A Holiday With Kelly Ch. 01

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Kelly helps resolve Rob's holiday dilemma.
5.3k words
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Part 2 of the 11 part series

Updated 06/10/2023
Created 07/03/2021
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"Oh, for fuck's sake!" Rob Sutherland exclaimed loudly into his mobile phone before pausing to listen to what was being said by the person at the other end of the call.

"Bugger it!" slamming it down on the table he continued to curse, "Shit, shit, fuck, shit!"

"Rob! Manners." His mother, Kelly, poked her head out from the kitchen, "What have I told you about your language in the house?"

"Sorry mum," he said somewhat sheepishly.

"Now what's all the fuss about?" she wiped her hands on a tea towel and looked at him questioningly, "Why all the bad language?"

"It's bloody Henry. He's only gone and broken his leg playing sodding rugby." Rob raised and lowered his arms, sighing in complete exasperation.

"Oh dear, that's not very good, is it?" his mother responded frowning, "What about your trip?"

Henry was Rob's best friend and they were due to head off to Spain in two weeks-time for their first grown up holiday, on their own. Ever since they had both turned 18 a few months earlier they had been planning their break and had intended spending their week-long vacation drinking and chasing girls.

Now, with Henry obviously out of action, Kelly wondered if her son's holiday would have to be cancelled.

Rob rolled his eyes in irritation, "Well he can't go can he. The doctor's say he can't fly and even if he could he'll be stuck in a wheelchair for weeks."

"So, there's definitely no way he can possibly go?" she enquired, already knowing the answer.

"Not a sodding chance." Her son shrugged.

"Well at least you'll get your money back from the insurance." Rob's mother put forward, adding quickly, "You did take out travel insurance, didn't you?"

"Yes mum. You know we did. You insisted. Remember?" he groaned inwardly at his mother's question, "Henry's calling them now and he'll let me know what we have to do."

"Good. At least you won't lose out financially." She turned and went back into the kitchen leaving her son to sit and wait for a call from his best friend.

It was nearly two hours later that Rob's phone rang and he snatched it up eager to hear what his friend had found out from the insurance company.

"Is that Henry?" Kelly stuck her head around the door only for her son to wave her into silence.

"You're fucking joking?" Rob raised his voice as Henry related his conversation, "That can't be right. Can it?"

Hearing him becoming agitated again Kelly came to stand in the living room next to him, wiping her hands on her jeans she watched her son carefully, obviously wanting an update on the situation.

Rob listened as Henry continued talking, shaking his head angrily and trying not to interrupt but eventually failing, "Surely they can't do that can they? That's hardly fair."

"What's up?" his mother mouthed silently to him, getting nothing more than a shake of his head in response.

"OK text me the details and I'll call them." Rob ended the conversation and put the phone down.

"Well?" his mother asked, brushing her shoulder length blonde hair back from her face.

"It's not good." he frowned, "Basically it appears that Henry can get his money back but I can't."

Giving him a look of astonishment, Kelly expressed her surprise, "What? How does that work then?"

Patiently he re-counted exactly what his friend had told him.

Henry could get a full refund as his broken leg would prohibit him from travelling but as Rob wasn't a direct relative and could still travel, he wasn't eligible. Apparently, his only two options, other than losing his money, were to go by himself or to pay an administration fee and swap Henry's booking to another person.

"That's the answer then." She said breezily, "Ask around all your friends. I'm sure you can get one of them to go with you."

"Yeah right." he answered sounding a lot more positive than he actually felt.

"Good, that's it, you're all sorted out then." His mother declared as she headed back to the kitchen, adding quickly, "Dinner will be ready in about half an hour."

It was just the two of them, there was no one else for them to wait for as Kelly had been by herself ever since before her son had been born. Rob had never met his waste-of-space father. Apparently, the low-life had just vanished into the night as soon as he found out that he had gotten his eighteen-year-old girl-friend pregnant.

Kelly being the stubborn sort of person she was had refused to have a termination or to have her baby adopted and had set out to bring Rob up by herself.

Now, eighteen years later, all his friends teased him about having a hot 36-year-old MILF for a mum. Not that he minded too much. Secretly he had to admit she did look pretty good and most people who didn't know Kelly took her for mid to late twenties rather than mid-thirties. At 5' 4" tall with shoulder length platinum blonde hair, vivid blue eyes and a slightly upturned nose she was undoubtedly extremely pretty.

Although she only had small breasts, they seemed perfect on her slender 34B-23-34 figure. Exercising regularly, she kept herself toned and fit, and with a nice pair of legs to compliment her shape she could always turn heads.

"Dinner's ready." A shout from the kitchen stirred Rob out of his quiet musings.

"Any thoughts on what you're going to do yet?" Kelly asked her son as they were eating.

He shook his head, "Not really mum. I'll text a few people later but I doubt any of them will be able to make it."

She laughed softly, "Don't be so pessimistic honey. Something's bound to turn up."

"Yeah, maybe you're right." He responded gloomily and turned his attention back to his food.

After dinner was over instead of helping with the washing up as he usually did, Rob settled down on the sofa with his mobile phone to send some texts and make a few calls.

"Any luck?" Kelly asked about forty minutes later when she came into the living room having finished doing the dishes and putting everything away.

"No. Nothing yet." he groaned despondently, "It's as I suspected everyone is either busy or they don't have the money."

"Surely there's someone who could make it? What about James? Is he around?" she suggested.

Rob shook his head, "Nope. He's just bought a car and spent all his money on that."

Kelly thought for a moment, "Or that nice lad at college. What's his name... Chris or something?"

"He's already going away with his girlfriend in two weeks' time." he told her despondently.

She considered his answers, "And there's no one else?"

Rob didn't respond immediately, just stared at the floor as if he wanted to say something but wasn't sure.

"Well?" his mother asked, "Is there anyone else?"

"Clair Simpson could go." He told her quietly.

"What!" Kelly almost exploded, "You asked Clair, the cheating bitch from hell, Simpson?"

"Err... well no... not exactly. She heard about it from Chris' girlfriend and she called me." He didn't dare look at his mother as he spoke.

"I hope you told her where to go."

He stared disconsolately at the living room carpet, "Umm... well... err... not exactly, no."

"There's no way I'm letting you go on holiday with that little tart. Not after the way she treated you." Kelly told him angrily, "You can do so much better than that little scrubber."

"At least it would be someone to go with." Rob stated quietly.

"Rob, you know she'd dump you as soon as you got there. That fucking whore would be off screwing half the resort on the first night."

Rob knew his mother was basically right. He had been dating Clair for a while when he had found out that she had been sleeping around behind his back. It wasn't that he had minded her fucking other guys but he had really been broken up by the fact she had lied to him.

When Kelly had found out about it, she had been furious and had confronted Clair, threatening to claw her eyes out and rip her tits off if she ever came near her son again.

"Yeah, I know but what else can I do?"

Sitting next to him on the sofa she looked at Rob for a moment obviously considering saying something.

"Look I know it's a bit off the wall but I could come with you. If you want that is?" she finally suggested.

Taken by completely by surprise it took Rob a few seconds to respond, "It's all pretty simple you know mum. We just booked a basic twin room in a fairly cheap hotel. It's not a fancy place."

"Does it have a pool" was the only question she asked.

"Yeah, but it's a twin room mum. We'd be in a room together. Doesn't that bother you?"

She laughed, "Of course not silly, I've seen you in your shorts to many times as it is."

"I... err... I'm not sure... you know..." he stammered trying to think about his mother's proposal.

"Well, you certainly aren't going with Clair Simpson."

"No, I guess that wouldn't be such a good idea." He, almost reluctantly, acceded to her.

"So?" she looked at him and grinned, "Shall I go pack a bag?"

He grinned back sheepishly, "OK."

And that was it, the matter was settled. Rob was going to go on his first grown-up adult holiday with his mother!

The next couple of weeks flew by in a flurry of activity as they prepared for their trip.

First, they had to change all the booking details, which set them back the £50 administration fee and proved to be a lot more complicated than the agent made it seem. Especially when they tried to get their new tickets printed.

Of course, Kelly also had to go shopping for new clothes and insisted her son accompany her. Following his mother round a procession of clothes shops and being asked to comment on a variety of different outfits was embarrassing enough for an eighteen-year-old. However, when his mother wanted to try on two miniscule bikini's Rob was completely shocked by his own reaction.

Kelly had picked a red two-piece and a rather daring leopard print bikini she liked. Disappearing into the changing cubicle she left her son waiting outside while she slipped into the first of the swimsuits.

"What do you think?"

Rob turned around at the sound of his mother's voice and stood staring at the scantily clad figure in front of him. The animal print bikini was little more than three triangles of material and several bits of string, revealing a lot more than it covered.

"I... err... its... umm... really... err... nice mum." Rob stammered, his cock immediately starting to swell in his jeans at the sight of his mother's uncovered flesh.

He had glimpsed his mother in her underwear around the house on more than one occasion but this was somewhat different. Here she was blatantly presenting herself for his approval.

"You sure? It's not to revealing, is it?" Kelly did a twirl showing most of her tight arse to her son.

"N... n... no, no its... err... fine." He blushed crimson and sat down quickly to hide his erection.

"Great. I'll just try on the other one and then we're done." She went back to change as Rob sat and waited.

"Hey Rob, what're you doing here?"

He turned around and his heart sank as he saw Danny Williams and Tom Anderson, two of his friends from college, walking towards him across the store.

"I bet he's checking out tall he babes in the changing room." Danny laughed.

"Err... no well...I... err... umm." Rob tried to think of a believable answer.

"What about this one?"

They all looked up as Rob's mother stepped out of the changing cubicle in the skimpy red two-piece suit.

"Oh, hi boys." She smiled.

'Fuck.' he thought to himself as she paraded up and down in front of the three lads in a bikini that revealed more than it covered.

"What do you think? Do you all like it?" she did another twirl in front of the three of them.

"Yeah, yeah it looks absolutely fabulous." His two friends chorused enthusiastically.

"Fucking hell." Danny swore as Kelly went back to change out of the costume, "Your mum is a fucking babe."

"To right." Tom added with a smirk, "I'd bloody well give her one."

"Hey, that's my mum you're talking about." Rob tried to sound annoyed by their comments but in reality, he found the idea of one of his friend's screwing his mother a real turn on.

Slightly embarrassed the two youngsters apologised to him and made a hasty exit leaving Rob to contemplate how he had felt about the things they had said.

"Oh! Have they gone?" Kelly asked as she came out of the changing room and looked around.

Her son smiled, "Yeah. They had to... err... be somewhere."

Half-an-hour later, after she had paid for the two swimming costumes, they started to make their way home loaded down with shopping bags. Kelly happily chatting away while Rob still struggled with his reaction to seeing his mother in her bikini's and how the comments his friends had made had turned him on.

That night as he lay in bed Rob stroked his hard cock and thought back over the afternoon to how incredibly sexy his mother had looked when she had paraded half naked in front of him. The things his two friends had said about her also sprang to mind as he found himself starting to fantasise.

Imagining her laying spreadeagled and completely naked as one of his friends slammed his hard shaft into her, he began to pump his hand along his aching length.

'Oh fuck, mum." He thought to himself as he felt his cum bubbling up from his balls.

"Aaahhh... aaahhhh... yes." He groaned quietly as he came, not wanting his mother to hear, his semen arcing upwards and splattering across his belly and chest.

Feeling incredibly guilty he cleaned himself up and settled down to sleep, his incestuous fantasy still playing out in his mind as he gradually drifted off.

When Rob had told his friends exactly who he was going on holiday with he was met with either laughter or envy. Some of them found the idea of him going away with his mother highly amusing while others, especially Henry, were genuinely envious and told him they wished they could swap places with him. He laughed along with them but underneath he still found his reaction to seeing his mother in her bikini rather more than confusing.

Packing, the day before they travelled, was almost as much of a trauma for Rob as the shopping trip, his mother continually asking for his opinion of what she should take, even down to her underwear. It was all he could do to hide an almost permanent erection and not to blush profusely every five minutes.

Despite his concerns over sharing a room with his mother he was actually grateful, when the morning of departure arrived, that he wasn't going alone.

The two of them took an early taxi to Gatwick airport where after a relatively speedy check-in and a rather slower encounter with the security gate they made it through to the departure lounge.

"Tea, coffee or something stronger?" Kelly asked her son as they went in to the bar area.

"What are you having?"

"Coffee, I think. It's a bit to early for alcohol." she decided.

"OK get one for me as well then. I'll go find us a seat" Rob replied.

Dropping into a chair he watched as his mother wiggled up to the counter. The tight denim shorts she had on clung to her rear like a second skin and emphasised her legs, while the tight top hugged the contours of her modest breasts closely.

He had to admit looking at her, that his friends were right, she was fucking gorgeous.

"Where are you off to then darlin?"

Waiting at the bar to be served Kelly turned around hearing a voice beside her.

A young guy, not a lot older than her son was standing beside her and smiling, "So where are you going?"

"Spain. How about you?"

"Portugal but I'm think of changing it to Spain now." He winked at her, his gaze travelling up and down her body.

She giggled and touched his arm, "Spain's a big place."

He laughed, "Don't worry about that gorgeous I'd find you anywhere."

Just then the server came to take her order and her attention was drawn back to the bar.

"I'm Paul." He offered his name after she had placed her order.

"Kelly."

"You know you really remind me of someone Kelly." He put an arm around her waist and pulled her towards him and his friends.

"Oh who?" she was curious now.

"Say hi to Kelly guys, who does she remind you of?" Keeping his arm around her waist he turned her to face his three companions.

Paul's friends all crowded around.

"Fucking hell, she's a dead spit for that Mandy Monroe." One of them blurted out with the other two quickly agreeing.

"Who the hell is Mandy Monroe? I've never heard of her." Kelly enquired her curiosity roused.

Paul grinned, "Look her up when you get a minute. Only I'd do it in private if I were you."

Just then her two coffees arrived ending the conversation.

"So, can I get your number? Maybe we can go out for a drink when we're back?" Paul asked as she went to leave.

"Thanks, but I don't think so." Kelly declined with a smile.

Rob had sat and watched the interchange at the bar with a growing feeling of jealousy that he found hard to explain. In fact, when the guy had slid an arm about his mother's waist, he had almost got up to intervene.

"What was all that about?" he insisted almost angrily when Kelly returned.

She laughed, "It was nothing sweetheart."

Pressing her to explain Rob persisted, "Well, it didn't seem like nothing to me."

Kelly sighed and, somewhat reluctantly, related what had happened at the bar.

"You didn't give him your number, did you?" he demanded to know when his mother finished.

"No. I didn't." she laughed, "But maybe you can tell me who Mandy Monroe is?"

Rob blushed at her question and brusquely told her it was no one she needed to worry about.

Finishing their coffee, the pair of them made their way through the crowded departure lounge and boarded the plane for the short flight to the island of Majorca.

Arriving at Palma airport at just after 11 in the morning the two of them queued for ages for passport control and then quickly collected their bags before taking the short coach transfer to their hotel.

The two-star Sol Dorado hotel was exactly as Rob had described to his mother. Small and clean, with a bar and restaurant attached, it had the swimming pool that Kelly wanted at the rear of the main building.

They were the only people to be dropped off there so checking in at reception was quickly completed before they made their way up to their room on the fifth floor.

Opening the door Kelly looked around with a sense of dismay.

When her son had described their accommodation as small, he hadn't exaggerated. The room was tiny, there was barely room for the two single beds and the dresser let alone the two adults who were supposed to stay there. The balcony boasted a little additional space with a table and 2 chairs while the minute bathroom was obviously not going to be suitable to double as a changing area.

"We're not going to get much privacy in here, are we?" Kelly stated the obvious to her son.

"Errmm... no... not really." Rob answered, sitting on his bed wondering what he had let himself in for.

Sighing she turned her attention to storing her clothes in the dresser leaving her son to put away his own things.

"I think I'm gonna head down to the pool. You coming?" she asked him as she finished unpacking her bag, dropping her red bikini on her bed.

"Maybe in a second." Rob replied, not wanting to think about getting changed in front of his mother.

Kelly bit her bottom lip, "Look honey we're going to end up seeing a lot of each other this week so I suggest we just get it over and done with before it becomes an issue."

"Oh... err... yeah... umm... I guess so." he still didn't move, keeping his back to her.

Shrugging Kelly began to undress behind her son, slipping off her top and jeans before removing her underwear, depositing her bra and panties on the bed with her other clothes.

"If you want to look you can. I really don't mind. You're going to see me nude at some point this week." She told him, standing naked by her bed with her hands on her hips.

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