This story is intended for your reading pleasure. The characters engage in sexual activity without the use of condoms. But, please remember that, in real life, we all need to take precautions. Be safe and "cover that thing up" before using it! And enjoy the story....
Tag Teaming The Escorting Begins By Jason Moore
Reggie and Dwight were back at home following their vacation in Negril Beach and that chance encounter with an American photographer, Colin Montgomery. It had been a hard day working on the farm and they simply wanted to relax. Dwight settled in at the computer and decided to log onto the escort site that Colin had developed for them. To his surprise they had over twenty hits already and several emails.
"Hey, Reg, come and see this," Dwight told his friend as he clicked open the email box.
Reggie opened the first email from 'Hungrywhtbtm'. The message was brief, but to the point.
'Very interested in your...uh...services. Below is my picture with a brief bio. Again very interested in that 'Full Service" agreement. Hit me back if interested.'
"Damn, what do you think, Reggie?" Dwight asked.
"Well, let's see," Reggie answered as he scrolled down.
They read on. Hungrywhtbtm was actually Harry Miller, a 41 year old, self-made millionaire who lived in West Palm Beach, Florida. He owned his own realty company and lived alone. His picture showed a man standing in a circular drive before what appeared to be a Spanish style home. He was 6'2" and said he weighed 190 pounds.
"Well, whatdya think?" Reggie asked.
"Let's look at the others," Dwight suggested.
They read the other emails, but, none of the other guys had included a photo. Reggie re-opened Harry's email. After discussing it further, Reggie sent a standard regret to the other four indicating the timing just wasn't good right now. He then responded to Harry in his best business like rhetoric.
'We are interested in coming to West Palm Beach and are available the last weekend of this month. We will require a down payment of $500.00 and round trip airline tickets from Montego Bay to West Palm Beach for Reginald Davis and Dwight Steel will need to be purchased in advance. The flight must depart on Saturday morning and return the following morning. Your payment must by cashier check in either of our names and mailed to the P.O. Box listed on our site. Upon receipt a confirmation email will be sent." They read and re-read this response before Reggie clicked the send button.
"Well, looks like we're in business," Dwight laughed as he slapped his friend on the back.
The following night, after another hard day at work, Dwight logged onto their site and saw that 'Hungrywhtbtm' had already responded.
He called out to Reggie who joined him at the computer. Dwight opened the email and they both read.
'Thanks for the reply. A cashier check for $500.00 has been purchased and is being sent today by overnight courier. Two e-tickets will await you in Montego Bay on flight 7346 departing at 7:10 p.m. Looking forward to seeing you on the 25th. Harry.'
Included were directions to Harry's home from Palm Beach International Airport and a message that a car had already been reserved in their names at the Hertz counter in the airport.
"Well, that was quick," Dwight said.
"And easy!" Reggie added.
"We got two more emails to read," Dwight noted as he returned to the In Box.
The first one was from some guy in Washington DC and the next was a guy from Miami, Florida. The guy in Washington seemed okay, but the guy from Miami, Brock Summers, was slightly more interesting. He was a retired U. S. Marine who now ran his own security business. He, like Harry, was also 41 years old and claimed to have very lucrative business accounts with some of the most wealthy home owners in the area. He, also like Harry, was interested in the 'Full Service" agreement. He also included a photo of himself lounging beside a swimming pool.
Again after some discussion, they decided to decline on the first request and Dwight copied and pasted in Reggie's previous response from the email they sent to Harry, changing the particulars and suggesting the first weekend of next month.
"Colin was right, buddy," Reggie told his friend. "This could make us rich!"
"Yeah a cool grand on back to back weekends, who would have thought it." Dwight added.
Two days later Dwight gave the farm owner an excuse to leave for a long lunch and he drove to their post office. Sure enough, the package from Harry was there already. There was also a package from Brock Summers. He drove by the bank and deposited both cashier checks before returning to work.
"Well, buddy," Dwight told his friend, "we now have one thousand dollars in the bank."
They slapped hands and chuckled at their new found income. As the days went by they continued to get hits on their site. Several more emails were reviewed and, by joint decision, the sent their standard regret to wait until they actually made their first couple of trips to see how things went. They each purchased some new clothes for their first trip. On the 25th they had no problem boarding their flight and were pleased to see Harry had purchased seats in the first class section even though that was not requested. Upon arrival at Palm Beach International Airport, Reggie and Dwight, each with only a carry on bag, quickly got the car rented and were en route to Harry's home in no time.
The directions Harry supplied were very easy to follow and it didn't take long to get there. Harry lived in a gated community. Security let them in and Reggie and Dwight were soon pulling up the circular drive they recognized before actually seeing the address. The front lawn was meticulously manicured. As they both got out and retrieved their carry-ons from the back seat. The front door was opened and there stood Harry Miller in khaki shorts and a white Polo shirt. They all greeted one another as Harry let them in.
"Damn, you're pictures definitely do not do you guys justice," Harry remarked.
"Well, thanks, that's very kind of you," Reggie said.
"You have a nice home, here, Mr. Miller," Dwight added.
"Please, guys, call me Harry. No need to be so formal," Harry said. "Why don't you have a seat here," Harry added indicating the meticulously decorated living room. "I'll put your bags up."
They handed over their bags and strolled off into the living room as Harry literally ran up the stairs with their bags.
"How about a drink?" Harry suggested when he returned.
They all got a drink and Harry led them on a brief house tour ending in his large, gourmet kitchen. Two large glass doors led from the side of the kitchen out into a large yard complete with swimming pool and a large gazebo fitted up for al fresco dining.
"I have reservations for dinner tonight, but was thinking we could hang out by the pool until then, if you want," Harry then suggested.
"That sounds great," both Jamaicans responded as one.
They both were doing there best to hide their wide eyed awe and project an aura of total sophistication. As they stepped outside, Harry pointed out the bath house at one end of the Olympic size pool.
"I keep extra swim trunks in there just for occasions like this," Harry noted. "Why don't you guys go find something and I'll be right back.
"Damn, this place must have cost him a couple million," Dwight said as they entered the bath house.
"Maybe Harry will be a repeat customer," Reggie laughed.
They spied some wire baskets on shelves against the back wall. Minutes later they were each changed into swim gear. Reggie found some box cut briefs that barely concealed and almost seemed to amplify his bulging crotch and Dwight opted for a looser pair of trunks. They grabbed some towels and headed back to the pool. Reggie immediately dove into the deep end as Dwight took their towels to a lounge chair by a table where they had set their drinks. He sprawled out on a chaise lounge just as Reggie poked his head up near the side of the pool. Water rolled down his dreads as he smiled over at his friend.
"This must be the life," he said.
"Yes, it must be," Dwight agreed as he raised his drink in toast.
Harry reappeared seconds later wearing some bikini style briefs. Reggie and Dwight were impressed that this 41 year old guy had kept his body in such good shape. He was not overly muscular, but did have a lean, toned physique.
"How's the water?" Harry asked as walked over by Dwight and set his drink down on the same table.
"Feels good," Reggie smiled back at him. "Why don't you loin me?"
"Sounds good to me," Harry answered.
Dwight looked agape as Harry walked toward the pool. His butt cheeks were fully exposed. Harry was wearing a thong. He couldn't resist commenting.
"Nice ass, Harry!" Dwight quipped.
"Well, thanks," Harry answered as he looked back over his shoulder and wiggled his ass. "It likes to come out to play," he chuckled just before diving into the pool.
"Damn, this is gonna be one fucking hot trip!" Dwight muttered to himself.
Reggie and Harry began to frolic in the pool, tossing a nerf ball around, laughing and splashing. Dwight then finished off his drink and headed to the pool. Diving into the deep end, he swam across and then back again. He joined in the nerf ball tossing. He tossed the ball to high for Harry to catch and it bounced off the water and onto the tiled decking. Harry swam to that side and pulled himself out of the water between the handrails of the step ladder. It was just out of his reach and Dwight was right behind him in a flash.
"Here let me help you," Dwight said.
He propped his feet on the under water ledge that ran the whole circumference of the pool. Holding the handrail with one hand, he rubbed Harry's ass with the other. His finger and thumb slipped around the thin waistband and pushed it up further. Reggie was soon beside them and he reached out to rub Harry's ass cheeks.
"Nice ass," he commented.
For his part, Harry quit trying to reach that ball, preferring, instead, to let those two black studs explore his exposed ass while he just lay there bent over the edge of his pool. As Derrick slid the thin strip from Harry's ass, pushing it aside, Reggie slid his hand into that ass crack and quickly found what he was looking for. His finger flicked at Harry's rosebud several times. Harry reached back and spread his ass cheeks open. His puckered hole was now laid bare. After rubbing it a few more times, Reggie pressed the tip of his finger against Harry's tight sphincter and then pushed inside.
"Aaah, yeah,...yeah," Harry sighed as Reggie sunk his finger in knuckle deep.
"Damn, this is a tight fuck hole," Reggie announced as he began to finger that ass.
"Looks good enough to fuck," Dwight added. "Let me see."
With that, Dwight also shoved a finger inside. With both guys fingering him, Harry began to moan and gasp.
"Oh, yeah, open me up, guys. Prime that ass," Harry directed.
After several minutes, Dwight pulled free and literally jumped out of the pool. He stripped off his trunks and squatted down before Harry.
"Let's see what Harry can do," he said as he stroked his hefty dick.
"Oh my God, that is huge," Harry exclaimed.
"Yeah, but I'm sure you can handle it," Dwight answered.
Without a further word, Harry opened his mouth and Dwight pushed himself inside. Harry began to lightly suck while running his tongue over the bulbous head and glans. He quickly stepped it up a notch and was soon bobbing back and forth on Dwight's thick dick. Dwight then watched as his friend got on the low rung of the ladder, leaned in, and ran his tongue up the crack of Harry's ass.
"Let's get rid of these," he then suggested as he tugged at Harry's briefs.
They were quickly tossed aside and Reggie took his place again. He wrapped his arms around the handrails and used his hands to pry open Harry's ass cheeks. He then leaned in again and began to run his tongue up and down his ass crack. This caused Harry to mumble a muted moan.
"Yeah take care of that ass, Reg," Dwight encouraged.
With one hand holding the base of his dick and the other on top of Harry's head, Dwight began to hump his hips, face fucking Harry.
"Yeah, suck my dick, man. Yeah that's it, suck it good," Dwight encouraged.
Meanwhile, Reggie used the tip of his tongue to poke at Harry's tight orifice. With his fingers applying more pressure, Reggie opened that baby up and dug his tongue inside.
"Mmmmph...mmmmppphhh." Harry mumbled again.
"I think he likes that," Dwight chuckled.
"He'll like it even more when he gets my big black dick up inside this baby," Reggie answered.
With that he spat a thick glob of spittle into Harry's exposed hole. Using a finger, Reggie pushed his spittle inside of Harry's tight bung hole. That finger was quickly followed by another. He repeated that several times, feeling Harry's ass loosening up and getting nice and slick. By then, Dwight had Harry's head in his big hands and was forcibly fucking his hungry mouth.
"Yeah, yeah, suck my dick, man. Suck it," Dwight commanded.
Reggie climbed up on more ladder rung and deftly slipped out of his boxers. He began to slap Harry's ass cheeks with his dick before rubbing it up and down his ass crack. This elicited more muted sighs from Harry. Reggie drooled several thick globs of spittle into his hand and moistened his dick.
"You want this dick up your ass, don't you Harry?" he asked.
"Mmmpph, Mmmppphh," came his reply.
"I think that means yes," Dwight laughed.
"Well open that baby up, then," Reggie demanded.
Harry then pulled on his ass cheeks exposing his puckered hole to Reggie. Reggie pressed his dick head against that tight opening. With a muted grunt from Harry, Reggie shoved himself inside. He pulled out and quickly shoved himself inside again. He repeated that teasing insertion several times. Then on the sixth time, Reggie held himself there and began to slowly shove more and more of his dick. He watched intently as his big black dick forced its way inside Harry's white ass and those ass lips stretching out tightly around his girth.
"Yeah, come on Harry, loosen that ass up. Relax, man. Let me get this baby into that tight ass," Reggie encouraged.
"Damn, it's so big," Harry grimaced as Dwight pulled his dick free for a few seconds. "Ohh...aaaahhh...."
He didn't finish that last comment as Dwight shoved his dick back into Harry's open mouth. When Reggie was finally buried up to the root, he wrapped both arms around the handrails and grabbed onto Harry's hips. He wiggled his own hips and dug his dick deep into that tight fuck hole.
"Damn, Dwight, you're gonna love this fucking ass, man. It's nice and tight," Reggie told his friend.
"And you're gonna get off on Harry's talented mouth," Dwight said.
Reggie then began to hump his hips, watching his friend and trying to stay in syncopation with Dwight's own thrusting motion.
"Man, there's nothing like watching a big black dick fucking some white ass," Dwight told his friend
He watched Reggie's thick dick split open Harry's ass and plunge in and out in a steady rhythm. Harry's fully stretched ass lips gripped his friend tightly and pulled out and pushed in with each of Reggie's deep plunges.
"Man, this is some fucking tight ass, buddy," Reggie said again. "Mmmm, yeah, I'm gonna fuck this baby good. That's what you want, isn't Harry?"
With that, Reggie picked up his pace. In seconds he was plowing that white ass like there was no tomorrow. This went on for several minutes with both black studs using Harry's holes for their ultimate satisfaction. Finally, Reggie planted his dick deep inside of Harry and wrapped both arms around his waist.
"Let's move up to the lounge chair," Reggie then indicated to all.
"Sounds good." Harry agreed as he felt himself still impaled by Reggie's massive dick.
Reggie literally lifted Harry with him as he climbed the ladder out of the pool. With his dick still buried up Harry's ass, he carried him and took them both over to the nearby chaise lounge. He set Harry down into a doggie style position and quickly continued where he had left off. Dwight stood by stroking himself.
"You gonna hog that ass all to yourself?" Dwight finally asked.
"Naw, come on over and get you some," Reggie laughed as he pulled himself free.
Dwight was soon in place and guided his dick inside of Harry's proffered fuck hole.
"Oooh, yeah, fuck my ass. Fuck it good," Harry sighed.
"Yeah gotta give the customer what they paid for," Dwight chuckled as he plunged his dick in balls deep, eliciting a loud grunt from Harry.
As Dwight began to fuck Harry's ass, Reggie slid down into the back of the lounge and pushed his swollen dick into Harry's face. Harry reciprocated by quickly taking that massive member into his mouth.
"Yeah, suck that dick while I pound your ass," Dwight encouraged from behind.
This wild fuck session lasted nearly an hour more as both black studs took turns tag teaming that white ass in a variety of positions out by Harry's pool. When they were both sated and ready to explode. Dwight and Reggie stood beside the lounge while Harry sat in it and they all jerked their dicks furiously.
"Aaah, yeah, I'm gonna shoot," Reggie said first. "Eat my cum, man."
With that, Reggie pointed his dick at Harry's face. A huge glob of cum spurted out onto Harry's nose and chin. Harry opened his mouth and took several more volleys of Reggie's cum onto his outstretched tongue. When Reggie pulled his hand from his dick, Harry grabbed it and took him into his mouth. As he siphoned out every last drop of cum, Harry, too, shot his load.
"My turn," Dwight then said.
Dwight then proceeded to spew copious amounts of his cum all over Harry's face.
"Aaah, yeah," he sighed as he felt that last spasm and watched it spit out onto Harry's cum soaked face.
Both black studs stood there as Harry took turns sucking their dicks dry.
"Mmm. Yeah. Taste's good. Mmmmm, yeah," Harry muttered as he licked, sucked, and gobbled down every last drop.
To be continued.....