Jacks Lucky Day Pt 01

*This story is from the perspective of Jack, a regular 26-year-old male who has his world turned upside down after a trip to the local supermarket. This is my first ever story, and one that I will continue in other chapters after I have received some feedback from the wonderful readers! I have been reader for a few months now and after reading a few amazing stories recently and have felt inspired to try my luck at writing something myself. Thanks, and enjoy. *

I couldn't believe my luck; my car had just been in the garage with a slow puncture and now a flashing red light on my dashboard.

"Just my fucking luck" I thought.

It had been in and out the garage for the past few months and this time was one too many, I was finally going to sell my first car in the hope of something new. The car was nothing special, 2008 plate Vauxhall Corsa, but it had been my first car and something that I had relied on in the most difficult parts of my life, from visiting my mother during her battle with cancer to making it on time to the 12-hour warehouse shifts to help foot the bills -- this Corsa represented memories. Plus, my ex-girlfriend used to enjoy sucking my dick while I drove, something I can always smirk about when I bump into her in town.

But today was not one of those glorious days, today I had finished work and it was time to go to the local supermarket and do the shopping for the week. I ignored the flashing red temperature light on my dashboard and proceeded to make my way towards the supermarket. As I made my way towards to the super-market, I checked my shopping list.

-Bananas

-Pasta

-Milk

-Cheese

-Bread

After spending 10 minutes wandering around gathering my items I arrived at the till and checked my shopping.

'All there' I thought.

It wasn't much but it was enough to make a basic pasta dish for the coming weeks meals, plus, it left me with enough money to get myself a lucky dip on the lottery and this weeks had managed to hit a 230 million pound jackpot.

'I'd give my left arm to win that money and I would do so much cool shit' I thought.

"HELLO SIR?" said the busy cashier.

"Yes, sorry miles away -- all these and 1 lucky dip please" I replied.

After paying the small £10.45 for my goods, I left the store and loaded my shopping into my cars' passenger seat. On the way home I was filled with daydreams of what a man could do with such a huge jackpot win... I could move to America, surf on weekends and live in a beach-house during the week, I could host the best parties and be surrounded by the hottest women. There was so much life had to offer, so much of it seemingly unattainable to a regular guy like me.

My vision turned into myself driving a Lamborghini to a luxury bar and picking up a more mature single woman, or not single... what the fuck did it matter if I had over 200 million?! I would bring all my friends to live in paradise with me and nobody would be able to say anything. I loved my close friends, they had been the human equivalent of a wolf pack since the starting day of high school in 2004, now 26, half of them had their own children and the other half worked all hours under the sun saving for a mortgage. I was the only one of my friends who had decided to go to college and university, studying a bachelor's in science, animal biology.

The lottery win would set them all up for life, but it would never happen, this must be the 200th week of trying and the most I had won was £20.

After pulling into the driveway I unloaded the car and took myself up into my bedroom, leaving my mother and younger brother downstairs watching the new star-wars movie. A quick shower and I was ready for bed, for such a long day I was surprised that I had even made it to the shop for the groceries but knew it would save me a job in the morning which surprisingly sent me to sleep a lot easier than normal.

'I'm getting old' I thought, drifting off to sleep.

The next morning, I woke up and immediately noticed my cock, hard as it always was in the morning. Almost like my cock woke up and demanded to be swallowed in a lovely girl's mouth, but unfortunately for my cock my hand would have to do.

15 minutes later I appeared downstairs for breakfast, checking the clock on the oven making sure I wasn't late for university, 7:15, perfect timing. I could have breakfast and make it to uni on time for once, I was sure my tutors would be both impressed and unable to resist the temptation to drop a sarcastic comment which I was sure the rest of my classmates would find amusing. With my bag packed and breakfast taken care of I was ready for the day; it was only midweek which meant I was already half-way done. Hallelujah! I lived for the weekends.

"Don't forget to check your lottery ticket Jack, you left it on the side before you went up last night" my mother called.

'Great shout mum' I thought.

The numbers had been called out the night before and I had completely forgotten to check them! Obviously not expecting much I took out my galaxy S9 and opened google.

'Last night's lottery numbers' *search*

I glanced down at my numbers while it took the page a few seconds to load... 7,13,29,30,37,50 and the bonus ball, 3.

"Oh, nice a 7 and a 29... wait, 13... 50... 29, have I said 29, Shit, I've said 29" my excitement was building.

The numbers started merging, they seemed to match my numbers, but my brain hadn't caught up with reality.

"yes, there's a 37, I have that... and the bonus ball is a 3 like mine and holy fucking shit I have won there's the 30."

"Holy fucking shit mum I've won. Mum we have won... Mum? MUM!!!!" I shouted.

My mum came darting into the hallway with a confused look on her face.

"what's the matter hun, what has happened?"

"We have won the lottery mum I can't believe it! We are going to live the life we have always dreamed of, and you deserve it mum, you really do" I replied.

I hugged my mother and celebrated with her, over the next 2 hours we would plan to the very last detail how we were going to spend the money, from vacations to a new house and new cars, I couldn't honestly believe my luck. The best thing of all; seeing the weight lifted from my mother's shoulders after years of being the solitary carer in the family.

The next few days were a blur, travelling down to London to finalise the winnings seemed to take forever, but my eyes were opened to the possibilities that lead ahead of me, seeing the big city for the first time was exciting and I felt free, for the first time money was no issue. I could wear whatever I wanted, behave however I wanted, because I was rich. Super rich. The next 24 hours revolved around bank buildings, signing papers, deciding not to be named publicly as a winner which I always thought would be a stupid thing to do and a bit of shopping. I spent the remaining £500 from my current account on clothes knowing full well the account was about to get a major upgrade.

Finally, having gotten the city visit done with and travelled back home via train, I sat with a cup of tea and a digestive biscuit, knowing that there was 230 million sitting within various banking accounts, the reality of what was happening finally started to strike home, the potential of my new life was unlimited. And I was going to make it glorious.

•A week later

The flight was booked, I had kept the winning secret from my friends for the time being, all but 1. I had told Josh, my closest friend, as I knew I would be stupid to experience the first part of my new life alone. I had sent my mother and my young brother to an all-expenses paid for trip to Orlando Florida, and after mum persisting I went with them I ensured her there would be plenty of family trips in the future but for now I needed time to wrap my head around what had happened with my closest friend and adviser.

The resort we were going to was advertised as a 'private island experience where anything is a reality' accompanied by a price tag of £50,000 per person for 10 days, now normally I would have baulked at the price tag, but this time it was different. The island was partially filled with night clubs, beach bars, restaurants and hotels with the other half being the private resort which included all of the above, and I had booked 2 tickets with the earliest possible flights, me and Josh were to leave the next day.

I spent the next day making sure I had packed everything, I had been informed by the lady from the resort that no clothes or any personal items were necessary but if I wanted I could bring my own clothes, which I had decided to do just in case they had me walking around in a fancy robe or something, this was a new world now and I had no idea what I was walking into. I rang and picked Josh up the following day no longer caring about the warning light on my car. If it broke down, I would order an emergency helicopter or pay strong people to carry us on their backs... anything was possible. In fact, I had organised to meet my new 'Financial and lifestyle council advisor' a 33-year-old named Heather who had come highly recommended by the company that had organised the lottery transfer money.

I had decided to take them up on the idea of a personal assistant (which is what she basically was). I thought she might prove useful for all the time scheduling and chores that I no longer cared to do. Heather was meeting me at the airport and had been given permission to attend the resort for free by the resorts representatives as a gesture of good faith for my future custom. I had told them if the experience was anything like they described I would be bringing my entire party of closest friends whenever I felt like it.

After arriving at the airport and checking in the luggage me and Josh went to sit at the airport bar where we had arranged to meet Heather for the first time, somebody I was going to be spending a lot of time with and sharing all my secrets... I realised as I sipped on my beer that I was nervous. Josh could tell I was nervous; Josh could tell everything that I was thinking, 15 years of close friendship meant that the two of us were fine-tuned to each-others body language and thoughts.

"You're such a pussy, bro. She will be nice don't worry about it... maybe I will get myself a PA, I'm basically worth what you're worth now" he said in his jokey tone.

"yes, you are" I replied.

"But you don't have to do any of the work, just sit back and enjoy your new lifestyle while me and Heather have fun in the private plane booth" I said, smirking.

"Hello, I'm Heather, you must be Jack" a voice said from behind.

'Oh shit!' I thought.

"Hi, I'm Jack and this is Josh" letting the two exchange a handshake.

I hoped she hadn't heard, Joshes reaction was cool, so I assumed she heard nothing which meant that I was safe.

"I'm looking forward to working with you Heather, has the company sorted out the salary details?" I asked.

"Yes, I've been fully briefed, I will run through everything with you on the plane, we should be all sorted by the time we land in the Mediterranean." Heather said while taking a seat.

I hadn't had a chance to take her in but now she was sat down talking to Josh I started to realise how hot she was, and not just hot, she was very pretty. Wearing a grey pencil skirt, white shirt and grey jacket with her blonde hair tied up in a ponytail she looked stunning. Her light blue eyes were enough to distract any man, and the way the skirt hugged her waist and ass was perfect, she was sophisticated and intelligent but sexy as hell. Her sweet smell was intoxicating, the way she brushed a bundle of hair away from her face over the back of hear ear was sexy. She was delicate, but at the same time she looked curvy and in-shape.

'Won't be so bad having Heather around all the time' I thought.

We all boarded the plane laughing together about all the alcohol we would consume (Heather being professionally less enthusiastic) and all the parties we were going to attend over the next 10 days.

During the flight Heather and I talked a lot about how to best invest my money in different companies that were showing promise, buying shares in newly developed medicines was another, apparently if you could time the investment a few months before the product was ready to launch you could demand double your investment in return... I told heather I would think about what to do and wouldn't rush into anything until after the holiday. Josh was playing Gears of War on the planes business class Xbox One console and Heather had opened her laptop finishing off reports.

I needed a power nap; it had been a busy morning and I wanted to be ready for the day ahead. I was enjoying messing around with my reclining seat remote and after 5 minutes of fiddling managed to get my chair to the perfect angle and drifted off to sleep thinking of all the amazing times ahead.

*2 hours later*

I was awake and preparing to land. Josh was sat next to me drinking a gin and tonic talking about how it gave him a different buzz to other spirits, and how he can see why it's becoming such a big fashionable drink. I was distracted, thinking about Heather and the way her suit perfectly fit her curves when I realised, I didn't know where she was. I appreciated that she seemed to have a good balance of when to be around and when to give space, this would probably be the most important part of our working relationship and so far she was excelling, that and the fact I was secretly praying for her to turn up to my room dressed in her skirt wanting to wrap her soft lips around my hard cock. But that was a thought that I simply had to discard from my brain.

'There will be plenty of other women' I told myself.

In fact, Josh had been talking about this a lot over the recent days, and who can blame him. Standing 5'10, dark brown hair and average build, Josh was definitely not a ladies man, he was a nice guy... always finishing last kind of guy. He had previously had girlfriends, but his ambition was always on his business and he never really gave it enough time to develop into something. He did not need to worry about his business anymore and that had given him a new lease of life, we were both ready to wet our throats, cocks and of course to lie on the beach drinking cocktails like all men should.

The experience of getting your luggage from the airport was completely different, the island had its own landing strip, so your luggage was already boarded onto the train before you had even got off the plane.

'Efficient' I thought.

"Ok guys let's do this" I said.

Josh and Heather followed me to the train platform which had a sign that read 'Deluxe Island residents' above its entrance with a list of names, one of which stated, 'Jack & co'.

'Nice' I thought as they headed in that direction and boarded the train.

It was similar to the train on the Jurassic world movie that's on a track suspended in mid-air via big stone pillars... the train led directly to the resort complex, which looked from above like an array of luxury cabin-style houses with public pools dotted in-between. The place looked amazing. When I got off the train a woman was ready and waiting for me. She was tanned and had thick wavy dark hair, wearing sandals, a short skirt and a fitted blue resort polo shirt.

"Mr Clarke and friends, welcome... I am Alice, I will be your host and lead you to your rooms in a short while. In the time being, please follow me this way and you can have your welcome massage."

'Wow, welcome massage, sweet' I thought.

I followed Alice down a very clean corridor, it had glass walls that showed the flowers and miniature streams outside, the floor was sparkling white and squeaked as they walked. Alice stopped at the end of the corridor which had four wooden doors looking like they were entrances to smaller cabins.

"Ok Jack, room 1, would you like a male or female masseuse?" she asked.

"Erm, I will take female please" I said, not wanting a male rubbing oil over my back and digging into my knots with big man hands.

I wanted gentle hands and the touch of a woman. Josh picked a woman and so did Heather, jack wondered why for a second concluding that Heather might secretly skip the massage with her being all 'professional', or that she might feel more comfortable with another woman.

"See you later" I said to the other two and walked straight through the brown door leading into 'Massage room 1'.

There was a massage bed in the middle, a fire burning at the far end and sat facing me in the corner was a woman who looked to be in her mid-twenties, she had her dark brown hair tied back with perfect eyebrows and a few freckles dotted around her nose, she was wearing a masseuse jacket and appeared to be very welcoming.

"Hello, I'm Becky, I will be your masseuse today. I hope the plane journey hasn't taken it out of you too much, hopefully I can help you relax".

"That would be great, I've never had a professional do this before" I replied.

"well let's get to it then Jack, take off your clothes and lie on the bed, put the towel over your backside and ill turn around when you're done" she said having turned around to face the fire.

I took off my clothes and climbed onto the bed lying with my face inside the hole at the top of the bed, I told Becky I was ready and I heard her step forward and then felt warm oil being drizzled onto my back. Sensual music started playing and Becky had begun rubbing my back with oil. She was skilled, she knew exactly where to rub in order to get out his knots and the amount of pressure to relieve stress from my muscles was something only an experienced masseuse would be able to pull off.

I felt relaxed. I was enjoying myself that much my cock had got hard and I was no longer comfy, it was under my body and it was pushing against the bed. I quickly lifted my midsection up and let my cock spring up to my stomach before lying down flat again. This was more comfortable, but now the friction of the table and my body being moved from the massage was making the situation become worse, 10 more minutes of this and I would probably cum over the table. That would be embarrassing.

Becky was still expertly rubbing my back oblivious to the problem I was having. Shifting again to make myself comfortable she asked the question I'd been hoping not to hear.

"Everything okay under there Mr Clarke?"

"I'm sorry I'll be honest" I said, with a new air of confidence (probably coming as a result of the new bank balance).

"I have a huge hard-on, well not huge its about 6 and a half inches... but I'm just getting comfortable so I hope that doesn't gross you out, I might shuffle a little."

"Sir, as the advertisement says... everything here is available. If you like, you can turn over and I will help with your problem" She said, emphasising the word 'problem' with a hint of humour.

I thought about what the offer entailed and realised that this was my life now, these are the benefits of seeing more numbers when you load into your online banking, this is what makes the difference.

"I'd like that Becky, as long as you're okay with it" I asked with a hint of hesitation in my voice.

She was an attractive girl and I had no problem with letting Becky stroke my cock, especially not when I had wanted to cum so bad. I led on the bed with my dick facing the ceiling and closed my eyes listening to the music, waiting for Becky to slowly stroke my cock until I came. I felt oil being drizzled over my chest, stomach, legs and cock... Becky started by concentrating on my chest first, rubbing in the oil and moving down my rib-cage...she rubbed over my stomach missing my throbbing cock by millimetres and travelling down to my legs.

I felt truly in the zone as Becky rubbed me from head to toe. Suddenly, I felt her hands leave my body, lying there with my cock throbbing I felt like begging Becky to sit on top of me and let me feel me bury myself inside her pussy, but just before I moaned in frustration I felt her hand wrap around the base of my cock and travel up the shaft and over the oiled up head. Her hands felt like they were a part of me, sliding up and down my lubricated shaft and over the sensitive head, I let the feeling of pleasure consume me, every nerve ending on the head of my manhood was screaming out.