Jack's Lucky Day Pt. 02

The lighting in the room was perfect, not dark enough so I couldn't see, but warm, cosy and sexy. Heather had lit candles around the room, lighting the bed with a warm orange glow. The deep orange light danced with the shadows on the wall, the feint crackling of the candles burning. I walked over to the balcony door searching for my treasure when I heard a voice behind me.

"Took you long enough sir, the room service here has all kinds of stuff" Heather giggled, standing at the bathroom doorway.

I turned and saw her, she had her long blonde hair down, it fell in waves and ended just below her shoulders. She was wearing a red laced thong with black trimmings attached to black stockings and a matching bra holding her perfect D-cup breasts. Her make-up was flawless, red lipstick accompanied by a touch of black mascara enhanced her blue eyes. I had always believed that the truly beautiful women were way out of my league, that I would never experience feeling the warmth of something so perfect... but here I was, standing before a woman who was exactly that.

"You look amazing" I stuttered.

"Come and sit on the bed Jack." She replied seductively.

I slowly approached her, I could smell everything; The candles, her perfume, the chlorine from the jacuzzi. I reached the bed and sat down, I felt enhanced by her, she had set this up and was going to do whatever she wanted with me. She slowly knelt in front of me and pulled down my shorts revealing my almost fully hard cock. Taking it in her hand, she parted and crawled between my knees. Looking up at me she bit her bottom lip and stared into my soul. Her hand pulled back the foreskin of my rock-hard erection, she lent forward and took the head of my cock in her mouth letting her tongue glide over the tip.

I felt saliva coating my cock as she sucked further down the shaft, it was dribbling off her bottom lip and seeping down onto my balls. I could feel the opening of her throat and her tongue rubbing against the bottom of my shaft. I felt myself enter her throat and with one final push she had managed to get her lips the entire way down my cock. It was the best blowjob I had ever received, and it had barely started yet. Heather brought her lips all the way back to the tip and slid them back down to the base, taking my cock into her throat once more. Up and down she sucked, letting out the occasional moan telling me know how happy she was to have my cock inside her. She was fucking me with her mouth.

"Heather that's amazing" I moaned.

She reached behind her back and unclasped her bra, discarding it on the floor. I saw her tits spring free; they were perfect, and I noticed how hard her nipples were. Her delicate hands came up and squeezed her breasts, leaving with a little pinch of her nipples. The sight of a drop-dead gorgeous woman slobbering on my penis while gripping her tits sent me over the edge. I felt the tingle in my prostate and my moans grew louder.

"Heather I'm going to cum any second now" I almost begged her.

No response, instead she sucked harder and gently massaged my balls encouraging them to unload inside her. A euphoric feeling swept over me as I shot cum down her throat. Heather moaned as she swallowed, sucking her way up my cock making sure no cum escaped. I led back on the bed breathing heavily, forgetting where I was for a few seconds.

Sitting up I saw she had bent over with her legs straight and her fingers touching the floor. Her legs were straight giving me a full shot of her barely covered ass and pussy. I could see the outline of her outer lips and in between them where the colour of her knickers had gone darker from her wetness. Her hands came up, unhooking her red thong from her stockings and slowly pulling them over her bum and down her legs, exposing her wet pussy and little pink ass hole.

"Now it's your turn" She said, turning around and pushing my back onto the bed.

Heather crawled up my body and put her knees either side of my head.

"Go slow at first please baby" She moaned. "I want you to go faster when I start rubbing my pussy."

"You smell amazing Heather" I told her.

She dropped her body weight a few inches, her soft, wet pussy lips pinning my face down. I slowly licked from her hole up to her clit and back down again, remembering to start off slowly. I spent a few seconds tonguing her hole and then move up to concentrate on her nub. She was looking up at the ceiling moaning, gripping her tits. I continued my slow technique and noticed that Heather had started slowly rocking on my face, spreading her juices over my nose mouth and chin, I could tell she was being taken by an impending orgasm. One of her hands moved down to her clit and started rubbing while the other gripped my hair. I did what I had been instructed, diving into her pussy with my tongue, licking faster with more pressure. I reached up and played with her nipples, it seemed to send a shock down her spine causing her to arch her back and let out a deep moan.

"Holy fuck! I'm cumming!" she gasped.

I Felt her thighs shaking against my jaws and tasted her fresh cum on my tongue, it was thick and creamy but had a sweet flavour. I had never had that experience before, to have my face ridden so passionately by a woman. I was proud, but more to the point, I was hard again. Heather looked flustered and was panting heavily while eyeing up my hard cock, she grinned, grabbed it and started slowly stroking it.

"Oh good, I have 1 more surprise for little Jack" she bit her bottom lip.

"Hey, don't call him that, he's slightly over the average 6 inches" I teased back at her.

"Well, big-little Jack, I need to put some special lube over you if you're going to fit where I want you" She cooed.

Heather climbed off the bed, bent over slightly and showed me what looked to be a small metal plug hanging out her ass. She looked back at me, reached around and slowly removed it. I saw her eyes roll into the back of her head for a second as the widest part of the plug left her ass hole. My excitement started building, I had wanted this since I first saw her wearing a pencil skirt in the airport, then again when she left the jacuzzi. Now I was going to get it, my cock twitched in anticipation.

"When did you sneak that in there!" I asked her, amused.

"Ah, ah... sorry sir, a lady never tells" she quipped back.

Opening the drawers beside the bed she removed a bottle of lubricant and rubbed a generous coating on my cock. She picked up my hand and squeezed a dollop on my first two fingers, bending down and telling me to slowly put them in her ass. I couldn't believe I had assumed her to be a well-behaved workaholic. She was a workaholic, but she wasn't very well behaved. I loved this new side of Heather, I loved that she worse smart suits during business hours and I loved what she was capable of outside business hours.

I slowly entered her ass with the tips of my fingers, working the lubricant over her puckered hole pushing slightly further each time. The first few pushes met some resistance, but I felt Heather relax and my fingers started making much better progress. I saw her lips part and a gasp of air exit her lungs. She pushed back on to my fingers helping me go deeper, her breathing growing heavier the deeper I went. I had my fingers in as deep as they could go, I held them there and let her adjust to something so far inside her ass. I slowly removed my fingers and we both climbed back on the bed. She swung her leg over my body which positioned her facing away from me, my cock inches away from her tight ass hole.

She reached under her body and gripped my shaft, guiding it towards her lowering hole. The tip of my penis pushed at her tight hole and I felt it start to give way. My lubricated cock slid through the tight entrance, I couldn't believe how tight it was, it felt like a fist gripping my cock but soft like velvet. We both shared a deep moan as I entered her. Heather lent forward and held my legs keeping herself in place, from this angle I could thrust up into her and control the speed.

I started thrusting slowly, I was getting deeper into her ass. I could tell she was experiencing sheer pleasure. Her hands reaching up exploring herself, following her curves and tweaking her nipples. She moaned my name in a way that told me she was mine. Her back was covered in a fine glaze of sweat. I could hear her breathing growing heavy, she was losing control over herself and began letting her weight drop on top of me. Her perfectly toned ass looked amazing bouncing on top of me. I led back and let her fuck me, losing myself in the pleasure of her tight ass sucking on my throbbing dick.

"Jack, I need you to fuck me hard on my knees like a dirty little slut." She begged.

I lifted her off my cock, threw her onto the bed and stood up. I grabbed her hips and lifted them off the bed pulling her into a doggy position. Her ass hole looked amazing, covered in lube and slightly more open that it had been earlier. I lined my cock up with her hole and slowly glided it inside. She moaned and dropped her head to the bed arching her back.

"I love how you feel inside me, now grab my hair and fuck me" She begged.

I lent over and grabbed her hair. I built up speed and was soon fucking her hard while I pulled her hair back against me. Heather had now lost the ability to speak and was just moaning noises. I could feel the sweat on my body, and I was sure going at this pace I wouldn't last much longer. I could feel the soft insides of her ass grinding against my cock from every direction. Her bum cheeks bounced as I fucked her relentlessly. I felt the usual prostate tingle and then the euphoric feeling returned as I pulled on her hair and thrust forward, shooting cum inside her ass.

"Heather, that was amazing" I panted, out of breath and still inside her.

"Yeah... Jack... I... yeah." She managed to say, lying forward on the bed allowing my semi hard cock to slip from her.

"I think it's time to get in bed and have a sleep, that was amazing Heather" I told her.

"Good idea, I think it might take me a while to compose myself and fall asleep after that" she laughed.

Heather spread herself out on the bed while I blew out the candles before joining her. Both of us were too hot to sleep under the covers so fell asleep, one of her breasts in my hand, legs entangled naked on top of the bed

-The next morning

*knock knock knock*

I lifted my head off the pillow and realised I was alone in bed. Where was Heather, why hadn't she stayed the night? 'I hope she doesn't feel weird about last night' I thought.

"Open up man, it's time for some breakfast and then we have to check this place out" Josh said through the door.

"Hang on" I shouted back.

Half asleep I managed to root out some sandals, shorts and a t-shirt from the wardrobe on the way to the door. Josh burst in full of enthusiasm, he was talking about what he had seen in the resort's leaflets... surfing, beach bars and snorkelling, all included in the resort experience. I handed him the bedroom phone and told him to dial the number and book 3 spots for whatever he wanted to do that day.

"And Josh, call room service for some breakfast I am so hungry I could eat an entire buffet" I added.

I left him on the phone and got into the bathroom. The shower was incredible, there was an iPad control panel on the wall that let me set the temperature, power, extra jet wash, lighting and just about everything else you could possibly control in a bathroom. There was a seat in the shower and a button next to it. I turned on the water via the iPad and sat down. 'I can't not press this button' I thought, pressing the button.

A heavy stream of waster began falling over my shoulders from the wall behind me, it was incredibly relaxing and an epic way to wake up in the morning. Everything about this place was luxurious. I sat under the relaxing waterfall and thought about all the changes that had happened to me in the last week. I hoped my mother and brother were having a good time on holiday. After a bit of thought I decided I was going to treat her to the house she always dreamed of; a lake house on one of the waters in the lake district. My mother loved the countryside, she adored the old-style stone houses and village lifestyle. I was going to be busy, so I decided I would buy her a puppy that she could raise and take for countryside walks, a companion to keep her company when me or my brother aren't home.

"There's only three breakfast options Jack, which shall I get?" Josh shouted from in the bedroom. "There's a breakfast banquet for one, breakfast banquet for two, or the mega breakfast banquet."

I thought for a second and went for the option that every 26-year-old male with too much money would make, "get the mega breakfast banquet."

I finished my shower, got dried and headed back into the bedroom. Josh was slouched on the bed flicking through the Argos catalogue style room service. "You should see what's on here Jack, you can order anything from Hugo Boss t-shirts to bondage equipment... this place is seriously crazy dude" he said chuckling as he changed to the next page full of handcuffs and different toys.

Me and josh must have looked through that entire damn catalogue laughing and joking at all the crazy shit on there. I told him I was definitely buying a couple' speed boats, but I was going to make sure mine was faster than his.

The breakfast arrived and it was like nothing I have ever experienced before. Sausages, bacon, scrambled eggs, poached eggs, fried eggs, cooked tomatoes, hash browns, black pudding, yogurt, fruit, croissants, toast, beans, cereals; everything you could ever want for breakfast. 20 minutes later with full bellies we decided to head towards the private beach where we were going to do some scuba-diving at 1.30 pm. I had told Josh that I wanted to check out a beach bar and have a few drinks before we got lunch, he agreed, and we decided to gather our stuff and head down to the beach. I couldn't help but wonder where Heather had got to. It was only 8.30 and to be fair she wasn't due to officially start working for me until 9. 'A morning kiss wouldn't have gone amiss' I thought to myself.

We left the cabin and headed down a small cobbled path towards the little resort village just next to the beach. The cobbled path must have been a few hundred meters long with palm trees all the way down either side providing shade while you walked. The town was filled with wealthy people wandering around in their swimwear. We headed through resort passing several bars on both sides of us, people sat on the verandas drinking beers and cocktails. Each bar we passed had different music playing, each song growing loud as we walked by and fading into the distance as we moved on, only for the next bars music to take its place. This place was amazing. I couldn't stop looking at everything, brand new Ferraris, Bentleys and other luxury cars dotted around in the parking spots.

We made our way through the town and onto the beach where we found a cool little bar called 'The Gatsby'. 'Nice name' I thought. I felt my phone buzzing in my pocket and checked it to see Heather's name.

"Hey there, how are you?" I asked, it was still only 8.45, she had 15 minutes.

"Hey sir, I saw you headed down to the beach from my balcony I am on my way down, I will be 10 minutes" she told me.

"No problem, I'll have a sex on the beach waiting just for you" I said with a hint of mischief.

I heard Heather giggle and the phone went down. Me and Josh found a table and sat down and within seconds a waiter had approached us and taken our drink order. One sex on the beach, one strawberry daiquiri for Josh and one gin and lemonade with a dash of orange for me. I bought some sunglasses from the guy walking around the beach, according to the bar staff he wasn't one of the usual guys you find abroad trying to flog fake merchandise, he was a representative from Ray-Ban and some of his glasses went way up past the 2,000 mark. I bought us all a different pair; the cost came to around 7,950 euros. Paying that much money for anything seemed extremely alien to me but splashing out occasionally wasn't going to hurt, especially not with the amount of money I had won.

A few minutes later me and Josh were sat talking football, our sport of choice, when I noticed Heather appear at the entrance to the bar. She was wearing a dark blue bikini and had a sarong draped across her hips, falling on her thigh just lower than her bikini bottoms. She was carrying a laptop bag and beamed a huge smile towards me when she saw where we were sat. I told her I had bought her a little something and gave her the sunglasses from the Ray-Ban guy. She knew what brand they were immediately and at first refused such an expensive gift, but with a little insisting she accepted, hugged and thanked me profusely. She sat down with her new shades on looking incredibly sexy as she sipped her cocktail with a big grin on her face. 'That smile is well worth the money I paid for those' I thought to myself.

The three of us spent the rest of the morning and lunch time chatting in the beach bar drinking cocktails, we eventually ordering some chicken wraps at around 12:15 which helped sober us up. Sat looking out over the beach I noticed my sunglasses allowed me to watch people without anyone noticing. There were so many gorgeous women in skimpy bikinis, some even had no bikini tops on. One woman who looked in her mid-forties was about 15 yards away from me rubbing sun lotion onto her tits, they were big natural boobs that hung slightly lower than I guessed they did 15 years ago, but still firm, still fuckable. The rubbing must have turned her on because her nipples had stood up reacting to her touch. She looked confident; she was showing them off proudly. Some people around here looked like they paid a lot for their tits and she knew she had them beat from pure genetics. I thought she reminded me a bit of a MILF that used to pick up a kid I knew at high school, she would turn up in her white range rover with her shades on knowing every horny teenager there wanted to fuck her.

1.30 came along and it was time to go scuba diving. We headed over the beach to the scuba lodge. The three of us were taught all the do's and don't's of scuba diving. We would each have an experienced scuba guy at hand in case we needed anything which was helpful for us newbies. I boarded the boat behind Josh and Heather, and we travelled out a short distance around some rocks on the end of the island and into a cove on the other side. The boat stopped and the instructor told us to sort out the last bits of our gear and prepare to dive. I got my gear sorted and sat on the edge of the boat facing Josh. I glanced over at Heather and gave a thumbs up which she returned; I did the same to Josh although he thought it would be funny to throw his middle fingers up at me before falling back into the sea. 'Cheeky fucker' I thought, laughing to myself.

I couldn't believe how many different colours there were, the fish came in bright blues, oranges and whites. There were long fish and D-shaped fish, all seemingly living within their own ecosystem. I studied this sort of thing at university but seeing it before my eyes was amazing. I looked up and saw Josh and Heather scouring over the reef, both completely in their own world. I had a moment of happiness, a warm feeling spread through me and I realised how grateful I was for any of this to even be possible.

'I'm going to look after those who are close to me' I told myself. 'But for now, it's time to enjoy the amazing sea life.'

Around 30 minutes later we were back on the boat heading for the main beach. I took off my scuba gear and decided that I was going to wander back to the hotel for a shower to wash off all the sweat and salt-water on myself. Heather agreed to come with me as she needed to make a few phone calls, mainly to the bank explaining the large payment for sunglasses and to check on how my mum and brother were doing over in the states. I was happy when she decided to come back with me, I'd been tortured all day looking at her perfect body wishing I could just rip off her bikini top with my teeth and chew on her nipples. I had respect for Heather, but at the same time I felt like an animal around her. It was pure passion and energy, withheld and contained throughout the day just waiting to explode.