Learning……..The Hard Way!

Found this one in the vault. It was written by a friend of mine a few centuries ago. We enjoyed paddling each other for several years.

With downcast eyes he stood there. Her heels clicked on the hardwood floors as she went over and then dragged back the plain oak chair. Although armless, it was a sturdy chair that would serve her purpose well. She placed the chair in front of the desk near the center of the room. She looked at him for his remorse in what he had done. All he wanted was for this to be over, but she seemed intent on taking her time.

“Bend over the chair, placing your palms flat on the seat.”

“Please don’t do this,” his eyes pleaded with hers. She smiled wordlessly at him and then told him motioned with her hand for him to bend over.

He placed his left hand firmly on the chair and then his right hand. His bottom was high in the air.

She responded with a “Good Boy” as he heard her footsteps once again. She was walking over to the desk and opening a drawer. He tried to twist his head to see what she was doing but knew better than to get out of position.

She walked around in front of him and he gasped as he saw that she was holding the paddle. This wasn’t just any paddle…..it was the paddle that was saved for the naughtiest of deeds. Surely, what he had done couldn’t be worthy of receiving it. Across this paddle was written, “Learning……..The Hard Way!” He felt his knees go weak as he looked at the paddle. It seemed unnecessarily large. The wood was very dark and smooth. He wondered if the sheen of the paddle was due to some sort of varnish or from frequent use. There were numerous tiny holes drilled all over the paddle. With a sick feeling in his stomach, he realized that the purpose of the holes was to allow a harder stroke.

After gasping at the awesome instrument of discipline, he kept whispering to himself, “no, no, no” as if to ward off the punishment.

She placed her hand on the small of his back and pressed the flat board against his jean-clad bottom. He clenched his teeth as he waited for the first stinging swat. She paused and said, “My dear boy, this just won’t do. Stand up and take down those pants. “No, please, anything else but……..” Do as your told! She interrupted him. He reluctantly stood back up and reached to remove his belt. Quickly, she added to the command. He undid the belt and unbuttoned his jeans. The zipper came down and he reached his thumbs inside the waistband of his jeans and pulled them down. They fell down to his knees. His underwear slipped a little and he reached to pull them back up.

“Move your hands, young man.” He complied. “When I told you to pull down your pants I meant, your briefs too.” She slipped her hand inside the band and slowly pulled them down. The briefs fall down his legs until they join the jeans at his knees.

“Now back in position!” He bent back over the dark wooden chair knowing that any defiance would just make it worse. Her foot kicked at his ankles lightly, indicating to move his legs more widely apart. She knew this vulnerable stance would heighten his punishment.

She lifted up his shirttail and carefully folded it back. She pressed the paddle against his bare bottom and rubbed it across his skin. “Feel the paddle against your skin. It feels cool to you now, but it a minute I am going to use it to set your bottom on fire.”

And with that, she raised it high behind her and brought it down on his left cheek hard! WHACK!!!!!! His head jerked up and he arched his back, just in time to receive another WHACK on his right cheek.

“I expect you to show up ON time (WHACK), do all your work (SMACK) and not be such a smart ass (WHACK)”. The next few spanks are hard and fast and are laid down over the middle part of his bottom. His legs began to kick up.

“I think it’s been far too long since you’ve had your bottom warmed properly!”

He mumbled something under his breath and she brought down the paddle with a thundering WHACK against his bare backside. “I don’t think I heard your response but I am sure it wasn’t acceptable.” She brought the dark wood down against his already burning bottom. WHACK!!!!!

“I expect a proper answer when I ask you a question. I will repeat it for your benefit. I think it’s been way too long since you’ve had your bottom fired up like this for your naughty behavior. Don’t you agree?” She punctuated her question with a burning swat. WHACK!!!!!

“YES, ma’am.”

“Much better.” She continued the flurry of swats until she was satisfied. “You may stand now and pull up your underwear and jeans. He took a deep breath and did as he was told.

Once his belt was pulled tight and fastened, he turned to face her. “I expect to see you in my office again at the same time next week. Do you understand?”

“Yes ma’am.”

“Good. I am glad we understand each other. I will not have you pulling any sort of smart ass antics around here. I am in charge and will not tolerate such behavior. Now, you are free to go.”

It was only then did he really notice her. A no-nonsense businesswoman who enjoyed her power. She dressed in a short blue skirt with a white blouse and short heels. She was filled with piss and vinegar and he knew he had met his match. But somehow he also knew this summer internship was going to be literally…………a pain in the ass!!

“Learning………the Hard Way” – Part II

The weekend was over and he was facing the Monday morning meeting- something he dreaded. He knew that he should have attended summer school instead of taking this internship. Somehow he thought working under a woman would be easy. He was beginning to learn that he was wrong.

Ms. Masters reminded him of a teacher he had in school. His mind wandered back to his earlier school days…… He was always in trouble then. Always told he was misbehaving. Serious infractions were punished by seven strokes of the paddle on his bottom at the principal’s office. His were sometimes bare-bottomed. Made to bend over and grab his ankles while the paddle was applied. The seven strokes were delivered at about five-second intervals………

The others started gathering in the Board Room, and she walked in last, closing the door behind her. He tried not to look at her. He had defied her authority on several occasions, and each time she threatened him to kick him out of the program.

“This will be quick people,” she started off, “we have a busy week ahead and I have a folder here for each of you. It contains your assignments for the week. Each day is outlined as to your specific responsibility. I expect these to be carried out as written.” She walked around to each person and handed them the folder. Most just quickly opened them up and then shut them again; obviously to be digested lately. “Does anyone have any questions?”

He did not get a folder. “Uh, yes, Ms. Masters, where are my assignments?”

“Oh, yes, Don, I almost forget. You have the best assignment of all. How could I have forgotten!!” She pulled out a red folder from the stack of blue ones and handed it to him. “Read it carefully, mister, no more mistakes will be tolerated!” He felt embarrassed by being pointed out like that. The others just chuckled under their breath. He had gained quite a reputation in the few short weeks that he had worked at Applied Training Co.

After the meeting, he found himself a quiet cubicle and sat down to review his assignments. There was only one piece of paper in the folder that said, “MONDAY” and underneath it said…..”Your assignment for today is to go to the janitorial closet and find a box that is marked ‘Arianna Masters’. You will choose carefully from the contents of this box and do what’s called for. You will then take the rest of the contents down to my car and then report to MY office at exactly 4:45pm. No mistakes, no tardiness, no breaks, will be permitted.” That was it. There were no further instructions. That was it? They were gonna pay him for today to just pretty much goof off?? Well, might as well get started………

He wandered down the hallway. He must have passed the janitorial closet a million times before, but for some reason, today was having trouble finding it. Finally, after searching for a while, he found it. He twisted the handle and it opened the door. The room was little but easily walked into. He felt around in the dark for a light or a light switch. He felt a chain hanging in the middle of the room, and he yanked it. The light permeated the musky room. His eyes adjusted to the light and he looked around. There it was in the corner……a box marked in big red letters – ARIANNA MASTERS. “Thank Goodness,” he thought. Maybe I will make a late lunch after all.

He pulled the box to the middle of the floor and opened it. He adjusted his eyes and blinked several times to clear his clouded vision. Inside were all sorts of panties. Lacy bright white satin panties, yellow full cotton briefs, pink nylon lycra bikinis and light blue sheer lace thongs.

He thought he had the wrong box, but there were no others in the room. His heart sank. She can’t mean for me to put on a pair of these!! The note pinned to the top of the pantie pile said, “Your choice!! One pair is all you will need to wear!!” He couldn’t believe this was happening. He would be too embarrassed to wear a pair of ladies’ panties all day……even until he went to her office at the end of the day. And yes, he would have to show up in her office with them on!! He started to feel warm and didn’t know what to do.

“SHIT! Well, no one will know I suppose. No one but her.” He looked through the box and choose the white satin panties. Quickly he pulled them up, savoring the silky feel around his penis and balls. He felt all sexy in them. He began to think that the pantie punishment wasn’t nearly as bad as he had imagined.

He pulled up his pants over the panties and picked up the box and left. Her car was on the other side of the parking lot and it took him way too long to find it. The backseat door was open and he laid the box on top of the leather. The weather was warm and he could feel the satin rubbing and sticking to his bottom. He looked at his watch. He needed to hurry if he was to meet Ms. Masters in her office……..

He walked through the door that led into the outer office. He glided passed her assistant. Looking over her horn-rimmed glasses, she said “You should consider yourself lucky. She deserves better young man…….. and she’s brought you here to be paddled for all your bad assignments.” What?? Did everyone know why he was there? He swallowed hard. Did that mean she knew about the panties? How humiliating.

He looked at his watch 5:05. The door to HER private office was locked. Maybe something had happened, maybe she wouldn’t come and he could leave. He waited around another five minutes and then walked to the door to leave.

“Where do you think you’re going, Don? Follow me, Mister.”

He followed behind her, which he didn’t mind. He loved to watch her sway her hips and adored her bottom in the short skirts she wore. He stepped into her office and she locked the door behind them.

Her office was immense. There was a sofa and even a small bed for her to lie down on when the late-night hours turned into the wee hours of the morning.

“Impatient, thing aren’t you? That’s exactly what I hear. I also hear you’re out of control again, and I see it’s time for a little reminder before EVERYONE has a problem with your work.”

His only answer was a low-throated moan as he tensed waiting for the inevitable. Wasting no time and ignoring the silent pleas in his eyes, she told him to bend over and grab his knees. She walked over to the desk and opened up the drawer and pulled out a solid oak paddle. The kind that principals use for naughty young boys. He thought that he would never have to see one again. It’s been a long time since his bottom had been kissed by such a paddle.

She walked back around and positioned herself at his side making sure that she was in the best position to swing the paddle so that it makes contact only with his lower cheeks. She took a few practice swings, checking the paddle just before contact. Don grimaced, as he expected to feel a sting each time, but she just rubbed his ass with the paddle. When she was finally ready, she took the paddle back and swung it with quite some vigor making sure to swing through contact. Don jumped. Ms. Masters continued with the paddling with about two or three seconds between licks. After about ten licks, she asked him if she is being too hard on him. He answered truthfully, but nonetheless, she continued until 20 or so licks had been applied.

She placed the paddle in front of him and told him to remove his pants. He undid the button and zipper on his form-fitting trousers. He tugged a little but manages to pull them down and then drops them to his knees. He remembers now that he is wearing the panties and feels a flush of embarrassment fall across his face.

She grins, “The satin white panties huh? Do you like them?…………… You must or you wouldn’t have chosen to wear them.” She walked around him admiring the bottom that was in front of her clad in a pair of lady’s panties.

A bottom that was quickly turning red……but not as red as it was to become. She rubbed her hand over the panties, feeling the smoothness in her palm.

“Pull down your panties,” she ordered almost sweetly. “Yes, Ma’am”. He put his thumbs inside the elastic band and started to wiggle out the panties. They were a little tight and he had to maneuver his dick and balls through them. He pulled them down to around his knees. The whole incident started to get him aroused.

“Turn around then.” When he did his penis was at full erection.

“What?” You’re obviously not properly respectful. Turn back around I’m going to paddle you until that thing goes down. You know how to make it go down?”


“Don’t get sassy with me Mister. Just take care of it.” And she handed him a bottle of baby oil that she had in the drawer of her desk. She watched as he drizzled it over his penis.

“Now Start”, she said. She began to paddle him with a stroke about every five seconds as he began to rub and jerk his dick. He managed to look over his shoulder and she was alternately watching his ass turn bright red and his efforts upfront.

She then startled him by ordering him to take off the pants and panties and get up on the bed. “On all fours mister. Hands and knees on the bed and bottom in the air.” He did as he was told. Too stunned by the whole incident not to comply.

She pulled out a new paddle while he was getting in position on the bed.

“You haven’t taken care of that erection, so I will take care of it for you.” She reaches around him and grabs his dick in one hand and holds the red paddle in the other. She starts up again with his paddling. Slowly at first, and then increasing the intensity as she feels him close to cuming. Her hand slowly moves up and down the shaft and head of his penis. His aroused state intensifies and she increases the flurry of swats until his juices flow across the bed in streams.

His final moan indicates to her that he is spent and he falls to the bed. She places the paddle down on the floor beside the bed and sits next to him. She places a hand on his head and strokes his hair. He turns his face towards her as she says, “You know it was for your own good.” A simple yes was all he could manage and she sat with him and comforted him. They both knew that these were lessons that he would remember for a long time to come………….

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