Jack's Lucky Day Pt. 01

She was relentless, rotating her hands as she slid up and down the shaft. She was panting, and it was turning me on even more than I was before. I could feel a huge swelling in my balls and knew I was close.

"I'm going to...cum" I managed to mumble.

Becky brought her second oiled up hand and wrapped it around the head of my cock rubbing it with her palm while her first-hand worked up and down my oily shaft. The feeling of her hands was sending me over the edge, I could feel every last bit of movement from her oiled hands, I was thrusting my hips up in time with her pumping my shaft, each time her hand moved over the ridge separating the shaft from the head it shot electric bolts up my spine. I felt my balls tingle and my whole body tensed up in anticipation, Becky was clearly an expert as she recognised my imminent release, gripping my cock tighter, causing me to erupt into her hand as my sticky semen pumped out into her palm. I glanced at her and noticed my cum dripping from the gaps between her fingers.

"That was incredible!" I whispered.

Becky cleaned her hands and looked at me.

"Thank you, Mr Clarke, if you want to shower the oil off there is a shower room to your left. There will be clean clothes in there ready for you and Alice will see you outside in 15 minutes to take you to your cabin."

With that she walked out and I was now left alone sat on the massaging table fully naked with a sloppy cock. Moving over to the shower room door I peeked my head through before entering, it was huge! There was a walk-in shower on the far wall with what looked like sprays coming from all directions, bath robes along the wall to my left and to my right were sinks, toilets and open cupboards loaded with a large choice of shorts and t-shirts. Everything was so modern and styled that I kept forgetting I was on a Mediterranean island; the experience so far had lived up to expectations.

I found myself wondering again about all the amazing things I was going to experience; each time I was alone I had added more things to my to-do list. Now I knew that sexual experiences were on the cards I wondered if I should add more types of sexual experiences to my ever-growing list. I showered, dried off and looked at myself in the mirror... my beard had grown a little shaggy and my hair needed cutting. Making a mental note to request a haircut I dried off and put on some of the free clothes. I settled for some jeans and a t-shirt, both seemed to be nice designer clothing and finished off the look with some socks and a new pair of Nike trainers.

Alice was waiting for me with Josh and Heather, Josh looked like he had taking full advantage of the massage as he had the world's biggest grin across his face, Heather however looked as professional and sexy as ever in her usual grey pencil skirt suit. I was sure she was attracted to me, every time we made eye contact, she seemed to become fidgety and start talking too much. She was waffling on about the evening plans and what kind of clothing I wanted her to wear so I let her know she should relax and wear something a little more casual, and that I expected to see her in the pool later that evening.

"Maybe if I have time, sir" she told me.

'I'll see what's under that skirt if it kills me' I thought.

Alice lead the 3 of us through a door and onto an outdoor path that appeared to lead off in many directions to the nearby cabins in the distance hidden behind the trees. After arriving at my cabin, the first thing I noticed after walking through the front door was a huge bar and kitchen area on the opposite wall. Josh told me he was going to check out his room and have a shower as he was still a bit sticky from the massage, I didn't ask for any more details.

Heather and I followed Josh down the hallway and found our rooms at the end, Heather started flicking through her notebook suggesting activities and I had to interrupt her.

"Heather" I said.

"I read there's a jacuzzi on the second floor and I'd like to go check it out, put your bikini on and meet me up there in 5 minutes."

She looked slightly nervous about my suggestion but agreed anyway and went off into her room to presumably get changed. I found my bedroom door and walked inside. It was amazing, there were LED lights around the large circular bed and what looked like the comfiest mattress and quilt he had ever seen. The on-suite bathroom was sparkling clean had had a miniature jacuzzi and walk in shower. The sliding glass doors at the far end of the room led out onto a balcony that hosted a table and chairs with a nice rustic wood-burner.

'This would make for an amazing romantic night with Heather' I thought.

'We could open a glass of wine and watch the stars before coming back onto the huge bed and tearing off each other's clothes.'

Shaking my head to rid myself of an idea that was starting to make me feel horny I pulled off my free clothes and found some swim shorts in a cupboard across from the bed. I put them on and headed for the jacuzzi. I wasn't shy about my body but I wasn't hugely proud of it, I was no gym-goer but I had been training Muay Thai for a few years now and I had a decent amount of muscle even if there was a little bit of fat over the top.

Reaching the top of the stairs I found the huge jacuzzi I had seen on the website pictures, finding the control buttons I turned the heating up a little bit and set the bubbles off to a medium power. It felt amazing, for 5 minutes I just led there and enjoyed the relaxing lifestyle I was starting to get accustomed to, that was when I heard the door swing open and stood in the doorway was Heather, wearing a loose-fit men's t-shirt covering herself. She must have been in her bikini because her legs were bare, they were long and slim with perfectly toned thighs.

I felt my cock getting hard and thanked the lord the bubbles were there to hide it. If my cock wasn't hard now it would be soon. Heather walked towards me and upon reaching the jacuzzi pulled the bottom of her t-shirt up and over her head, revealing an amazing set of natural 32D sized tits, a flat and toned stomach and what looked like a fully shaved pussy. It was hard to tell, but the illuminous orange bikini was tight fitting and there was no pubic hair to be seen.

I blushed when I noticed Heather had caught me staring but she let me know that with me being a young male she had expected I might be a little distracted when she got her clothes off.

'So, she's been thinking about taking her clothes off for me' I thought.

I liked that idea. Heather climbed into the jacuzzi and I couldn't help but notice her tits wobble as she sat down... I had to have them.

"so, how are you finding the experience so far?" I asked her.

"It's good sir, it's far from the experience I thought I would have when applying for the position."

"Well, I am glad you're here... I couldn't imagine anyone better following me around all day."

Heather laughed and I could tell she was started to feel more comfortable.

"So Heather, I've been thinking" I said, "We are going to have to be really comfortable with each other if we are to have a good working relationship."

"Yes sir, I agree. I am here for anything you need, even if that is just to chat when you're feeling down -- hopefully in a few years we will be perfectly synchronised and I will be able to keep you happy without even thinking about it." She said with a warm smile.

"Keeping me happy is easy Heather, I'm a simple guy... I like pizza, burgers, football and gorgeous women like you" I said.

'Did I really just say that?' I thought, slightly embarrassed.

Heather blushed; I could tell there was something there between us.

"Thank-you sir, you're an attractive man. If I am honest, it has been distracting me. I'd have preferred someone old and wrinkly" She said, winking at me.

"And as for the burgers and pizza, that's easily arranged" She added.

I wasn't going to let this opportunity pass, so I slid closer and told her that we could be more than just a working relationship. I decided to take a chance and put my hand on top of her thigh. Damn they were smooth, and she felt amazing to my touch. Heather looked uncomfortable but as I stroked her leg, she seemed to be becoming more comfortable, looking at me with eyes that screamed she needed to be fucked.

"It's been a while since I've... you know." She said, looking down at the water.

"Don't worry" I replied, "It has been a while for me too."

She seemed to gain more confidence, sliding closer towards me and moving her hand on my thigh. I let go of her leg and picked up her hand moving it on to my cock. I leaned towards her and she met me half-way... we kissed; her mouth moved into a smile as my cock started to grow in her hand. I felt her tongue push at my lips and make their way in my mouth, our tongues clashed and wrapped around one another in a lust-filled passionate exchange.

I lifted myself off the jacuzzi seat and slid my boxers down and threw them on the floor. Giggling, she reached around her bikini top and untied it, letting it fall off into the water. I grabbed her bikini and threw it near my shorts while laughing, soon followed by her bikini bottoms that she had decided to remove, she couldn't get out now without showing me her perfect wet tits and pussy.

Heather nuzzled into my neck and whispered in my ear, "I am going to milk you dry Jack Clarke, and then you're going to want to fuck my pussy every day for the rest of your life."

Just hearing her sexy whisper make my cock throb. Heather lifted her leg over me and sat on my knees facing me, pushing her perfect tits into my mouth. I sucked on her hard, pink nipples and squeezed them in my hands.

"Harder" she said.

"Bite my nipples harder" She begged.

I chewed on her pink nipples and I could tell it was sending her crazy, her hand came from beneath the water and two of her fingers went straight into my mouth. I could taste and smell her pussy juice and sucked on her fingers like I would never get the chance again. She returned her hand under the water and gripped my throbbing cock. In once swift movement she lifted herself up and I felt her rub her pussy on the end of my cock, without massage earlier that day I would probably have cum then and there, she was so sexy and I couldn't believe I'd ever have the chance to fuck a girl this hot.

She slowly sat down, and I felt the inside of her soft, wet pussy gripping my cock. She slowly lowered herself down as far as she could and remained there impaled on me for a moment. Her pussy was wet and warm, I could feel the inside of her pussy on my cock and I never wanted it to leave.

Once she had gotten used to me being inside her she started grinding forwards and backwards. I could feel her clit rubbing at the base of my shaft, the velvet inside of her pussy milking throbbing cock. I lent forward taking one of her nipples in my mouth and started chewing, she threw her head back in ecstasy and thrust into me, grinding harder while moaning my name.

"Jaack, oh baby. I have missed riding dick. Give it to me baby, fuck me. Fuck me!" she moaned.

"Fuck your assistants tight little pussy." She said, throwing her head back in ecstasy.

I let go of her rock-hard nipple and marvelled at her perfect tits, jiggling around as her hips swayed back and forth.

I was starting to feel my balls swell and knew the end was near.

"Heather I'm going to cum" I gasped.

"I can't hold on much longer, your pussy feels amazing."

She didn't stop for me, if anything it felt like she was speeding up. She looked at me with her piercing blue eyes.

"cum inside me sir, own this pussy" she begged, still aggressively swinging her hips into me.

Hearing her talking this dirty sped up my release and I felt my balls start to unload as I came inside her tight hole. A shiver flew up my spine and I sat there twitching. She squeezed her pussy and milked the last few drops from the end of my cock, clearly loving the control she had over her new boss. I lent my head back and rested it on the jacuzzi headrest trying to work out in my head what had just happened.

Heather stood up, letting my limp cock fall out her pussy. She climbed out the jacuzzi, flashing her perfect ass towards me and bent down giving me a great view of her tight pussy and little pink hole. Her pussy was perfect, it was tucked in with just a slight protrusion of inner lips, swollen after riding my cock. She picked up her t-shirt and put it back on, leaving her bikini on the floor. Her stiff nipples poked through her wet t-shirt, she was so sexy I wanted to bury my head in her pussy and eat till my jaw couldn't move.

'Maybe another time' I told myself.

With that, Heather turned around and headed for the door back towards the bedrooms. Looking over her shoulder she looked at me with the most lust-filled eyes I have ever seen.

"Thank you, sir, maybe you would like to continue this in the bedroom, I'm aching to cum over your cock" she moaned, winked and left the room.

I caught a glance of her wet shirt clinging on to her perfectly toned, round ass as she left the room.

'Maybe I will fill that hole in if she'll let me' I thought to myself.

After another 15 minutes in the jacuzzi the door swung open and Josh entered with a bucket full of beers in ice.

"Sup man, its time to start enjoying this holiday" he said, jumping into the jacuzzi next to me leaving the iced beers on a table next to the jacuzzi.

Josh was opening his 4th beer 25 minutes later, amazed at the story I was telling him about me and Heather.

"I don't think we are relationship material man; I think we are just attracted to each other and while we are on this island, I just feel like anything is possible" I said while sipping my beer.

Josh was a little jealous but we both agreed there would be plenty of chances to get our dicks taken care of over the next 10 days, he was already happy after his massage treatment which had apparently gone all the way and he had finished off balls-deep in his masseuses mouth.

'Maybe Heather will fulfil my threesome fantasy, that would be awesome... Heather and another girl naked with me in the same bed' I thought.

Another 30 minutes in the jacuzzi and my fingers were starting to resemble raisins, so I told Josh I was going to dry off and head to bed. He agreed and we both made out way downstairs and into our bedrooms.

"Goodnight bro get a good-night sleep we have a huge day tomorrow" I told him.

Josh disappeared into his bedroom after wishing me a good-night sleep and I carried on towards my bedroom door. I hoped heather would still be in here. I opened my bedroom door and walked inside, on the floor next to the wardrobe was Heather's oversized shirt. Music was playing in the background and I could smell rose-scented candles... I had a good feeling about this.