Jack's Lucky Day Pt. 02

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"Well guys, I'm off to another beach bar... I'm going to try find a pretty girl to have a drink with" Josh smirked. "Ill be back up at the hotel for dinner, catch you guys later" And with that, he turned and headed off across the beach.

I set off walking back to the hotel chatting to Heather about all the different fish we saw, she had decided which ones were her favourite by the time we got back to the cabin. She liked the orange and white clown fish and the blue tang fish like on the movie Finding Nemo. After unlocking the cabin door, I headed off to my bedroom while heather pulled her phone out and started making calls to the bank. I decided to leave my bedroom door unlocked on the off chance that Heather wanted to come and join me. I set the temperature a little cooler than usual as it was a hot day, I whipped off my shorts and t-shirt and got into the shower. The cooler water hitting my warm skin felt amazing.

After enjoying the shower for five minutes I heard the door open. 'Hell yea' I thought to myself. She must be done with the bank call and that only means one thing. I had waited all day for her. My dick started to get hard thinking about her wearing that bikini, her luscious lips sliding over the head of my manhood. I was desperate to be inside her after the experience we shared the night before, my dick ached for her. But did she feel the same, was she going to go back to be the ultimate professional leaving me with nothing but memories, and if that was the case, was I going to have to start booking a massage every morning. I couldn't get caught up on Heather but after experiencing her naughty side it only drove me crazier for her when she walked around in business-mode during the day. 'But she's here in my room, surely that means she wants me' I thought.

I heard the bathroom door open and turned around to see Heather close the door behind her. Still facing the door, she removed her sarong revealing her firm curvy peach. The top of her ass curved away from the slope of her back, sitting high and firm before curving back around towards her body. She glanced down over the back of her shoulder and a few strands of hair fell over her eye as she untied her bikini top glancing up at me. She turned around and let the bikini top fall to the floor revealing her perfect round breasts and hard nipples. "I have been waiting since I woke up this morning" She told me. Her breasts bounced as she walked towards me and my dick went from semi-hard to fully erect. Heather's eyes moved to my cock as she came towards me, she reached out and gripped it firmly pulling me in for a tongue-tied kiss.

"I have waited to feel you inside me all day, I was getting so wet earlier on the beach" she moaned between kisses.

"It's been driving me crazy all day" I told her, desperate for her to take me in her mouth. I put my hands on her cheeks for one final kiss and sat down on the shower seat. I pushed the button and let the water fall over my shoulders. Grabbing her hands, I pulled her down towards me. She knelt in front of me, I put my hands on the back of her head and guided her lips towards my throbbing penis. I felt her soft lips part and let me enter her, the warm velvet insides of her mouth swallowing me, inch by inch until I finally felt my tip slide down the back of her throat. I slowly moved her up off my shaft until only the head was in her mouth and then pushed down on the back of her head, guiding my cock back in and down her throat. She was good at giving blow jobs, she knew what she was doing. She knew to look into my eyes as she swallowed my entire length.

"I need to fuck you" she begged, standing up and turning around. Bending over she lowered her pussy down on to my throbbing cock, taking the whole length on the first entry. It felt warm inside her pussy and so wet. I saw her juice coating my cock as she pounded down on me. She was moaning loudly, and I could tell she had needed this all day. I loved the way she moaned, it was deep and passionate but ended higher pitched showing her feminine side. I gripped an ass cheek in each hand and helped her pump her ass up and down impaling herself on my hard cock, each time my dick slammed into her she would add another moan to her song. I felt my balls tingle and knew I was going to cum.

"Heather I'm close" I moaned at her trying to hold in my load.

"Cum inside me Jack I want to feel your hot cum inside my pussy" She moaned back at me, speeding up her tempo.

The tingling feeling in my balls turned into pure pleasure and I erupted inside her, I could feel her pussy walls rubbing against my cock as I unloaded my balls. My thighs twitched a few times as she slowed down still sliding up and down my sensitive cock. Heather stood up off my cock and pulled me up for a kiss. It was filled with emotion and I could tell she felt the connection as strongly as I did. Who cared if we met because she was sent to work for me, sometimes you can't help who you fall for and this was one of those times. As we parted lips Heather bit the bottom of my tongue and grabbed my hand. "I need your fingers inside me" she said.

She cocked her neck and I reached down, entering her with my first two fingers. I worked my way inside her feeling for the little rough patch of skin. 'There's her spot' I thought, feeling the little bumps on the inside roof of her vagina. I nibbled on her neck as I moved my fingers in a 'come here' motion, rubbing against her G-spot. Her hips started swaying in rhythm with my fingers, she was breathing heavily letting out little moans. I continued to concentrate on her G-spot and her body was responding to me, her swaying had become more aggressive like she was trying to fuck my fingers as hard as she could and her legs were becoming weaker, causing me to have to support some of her weight with my free arm. Her pussy felt amazing on my fingers, I could feel she was tight but her pussy juice was lubricating my fingers nicely. I felt her hole tighten around my fingers and her whole body tensed up in unison, she bucked on my fingers and her legs started shaking.

"Oh my fucking god Jack, that was amazing" she gasped after her orgasm had let her regain composure. "I felt it rush through my entire body" she cooed.

"Why don't we get your shaky legs over to the bed and get you dry" I teased her.

"Shut it you, this is your fault" she told me as she hobbled out the shower, holding on to the towel rail to keep her upright.

I got us a pair of bath robes and handed one to Heather. We walked into the bedroom and sat down on the bed. I found the TV remote and started to investigate what kind of TV entertainment was on offer at the resort. There was Sky TV, BT Sport, Netflix and Amazon video all in HD quality. 'Not bad, a guy could get used to this' I thought, glancing over at Heather towelling down her toned legs.

"So what do you fancy for dinner today, any word from Josh?" I asked her.

"I'll check my phone now to see if he's messaged. I haven't known him that long, but I would guess he will be happy eating anything" She said.

"That does sound like Josh actually" I laughed back. "If he hasn't messaged you let him know we are going to wander down to the first Italian in the resort, and then I would like you to book us a table."

"You're getting better at this being a boss thing Jack, it really suits you" she said with hint of adoration in her voice.

"Well, I had better get used to it sooner or later I suppose" I said absently, flicking through the sports channels. I had completely forgotten that the weekends football games were on and although disappointed I couldn't watch them down at the beach bar, I could still grab a beer from the bedroom fridge. My bedroom had the bonus of Heather wandering around half naked in her beach shorts with her boobs hanging free. They knocked into each other when she lent over to pick something up from the floor and jiggled around when she walked across the room.

'Heaven' I thought, looking up at the football and back down to Heather's breasts.

12
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
1 Comments
tinfoilhattinfoilhatabout 4 years ago
Nice start...

This story could go lots of ways. Hopefully Jack will get a bit more mature quicker. 200 mill won't last forever unless you plan it out. But it's just a story. Woohoo...let it roll.

Share this Story

READ MORE OF THIS SERIES

Similar Stories

I Bet You Wheel: Greek Alliance Fraternity must uphold their side of deal for the gameshow.in Fetish
Birthday Bound Boyfriend makes my bondage fantasy come true.in BDSM
Cuffed Together Strangers find themselves locked very close together.in BDSM
Escapades 3 adrenaline junkies try to beat an extreme escape room.in Fetish
Lucky husband Lucky man!in Exhibitionist & Voyeur
More Stories