It had been many months since Deb or I had inflicted a punishment spanking on each other but I knew that I was pushing Deb’s buttons a little to hard. I had been moody and on a number of occasions had forgotten to do chores leaving more for Deb to handle. The final straw came when I reverted to old habits and had stayed out until after 2 am and not called to let my lover know.

I arrived home somewhat tipsy and was met my a fuming Deb who proceeded to lecture me on respect or in my case the apparent lack of same. Her final words brought a sense of dread.

“7:30 tomorrow night, Tom. You, the paddle and I will finish this discussion.”

Even when angry at each other, we slept together but few words were spoken and my attempts to cuddle were quickly rebuffed.

The next day, I had a difficult time concentrating on work as I painfully recalled my last discipline spanking over her knee with a hairbrush. I worried that tonight would be much worse as she had mentioned the paddle and that was larger and heavier than the hairbrush.

I sent Deb a text a noon telling her that I was bringing home her favourite take out and that I loved her. Her one word response “Okay” confirmed the fact that I was in deep shit.

I arrived home around 6 pm and set the table for dinner expecting her home in about 30 minutes. At 7 pm when I had not heard from her I started to worry and tried her cell but there was no answer. I kept calling every five minutes and just before 7 30 pm she answered sounding somewhat drawn. Deb explained that she had tripped on a curb and had sprained her wrist which was now bandaged, but was otherwise fine and would be home in 20 minutes.

I made a big fuss over her when she came home and after making sure she was really okay, fixed her a drink and dished up dinner. We chatted normally during dinner and after I washed up she said, “Tom, we have some unfinished business to attend to.”

“Butt -tt Deb," I stammered, “Your right hand is sprained, maybe you should delay sentence until it is properly healed.”

“Nice try, that will be almost a month. Lets see what I can do with my left hand. Go up to the bedroom and strip, I’ll be up shortly.”

Following Deb’s orders, I went to our bedroom and took off all my clothes- folding them neatly on the bed. Deb came in a few minutes holding the dreaded paddle in her left hand. She had me bend over the bed and took up position to begin the paddling. Normally, she would commence any punishment without delay but she was taking her time, scoping out the target.

I sensed her raising the paddle and readied myself for the blow, but when it came it was a fraction of what I had expected. Ten swats later when I had not even groaned in a frustrated tone, Deb said, “This is not having any effect. Lie flat on the bed.”

I did as instructed and Deb raised the paddle high over her head and brought it down with a smack on my butt. This was definitely harder than the proceeding swats but nothing close to what I had experienced before from Deb. As soon as it started, I knew I was making a huge error in judgement but it was to late. I started to laugh and laugh hard almost to the point of tears. The effect was immediate, Deb tossed the paddle on the bed and stormed out without saying a word.

Still naked, I ran out of the room to apologize, but only caught a glimpse of her going through the front door. I waited 5 minutes and then tried her cell but there was no answer. More attempts had the same results. Ninety minutes later my cell rang and the ring tone indicated it was Deb.

“Deb, where are you?”

“Tom, shut up and listen very carefully. I’m at Cindy’s. Be here in 20 minutes and bring the paddle.” The dead air indicated she had already hung up.

Cindy is Deb’s baby sister and at 19 is almost 11 years younger than both Deb and I. She is almost 5’10’’ with long dark hair, smoking hot and very fit. I had fantasized about her on more than one occasion. She has bad luck with guys and is presently not seeing anyone.

I dressed quickly, put the paddle in a gym bag and headed for my car. I had no clue what Deb was up and my only thought she was going to have another crack at my butt. There was no way I was going to get spanked in front of Cindy.

Arriving at Cindy’s house, I knocked on the front door. After a minute or so it was opened by Cindy wearing tight cut off jeans and a low cut blouse showing off her ample boobs. Normally, she would have greeted me with a tight hug, but she just tilted her head to the right and said, “Well, Tommy boy, you sure pissed off my big sister. Guess you better come in.”

Deb was sitting on the couch stone faced and it appeared as it she had been crying. I knew I was in serious trouble.

"Deb, I am so so sorry, can we please go home and discuss this?”

“No Tom, there is nothing to discuss. You are going to receive the mother off all punishments. Hand me the paddle.”

“Deb, get real. You know that you can’t punish me properly in your condition.”

“You’re normally quicker Tom,” she smirked. “I’m not going to punish you, Cindy is!”

“You must be kidding. No way! She a little more than a kid and she your baby sister.”

“Listen up, smart boy. Cindy is well aware of our punishment arrangements and actually adopted them with her last boyfriend. I promise you, she knows how to swing a paddle! Oh, and for the record, I have noticed the way you ogle Cindy. More importantly, Tom, this is NOT an debate. You agree to be punished by Cindy or you and I are going to have serious relationship issues.”

“What does that mean?”

“It means Tom, that we won’t be seeing each other for a while.”

I knew my back was to the wall with no place to go. I was somewhat pissed that Deb discussed our sex life with her little sister but this was not the time to raise it. I nodded and said “Fine, lets get this over with.”

Looking at Cindy, Deb asked “Where do you want to do this, sis”

“The bedroom. Lets go Tom, bring the gym bag.”

Deb took the bag from me as we entered the bedroom and quickly removed the paddle. Handing it to Cindy she said, “he’s all yours!” and went and sat in a lounge chair close to the bed so that she could observe all the action.

Feeling the paddle in her hand, Cindy exclaimed, “Not bad, but if this does not do the trick, I have something that definitely will.”

“Tom, time to get naked” Cindy said as she swished the paddle in the air.

I looked at the two ladies and knowing that they were not about to change their mind, started to remove my clothes. As I stepped out of my slacks, I realized that I had a sizable erection bulging in my underwear and left them on. I guess Cindy did not appreciate the delay and the paddle cracked across my butt; I had not even seen it coming.

“Shit, that hurts,” I bellowed.

“What part of get naked did you not understand?” Cindy growled.

I had my underwear off in less than 2 seconds and stood with my hands in front of my full on boner.

“Hands by your side,” Cindy said firmly.

Cindy approached me and tapping my member with the paddle turned to Deb and asked “Does he get like this every time you punish him?”

“Sometimes, but that ones looks pretty special. Maybe he’s turned on by the thought of you spanking him,” Deb said with a grin.

“Oh really. Tom, do you think this is going to be fun?” Cindy asked as she pushed her face into mine.

“It could be if you and Deb would just chill at bit,” I said with a best boyish grin.

Before I knew what was happening, Cindy had grabbed me by my swollen dick and squeezing hard, looked me straight in the eye and said “You must have shit for brains Tom. You are naked, with your dick in a vice and I am holding a paddle.”

Tossing the paddle onto the bed she led me to the bed and in one fluid motion, she had me across her lap and was spanking my bottom, hard with her bare hand.. It did not take long for me to realize that she was deadly serious about the job at hand and I began to squirm and beg for her to stop.

“Save you whining Tom, this is just a prelude to the main event.” After about 5 minutes the spanking stopped and she ordered me to stand up.

Deb laughed as she saw my erection was still going strong.

“Hey sis, I guess his pecker did not get the message that what you were doing was punishment.”

“That’s because men have small brains and an erection shrinks it even smaller masking the pain. Deb, fetch a towel from the bathroom please.”

Unfolding the towel and placing it at the foot of the bed, Cindy looked at Deb and said “Men are more docile once they have unloaded. Look and learn, Sis.”

Turning her attention back to me, Cindy bent me over the towel and said, “jerk yourself off.”

“Are you out of your fucking mind?” I screamed as I stood up to face her.

Cindy grabbed my cock again and squeezed hard enough to make me wince in pain. “Don’t yell at me, every. Do you understand?”

“Sorry, Sorry, Sorry.”

“Good boy, now you are going to bed over the bed and start to jerk off and I am going to paddle you. Your job is to jerk off to the rhythm of the swats. I am going to start off slowly and then increase speed. The faster I go the quicker you stroke. Got it.?"

By this time Deb and stood up and joined Cindy and I by the bed. With a pleading look, I begged, “Deb, just the paddle please. Don’t let her do this.”

Without a moments thought she turned me around and bent me over the bed. She guided my right hand to my cock. “Do what Cindy says, Tom.” Deb said and returned to her seat.

The first swat came quickly and was followed by another about two seconds later. I started to stroke slowly as the paddling continued. Although each swat hurt ; I had taken harder in the past from Deb but I also knew that if this kept up for a long time time my butt would be a mess. The frequency increased for the next 10 - 15 strokes and I managed to keep pace. My breathing became more shallow and it was obvious that Cindy was keep a close eye on my progress.

“Let me know when you are about to come, Okay?” Cindy said as she landed another swat.

“Yes," I answered, knowing that the fight was already out of me.

The frequency increased again and each swat hurt more as they were landing on an already sore butt in almost the same spot. Damn, this girl was good. My stroke speed increased and I knew I was less that 30 seconds away from climax.

 “I’m coming.”

Cindy increase the stroke speed once more and I continued to pound away with more vigour. A few seconds later, a loud moan emerged from my lips. My knees buckled slightly and I blew my load on the towel. I felt like I shot cum for ever. My climax was acknowledged by an extremely hard swat that caused me to scream out in pain.

“Shit - that really hurt. What was that for?” I wined.

Without answering my questions Cindy spoke softy “Clean yourself up and stand up.”

I used a clean part of the towel and wiped myself clean and stood to face Cindy. I had not been full on crying but there were tears in my eyes. “Are you learning something here today, Tom.” Cindy continued in a softer voice.

“Yes, I sorry for my bad attitude and the pain I caused Deb.”

The girls looked at each other with a message that only close sisters could understand.

“Does his butt need any more punishment, Deb? It’s a nice shade of red. Any more and he may have some bruising that lasts a few days.”

Having risen from her seat, Deb walked behind me and ran the tip of her fingers tips across my red and wrinkled butt. “Cindy, one a scale of 1- 10 how hard were you swatting.”

‘The last was a solid 10, the ones before were about 7 - 8.”

Moving to face me directly, Deb stroked my cheek and said, “we’re almost done. Now that you are not so arrogant we can finish this off quickly.”

Turning back to Cindy she said “Give him 6 more like the last. A bruise or two is fine my me. Maybe the message will really sink in!”

Cindy looked at the paddle in her hand and said, “I think I will use my special paddle for the grand finale.”

Walking to her closet she extracted a wooden paddle from the top shelf. It was slightly larger in size and darker in colour but the main difference was a number of holes drilled into the paddle face. “The holes prevent any air resistance from cushioning the blow.” Cindy said with a wicked grin. Handing the paddle to Deb she said, "you should get yourself one of these little babies."

Deb examined the paddle with a great deal of interest and switched it around a few times.

“Thanks, I think I will,” she said as she handed the paddle back to Cindy.

I begged and pleaded but it was to no avail and I was quickly bent back over the bed. This time there was no sign on any erection. The little guy was far too scared.

“Tom, count them out loud.” Cindy instructed.

Swat “One” I wailed. The pain was unlike anything I had every experienced before and I felt it continue to build as the next two landed.

Swat - Swat. “Two, Three … Oh my God, please I can’t take any more.”

My legs started to tremble.

“Hang in there Tom.” Cindy said, “You’re halfway there.”

Swat - Swat. My legs started to fold and I fell against the bed with tears running down my cheeks.

“Back in position, and stick out that butt. One more to go, let see if we can make it extra special.”

I was unable to get the words out of my mouth. My butt was already on fire - what the fuck was extra special. I rose slowly and stuck out my butt once again.

“Take a deep breath, Tom.”

I did as instructed and slowly let it out.

“One more time.”

Again, I did as instructed and as I was exhaling, I heard the switch of the incoming paddle.

Swat. The pain was beyond imagination and I felt it pulse through every part of my body as I collapsed on the bed.

I knew I was bawling and had a vague memory of someone rubbing cream on my butt. “This will help Tom but you are going to be sore for days.”

I lay there for over 30 minutes until I was able to get up and rinse my face in the bathroom. I turned to examine my butt in the mirror and was horrified to see a deep red butt with a number of purple blotches. I dressed gingerly and walked slowly and painfully to the living room where the girls were having a glass of wine.

“Would you like a drink, Tom.” Cindy asked.

“No thanks, I would really like to go home.”

“I understand,” Cindy said as she stood up and gave me a tight hug. “I love you Tom. You handled that pretty well. Take care of my big sister, you probably don’t want me helping her out again, do you?"

I actually chuckled and said, “I don’t think my butt can take any more of your help but thanks for stepping in to lend a hand to Deb. I know I deserved it.”

“That’s progress,” Deb said as she came over and gave me a hug and a deep kiss on the lips.

“Lets go home.”

As we were heading out the door, I turned to the girls and said,

“Fate can be a cruel master - some day, you will find the tables get turned.”

Cindy giggled and said in her most sultry voice, “Bring it on, Tom. Bring it on.”