For me, it's a tie, between a severe razor strop whipping from my dad when I was a sophomore in high school (15 years old) and an equally severe bath brush paddling from my girlfriend just a few months ago. I'll write about the razor strop now, and write about the bath brush some other time.
When I was 15 (a high school sophomore), I was fortunate to date a 16 year old high school junior (I'll call her Nancy). Shortly after we started dating I invited her to study math at my house after school. When we arrived at my house, my mom greeted us and reminded me to finish my "barn chores" before it got dark (we lived on about 3 acres of land in rural New Mexico). So, Nancy and I went out to the barn to feed and water our two horses and chop some wood. The barn served not only as a barn, but also as my dad's workshop and our woodshed, and it was also my job to keep the entire barn clean.
Nancy's family also had horses, so she took care of them, while I tidied up the workshop and chopped some wood. Nancy finished with the horses before I was done, so she joined me in the woodshed section of the barn. Nancy and I were chatting as I was stacking the wood that I had chopped. At one point, I made a comment or asked a question, but Nancy didn't respond. I turned around and saw Nancy holding my dad's old razor strop... not the one he used for sharpening his straight razor... the one he used for sharpening behaviors and attitudes!
"Does your dad use this on you and your sisters?"
I was a little bit embarrassed, so I acknowledged somewhat sheepishly that my dad used that strop to punish us. Nancy was extremely curious...
"When was the last time you got a whuppin?"
"About a month ago."
"What did you do wrong?"
"I got a D on a math test. Which is why I want to study math with you!"
"Do you get in on the bare?"
"Yes, I always get it on my bare bottom."
"And your dad gives your sister's whuppins too?"
"Yes, but they usually get to keep their blue jeans on. If they're really naughty, they might get it across their panties. But never on the bare. Does your dad use a strop?"
"No. He uses a paddle. My brothers get it on the bare, but I get it across my blue jeans or panties. I wonder why boys get it on the bare, but not girls? Doesn't seem fair."
"I dunno."
"If I"m a naughty girl, will you use your dad's strop on my bare bottom?"
"WHAT?"
"I'm serious! I'm going to be naughty and I want you to give me a bare bottom whuppin with your dad's strop."
"You're kidding!?"
"No! I'm serious!"
"When?"
"Now."
"But you haven't done anything naughty."
"Take off your clothes."
"WHY?!"
"So I can do something naughty."
At this point, I was becoming aroused and threw caution to the wind.
"What are you going to do? Give me a whuppin?"
"No. I'm going to give you a handjob. And then you're going to give me a whuppin."
At this point, I didn't have a chance to respond before Nancy was undressing me. I was so aroused that I just kept my mouth shut. She stripped me completely naked and went to work on my rock hard erection. When I was just moments away from an orgasm, I asked Nancy to stop so I could undress her. Soon she was standing before me wearing nothing but her bra and panties. She removed her bra for me and I almost had a spontaneous orgasm just from seeing her perfect bare breasts.
"Do you want to fondle my breasts?"
"Yes ma'am!"
As I started fondling, Nancy picked up where she had left off with my handjob. Within rwo minutes, I had the most explosive orgasm of my life!
"I've been very naughty. I'm ready for my whuppin."
"Bring me the strop, young lady!"
"Yes sir."
"Remove your panties and straddle yourself across the sawhorse."
"Yes sir. Please don't go easy on me. I've been a bad girl and I deserve to have my bare bottom scorched."
"Are you sure?"
"What's the most licks you've ever received from your dad?"
"40."
"I want 40. I'll tell you to stop if I just can't handle it."
"Okay. Bend over."
"Yes sir."
At this point, I started whuppin Nancy's ass. As I was administering #32, my dad walked into the barn.
"Get dressed, young lady."
"Yes, Mr. Smith."
At this point, I started to get dressed also...
"Not you, young man. You can hand me the strop and straddle yourself across the sawhorse."
"I should probably leave now, Mr. Smith."
"No. You stand there and watch me blister John's bottom. In fact, you can count the licks he receives out loud."
"Yes sir."
"One... Two... Three... Ten... Thirty... Fifty... Fifty Eight... Fifty Nine... SIXTY."
"Thank you for counting young lady. You can go home now. By the time you get there, I will have spoken to your dad."
Nancy and I saw each other in math class the next day. I told her that my dad had taken me out to the barn before breakfast for 10 more licks with the strop, and I would be receiving 10 every morning for 10 days. She told me that her dad had given her 25 swats with his paddle (on top of the stropping that I had given her)... on her bare bottom. She also told me that she was very sorry for getting me in trouble...
"John, it was very naughty of me to get you in trouble. I think you need to discipline me."