In A Dilly Of A Pickle

“Come and hit some balls with me!”

The older neighbor from downstairs stood out in front of my balcony and called up to me. She was over fifty for sure but I don’t think she was sixty quite yet. She stood there in a cute short tennis dress and sunglasses. The weekly hours she put into exercise in the condo gym had paid off.

“Sorry, Sue, but I have this project I need to complete today.”

“Oh, c’mon, your eyes will go square if you spend anymore time looking at those screens.”

I did some design work for a number of companies and I had a project that was all but done. I needed to finalize one piece then send it off. Fifteen minutes but with the procrastination, it would take the whole day likely. But, if I accepted her invitation, that might do the trick.

“Tell you what. Come up and have a coffee while I finish the last piece and I’ll come along with you.”

“Yay!”

She actually said yay and bounded up the stairs to my second floor apartment. I watched her breasts bounce on each step as she sprang up, closer and closer to me.

“Thanks, Jeff, almost no one is available that I play with. With your tennis skills, you should give me a good run for my money.”

I played tennis through university at a decent level. Not quite good enough to go pro but enough to win tournaments regularly. That was years ago though.

“I don’t know, Sue. It’s been a while for sure. Hope I still know which end to hold.”

She was right in front of me when she smirked.

“Sure, sure.”

I made her a cup of espresso with my automatic machine and asked her to have a seat while I worked. With three huge monitors, it wasn’t long before she came to ask questions and make appreciative noises as I completed the task. Why I put it off for all this time, I had no idea, but with an email and a file transfer, I was done. My next project was due in a few days so I had a mid week break ahead of me. And to start it off, I’d be trying pickle ball for the first time. Sue had invited me multiple times over the last few weeks but work stopped me. Now, it didn’t.

“I got an extra paddle for you to play with. I think it will suit you well.”

Life size ping pong held little interest to me until Sue had invited me. She was a decade or two older, single, and the life of the complex. I’d met her before Halloween when she went door to door and insisted I volunteer to put up decorations. I couldn’t say no so I was up a ladder in no time. Same for Christmas. And New Years. And… and… and… I didn’t mind though as I filled some of the time I would have just worked through and let me meet others in the complex. She was popular with everyone there but seemed to gravitate to me. And now, with summer upon us, I was now her new pickle ball partner.

We were away in her convertible after I enjoyed a second coffee with her and pulled on shorts and a shirt to play. The club was close and deserted other than some octogenarians in a slow rally. This didn’t bode well at all. She spoke to the front desk guy and signed me in as a guest. My few things went into a locker and I met her on the deck that overlooked the courts. It was pretty nice with courts as far as the eye could see. We had one of the back courts in the shade and made our way to it. I figured she’d be a front court kind of gal but we were tucked away in the back.

She’d gone over the rules with me before and had sent a few basic YouTube videos to get me into it over the last couple of months but it was a lot different from tennis and after trying to sit back deep and bang my shots in, I realized that her ‘dink’ was more effective than my smash and I started to watch her play. She was very efficient at the game and saved a lot of energy whenever possible. I also watched her body move as she played which lost me even more points.

In her one piece dress, she looked great and she knew it. I watched as she went to the back of the court to get one of my errant smashes and when she bent over, it wasn’t tennis panties or compression shorts I saw. It was a piece of purple fabric between her cheeks that took my mind right off the game at hand. My older neighbor had just about mooned me on the pickle ball court and had turned and smiled at me.

“Getting warmed up? Can I go harder on you now?”

Her words inflamed me as she served again. I had started to catch on to some of the nuances so my tennis reactions became helpful as I moved her around the court. One particularly long lunge lifted her skirt again and I missed the point as she knocked the ball back over the net but got a full eyeful of the triangle under her skirt. I could sense she was tired and used that to press her a bit harder. I figured if she had to move more, she’d show more, too. And she did.

In a final lunge for the ball, she sprawled out on the court with her skirt up and over her butt. I could see the thong stand out proudly between her tanned cheeks but there was nothing else. She worked quickly to get up and I had turned away by the time she made it back to her feet.

“Let’s take a break and have something to drink, please.”

We found a seat at a covered table and enjoyed the fruit juice. It was a bit warmer now and pretty much everyone had left the courts. Even the staff were inside.

“See how much fun I am to play with, Jeff?”

I nodded my agreement and she smiled.

“How about we make this interesting going forward? You have the idea of how to play so want to make a bet for each point?”

“I don’t play for money, sorry.”

“Oh, I’m not talking about money, Jeff.”

“Then what?”

“A paddle across the rump for each lost point.”

“You have to be kidding?”

“Not at all. I lose a point, you give me a paddle. You lose a point, I paddle you. One stroke per point.”

She was either sharking me earlier or…

“All right then.”

We returned to the far court again and after she checked to see no one had come out, she took her first serve. Back and forth we went with me losing when I tried to hit it in the air while in the ‘kitchen’.

“That’s my point. Come to the net and turn.”

I honestly thought she was kidding when I felt the paddle impact on my ass. Fuck it hurt, too. I spun around to see her blush and giggle. I think she called out zero one one as the score but honestly I was just ready to smash the ball down to get revenge. In doing so, I lost the plot and stepped into the fucking no go zone again to find myself turned and smacked. It was more the loss of control that got me than the pain but I was embarrassed. Enough was enough. Time to play properly.

I let her keep score but I started to take each point as I thought about what I needed to do. The first point I won, she came slowly to the net. I’m not sure if she expected a light tap but I gave her what she gave me the first time.

“Owwwwwwwwwwwwwwwwww. But I’m an old woman…”

“Pull the other one, Sue. That was lighter than the first one you gave me.”

“Was it? Did I hit widdle Jeffy too hard?”

The smirk did it for me. She tried to play it off but I could tell she enjoyed this attempt to get my goat. What she didn’t realize is that this was exactly how I played opponents during college. Let them talk while I walked all over them.

Another point and another return to the net for her. I smacked her hard but not too hard. She went away as she rubbed her ass cheeks. And like that, I won eleven to two.

“You won. I’ve been playing for years and you won right off the bat. No fair with all that experience and skill and ability.”

She affected a fake pout but put her hands on the bench as she assumed what looked like a position to be spanked.

“What’s this?”

“I lost the game. You get to spank me twenty times.”

She turned her head back and looked at the bench.

“You may begin. I am ready.”

It didn’t appear that this was a joke so I played along.

“Sue, you lost so will receive twenty strokes of the paddle. It will hurt but you will get over it at some point. You can count and ask for the next each time.”

She turned to look over her shoulder at me in slight disbelief. Had I caught her by surprise?

“Please, sir, may I have the first stroke?”

Sir?

I laid the first stroke flat on both cheeks. She jumped a bit and put both hands back on her rump.

“One, Sir. Please may I have the next?”

The second was flat and on both cheeks again but slightly lower. This time though, she didn’t put her hands back but wiggled her ass.

“Two, Sir. Please let’s do another.”

We went on that way for the first ten. I could hear a gasp with each stroke but she didn’t pull her hands up from the bench at all after the first one. She had done this before.

“Ten, Sir. May I have a quick break and stand?”

She was much more docile in her facial expressions and flushed on the cheeks. The courts were still deserted but I would have kept it up regardless.

“I’m ready for the next half but could I… could I…”

“Could you what, Sue?”

“Could I take these on my bare bottom? I have my thong on so my cheeks are free.”

Without a pause for an answer, she bent over and pulled her skirt up over her cheeks to rest on her lower back.

“Will you begin, Sir?”

Her ass was as good up close as it was across the court. The fine purple lace set off the white, mottled rounded cheeks to perfection. Once she was still, I laid the paddle along both cheeks again.

“Ooooooooooooohhhhhh, eleven, Sir. One more… please?”

Number twelve I moved to just the right cheek. I tried to land it at about forty five degrees so it hit another part of her cheek. And it did.

“Thirteen! Please another!”

Same but on the other side for the next.

“Fourteen! More, please, Sir!”

The next was on both cheeks. She more moaned than anything else.

“Fifteen! Please give me one more, Sir, but hard, really hard.”

As I saw what she could take, I wound up a bit more and landed a solid blow on both cheeks at the fleshiest part. She stood and grabbed her ass with her head down.

“Sixteen. Fuck fuck fuck that hurt but sixteen, Sir. May I have a normal one?”

With a crack, the paddle landed flat on her cheeks once again.

“Seventeen… hard… please, Sir.”

I cracked the paddle down once more with force. She didn’t say anything. I waited.

“Eight… teen. Eighteen, Sir. Another, please?”

It was a pretty average stroke.

“Nineteen. Just one more, please.”

The final stroke was average as well but the culminating effect appeared to leave her breathless. She composed herself and then stood to look at me, a new gleam in her eyes.

“Twenty, Sir. Twenty hard strikes. Ten on my skirt, ten on my flesh. Thank you, Jeff. Did you… like doing that?”

I nodded and smiled.

“Well, if we play a few time a week for this kind of wager, maybe we will enjoy it more?”

Her coy smiled tugged at me.

“I did enjoy the game.”

“Well then… shall we play another game? Same stakes?”

It was going to get even hotter in the kitchen.

I smiled and took my side.

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