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Chapter 63 Wild Ride to Miami
“It’s going to be a little rough, so fasten your seat belt,” announced the pilot as the Bombardier Global jet began its descent into the Miami-Dade Airport.
“Must be Danica,” said Portia gathering up the strapon cocks and harnesses and placing them back in the Red Sox bag.
“Weather report said it going to miss the US,” said Lou.
“Hurricanes are like women, they like to change their minds,” said Mike stepping into his boxer shorts.
The pilot’s announcement prompted Stacy along with the others to begin searching frantically for their clothes. Stacy and Portia had led a five hour in-flight non-stop orgy that made the time pass quickly. It also provided opportunity to medicate everyone with a powerful aphrodisiac that would last the weekend.
Other than a few comments about being exceptionally horny, no one had noticed the six Posse members and their female companions had been insatiable throughout the flight.
Stacy was determined to maintain her anything goes party girl image within the Posse. Two days before, her PowerPoint presentation of a complex money-laundering scheme for the billions the Posse expected to receive from the exclusive US distribution of cartel cocaine had impressed Mike and Zack.
They should have been impressed. The world’s foremost expert on the topic had prepared it. The Posse began to consider Stacy a contributing member not just an unusually willing and skilled whore.
“That’s all wrong,” said Stacy complaining to Portia. “I don’t want them to think of me as a true partner. It’s dangerous, especially now.”
“I agree. So the answer is we fuck our brains out on the flight down. By the times the wheels touch down, they’ll consider you the chief bimbo in residence and nothing more. Sir Charles told me about an experimental drug that will increase their sexual activity for three to five days. I know how we can get them to apply it,” said Portia.
“How,” asked Stacy?
“They’ll take it up the ass,” said Portia.
A key part of their plan was to create as relaxed an atmosphere as possible so Mike and the others would lower their guard. The initial phase had gone well judging by the look on everyone’s face as the plane approached the runway.
Stacy had initiated their plan immediately after takeoff. “I’m flying naked and joining the mile high club,” said Stacy standing to unbutton her blouse as soon as the jet cleared the runway at Lexington’s Hanscomb field. Stacy’s blouse was already half unbuttoned when she heard the wheels being retracted into the fuselage.
“What,” asked Mike looking puzzled at her behavior? The importance of the trip to the fortunes of the Posse had put him into a thoughtful mood Stacy needed to lighten.
“I’m in the mood to party. You said we would have some fun on the trip. I’ll be very serious and ladylike when we get there. I promise. But for now, I want to enjoy the flight by screwing everyone,” said Stacy slipping the blouse off her shoulders. “Get naked, girls. Let’s join the Posse’s mile high club.”
“Why not,” said Wynona standing in the aisle to remove her shirt then playfully throwing it at Stacy who responded by tossing her blouse toward Wynona? Wynona’s fiery red hair reminded Stacy of her recent auburn tresses. Seconds later, their bras flew across the plane. Wynona’s landed on Mike’s head.
Stacy quickly straddled him and pulled the lacy D cups on top of his head. “You look cute like a Mousketeer,” said Stacy before kissing him passionately.
“You are one cock crazy cunt,” said Mike embracing Stacy enjoying the feel of her hard nipples against his face. “Maybe I should divorce Connie and marry you.”
“No way I’d marry you. My husband has to be a virgin on our wedding night. Suck my tits. You’re going down,” said Stacy placing her breasts at his lips. Mike obliged by capturing her nipple in his mouth then sucking in the entire areola.
“I brought toys for everyone,” said Portia pulling a large nylon Red Sox sports bag from under the seat in front of her.
“Let’s get wild,” said Katyln, Zack’s ex wife stepping in the aisle to unzip her skirt and let it fall to the floor. Katyln had a well-tanned compact muscular build that matched her ex-husbands. She and Zack owned and managed a chain of Metro Boston health clubs. Her position required her to stay in shape.
“What toys did you bring, Portia,” asked Chloe pulling her cotton shirt over her head. Brad had recently paid for Chloe to have a breast augmentation and she was anxious to see the other’s reactions to her new chest.
“Strap ons, those look terrific, Chloe,” said Portia adding a high school girl’s squeal to her voice as she pushed the end of her ringed tit in Lou’s open mouth.
“This is good. I thought the flight would be boring,” said Veronika, a recent immigrant from the Ukraine Bobby had helped with a police problem concerning the distribution of heroin. This was her first time with the Posse. Veronika was well over six feet but skinny almost to the point of appearing emaciated. She pulled her shirt over her head.
Braless, her dark chocolate nipples and mannish chest caught Stacy’s eye. “I want to eat your pussy, Veronika,” yelled Stacy enthusiastically.
“I get her first,” said Wynona turning Veronika around to kiss her.
“Give me one, Portia,” said Stacy rapidly undressing in the aisle.
“How many of those things do you have in that bag,” asked Lou watching Portia remove a handful of the oversized dildos and harnesses?
“Don’t worry, Lou. I brought strapons for everyone. You’re blue, Stacy,” said Portia tossing Stacy a harness with a bright blue plastic dildo nine inches in length mounted on the crotch. There was a plastic squeeze bottle of kiwi flavored Wet taped to the side of the dildo. It would have taken an expert to determine the product had been heavily laced with an aphrodisiac.
“Lt. Michael Cabreeze, the whores of the Commonwealth of Massachusetts have found you guilty of lascivious conduct and mopery. You are sentenced to a thunderous butt fucking to be carried out in front of your peers. I am going to stir your shit,” said Stacy now naked as she stepped into the harness and pulled it over her hips. Sentence to be carried out immediately. “Strip, bend over, lift your sack, and spread them,” said Stacy.
“You’re insane. You’re not going to stick that thing up my ass,” said Mike laughing as he began to undress.
“What’s the matter, Michael? Can’t take a little butt action? Don’t want your shit packed? Little rose bud’s too tender for Stacy’s hard prick,” said Stacy stroking lubricant onto the dildo as she waved it in Mike’s face. “You know what UK’s soccer hooligans say about male anal sex?”
“No, what do they say,” asked Mike his mood lightening?
“Guys who fuck only girls are Nancy boys,” said Stacy. “It takes a real man to fuck a man.”
“Sounds like the Brits,” said Mike.
“Stacy and I thought it would be nice for a change if we girls do the fucking,” said Portia reaching into the bag to retrieve more of the brightly colored strapons and tossing them to each of the now naked girls. Portia quickly fastened the harness around her waist and thighs then climbed up on Lou’s seat one foot on each armrest.
“Suck it, Nancy boy. Show me how you used to suck priest dick at St. Francis’s in Southie,” said Portia taking hold of Lou’s head and pushing the yellow dildo into his mouth. Portia was pleased Lou did not protest but joined in the fun. The others women imitated Portia forcing the strapon cocks into their partner’s mouth.
At the front of the plane the fight attendant was watching the goings on with wide eyes. Just when you believe you’ve seen it all thought Myrna opening a bottle of champagne.
“Will you hear my confession, Father O’Rourke, if I swallow your holy load,” said Lou as he licked and sucked the cock? In Lou’s case, he was reenacting actual events. Over the course of his twelve years in South Boston’s Catholic schools, he had engaged in oral and anal sex with several priests including a young Jesuit just out of seminary named Sean O’Rourke.
Lou had drunkenly confided to Portia how he had fallen in love with the handsome young priest and availed himself of every opportunity to serve him. One of his happiest boyhood memories was when the football team went on a spiritual retreat to a seminary in Western Massachusetts and he got to spend the entire night in Father O’Rourke’s arms.
As Lou’s lips and tongue applied themselves to the realistic contours of the finely crafted dildo, he recalled other memories. Some of the most erotic were in the church’s confessional when he had knelt under the priest’s robes slowly and quietly sucking his cock while the good father heard the confessions of parishioners.
One vivid memory was when Mary Casey the prettiest girl at St. Francis Xavier High School confessed to the sin of lust. She’d performed orally with Coach Lewis, the football coach. Mary described in detail several occasions where she had climbed under the Coach’s desk and wound up with a mouthful of semen she had dutifully swallowed. Mary, a devout Catholic, had been tormented by the thought that swallowing the Coach’s living seed was a mortal sin since it was not used to procreate.
She also asked the Father O’Rourke whether it was a sin for Coach Lewis to use his mouth to pleasure her. Mary had been unable to locate any passages in her Baltimore Catechism defining whether she committed a mortal or a venal sin by allowing Coach to lay her on his desk and used his mouth to make her feel, in Mary’s words, gloriously happy.
Father O’Rourke had cautioned Mary to speak to no one else of her meetings with the Coach upon pain of excommunication and losing her immortal soul. He pointed out Coach Lewis was under enormous pressure to continue the team’s winning record and return them to the state championship. Lou faithfully recalled the exchange ending the confession.
“Coach wants me to give up my virginity. So far, I’ve only played with his cock and used my mouth to make him come. What should I do, Father?” said a tearful Mary.
“Tell Coach Lewis you’ll give yourself to him the night he wins the state championship. Now, not a word of this to anyone, say ten Hail Mary’s and five Our Fathers and repeat the Act of Contrition with me,” said the Priest.
“Yes, Father,” said Mary.
After Mary’s confession, Lou and Father O’Rourke had retired to his quarters in the manse for an afternoon of fucking that left Lou gloriously happy, too.
Lou had been heartbroken when Father O’Rourke had been called to Rome to serve the Holy See. Lou attributed the fact his cock became very hard very quick to the power of the long forgotten first love but that was only partially true. Drugs concealed in the Wet had invigorated his sexual plumbing to a state his poor physical condition, drinking and drug abuse normally prohibited.
“Unzip me, sweetheart,” said Lou. “You’ve got me so hard I’m going to blow my load.”
“I think our big strong cops have sucked dick before,” said Chloe to the others as she thrust the lubricant coated head into Brad’s eager mouth.
This is working thought Stacy looking up and down the aisle of the luxurious executive jet Mike had leased for the weekend. All six of the females were wearing the strapons. They were custom made by Crofts and McAdams, a venerable London firm that had been in the marital aids business for over a century. They had supplied the royal family with a variety of products always employing the highest quality material and most expert craftsmanship. Many of Europe’s nobility had felt the impact across their backside of their internationally regarded Malacca canes.
The strapon dildo was an exact replica of Prince Albert Edward’s penis, the notorious rake who was the son of Queen Victoria and went on to become King Edward VII. His member was well known throughout London society. Christened The Punisher by those who experienced it and famed for the oversized mushroom head, it figured prominently in many divorce cases of Prince Eddie’s time and was reputed to have fathered dozens of bastards. Before the trip, Stacy and Portia had rigorously tested it using Monk and Les as guinea pigs.
A three-inch wide band of hand-tooled soft belt leather circled the wearer’s waist. One-inch wide straps girded both thighs providing superior stability, comfort, and control. On the female’s end of the nine-inch dildo was a smaller dildo of a more modern design. A five-inch vaginal dildo contoured to maintain contact with the G-spot anchored the prodigious tool and provided serious pleasure to the wearer during use. Its textured patented surface stimulated the vaginal walls.
The front of the harness did not neglect the clitoris. An adjustable triangle of soft silicone rubber nodules mounted on the inside of the V-shaped pubic pad pressed into the clitoral area. Both Stacy and Portia had been highly satisfied with the erotic sensations resulted from their vigorous pummeling of Monk and Les’s assholes. They had spent hours testing the strapons and the effect of the drug contained in the Wet lubricant. Only the utter physical exhaustion of the two boys put an end to their efforts.
“This is so comfortable,” said Wynona tightening the waist. “And it’s made so well, not like that cheap crap you get in the stores.”
“Oh fuck, this feels great in my pussy. I got to have one of these,” said Chloe inserting the smaller dildo into her vagina and experiencing the pleasure it afforded when it contacted Dr. Grafenberg’s discovery.
“I’ve got the email address of the company if anyone wants to buy one,” said Portia helpfully.
“Join us Myrna,” said Stacy to the fiftyish flight attendant who was making drinks in the front of the plane.
Why the hell not thought Myrna as she eyed the naked women getting into the strapons. Looking much younger than her fifty-two years, Myra had kept her figure because she knew her job depended on it.
Over ten years of charter flights, her willingness to do whatever it took to make the passengers happy had been the secret to her employment longevity. At twenty five thousand a flight, passengers felt entitled to more than free drinks. Sports figures, rock bands, and the occasional business executive had treated Myrna as part of the accommodations.
They hadn’t neglected her anus either. Myra recalled the first time she had engaged in anal sex. It occurred during a drunken drug orgy while transporting a rock band back to London after their American tour. The drummer who was gay mistook Myrna’s upturned asshole for that of the band manager. A totally wasted Myna collapsed over a seat had been awakened by the insertion of a large cock in her rectum.
Finding the sensation not unpleasant she had encouraged its continuance by squeezing her butt cheeks together until the release of a copious load of semen filled her rectum.
She had been mildly surprised when upon withdrawal a pair of sucking lips surrounded her anus to extract its liquid content. It was only when the singer pulled Myra erect and pressed his lips to hers releasing the contents of his mouth he realized he had just sodomized someone outside his normal gender preference.
“Sorry about that, love,” said the singer licking his lips.
“My pleasure,” said Myrna after swallowing.
Since that first and unexpected anal intrusion, Myrna had developed a taste for all things anal and had expanded her own sexual preferences to both genders.
“There’s not a seat on the plane I haven’t been screwed in by both sexes,” Myra drunkenly bragged to coworkers at a recent office party. “Once I took on an entire NBA team and their coaches. I did anal with the seven-foot center. I didn’t shit right for a month.”
But when she learned the passengers on the flight to Miami were policemen she thought it would be a sedate trip. But when Stacy exposed her incredibly beautiful breasts and Portia began handing out the strapon dildos, Myra knew she was in for an interesting flight.
“Here, Myrna, you can be the silver,” said Portia tossing the gleaming dildo in her direction.
“I’m in,” said Myra slipping out of her uniform jacket as she caught the dildo with one hand.
“All right, ladies, let’s form the caterpillar and show our Nancy boys how it’s done. Then we’ll see whose man enough to join us,” said Stacy taking up a position in the middle of the aisle. Stacy braced her legs against the seats on each side and squatted down supporting herself with the armrests.
“Fuck my ass somebody, please,” yelled Stacy in a tone of mock desperation.
“Me, I’ll do it,” said Wynona taking a position behind Stacy. She smeared lubricant on Stacy’s anus, loosening the tight aperture with her fingers.
“Ready, girl friend,” asked Wynona placing the mushroom head against the center of Stacy’s sphincter.
“Give me your best shot,” said Stacy bracing herself as Wynona slowly moved forward driving all nine inches into Stacy’s rectum.
“Oh, that feels good. I feel so full,” said Stacy after she had sounded a loud animal moan from the back of her throat.
“Me next,” said Chloe stepping behind Wynona. Moments later, Chloe delivered a loud slap to Wynona’s flank as she lunged forward to bury the entire nine inches.
“Goddamn, it feels like its coming out my mouth,” cried Wynona between loud grunts.
“After I fuck Chloe, I’m going to do you, Zack. This is going up that tight little hole of yours. You better get it wet and lose so it slides in easy,” said Katyln pressing the dildo to Zack’s lips. Zack laughed then licked the cockhead.
“I can’t wait,” said Zack as Katyln took up a position behind Chloe and began applying lubricant to her anus.
“God it feels huge,” said Chloe as Katyln forced her sphincter to open and accept the dildo.
“How do you want it, Chloe, slow or all at once,” asked Katyln once she was in position.
“I’m a Posse girl, ram that baby in as far as it will go,” said Chloe bracing herself.
“You got it,” said Katyln thrusting forward with a force that was felt along the caterpillar.
“I felt that,” announced Stacy at the front.
“Me too,” said Wynona.
“That’s why it is called the caterpillar,” said Portia.
“In Moscow, the mafia is bisexual. My boyfriend, Dimitri, had to prove his loyalty once a week by letting his boss fuck him in the ass,” said Veronika taking a position behind Katyln.
“I didn’t use to like anal,” exclaimed Katyln as Veronika impaled her. “But now I just love it. God that’s huge.”
“I’ll take Veronika’s rear,” said Portia kneeling down and applying her mouth to the exposed sphincter. Portia’s mouth and fingers aided by the lubricant readied Veronika’s anus for penetration. A torrent of Russian expletives escaped Veronika’s lips as Portia sunk the dildo home.
“Come here, Myrna,” said Stacy. You can be the head of the caterpillar.”
Myrna clad only in the strapon stepped up to Stacy, leaned down to kiss her passionately then took up a position in front of her in a deep squat. Stacy applied her mouth to Myrna’s rectum then lubricated it with Wet’s anal jelly.
Myra let out a long sigh of deep pleasure as the mushroom head forced open her sphincter then traveled nine full inches into her bowel.
“Let’s show the captain and crew our caterpillar,” said Stacy.
“We’ll have to move in cadence,” said Katyln who had considerable experience in supervising group exercise. “I’ll call it this way: dildo out, step right, step left, ram it in, dildo out, and so on. That way we can move like a caterpillar going forward.”
Minutes later, the three man crew was astonished when to the cadence shouted by Katyln, Myrna opened the cockpit door and the seven hunched over women rhythmically moved forward to where Myrna’s head was between the pilot and copilot’s seat.
“Join the caterpillar and let us fuck you in the ass; then you can do take a ride on our Hershey Highway,” said Stacy.
“Shit yeah, I’m in,” said Ronnie, the flight engineer reaching out to fondle Stacy’s breast.
“Take off your pants and squat down in from of Myrna,” said Stacy.
“Hey guys, we got a real man up here that’s not afraid to take it in the ass,” yelled Wynona over her shoulder.
“Hey, I’ve already fucked Myrna more times than I can count,” said Ronnie kicking his shoes off as he unbuckled his belt.
“But this time she is going to fuck you,” said Portia.
“I got to get a picture of this,” said Curt the co-pilot reaching into his bag for a camera.
“After I let Myrna fuck me in the ass, what do I get to do,” asked Ronnie slipping his boxers down?
“You can stick this anywhere you want, my mouth, my pussy or my ass,” said Stacy taking hold of Ronnie’s cock to stroke it.
“Hey, I want in on this,” said Curt. “How about we take turns flying, Rob?”
“Al right, you go first. After you’ve emptied your gun, come back and I’ll take a shot,” said Rob.
“Lube me up, Myrna,” said Ronnie presenting his hairy butt to her face.
“My pleasure,” said Myrna squirting Wet into Ronnie’s crack then working it into his sphincter with his fingers.
“Ever taken it up the ass before, Ronnie,” asked Rob?
“Sure, lots, the first wife was into strapons,” said Ronnie reaching back to pull his ass cheeks apart then moaning as Myrna inserted two fingers in his anus. “Loosen my hole, Myrna.”
“Hey Gorgeous, want to stir my shit,” asked Rob looking directly at Stacy?
“Love to, how do you want it, dog style, cowboy, or on your back,” asked Stacy?
“On my back so I can play with those tits,” said Rob.
“Smile for the camera,” said Curt focusing on Ronnie’s face as Myrna positioned the dildo in the center of his rosebud.
“Ready to join the caterpillar,” asked Myrna taking a firm grip on Ronnie’s hips?
“Ram it home, Myra,” said Ronnie exhaling to relax as he felt the faux prick slip into his rectum and travel inward straightening a loop in his large intestine.
“Oh fuck,” said Ronnie taking another deep breath attempting to control the cramp he was feeling in his gut.
“That was priceless,” said Curt still looking through the camera’s viewfinder. “Ron’s eyes got wide as saucers as that baby sunk in. This is one for the family album.”
“Caterpillar in reverse,” said Katyln as she began the cadence that took them back to the main cabin.
“Don’t you just love it,” asked Wynona slowly moving the dildo back and forth in Stacy’s ass?
“I never thought I would like anal until Mike showed me how great it was,” said Stacy as they reached her row. “Your turn, Cabreeze.”
“Why not,” asked Mike standing up to kick off his Gucci loafers?
Moments later, Mike’s clothes were neatly folded over the window seat as he stepped in front of Stacy and crouched.
“Loosen me up, please,” said Mike presenting his butt to Stacy’s face.
Mike’s participation encouraged the other members of the Posse to join in, even Zack.
“I’ve been dreaming of this day,” said Katyln pushing two Wet covered fingers in Zack’s asshole.
“Hey, take it easy,” said Zack.
“Sorry, sweetheart but its payback time for all those nights you got me drunk and fucked me in the ass, especially the time you let your old Navy buddy join in,” said Katyln.
“I said I was sorry and you said you forgave me for that. Besides I was too drunk to stop him,” said Zack pushing back slightly in increase the penetration of Katyln’s fingers.
“But not too drunk to shoot a full roll of film of him pounding my holes,” said Katyln placing the dildo head in the center of Zack’s sphincter.
“Hey, it was our honeymoon. Who knew Ed and Zoe were going to be at the same resort,” said Zack. “Give me a couple of inches to start.”
“Zoe, you had to mention that worthless slut who you were fucking every time my back was turned. How’s that?” said Katyln slowly easing the dildo into Zack’s butthole then removing it? When Zack’s sphincter failed to fully close, she aimed the bottle of Wet toward the opening and squeezed hard sending a stream of lubricant inside.
“I’m not the one who played naked Twister with a bunch of college boys then let them gang bang me on the bench press,” said Zack as Katyln slowly shoved the dildo to its halfway point.
“This is a really terrific feeling,” said Zack exulting in how it felt to have the dildo in his bowels.
“You guys sounded like you had a great honeymoon,” said Chloe wistfully as she thrust into Brad’s muscular butt.
“It was a wonderful honeymoon. It was the marriage that sucked,” said Katyln commencing the rocking motion.
“This isn’t so bad in fact I’m getting off on it,” said Mike as Stacy slowly fucked him in the butt.
“I’ll send one to your house with a note telling her how much you like it,” said Stacy.
“Connie and I have split up. She’d filing for divorce,” said Mike. “Let’s get married as soon as my divorce is final.”
“Are you serious,” asked Stacy slowly pulling the dildo out to where only the head remained in Mike’s ass before slowly forcing it in as far as possible.
“Of course, I’m serious. We make a great team. This thing with the Cardozo Brothers is only the beginning. We’re going to be rich as Bill Gates. What’s the matter? You don’t want to be Mrs. Stacia Cabreeze?”
“You’re actually asking me to marry you while I’m fucking you in the ass with a dildo,” said Stacy.
“Not romantic enough, all right, we’ll go to dinner next week, just the two of us and I’ll pop the question. I’ll even get down on my knees if that is what you want.”
“That sounds better,” said Stacy. “I’m an old fashioned girl.”
“The divorce will take six months to finalize. But I want to get you pregnant before that,” said Mike slowly stroking his cock.
“Children too,” asked Stacy?
“You do want them, don’t you?”
“Sure, I can’t wait to have your babies,” said Stacy tightening her grip on Mike’s flanks as she increased the pace and force she was driving the dildo in her future husband’s ass.
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