Life At Islands Estates Ch. 18

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A little about Lisa.
5.7k words
4.7
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Part 18 of the 27 part series

Updated 09/22/2022
Created 11/30/2002
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The wedding at Islands Estates had been a tremendous success. Our houseguests eventually returned to wherever they had traveled from and things took on a semblance of normalcy, as much as one would expect around here.

Dennis returned to Nashville to play music with his friend Waylon. Marie went on the road, for the summer, with a group from Jacksonville. Karen took summer courses at Gainesville, hoping to hasten her education. Gerald and Susan, Dennis's mother who had recently divorced her husband, moved into the boathouse, which was a much bigger place than the other apartment.

Helen Blossom had completed her required classes at Stetson and by mid-summer had taken The Florida Bar Exam. When I asked how she felt that she did, she simply said, we have to find her an office. Sure enough, she was a full-blown 'Esquire'. Of coarse, that required a little congratulatory party. So, Rita and Camille and I went over to her house and we fucked each other senseless for hours.

Camille and I began working earnestly on the Palm Coast Development project. Planners and contractors were hired and work began on the marina portion. Roads were designed and a water main system was devised and civil contractors were solicited and retained as work started. It would be a tremendously expensive undertaking, but the long-term profits would prove to be enormous.

Rita had indeed become pregnant on our wedding night and our first child was due in early March. Almost the same day as Caroline had been born. With Camille and I spending so much time on the development, Rita took over duties as wife and mother and along with Louise ran the household. Caroline was in good hands.

My plans to extend the northern boundary of the estate, one mile, were being executed and Gerald was to begin construction of a new stone fence soon. The existing iron fence was in need of extensive repair so it was decided we would build a new stone fence, replacing the old iron fence, along with the new extension. This would require nearly four miles of eight-foot high stone walls to be erected. I instructed Gerald to hire as many masons and laborers as necessary to complete the project. We bought a rock-hauler trailer for the big Peter-Bilt tractor and hired a driver to transport the stone from the port in Fernandina. It took 240 loads of stone for the fence and took the masons a year and a half to construct.

We had purchased a bulldozer and a track-hoe for the site-preparation necessary.

We cleared some thirty acres for the construction of a horse ring, pasture and stable. Dad was proud of me; I was spending his money with reckless abandon and having a ball.

I hadn't been playing music much, but now and then, one of the groups in Jacksonville or Daytona would be a man down and give me a call. The Beatles and Rolling Stones and a whole bevy of bands from Europe were taking the country be storm, and the music was changing. I kept learning new stuff all the time.

One afternoon while Caroline and I were out for our daily walk around the yard, Louise came rushing out of the house to tell me that Dan Holiday had been involved in a serious wreck in St. Augustine and Lisa wanted me to come and sit with her at the hospital while he was in surgery. I handed Caroline over to Louise and made a dash up to the car park and throttled the old Ford Crown Victoria up and laid rubber for Flagler Hospital.

As I rounded the corner into the emergency room, I looked up and saw the doctor speaking to Lisa. Before I could reach them, I watched as Lisa collapsed into the doctor's arms. My friend's father had succumbed to his injuries. I helped the doctor to ease Lisa into a chair and he called for someone to bring some smelling salts to revive her. After she came around, the wailing started and I called for Louise to come and help me to bring her back to the estate.

We helped with the arrangements and after the funeral; Lisa came to spend a few days at our place while the reality of her situation settled in on her. Camille and Rita both spent a lot of time with her and after a couple of weeks; Lisa asked if I would drive her up to her house in St. Augustine. She still didn't want to go there alone.

We left the estate around 8:30 in the morning and I drove up the coast to The Ancient City. Lisa and her dad lived in a house on the bay on Anastasia Island. The house was large, stately, and in terrible repair. It seems that Dan had let the old place run down. Lisa told me she wanted to stay here, but it would cost a fortune to fix the place up. Then she told me her dad had pissed most of the money he had away on junkets to Las Vegas and Atlantic City. She plopped down on the sofa and flung her face into her hands and started to wail again.

I sat next to her and put my arm around her shoulder. The howling lasted for a half hour or more. Her mascara made long dark trails down her face.

"What am I going to do, Cool?" Lisa sobbed.

"We'll figure it out. Don't worry," I soothed.

"That's easy for you to say, Mr. Rich Kid," she railed on. "I have exactly nine hundred and sixty bucks in the bank, and a jet airplane, that has a twenty four hundred dollar payment due on it next Friday. How would you feel?"

"How much is against the jet?" I asked.

"About eight hundred grand," she said, dejectedly.

"I'll buy it from you," I said. "I always wanted an airplane."

"Then what do I do to make a living?" she asked.

"Fly the plane for me. I'll pay you what ever you say," I said. "How about a thousand a week to start? Plus I'll give you whatever the plane is appraised for."

Brightening up a bit she said, "Looks like you got yourself a deal, Rich Kid."

"What's this Rich Kid shit all about, TRAILOR TRASH?" I asked.

"Only kidding," she whined.

"All right, show me your house. I want to see what has to be done to make this place livable," I said, standing up.

The old house was great, although in need of serious attention. As we walked through the high ceilinged rooms of the house where Lisa had grown up, she told me little stories about things that had happened over the years. I listened attentively as she rambled on about her mother and her dad. She was missing them desperately. We climbed the stairs to the second floor and up to the widow's watch on the roof. We looked out to sea and the wind whipped through our hair as we leaned against the rail, which was about to fall off.

Returning to the second floor, she showed me her father's study, piled high with books and old papers. The last room at the end of the hall was the master bedroom. It was bright and airy, the only room in the house that didn't require major assistance. It appeared to be the only bedroom in the house that had been in use recently.

Standing in the doorway, I could see into the closet next to the door and I could see both men's and women's clothing hanging in it. It suddenly dawned on me that Lisa and her dad had been sharing the room and I assumed the bed.

"I didn't know about you and Danny," I said softly.

"Nobody knew," she whispered. "He's the only man that ever really loved me. I'm gonna miss him."

She sat heavily on the edge of the bed. As she sat, a long silver vibrator rolled from under the pillow and bumped against her hip. We both looked at it at the same moment.

"Guess I'm gonna be needing this a whole lot more," she said.

I reached for the cylindrical sex toy and switched the vibrator on. I glanced at Lisa as the buzzing started. Her braless nipples hardened at the sound. I extended the toy and touched the protrusion in the front of her blouse with the tip. She looked up at me and sucked her breath in as I made contact with her nipple.

"You're gonna get me all hot and bothered with that thing," she breathed.

"Yeah? And them what?" I asked.

"And then you'll have to fuck me," she whispered.

I applied more pressure to her tit and then moved the vibrator over to her other nipple. Her breathing was getting ragged. It had been over two weeks since she'd had sex and Lisa was primed and ready. She fumbled with the buttons on the front of her blouse and opened it exposing her sizable boobs. I helped her pull her arms from the sleeves. I kept the vibrator in contact with her one of nipples and reached to pull her short skirt up over her hips. Lisa's red thong panties were pulled tightly into her puffy pussy lips, which hung invitingly on either side of the thin red ribbon of satin, and had grown wet with her stimulation.

Her areola had grown large and dark around her highly aroused nipples. I continued to torture her with the vibrator, sending sexual shock waves to her brain from the incessant vibration. Her brain in turn sent signals through her entire body, causing it to tremble and convulse.

With my free hand, I tugged gently on her soggy panties pulling them higher up into her slit. The wet lace fabric rubbed harshly over her exposed clitoris building a blazing fire of desire deep inside of her. Her words became unintelligible; she gasped for breath and collapsed back on the bed as her orgasm consumed her.

Lisa lay there shaking. I threaded her wet panties down her tightly clasped thighs and pulled them over her shoes. They made a wet lump in my pocket as I stuffed them away to be added to my growing collection. I'm a panty pervert. I admit it!

Lisa was a bottle blond, because her pubic hair was dark brown. The last time I was with her she had been clean-shaven, but now she had a furry brown pelt between her legs. I focused on the spot where her thighs came together, pushing her knees apart. I knelt on the floor between them and zeroed in on the little pink nub just barely visible through the folds of her blood engorged nether lips. Without making any other contact, I touched her clit with the tip of the silver vibrator.

Just the merest contact sent her surging into another climactic convulsion. Her scream was shrill and started high and decreased in frequency like a siren. Lisa bucked up in the middle, grabbed my head and pulled me into her breasts. Her legs shut around me and clamped me tight against her. I was trapped against her thrashing body until her orgasm passed.

"If you don't get naked and fuck me right now, Virgil Ellis, I will kill you," Lisa cried, throwing me back away from her and pushing herself up on her elbows.

I quickly stripped out of my khaki's and shirt. Mr. Johnson was armed and ready. A long thick thread of pre-cum oozed from my slit and hung down. Lisa threw her legs wide apart, pushed herself back on the bed, making her cunt lips spread open. I advanced up on the bed and crawled into her center. I pushed deep in her hot pussy without any further hesitation, humping frantically into the writhing girl. Her knees were up and her feet flat on the bed. She met every thrust with a lunge of her own, jarring us as we came together. I was close to cumming but I waited for Lisa. I didn't have to wait long, though. She erupted into a series of gut wrenching spasms, which inspired me to toss her hot box full of scalding glop. I must have really glopped her too, because it was oozing out of her all over the place. We were slippery with jizz.

"Damn, Girl. You okay?" I gasped, rolling off to the side.

"I am now," she hissed.

We lay there regaining our senses. Too bad man was invented with only enough blood to fill one head at a time. I was still having hard time thinking.

"How long had you and your dad been doing it?" I asked.

Lisa was silent.

"Never mind, I shouldn't have pried," I said, feeling lame for asking the question.

"Oh, no, Cool. I don't mind you asking. I was just trying to think back on when it started," she said softly.

I fluffed up a pillow and stuffed it under my head. Lisa scrunched around on the bed and lay with her head on my shoulder. We were both still covered in thick milky cum.

"Mama died when I was nine," she began. "Daddy was heartbroken without her. We would sit on the sofa for hours talking about how much we missed her. We would cuddle and he would tell me stories. The years went by and we finally quit carrying on about mama and started to talk about other stuff. Sometimes when we were sitting real close, his pecker would get real hard in his pants but he never came on to me, or anything like that. Sometimes, I'd see him coming out of the shower and catch a glimpse of his big cock swinging as he rushed back to his bedroom. I used to sleep with him and sometimes in the night, he would get hard in his sleep and I would feel him against me. I wanted to know more about sex and stuff when I got older, but he wouldn't talk about it much. I started taking flying lessons when I was sixteen and soloed when I was seventeen. That's when he bought the little Cessna, for my eighteenth birthday."

Lisa wriggled a little to get more comfortable. Unconsciously, her fingers dabbled in the stickiness on her belly and she rubbed it into her sensitive nipples.

She continued with her story. "We were flying all over the place. It seems like we were always together after I graduated. I really never dated anybody except for one guy I met in one of the flight schools. But I never fucked anybody until after daddy popped my cherry one morning. I was in my room getting ready to go flying when he barged into my room to hurry me up. I was standing by the dresser, combing my hair, which was a lot longer and brown then, with just my panties on. He stopped dead in his tracks right inside the door and his dick poked a tent out in his pants. I had been horny for years and even hornier for him, so when I saw his hard cock, I put down my brush and walked over to where he was standing, pulled is erection out of his pants and sucked his load down. He never lost his hard on after he came. He picked me up, put me on the bed and pulled his pants off. He had a rubber in his pocket so he must have been planning it for a while. His hands were shaking so bad that he couldn't get the package open. I took it from him and tore into it with my teeth and rolled it on his big pecker. He turned me over on my hands and knees and stuck his cock right in me."

Her hands were busy rubbing through her fuzzy bush as she related her deflowering. "I had been using dildos and vibrators for years so he went right in. My God, how much different it felt. I could get myself off, with the toys, but when he shot his hot load into that rubber inside of me, I fell apart. I went on and on 'til I thought I was going to die. I went on the pill, right away so I wouldn't get knocked up, and we could quit using rubbers. The first time I felt his hot cum shoot out in my pussy, it was awesome. We did it everywhere after that, even in the airplane. I've had a few other guys, including you, but I'll never forget how daddy fucked me. He said it was just like him and mama when they were first married."

Lisa rolled up on her elbow, placing her hand under her head to hold it up, and looked at me. Her nipples were hard again. She had been rubbing her pussy while she talked. My dick had grown about half hard listening to her story, and a thick drop of juice oozed from the tip. Her fingers traced a line around my nipple and she leaned in and took it in her lips. She gently tongued it and nibbled at it with her teeth.

"Sounds like you were really tight with him," I said.

"We were everything to each other. He always pushed me to date but I couldn't get interested in anything meaningful when my mind was always on him," she said.

"Did he date anybody else?" I asked.

"Sure," she answered. "I always wanted him to find someone he could be with. Although, I knew in my heart it would end what we had."

"Did you ever do anything kinky with him?" I asked. I was getting nosey, but I figured she'd tell me when it got too private.

"Hell yes!" she exclaimed. "He fucked me on the Bridge Of Lions in the middle of the night once. He liked trashy clothes too. You probably noticed that."

"Yeah, I did. I thought that was your idea. Was he behind that?" I asked.

"Yup. That's how my mother dressed when they first met and I guess I was just retro for him," she said.

Her hand had wandered down my belly and she was gently rolling my cock head in her fingers. I was oozing a steady stream by now.

"So when did you learn about women?" I asked.

She smirked, and said, "Your big sister is behind that. She and your dad came over one time, not long after daddy and I started fucking. Daddy had told me about their relationship and how he would fly up to New York and spend a few days with her, humping her brains out. Anyway, one night they came over and Dianne and I were sitting up on the roof smoking. She told me how horny she had been and that she sure was glad to be seeing her daddy. I wasn't thinking but I said I understood what she meant, that I didn't know what I'd do if daddy went away. She looked at me all funny and then she just asked out loud if I had been doing him. I didn't have any other answer except yes. Then she started telling me all about her mother and Louise and all the strange things they did out there in that big old house. I was absolutely dripping from all of her stories. I guess I must have started playing with my pussy, I always do that when I feel horny, because the next thing you know, she was on her hands and knees eating me out. Daddy had never done it like Dianne did to me that night. You eat pussy as good as she does. But it's different with a woman."

"So I'm told," I said.

Lisa was earnestly stroking my steel hard cock now. Her story had taken its toll on my resistance and I was ready to fuck again. Her mouth engulfed me and she slurped me for several minutes before she straddled me and started to ride me from the top.

She rocked gently. Not really pulling off, just rocking. I watched her face. Her eyes were closed, enjoying the feeling of being stuffed.

"I remember the first time I saw you out at you place," she said softly, keeping her slow rolling motion going. "I was absolutely creaming in my panties by the time I got home. I used up a set of batteries in my vibrator that night."

I recalled the night she was referring to. My dad and hers had sailed our big boat for South Florida. As I remember, Chrissie and Gail were waiting up in the studio for me.

"Why didn't you say something?" I asked.

"Because you had two girls already lined up. And I was so much older than you, I didn't think you'd be interested." Lisa made a good point. "But when you sucked on my boob in the airplane, I knew we'd get around to it soon enough."

"Well I guess you were right. Tell me about your visit in New York when you flew Dianne home from my graduation." I said.

"Oh, God! Dianne is really into some weird shit. She gave me some of the kinkiest clothes. See-through dresses and blouses and skirts that didn't have any buns in them and I don't know what all else. She even gave me a couple of corsets that lace up the back and a pair of panties that has a dildo thingy inside that you slip into your pussy and wear all day. I love it but I get so gooey that it makes a wet spot on my jeans or skirt when I wear it." Her breath was getting raspy with all the sexy talk.

"Lord, yes." she cried. "Rita's brothers took me from both ends the first night. That was the first time I had ever been fucked in the ass. Now I can't get enough. And that friend of hers, Casey, what an absolute slut she is. She has the filthiest mouth I have ever heard on a woman. And she has to piss all over you when she cums. How disgusting can you get?"

I chuckled to myself, because I was very familiar with Casey's bathroom habits. I have some of my own but Lisa hadn't been around me that much. I reached for her tits and kneaded them as she continued to rock on my perpetual hard-on.

"So, Cool, how goes it with your little harem out there in the dunes?" Lisa asked.

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