A Fresh Start

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

"Actually, I've only been here once before. I guess it's for tourists really but I like coming down to the pier and watching the sea-lions. They make me laugh. The way they waddle on and off the pontoons, and they can be so grumpy with each other."

Connor wanted to tell her about the Sea lions and dolphins and whales he'd seen but he knew it would sound like one-upmanship.

The waitress came back quickly with their drinks then took their order.

"I think you have to have the burger. It's the law," Chelsea joked.

"No problem with that. You want any nachos?"

"Mmm yes please."

"And the biggest bowl of nachos you do please," he asked which made Chelsea laugh.

"I guess this is the point where we tell each other about ourselves," she offered.

"I guess it is," Connor said with a bit of a sigh.

"Is it a problem?" Chelsea asked.

"No, not really."

"Why don't I go first, it won't take long," Chelsea suggested. "So, my name is Chelsea Cartwright. I'm 25, originally from Cincinnati, Ohio. I have a degree in Sports Science and I've been out here for two and a half years now, working at the gym. The pay is rubbish and I'm as poor as a church mouse. I still owe a fortune in tuition fees and if I'd known how badly paid it was I probably would have chosen something else but I'm not really motivated by money.

Chelsea's voice trailed off for a moment

"Oh and I live with my flatmate and best friend, Presley."

"Is Presley a gym instructor too?"

"No she's an air hostess. She works for an Asian airline so she tends to do long haul. She's the sort of person you might not see for a fortnight but then it's like you'd never been apart. She's a stereotypical air hostess, a bit of a good time girl. I guess we both are really. We're both single and enjoying life. I miss her when she's not around."

That was about as much as Chelsea was prepared to divulge. It was a first date after all and she didn't want to shock Connor with the whole truth. She fished out her old phone and showed Connor a picture of the two of them. She knew it was a flattering photo, she wouldn't have shown it to him otherwise.

Connor studied the photo of the petite blonde and bustier brunette. They looked good together and Connor wondered if Chelsea was trying to tell him something. Surely she wasn't a lesbian, he thought to himself.

"You both look really pretty," he said with genuine interest then reached into the plastic shopping bag he'd been carrying.

"I hope you don't mind me doing this," he told Chelsea, "but yesterday I saw your phone screen was cracked and well, frankly the phone looks like it's come out of the ark."

Connor placed the box containing a new I-phone 15 pro on the table and slid it over.

Chelsea was a bit lost for words for a moment.

"That's really kind of you Connor, but I can't accept it. These things cost a fortune and I hardly know you."

"I didn't buy a subscription for it if that helps. I thought that might be a bit creepy."

Chelsea had to laugh at his comment. But before she had a chance to refuse a second time he began telling her about himself.

"My name is Connor Patterson. I'm thirty five, I'm divorced."

Presley had been right after all, Chelsea thought.

"Is that why you live on your boat?" she interrupted

"No, not at all," he laughed. "Why would you think that?"

"Actually it was Presley who thought that. She thought your wife had taken you for everything in the divorce."

Connor had to laugh at that.

"Let me explain," he began as the waitress brought their nachos over. "After I finished at Stamford I set up a company developing software. Our biggest product was an instant messaging app. It was a case of being in the right place at the right time and it grew and grew. Eventually Zuckerberg came along and bought us."

Chelsea couldn't resist nachos and she stuffed her face with them as Connor told his story.

"After that I changed direction and built a crypto currency exchange. It was an even bigger success than the messaging app and the money rolled in. I felt like a rock star. It was parties, private jets, the works. I married an actress. Things couldn't have been better."

Chelsea wanted to ask if she'd heard of the actress but didn't want to spoil Connor's flow.

"But after a year my wife left me. I took my eye off the ball and before I knew it I was ousted as CEO of the company I'd created. I guess I had a bit of a breakdown. So I bought a boat and sailed the pacific for a year and half. And here I am today."

"I'm sorry. It must be terrible to lose everything."

"Maybe it was what needed to happen."

"That's very philosophical. But I can't accept the phone Connor, can you get your money back?"

"I guess."

"Good."

When the burgers arrived, Chelsea got Connor to talk about his time sailing. The pacific islands sounded so exotic and she was curious what life on a boat must be like.

"I'll take you sailing on it if you like. How about tomorrow?"

"I said I'd go out with Presley tomorrow, I'm afraid,"

"Well any time you're free."

"Thanks, I'd like that," Presley said enthusiastically. "So what do you think you'll do now?"

"I'm not sure," Connor said. "I need to see what happens I guess."

"Well if you need any help, let me know."

Chelsea liked Connor, despite the fact he appeared to be a bit of a fixer upper. Besides he had a great body and he was really sweet too.

Neither of them had dessert. In fact Chelsea had eaten so many nachos she hardly had room for the burger.

"Do you fancy going for a walk and maybe catching a beer somewhere?" Connor asked.

"As long as we can go see the Sea Lions first."

Connor paid up and they strolled along the pier to where the Sea Lions lay on the pontoons. It was getting dark and they were even less active than in the daytime now. There was still the occasional snort from them and Chelsea chuckled when they did.

"I think I could be a Sea Lion," she told Connor. "Free accommodation, plenty of fish."

"You're too pretty," Connor replied a bit self-consciously.

Chelsea looked at Connor cheekily.

"You think?" she said trying to mimic a Sea Lion.

"Definitely not a Sea Lion," Connor told her laughing.

Chelsea thought for a moment then chanced it.

"You can kiss me if you want," she told him.

Connor didn't wait to be asked twice. He bent down and putting his hands on her hips he moved in for a kiss. Chelsea responded by reaching around and running her hands over his muscular back. When their lips connected it was like fireworks going off and they ate each other's mouths furiously. She felt Connor's hand reach under her dress and cup her cheek pulling her onto him.

"Can we go back to your boat," she asked.

"I've got a better idea," he replied.

Chapter 5

There was a sense of precarious excitement as the taxi made its way to Connor's apartment, with neither of them wanting to spoil the moment. When they arrived, Connor used his key card to access the elevator and the two of them entered the lift. No sooner were they alone in it than they had their tongues down each other's throats. Connor put his hand under Chelsea's dress again but this time he had a different target in mind and Chelsea opened her legs to let him feel her warmth.

Once inside the apartment they headed straight for the master bedroom and wasted no time tearing each other's clothes off. Connor laid the naked Chelsea down on the bed then bent down beneath her thighs to tongue her clitoris.

"You don't need to do that," Chelsea told him. "I'm ready for you now."

"I do need to," Connor told her. "It's been a while for me and I'm pretty sure that once I'm inside you it's not going to be a marathon session," he said apologetically. "So let me bring you off first."

"That's so sweet of you," Chelsea replied. "And since you asked so nicely you have my permission to make me cum," she giggled.

Connor was in fact a bit of an expert when it came to oral and he used it to extend the duration of their lovemaking. He brought Chelsea to the edge of orgasm several times only to deny her the final pleasure. Only when she was screaming at him to let her cum did he finally tip her over the edge and she clawed at the sheets while he held her legs apart.

"Fucking hell," was all Chelsea could manage as she recovered, "you can do that again," she told Connor. "But not now."

She pulled Connor towards her and he moved his body up the bed until their hips were aligned. Connor bent down and kissed her and for a while the two of them just enjoyed each other's mouths.

"I want you inside me," Chelsea whispered. "I don't care how long you last. Just concentrate on enjoying yourself. There's nothing to prove."

Connor lined his cock up then pushed carefully into Chelsea's vagina. She was moist and lubricated but he couldn't believe how tight she felt. It was like her body was wrapping itself around his cock. Chelsea clamped her legs around his waist and giggled her signature giggle again. Connor's cock was a good size without being huge, kind of in proportion with the rest of him really, and he filled her up nicely. With the endorphins already swimming around her body from the recent orgasm Chelsea was loved up and just wanted to make Connor happy.

"That feels so good," she purred.

Connor waited a while before allowing his hips to rise and fall on her. He knew the longer he lasted in her, the better his chances of delaying his orgasm were, but then Chelsea began pushing her hips upward forcing his cock deeper into her. He was helpless to do anything about it and so he began to pump her vigorously.

"Cum for me baby," Chelsea whispered in his ear and within a couple of thrusts he'd obliged.

Chelsea felt Connor's cock go into spasm and gripped onto him with her legs, just in case he tried to pull out then the two of them lay there, coupled.

"You did wear a condom, didn't you?" Chelsea asked, seeking confirmation.

"Err, no," Connor replied. "I err..."

"Oh god, oh god. I'm not on the pill," Chelsea said panicking. "What are we going to do? Quick, get off me."

Connor jumped off her like a man who'd been electrocuted but Chelsea just lay there chuckling.

"You should see your face," she laughed.

Connor realised he'd been had and saw the funny side of it.

"I suppose you think that's funny," he laughed.

"I'm sorry, I couldn't resist it," Chelsea told him. Then getting serious, she said, "As a way of saying sorry I'll let you kiss me again if you like, and maybe hold me too."

Not all guys were into cuddling afterwards, which was frustrating for Chelsea because she was. Connor slipped his arm under her neck and turned onto his side then stroked her body as he kissed her. He could almost hear her purring as he did.

"That was nice," Chelsea told him when they came up for air.

"It was and thank you," Connor told her.

"You know what would make it even better though?"

"No."

"Beer," she declared. "I'm parched, do you have any?"

"I don't know," Connor admitted, not having checked the fridge before. "I'll go look."

Connor got up and walked towards the door.

"So whose apartment is this?" Chelsea asked before he disappeared.

"It's mine," he confirmed. "I moved in yesterday."

"I thought you said you were broke?"

"I said I lost control of my company. It's not the same thing."

Connor could see that Chelsea was a bit confused.

"When I lost control a consortium of investors bought me out."

"Did you get a fair price?"

"I think so."

"So you're not broke and living on your boat because your wife got the house in the divorce."

"No. Why would you think that?"

"It doesn't matter."

Connor went off to look for beer and Chelsea took a trip to the bathroom to freshen up. When she returned Connor wasn't there and so she took a walk to see if he needed help. She found him in the open plan kitchen cum diner cum lounge searching through the cupboards. But what caught her attention was the view of the bay from the panoramic window.

"It's beautiful," she said.

Connor was too busy trying to find beer to notice the petite, perfectly formed woman enter the room but when she spoke he looked up and for a moment he was totally captivated by her naked form. He walked over to Chelsea and hugged her from behind and they both stared out at the bay.

"I'm sorry, I can't find any beer," he said.

Chelsea was conscious that maybe this was Connor's way of saying it was time to leave.

"Maybe I should be going then," she offered.

"I was really hoping you'd stay," Connor said hopefully.

Chelsea turned to face him and gave him a hug.

"I was really hoping you'd ask me to," she told him.

Chapter 6

Connor woke up to nothing but the gentle sound of Chelsea's breathing. On the boat there'd almost always been some sort of noise. The sound of wind, or rain, or waves slapping against the hull. But now there was nothing but calm. Chelsea was a hugger and she'd draped her arm over him. Connor wanted to touch her, run his hands over her body, but she looked so peaceful lying there.

They'd had sex again after she'd agreed to stay. This time he'd lasted longer. He hoped he hadn't disappointed. Chelsea had been both enthusiastic and athletic. That was probably the best way to describe her. But she'd fucked with such energy that, afterwards, they'd both collapsed on the bed panting. At some point they must have drifted off to sleep but Connor couldn't quite remember when.

When Chelsea began to stir it took her a moment to realise where she was. Then she remembered.

"Good morning," she began with her trademark giggle.

"Hi. Would you like a coffee?"

"I'd like a kiss first. If that's ok?"

It was a way of telling if Connor still wanted her there, but from the way he kissed and touched her Chelsea didn't feel as though she was overstaying her welcome.

"Now I'd like that coffee," she told him.

"Coming right up."

While Connor was gone Chelsea went to the bathroom and freshened up. After a quick wash she put some toothpaste on her finger and rubbed it over her teeth. Then she got back into bed. When Connor returned he placed the coffees on the nightstand and climbed back in alongside her. Chelsea rewarded him with another hug.

"Why don't you come out sailing with me today?" he asked. "I have to move my boat down the coast. They won't let you stay in the marina here very long."

"Where are you going?"

"Monterey direction. There's a marina not so far away."

"How will you get back?"

"Erm... I have a house down there. I was hoping we could check it out then come back tomorrow."

"I'd love to Connor. This isn't a brush off but I said I'd go out with Presley this evening."

"We could meet her in Monterey. I could get a car to pick her up and we could meet her somewhere this afternoon. Then we could all have a night out down there."

Chelsea thought about things for a moment.

Chelsea reached for her phone on the nightstand and 'Whatsapp'd' Presley, who almost immediately video called her back.

"Where are you, you 'Stop-out'?" was the first thing Presley said.

"I'll explain later but how do you fancy meeting in Monterey later."

"It sounds fine but if you remember I don't have a car."

"Connor says he'll send one for you."

"Who's Connor?"

Chelsea tilted the phone to show Connor who was lying in bed.

"Oooh cute," Presley responded, "but you have some explaining to do."

"I will. I promise. So you'll come?"

"Duh. Of course."

"I'll text you the details. Oh and can you pack an overnight bag for both of us. See you later. Love you."

"Love you too."

Chelsea turned to Connor and said, "Done. I'm yours for the day." Then looking at her phone she said, "I couldn't rethink my answer about your offer of a new phone could I?"

"Too late," Connor replied. "I gave it to the waitress last night"

"You gave a brand new phone to the waitress."

"She looked like she could do with it and I didn't want to carry it around in that bag anymore."

"Oh, right."

"I could buy you another one if you liked."

"No, it's ok. I had my chance and I blew it," Chelsea laughed.

"I can afford it," Connor tried to convince her.

"I don't want you wasting your money."

Connor was having some difficulty persuading Chelsea that he was creditworthy. He didn't want to be the guy that said. "Do you know what I'm worth?" but at the same time he felt he needed to be straight with her.

"Look," he began. "I need to be honest with you."

Alarm bells started ringing in Chelsea's head. Was he married? Was the whole thing about living on a boat a story he'd made up?

"Honesty's good," she said.

"I sold my stake in the crypto trading company for just short of a billion dollars."

"Fuck a duck. Really?"

"Yes. Google me, it's all there. Connor Patterson, the rise and the fall."

Chelsea was shocked but she sensed that Connor was embarrassed and so she tried to make a joke of it.

"I liked you when you were poor, I can get used to you being rich I guess."

"You can ask me anything you want and I'll try to give you an honest answer. But the point I'm trying to make is that I can afford to get you a new phone. If you'd like me to that is."

"I would," Chelsea said positively. "Thank you."

"First thing Monday, but we'd better get moving now," he told her. "We've got a full day's sailing ahead of us."

"I don't really have the right clothes though. All I've got is the ones from last night," Chelsea pointed out.

"Don't worry there's a shop at the marina."

Connor and Chelsea made their way to the Marina in a cab, stopping off at a chandlery on the way. It was the sort of place that sold everything for boats, from a Sonar system to a plunger to unblock a toilet. It also sold sailing clothes and they got Chelsea kitted up with some weatherproof gear and a lifejacket.

When they arrived at the Marina, Chelsea was surprised at how small the boat Connor had been living on was. Connor had bought the 35 foot Junneau 3300 Sunfast a couple of years before. It had been new then but now it was looking a bit tired.

"Excuse the mess," he said, rather embarrassed as they descended into the cabin area.

Chelsea noticed the pizza box and the empty whisky bottle on the table and the plates piled high in the sink.

"Why don't you do what you need to do and I'll tidy up down here?" she suggested.

"Are you sure?" Connor asked.

"Yes, but I want a kiss first," she told him.

Connor put his arms around Chelsea and they kissed.

"Thank you for my sexy outfit," Chelsea said afterwards striking a pose in her sailing gear. "You know most guys would have gone for lingerie," she laughed.

"Next time, I promise," he laughed.

It took about half an hour to get the boat ready, which was more than enough time for Chelsea to tidy up below deck then they motored out of the marina. Sailing under the Golden Gate Bridge was a special moment and in no time at all they were out into the waters of the pacific with the big sail up. Chelsea was surprised how fast they seemed to be going. The feeling of speed was exhilarating and with the spray from the boat catching her she appreciated the sailing gear Connor had brought her.

Connor showed her how to steer the boat and trim the sails. He was surprised how quickly she caught on and so he left her to it and disappeared below to make them both a coffee. Chelsea felt the thrill of piloting the boat and loved the experience of being in control.

"What do you think?" Connor asked when he emerged with coffees. "Are you enjoying it?"

"It's fantastic," Chelsea enthused. "Thank you for bringing me."

It took eight hours of hard sailing to get to Monterey and Connor loved how Chelsea seemed to enjoy every minute. He let her do most of the skippering and only took over when they entered the harbour under power from the inboard motor. Once they'd been directed to their birth, Connor tied up and they stepped off.