Miss Kelley is the office HR manager and is having to, once again, deal with the CEO's spoiled brat of a step-son. Milo has lived a life of privilege without consequences. He has swanned his way into this job straight out of college, but treating the job with about as much seriousness as a frat party. Unfortunately, given his step-father's job, Kelley hasn't been able to take any action to correct his behavior. Until one day Milo gets caught with things he shouldn't have in his desk drawer, and dear old step-dad decides he's tired of bailing him out. Milo is out of chances.
In "The ...
Miss Kelley is the office HR manager and is having to, once again, deal with the CEO's spoiled brat of a step-son. Milo has lived a life of privilege without consequences. He has swanned his way into this job straight out of college, but treating the job with about as much seriousness as a frat party. Unfortunately, given his step-father's job, Kelley hasn't been able to take any action to correct his behavior. Until one day Milo gets caught with things he shouldn't have in his desk drawer, and dear old step-dad decides he's tired of bailing him out. Milo is out of chances.
In "The CEO's Step-son: Out of Line and Out of Luck," the audience is treated to a gripping display of authority and discipline. As Kelley delivers a blistering scolding, Milo's audacity knows no bounds as he places his feet on Kelley's desk, arrogantly dismissing her concerns, and reminding her that he is the CEO's step-son. But Kelley is not one to be trifled with. She informs him that his step-father has washed his hands of bailing him out, leaving Milo with a stark choice: submit to Kelley's punishment or lose his job and allowance.
Obviously not able to go without his allowance, and assuming how bad could this spanking be, Milo chooses Kelley's way. The scene intensifies as Kelley takes Milo over her knee, delivering a humiliating spanking first over the seat of his jeans. Kelley then lets him know his warm up is done, and makes him stand with his hands on his head as she humiliatingly undoes his jeans for him, pulling them down to his knees. She then turns up the heat on his brightly colored childish briefs and then ultimately on his crimson bare bottom. Despite the sting of her hand, Milo's attitude remains defiant.
Kelley decides to escalate the discipline, telling Milo to hand her his own leather belt. She then bends him over the edge of her desk and proceeds to blister his bottom with that fancy belt he was so fond of bragging about. How embarrassing! The heavy belt lands stroke after stroke, a proper belting that leaves his bottom sore and his ego bruised.
Throughout the spanking and the belting, Kelley's scolding is relentless. She reminds Milo that his behavior reflects his character and challenges him to be better. Bending down close to his face, she ensures her words resonate, making it clear that this is just the beginning of his correction. Any more misbehavior and this is exactly where he will find himself again.
As the belting continues, the bratty comments cease, and Milo's demeanor shifts from defiance to contrition. Once he finally shows remorse, Kelley stands him up, embraces him, and sends him back to work with a stern warning and a newfound respect for the rules.
This transformative journey from spoiled brat to repentant employee is a masterclass in f/m spanking and corporate discipline. Watch as Miss Kelley May tames the untamable, leaving an indelible mark on both Milo's bottom and his conscience. Don't miss the chance to witness this new release, where order is restored, and a lesson is learned the hard way.
Milo's face is shown only briefly in profile throughout the video, and it would be easy to insert oneself into the fantasy. But this is also a tremendous debut for Milo whose wonderfully bratty attitude feels authentic and genuine, and whose ample bottom turns the most delightful shade of red.
