Picle Ball

Pickle Ball-7

Ray and Tracy go to work. If you like this story, please give me a vote and a comment! Enjoy.

The next few days, I stayed busy. I finished two jobs, I played my guitars, I painted a few canvases, I fixed an appliance. I never thought about my penis and he never thought about me. and that was just fine.

I got a call from Jess in Miami. First, I told her of Jay and Janice. Jess commiserated and then got right to the point.

"So, how are you, Ray. I feel like I was just getting to know you. But, I think you and Jeff connected."

"Yeah, I think we did, too. How's it going there? I miss you both."

"We'll be back tomorrow. And we're bringing my assistant, Tracy." I perked up. "Tracy has been doing all the prep work here and now it's time for me to do my thing. Tracy is going to prep some properties on Bird Key and one on Casey Key for me. So, the plan is that after a few days, Jeff and I fly back to Miami and Tracy stays in the apartment in Sarasota."

"That's a lot!"

"Nah, we do this all the time. In fact, Jeff is flying up to the Hamptons next week to look at a few tips we got. While we are flying around, I'm sure that you will tend to Tracy's needs."

"I promise to do my best. And tell Jeff to ask me about the properties. I used to live in East Hampton."

"Really?"

"Yup, forty years. Had a lot of good times up there."

She laughed. "I'm sure. Listen, keep dinner open tomorrow. Be at our apartment at six, okay? I promise it will be worth it."

I was hard when she hung up. New possibilities! Wow.

The next evening, I drove over to the Ritz-Carlton Residences and Jack Dusty, the waterfront restaurant that I was directed to go. This hotel, a high-rise luxury property, with spectacular views of Sarasota Bay and The Gulf of Mexico, was about the best place in the town. Jeff, Jess and Tracy were sitting on the deck and drinking when I approached.

"Are you my tour guide?" asked Tracy.

"If you will let me guide you? Hello, I'm Ray."

Jeff ordered a huge bowl of shrimp with assorted sauces, a basket of fries and a large salad. I ordered a glass of Sauvignon Blanc but Jeff stopped me and ordered a bottle of their best chardonnay. I checked out Tracy as she was checking me out. This was one fine looking woman. I figured her to be in her mid-thirties, Tallish, about 5'9", with long black hair framing a beautiful face, she made a striking figure. It didn't hurt that her blouse was open revealing a cleavage worth exploiting. I figured she had a pair of thirty-eights, D-cups. I don't know that she noticed my crotch which was showing signs of stirring.

"This is the first time I've been here," I said, "To call it ritzy seems redundant. And this is a nice restaurant. Do you come here often?"

"Now and then," said Jess. It's convenient since we live here. Up there." She pointed to the building above us.

"Well, this certainly is a nice place to hang out. It feels so comfortable."

"Thank you, " said Jess, "considering I designed it."

Impressive, I thought. I turned to Tracy. "And how do you fit in this?"

"Well, it sort of goes like this. Jeff uses his incredible second sense and buys a property. Jess comes in and designs the interiors. I set up all the permits and prepare the infrastructure so Jess can do her thing. And then we sell it or, in some cases, own the property and license it out."

"How long have you been with them?"

"Going on nine years now." She turned to Jeff and Jess. "Wow, can you believe it? Nine whole years!"

"Tracy is my most valuable asset," said Jess. "She makes my job easy."

"And, what will you be doing down here?"

"My job in Miami is done. Jeff found some properties here that I will investigate for their potential to add to our boutique hotel properties."

Jeff added, "We have to get right back to Miami. We're leaving in two days. We thought you could be the perfect guide. I'm leaving a car in the garage for you. Use the credit cards in the glove department for gas and ancillary needs. I'm sure that you two will make a perfect couple, a legitimate cover for your snooping around. So far, this is all hush-hush and, for now, we'd like to keep it that way."

"It all sounds very interesting. Except for a couple of jobs I can complete tomorrow, I am all yours."

"What sort of jobs?" asked Tracy.

"One is a computer coding for a government agency and the other is a canvas I owe my gallery. Both are finished. I just need to put finishing touches on them."

We spent the evening talking about our histories. Jess and Tracy were mesmerized by my tales of being accompanying guitarist on the road with Davy Harper for twenty-five years. Jess, considerably older than Tracy, was a devoted fan. We talked a little about East Hampton which made me very nostalgic. But Jeff could see that I knew the place well and still had friends there.

The night ended with them calling it a night. Jeff said that they were leaving back to Miami on the day after tomorrow. Tracy said she would call me. I thanked them and headed home, considering the possibilities handed to me. I felt elated.

The next day, I finished my painting by dawdling over it until I signed my name to it. I drove it over to my agent, who also owned the gallery and he was very thrilled with the soft abstract of a nude. Then, I patched up my program and ftp uploaded it to CISA. I received a call about an hour later asking me some questions about the program. They would test it before signing off on it but I was very confident. And, suddenly I was free to concentrate on Jeff and Jess's plan. And, ahem, Tracy. Then, I plugged in and played me some guitar.

The next day, Tracy called me at ten, asking me to take her for coffee and to help her plan her itinerary. I got over there in about a half hour and took her to a French pastry place on Main Street. Over our coffee, I looked at the locations of her properties and all three were not far away. We walked back to the Ritz garage to get Jeff's car. It was the two-year old Bentley Continental GTC in metallic navy blue that we had driven over to the massage salon. I was in love. I suggested that I take her on a drive to see the properties, we'd catch lunch on our circuit and then I would show her around the environs. I just wanted to drive this beauty in this beauty. I put the top down so her black hair could blow in the wind. I was in heaven. It reminded me of the time I drove a Ferrari Testarossa around Maui. Now, that was a car.

"I've never been here to this part of the coast. I've been to conventions in Tampa and St. Pete, and one in Naples but never here. There's some real money down here, isn't there." Yeah, and I was driving it.

There were three properties on Bird Key and it took us about five minutes to pull up to the first address. In fact, it took us all of ten more minutes to see the other two. Her analysis was that none were possible for a boutique hotel. Neither of us liked any of the properties, even as private homes. It reminded us of Naples, much too congested.

Then we hauled down to Casey Key. This property was on the southern tip of the key across from Nokomis. This property was a different story. It was a small beach resort of twenty rooms, three villas and a row of cabanas. It had four tennis courts and a large pool. Unfortunately, it was run down. The owners suffered through a couple of Covid years and could not recover.

We spent about two hours as Tracy wrote notes and took a lot of pictures of the resort and the views. Back in the Bentley, I drove up to the northern end of the key until I got to the Casey Key Fish House. Tracy was quiet, writing and studying her notes and pictures.

"Oh, good. I'm glad we're here and breaking for lunch. I have a lot in my head."

"Just leave your notes and relax for a little while. You'll have a better perspective after lunch."

She had a grouper sandwich and I had a couple of crab cakes. We washed lunch down with a couple of local beers. When the check arrived, she reached for it but I stopped her and picked it up.

"You know, we can do this on the corporate credit card."

"Oh, I know. But I'd rather use my corporation, thank you."

"Thank you for lunch but I will pick up dinner. We have more to do."

As we drove back to the Ritz, we talked about the property. We both liked it as it had tremendous possibilities. Tracy envisioned razing the current facility, rebuilding and repurposing, especially the villas. I could see it as a pricey get-away complete with concierge and a gourmet restaurant bar. She saw the villas as having private pools. We tossed around ideas as she wrote more notes. We pulled into the garage and she asked me up.

I'd never been to Jeff and Jess's apartment and I really didn't know what to expect. As we took the elevator up to one of highest floors, Tracy said, "You're going to love this place." The elevator stopped and opened on three apartments. Tracy opened the one on the left and inside it revealed an immense living room with floor-to-ceiling glass facing the south and the west. The view over City Key, and Bird Key to Siesta Key was spectacular. A deep balcony surrounded the apartment with double chaise lounges and umbrellas. The interior design was very modern, studded with art and unlimited views. It was truly breathtaking.

"I have some work to do so I'll be a little while. You relax and I'll join you in a few minutes. Oh, and the kitchen is behind the wall over there. You good?"

"I'm great."

She left me to walk around the apartment. She was in the office/exercise room. I checked out the two bedrooms. The master had a super king-sized bed and several couches around it. Yeah, this was Jeff and Jess's room, fit for a luxurious intimate orgy. The ensuite master bath had a hot tub for about six naked apes and a walk-in shower for about two more. Geez.

I walked out onto the balcony as it wrapped around the perimeter of the apartment. The view in this direction was also phenomenal. I walked back into the apartment and chose not to peruse the other bedrooms. I got myself an iced tea and an ashtray and walked out of the living room to the balcony. I sat down on one of the double lounge chairs, sipped my drink and lit my joint. As I toked up, I stared out at the endless Gulf, listening to the sound of the waves lapping at the shore below. It was the epitome of relaxation. I put the joint down and closed my eyes.

I was awakened by Tracy laying down on the other side of the chaise. She leaned over me to get the joint. My eyes closed, she felt different. I felt her large breasts slide over my chest and opened my eyes. She was now dressed in a long tee shirt and, from what I could tell, no bra.

"Now, that's some way to wake up from a nap!" I said, smiling. "That was breastacular. Want to do that again...about a hundred times?"

"I thought I could wake you with a smile and I was right! It sure is peaceful out here. The breeze is so nice. I thought we could talk a bit."

"Sure," I sipped my tea and sat up. "What about?"

"Well, to begin with, I hardly know anything about you. I know that Jeff, Jess and you have had several threesomes and had sex with another couple. I know that you and Jeff had a killer pickleball game. Jeff said it was the best game he ever played. And I heard all about the massage spa you went to afterwards. Except for my friends saying that you were a great guy and a great lover, I don't know anything else. So, who are you?"

"I'm a computer scientist, I'm a musician, I'm an artist and yes, I'm bisexual." I proceeded to give her a Cliff's Notes version of my life, from my marriage to my years with Davy Harper, to my RV travels up to my present existence. "And pickleball was a curiosity I had so I joined a league to learn. Turns out, it's not a hard game and I met some very interesting people...and some not so interesting. And that's my story. Okay, now you."

She toked up commenting, "This is good stuff. Did you get this at the dispensary?"

"No. I got this from my connection. I like more powerful pot than the Florida dispensaries can sell."

She nodded in agreement. "I've got some good stuff from my Miami connection. I also have some stuff that Jess left me." She toked up again. "What can I say? I've been very lucky. I got married right out of college but it lasted only three years. He was cheating on me..."

"The fool."

"...Yes, he was. But I hooked up with Jess soon after. I was in East Hampton..."

"I lived there for forty years. That's my stomping ground."

"I love that town. Anyway, I met Jess at the Stephen Talkhouse..."

"I played there many, many times. It was my second home."

"..Anyway, we hit it off. She befriended me and soon after, offered me the job to her assistant. I've been with her ever since. She is the best boss and we are best friends. I'd say that I'm lucky...and blessed. Let me ask you a question, are you a good kisser?"

I leaned into her and wrapped my arms around her. I began to nuzzle her and kissed her on the lips. The first kiss was respectable. The second kiss was a bit more aggressive. Soon, we were swapping tongues and spit. Our kissing lasted a while until she pulled back. Her mouth and lips were made for kissing and I really liked it. I wanted more but she pulled back.

"I'd say that was gourmet kissing. You are a great kisser."

"Are you kidding me? You ain't so bad yourself. I'd have to say that you, too, are a great kisser. Tell me about your first time bi?"

I told her the story of getting picked up at the Blue Parrot by Roger and Patty and my subsequent encounters. And how Roger and Patty introduced me to a whole new lifestyle with others. "Oooh," she squealed, "that was so hot."

"Did I turn you on?" I pulled her close and started to feel around her t-shirt. "Tsk, tsk, tsk. Hmm, no panties?"

She rubbed a palm along my crotch. "Mmmm...nope. Jess said you might eat pussy better than her. You'll have to prove that to me, too."

I pulled off my polo and dropped my shorts. It happened that on that day, I chose to wear stretchy boxers instead of going commando. Honest, I don't know why. But, it had the benefit of pushing my erection against the stretchy fabric to greater a impression, displaying my seven inches and healthy nutsack to great effect. Tracy slipped out of her long tee. Talk about impressive! This girl had it all including a freshly shaven woofer. What about her breasts you may ask? Fuggeddaboudit!

It was early evening and the sun was setting slowly over the Gulf. I was hot and humid. We were on a totally private balcony. She was naked and spread on the lounge. I was mesmerized. I stood at her feet in my underwear. "Listen, I'm going to eat your pussy like it's a ten-course meal but first, you have to do me a favor. You have to kiss me some more because those kisses were extraordinary."

"Well, since you put it like that, I will be happy to oblige." She put out her arms. I crawled between her legs and slowly met her embrace. I put my arms around her and we started to kiss again, slowly getting up to speed. She curled one of her legs around one of mine and pressed my hard number into her slit. We were now kissing with abandon. Our hands were touching and squeezing and caressing each other. I played my fingers around her nipples and beneath her breasts. She ran her hand down my treasure trail until she gently ran it along my penis. She slipped her hand under my shorts and rubbed the head along her slit and around her clit.

I moved down and kissed her breasts. I sucked her nipples and tweaked them, I sucked them deeply and a little roughly which she liked. I could tell by her moans. I sensed it was time to move further down so I trailed my tongue to her pierced navel. She let out a little squeal. I moved down to her totally shaved vulva. Now, it was my turn to moan as I smelled her heated skin, perspiration and excretions. I licked around her outer lips and traced its magnificent design. I moved down onto her taint and pressed the tip of my tongue into her anus. She moaned as I circled the hole and stabbed at it. I made my way back to the taint and rolled my tongue into her warm, velvet-walled canal. She was wet and she was flowing as I drank her sweet nectar. She tasted like the honeypot she was. As my tongue made its way up, I circled her inner lips in the shape of an oval, arcing at the top of her clit. She moaned again and became more vocal, "Yes, yes!"

You know how advice is given that when eating pussy, one should trace the alphabet over the clit with the tongue tip? I'll tell my secret and this is very, very confidential. I don't trace the alphabet with my tongue, I go to a different alphabet entirely, like Cyrillic, Arabic or Hebrew. When I make an accent or a circumflex, it drives them wild.

My oral ministrations were driving Tracy wild as she trembled and had her first small orgasm. I sensed that she was still climbing. I went back down like a man possessed. I so enjoyed giving her head, she tasted so good. "Yes, right there, don't stop..."et cetera. She arched and had three peaks. I could swear I heard applause from another balcony.

She got up quickly and dragged me inside to her bedroom. It was time to bring out the big guns. So to speak. She was still very aroused when I peeled off my sweaty underwear. I settled into her yawning slit. Rubbing against her clit, she said, "Put it in me, damn it! Make me come again." I slid right in. I stopped, pulled back and then bottomed her to the root. We both moaned. She wrapped her pussy around me with a couple of kegels, milking me as I pounded her. I put my hands around her ass and lifted her up. Standing next to the bed, with her legs wrapped around my hips, I began to fuck her or she began to fuck me, I don't know which. "Oh, I like this", she squealed, as we leapt around the room.

She pushed me back on the bed and cowgirl-style, she rode the bronco. "Oh, Ray. This is great. You fit me just right. You're hitting my spot. Do me." Between her sliding, squeezing and groaning, I could hold it no longer and I started to spew my salty spew up her snatch. That set her off in an orgasmic howl as she bucked against my gut. She arched, squeezed and held her breath. Her orgasm flooded my crotch. We let the orgasm flow over us and then we collapsed, me still inside her and holding each other.

"That was great, Ray. That was real fucking. So good. I haven't cum through penetration in years. That felt so good. But now, I'm afraid to get up, I'll drip all over the place."

"Not if I clean you up first. Just get up here and get comfortable on my face." She got up and squatted on my jaw. My tongue slipped into her as I began to feel the drip of our combined sauce. I caught some large globs down my throat until the flow began to dissipate. Then, I lapped at her asshole, completely cleaning her. She got off me and laid back down. She kissed me, tasted and cleaned my mouth. It was dusk and the sunset was superlative. I felt very mellow and warm in her arms.

"I like that. You leave nothing to chance." She got up and pulled me, leading me to the shower. There we played with each other, giggled some and luxuriated in our nakedness. When we got out and dried each other, she suggested that we order dinner to be delivered.

We sat on the balcony eating so-so Chinese food and talked. "I haven't sent my report to Jess yet. I have mixed feelings about the Casey Key property."

"Yes, I do, too. Now that we let it sit for a while, I think it's too far away from civilization. This area is not like the Maldives, it's not isolated. And it's not a destination. But, I had a thought. What about a location over there on Longboat Key." I pointed to a bridge from Siesta Key to Longboat. "It's right over there. It's about ten minutes from the airport. There's also the Cortez bridge so it's easy to get to. I know that the Ritz-Carlton is rebuilding a beach club over there. Maybe you want to build a very high-end, deluxe private spa there...make it a destination vacation. We could take a look tomorrow."