tagFirst TimeTropical Tutor Ch. 02

Tropical Tutor Ch. 02

bywriterjab©

Arriving at the beach a little after 8 a.m., John went over last minute checks on the boat he and Macy would sail in together. Teaching sailing lessons was second nature for the young man having grown up in a family that regularly sailed the Great Lakes. John knew his way around boats and easily got certified in his first couple days at the resort and soon he would share that experience with a woman who surpassed his wildest fantasies.

Rob, his supervisor, was there too to help him get the boat ready and "just make sure they got off without a hitch." John may have been a virgin when it came to sex, but he knew Rob was only there because he was at the volleyball game and saw John and Macy together later that afternoon.

"I don't know how you did it, newbie, but you may have just scored the finest pussy this resort will see all summer," said the tall, black Jamaican with blue eyes and pearly white teeth. Rob worked part-time at the resort at studied mathematics at the nearby University of the West Indies. "Since I am your supervisor when it comes to matters of this sailing rig, if there's something you can satisfy her with, just let me know I'd be glad to help."

John just laughed as he stowed the survival box that included a first aid kit, a flare gun, bottled water, high-energy food and some other accessories for the half-day outing. Because they would sail to a tiny uninhabited island the resort leased, they didn't need a lot of food since outfitters had already dropped off supplies to a well stocked cantina they would visit sometime around noon. Rob reminded him for the thousandth time that his cell phone would probably work if they got in trouble and to just wait until he arrived to "take over" he said with a booming laugh. John of course realized he was to some degree expendable, but a resort couldn't afford to lose a paying customer. The damage to its reputation could doom the resort in a very competitive industry.

Together they pushed the Rhodes 19 sailboat down to the water, just as Macy arrived a few minutes after 9 a.m.

"Hi boys, hope I'm not late," she said with a big smile on her face. Her blonde hair, which fell to the tops of her gorgeous 36DD breasts, flew freely in the light breeze. Those beautiful locks framed luminescent blue eyes and a very arousing smile. Both men took their time surveying this delectable piece of female flesh: 36DD-23-34. Of course a great rack, but then a tiny waist and just enough ass to dream of doing her doggy style. Well, at least Rob had that dream, John wasn't aware of that position ...

Yet.

She was "dressed," if you called it that, in one of her barely there thongs and a big white T-shirt. She said the T-shirt would keep her warm as it might be a little chilly out away from land, though the air temperature was near 75, only a few degrees from the overnight low of 70. It would later get up into the mid-80s, under an cloudless sky. Warm air and warm water promised a beautiful day of sailing. Rob greeted her, and a bit to John's annoyance seemed to linger in the hug he gave Macy a bit too long.

"Who's your sexy friend John? Too bad this is a private cruise," making no effort at all to conceal her interest in the tall black man.

To his credit Rob laughed, checked his watch then claimed he was late for a meeting. The things I do for this kid, he thought. Already his massive cock was nearly full erection just from the teasing Macy threw at it. With Rob gone, the two returned their attention to the boat. John inserted the rudder and soon they were skimming out into the brilliant greenish blue water. Macy told John she passed the sailing school there before, had her certification card, but just thought it would be best to go with a strong man who could control the boat better in case she got distracted.

"Besides, I may have to work on my tan at some point, and the last thing I want to do is pay attention to steering," she added. "But first, I'm a bit superstitious and don't want to see you lead this expedition without a kiss good luck."

She brazenly took the lead and leaning into him kissed that sexy mouth of his a second time. She even did a little exploration with her tongue giving John his first lesson on pleasing a woman.

When John finally made it back to reality, about a minute later, he pointed out some safety issues and reminded her to be careful when the boom swung as it could easily knock either of them into the water.

"If that happens, I'm going to have to insist you put on a life jacket," he said, hoping that wouldn't happen and obstruct his view of her body. But just now he was more interested in maneuvering for another kiss.

They made good time as the boat handled well. Gradually the sea darkened in color as they cruised out into deeper water, perhaps 35 feet deep. John told her they would head to a small uninhabited island the resort leased from the Jamaican government. The island had a small bar and grill where guests could buy lunch or dinner, but the rest of the island consisted of the romantic Caribbean beaches which drew tourists down here. Inland the shoreline rose up quickly to an extinct volcano with a couple waterfalls that spilled into refreshing pools of fresh water amid deep shade that offered a break from the brilliant white-sand beaches.

At one point, two dolphins kicked up from the depths and skimmed along beside the boat. But i's speed really wasn't impressive enough for the streamlined mammals and after tilting first one way then the other, the two males got a few looks at Macy then cruised off to find a sea turtle or something else to play with.

Although she liked sitting next to this sexy young man who was bare to the waist except for a gold chain around his strong neck, the last thing she wanted to do was sit around wasting time. There was way too much to teach this young man and if all went well, and she knew it would, there would be plenty of explosive orgasms for her. Since he was still rather timid, she decided it was time to get the seduction in gear. John had been rather particular about watching out for the boom and not getting swept over the side. So to avoid having to wear a life jacket, Holly did the next best thing and inquired about anything cold to drink. John said there was a cooler with some beer and a couple energy bars in case they have problems.

"Two beers coming right up," she said. Of course she knew he'd try to get up and insist he get the drinks, but standing before him she used his momentum to rise to upset her balance. One moment she was on the deck, the next she screamed (all for effect of course!) and fell overboard.

The ocean wasn't all that choppy so her life wasn't in danger. Still, John freaked. He moved quickly to the main mast, grabbed the life ring and after paying out enough line tossed the ring about five feet past her.

"Grab the rope, and I'll pull you in!" he yelled.

Macy splashed around a bit (more play acting on her part) then grasped the rope, followed by the ring that she clung too and let the strong young man pull her in. He got her around to the back and helped her aboard. Then, he dropped the mainsail and lowered the anchor. He was just turning around to ask her if she was OK when a sight confronted him that he wasn't expecting.

Macy's T-shirt was stuck to her body and now nearly transparent, it outlined her firm tits and erect nipples. John stood transfixed for a few moments as instant lust swept over him and he fell prey to her tantalizing treasures. Though he'd seen them the day before, the fact no one else was here added to his excitement. He wanted to go to her and ... and what? How?

"Oh, I'm so cold, I need to get out of this freezing shirt!" She bent over and struggled out of the soaked cotton and still pretended to shiver. John wrapped his arms around her and hugged her to his chest. "John, could you grab a towel so I can dry off?"

As he turned to get the towel, Macy slid the tiny thong down her legs so when he turned around she was naked. The effect was near instantaneous -- she could see his cock stiffen and poke the front of his shorts. Any other man who had been with a woman would have closed that gap in an instant, Macy realized with delight that John was too afraid of messing up to do anything.

For his part, this was the first time he'd gazed upon a woman's pussy, other than in a skin magazine or on the Internet. And, not just a pussy, but a freshly shaved and smooth one! Even if he didn't know what to do, his tongue did. It began to dance in his mouth in expectation of exploring that exotic grotto.

"John, your standing there doing nothing isn't helping me warm up, but another kiss might help," she instructed him. He fumbled a bit, and she giggled in response then sighed in satisfaction all to help set him at ease. She could feel her insides melt from the sweet feel of his lips on hers, she moaned into his mouth opening up to invite him in.

"MMMmmmm, Johnny thanks, you're so hot against my skin, mmmm, please hold me and make me feel good all over," she whispered to him as her tongue swept into his ear.

Being with a willing and seemingly pleased woman gave John a confidence he didn't previously possess. Gathering her face delicately into his two hands he tilted her head up and to where he wanted her. His tongue flowed gracefully inside her mouth and danced across her teeth and then poked her tongue gently. As he did so, it was as if a loud announcement went off in his head telling him he was about to have sex for the first time!

"OK Babe, there are other places you can kiss and nibble. like my jaw, my neck, ears and even over and around my eyes. Just know this, the more you warm a woman up, the hotter and wetter sex will be when you finally get inside her."

To a disciplined and determined mind like John's, this was a call to learn and practice everything her could to make Macy feel ecstatic.

She then poked her tongue along his jaw, landing light kisses that got him shivering when she located the nerve. Each little twinge sent a jolt through his system, and he sought out to deliver the same pleasure to her.

Macy then looked deep in John's lust-fueled eyes and then held his wrist pulling his hand downward. Two splendid mounds of flesh awaited the arrival and excitement his hand would deliver. She continued to stare into his eyes feeling her arousal build knowing the feel of his fingers on her tits would move them past just kissing to the beginnings of foreplay. One hand settled in place as her mouth opened up and she sucked in some air. But the pleasure was short-lived, a groan followed as his touch was a bit too hard and insistent.

"Easy John, there will be a time to pinch and bite, but for now go easy, like this. She gathered his hand up again in her own and showed him how to lightly rake his fingers over her nipples. Remember you're gradually warming me up, not sticking me in the microwave on high. That's how men get ready for sex, women take a bit longer."

With that he cupped and caressed her breasts, gently pulling on her nipples and rolling his fingers over the excited nubs. By this time he'd finished with her ears and was working down her neck: light kisses, blowing little puffs, light licks. A bit further and basic instinct kicked in as John's head, as if remembering what it was like for him as a baby, slid down between her pendulous breasts kissing and licking as his hands continued on her nipples. Then his mouth strayed to one side, found that nourishing bud and began to suck on it as if he would draw milk from her through effort alone.

No milk issued, but the resulting heat that coursed through her body stoked her desire. She was no longer just instructing, she was now a full on participant. As the boat gently rocked side to side, John moved between her two nipples adding bolts of pleasure that triggered her first orgasm.

"Oh fuck John, oh you got me so hot for you, MMMM! Oh, this boat is so fucking hot. It's motions almost feel like another lover holding me and rocking me to new heights. But then, that's not all that's fucking hot. She gazed into his eyes and purred, "Making out with a sexy young man who also listens well really turns me on!" Her sexually charged banter was in part fueled by the after-shocks of a wickedly good orgasm.

She then directed him to stand and be prepared to hold onto the mast for support. "John, your next lesson concerns learning to receive pleasure. This will help you know how to give and want to give pleasure in return. Just so you know, I am an expert cocksucker and my husband isn't the only man who thinks so, she boasted and giggled again. She loved the times she felt slutty and didn't mind letting others know how hot that made her.

She arranged their beach towels on the deck in front of him and got on her knees. Reaching up she unbuttoned his shorts and slid them down his well muscled legs, delighted to see that he was naked underneath and sporting a stiff erection whose one eye stared at her in expectation.

"I'm sure you know what oral sex is, has a girl ever sucked your cock before?" she inquired, knowing full well his answer would be he'd never been with a girl before. Macy just kind of knew, and finding out she wanted to do her best touchdown dance in celebration. Instead she kissed up the length of each leg from the knees up and then pressed her face into his crotch. John's hard 7-incher was trapped against his body and her face as her hands cupped his ass. She loved this most basic of masculine scents inhaling deeply his musk.

She then began caressing his cock and balls while rubbing the head all over her face. Her affect on him was immediate as his cock leaked a bit of pre-cum onto her cheek. Macy was quick to scoop it up on a finger and stick in her mouth, relishing the taste. Next her lips and tongue began to work over his shaft as she really got into making love to his cock.

Thankful that the mast was beside him, John hung on as he felt little shivers throughout his body. Although he knew what an orgasm was, in a clinical sense from health class, the actual experience was foreign to him. All he knew at this point was these shivers of delight intensified as Macy became more entranced in her technique, such as moving a hand to caress and squeeze his ass and using the other to encircle and stroke his thick shaft. The main event of cock sucking would start soon, and John knew it wouldn't be a long bout.

If a blowjob is this awesome, what could fucking feel like?

Macy made little mewling noises as her lips descended over his spongy helmet. This was one of her favorites parts of cocksucking when she first felt a man's prick enter her mouth and assault her senses with his scent and taste. She loved the thrill it gave her to feel his hard sausage move over and past her teeth as her pink tongue massaged the underside of his shaft. MMM, John's cock tasted yummy!!! Her head began to bob up and down as she took a bit more of his warm quivering meat into her mouth, lubing it up good she relaxed her throat and eased down his shaft vacuuming him in all the way until her lips were nestled in his pubic hair.

Feeling the sensations of her throat milking his cock, John felt his knees go weak as his level of arousal climbed quickly toward his first major eruption. Releasing the mast, his fingers gathered her sexy blonde locks and he soon realized he was pulling on her head shoving his stiff cock deeper into her throat.

Macy began to hum a tune as she continued to suck on and deep throat his cock. Reaching down between her legs she decided on a little extra excitement. Coating her index finger from her frothy pussy, she waited for the right moment. In an instant, John felt the gain in sensitivity like each individual nerve ending in his cock head was shouting for release. Macy sensed it too feeling his head grow wide in her mouth. Soon!! She said, soon I'm be bathed in sweet, gooey cum!

For the rest of his life, he'd desperately search for the exquisite sensations that rocked his body to its foundations. At this point, he didn't know how to hold back his orgasm, nor for that matter did he know if he could. But then Macy thrust her finger deep into John's ass and that move triggered a frenzied response. As the river of semen boiled up from his balls and surged up his shaft, his body tensed to deliver the full force of a gut and mind wrenching orgasm

"AHhhhhh, GAWD!! ... ooooo, I'm CUUUUUMMMMMmmmmmmmmiiiiiiiiinnnnnnnngggggg!"

Macy took the first blast in her mouth then pulled his shaft out as subsequent eruptions plastered her cheeks, nose and hair; then sliding his magnificent cock head back inside she set about milking all the creamy spunk from his love muscle. What a huge load that poor young man was holding onto! She didn't mind though as she continued to swallow his tasty cream, warming her stomach.

John's cock was doubly alive now as the nerves shrieked their joy in realizing their first orgasm. Amazing aftershocks causes his body to nearly jackknife in two. His legs became a mass of jelly and he crumpled to the deck, Macy still sucking his hot appendage.

WOW! Oh fuck, that was ... what was that, he thought. His mind, flooded with endorphins staggered like a drunken man. His gray matter attempting to process the momentary visit to heaven he just experienced. Contracting muscles in his groin continued to send twinges of delight racing out his cock head. That was fucking awesome, and he HAD to have some more!

Satisfied she milked all of his seed from his tasty cock, Macy finally allowed the still hard head to slide from her mouth. It trailed a string of semen and spit as if it didn't want to leave Macy's sexy mouth. She then crawled up his body to kiss him. Given her experience and absolute love of sucking cock, she held some of his cum in her mouth to share reveling in the wicked feeling it gave her to secretly pass John globs of his own semen.

That gift along with droplets of spunk on her face gave John his first taste of his own cum. To his surprise, he realized he not only liked it but he also enjoyed the slippery feel of the fluid. Macy didn't even need to coach him on cleaning up his mess as he licked up his seed, then, like a honey bee coated in pollen returns to its hive, he moved over her mouth kissing her and sharing his latest mouthful.

"You're a naughty boy John, feeding me your cum ... so naughty and so sexy," she said as she nestled into the muscles of his chest. For a while they lay together on the deck, naked bodies entwined for the first time as they laughed and talked a bit getting to know each other. He realized he really liked Macy, and it didn't seem to him as if they were that different in age. However, his attention span was flagging, not so much because he didn't enjoy her, but because basic physiology dominated his brain functions. Images flashed through his mind of his own facial contortions that arrived the first time he reached orgasm. Those images acted as the spark that ignited nerve impulses racing the body's central nervous system super highway to the brain. The master sex organ processed this data and routed an appropriate response: John's cock only slightly limp stiffened rapidly announcing it was ready to fuck.

"That was so fucking hot, I think I'm ready for the final exam -- can you show me where to put this big guy?" he said, hefting his stiff cock while staring at her with lustful eyes.

"I'd love to show you that John, but first, I know you care about pleasing the woman you're with, and I also know you wouldn't want to fuck her without first giving something in return for what she just gave you. So, how would you like to learn how to eat my pussy?"

"Eat pussy? ... he asked in a distracted tone that suggested his mind was still completely focused on thrusting his big dick into her tight cunt ... "Uh, yeah, I ... could do that ... I suppose."

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