Miss Kelley May

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The Blame Game Part 1: You Get Spanked in Front of your Sister by your Mom - Miss Kelley May

When step-siblings Joey and Katie-Jane throw a party at the house, but only one gets caught…

Will Katie say anything to save her step-brother from this painful and embarrassing fate? Or let him take the blame?

Mom Kelley gets a phone call from the step-mom of one of your friends, apologizing on her step-son’s behalf. He was caught partying at their house over the weekend, which is certainly a surprise to Kelley! She confronts you and your step-sister Katie-Jane about the party, but much to your dismay, Katie denies knowing anything about it! Even though she planned it with you!

Mom Kelley scolds you thoroughly as you stand helpless in front of both women. She had been willing to let you and your step-sister stay home without a babysitter, but you betrayed her trust by hosting a party. You squirm in front of her, knowing how step-mom deals with naughty boys and girls.

With your sister still sitting on the couch, you are told to put your hands on your head. Step-mom plans to spank the truth out of you, and she doesn’t care one bit that your step-sister will witness your ordeal. This is too unfair, Joey/you protests! Katie also partied over the weekend! But Katie continues to deny any involvement, and Kelley wastes no time pulling Joey’s pants down to his ankles. She drags you down over her knee and begins spanking with brisk slaps over your briefs. Your embarrassment continues while step-mom Kelley scolds you and proceeds to bare your bottom. In front of Katie!

Swat after swat rain down as you wriggle and kick your feet trying to stop the onslaught. You whine about Katie-Jane watching the spanking, clearly embarrassed, but your step-mom is not amused. She declares that next time she goes out of town, Katie-Jane will be in charge of you. Mom Kelley holds you tightly by the hip as she spanks your sit spots hard. Finally, step-mom Kelley lets you up after he promises to never misbehave like this again. Grounded until further notice, humiliated, you scamper away to your room away from your highly amused sister.

This video is part 1 of 2 in the Blame Game series. It is a MUST see for any fans of embarrassment, humiliation, witnessed spankings, or voyeur scenes, with poor Joey suffering through Katie watching his entire spanking! You don’t see Joey’s face at any point (though he is referred to as Joseph on occasion), allowing you to easily insert yourself into the action. A classic domestic scene with bickering siblings. And don’t worry. Katie-Jane will get her comeuppance soon…

Joey Brown, Katie Jane, Kelley May

Resolution : 1920×1080
Duration : 00:07:14

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The Parent Teacher Conference Part 1: You get spanked by Kelley May as your Mom Katie Jane watches! - Miss Kelley May

Oh, you are in trouble now! Miss Kelley has called your mother Katie-Jane in for a parent/teacher conference to discuss your horrendous behavior. You have been consistently disrupting class, refusing to work, and instigating fights with fellow classmates! This will not be tolerated, and consequences will be swift.

Miss Kelley proposes that you are in most need of an old-fashioned spanking and your mother readily agrees. You are so embarassed! This is not how you wanted this parent-teacher conference to go!

You are required to stand in front of your strict teacher Miss Kelley and ask her to punish your naughty bottom.  You are bent over her knee and smacks rain down as your beautiful mother Katie Jane watches approvingly.  All too soon you are stood up and directed to ask Katie Jane to lower your shorts!  She happily obliges- reminding you that this is exactly what you deserve.  Back over Miss Kelley’s knee, your spanking continues, and your embarrassment rises.  You are again stood up and sent back to your mother to request that your underwear be lowered so your teacher can give you a proper bare bottom spanking. How humiliating! Arms crossed you go back over Miss Kelley’s knee where your pout does not go unnoticed, and your bottom quickly turns brighter shades of pink.  This is for your own good and your teacher and mother are taking the time to punish you because they both know you are capable of far better behavior.

Miss Kelley requests that your mother fetch her Attitude Adjuster paddle and it rapidly has the desired effect as it’s applied OTK to your reddening backside.  Your gasps and contrite “ow”s become more pronounced with each hard swat.  Feeling very sorry for yourself you might believe your punishment is over, but Miss Kelley has other plans.  She orders you to kneel up on the sofa as she removes her full grain leather belt! You must ask her to whip your sore bottom.  Here we have a lovely view of Miss Kelley’s denim clad bottom, but your eyes are facing the other way.

Your punishment finally concluded, your mother sends you to wait for her in the car, promising you a similar comeuppance at home.  Had you remained in listening range, you would have heard your mother confess to Miss Kelley that her own behavior is in need of some correction… but that's for part 2!

This video shows the faces of the ladies, but not the bottom, Joey, allowing you to imagine yourself in his place.  Fans of Miss Kelley May, Katie Jane, Joey Brown, F/m pairings, parent/teacher conference scenarios, witnessed punishments, being made to ask for a spanking, OTK spanking, OTK paddling, taking off the belt, bare bottom belting, and threats of future spankings will especially enjoy this clip.

Joey Brown, Katie Jane, Kelley May

Resolution : 1920x1080
Duration : 00:13:39

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Peeping Tom: You get scolded by Miss Kelley as your about to be spanked in front of Katie-Jane (POV) - Miss Kelley May

When you went to stay with Auntie Kelley for a weekend, you meet her pretty friend Katie-Jane, who is also spending the weekend at the house. You can’t resist sneaking a look at Katie as she changes from athletic wear into a lacy bra, silky panties, and black pantyhose. You are thrilled to catch a glimpse of her naked body before she dresses, but the moment ends abruptly when Auntie Kelley rounds the corner in the hallway. She is shocked to see her nephew peeping at her friend! Auntie Kelley drags you into Katie’s room, where Katie is embarrassed and upset with you.

When Auntie Kelley decides to punish you right in front of Katie, your heart sinks. But your humiliation has just begun… Katie suggests a bare bottom spanking for the peeping tom, and your aunt is all too willing to spank you in front of the house guest. You are deeply embarrassed when Auntie Kelley pulls your pants all the way down to your ankles, exposing your bare bottom and private parts to Katie and Auntie Kelley. However, Auntie Kelley doesn’t let your erection interfere with your punishment, although she does make note of it. She pulls you down over her knee as Katie stands to the side, graced with a front-row seat to your spanking.

If you enjoy POV videos, you will love this clip! It starts off with peeping tom voyeurism and ends with Katie playing the voyeur in a great bait and switch. Watch as Miss Kelley speaks and scolds directly into the camera in this video, with ample embarrassment and humiliation. It's shot entirely from the eyeline of you as the voyeur-- exactly as you would see it! This clip does not contain any actual spanking, and ends as the spanking would begin.

Katie Jane, Kelley May

Resolution : 1920x1080
Duration : 00:03:38

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Lilly’s Real-Life Discipline (tears!) (Full) – Miss Kelley May

Lilly and Kelley are long-time real life friends and play partners (Lilly is one of Kelley’s bridesmaids!), who have a special dynamic. Specifically, Kelley has been punishing Lilly for various real life offenses (speeding tickets, not wearing panties, being late to work, not wearing panties, not doing school work, not wearing panties, etc.) over the many years that they’ve been friends. It’s unfortunately been longer than normal since they last saw each other though, and Lilly is in need of one of their trademark heavy discipline scenes.

In the car back from dinner, Kelley asked Lilly what it was she thought she needed to be punished for. Lilly started rambling nervously, listing out small offenses, that seemed to be compounding, relating to her schoolwork– things that normally wouldn’t merit a hard punishment, but things Lilly was clearly feeling guilty about. “Enough,” Kelley interupted her. “I’ve heard enough. I know what we’re going to be doing.”

Back at the apartment, Kelley has Lilly laid out on the bed over pillows. The scene starts casually, while Kelley gathers implements and Lilly nervously chats as she waits for the impending punishment. Lilly has been in this position with Kelley many times before, and she knows that this is going to hurt. If you ask Kelley for a real punishment, she will give you one.

This video is just a straight through shot of the punishment scene, from start to finish. There is a glorious view of Lilly’s face and Kelley’s action, as well as one of Lilly’s poor bottom that turns from white, to pink, to a deep deep red. Lilly’s face is exceptionally emotive and you can really experience exactly what she’s going through, as the scene progresses from a stingy hand, to a wooden paddle, to Miss Kelley’s belt, to a series of straps, and ultimately, the tawse, school paddle, cane, and bathbrush. She goes from nervous giggles and little squeaks of ouch, to loud wails, and finally to wracking sobs with REAL TEARS.

Kelley scolds and lectures throughout, focusing on Lilly’s achievements thus far and how she is not going to fall at this final hurdle. Kelley has no intention of changing who Lilly is through punishment– and she would never want to. Kelley intends though, to make sure that Lilly feels thoroughly punished and forgiven so that she can start again with a clean slate. And also to make sure that Lilly thinks twice the next time she decides that she knows better than the professors…

This is a “real discipline” scene in more ways than one! It’s a hard, intense, at times severe spanking that is long and painful and ultimately results in Lilly’s REAL TEARS. Mascara streams down her cheeks at the end while Kelley holds her close, kissing her head, and comforting her. It is for real life offenses (not turning in a homework assignment, going on tiktok and chats when she should be studying, etc.) and nothing is made up or scripted.

But it’s also “real” discipline in that it is a perfect example of what an actual, healthy, loving, discipline dynamic looks like. While Lilly struggles, screams, and cries, it is clear the entire time that Lilly is actively consenting to this scene and that she trusts Kelley completely. This video does not feel or unsafe. It shows how a spanking can be incredibly hard, and emotions can be exceptionally real, while also being safe and supportive. Lilly wants this and needs this, and Kelley is going to give it to her because she loves her and wants what’s best for her. Always. The girls’ bond is clearest perhaps when Lilly bursts into tears not from a specific stroke, but from Kelley telling her how proud she is of her.

Note from Kelley: This is, I think, the best video I’ve ever made in terms of authentic content, and is a must for anyone who loves real discipline videos, or cares about real life dynamics. It’s been a goal for years to film us together just being us (as many people might have seen us play together at parties), because I knew it would be magic, and I’m so thrilled to finally be sharing this part of us with the world. It’s funny, it’s heartwarming, it’s intense, and it’s hot. Lilly suffers so beautifully! Her tear streaked face and red bottom are stunning, and her screams and cries are a delight for any spanking fetishist.

This video contains spankings with hand, small paddle, belt, straps, tawse, school paddle, cane, and bathbrush. It is severe, with moderate to heavy marking. There is scolding throughout, and aftercare is shown.

Kelley May, Lilly Calloway

Resolution : 1280×720
Duration : 00:32:43

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Mommy’s Firm Hand (Complete Saga) – Miss Kelley May

In this comprehensive disciplinary saga, I, Miss Kelley May, guide my little Lilly Calloway through a journey of correction and redemption. This two-part video captures the full arc of Lilly’s misbehavior and the loving, firm discipline that follows.

The story begins at a seemingly innocent Sunday brunch, where Lilly’s bratty antics disrupt the peaceful afternoon. As her Step-mommy, I warn her of the consequences of her actions, but her defiance leads us to an inevitable confrontation back at home. With a stern scolding and a promise of a bare bottom spanking, Lilly learns that Step-mommy’s rules are not to be taken lightly.

The first part of this saga, “Step-mommy’s Firm Hand,” sees Lilly pulled over my knee for a thorough spanking. Her cute Sunday dress and cotton panties are no match for the firm hand of discipline. Despite her protests, adorable faces and incredibly embarrassed whining, Lilly’s apologies fall short of true remorse. The spanking continues onto her bare bottom, her lovely round bottom turning bright pink. The spanking intensifies with the vintage ebony hairbrush, ensuring that the lesson is not soon forgotten. Lilly is told, however, that her punishment is not over and to go to her room and get changed into pjs for a bedtime spanking and an early light’s out.

As night falls, “Lilly’s Bedtime Spanking” unfolds with Lilly sitting on her bed, cuddling her teddy bear, and dressed in silky pajamas. The realization of her earlier transgressions weighs heavily on her heart. Gone is the defiant bratty girl from when I first dragged her into the house by her ear.

I enter the room to deliver the final chapter of her discipline, reinforcing the message that misbehavior will always have consequences. Lilly’s pajama shorts are swiftly removed, and her already sore bottom is once again bared for a punishment that will ensure obedience in the future. The otk hand spanking is hard and fast and her whines and cries are genuine as her bottom was already sore from her previous spanking as well. Her embarrassment at being bare bottom over her step-mommy’s knee getting spanked is soon overtaken by the pain in her backside.

Lilly is then told to once again go fetch the heavy wooden hairbrush, each smack echoing the importance of good behavior. Lilly’s tears and sincere apologies signal a true understanding of her actions. After the disciplinary measures are complete, I embrace Lilly, offering comfort and forgiveness. As I tuck her into bed, we share a tender moment that reaffirms our bond and the role of discipline in our loving dynamic.

This complete collection is perfect for those who appreciate the nuances of ageplay discipline, where firm correction is balanced with affection and forgiveness. Watch as Lilly transitions from a bratty, misbehaving little one to a contrite, well-loved girl who has learned her lesson under the guidance of Step-mommy’s firm hand.

Step-mommy’s Firm Hand (Complete Saga), naughty little Lilly Calloway spanked by Kelley May (ageplay, hairbrush, discipline)

Kelley May, Lilly Calloway

Resolution : 1920×1080
Duration : 00:17:19

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Bonfire Night: Addison spanked by Auntie Kelley for her skimpy outfit - Miss Kelley May

This video is all hand spankings and entirely over the knee! Over jean shorts, thong, and then bare. A true spanko classic!

Addison is a high school cheerleader staying at her Auntie Kelley’s house for a while, but she’s quickly realizing that her aunt is a lot stricter than what she’s used to.

When she comes downstairs dressed in daisy dukes and a skimpy halter top, ready to head out to the bonfire with her friends, Auntie Kelley is not impressed. Tanned and blonde, Addison is the epitome of a Texas beauty, but Kelley standing firm in her jeans, boots, and leather belt doesn’t think she needs to be showing off for the whole town.

Besides, Addison said she’d be studying for her chemistry test today.

After a bit of back and forth, Auntie Kelley has had enough. Addison needs a reminder of the rules in this house. She pulls Addison over her knee, and with her round bottom barely covered by those tiny shorts, there’s no hiding how vulnerable she is in this position (and exactly why Auntie Kelley thought they weren’t appropriate). Kelley scolds throughout, asking if there’s some football boy Addison is trying to impress with this outfit. Addison swears there isn’t—this is just what all the girls wear! But Kelley isn’t buying it.

A firm spanking begins over Addison’s snug jean shorts, but it doesn’t stop there. Soon, Kelley stands her up and tugs them down, revealing a skimpy thong that definitely doesn’t belong in her house. Addison is quickly pulled back over for more discipline, her smooth skin turning pink and then red under Kelley’s strict hand.

Despite her squirming, there’s no escaping Auntie Kelley’s lap. With a firm tug, the tiny thong is lowered, leaving Addison completely bared. Already embarrassed to be spanked like a naughty girl, the cheerleader now has no choice but to take her punishment, knowing full well that nothing is hidden from view in this position. Her intimate areas are on display for anyone to see.

By the time Kelley decides that Addison has learned her lesson, it’s clear that she won’t be going anywhere in that outfit tonight. Bottom rosy red and very sore, she’s stood up, given a warm hug, and sent upstairs to change lesson learned.

This was Addison’s first time filming a spanking scene, and she was absolutely wonderful! A gorgeous Texas beauty, she’s sure to be a favorite among traditional spanking fans. Her face is not shown at any point in this video, so if you enjoy a POV-style experience and want to imagine yourself over Auntie Kelley’s lap, this is the perfect scene for you! This is a realistic parental discipline style scene that is HAND ONLY and entirely OTK. It’s firm but not overly harsh– just enough to teach the girl a lesson. If you are looking for a severe video, this one isn’t for you. But if you like traditional spankings, Kelley’s southern/Texas step-mama style, and/or the pretty popular girl getting spanked you will love this video!

Bonfire Night: Addison spanked by Auntie Kelley for her skimpy outfit (OTK bare bottom, discipline, hand spanking)

Addison, Kelley May

Resolution : 1920×1080
Duration : 00:06:40

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