Putting It To Good Use

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A lottery winner finds a satisfying way to use his winnings.
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techsan
techsan
1,198 Followers

Author's note: the following story is purely a work of fiction and any resemblance to real people or events is purely coincidental. The author wishes to express his gratitude to rozezwild for her editing to make this a better story.

I leaned back in my big desk chair as I read an article in the online Wall Street Journal. This situation might have an impact on one of my investments and could determine whether I sold my shares or bought more.

As I read, I kept moving the middle finger of my left hand. It was in a soft warm wet place that I loved to feel. And the more I felt, the more the aroma of the slowing flowing liquid reached out for my nostrils, a fragrance that was at the same time distracting and inspiring.

Reaching the end of the current screen's data, I hit the scroll bar and glanced to my left. Clara was sitting in a chair identical to mine but she had her legs resting on the heavily padded arms - one on each arm - her butt near the front edge of the chair. She was slumped down, head thrown back and lolling from side to side, eyes closed, her face reflecting the ecstasy of sexual satisfaction. She was also as naked as the day she was born.

My finger was buried in her wide-open pussy. There was a white froth around the blood-red lips, showing how long I had been diddling her and the orgasms she had already experienced. As I turned back to the screen, I extracted my finger and put it in my mouth, savoring the sweet taste of the oldest of my assistants, my lovers.

Clara had been with me for over four years. She was the first assistant that I hired after I came into the money. I had planned on creating a small harem of nubile young women, ones with curvy bodies and the willingness to use them frequently. When Clara answered my advertisement, she was already 39 years old and I almost said, 'No' on sight. How many times have I been glad that I didn't!

Clara has that curvy body. She has a 38DD-28-42 figure that really turns me on. She doesn't mind letting me fuck her any time of day or night or as often as I want to. She frequently encourages me to suck her tits. She needs just a few seconds to get ready for anal sex and she will suck my cock anytime anywhere. I love the way she responds when I finger her pussy, which is a favorite pastime when I'm not quite ready for something more serious.

I turned back to the screen and finished reading the article, deciding that there was not enough information there to justify a change in my stock position, one way or the other. However in the middle of that page, Clara's left hand slipped up the leg of my loose shorts. At first she clasped my balls, rolling them together like hand exercise balls. Then she moved to my hard cock, first gripping the shaft and slowly moving her hand up and down, then moving the palm over my purple arrow.

As I finished reading, I stood and pushed my chair backward. Clara pulled my shorts down and then bent over my desk. I patted her nice round bottom, spread her cheeks and let my cock find her slick opening. With one easy push, I buried my root right down to the base, loving the feeling of her soft buttocks molding to my crotch. I held us together for a couple of minutes, my eyes closed, just loving the feeling of being inside of her, occasionally flexing my long muscle in her twat.

I started pumping my tool in and out of Clara's slick opening, bumping her hard enough to mash our bodies together. Spotting her tits swaying from side to side under her inspired me to grab a handful of each and use them to pull us together again after every out-stroke, pinching her nipples every few strokes. Shortly Clara began moaning and thrusting her hips back at my every stroke, plunging me even deeper into her hot love box.

I managed to hold back for while, prolonging the feelings of ecstasy caused by the little friction between us but then my balls got that "lighter than air" feeling and began spewing my cum into Clara's hot pussy.

About the same time, she began shaking and hissing "I'm cccuuummmmiiinnng!" Whether she really experienced an orgasm or was just good at acting, I didn't really care at that point ... she was well paid to do what she was doing and if she got pleasure from it, that was a bonus, although it was a heady bonus to think that the women all climaxed when they acted like it.

I held us together until the last drops had oozed from my one-eyed Cyclops and then slowly leaned back when my flaccid cock loudly popped out of her cunt. Clara turned around, wrapped her arms around me tightly and gave me a tonsil-probing kiss that seemed to last forever, not that I minded.

When we broke apart, Clara smiled and said, "Thanks, baby!"

Then she padded down the hall to the stairway, still as naked as before.

I picked up my shorts, not bothering to put them on, and headed to the back of the house. Dropping my shorts on a table and tossing my shirt after it, I dove into the pool and spent the next half-hour swimming laps, although at a rather leisurely pace.

When I completed my laps, I got out of the cool water of the pool and walked the few steps to the whirlpool. The transition to 105 degree water was a little bit of a shock to my system so I was slow to settle in. By the time I had gotten my body used to the hot water and eased down until it was up to my neck, I was joined by Kim, at 29 my newest and youngest assistant. As usual, she was wearing no clothes and her beautiful even, no-lines tan attested to her love of the sun.

Kim had a similar build to all my other assistants. She was a little thick around the middle but her 42-inch hips gave her the big round bottom I liked and her 38DDD twins with the baseball-sized areolas and thumb-like nipples were well worth a little extra weight in the middle. She was shapely all around, altogether sexy in my opinion.

Kim waded through the water and straddled my legs, lowering her face to mine for several long sensual kisses. As I ran my fingers up and down her back and around her buttocks, my cock began to grow stiff again. Kim started to point it into her pussy but I had another idea.

Turning Kim around so that she faced the same way I did, I filled my hands with her huge tits. Kim knew what I wanted and she let her bottom gently float upward in the churning water. As she rose, her legs split to the sides while I held her head on my shoulder, still massaging her tits. I guided her a little to the left until one of the streams of water was pointing directly between her legs and she immediately reacted, shivering from the delicious impact to her most sensitive place.

It didn't take long before Kim was screaming "Oh, yes ... Yes ... YES, BABY!" and shortly that became "I'm gonna cum ... oh, yes, I'm gonna cum ... I'M CUMMMMIIIINNNNGGGG!"

I held her there until the waves of pleasure had floated off into the distance and she relaxed in my arms. Carefully I turned her around as she assumed an upright position. I pulled her to me and kissed her hard on her bright red lips as I lowered her onto my throbbing erection. When I leaned back against the tub, Kim took charge, clasping my cock with her strong inner muscles. Using short strokes, she began to milk my cock and in just a short while, my balls spewed their load of fresh hot cum high into her luscious body. I pulled her down by her hips and held us tightly together until my cock deflated and dropped out of her cunt.

As if on cue, Delilah, my cook, appeared and announced, "Lunch is served."

I signaled that we would be right in and while she turned with a smile to head back indoors, Kim and I climbed out of the tub, dried off and dressed.

When we walked into the kitchen area, all of my staff was already present. One thing I could not bring myself to do was to send the hired help to eat somewhere else while I ate in solitary confinement. All five of my personal assistants were in attendance plus Delilah; Janie, my chauffeur/part-time maid; and Sarah, the housekeeper. All of them had their own apartments in my house but they had been hired for their intelligence as well as their skills in other areas so I found it enlightening to take my meals with them all.

The five PAs were dressed similarly, per our agreement at the time of their hire. When they were in the house, they all wore cut-off t-shirts that did not quite cover the bottom of their tits and skirts that could come no lower than the bottom of their buttocks. No underwear was allowed. That way I got to see their assets frequently and had easy access if I wanted it.

Delilah, Janie and Sarah were all allowed to dress based on their jobs. None of them was included in the duties of taking care of my sexual needs ... although all three of them had had sex with me from time to time, for which they always received nice bonuses in their next paychecks.

We were well into our soup-and-sandwich lunch when I said, "Ladies, I've been thinking that its about time we take a vacation. I thought we could start week after next, take three weeks and do some traveling. I would like to visit some places in New England this time, with maybe some side trips coming or going to visit some of the historic sites. Anyone interested?"

There was an immediate clamoring around the table, with women jumping up and down. I asked for a show of hands and everyone wanted to go.

"Okay, okay, ladies," I said. "Janie, come to my office after lunch. I'd like you to call Jim Patterson to see about leasing a motor home for us. I've got some info on several and I'll let you know my preference. You'll probably need to make a trip over to their place to take a first hand look."

"Clara, if you'll come over, I'd like you to make some calls for hotel reservations. We'll spend most of our nights in the RV but I thought we'd like to spend our time in the larger cities in a nice hotel. I'd also like for you to make arrangements for us to go to some of the major attractions. Other than those, we'll just take our chances at the other places, okay?"

There was general agreement all around the table but already the talk had turned to what clothes to take so I added, "Ladies, I thought we would take a shopping trip tomorrow. Does everybody want to go?"

Suddenly there was a great clamor to go shopping. Every one of the women had suggestions about where to go but when I suggested Taylor and Marteen, a boutique that presents fashions by appointment only, they were all in agreement. I also suggested a trip to Victoria's Secret for some special garments just for the trip and they were again in agreement. I told them I would make the arrangements and requested that Jamie have the Caddy ready for us about 10:30 the following morning.

By then the meeting had disintegrated into a bunch of side conversations and I figured, having finished my lunch, it was time to move on. I got up and left the room, ambling downstairs to the game room. Although I had not asked her to, I was followed by 33-year-old Jennifer, another of my PA's.

As I got to the basement level and turned on the lights, I asked, "Jenny, would you like to play some pool?"

"Sure, honey, I always like to play with the balls."

I looked up to see her sporting a rather devilish smile. As soon as she saw me look, she flipped her skirt up, showing her neatly shaved pussy with its little heart-shaped patch of hair just above the crevice to her inner sanctum. I had a feeling we might not complete a full game.

I offered to let her start but Jenny said, "I don't ever like to break the balls. You go ahead."

So I racked up the balls and hit the cue, although I was a little distracted when her cue stick caught under her t-shirt and lifted it just enough to show her heavy left tit. The balls moved around the table but it was not a good break.

With my cock quickly growing stiff in my shorts, I didn't play well. If I stood behind Jenny while she shot, I couldn't get my eyes off her bare butt when she bent over. If I was to the side, I kept looking at her hanging hooters. From her front, her long black hair and beautiful face had me wanting her. She took every opportunity to rub her body against me or to feel of my crotch as she circled the table.

Of course I didn't keep my hands off her either. Whenever I got close, I'd get a handful of her ass for a few seconds, occasionally even slipping a finger or two into her wet pussy for a few gratuitous strokes. Several times I managed to grab a handful of bare titty and a few times grabbed both of them and rubbed my crotch against her ass.

With seven balls still on the table, I could stand it no longer. I dropped my shorts, bent Jenny over the table and slowly slipped my cock into her hot pussy while she encouraged me.

"Yes, baby, that feels so good. Do it, honey, fuck me, please."

As if I could do anything else. I began stroking in and out, my cock well-lubricated by her free-flowing juices. In and out I moved, loving the feeling of my shaft rubbing against the walls of her cunt, loving the feeling of banging into her soft round ass, loving the feeling of the malleable flesh of her tits as I squeezed them. Still, I felt a need to be able to kiss her, to tease her clit as I stroked, so I pulled out and turned her around.

With Jenny sitting back against the table, I lifted her legs around me and pointed my cock back into her sweet pussy, I leaned forward and she put her arms around my neck, meeting my open mouth with hers. For some reason, I wanted to insure that Jenny also got off so I rocked against her pubis at the end of every in-stroke. Shortly Jenny began to gulp air nearly every time I rubbed her clit.

With a toss of her head, she cried, "I'm cumming! NOW! YES!"

Watching her face was enough to toss me over the edge. My balls began spurting cum into her body. I leaned over and stuck my tongue in her mouth and sucked as the seconds passed much too fast.

When my strength returned, I lifted Jenny onto the pool table and climbed between her legs. While she panted for breath, I latched onto one of her nipples and sucked for dear life. After several minutes, I switched to the other nipple and sucked hard. I knew from experience that she loved it and soon she was rubbing my cock and humping her hips up, trying to entice me to enter her again.

Before long I was hard enough to penetrate her slick love box and I slow-fucked her for what seemed like a long time, getting my strength back and letting my cock grow harder and harder. It was a magnificent feeling and I never quit sucking on her tits.

Finally she wiggled her ass and pulled her legs higher, one hand behind each of her knees. She said, "Do it now, honey. Fuck my ass."

I pulled back just enough to let my cock exit her pussy as I leaned back to get a good view of her bottom. Pointing my cock at her anus, I watched as it slowly began to open. I noticed the light glistening from the puckered folds, indicating that she had already lubricated herself. I glanced at her and she nodded so I eased forward and pushed gently, watching the cover move aside and allow my cock to enter her, although not without some small resistance. Yet her face showed no pain, only encouragement as I went deeper into her bowels.

Although I really loved fucking pussy, the tightness of even the slackest anus makes anal sex even more alluring and Jenny was no different than other women in that regard. She had relaxed her strongest muscle enough to let me fully enter her without pain and yet that little ring was so tight around my cock that it felt better than anything I could think of or even dream about.

After I had worked my cock in until my root was pressed against her opening, I began slowly stroking in and out, pulling back until I felt the rim of my helmet against her opening, then pressing in until I again mashed us together hard, causing her buttocks to conform to the shape of my crotch.

But even the best intentioned plans will eventually go astray in such an environment and that happened to me ... again. The desire to spend my seed overcame my yearning to prolong the interim pleasure and my speed began to increase. To bring Jenny along with me, I put the flat of my right hand on her abdomen and worked my thumb into her crease to tease her clitty. My left hand played with her right tit, pinching the nipple and pulling it up until her boob was shaped like an upside down funnel.

Something worked because Jenny started cumming just seconds before my own dam burst and I sprayed her bowels with my jism.

Afterward I rolled off her and gingerly climbed off the table, leaning back against it on wobbly legs until the adrenaline burn had passed. While I was still recovering, Jenny got off the table and padded to the bathroom, coming back with several warm soapy washcloths which she used to carefully clean me up, after which she gave my flaccid member a sweet little kiss.

Taking my hand, Jenny led me to the cum-stained overstuffed couch that sat in one corner of the basement. We cuddled and kissed and fondled each other for a long time, neither of us feeling any pressure to do something urgently. After a bit, I turned sideways and Jenny sat between my legs. She leaned with her back to my chest and I held her, mostly cupping her big bulbous titties while I kissed on her neck and right ear. After a bit, she lifted up, captured my cock and eased herself down on it.

I closed my eyes and let my mind drift as Jenny rocked her bottom, using my cock as a fulcrum. Like every other willing pussy I had ever fucked, it felt great to be inside her. In addition, unlike with a few women I had been with, I liked the rest of her body too: the roundness of her hips, the shape of her waist, the more-than-handful all-natural boobs, the easy-to-look-at face, the long, well-kept hair, everything about her. And when I came, you would have thought I had just given her a very valuable present.

After a sweet kiss, Jenny headed upstairs to clean up and I grabbed my shorts and headed to the basement bathroom.

I played a couple of games before the next PA, Karen, came skipping down the stairs. She danced up to me laughing, moving to some unheard music in her head.

As Karen and I got together, I realized once again how fantastic it was to be fixed financially so that I could hire sweet young women like this to take care of all my wants and needs. I had the money. Might as well put it to good use!

The End

techsan
techsan
1,198 Followers
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3 Comments
oldtwitoldtwit3 months ago

Oh a boys dream,

AnonymousAnonymousalmost 18 years ago
waiting for sequel

well written, hot story. Please don't make us wait too long to continue the story on vacation.

AnonymousAnonymousalmost 18 years ago
Every male's wet dream

techsan:

Even this Horny 'ol Sailor. Hot and well written too. Hope you stay with it long enough to take us all on their trip. Thank You. Ronnie W.

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