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Winner, winner, basketball after dinner!

"Turns out I had more game than I thought"

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I was shooting hoops after dinner, as was my usual custom. My ex-wife took the kids and left the house to me, where I had spent perhaps too many hours shooting on that court, either staying fit or refining my daughter Madi's basketball skills.

"Madi home?" asked a familiar voice from the gate. That came from Eva, the senior transfer neighbor that led Madi's high school team to a state title. She often joined Madi and I in our backyard, and I would coach the two of them up.

"No, Madi's at her mom's tonight," I answered, deftly noticing how her sexy little shorts showed off her long slender legs.

Eva was an eighteen-year-old certified triple threat - looks, body and personality. She possessed big beautiful eyes and a seductive smile that could instantly melt anyone with her focused gaze. Her athletically built body was accentuated by a chiseled pear-shaped ass that developed through years of basketball training, and a pair of bouncy teardrop tits that demanded well-deserved attention. On top of all that, Eva had a playful demeanor, with the ability to subtly provoke mind-numbing thoughts. She was a master of double entendres, using them to flirt relentlessly. As a result of all this, she was the singlemost popular inspiration for numerous teen self-gratifications. And for certain divorced grown men too.

"Ohh, I have you to myself then. How about a little one-on-one, Dr. JJ?" asked Eva in her what-did-you-mean-by-that ambiguity.

"First to twenty-one then?" I responded, resisting letting her get inside my head.

"How about a friendly wager? If I win, you have to treat me to a victory smoothie," Eva proposed.

"And if I win?" I asked.

"Well, I highly doubt that'll happen, but I'm sure you can think of something you want," she intriguingly answered. Titillation noted.

Now although I was pushing forty-five, I still had some game left. Whatever advantages Eva had in skill and quickness, I made up for with size and determination. The game battled back and forth, and it came down to the final basket.

"OK, winner takes all. If you can make this free throw, you get whatever you want, if you miss, I get my smoothie. No pressure," pressed Eva.

I nodded, not knowing how this was going to play out. I desperately wanted to make this shot, however, I was more than twice her age and sex was out of the question, wasn't it? Many times before she had knowingly teased me in public, but it was probably just my horny imagination. Not to mention there'd be hell to pay if anyone found out. There was also the obstacle that if it did go in, how exactly was I going to tell her what hopefully I wasn't the only one thinking?

"...Whoo, OK Eva, that's game. Now get on your knees and suck the living daylights out of my cock before I fucking pound you..." It all just seemed unfathomable.

It was at that point, Eva removed her windbreaker to reveal a clingy white cropped tank, sans bra. Her sweat had made it quite sheer, to where I could see the outline of her pouty nipples on top of those ripe melons. She stuck her chest out and rolled her shoulders, making them heave even further. Eva had now stepped over the line, so to speak, openly distracting me with her tits. It was working too, as I had a hard time focusing on the task at hand. 

I tentatively stepped up to the free throw line, dribbled the ball three times, took a deep breath, and let it fly... CLUNK! Not even close to going in. Breasts 1, Me 0.

"I guess you win, I'll go get my keys," I said, to my disappointment. Eva trailed me though the sliding door into the kitchen.

"I've been thinking, I don't want a smoothie right now, I want something else... how about you give me a physical, Dr. JJ?" Eva said seductively.

Those words hung in the air for a pregnant pause. You see, I wasn't a medical doctor at all. I just had a doctorate's degree in Engineering. And since I go by 'JJ' with a proclivity for basketball, people started calling me 'Dr. JJ'. Surprisingly, Eva had anticipated this scenario - finding me alone, tempting me, propositioning me regardless of outcome. I didn't know why this was happening now, but I wasn't going to complain. Maybe it was on her bucket(!) list. My personal list was getting a rapid revision.

"Come stand in front of me," I directed.

"Okay, Doctor," she said, as she stepped up eagerly.

I felt her forehead with my hand, then put my hands on her head and kissed her forehead. "Hmm, you're kinda hot," I said, losing myself in those eyes.

"I think you are too," she retorted. 

"Let me see that tongue now, Miss," I requested. Eva impressively extended her tongue a good distance. Then she curled it up and licked the top of her lips. I put my lips up to hers and went searching for that tongue and wrestled with it.

"I've never had a doctor do this with me. Is this some kinda new procedure?" she inquired in an innocent voice.

"Why yes, I can tell a lot of things by taste, it helps me with my evaluation."

"Oh, okay, did you get a good taste of my throat, Doctor?"

"Ahem, why yes, I find it very promising. On to your breast examination."

Eva nodded. I raised her crop top over her head, and her breasts magnificently dropped back down. I supported them in my hands, and lifted, as if to weigh them. Then I ran my thumbs over her dark pink nipples and squeezed them, supposedly checking for lumps. Nodding with approval, I leaned down and tasted her nipple, sucking it deep in my mouth and running my tongue over the tip.

"Mmm, yes Doctor! I hope you're happy with them."

"Oh, definitely. I'd say they're as good a pair I've ever tasted. Okay, now I need you to remove your shorts and sit up on the counter for me."

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Eva pulled off her shorts to reveal her clean shaven pussy. She put her hands on the counter and lifted herself up. I looked into her eyes as I ran my finger along her pussy lips. She gasped when I probed her, reaching my finger deep inside her warm wet pussy. I worked my finger rhythmically and she bit her lip.

"Mmm fuck, you gonna taste me down there too, Doctor?" 

I leaned her back on her elbows and had her open her knees. I stuck out my tongue and licked right up the middle of that tight teen pussy. Then kissing and darting my tongue inside her.

"Hmm, I'm sensing something, but I'm not sure. I think I need to collect a larger sample from you." I intensified my procedure as Eva watched. She put her hand on my head and pulled me closer. My tongue caressed her clit as her hips gyrated on the counter. She moaned and released generously.

"Mmm, that was delicious," I said, as I wiped my face and licked my fingers. 

"Oh yes! Doctor, you're very good at that. But I hope you haven't finished, have you Doctor?"

"Oh no, we need to use my special instrument now. Kneel down, this is an oral device that I use to measure physical fitness."

Eva got on her knees and stuck out that elongated tongue as she slid down my bottoms. My excited cock popped out of my shorts and grazed her chin.

"Wow, Doctor, I hope I can measure up," she said eagerly.

Eva gently massaged my hanging balls. Without coaching she moved under to kiss them into her mouth, her tongue playing with it inside while looking up at me. Far better than I could have ever imagined.

"Mmm yes, Eva, very good ball handling skills. Let me see you stroke it."

She gripped my shaft and began stroking me to a raging hard-on. Her thumb tickled the tip of my opening, and she lubricated her hand with the ensuing fluid.

"Doctor, I think I'm up for the challenge, but do you think it's gonna fit in my mouth?"

"Yes, the more you put in, the better the results."

I watched as she made the head disappear in short order, and then she started to inch down the shaft. Eva, the overachiever, managed to swallow the entire thing.

"Mmmm yesss, I'm quite pleased so far. But I want to give you some special medication for a boost in your energy levels, and I'm going to need to use this same instrument to dispense it. Where would you like to take it, Miss?"

"I was hoping that might be the case. I've been thinking, although I've never tried it before, I'd really want to, you know, in the ass."

"Well yes, very good choice! I think you'll be satisfied with that. Just hang on a sec."

I grabbed some nearby olive oil and poured some into the palm of her hand. She grabbed my head and coated my cock by stroking it thoroughly. She took the excess and rubbed it into my balls, massaging them yet again.

She assumed the position on the counter top, holding onto the edge and dangling her feet outward. I poured some more extra virgin olive oil down her butt crack and used my thumb to work it in, gradually pushing my way into that tiny hole. After an initial shock from my intrusion, Eva relaxed and I started swirling my thumb around. She even started to wiggle on it.

Her ass was ready to be filled. I brought my cock up to her gaping sphincter and wedged in my oiled head as I simultaneously slipped out my thumb. She took deep exhales as I slowly continued to insert deeper. She waved an arm.

"Mmph, that's far enough, Doctor!" she exclaimed.

Then I slowly started fucking that tight ass as Eva squealed. I took the liberty of pushing my cock in deeper each time until she was accepting all of me. Her hands gripped tightly on the edge of the counter top. Her toned cheeks absorbed my thrusts, rippling each time. I slapped one hard and squeezed it. 

"That's for teasing me in public," I explained.

"I teased you more times than that," she gasped.

Then I spanked her ass repeatedly, until the redness stopped disappearing. I slid her back down so she could put her feet on the floor. I rocked harder into her ass now and reached around to play with her clit.

"Oh fuck Doctor, that feels amazingggg!"

"You ready for it?"

"Oh please Doctor, give it to me...I want you to...fuck my ass!"

I took a grip of her hips and pumped furiously, having fantasized of this moment. Watching my shaft slide in and out of her violated hole. Her anus was still so tight, I quickly reached the point of no return.

With my last deliberate fuck, I moaned, "Oh FUCK!" as I exploded inside her ass. Eva screamed out too. My body spasmed as I savored the rapture with every stream of cum departing the tip of my cock. Load after load into her. Eva's body went limp and she lay there panting.

"Mmm, Doctor, thank you so much. That was fun - I thought it felt like poop at first, but then I fucking loved it."

We were worn out and needed refreshment. We got dressed and I helped Eva into my car to get a smoothie. As we sat down in the place, guess who would happen to stroll in - Madi, with her mom.

"What are you guys doing here?" she asked.

"Eva and I had an intense game of one on one. She won, so I owed her a smoothie."

"I can't believe you lost, Dad!" said Madi.

"Well, you know, for some reason my concentration wasn't good, though I was shooting well. And even though I did beat Eva's ass a few times, she wanted it as much as I did, and everything came together for her in the end, right Eva?"

Eva just nodded awkwardly and sucked on her smoothie.

Published 
Written by midlifedaddy
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