tagTranssexuals & CrossdressersT-Girl Fantasy Island Pt. 02

T-Girl Fantasy Island Pt. 02

byskywriter62©

Once again I am back, dear readers! I really appreciate the votes for my first part of this story. The encouragement really goes a long way. The comments both here and in my email have been wonderful and I really am amazed that people have enjoyed my stories this much! I only hope that I can improve more with each story so criticism is honestly desired and will not be ignored. Many of you here have decades more experience than I could ever hope to achieve and many stories here are works of art. Thanks to all of you honestly. As I have said before, I would be absolutely thrilled to know that some of you saved my stories to your private collections. If you decide to post them elsewhere please let me know and as always give an author (Even a beginner and very amateur one like me) the credit they are due for their work and imagination.

Lastly, I do want to thank RUWild, VicJohnson, Whiskeyisgood, Sugarandsalt and many other really talented writers for giving me the inspiration to come up with my own deviant scenarios, haha. You folks are the real artists here!


*****

T-Girl Fantasy Island Part II

By the time Isabella finished showering with her servant Adam, it was past 9 am. There was much to do as she ran the towel over her magnificent body. Adam stood behind her toweling her back and shapely ass. His own ass was still leaking cum from the energetic pounding he received at her hands in the shower. She smiled with pleasure as she felt his tongue probe between her ass cheeks.

"No.. No.." she objected. "It is already late in the morning already and there is too much to do to while away today on simple pleasures."

Adam looked disappointed but stood up to finish drying her shoulders.

As the beautiful brunette walked out of the steamy bathroom she paused at the door, "But you make it to my bed say.. around 11:00 tonight, you can take up where you left off, sweet boy." She winked and with a gentle pat on his cheek, vanished into her room to dress.

Adam made a mental note to himself all day to be sure to be on time tonight.

Isabella was deep into hunter registration paperwork when Patricia finally appeared at her desk in the expansive resort office.

"About time you decided to get some work done."

"Hmmm" murmured Patricia absent mindedly as she shuffled papers while mentally she replayed the moment when Keiko let her know she wanted to have her children. At her mid-40s, Patricia had to acknowledge she wasn't getting any younger. The sexy eighteen year old maid had been in her bed more nights than ever before. Maybe it was time to settle down.

A wad of paper bounced off her head as an irritated voice yelled,"Hey!"

She looked up startled at her partner's angry gaze. "Get one of your heads out from between that hot Asian's thighs long enough to finish the candidate list today, will ya? Preferably whichever head is thinking clearly at the moment if you please."

"Screw you," Patricia responded monotone.

"You'd never have better if I let you," replied a confident Isabella. "Besides I'd choose a firm young man's ass over your old flabby one any day. So I'd never be faithful."

Isabella shuffled through the hunters one more time. The current registration showed slightly more than 50 hunters this year. She passed that detail to her partner who was responsible for recruiting as many prey candidates. Fewer prey than hunters meant that someone was definitely going home without a prize which was not good. Isabella loved knowing all her clients had a new toy to enjoy upon leaving her paradise.

"Candidates are at slightly more than 100." Replied Patricia as she paged through file after file."After interviews, maybe we can expect 60 to 70 accepted and approved." She paused at a attractive young couple smiling for the camera. She noted they were confirmed. Taking in the shape of the husband and wife got her cock stirring under the desk. 'if only those damn rules didn't keep her from the hunt,' she thought ruefully and not for the first time.

Elliana Cordoba, an incredibly sexy woman in her late twenties from Brazil, sauntered into the office. She was responsible for everything from additional waiters and waitresses, supplemental cleaning staff, additional cooks, additional IT and grounds maintenance personnel to additional guards as they were required. She handled their pay, housing, uniforms and health care while they were on the island.

"Support is all online and ready, Senoras," she announced in her sexy heavy South American accent.

Isabella thanked the efficient young lady as that part of the production had even more difficulties than the hunters and prey. So many details to arrange and coordinate that it baffled her how this sweet young girl managed it all. At that moment Serena's cell buzzed and she answered with a cheerful, sexy "Hola?" A quick transaction in Spanish resulted in her putting her cell away with a smile.

"I have to pick up our star IT technician from the airport. With his new algorithms, we should have camera coverage throughout the hunt field without the data backlog and lag like we had last year. This kid is barely 18 and already graduated from MIT!" she finished with obvious admiration.

"Go get him, gal," replied Isabella not even looking up from the file containing twin hunter applications of Sherri and Carrie Anderson. These two hunters had enormous 44EE busts and extremely round figures. Yet still had cute baby girl faces that would surely drive any man crazy., at least until they unveiled their twin ten inch cocks. She definitely would approve these two. Their hunt should prove entertaining.

Elliana quickly changed out of her office clothes and into an incredibly short pair of cutoff jeans. Throwing her bra across the room in her hast, she flipped a loose tank top t-shirt over her shoulders and with a flip of long brown hair, she was out the door.

The resort had just the vehicle for picking up single VIPs and the fact that she loved the car made it her first choice for a ride to the small airport on the other side of the island. The gloss black 1958 BMW 507 Sportster growled to life at the first turn of the key. Elliana backed the feisty little car out of the garage and with a grin, spit gravel as she sped off down the road. The nimble car darted into the tunnel of vegetation surrounding the tiny island road as she picked up speed, rejoicing in the sweep of warm tropical air on her face and tugging at her hair.

Behind her dark sunglasses, Elliana saw more than a shadowy jungle road, she saw the freckled faced, red haired teenage boy that she was about to pick up from the airport. She found him in a video on YouTube, the Ryan McKetrick had entered MIT at the age of 15 and graduated at 18!

Elliana knew because she counted down the days to his eighteenth birthday! Something about that fiery red hair and pale skin made the brilliant young man seem so vulnerable and got her heart racing.

They had met through email, then chatting in messenger then cammed on Skype. She offered him a summer job at the island for their annual hunt event. Not being sure of his orientations, she left some details out concerning the island resort and the hunt.

The sleek black car slid to a stop in the airport parking lot exactly 30 minutes before Elliana took a moment to slip into the bathroom to check her hair and apply coconut scented (and flavored) oil across her cleavage and arms. Adjusting her shirt and glistening up her legs and exposed lower spheres of her shapely ass, she grinned at here reflection. Poor Ryan never stood a chance.

She slid her sunglasses back into place and watched as the charter plane touched down on the runway. A small group of passengers deplaned onto the hot tarmac when she spotted the thin young man as he stepped out into the sun. His hair caught the light and a thick lock flipped by the hot breeze across his eyes.

She quickly walked out to the crowd, past several gawking men and a few envious women straight to her prize. Wrapping the young teenager up in her arms, her firm breasts pillowed against his chest.

"Hola," she said breathlessly in his ear.

Ryan's face immediately went red as he stammered through what could only loosely count as English.

He had led a sheltered life back home, most of his social interactions where at school, with books, or at seminars. He certainly was not prepared for the latina goddess that had him in a surprisingly strong embrace.

She took off her sunglasses to allow him to gaze timidly into her eyes. Already she felt dominance over the young man. He was maybe only an inch or two below her height so she mentally reminded herself that at dinner tonight she would wear her favorite 3 inch stiletto heels to give even more of a physical advantage over him.

Ryan clearly had no experience with girls and Elliana continued to hold the weight of their greeting. She spoke excitedly of his accomplishments while they collected the few suitcases he brought with him. They got to the convertible that once again overwhelmed the speechless teenager, especially as he saw the rest of his fellow passengers cramming into a white drab van for their ride to the resort. Elliana placed his cases in the small trunk space and jumped in behind the broad steering wheel.

Ryan took his seat in the squat sporty vehicle and let out a yelp in surprise that got a playful chuckle from the bronze beauty driving. Whether the burst of speed from the car or the aggressive driving of the older woman beside him had him clamping a hand onto the door and a hand on the dashboard while even his ass cheeks were trying to grasp the seat cushion beneath him was anyone's guess but he remained in a ridged state for the first mile down the road.

Elliana continued to talk to him while she drove the long way back to the resort. She congratulated him on his recent eighteenth birthday and promised him a small celebration just between them later that got him squirming in his seat.

Try as he might, Ryan's eyes were continually drawn to her impressive cleavage. He did take a moment to admire the sleek brown legs that expertly pumped the accelerator and clutch and seemed to ignore the brake pedal more than he would prefer.

After several minutes of enjoyable conversation, with Elliana doing the majority of the talking, they pulled up to a secluded bend in the road that had a tiny dirt road branching off into the trees.Elliana guided the small car down the road and across an brief open field to a clump of palms situated at the center of a jutting cliff that over looked the harbor below.

The car glided to a stop and Elliana killed the engine.

"This is my favorite spot on the island, Ryan" she said softly, "I have been waiting for months to enjoy this place with you, my dearest friend."

Ryan's face went red yet again as he stared loose jawed at the beautiful girl next to him. Inwardly he was cursing himself because, as always, the smooth words he heard from the guys in the movies were not coming to mind. He stumbled embarrassingly over the few words he could come up.

Elliana ate it all up as she jumped out of the car and walked through the freshly mown grass around the trees. Reaching into the slim storage space behind her seat, she pulled out a soft thin blanket. She held out her hand to the shy technician who took it speechless at what he hoped would happen. He didn't see her wicked grin as she led them into the shade of the grove.

The scent of grass, sea salt and tropical vegetation wafted over the couple as she spread the blanket out under the slanting trunk of a large palm. The view of the sunlit beach below them was breathtaking. The sounds of the surf roared creating the perfect mood for what the sexy Brazilian had in mind.

Taking a seat on the blanket she looked up expectantly at the nervous young man. He quickly responded to her commanding gaze by dropping to his knees next to her.

"I love this place," she said softly as she put an arm around the nervous teenager's thin shoulders. "I am really glad you accepted the job! You are the best! I know you will do great but I wanted you here for more personal reasons than that."

Her brown eyes fixed on his green as his face seemed to try to match the same shade of red as his hair.

"I..I'm sure you can have your choice of guys around here a.. as beautiful as you are, Elliana!" He stuttered, kicking himself mentally for how he sounded exactly like the awkward, inexperienced kid that he was.

"Awww!" Elliana stroke the helpless boy with her sexiest smile. "A compliment!"

Pulling Ryan into another surprisingly strong hug, She breathed into his ear, "I was starting to wonder if you liked me at all, Papi."

Ryan shivered in her embrace. He felt more and more like the helpless girl in this clearly romantic scene than the powerful male that he was supposed to be. The jarring reversal of their roles made him even more vulnerable to Elliana's advances.

Slim brown fingers traced his face down to his chin as she guided his mouth to her own. So lost in the sensation of her smooth lips gliding over his own, her soft tongue slipping boldly between his yielding lips he didn't even pause to realize that this was his first kiss ever.

She pulled him down to the blanket and onto his back. Sliding on top of him she quickly used her arms and legs to trap the teenager below her. Their kisses deepened as poor Ryan was completely at the dominant Latina's mercy.She nibbled her way over his smooth cheek and along his jaw to his ear. So stunned at the aggressive attack of his new friend, Ryan remained flat on his back, his arms limp at his sides. Her soft dark hair spilled around their faces as she used her talented tongue to explore his ear.

Ryan was panting loudly from the thrills she was giving him and the warm exciting weight of her body. The press of those amazing tits against his chest and the smooth flesh of her legs rubbing seductively against his own, Ryan was completely oblivious to the growing press of her cock through her tight jean shorts and against his own throbbing shaft.

Elliana pulled the young man up from his emotionally drunken state and practically tore the shirt from his body. His tennis shoes flipped through the air to land one thud after another into the grass around the blanket. She claimed another kiss and again sent her tongue into the helpless boy's mouth as she quickly pulled the khaki shorts he was wearing down his pale legs.

"Oh Papi!" she exclaimed as Ryan tried to cover his small hard cock in embarrassment. "It's so cute!"

Ryan tried to will his body through the blanket and deep into the ground beneath them in shame. "I.. I know it's not much.." He stuttered.

"No No!" Elliana smiled to his surprise. "It's perfect. I won't have any trouble taking you like this!" With that, she dove down on his cock and engulfed it with her mouth in a single gulp.

Ryan's hips nearly launched off the blanket both in surprise of the sudden move and the exquisite pleasure her soft warm mouth and agile tongue were providing him. Arms gave out and the helpless boy fell on to his back gasping for breath. He had always dreamed of a blowjob from a beautiful girl but this was way beyond any of his wildest most erotic imaginations.

Through half lidded eyes he stared up into the swaying branches that shielded them from the late afternoon sun as the hungry woman on top of him devoured his cock. Her nails running up and down his thighs and flat stomach sent delightful patches of goosebumps across his skin.

She let the rock hard four inch cock of her now subdued lover slip from her lips as she left him panting on the blanket. As she returned from the car, he saw her taking a dark brown bottle out of her bag. She poured oil into her palm and warmed it in her hands before applying it to his pale flesh.

"I can't let my Papi burn in this sun." She said in that soft thickly accented voice of hers. The strong scent of coconut filled his head as her hands messaged the oil into his chest and stomach. His body bare under her caresses, her still being clothed further demonstrated who was in charge of what would take place on that blanket.

She took Ryan's small hard cock in her oil slicked hands and stroked it while leaning down for another soul weakening kiss. Ryan writhed in helpless ecstasy under the tanned woman's aggressive manipulations. His need for release made his head swim and his inhibitions begin to fade. Sensing the young man was close, the girl gently pushed the poor boy onto his belly. Oil soaked hands worked their magic on the back of his neck and across his shoulders.

The coconut scented oil relaxed Ryan's senses even more as he surrender himself to the pleasures of his goddess's powerful hands. Elliana luxuriated in the soft flesh of the pale redhead under her as she worked her way down to that sexy exposed bottom. Ryan groggily raised his head as she ran her hands over his smooth soft ass cheeks. Fingers slid wickedly down into the valley searching their way into his helpless body.

Ryan's head dropped as Elliana worked her oil slicked fingers across that crinkled star orifice that she was certain never experienced anything like what she planned for the weakened young man in her clutches. He moaned softly as she rubbed oil into that sensitive smooth ring of muscle. She felt him tighten at the first strokes but as she worked her magic on his flesh, that wonderfully tight flower began to bloom.

Gently she worked her finger into the young man's exposed bottom. Without even considering the implications, Ryan opened his thighs to allow the dominant woman more access to his ass.

Elliana smiled at how easy it was to lure her virgin prize into her web, her cock threatened to rip through her jean shorts, straining to get to the boy on the blanket. Watching the steady rise and fall of the teenager's chest, Elliana worked another finger, slightly surprised at how easy he had loosened up under her attentions.

Ryan gasped at the widening intrusion but never opened his eyes nor even had the strength to raise his head.

Elliana knew she could have the boy here and now if she wanted but she desired complete dominance over the young man and she wanted his full awareness of her authority as she would take him. Pulling the swooning male onto his bottom, the sexy goddess stepped away and pulled her tank top over her head. Dark brown tresses cascaded down her smooth tan body almost hiding two perfect globes of flesh. Her nipples were rock hard and ready for lips and teeth she would demand from her conquered prey soon.

"Close your eyes, Papi," she whispered above the soft breeze that cooled their bodies.

Ryan complied with his tanned idol's command and his eyes drooped shut.

Elliana slid her cut offs down her oil slicked legs and daintily stepped out. She used the tip of her foot to flip the discarded cloth off the blanket. Her rock hard cock shot out from her hips as she walked up to the helpless prize waiting for her.

With her cock inches from his slack lips, she softly commanded "Ok Papi, open them and see what I have for you to enjoy."

Ryan's eyes open sleepily and crossed at the enormous head swaying before him. The image was slow to register in the overwhelmed technician's mind as he slurred out a yelp in surprise.

"You..You're.. You're a.. a.."

"Yes, Papi," Elliana smiled down at him "It's all yours, all you have to do is surrender and accept it."

She seductively sat down in front of the stunned boy. Her cock stood straight and proud from her soft round hips. Again it was obvious to both of them, the roles that they would play that afternoon on that blanket hidden away from the world by the sway of palm trees.

She watched the vacant stare of the young man as she slid her legs down either side of his now kneeling body. Her cock weaved and swayed before his eyes. Still drunk with desire she had stirred within him so far, Ryan was past the point of considering that he was about to do. Seemingly unaware of his actions, Ryan went to his stomach, propped up on to locked elbows. His eyes never left the weaving hypnotic snake inches from his face. With a trembling hand that seemed detached from his body and his will, Ryan reached out and took that warm rod of flesh into his weak and submitting grasp.

Report Story

byskywriter62© 13 comments/ 30513 views/ 40 favorites

Share the love

Report a Bug

Next
2 Pages:12

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar:

   Cancel