Tropical Vacation Ch. 01

Chloe was noticed by all on the small commuter flight. To say she stood out was an understatement. Most of the passengers were twenty-something's dressed in t-shirts, shorts and flip-flops. Not Chloe. She was wearing a thin white silk top, mid-thigh length black skirt, black 4" high heel sandals but what caught most peoples eyes were the glossy caramel colored semi-sheer hose encasing her curvy legs. Chloe noticed both men and some of the women whispering and nodding in her direction. Some even giggled or shook their heads in disbelief. She was beginning to have second thoughts about her wardrobe choice until she saw an older man three rows back in the isle seat giving her lustful approval with his eyes. Maybe this won't be such a bad vacation after all, she thought to herself as she sat down in her seat and prepared for take off. Chloe was in the first row on the isle opposite of her admirer. She took the opportunity to cross her sexy legs so that her foot was just visible to her 'new friend'.

*****

At first Jeff thought this is going to be fun, taking the boss up on his offer of an all expenses paid vacation to a tropical singles resort called Fantasies, but as he watched the plane fill up with young single people about half his age, he began feeling mighty old. It was his boss's way of thanking him for his twenty plus years of service to the company and the incredible effort he made in completing a multi-million dollar project under budget for a new and very big customer. Now Jeff was thinking it was going to be a long ten days, and then he saw her. Dark shoulder length brown hair, sexy curvy body on a tiny frame and an outfit that set his cock to stirring in his pants. She was even wearing pantyhose. Things were looking up, he thought as he watched her firm calf and dainty foot bouncing when she crossed her legs, after taking her seat.

*****

The flight to the island was less than an hour and when they landed in the late afternoon, about half the people on the flight climbed aboard an air conditioned shuttle sent by the resort. Jeff sat across from Chloe and admired the view of her sexy hose covered legs through his dark sunglasses so she wouldn't notice him staring. The seats on the shuttle faced each other making it easy for him to do this. She kept her legs together at first then slowly crossed them. He was sure he could hear the delicate swish of nylon as her thighs moved even though there were multiple conversations going on all around him and the noise level was high. He even thought he saw that she wasn't wearing any panties but he couldn't be sure. The bulge in his pants was becoming more noticeable, so Jeff placed his day pack in his lap to cover that fact. When he looked back over at Chloe he saw a smile on her face. He final got up the courage to introduce himself.

He leaned forward and said, "Looks like we're going to be the chaperones on this trip."

"I'm starting to believe that myself," Chloe replied with a laugh, her distinct British accent making him smile as well.

"My name is Jeff," he said holding out his hand.

"Chloe," she responded taking his hand. Her tiny manicured hand seemed to be engulfed by his large paw.

"Are you here on business or pleasure?" he asked.

"Pleasure hopefully...why do you ask?"

"Well you look like you're dressed...I mean...you aren't dressed like a typical tourist," Jeff said looking to either side of her.

"Something wrong with the way I'm dressed?" she said looking down at her outfit.

"No...Not at all. You look amazing!"

"Ahh...Thank you. Some of the people on the plane were giving me some strange looks. I felt like I had a clown suit on."

The shuttle came to a stop and every body stood to disembark. Jeff managed to keep his pack in front of him, concealing his rigid cock. Even with her four inch heels, Jeff towered over her. At 5'-3" in her stocking feet Jeff was nearly a foot taller than her at 6'-1". As they exited the shuttle a young and beautiful dark skinned woman introduced herself as Kate the guest relations coordinator and began directing people to their rooms and handing out maps of the resort grounds. Jeff wanted to see Chloe again and needed to act fast before she was gone.

He leaned down and asked her, "Do you want to meet for a drink later?"

"Sure, how about the lounge by the pool in about two hours?" she said, looking up from the map, "I need to freshen up."

"Great...I'll see ya then."

*****

Jeff walked into the lounge and was surprised to see it virtually empty. He had changed from his t-shirt and jeans into tan cotton pants, a floral pattern button down shirt and casual deck shoes. Most of the guests he saw were in or around the large pool outside. He took a seat near one of the windows looking out onto the patio area where there were a few die hard 'sun worshippers' still soaking up the last rays of the day. Many of them were topless and one or two even bottomless. Jeff smiled as he enjoyed the view.

"Nice scenery," a man's voice said, "It's the best seat in the house."

"You can say that again," Jeff replied to the bartender who had caught him staring at ladies outside.

"What can I get you to drink, Sir?"

"Morgan's and coke...and don't call me Sir...I feel old enough already. I'm Jeff," he said extending his hand to the man behind the bar.

"The name's Randy and I know what you mean," he said shaking Jeff's hand. Randy was the oldest member of the resort staff Jeff had seen so far. He was 38 and was about ten years older than his nearest coworker. At 42, Jeff was still his senior by four years. Randy placed Jeff's drink on the bar in front of him and the two men chatted for several minutes.

"So Randy, why are you working here?"

"Can't you see," he said motioning to the window, "Its paradise."

"No offense, but you seem a bit old for working at a place like this."

"None taken. I manage all the bars at Fantasies. One of my guys called in sick so here I am," he said holding his arms wide.

"Well that makes sense."

Leaning in Randy lowered his voice.

"Just between the two of us, I still get lots of pussy working here."

They both laughed and continued to chat for the better part of an hour. Randy had worked at the resort for six years and knew all of the good place to see the 'best' sights, and promised to point them out to Jeff at a later time. He was a serious voyeur and had admitted to masturbating while watching several prior guests during their sexual encounters. Jeff couldn't help but chuckle at this and even envy Randy for the access he had. After a couple of drinks, he admitted to Randy of his pantyhose fetish and told him about the woman he met on the plane ride to the resort. Randy had a bit of a hose fetish himself and would take trips back to the 'main land' just to see women in nylons again because most didn't wear them at the resort.

Their discussion was cut short as the distinct sound of a woman's legs in pantyhose walking toward them made it to their ears, punctuated with the clicking of heels on a hard wood floor. Chloe's short strides made her appear to be moving in slow motion toward the two men who were watching her every move. She had changed out of her silk blouse and into a light weight cotton sleeveless sun dress and nude pantyhose. Jeff's cock surged to life once again at the sight of her gorgeous legs in those silky shimmering hose. He stood and pulled out a bar stool for Chloe.

"Thank you...you're such a gentleman," she said with a giggle.

She waited until Jeff was about to sit down before crossing her legs. She did it deliberately slow to get his reaction. He nearly fell out of his chair when he caught a glimpse of her pussy through the sheer material. What she didn't expect was for Randy to get the same view and have nearly the same reaction. She smiled at their awe struck expressions, knowing she had them both under her spell.

Jeff snapped out of his momentary paralysis and offered to buy Chloe a drink.

"All the drinks are complimentary remember...'All inclusive,' that's why you paid the big bucks?" Randy reminded him, then turned to Chloe and asked, "What'll you have?"

"How about something tropical," she replied.

"I've got just the thing," Randy said as he busied himself making her drink.

Jeff caught himself staring at Chloe's luscious legs in those glossy hose and realized he wasn't going to be able to hide the erection tenting the front of his pants. When he looked up, he saw that Chloe had noticed his problem as well.

"Is that for me," she asked in a coy voice.

"Yes...see what you do to me," he replied sheepishly.

"Its alright...I'm flattered," Chloe assured him, running her hand over his thigh.

"Here you go...one Mai Tai," Randy announced setting the hollowed out pineapple, filled with his concoction in front of her.

"Oh my, that looks wonderful," she said beaming Randy a smile.

"What are you two doing tonight?" Randy asked.

Jeff and Chloe were caught off guard by his innocent question. They looked at each other in an awkward moment of silence.

"We hadn't made any plans past having a drink together," Jeff finally responded.

"You should go to the Luau on the beach tonight. Its always fun and they have some good entertainment. They start seating at 7pm," Randy suggested.

"That sounds nice...Will you accompany me, Ma Lady?" Jeff asked in his best British accent.

"I would be honored Sir," she replied.

All three laughed and Jeff raised his glass to Chloe who touched her pineapple to his. They had about an hour to kill before heading to the Luau so the pair stayed at the bar chatting with Randy. Their conversations drifted all over and included sexual topics as well. They all seemed very comfortable divulging their personal secrets. Maybe it was the alcohol or just the kind of place they were in but all three were very turned on by the time Jeff and Chloe had to leave for the Luau.

"When do you get off?" Jeff asked Randy.

"At nine...why?"

"We'll meet you back here for drinks," Jeff replied.

"Employees aren't allowed to drink with guests at the resort bars," he said.

"How about you meet us at Jeff's room later for drinks?" Chloe suggested.

Jeff and Randy looked at each other then to Chloe.

She smiled and said, "That's not against the rules is it?"

Jeff and Randy looked at each other again, and then both men nodded.

"I'll see you two around 9:30...What's your room number?"

"I'm in B23," Jeff replied.

"You're in a bungalow, very nice. There is a full bar in there, so I can make some outstanding drinks for us," Randy said.

"We'll see you at 9:30 then," Jeff said as he took Chloe's hand and headed for the door.

"Bye," Chloe waved to Randy with a seductive smile.

The Luau was fun for Chloe since she had never been to one before. All the exotic foods and entertainment allowed her to relax and enjoy the company of her new friend. Jeff enjoyed the entertainment too, with the topless dancers shaking what they got, but both Jeff and Chloe were anxious to get back to his bungalow and see what would happen next. The two had got to know each other during dinner and that had stirred the fire between them with more sexually charged conversation about their mutual love of pantyhose. They walked down the path toward the beach and Jeff's bungalow when they were met by Randy jogging up behind them.

"I brought some champaign," Randy said holding the expensive bottle up.

"Did you loot the resort stash?" Jeff asked.

"No, this one is all mine. I bought it for a special occasion and this seems like as good a time as ever to open it."

"Great...Well here we are," Jeff announced as he opened the door to his bungalow, "Ladies first." Motioning Chloe in, he tossed the keys on the table by the door, Randy following closely behind.

"Wow...this is really nice," Chloe said admiring the lavish and spacious interior, as she walked through the main room and past the kitchen, ending up on the patio over looking the beach. "You have a hot tub too? This is really really nice!"

"Make yourselves at home," Jeff said as he went into the bedroom.

Randy opened the champaign and poured three glasses, handing one to Chloe and one to Jeff when he returned. He picked up his glass and said, "To new friends." The others raised their glasses and repeated his words.

After a sip of champaign the trio sat on the patio around a small fire ring, drinking and talking and laughing until the bottle was empty. Chloe stood up with a bit of a difficulty and said, "Let's go in the hot tub."

The two men watched as Chloe ran her hand in the water, feeling its temperature.

"I'll make us some more drinks," Randy said, heading for the bar.

"You boys go ahead and hop in and I will join you after I use the little girl's room."

Both men grabbed their drinks and one for Chloe and set them on the hot tub. Jeff turned on the jets and bubbles and began to get undressed. Randy followed suit and they climbed in the warm water and sat down just as Chloe reappeared on the patio. She was carrying three towels and was wearing one of the robes from the bedroom. Jeff and Randy stared as she set down the towels and turned towards her two man audience. Jeff could hear that she still had her heels on as she walked up to the side of the above ground pool. He watched as she became shorter when she stepped out of them but he wasn't prepared for what happened next. Chloe shrugged off the robe, letting it fall to the ground at her feet. Her full 36C breast stood proud on her chest; the nipples hard and erect. She climbed the two steps at the side of the hot tub and sat on the edge with her feet in the water. She was still wearing her silky nude hose.

"Do you like my bathing suit?" she asked the two stunned men.

All they could do was nod in their current state. Chloe settled down on the seat opposite both men. The tub itself was relatively small, holding four people at most. She leaned back, picked up her glass from the side of the hot tub and took a deep drink. She set it back down and looked across at her two playmates. Chloe smiled and ran a hose covered foot up each man's leg until she reached their erect cocks. Jeff and Randy groaned in unison as she rubbed up and down their rigid shafts. Jeff's hand caressed her calf while Randy closed his eyes and savored the sensations he was receiving.

Chloe's pussy was getting very wet from the anticipation of this moment. Now it was absolutely drenched and tingling. Her left hand found her throbbing clit and massaged it through the thin velvety material of her nylons. Her other hand cupped her right breast, pinching the nipple between her fingers. The water made the hose feel like they had become part of her, clinging like she had never felt before. The sensation was intoxicating. Chloe felt Jeff move close to her right side, holding her leg in his hands and gliding his fingers up and down its length. Leaning close, he kissed her shoulder, working his way to her neck.

"Mmmmmmmmm," she moaned drifting on a cloud of increasing pleasure.

Her hand left her breast and encircled Jeff's stiff cock as he pressed his lips to hers. Chloe squeezed his cock at the base then stroked it gently up and down. They kissed softly at first but the intensity increased as their tongues wrestled and her hand moved faster. Chloe felt Randy's hands guiding her foot up and down his erect member. She opened her eyes and looked at him as he used her foot to masturbate himself. He was intently watching her and Jeff as they kissed and fondled each other. Jeff's right hand moved over Chloe's between her legs. She allowed him to take over the petting of her pussy and returned to fondling her boobs with her free hand. Jeff's middle finger pushed the cotton panel of Chloe's hose into the smoldering folds of her womanhood.

"Oh ya baby...right there...mmmmmmm," she groaned as his digit worked deeper into her moist cleft.

She increased the speed of her strokes on Jeff's throbbing cock as well as the pressure on Randy's shaft. Jeff took Chloe's right nipple into his mouth and sucked it while flicking his tongue over the sensitive nub.

"OH God! Yes...Yes!" Chloe cried arching her body.

The orgasm hit her hard and she shuddered from the intense sensations. She rode the waves of pleasure coursing through her, completely lost in the moment. When her breathing returned to normal she smiled at both men then resumed her pleasuring of them.

"I need to cool off...I'll just watch you two for a while," Randy said, standing up and sitting on the side of the hot tub; his back against one of the support posts on the patio. His hard cock stood tall as he began to stroke it.

"I don't think so," Chloe remarked and quickly moved between his open legs. She placed her arms on his thighs and took over slowly stroking his cock with her hand. "I'm not done with you yet," she said, taking his cock into her mouth.

"Aaahhhhhhhh," he groaned as Chloe bobbed slowly up and down on his dick.

She released his cock from her mouth long enough to say to Jeff, "I didn't tell you to stop rubbing my pussy did I?"

"No...sorry," Jeff said moving behind her.

She spread her knees wide to give him better access then went back to sucking Randy's raging hard on. Jeff's hand glided over her slippery crotch panel a few times eliciting soft purrs from her, then he pulled down on it and pushed a finger through the delicate material. He widened the hole he had just made, exposing Chloe's entire pussy to his touch. His finger tip moved over her swollen clit and made slow circles on the sensitive bud. Her hips started to thrust back and forth in time with his movements. Jeff's finger slide back along her slick pussy lips until it was at the opening of her love canal. Turning his hand over, palm down, he could feel Chloe's pussy contracting and relaxing as his middle finger sank inside her. She pushed back hard against his hand, trying to get more of him in her. He placed his thumb against her erect clit and pressed his finger down, as if trying to rub the two together with Chloe's clit and the wall of her pussy between them.

"Mmmmm... mmmm...mmmm," she grunted, still sucking Randy's cock with a vengeance. Her hips bounced up and down violently as her second orgasm took hold of her. "Aaaahhh yes...yes...that feels wonderful... Uuuhhh...aaahhh," she cried, leaving Randy's cock unattended momentarily, then returning to her furious oral assault.

When her hips stopped bucking and the clenching of her vaginal muscles subsided, Jeff removed his finger from her oozing hole. He knelt behind her, placing the head of his pre-cum soaked cock at the opening his finger had just vacated. The tip slid in with little resistance due to the enormous amount of natural lubrication Chloe was producing. Jeff eased into her slowly, allowing her to adjust to his invading member. He could feel her tighten up on him, clamping down hard on his cock.

"Mmmmmmm," he moaned, feeling her incredible grip.

He pressed his hips firmly against Chloe's wonderful round hose covered ass and began shifting side to side. His cock brushed back and forth inside her hot tight pussy. He pulled out all but the head then thrust back in. Chloe grunted with the impact then moaned in pleasure. Jeff repeated this again and again, building speed as he went. Soon his hips were slamming into her sending water splashing in all directions.

Randy was in heaven. It was more than just a fantasy come true. He had always dreamed of getting a blow job while clandestinely watching a couple having sex, but now he was there with them getting a blow job from the woman while watching them both fuck. It was too much for him. He felt his balls tighten as the first load of cum erupted from his cock and into Chloe's mouth. It caught her by surprise and she released him from her lips, as the following spurts covered her chin, neck and chest with hot sticky cum. She kept stroking his cock until the last drops ran down his shaft and over her hand.