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Lenny's Roots Chapter 6

"Jackie and Jill both looked identical when they were naked, only one's pointed tongue was a clue."

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My initial reaction to the newly assigned duties was a sense of disappointment. 

I had imagined being supervisor to a bevy of beautiful broads all begging me to service them after the curtain went down. 

Actually, it was a stroke of good luck that I was selected to be in charge of all the maritime activities sponsored by the casino. It helped me to focus more on the job and less on the available pussy surrounding me with temptation in every direction. 

The casino yacht club’s modus operandi was to man each of their speedboats with a good looking young heartbreaker with a friendly attitude to every customer no matter how annoying or boring they might be during their assigned time on the water.  

The young girls were selected on the basis of their lack of interest in true romance. The pretty young things had no confidence in the belief that love ultimately wins out over lust.  In all honesty, I was also a firm believer in the staying power of pure self-centered lust.

Lust was pure and focused unlike the search for love that assumed too much for the real world.  

These friendly females that monitored the excursions and piloted the boats mostly moonlighted in the casino at night as hostesses.  Some of them labored in the basement offices as money counters or support personnel for the active showgirls. They were the ones that lacked the right look to ring the chimes of paying customers. Most of them had lives of their own outside the casino. It was those outside demands that generally resulted in a need to replace them because they were required to be available at a moment’s notice.

Ramon had traded in his drug-snorting bitches for a pair of the boat-girls.

They clung to him like a refrigerator magnet. Destiny and Heather were willing to share, but warned off all other females to stay away from their private property.  

Ramon liked to advertise his good fortune with having twenty-four-hour pussy always available to him and just out of sight. It was definitely a change for the better with the bad luck of his recent misadventures.

I was relieved to see him regain his confidence and finally relax once again.

I had a fond hope that the constant look over his shoulder at any loud noise behind him would slowly disappear. It was wise to be cautious, but unnecessary to be always on the lookout for the long, last goodbye.

I had a totally unsatisfying fling with a beautiful showgirl that hung up her six-inch high heels and went back to her suburban roots just outside Chicago. She had made the decision to marry some pious preacher’s son after another John with a wife and kids at home left her whistling Dixie all by her lonesome with the rent money thirty days past-due.

She was a good girl gone bad and unable to cope with the simple facts of her own slow fall into absolute depravity in the midnight hours.  

I felt sorry for her husband-to-be with no concept of the changes in his high school sweetheart. He was in for the shock of a lifetime on the honeymoon providing he was able to survive her physical need for sex and several other deviant practices that he would never be able to discuss with his family or close friends as a topic of conversation.

I knew it would be easy for me to fall in love with the confused showgirl.

The fetish-minded showgirl went under the stage-name of Carmelita and was billed as a Brazilian bombshell to scoop up the homebodies that were hoping to find something a little unusual and strange to file in their memory banks. Of course, her name wasn’t Carmelita and she had never been out of the country in her entire lifetime. Her real name was Janice and she was born and raised in a suburb of Chicago as the middle child of a church-going couple that secretly used spanking and submissive behavior to spice up their lackluster lives behind closed doors.

I suspected that the innocent-looking Janice had been exposed to that lifestyle at an early age and she never looked back on a lifetime of proper behavior. Now, she was desperately returning to normalcy in an attempt to right her listing boat before she capsized and went all the way down to Davey Jones locker in shameful disgrace.

I empathized with her need for normalcy and down deep in my soul I knew she was probably making the right decision even though it was depriving me of her comfortable companionship at a time when I was on a fast lane to depression revving my engines all the way.  

I did have a certain level of appreciation for the dazzling Janice to arouse my carnal instincts with her nicely trimmed twenty-something bush. She never failed to inspire me to shoot long lines of creamy man juice each time she bent over suggestively in front of me. I loved the way she would look over her shoulder at me.  She had that look that said,

“Just get it inside real deep and make me take it all the way up the ass, Mister.”

We didn’t play games with each other when it came to sex.   

I recognized her obsession with all things anal the first time I was able to get her to lower her panties behind my locked office door.

Life after Janice was admittedly a bit boring.

At least, until I followed Ramon’s chain of thought about multi-relationships and opted to take Jackie and Jill’s company on a live-in basis right out in the open and risk the snickers and dirty jokes about keeping two girls satisfied at the same time.

The truth was that the more aggressive Jackie was a dominant personality in her attitudes and she tended to play rough in a way that was like catnip to the more sedate Jill’s carnal needs. They were the Captain and crew of one of the mid-sized pleasure boats that had several sleeping cabins below decks.  The both of them were accustomed to entertaining high rollers more interested in nailing enthusiastic and obedient fully comped pussy. Winning at the gaming tables with repetitive success was less of a priority than having a good time with lots of free female entertainment and unlimited booze in every direction.

 Of course, most of the full-time casino employees were aware of Jackie’s inclination to be on top with a female underneath her muscular legs, but most of the tourist types at the tables only saw her pert boobs and luscious ass cheeks placed right on the line and ready to dispense memories to savor for a lifetime of ordinary living.

I never doubted her ability to project feminine charm when it was for the good of the casino.

She constantly hustled for a nice tip for both her and Jill.

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They worked as a team to put some horny married guest through his paces. The girls drained him of all his nasty urges to drag the closest female down to his level of filth and degradation and never let a customer leave without a happy ending.

Most of the married marks carried a silent dark traveler that constantly chewed at their conscience filling them with a sense of guilt. The mostly middle-aged men were up to their necks with hidden urges to degrade and humiliate some beautiful strange girl in a way they would never pester their wives or secret girlfriends.   

The casino girls knew their place in the game of chance and seldom made waves because the benefits were substantial and the gratification was truly immediate.

They might go home with tired, limping asses, but their purses were bulging with monetary rewards that school teachers or waitresses could only dream about on budgets that were stretched tighter and tighter than a pussy that always stayed on the shelf.

 Jill’s expertise was in the art of oral gratification. She had a long, pointed tongue and was not afraid to put it to good use in those places that men found totally irresistible.

The first thing I did after a long shift of tangled chaos was to get Jill down on her knees between my legs and keep my fingers twisted in her beautiful hair to guide her mouth into a good angle to make my cock eager to please the back of her soft white throat.

I loved the way she expertly fought off the gagging reflex and gobbled up my long dick with her lipstick covered lips.

She liked the hot red shade that lit up my groin with a fire of desire burning fiercely like some runaway wild-fire. Jill never failed to stir me up like the driving force of seldom experienced winds. Her passion was deep and strong, but I would still have to give the edge to Mother Nature.

The little imp Jackie would often take advantage of my shameful display of rutting pleasure as I searched relentlessly inside Jill’s wet and wonderful mouth for her trigger of release. I knew it would end with me pumping long lines of creamy deposits into Jill’s gullet and watch her swallow desperately until it was all safely in her flat tummy.

Jackie’s technique was to trap my head between her jiggling ass cheeks and rock and roll her bottom from one ear to the other rubbing her bared feminine folds and her crack on my face until she succumbed to a devastating orgasm.

There were moments when I feared she would get so carried away with her waves of pleasure that she would rob me of my last reserves of oxygen and throw me into a state of unconsciousness.

When Jackie and Jill were both stark naked, they looked so much alike that I thought of them as twins.

Sometimes they would be working me at both ends and I was not quite certain who was on the top and who was on the bottom. My only clue was that Jill had a more pointed tongue than Jackie. She had no inhibitions about using it in all those places that made me wiggle and squirm and sigh with pleasure at her busy mouth. In any event, they were so evenly matched that any fair-minded referee would have to call it a dead heat and declare a tie.

It was in the pursuit of anal delights that I had to award Jill the blue ribbon for carnal pleasure skills because she had the tightest sphincter I had ever had the pleasure of penetrating.  She made no bones about her need to keep my cock buried deep inside until she reached that all-important release point that all females agree is the culmination of their highest expectations.

On the other hand, Jackie was sort of noncommittal about the three-way process, but I suspect her reluctance to gush about the results was more of a defensive move to protect her reputation for bisexual preferences than her personal choice.

I felt that in a one on one situation, Jackie would lose a lot of her anti-male inhibitions and she would push her ass back for more cock at the drop of a hat.

I noticed that both Jackie and Jill liked to work as a sort of tag team when it came to spreading their legs and getting fucked the old fashioned way.

Strangely, they seemed to exude different signals when taking it flat on their backs and with their legs almost straight up in the air or on my shoulders.

Jackie was all hot to trot and begged to be pounded hard and fast.

On the other hand, Jill liked it slow and gentle and liked to push my hand back to play with her rear door whilst I was still buried up to the hilt in her pretty pussy. She was the one that made the animal-like grunts when I was flooding her pussy with my boy-juice.

I was surprised by that because it was the sort of instinctive reaction I would have expected from Jackie.

In fact, Jackie was the one that purred like a kitten, when she was taking the cream from my happy joystick and she acted so feminine that I had the paranoid suspicion she was making a mockery of my fucking efforts. It took a flood of kisses and licking love bites to convince me that she was really feeling the moment and not faking it for my enjoyment or for the entertainment of those watching us act out the oldest show in the annals of human existence.

I was also surprised that we three had evolved into a sensual unit of spanking pleasure shared equally. We all enjoyed the slaps and tickles of heavy hands on pussy, boobs, and asses with no sense of guilt or shame.

I found that this kind of spanking foreplay often led to a hot and heavy session of three-way anal activities that we all enjoyed with equal enthusiasm.

I had no desire to change my pair of favorite partners and was entirely happy to stay indoors with my two best friends at every opportunity.

It was a high point in my journey away from home in the Big Apple.

 

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Written by 3FingerKelly
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