A few years ago, I had a cushy office job that came with an assistant. She was Jenny, an eighteen-year-old girl, and she was a godsend. Well-organized and disciplined, she kept things running smoothly. Of course, she was also a rather attractive young lady with an athletic build. She was also very warm and personable, and we became friends.
After a while, I started letting my own job slide. Jenny was smart enough that she had learned how to do my job, but not smart enough not to let herself fall into the trap of doing it for me. This had gone on for over a month and of course was getting old. She started threatening me with a spanking if I didn’t step up and do my job. I got the impression that it was mostly an idle threat, but not entirely. She just might do it.
Just the thought of her paddling my bare backside hard had a small impact. I started to step up. But this was fleeting. Each time she threatened me with a spanking made less of a difference than the time before, and for a shorter period.
My boss figured out what was happening. He fired me and promoted Jenny. Over the next few months, we kept in touch, and she could witness my continuing downward slide. Unable to find a new job, I not only got evicted for non-payment of rent, but I also got caught shoplifting just trying to get things I needed. These two things happened on the same day.
After a brief stint in jail, I came out with no place to go. Jenny stepped up and agreed to let me stay with her until I got back on my feet, having cleared this with her housemates. By this time, she was twenty-four and sharing a house with a couple of other young women, Sue and Kelly. I was fifty-five.
Kelly had been a sorority pledge master. She kept the paddle, and it was hanging in the living room. It was about a third of an inch thick, four inches wide, and a foot and a half long, with the Greek letters sigma nu painted on it, a dozen holes in it, and beveled edges for aerodynamics.
Over the next few days, I demonstrated myself to be messy and irresponsible, and wasn’t even looking for a job. Then I screwed up badly. I took Jenny’s car without permission and went to a bar. I drove home drunk at two am. I made enough noise entering the house that I woke up the whole house. Jenny was already up, trying to figure out what to do. She started yelling at me as the other two watched, nodding in agreement. In a strict, scolding tone, she ran down a laundry list of things I had already done wrong in just a few days. Then I pull a stunt like this. She talked to me like I was a little boy.
What could I say? “Sorry” didn't cut it but it was all I had. Then she said, “You're like a kid, but worse! I just don't know what to do! Can you tell me what I should do? I am out of ideas! Tell me!”
I answered, “I have an idea, but I'm afraid to say it. I'm afraid you might do it. It might be what I need.”
She threw up her hands like to say, “What? Spit it out!” but didn't get those words out. She noticed me eyeing the paddle hanging on the wall. She turned and looked at it, then turned back to me. “What? I should make good on my threats to give you half a dozen swats like a little boy?”
I wanted to plead with her not to do that, but I knew it was a good idea. I was shaking my head no but made myself give a different answer. I started, “I doubt that would be very effective …”
Without letting me finish, she went back to, “What, then? What are we going to do?”
I swallowed hard and then added, “To be effective, it would have to be harder, longer, and more embarrassing.”
She looked shocked but also looked like she kind of liked the idea. She was probably picturing me over her lap. I know I was. It scared me, but I had no better idea.
I couldn't keep looking at her; I looked at the floor and said, “Sue and Kelly can see you holding me accountable. I think I would respond well to corporal punishment. But it must really hurt. Like a lot, severe.” I was trying to say more but couldn't find the words. The next thing out of my mouth was just an extended “uhm.”
Jenny said, “Look at me!” I managed to look her in the face. Her smile was most likely equal parts knowing that I had come up with a practical solution and wanting to put me over her lap. Then she said, “We all need a little sleep first. When I tell you to, you are going to take off all your clothes and bring me the paddle. If I have to hold you down as I spank you, I will. I will give you the paddling of your life! If it takes corporal punishment for you to learn a lesson, I'm going to teach you a lesson you will never forget! For now, I'm going to bed, and I suggest you do the same. Meet me here in the living room a little before seven.”
It was a little after seven, and I was sound asleep. A small glass of cold water pouring over my head jarred me from my slumber. Jenny was standing there in the tank and shorts she slept in.
She pulled my hair and started scolding me like a little boy again. “I told you to meet me BEFORE SEVEN! C'mon, you're late for your spanking. Let's get it over with.” When I didn't move right away, she gave my ass a few hard smacks with her hand and said, “MOVE IT!”
I staggered into the living room still wearing my clothes from the night before. Jenny sat in the middle of the couch on the opposite side of the room from the paddle, Sue and Kelly sat in the chairs. They all looked at me, Jenny looking pissed off and the other two smiling devilishly. I just muttered, “What did I get myself into?”
Jenny scolded, “You know full well! Quit stalling! Let's get it over with!” I walked to the paddle and started to reach for it. She said, “Aren't you forgetting something?” I looked back at her. She gestured as she said, “The clothes. Take them off.”
I started to do as I was told and said, “Is this really necessary?” She just looked angry, but with just a hint of a grin. It might not have been necessary, but it was what she wanted. Her grin widened as I took off my clothes. I had stripped to nothing but my underpants and reached for the paddle again.
She said, “HEY! The boxers, too!” I looked at her as if to ask if she was serious. The look on her face was all the answer I needed. She moved her finger like she was trying to pull my underpants down telekinetically. “Everything must come off! Even the boxers!” As I took off my boxers, she grinned evilly. Pointing to indicate my penis, she said, “OK, I can see why you wouldn't want people to see that little pimple.” Sue and Kelly snickered.
Oh well, let them enjoy it. By this time, I was completely naked and had carried the paddle across the room. As I handed it to her, she began to run down a list of things I had done wrong. She started with the events that had led to my getting fired in the first place and ended with what had happened the night before. Still holding the paddle in one hand, she patted her lap with the other. I lay across her lap. She set the paddle down on my back and gave me a hard hand spanking while she talked about having to get me out of bed and make me take off my clothes. She said the added humiliation of being naked was part of my punishment. Then she picked up the paddle again, rested her hand on the small of my back, and brought the paddle down hard on my bare backside. Much harder than I expected.
I cried out loud, threw my hands over my butt, and started to jump to my feet. Jenny said, “Oh no, you don't!” In a quick, smooth motion, she pushed me back over her lap with my left arm pinned against her body. She put her right leg over my legs, effectively pinning them in place. With her left hand, she kept my right hand pinned to my back. This all took place in a fraction of a second, and she proceeded to deliver a second whack just as hard as the first. Crying out again, I tried to pull myself free but could barely squirm a little. Jenny yelled at me in a scolding tone as she continued to spank me.
“You're not going anywhere! You earned this! You know you need it! Stop being a brat! Take your punishment like a big boy!
With tears starting to roll down my face, I apologized profusely, begging Jenny to stop. She didn't even answer, just kept on spanking me hard.
As the number of whacks approached fifty, I was full on crying, promising with all my heart to be good from that point on, and still begging her to stop. I kept struggling to break free. She kept making it look easy to hold me in place and kept paddling me with all her superabundant strength.
I stopped struggling against Jenny and just went limp over her knee. I was wailing and sobbing loudly, still begging her to stop.
She stopped and laid the paddle on my back. As she did so, she said, “OK, now you finally stopped fighting me and are ready to take your punishment like a big boy? Good, we finally got here. Now your punishment can start so we can get it over with.” Giving me more hard hand slaps, “It's about damn time!” Then she started paddling me again.
I lost the ability to say actual words. As she continued to spank me, I started just screaming and howling at the top of my lungs. A fifty-five-year-old man pinned naked over the knee of my twenty-four-year-old former assistant, her scolding and paddling me until I'm screaming and howling at the top of my lungs, then paddling me some more.
She stopped long enough to say, “I think you've learned your lesson. But just to be sure ...” then she paddled me some more just as hard.
She slid out from under me and let me continue to lie on the couch crying my eyes out. She crouched next to me and gently stroked my back. She said, “You can do so much better. I hate to see what you're making of your life. I'm here to teach you to do better. You have a week to find a job, or you will be back over my lap. I’m going to give you a list of chores for the house, and you will do them or be back over my lap. No more drinking, or you will be back over my lap. I will put you over my lap any time I think you deserve it, at my sole discretion.”
The girls went on to start their day, and I just lay there howling and wailing for hours.