry and tried to give Anna a chance to own up but she had continued to lie and once again was not learning lessons about this sort of behavior. Only a severe punishment would work, he thought, so he presented his thick leather belt and heavy bathbrush he knew Anna hated. he spanked her first, scolding her and reminding her of what was to come across her bare bottom. The leather belt was relentless and stroke after stroke hit the target ready for the final tearful severe bathbrush spanking that you have to see to believe! Anna’s poor bottom took one hell of a lengthy punishment!
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Triple A Spanking – AAA Spanking – MP4/Full HD – John Osborne, Miss Anna – Anna’s Severe Discipline

Triple A Spanking – AAA Spanking – MP4/Full HD – John Osborne, Miss Anna – Anna’s Severe Discipline

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Triple A Spanking – AAA Spanking – MP4/Full HD – John Osborne, Miss Anna – Anna’s Severe Discipline

This is a special long play film that features Anna and John, who had a real-life mentoring relationship at the time of filming. John cares very much for Anna and she needs hard discipline when she doubts herself or puts herself down. They have never filmed anything publicly like this, until now. This is typical of some of the sessions they have worked through in private. Anna is an incredible woman, she often doesn’t know it and although she has a great tolerance for more severe style punishments she feels every slap. swat and stroke. The reasons for her punishments are discussed briefly throughout but the focus is on “how” she is punished. There are a variety of wicked and nasty implements which she dreads and is familiar with. So John starts with a hard hand spanking, he wants her to reach her threshold with each style he uses. The over the knee spanking is more personal before she is placed on the ottoman, bottom-up, for the various leather straps. Some are very stinging, others heavy and thuddy and the tempo is upped until she can take no more of each until he uses the long heavy duty “Hanks gunbelt”. Anna needs to be warmed up thoroughly as the next part involves a large bathbrush and stinging paddle which causes her to yelp out. Check out her facial reactions! This really hurts and the message is getting through about the issues they have discussed. The finale features the anticipated caning. Two different Dragon Canes are used with varying tempo and severity. These strokes are some of the hardest we have filmed and they are applied to an already very sore red bottom! This will appeal to lovers of severe corporal discipline with over 30 minutes of action scenes, it really is one not to miss! This version is in ultra HD1080 at 60 frames per second for greater clarity!
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Triple A Spanking – AAA Spanking – MP4/Full HD – Miss Anna – Secrets Get You Spanked

Triple A Spanking – AAA Spanking – MP4/Full HD – Miss Anna – Secrets Get You Spanked

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Triple A Spanking – AAA Spanking – MP4/Full HD – Miss Anna – Secrets Get You Spanked

It had been some time since Anna and John had spent some quality time together so when it came to their playtime, John was upset to discover that Anna had been keeping a secret from him. "You’ve been seeing him again, haven’t you?" He could see the marks of a recent beating. Anna was so apologetic but John was incensed that she was keeping secrets like this. So he quickly dragged her over his lap and started to give her a hard hand spanking. Anna was already in her sexy lingerie and her long legs kicked as she struggled to take his angry spanking. This was just the start as he loved to use his favorite leather implements, a Reformatory Strap and thick, stiff gunbelt. However, there was to be no sensual spankings, just heavy licks of leather, reddening and marking her full round cheeks. John also knew that a hard discipline session turned them both on so by now he was past caring how he felt about her secrets and he used the heaviest, meanest bath brush at his disposal. This was a mean session with the brush that had her fighting back tears but John saved his best to last! Anna, was ordered to remove her bra, now naked… her full round breasts glistened as the adrenalin coursed through her body as it was time for her caning! Anna positioned herself over the bed for some of the meanest strokes she had ever received. With this over, John wanted to comfort Anna and provide the aftercare she needed. This was such a hot, mean spanking session so he used lots of soothing Arnica lotion, gently rubbing into her sore skin, with equally soothing words in her ear, tender cuddles, hugs and gentle kisses to remind her how much she meant to him. Don’t miss this long play, very grown up domestic spanking video between real life play partners!

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Triple A Spanking – AAA Spanking – MP4/Full HD – Stevie Rose, Miss Anna – Spanking Step-Daddy’s Princess

Triple A Spanking – AAA Spanking – MP4/Full HD – Stevie Rose, Miss Anna – Spanking Step-Daddy’s Princess

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Triple A Spanking – AAA Spanking – MP4/Full HD – Stevie Rose, Miss Anna – Spanking Step-Daddy’s Princess

Stevie Rose had a new stepmom and they didn’t like each other one little bit! Anna made sure that her new bratty step-daughter got no favoritism from her when Stevie’s Step-Daddy (John) was away on business. He trusted Anna to look after her as she was his Special Little Princess. His wife found fault with Stevie’s behavior and often spanked her hard until this time she went too far and spanked Stevie on her bare bottom with a leather paddle and a hairbrush! John returned home from business early the next day and discovered what had happened from Stevie’s tearful face and he gave his new wife her first ever severe spanking punishment. He was so angry that he spanked her hard on her bare bottom making it turn deep red quickly before using a Compliance Discipline Strap which stung like hell and made his wife cry. However, he hadn’t finished with her! In the finale of this film, there was a caning scene that left welts and marks Anna would not forget in a hurry! This was her learning a lesson the hard way: Not to touch Step-Daddy’s Precious Little Princess!

This is the full length version in best quality HD playback.
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Lily Starr Spanking – MP4/Full HD – SEVERE! Mom’s Painfully Poor Judgment: Mom & Schoolgirl Stepdaughter Punished Together By Dad For Lying By Omission – Miss Anna Spanked To Sobb (Exclusive)

Lily Starr Spanking – MP4/Full HD – SEVERE! Mom’s Painfully Poor Judgment: Mom & Schoolgirl Stepdaughter Punished Together By Dad For Lying By Omission – Miss Anna Spanked To Sobb (Exclusive)

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Lily Starr Spanking – MP4/Full HD – SEVERE! Mom’s Painfully Poor Judgment: Mom & Schoolgirl Stepdaughter Punished Together By Dad For Lying By Omission – Miss Anna Spanked To Sobb (Exclusive)

A few days prior, mom Anna was pulled over and given a speeding citation shortly after picking up her daughter Lily from her high school. She didn’t want her husband Robert to know about it, so she tucked the ticket away in her lingerie drawer and told Lily not to mention it to dad. He’d been doing some laundry, and in putting away some of his wife’s, stumbled on the hidden ticket. It was bad enough to learn that his wife is hiding things from him, but even worse, he noted the time the ticket was cited, and knew that Lily must have been there. This meant that not only did his wife endanger their daughter by speeding with her in the car, but his daughter was hiding things from him too. The two ladies of the house are relaxing in mom and dad’s room, when he comes in to confront them about his discovery. There’s not much denying it to be done, as he has seen the proof, so Anna can only ashamedly confess, promise that she intends to pay for it, and hope he doesn’t make a big deal of it. Lily is feeling very uncomfortable in the situation, and doesn’t understand why Daddy is so upset with her too, when she didn’t even do it! Robert lectures them both about the importance of honesty and working together, and is hurt that they would keep secrets from him that way. He also points out to Anna what a bad example she is setting, teaching Lily to be dishonest with her parents at an age when being open and honest with both of them is especially important. Lily thinks that because she didn’t tell lies, she didn’t do anything wrong, but he reminds her that lying by omission is still lying, and he won’t tolerate being lied to in his own house by his own family! Both girls are shocked when Dad tells them that he’s going to punish both of them, “the old fashioned way.” Since his wife was the main offender, and supposedly the responsible adult, she is going to be dealt with first and more harshly – a hard bare bottom spanking over his knee, followed by kneeling on the bench at the end of the bed for a hard strapping with the razor strop, followed by a merciless paddling with the heavy wooden bath brush! Meanwhile Lily has to stay in her chair witnessing the scene, wincing and squirming, knowing she is going to be spanked next. It’s very embarrassing for Anna to be spanked like a naughty little girl and break down sobbing in front of her daughter, and just as embarrassing for Lily to see her mom being spanked! Over her husband’s knee, Anna soon begins to cry from the hard hand spanking and the humiliating situation in which she finds herself. The strop and brush are even more intense, and result in Anna completely breaking down, sobbing, clutching the bedspread, screaming and begging. None of this is going to do her any good, Robert will only stop when he’s satisfied that her lesson has been learned. Lily feels terrible seeing this happening to her mom, but knows that too much protesting will only earn her a worse spanking too, and that when mom’s ends, hers begins. When he finishes with Anna, her bottom is heavily marked and very sore, and she is well past the point of tears, a true punishment spanking. Now it is Lily’s turn. When she stands up, Robert makes mom kneel in the chair she was sitting in, facing the corner with her spanked bare bottom displayed, while he deals with his little girl. Lily gets the same hard OTK bare bottom spanking mom got, but is spared the horrible strop and bath brush this time. Daddy lectures her about honesty, and makes sure that the message is gotten across that neither of them are ever to be deceitful with him again! This is a very intense domestic discipline scene with real tears, and a great choice for those who prefer to watch hard spankings with genuine reactions and tears! This version runs 25 minutes, and contains the entire scene in full with a bottom cam view of the spankings. This title is being released in two smaller portions for those who have a preference, or simply don’t care about (or want to pay for) seeing both angles. We have this full scene with bottom cam spanking, and coming very soon, the bonus reaction cam spanking footage. All in 1920 HD. As always, if you want to watch multiple titles but can’t afford all of the downloads, you can see every angle of every video I’ve released here in the past 8+ years for a much better value by opting for our unlimited monthly streaming membership via
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Lily Starr Spanking – MP4/Full HD – A Painful Lesson For Teacher: Miss Anna (Exclusive)

Lily Starr Spanking – MP4/Full HD – A Painful Lesson For Teacher: Miss Anna Spanked, Scolded, Paddled, And Caned To Tears By Lily Starr & Robert Wolf (Exclusive)

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Lily Starr Spanking – MP4/Full HD – A Painful Lesson For Teacher: Miss Anna (Exclusive)

Miss Anna is an old-fashioned schoolteacher from the Midwest, she grew up with spanking in school, and considers it normal. She is now living and teaching in California, and when a little girl in her class was caught being childish, giggling too much with her friends in class, she took it upon herself to call her to the front of the room and spank her bare bottom in front of the entire class, which was certainly humiliating. When she went home and told her parents, both very anti-spanking psychologists. They were livid, as they had not only never consented to this, their daughter was never normally in trouble, and it hasn’t even been legal in California for decades! Her mother, Lily, calls Anna and invites her over for a chat after school “about her daughter’s behavior.” Really, she wants to confront her face to face about the incident! Once the pleasantries of meeting are finished, Lily lets Anna know in no uncertain terms that what she did was not only unacceptable, it was illegal. Anna is very set in her ways, and continues to argue that she only did what she felt was best, and what she felt she had to do. Seeing a lack of any remorse, Lily is determined to knock this arrogant woman down a peg and teach her a lesson. Part of her would also like to humiliate her the way she did their daughter. Anna seemingly doesn’t know that it’s a big deal to spank in school in California, but as soon as Lily threatens to call District to report her, her tune changes and she wants to know what she can do to keep this quiet. Lily tells Anna that she thinks she deserves to be spanked herself for her inappropriate behavior, and intends to give her a spanking, as she “feels it’s what she has to do” to make sure she gives a sincere assurance that she will never put her hands on someone else’s girl or boy who she has been entrusted to educate again! Even once over Lily’s lap, Anna tries to give her some nonsense about how she has a degree in education and knows best, but when Lily makes it clear that she’s not going to be intimidated by her education when she has a doctorate herself, Anna finally for the most part accepts her fate. She does object when Lily pulls her panties down, but Lily has the upper hand in every way in the situation, and there’s not much Anna can do about it if she wants to keep her job. Lily is glad that she’s embarrassed, she hoped to embarrass her because of what she did. Since Anna used a ruler on their girl, Lily thinks she should experience at least that much, so she steps out of the room for a moment, and grabs a wooden spoon and a cane that she and her husband sometimes use during ADULT play. She orders Anna back over her lap and gives her bottom a good paddling with the spoon, then tells her to stand up, kneel on the couch, and stick out her bottom for the cane. As she is caning her exposed bare bottom, her husband Robert gets in from work, as she had hoped he would before she was through. Now she can really embarrass Anna! He completely agrees with his wife’s actions, and watches approvingly while she continues the caning, much to Anna’s horror. If that weren’t bad enough, Lily then offers him the cane, to let him have a whack at this awful woman too, so to speak. If she thought the spanking from Lily hurt, and it did, the spanking from Robert really gets her attention. He is angry about what she did to their daughter too, and not holding back! In fact, he hits her with such intensity that the cane’s tip can’t handle the impact and breaks off. Lily was not at all ready for this to be done, so she grabs the spoon again and just starts using that on her in the standing position. Once she has given her a good round of paddling, she offers the spoon to Robert to finish up, and he REALLY lays into her. Anna ended up sobbing with tears running down her face, and the spoon ended up cracking as well with this pissed off Daddy’s muscle behind it! Once they are satisfied that she’s been thoroughly punished and learned her lesson, she is asked to compose herself and leave their home ASAP, which she is eager to do. They are pretty certain that she will think twice before trying to pull something like this again. This format contains the scene intro, and then the shot is focused on Anna’s beautiful bottom, long legs, and high heels as she is being spanked. Reaction cam bonus footage is coming soon, and it is also pretty great because she was crying real tears and you can see a bit of the spanking from the angle it was shot at as well. 1080p HD
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Cheerleader Spankings – MP4/Full HD – John Osborne, Miss Anna – Spanked Like a Cheerleader Full Clip

Cheerleader Spankings – MP4/Full HD – John Osborne, Miss Anna – Spanked Like a Cheerleader Full Clip

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Cheerleader Spankings – MP4/Full HD – John Osborne, Miss Anna – Spanked Like a Cheerleader Full Clip

Miss Anna is excited to take on her new role as Assistant Coach and arrives to a meeting with the Head Coach wearing a cheerleader uniform. He realizes she has issues with discipline and knows the girls will not respect her looking like this. So if she enjoys looking like a cheerleader, he insists that she should experience what it is like to feel like a cheerleader that gets disciplined! Anna can take quite a punishment but even this spanking over his lap has her squirming and struggling as his hard hand relentlessly hits her cheeks until they are a dark, shameful red. She knows that all the girls get spanked on the bare bottom and feels what it is like to experience that same humiliating feeling as her panties are pulled down and the spankings continue. This is a really hard OTK hand spanking which is finished with some very painful strokes of the wooden “Bad Cheerleader” paddle. Anna now knows what it feels like to get a punishment as a cheerleader and won’t make the same mistake again.
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Triple A Spanking – AAA Spanking – MP4/Full HD – Miss Anna – Secrets Get You Spanked

Triple A Spanking – AAA Spanking – MP4/Full HD – Miss Anna – Secrets Get You Spanked

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Triple A Spanking – AAA Spanking – MP4/Full HD – Miss Anna – Secrets Get You Spanked

It had been some time since Anna and John had spent some quality time together so when it came to their playtime, John was upset to discover that Anna had been keeping a secret from him. "You’ve been seeing him again, haven’t you?" He could see the marks of a recent beating. Anna was so apologetic but John was incensed that she was keeping secrets like this. So he quickly dragged her over his lap and started to give her a hard hand spanking. Anna was already in her sexy lingerie and her long legs kicked as she struggled to take his angry spanking. This was just the start as he loved to use his favorite leather implements, a Reformatory Strap and thick, stiff gunbelt. However, there was to be no sensual spankings, just heavy licks of leather, reddening and marking her full round cheeks. John also knew that a hard discipline session turned them both on so by now he was past caring how he felt about her secrets and he used the heaviest, meanest bath brush at his disposal. This was a mean session with the brush that had her fighting back tears but John saved his best to last! Anna, was ordered to remove her bra, now naked… her full round breasts glistened as the adrenalin coursed through her body as it was time for her caning! Anna positioned herself over the bed for some of the meanest strokes she had ever received. With this over, John wanted to comfort Anna and provide the aftercare she needed. This was such a hot, mean spanking session so he used lots of soothing Arnica lotion, gently rubbing into her sore skin, with equally soothing words in her ear, tender cuddles, hugs and gentle kisses to remind her how much she meant to him. Don’t miss this long play, very grown up domestic spanking video between real life play partners!

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Spanking House Productions – MP4/Full HD – Christy Cutie, Miss Anna – University Woes for Christy

Spanking House Productions – MP4/Full HD – Christy Cutie, Miss Anna – University Woes for Christy

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Christy is called in by Mom Anna to discuss her poor academics, and behavior, during her Freshman year at University. Christy seems to think that Freshman year is nothing more than party time. Mom is very upset with her daughter as she knows that Christy is a smart girl who just isn’t applying herself to her lessons and classes. Furthermore, Mom is paying for University and is in no mood for her saucy daughter’s attitude and eye rolling!

Anna decides that the best way to remedy this situation is to take this naughty college girl over her knee for a long overdue spanking! First, Mom spanks a resisting Christy over her cute summer dress and panties, and then the dress comes up and the panties come down for a bare bottom, over the knee, disciplinary hand spanking with Mom’s strong arm. Though Christy resists, she isn’t going to get out of this spanking! Mom Anna continues to drive the point home with the hairbrush on Christy’s now-sore, bare, red bottom. Once the spanking is finished, Mom needs to step out to cool off and leaves Christy kneeling on the chair for embarrassing corner time, her burning bottom on display.
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Punishments Only – MP4/Full HD – Ditches Gets Spanked Outdoors

Punishments Only – MP4/Full HD – Ditches Gets Spanked Outdoors

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Anna and I have been looking after DD, helping her stay on track of her responsibilities and bettering herself. Then when Anna and I are out on a hike, we happen across DD when she is supposed to be at school. I am flabbergasted and very disappointed to find that she is cutting class to smoke with her friend Marika Lin. Catching them by surprise, Anna holds DD in place so she has to watch her friend get spanked first. I pull down Marika’s pants and spank her right there on the trail for anyone to see, then I send her on her way. (Unlike DD, she’s not under our care and I didn’t know if she was also cutting class, so a quick spanking is all I deem appropriate before sending her off.).

Now it is time for DD to be taught a lesson. Anna holds her steady as I pull down her pants and spank her, then Anna and I switch back and forth a couple times, scolding her intermittently. After this first spanking, we head back home, where DD is going to be punished further. On our way I decide to have DD grab a stick and turn it into a switch for her to be spanked with as well. Anna and I pull down her pants and both give DD a good switching before we get back home.

See the followup punishment when Anna and I get DD back home, available on DD’s store!
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Momma Spankings – MP4/Full HD – Sarah Gregory,Miss Anna – Auntie Knows Best (Part 1)

Momma Spankings – MP4/Full HD – Sarah Gregory,Miss Anna – Auntie Knows Best (Part 1)

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Momma Spankings – MP4/Full HD – Sarah Gregory,Miss Anna - Auntie Knows Best (Part 1)

Sarah has been sent to stay with her strict Aunt because her behavior is out of control and mom is at her wits end. Sarah is in for a rude awakening when she is woken up (mind you at 3 in the afternoon) and told that what she needs is some good old fashioned discipline for her rude behavior, skipping school, and general breaking of rules. Sarah is taken out her aunt’s knee for a hard hand and hairbrush spanking.
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Triple A Spanking – AAA Spanking – MP4/Full HD – Ten Amorette, Miss Anna – Spanked & Mouthsoaped by Mommy

Triple A Spanking – AAA Spanking – MP4/Full HD – Ten Amorette, Miss Anna – Spanked & Mouthsoaped by Mommy

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Warning: This is an intense "Mommy/Daughter" hard hand and hairbrush spanking with a finale only foul mouthed young ladies deserve. Ten Amorette is on the receiving end of a long, tearful and brutal mouthsoaping that she will not forget in a hurry. Mom (played by Miss Anna) takes her daughter over her lap for an overdue spanking with the continual disrespect and poor attitude capped by that filthy mouth of hers. When Ten swears and cusses further, Mommy takes her to the bathroom for another spanking whilst reminding her to take a look in the mirror at herself during the punishment. Ten shows no remorse and swears some more forcing Mommy to take the bar of soap, froth it up and make her daughter taste that awful sudsy, cleansing soap bar deep inside her mouth whilst being scolded. Ten finally learns her lesson after several cleansing sessions, her face and mouth a soapy, shameful mess. She will think twice about swearing in front of her mother in the future!
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