Isabella's Holiday

It was Sarah's fault. Isabella had been telling her friend about her holiday plans over salad and sandwiches and Sarah's off the cuff remark about a holiday romance had got Isabella thinking. Perhaps yearning would be more accurate.

It had been 5 months since she had broken up with her last boyfriend, a cute but ineffective man. She struggled to remember what he looked like now. She was so busy with work, family commitments and a busy social life she didn't think much about it, but Sarah's comments as they had lunch one dreary London day in late winter definitely got Isabella thinking.

Ten days, and 5 timezones later, Scott was sitting at the beach bar of the hotel, just after sundown when Isabella entered.

At 22 Isabella, was working in finance living in the bustling heart of London, she had an air of elegance and grace that was as captivating as it was subtle. She was tall and slim, her figure is a testament to her Romanian heritage, a legacy of her parents who immigrated to the UK to work at a UK university, Isabella loved her heritage but was fully assimilated to life in the UK. Her long, lustrous brunette hair cascaded down her back. Isabella's small breasts complement her slender frame, enhancing her natural grace and poise. Despite her striking appearance and sharp intellect, Isabella often found herself grappling with self-consciousness. Her height and keen mind, while assets in the corporate world, sometimes leave her feeling like she intimidates those around her. This internal struggle added a layer of vulnerability to her otherwise confident demeanour.

Scott was here for a friend's wedding and was currently single, his previous girlfriend having given up on their 2 year relationship as going nowhere and moved out 3 months ago. Scott had barely noticed. He was a successful consultant at the Boston branch of a big consultancy, and affluent. He had played football (the American style) in college and now in his early forties was still athletic, clean shaven and square jawed, he kept weight off by visiting the gym, ratchet ball and sensible eating, the slight grey of his hair around the temples hidden by periodic dyeing.

In all Scott was handsome, had an easy charm, and the confidence which comes from plenty of cash. Scott had little difficulty in keeping his bed warm with women in their 20's, to the point of having something of a reputation for nailing the interns at the firm.

In Barbados on that warm evening Isabella came into the bar with her friend Rachel. Isabella wore a light strapless white dress, with a simple gold necklace which highlighted her now sun kissed skin bronzed from her normal pale alabaster. She was slightly above average height and slender she had on low heeled deck shoes.

The two girls settled at a table overlooking the tropical sea and ordered drinks. The warm Caribbean breeze carried the scent of salt rum and coconut as they stepped into the beachside bar. Steel drums played softly in the background, and fairy lights twinkled overhead.

Scott noted the two women when they entered but knew it was pointless to talk to them now as they were deep in conversation, it was too early in the evening anyway, so he went back to watching the sport on the bar's oversized television.

Rachel scanned the room with bright eyes "Oh my god, Isabella, look at this place! It's perfect. And did you see that gorgeous bartender? Those arms..." She fanned herself dramatically.

Isabella adjusted her sundress nervously "Rach, we literally just walked in. Can we at least order drinks first?"

"That's exactly what I'm doing" Rachel said as a waiter approached, "Two piña coladas, please!" She flashed him a brilliant smile at the bartender "Make them strong - we're celebrating our freedom!"

After he had taken the order Isabella said "I thought we agreed on daiquiris..."

Rachel whispered not taking her eyes from the room "Trust me, piña coladas are more photogenic. Plus, look - there's a whole group of guys over there playing pool. That tall one with the curly hair keeps looking over here."

Isabella glanced briefly, then looking away "He's probably wondering why you're staring at him like that."

Rachel laughed "That's called making eye contact, babe. You should try it sometime. We're in paradise! When else are we going to have cocktails with mysterious strangers on a tropical island?"

Just then the drinks came and the waiter dashed off to a group who were demanding attention. Isabella took a slip of her drink "When else are we going to have cocktails just the two of us without any complications? Remember why we came here, Rach."

Rachel took a long sip "Mmm, this is incredible. And yes, I remember - to forget about boring jobs and boring ex-boyfriends. But who says we can't have a little fun while we're forgetting?"

Isabella felt conflicted, Rachel brought out the stuffy elder sister in her. But the thought of some fun made her heart beat a little faster. She reluctantly smiled "Your idea of 'a little fun' usually involves me being a wingwoman while you disappear with some guy named Chad or Tyler."

Rachel put her arm around Isabella "Hey, no Chads or Tylers here. Only gorgeous Caribbean men with accents that could melt chocolate. Come on, live a little! We're only here for a week."

Isabella sighed but her smile widening "Fine. But if I end up having to navigate back to the hotel alone because you've run off with Mr. Curly Hair, I'll order the most expensive room service breakfast and charge it to your card."

Rachel grinned "Deal. But something tells me you won't be alone long either. That guy by the bar hasn't stopped stealing glances at you since we sat down." She nodded towards Scott.

Isabella blushed and looked "What guy by the window? Don't point!"

Rachel grinned mischievously "Oh, this is going to be a very interesting week..."

Isabella's mind tuned over Rachel's comments about the man with the curly hair, a local man, black skinned, exotic.

An hour or so later and Scott was still in the bar, the opportunity came, Rachel had been chatted up by a handsome Canadian, she had left Isabella for the bathroom and to get some drinks and Isabella was sitting alone, Scott took the opportunity to go up and talk to her, he might have preferred the other young woman, but he had been beaten to it, it seemed.

He was experienced enough to not attempt a chat up line. Just an introduction would suffice. She looked up and Scott flashed a perfect smile. "Hi, I'm Scott".

Isabella welcomed the distraction, she had noticed him earlier and found him attractive so she chatted with Scott.

Rachel was taking her time, girls night was alright but she was definitely interested in a holiday romance. The conversation between Scott and Isabella got more flirty. Both felt there was chemistry there, Scott made her laugh a little despite the fact that his humour was a bit rough, but Isabella was in the mood to be entertained. She had a thing for older men, and Scott looked fit. For Scott, Isabella was young, pretty and he even liked her English accent. Eventually Scott suggested they dance and they got up, Scott took Isabella's hand and led her to the dancefloor.

Rachel had been dancing with a Canadian man called Reid, she had drunk a lot more than Isabella and felt in urgent need of physical intimacy. She had made an excuse and moved away so she could seduce her man out of sight of her friend. By the time she returned, she could see Isabella with some other man kissing passionately at the side of the dancefloor. Her hands were stroking his hair. Rachel smiled, relieved she did not have to feel guilty about ditching her friend and sent Isabella a message saying she would see her tomorrow, and with that she left with Reid.

Sometime later Isabella checked her phone, and she was pleased that Rachel had left. She smiled and thought she would probably be experiencing some of the fantasy she had mentioned to Isabella drunkenly the night before. She slipped the phone away before turning to find Scott behind her.

"My friend had to go" she explained away Rachel's absence.

Scott smiled "Time for another drink, Mei Tai for you?" he asked.

Isabella smiled back, her face flushed "You'll get me drunk" she said giggling slightly, she felt drunk, but still in control. Happy and relaxed anticipating being seduced by this older man.

"That wouldn't be the worse thing" Scott said smoothly, taking her by the arm and guiding her to the bar, where he pressed up close to her.

They had their drinks and danced some more, eventually ending in the cool night air outside the club. They kissed in the shadows, Isabella was ready and wanted him, and she happily accepted a suggestion from Scott that they go back to the hotel.

As they stood in the lift Isabella felt Scott's hand on her buttocks. Isabella didn't move and let him explore. Her heart fluttered, and she unconsciously bit her lip.

When the lift door opened she took his hand and led him down the corridor to her room. She took out her key card as Scott's arm slide around her midriff. She giggled as the lock clicked and turned around, Scott kissed her and teasingly she walked back into the darkened room. Scott smiled and followed.

They stood in the entrance as the door closed, kissing, touching and caressing. Scott still tasted of the fruity cocktails they had been drinking, his hands were all over her body, gripping her firmly, lifting her white dress to caress the soft firm skin of her buttocks.

Eventually Isabella stopped. "Excuse me one moment" Isabella said, she left Scott to go to the bathroom, switching on the light which illuminated the room for a brief moment before the door swung shut.

Scott got a rough idea on the layout of the room and navigated across to the bed, before he switched on the small reading light by the big double bed. He took the opportunity to check the nightstand. As he hoped he found Isabella's toy, a bright pink rabbit vibrator. He quietly closed the draw. He quickly undressed, neatly folding his clothes and placing them on the armchair.

Isabella used the toilet, washed and checked herself in the mirror. It had been a few months since she split from her last boyfriend and she was extremely aroused, and feeling quite frisky, she wanted to feel the weight of a man on top of her, feel him inside her. On a whim she hurriedly brushed her teeth before returning to the bedroom.

Scott stood looking out of the window across the moonlit sea. The reading lights by the bed were on and semi illuminated his naked body and firm muscular buttocks, despite the half light there was an obvious contrast between his tanned ankles and torso and the skin which had been protected by shorts was lilly white. He turned as Isabella approached, he had a good body with just a little gut, evidence of too many skipped sessions at his exclusive racket ball club. His penis already semi erect, Isabella smiled.

"Hi" he said as she came closer, he took her in his arms and they kissed, Scott's excitement pressing against Isabella.

He pulled down the back of Isabella's dress, and by squeezing the clasp of her strapless bra, unhooked it one handed. The first attempt failed but he got it on the second attempt.

He pulled back from their embrace and pulled down her dress, a small pressure and it was over her breasts and crumpled to the floor, exposing her slim naked body. Isabella's nipples were already erect.

Taking control he pushed her onto the bed, and climbed on top of her, his erection grazing the inside of her legs. The contact was erotic and Isabella responded by opening her legs further welcoming him.

Scott gripped both her wrists, pressing them down on the mattress above her head, with his free hand he reached to the bed-side table, opened it and took out the vibrator. He looped his index finger into the handle and used his thumb to switch it on. It buzzed excitedly.

Still holding her arms firmly, Scott ran the vibrating toy down Isabella's body, looped around her nipples on both breasts and then slowly, to build anticipation, traced its head down her midriff to her crotch. Isabella watched him do this, enjoying it but willing him to go faster. She panted a little as the toy touched her sensitive nipples, which became even more erect.

Isabella was enjoying the sensation of being held down and she gasped and moaned as the tip of the toy touched her eager clitoris. She could feel how wet her vagina had become. She closed her eyes and pouted her lips. Scott kissed her as he pressed the toy along her vulva.

Eventually Scott angled the vibrator to enter Isabella, he looked down at her, Isabella's face and chest were flushed, her eyes closed. Scott still had her pinned to the bed, her hands above her head, like she had surrendered, she gently strained against him, enjoying the sensation of being trapped. She gasped as the vibrating head of the rabbit toy entered her.

Isabella felt a soft, velvety sensation as the rabbit vibrator was gently inserted into her vagina. The smooth firm silicone tip glided effortlessly into her well lubricated vagina, its smooth surface contrasting with the gentle hum that began to build. She mewed softly as it was fully inserted, the vibrations intensified, sending waves of pleasure through her body. The feeling was uniquely intimate, the gentle curves and soft texture of the vibrator creating a sensation that was both playful and deeply satisfying. She sighed deeply as the second head of the toy pressed against her clitoris. Instinctively Isabella closed her legs around the vibrating shaft.

Isabella was close to a climax when Scott withdrew the toy, he was aroused by making Isabella aroused but wanted to be inside her now.

Without a word Scott stood up, and fetched his trousers. He took out a condom and used his teeth to open it. Isabella lay in the bed, frustrated by the delay. "Hurry up" she thought. She watched him, the contrast between his lower body pale in comparison to his tanned torso was faintly comical; she felt the tension inside her and wanted release.

Scott placed the condom on the tip of his penis and rolled it down along his shaft, grinning he climbed on the bed, his erection hanging between his legs. He threw the covers off Isabella who giggled. She opened her arms and Scott embraced her, gliding his penis towards her vagina. He rubbed it repeatedly along her clitoris until Isabella, eager now, took it gently in her hand and guided it into her. She breathed out as he thrust into her. She looked up at Scott but he had his eyes closed, in reality he was picturing his colleague at work.

Having been deeply aroused by playing with Isabella, he quickly built into a fast rhythm, within a couple of minutes Scott was almost thrashing thrashing about as he approached his climax, Isabella tried to catch up but couldn't, Scott grunted as he came, and stopped thrusting. He looked down at Isabella and she smiled back. Scott rolled off her. "That was... you were amazing" he declared breathlessly.

Isabella cuddled up next to him, content with this intimacy if not a little disappointed. She felt the need to climax, but could not find a way to ask for it.

Scott was spent and fell quickly asleep. Isabella remained awake for a time she contemplated masturbating but would find it too embarrassing if he woke up. So she decided to see if he would like sex again in the morning.

The following morning Isabella woke late, she opened her eyes and stared at the ceiling before turning to her side, the bed was empty, a depression in the pillow and the faintest smell of him was left behind but Scott had left. She sighed in frustration, thought for a few minutes and got up to check if he really had gone and having found he had, took a long shower..

A little later that morning Freddy was waiting on the tourists on the sun loungers strung along the beach. Each pair of loungers was placed under a thatched sun shade and the guests would plant a flag in the sand when they wanted to order.

Freddy noted a flag at the other end of the beach, and keen for tips jogged over. At 18 Freddy was fit, and toned. Today he wore shorts and a tight t-shirt which accentuated his thickset muscular upper body. He had a thick fuzzy beard and he wore his long hair in braids. He enjoyed working at the resort, the pay was not great, but he could use the staff gym, he had friends there and periodically he would catch the attention of a guest and the management turned a blind eye to this. It was far better than his native Ghana.

He had left as a child to get to America but had instead ended up in Barbados working as the resort.

As he approached the guest he noted the slim tall body of the guest in a pale blue bikini, he enjoyed the sight.

Isabella looked up, as she heard the waiter approaching, "Hi, can I order some iced water with lemon please" she said.

"Sure miss", Freddy said with a smile, keeping it formal, which he had learned was optimal for tips, "anything else?"

"Not for the moment," Isabella said. Freddy jogged off to get the order and was back shortly. He found Isabella moving the heavy wooden sun lounger. "Let me do that for you Miss" he offered.

Freddy put the iced glass down on the table and moved the sun lounger with practiced ease. "Thanks" Isabella said simply. As he spread Isabella's towel on the cushion, she noticed his sexy body.

Having spent an unsatisfying night with the Scott, she still felt aroused and the hot young black man in front of her was causing her erotic thoughts, "what is wrong with me" she thought to herself. She had never been with a black man before, but there was something about this man, he was so different, exotic.

Freddy noticed the look she gave him, he smiled a brilliant smile at her, he recognised that look.

Isabella took a sip of the icy, lemony water while enjoying watching him. It was ready and she lay down on the lounger on her front, she felt his eyes on her. "Anything else Miss" Freddy asked, as she reached into her bag to take out some sun lotion. Isabella shook her head, somewhat regretfully.

"You want me to get your back?" he asked. İt was still early and there were not too many tourists to wait on, he could spare minutes.

Isabella was surprised, "yes thanks", she said and thought she would enjoy his touch for a bit.

"Sure miss" Freddy said grinning even more broadly, the beach was fairly quiet this time of the day so he had time.

Isabella took the bottle of sun cream and gave it to Freddy and lay down on her front, her head turned towards Freddy. "I'm Isabella" she said,

"Nice to meet you Isabella, I am Freddy" he squirted a lot of the liquid onto his hands and started on Isabella's shoulders. Rather than just rub it on, he massaged it into her skin, using both his powerful fingers and his knuckles which pressed forcefully into her unresisting muscles. He pressed firmly, pressing hard on the way up and lightly back down, it felt great and she murmured in appreciation.

Without asking permission from Isabella Freddy undid the back of her Bikini top and worked his way down her back. Isabella was surprised but content to let this happen, Freddy's hands felt good and this was just a fantasy, she did not imagine it would go any further.

Freddy used both hands to massage Isabella's side, working up from her waist to her armpit, his finger tips reaching underneath her, it felt great and instinctively she lifted her body slightly so he could go deeper.

Freddy swapped sides so he could do Isabella's other side, his fingers just caressing the sides of her breasts, adding to the excitement Isabella was feeling. Freddy had done this a number of times before and knew that he needed to go slowly for the moment, let the arousal build in the girl, let that overcome any inhibitions they might have. His fingers gently ran down the length of Isabella's back which felt great.

Freddy's fingers went down to Isabella's buttocks, her small pale blue bikini only covered half of them. Freddy found them firm, with not a gram of fat on them, he massaged her muscles around the bikini, when she sighed deeply he knew he could go further, he started to put his weight down on her buttocks pressing her vulva against her towel ever so subtly turning her on more. Her arousal grew, her face and chest flushed as her pulse quickened.

Lying face down, eyes closed she imagined Freddy naked, his braids playing on her naked body. His dark body next to her pale naked body, dominating her.

Next Freddy started to edge his fingers to underneath the bikini bottoms, and massaged all of her buttocks. Still no resistance to his touch, Freddy thought, "I can go further", his fingers went deeper between her buttocks.

Freddy slid his thumbs down the inside of Isabella's thigh and without thinking she opened her legs wider to give him more access. Her inner leg was one of Isabella's most erogenous zones and this had her really turned on. Freddy's touch now was perfect, gentle but firm and Isabella's heart rate raced as he carried on stroking her on the back and inside of her legs. She could feel herself getting wet, her juices soaking the thin strip of bikini. Freddy could smell her sexual juices and it excited him. Inside his shorts his erection grew.

Freddy moved his hands now down to her ankles and Isabella was disappointed, she was really enjoying him touching her erogenous areas and while her ankles and feet felt nice it was not the same.

The beach manager wondered where Freddy was, he stepped out and looked up the rows of sun loungers and saw him with a guest. He smiled, "Lucky bastard" he muttered and went about his business, this was a perk of the job, as far as he was concerned and Freddy was a good worker. Maybe one day he would get lucky, away from his fat wife and 3 ravenous children.

After her ankle and feet, slowly Freddy's hand moved back up her leg. Each time his fingers reached a little higher, until they grazed the bikini which covered her vagina. The touch was electric, and Isabella shuddered. Freddy knew a critical boundary had been breached, without any resistance from this girl. Freddy carried on rubbing her inner thigh while the sides of his thick index finger rubbing along the bikini. Isabella could not contain it and mewed quietly but sensuously.

This was all the encouragement Freddy needed and with one hand he moved Isabella's left leg up bending her knee so she naturally tilted to one side and moved the thin strip of the Bikini bottom aside and he started to play with Isabella's clitoris, using two thick fingers to spread the lips of the labia so he could apply pressure to her clitoris, already his fingers were coated in Isabella's copious juices.

Isabella closed her eyes, and let him do this, the thrill of what was happening to her making her heart race, she could feel herself getting even wetter as the thick fingers played with her. She gripped the towel as an almost unbearable tension grew from her loins, her muscles becoming ridged. She pictured this man inside her and it tripped her over the edge, she tried to stifle the groans as she orgasmed.

To be continued