My most embarrassing spanking came the summer after high school graduation. My best friend, Dean, and I were doing odd jobs all over town to earn pocket money for college next fall. We mowed lawns, did landscaping, installed sprinklers...just all sorts of outside manual labor.
The benefits of our physical labor were really showing too. Since we usually just wore cutoffs when we worked, we both had deep dark tans, and were the most buffed up we've ever been.
One afternoon, after we mowed two lawns and vacuumed a pool, we were taking a break at my house. We had a some cold drinks and were hanging out in my room until it was time for our next job.
I don't know how the conversation turned to it, but Dean started teasing me about still getting spanked by my parents. Fortunately, he didn't know that my older sister was allowed to spank me sometimes too.
I wasn't very happy with the the topic, so I tried several times to change the subject, but Dean was on a roll. Not only could he not believe that I still got spanked at my age, but he couldn't believe that it would hurt enough to make any difference. After all,
"They give spankings to little kids. How bad can it be?"
Finally, my pride had had enough.
"You want to see what it's like?" I asked. "Bend over and put your hands on the seat of that chair. I'll show you what it's like."
He waved his hand casually in the air.
"Look, I didn't mean to piss you off. I'll drop it." he said.
"Bull_s_h_i_t_!", I stood up. "You think you're so tough? If you've got the balls, I dare you to stand up and take a spanking."
"Fine, you big pussy." He stood up, turned, and bent over in front of the chair. "Show me what you get when Mommy is mad at you."
I told him to drop his shorts because his cutoffs were too thick to feel any sting. He just shook his head and unzipped his shorts and stepped out of them.
Then, wearing nothing but white briefs, he resumed the position, bent over with his hands resting on the seat cushion. The white material, strethed across his butt clearing defined his hard cheeks and the cleft in between.
I felt a slight stir in my shorts, but I was too mad to focus on that yet.
I stepped over, and with my open hand, I started swinging on his ass. The house was empty, so I didn't care how much noise we made. The pops of my hand hitting his brief covered ass filled the room. I spanked as hard as I could. One cheek then the other.
After about 15 spanks, I noticed that he wasn't reacting much at all.
Noticing my pause, Dean looked over his shoulder at me,
"Is that it? That's what your parents give you to make you 'behave'? I'm not impressed." He said with a sneer and he started to get up.
Now I was really steamed. Whenever my parents, or sister, gave me a spanking, it hurt like hell. I would always end up kicking and screaming and promising never to do again, whatever got me in that position. I decided to give it to Dean the way I always got it.
"We're not done yet." I said.
I pushed him back over with one hand and hooked my fingers in the waistband of his briefs with the other. I yanked his underwear down to his knees. I couldn't help but notice how great his ass looked. His butt was round and hard. His tan line ran right along the bottom line of his ass cheeks from where his bathing suit stopped. I was more aware of the stirring in my shorts now.
"This is how I always get it."
Then I really started to let him have it. From the first spank, I was leaving hand prints on his ass.
I spanked one hard cheek and then the other. I had his attention now. As his ass got redder, he started to squirm a bit. I also noticed, that with each spank, his _d_i_c_k_ would flop up into my view. Although he didn't actually have an erection, I could see it getting bigger with each flop.
My own _d_i_c_k_ was at almost full attention. I could feel the strain of my shorts. I've never been attracted to Dean. I'm definitely straight. But slapping his ass and watching his _d_i_c_k_ flop up and down, was really turning me on.
Finally, he held his hand up.
"Ok, Mike, That's enough. You're killing me. I get your point."
He stood up and started rubbing his ass. As he faced me, I tried not to look at his half hard _d_i_c_k_. He bent over and pulled up his briefs.
"_d_a_m_n_, I'm glad my parents don't do that. I'd never be able to sit down at school."
"Fine," I said,"now you know what it's like. Can we just drop it now?"
"Not just yet." He said evenly. "Now it's your turn."
"I don't think so." I backed a step. "This was just a demonstration, for your education. I'm not getting spanked for no reason."
"No reason?? What the hell?? You think I'm just going to let you beat the hell out of me and call it even?? Bull_s_h_i_t_! Get your ass over here, i it's your turn."
I really didn't have a choice. Of course I couldn't just beat him and expect it to end there, although, I wish I had thought of that sooner.
"Fine, you're right. Fair is Fair." I stepped out of my cutoffs and stepped toward the chair.
I knew my underwear would have to come down, and already had my thumbs hooked in the waistband. My only concern, was Dean seeing my erection. I tried to angle myself away from him, and hoped he wouldn't see it when I bent over.
But before I could step next to the chair, Dean suddenly sat in it. I froze.
"I know how your parents give it to you. You have to lay over their lap. that's how I'm going to give it to you." He said sternly.
I still wasn't moving. I didn't know what to do. I was too shocked to even think clearly. Apparently, I waited too long, so Dean moved for me.
He leaned forward and grabbed the front of my briefs and yanked them down. My erection sprang out.
"That's what I thought," he said, pointing at my _d_i_c_k_. "You were getting off spanking me. Now you're really going to get it."
With my briefs bunched up at my knees, I didn't think it could get any more embarrassing. That is, until Dean reached over and grabbed me by my _d_i_c_k_ and pulled me over to him.
He used my _d_i_c_k_ to pull me over his lap, placing my hard-on right between his legs. He positioned me so that my _d_i_c_k_ hung between his legs, then clamped them together.
With my feet off the floor, and my raging hard-on clamped between Dean's legs, I wasn't going anywhere. Then it began...
Dean proved himself to be a quick study. He start spanking me with a vengence. I yelped on the first slap and after the first fifteen, I was fighting to keep my self control.
He spanked up one cheek and down the other. He spanked the lower cheeks, the center, and upper.
SMACK....SMACK.....SMACK....SMACK.....SMACK....SMACK....SMACK....SMACK...
He was relentless. With each spank, I yelped and squirmed. Everytime I squirmed, my _d_i_c_k_ was streched and squeezed between his legs.
SMACK....SMACK....SMACK....SMACK....SMACK....SMACK...SMACK....SMACK....
If things weren't bad enough. I could feel the pressure building up inside me. My hard-on was raging, and through the pain, I was so turned on that I was dying to explode. I kept trying to hold back. I couldn't let myself cum like this.
SMACK...SMACK...SMACK...
The stretching and pulling continued....the pressure continued to build.
Then he started spanking faster, my involuntary movements increased.
Finally, I was overcome. I started humping his lap as he spanked. The pressure and pleasure were so great, I couldn't help it any more.
He was spanking as fast as he could, and I was humping as fast as I could.
Then suddenly, I felt the surge come all the way from my toes...
With a loud growling groan, I shot my load right between his legs. As the sweat rolled off my back, I could see my cum shooting to the floor as I continued to pump and he continued to spank.
As the last couple of drops hit the floor, I lay panting over his lap.
"Is that usually how it goes?" Dean asked. Sounding rather pleased with \ himself.
"Well, no. Usually...." whatever I was about to say stuck in my throat.
As my vision started to clear, I found myself trying to focus on something. After having a mind shattering orgasm, and being upside down besides, I was having trouble focusing for a moment. Then I realized what was wrong.
Between my feet, I could see another pair of feet standing just inside the room.
Before I could move or say anything...
"No, it doesn't usually go like that," my sister said. "Usually, to make him cum like that, I have to stick a finger up his ass.
Then it was her turn to spank both of us...
But that's another story for another web page.
This is the first part of a longer story I'm working on. Later in the story, the mother oversees the daughter spanking both boys, then both boys spanking the daughter. Later still, the daughter bare ass spanks the father.
If you like this story, let me know and I'll work on some more M/M.