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Thrown In At The Deep End

The pool boy and the M.I.L.F.

Copyright 2017 Charlie Wish


This story contains some sexual references.

Chapter 1

One last job to do today and my favourite of the whole week Tom thought. Not only because it’s always the last one of the week but because of who it is. Mrs. Fairbanks. In the many months Tom had been cleaning her pool he had always enjoyed his visit there. She was always very nice to him but also Tom thought she was a very fit looking lady. He didn’t really have any idea of how old she was but she had three kids the eldest being ten which he supposed would make her a MILF.

Whilst Tom rather fancied her he also thought that she was probably the same age as his Mum and that was just too weird to think about. He already had enough issues with the opposite sex going on right now with his girlfriend Carrie. She had been getting way too clingy for his liking and been making hints at marriage, at 22 there is no way he wanted to settle down having way too many plans starting off with seeing some of the world.

Whilst he had been pondering on these thoughts he had just been sitting in the drivers seat of the works van staring out the front window and out across the street at the other large posh houses in the neighbourhood. Houses that Tom, who lived with his single parent Mum, could only dream about living in. With his Mum’s limited income from working in a run down greasy spoon cafe and his money from part time work as a pool cleaner, it would take them a year to save enough for a months rent on a place like these.

He snapped out of his daydreaming as he knew he had just 15 minutes to get to Mrs. Fairbanks all the way on the other side of town which was at least a good 30 minute drive if the traffic was very light. He never could work out why his firm never considered travel time between jobs or even bother to try and work a reasonable route. Oh no, he had to cross town three or four times on occasions.

Without a single cloud in the sky Tom pulled out of the customers gravel drive and headed towards the centre of the town, reasoning that straight through the middle might be just a little quicker than trying to skirt around the outside. Well if he was lucky. He wasn’t.

45 minutes later he pulled into the Fairbanks’s drive a full 30 minutes late, again. Their house was the largest in the neighbourhood, not a mansion by any stretch of the imagination but had to have at least six bedrooms and a large, well manicured, front lawn in front of it so it sat further back from the street than the others and had perfectly shaped shrubs and flower beds in front of the house and down the side of the lawn on the opposite side of the driveway which went right up to the garage just off the side of the house.

Tom opened the side door of the van and grabbed his gear before walking through the gate between the house and the garage. As he so often did he could hear the children shouting and yelling as they splashed around in the pool as he approached the back of the house.

Mrs. Fairbanks was sat on a sun lounger watching over her children while reading a book. “Hi Mrs. Fairbanks,” Tom said, “sorry I am late today the traffic was a nightmare and my last job was over the other side of town.”

She looked up and smiled, she had a stunning smile that always looked so genuine, not the false polite smile Tom got from most of his customers. “Don’t worry Tom, I’ve told you before it’s never a problem,” she said.

“Thanks Mrs. Fairbanks,”

“Right children,” she shouts, “Out now so Tom can get on.”

“It’s okay, Mrs. Fairbanks, no need unless I need to add chemicals.”

“It’s time for them to get out anyway Tom. I need them showered and dried ready for their tea.”

To Tom, her three kids always seemed to be very well behaved and not once had he heard her tell them to do something twice. All three climb out of the pool and traipsed through the large patio doors to head straight for the shower.

“Let me know if you need anything Tom,” she said as she followed them into the house.

“Will do Mrs. Fairbanks, thanks.”

There was very little to do this time and Tom was quick to finish which was a blessing as he wanted to get home and crash for the whole weekend. Just as he was leaving Tom shouted through the still open door “All done Mrs. Fairbanks, your good for another week.”

“Thanks Tom,” he heard from deep in the house, “See you next week.”

On his way back to his van for some odd reason it occurred to Tom that he had never seen a Mr Fairbanks, but quickly dismissed this rather random thought just assuming he is still at work every Friday when he called.

The weekend flew by far too quickly but fortunately so did the rest of the week and Tom soon found he was letting himself though the side gate of the Fairbanks house once again and for a change he was actually early. As always that smell of freshly mown grass filled his nostrils as he passed the lawn but no sound of children playing this time. It seemed that every other week the kids aren't there and quite often neither is Mrs. Fairbanks. Tom had assumed that she takes them off somewhere every other week.

When he rounded the back of the house he saw Mrs. Fairbanks was in the pool herself swimming away down to the opposite end. She was wearing a two piece bikini and for the first time Tom was able to get a good look at her from behind which Tom considered to be a very pleasurable sight indeed.

“Hello Mrs. Fairbanks,” Tom called out in the hope that she would hear him without being startled. She stopped swimming and turned around with her usual very pleasant smile that Tom liked to think she reserves just for him and said, “Hello Tom” and began to swim for the ladder.

Tom watched as she climbed out and her top half appeared. Tom’s jaw almost hits the floor as her most impressive breasts straining against the thin material of the bikini top appeared. Tom guessed they must be at least a D or even a double D but in all honestly bra sizes were really a mystery to him. He knew his girlfriend Carrie was a B but only because she made sure he knew it. Why, he had no idea. Women were really quite a mystery to Tom and to be honest, whilst he enjoyed looking at them and, of course, the sex, he was happy to leave it at that.

Tom was transfixed by the perfectly formed globes in front of him as she stood on the side close to him quietly and patiently until he finally lifted his eyes up to her face which was smiling so kindly at him. Tom’s face went bright red and he stammered something about that he best be getting on before heading quickly towards the rear of the pool where the filters are located.

“Shit, I am a complete idiot, why did I have to stare like that? What the hell am I supposed to do now? Hopefully she won’t be around when I get done and I can just slip away quietly I’m not sure I can look her in the face again,” Tom mumbled to himself.

When he got back up to the pool side to test the chemicals he dared not look over at the house in case she was outside or something, last thing he wanted to do was catch her eye. “Only trouble is I have to walk past the patio to get to the gate. God I hope she has gone inside,” he thought.

He remembered a drama teacher once told him, “If your going to cock something up and look like an idiot do it with confidence and you will get away with it.” Tom reckoned this was one of those moments where it’s best to do it with confidence. Having packed his stuff up and stood up. With his head held high and strode with as much confidence as he could towards the patio and out of this embarrassing situation.

Ten feet from the patio, Mrs. Fairbanks walked through the doors out onto the patio towards him still in just her bikini and carrying two exotic looking drinks. “All finished Tom?” She said smiling at him. “Would you like to join me for a drink?”

All Tom’s carefully prepared confidence just rushed down his body and dissipated out into the ground through his feet to be replaced with an even more intense feeling of embarrassment. He was sure that this time it was not just his face that went red but his whole body.

Chapter 2

“Th-Th-That’s very good of you Mrs. Fairbanks, but I have to drive,” Tom stammered as she stood in front of him holding the drinks in such a way that he would have a clear view of her impressive breasts. Look up you fucking idiot thought Tom but his eyes didn’t move and stayed fixed to her ample breasts.

“It’s okay Tom their virgins,” she said which caught Tom by surprise and thought she was calling him a virgin which he wasn’t having lost that at 16. “As in they don’t have any alcohol in them,” she continued, “so your safe to drive.” This made Tom feel stupid and he felt himself go even redder much to the amusement of Mrs. Fairbanks.

She put the drinks down on the table and sat down on the chair across from where Tom was rooted to the spot and smiled at him saying, “I thought since you were early today you might have time to keep me company for a little while?”

Keep her company? thought Tom. Me? Okay I wasn’t expecting that. I wish she would cover up a bit, those tits are very distracting and so difficult not to look at. Come on Tom pull it together.

“In that case yes, thank you,” Tom said smiling as he took the seat opposite.

Tom took a sip of the drink and as the creamy mixture slid over his tongue he got the very refreshing mixture of flavours mostly pineapple complimented with coconut.

“Wow that’s really nice, thank you,” he said.

“I’m glad you like it. Have you never had a Pina Colada?”

“No that’s a cocktail isn't it?”

“Yes but this one is without the rum. Hence why it’s called a Virgin Pina Colada”

“Oh, I see,” Tom said fully realising what she had meant. “You have a lovely place here Mrs. Fairbanks.”

“Tom please call me Kelly, Mrs. Fairbanks sounds like your one of my children's friends come round to play,” she said and laughed. “Thank you, my ex husband designed this, thats where the children are today, with him, as they are every other week.”

“Ah that will explain why they are only here every other week when I service you, I mean your pool. Makes sense now. I had just assumed you did something every other week with them.”

They sat and chatted for over an hour before Tom made his excuses and left. Even though Tom met up with his girlfriend over the weekend he couldn’t get Kelly out of his head and spent all the next week looking forward to seeing her again and hoping that she will be in her bikini again.

The following Friday he rushed through his appointments to make up time so he could get there early again. He turned up 30 minutes early again and as he rounded the corner to the back of the house she was sitting on the patio watching over her children in the pool in just her bikini which pleased Tom immensely.

While she went to organise her children he got on with cleaning the pool. Just as he was finishing she appeared on the patio with two drinks as she did the week previously. They didn’t have as much time as before as she needed to do things with her children but she did promise next week they will have longer.

From then on, every week they would sit, drink and chat about anything and everything. Kelly would like to try different cocktails, virgin of course, on Tom and it became quite a game as he would try to guess what was in them and what they might be called. Kelly always had her bikini on and liked showing off her body to the young man. After that first embarrassment was out of the way Tom quickly learned not to be so sensitive and would quite often stare at her appreciatively trying to not get caught but on the odd occasion she did and Tom got the distinct impression that she really didn't mind maybe even like it.

Tom used to like his last job on a Friday but now he really loved it and hoped it would continue forever. They were very at ease with each other and discussed all sorts of very personal things. Kelly was very helpful and full of advice about any girl or relationship problems he was having and he would offer her his thoughts on the still strained relationship she was having with her ex and how he would still try and control her using the children as pawns in his power games.

After several weeks of their Fridays together, just as Tom was leaving for his usual round his boss calls him into his office to tell him that this will be his last week cleaning the Fairbanks pool as the contract has been cancelled.

Tom didn’t know how, maybe one of the children told him, but he guessed Mr. Fairbanks got wind of their chats. To say Tom was not in a good mood for the whole day was an understatement and was really going to miss his Friday visits there.

As he pulled up on the drive he had a sudden thought and decided what he could do. Walking around the back as usual he found Kelly laying on one of the loungers soaking up the sun, it was one of the weeks where the children were with their father so she was alone.

“Have you heard what he has done now? Only gone and cancelled your contract,” she said

“Yes I know my boss told me this morning. Today is to be the last service.”

“He’s not taking out another one, apparently he expects me to do it myself.”

“There is no need Kelly. I will come round after work every Friday and do your pool for free.”

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