Tropical Vacation Ch. 08-10

"Here's to good friends!" Jeff said raising his glass.

The others raised their glasses and touched and took a sip of the expensive sparkling wine.

"OK...so how is this bet going to work?" Tina asked.

"Well, I've been thinking about it and I have an idea," Jeff replied pulling three small envelopes from his shirt pocket. "We write down our 'predictions' in secret and put them in the envelopes with our money. Chloe holds them and when she leaves with a guy that will be the final count. The closest to the number of guys who hit on her without going over wins the bet."

"Who says I'm gonna leave with a guy?" Chloe asked Jeff with a troubled look, "I thought I'd be spending the night with you?"

"I didn't say you'd have to spend the night with the guy, just leave with him. What you do after that is up to you. Ditch him if you want or have a quickie or fuck him for a couple hours, then come back and we can go from there. What do you think?"

"Sounds fair to me," Kelly said as he wrote down his guess.

"Me too," Tina agreed and put her prediction and $20 into the envelope and liked the seal.

"So what do I get out of all this?" Chloe asked.

"You mean besides more attention from young, hot guys than any woman could possible imagine and getting to do as you like with one of them? Gee...I don't know?" Tina teased.

"And you get to come back and leave with Jeff once you're done. Then he will take you home and fuck the day lights outta you. What more could you want?" Kelly added.

A sly smile appeared on Chloe's face but before she could say anything, Jeff jumped in with, "Don't ask!"

They all laughed and raised their glasses again.

***

They finished the magnificent dinner around 9 pm, just before Tina had to be at the club for her shift. She kissed Chloe on the cheek and she and Kelly slid out of the booth. She kissed Kelly long and deep but pulled away as his hands moved to her round ass.

"Save that for later...I gotta go," she said then headed for the door.

Kelly sat back down with a frustrated look on his face. Chloe moved close to the troubled young man and ran her hand over the substantial bulge in his pants. He quickly perked up as he enjoyed her talented fingers massaging his hard cock.

"Don't worry big boy, you'll see her very soon," Chloe said soothingly, "But until then, this should help take your mind off Tina." She moved his hand to her silky thigh and increased her attention to his throbbing dick.

"I'd like to take you somewhere private right now and...," Kelly was cut off by Jeff raising a question.

"Does this count toward the number of pickups we have on our bet?"

They all laughed.

"No, we're not at the club yet," Chloe said moving her free hand to Jeff's rigid member, "Besides, I'm enjoying my after diner entertainment." She gave both their cocks a squeeze for emphasis.

"Oh gee...Look at the time. We should be getting over there before Tina begins to wonder," Kelly said jokingly as he looked at the non existent watch on his wrist.

Jeff stifled a laugh and began to adjust himself before sliding out of the booth. Kelly followed suit and stood.

"Kelly's right we should get going."

The two men were met with a pout on Chloe's face. She was hoping to torment them a bit longer before leaving.

"If you insist," she said sliding out of her seat.

Her dress had rode up to a point where it nearly exposed her bald pussy hiding behind the ultra sheer nylon of her hose. She gave both guys a quick look then strutted toward the door not bothering to adjust the hem of her dress. Although the restaurant wasn't as busy as before, all eyes were on her as she left with her two men in tow.

***

Chloe's heart was pounding with the thunderous throb of the music coming from the Inferno Club's powerful speakers; driving her excitement and anticipation to new heights. The short walk across the plaza to the club gave her a chance to lower her dress back to mid thigh range. Not because she was modest, just that she didn't want to show the growing wetness creeping down her thighs. She was so turned on by the thought of what she was going to do that her pussy was dripping wet. Normally this would be so out of character for her to go clubbing to pick up guys let alone guys that were young enough to be her children. She had to admit that the thought of so many men vying for her attention made her feel incredible.

Jeff opened the door for her and he could see the place was packed.

"I don't think we are going to get a table tonight," he said nearly yelling into Chloe's ear.

"I guess not. What a crowd," she replied.

Chloe was scanning the crowd for Tina when a bouncer pulled Jeff aside and talked to him briefly. When he rejoined her and Kelly he had a grin on his face.

"What was that all about? We haven't been here long enough for you to cause any trouble," Chloe asked.

"It seems we have a table reserved in the VIP section."

"How did you manage that?"

Jeff just shrugged then motioned her and Kelly to follow when the bouncer returned a few minutes later. The burly man led the three of them through the crowd to an elevated roped off area and pointed at a booth overlooking the dance floor. He handed Jeff three wrist bands then left. Chloe sat between Jeff and Kelly on the soft velour seat. She noticed a small envelope attached to the 'Reserved' sign on the table with her name on it. Jeff and Kelly watched her open it and read the note inside.

It read simply:

Chloe,

Enjoy your evening.

Randy

"That's sweet! How did Randy know we were coming here tonight?"

She looked at Jeff and he was as surprised as she was. When she saw the big smile on Kelly's face she knew he had something to do with it.

"Alright, spill it young man!" she said with mock anger in her voice.

"I pulled some strings," he replied trying not to look too smug.

Before she could question him further, Tina walked up and placed drink napkins in front of them. Chloe was stunned at how sexy Tina looked in her uniform. She had taken the braids out and teased her hair to a massive mane. She had also touched up her eye make up giving her a more seductive look. The tiny bikini top was straining to contain her ample breasts and her mini skirt seemed extra short compared to the other waitresses Chloe had seen. Tina had on a pair of black platform sandals with 6" heels, but it was the sheer black hose she had worn at dinner that really set her apart from the rest of the servers. Chloe could see Jeff and Kelly were drooling over Tina's outfit as well as every guy near by.

"What'll ya have," Tina asked leaning over the small table; her boobs nearly spilling out of her top.

"A lemon drop please," Chloe answered.

"How about you two?"

It took Jeff a moment but he finally was able to answer, "Beer." When Tina looked to Kelly he was just nodding in agreement with Jeff's order unable to answer on his own.

"I can't take these guys anywhere," Chloe said to Tina as both women chuckled.

When Tina returned with their drinks, she pointed out to Chloe a good place at the bar where she would have the best 'exposure', then went back to serving the other patrons in her section. As the threesome sipped their drinks and scanned the dance floor one thing was very apparent, no other woman they could see was wearing pantyhose. Chloe was going to be 'one of a kind', so to speak, when she went on the prowl.

Chloe finished her drink and a brief wave of nervousness washed over her. She looked to Jeff for some reassurance and he gave her a big smile.

"You look so incredibly sex that you're going to be mobbed by guys! Be sure to keep a good count," he said with a laugh.

That was what she needed. She had Jeff let her out of the booth and headed to the bar. Chloe looked back to see both Jeff and Kelly watching her, so she put some extra sway in her hips and cross in her step to give them a good show. As she made her way to the bar, bodies rubbed against her and hands groped her ass but she didn't mind. It was all fuel for the fire.

When Chloe reached the place Tina had suggested, she squeezed between two young studs on bar stools to order another drink. The two men were unsuccessfully hitting on the female bartender but when they saw Chloe things changed. The stud to her right hopped off his seat and offered it to Chloe who graciously accepted. She ordered a drink then realized why Tina sent her here. There were several guys clumped around this section of bar because the bartender was gorgeous and she was the only women behind the bar.

Chloe got her drink then turned back toward the dance floor, crossing her legs so she could bounce her foot and dangle her heels. The young man who gave up his seat to her made the first advance by asking her to dance. She thanked him but declined, preferring to finish her drink. From that point on there was a steady stream of hot young horny suitors gathered around her. The shine of her hosed legs under the flashing lights drew them to her like moths to a flame. One exceptionally tall and handsome guy with jet black hair caught her eye. He leaned in and put his lips practically on her ear.

"I love your outfit," he said in a husky voice.

"What part do you like best?"

He leaned in again as if embarrassed to have anyone else hear his response.

"Your sexy legs in those pantyhose," he replied.

Chloe smiled then said, "Good answer." She took his hand and slid off the bar stool.

The young mans name was Tom and he was huge. Muscles rippled all over his 6'-6" frame with not an ounce of fat on him. Chloe's pussy began to tingle when ever he looked at her.

She pulled him down to her and said, "Let's get outta here."

Tom plowed his way through the crowd to the exit with Chloe in tow. She was running on her tip toes to keep up with his huge strides. After leaving the club, he led her to his room. She sat on the couch and crossed her legs slowly so he could get a look at her soaked crotch panel. He joined her on the couch and Chloe couldn't keep her hands off him. She straddled his lap and they kissed. The hem of her dress was now at her waist but she didn't care.

"Take your shirt off," she demanded between passionate kisses.

He complied, revealing his muscular chest. Chloe's jaw dropped at the magnificent site. She ground her frothing pussy against his cock still confined in his shorts until she nearly came. It was then she stood up and positioned herself between his legs, bending at the waist to remove his shorts. There were two large wet spots on them. One near the waist band caused by his cock, the other farther down where she was grinding her soaked pussy against him. She tossed the wet garment aside. Tom reached up and freed her boobs from their nylon confinement then played with her nipples while kneading her warm flesh in his massive hands. She placed her hands on his shoulders so he could suck on them and he wasted no time in getting his lips around her right nipple.

"Mmmmmmmm...ya baby...that's it...mmmmmmm...suck 'em good!" Chloe moaned as Tom's tongue flicked her stiff bud in his mouth.

She began to shiver as her orgasm loomed, but she pulled back before it engulfed her. She wanted to hold out to let the tension build higher. Chloe sat on the coffee table with her arms behind her for support, admiring the virile young stud before her.

"So you like my hose?" she asked raising a leg up and pointed her toes at the ceiling.

The shimmer of the nylon encasing her leg held Tom's gaze; his eyes traveling up and down her tantalizing curves.

"Oh ya...they look wonderful...," he replied.

A mischievous grin crept across Chloe's lips then she stood up suddenly and pulled her dress up and over her head. She had Tom sit forward and told him to keep is arms at his side. She pulled the nylon tube down over his head and broad shoulders until it was at his waist. The silky material held him tightly like a nylon cocoon. She sat back down on the coffee table and placed her feet onto his thighs and slowly glided them up and down his sculpted legs. The soft nylon and her warm feet moving over his skin made Tom shudder.

"They feel pretty good too don't they?"

He just nodded.

She moved her right foot to his cock and slid it up and down his slick shaft and her left foot went under his large cum fill balls. His head tilted back and he let out a low grown as she increased the tempo. Her feet switched jobs a couple of times until they were both completely coated in his juices. Chloe then captured his cock between her slippery soles and began to stroke the full length of his throbbing member. Tom's body shook with pleasure and he thrust his hips with each down stroke she made. Just when she felt he was about to cum, she released his manhood from her grip. He sighed in frustration each time she did this. During the intermissions to let Tom cool down, Chloe would feverishly assault her clit through her drenched hose, keeping herself on the ragged edge of orgasm and giving Tom an erotic show. For nearly half an hour she tormented her 'captive' until she couldn't take it anymore. This time when she stopped, Chloe tore open the gusset of her hose and straddled Tom's hips once again. Both of them were panting as Chloe kissed Tom hungrily, pressing her breasts into the velvety material covering his bulging chest. She rocked her hips forward and back, sliding her creamy pussy over his shaft, trying to impale herself on his steely cock. Finally she reached underneath herself and guided him in.

"AAAAAAHHHHHHH!" they cried out together as Tom's cock sank into the depths of her clenching pussy.

Chloe bounced and bucked on his lap, grunting like an animal in heat. In seconds she was consumed by a fiery orgasm. Her body shuddered violently as if she was being electrocuted. This drove her to slam herself down harder and faster on Tom's hard cock setting off a chain reaction of more orgasms within her. The ferociousness of her actions were too much for Tom to handle and he felt the flood gates open as his cock gushed semen into her tight hole like a fire hose.

"OH GOD!" he yelled as he pumped her full of his seed.

"That's it...cum for me baby...cum for me...YES...YES...YES!"

She continued to bounce on his lap until she felt his cock begin to soften. Chloe laid her head on his shoulder and relaxed as she caught her breath. The cushion of the couch was soaked with their combined juices and when Chloe stood up, another flood of cum hit the carpet. She kissed Tom softly on the lips then removed her dress from him and put it back on herself. After making some adjustments to it, she leaned down and kissed Tom again then disappeared into the bathroom. When she returned her hair was straightened and her make up was refreshed.

"Aren't you going to stay?" Tom asked with sad puppy dog eyes.

"No sweetie, I've got to get back to my friends. Thanks for a great time," she said taking one last look at his incredible body.

She blew him a kiss as she headed out the door.

***

Jeff and Kelly were on their fifth beer when Chloe returned. Tina made her way to their table to hear the details of her adventure and the results of their bet. Chloe relayed ever detail of her encounter with Tom and by the time she was finished everyone at the table was horny.

"What about the bet?" Kelly asked, "Who won?"

Chloe pulled the three envelopes from her clutch purse and opened them one at a time. After reading each prediction she made the announcement.

"Tina had me down for ten guys but she was a bit short. Kelly wrote thirteen and Jeff guessed twenty one. The total number of guys that hit on me at the bar was," she paused a couple seconds for effect, "nineteen so Kelly wins."

"You gave in too quickly," Jeff said a bit disappointed he lost.

"Ah, don't feel bad. You get me as a consolation prize," she replied with a devilish grin.

With that said, she took his hand and they headed back to the bungalow. When they got there, they climbed into the hot tub to relax. Jeff gave Chloe a foot massage that almost made her cum and she gave Jeff a foot job that did make him cum. Chloe got out of the hot tub to let Jeff recover and then stripped off her hose to take a shower. She got into bed and found Jeff there waiting for her. He cuddled up to her to go to sleep which was fine with her since after all the alcohol and events of the day, she needed some sleep. Her head was throbbing like she was already hung over and drifted off to sleep within a few minutes.

***

Chloe felt a hand on her shoulder shaking her but she didn't feel ready to get up yet. Her head felt funny and her body ached.

"Just a few more minutes," she said in a groggy voice.

She felt the shaking again and she heard a voice talking to her but she couldn't make out the words. What was Jeff trying to say to her?

"It's time to wake up," the voice said, but it didn't sound like Jeff.

Chloe's eyes fluttered open to see Tina standing over her shaking her awake. She was in a uniform that had a name tag on it.

"Ma'am, you need to wake up...We're about land," the Tina said.

"What? Where am I?" Chloe asked as she looked around her.

"Miami, Florida...We're on final approach. You need to bring your seat to the upright position and fasten your seat belt."

Chloe was confused. What was happening? She tried to make sense of the situation when Kelly walked by collecting trash and head phones. He was in a uniform too. He stopped to talk to Tina briefly who motioned toward Chloe before heading toward the back of the plane. Chloe realized she was sitting in the front row of the first class section of a large passenger jet. How did I get here?

"Are you alright ma'am? You've been tossing and turning in your sleep ever since we left Heathrow. A few of the passengers were concerned when they heard you cry out several times," Kelly said.

"Heathrow? I've been out all that time?"

"Yes ma'am. We weren't in the air ten minutes and you were out like a light."

It was then it all came rushing back to her. Chloe had taken a tranquilizer to calm her nerves. No, she had taken two because she didn't think the first one was working even though the doctor said they were strong. She was so nervous about taking this long fight but she had been given an all expense paid trip to a singles resort in the Caribbean by her boss. He said it was thanks for an outstanding job with the Trans Con account. He said she needed to relax. 'Wait a minute, someone else told me the same thing just recently' she thought, It was Jeff! He was on a trip like that...this! I must be going crazy.' Depression began to creep over her at the realization she had imagined the whole experience.

The plane soon landed and people bustled to collect their belongings and exit the plane. Chloe was still feeling down as she pulled her carry on bag from under the seat. It was then she saw the enormous wet spot on the seat cushion and felt her knee length skirt, realizing it and her nylons were soaked too. Fortunately her skirt was a dark color and wouldn't show much but she wrapped her jacket around her waist just in case. She was about to exit when the cabin door opened and the copilot and flight engineer emerged. It was Randy and Tom. They were part of the flight crew. Chloe remembered them when they boarded back in England. Then Jeff appeared next talking about a tropical vacation he was going on that very day. All there faces had materialized in her dream. She felt even more depressed.

"You lucky dog! Ten days and nights at a singles resort in the Caribbean...I'm so envious," Randy said as he left the plane followed by Tom.

"I'm a bit old for a place like that. I'm not sure what I'm going to do with all those twenty-something's running around. They're not going to be interested in me. I can't believe you guys bought that for me for my birthday," Jeff replied following his crew members out.