A Fresh Start: Romance

Story Info
Things move faster than expected.
23.5k words
4.8
7.4k
7

Part 2 of the 3 part series

Updated 03/24/2024
Created 12/17/2023
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
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

Preamble

Apologies, it has taken me a lot longer to write this follow up to 'A Fresh Start' than I had intended. I'd planned on writing ten thousand words for this episode but found myself writing more than double that in the end.

Anyway, sorry for the delay and I hope that you enjoy it.

Chapter 1

Connor Patterson stood in the reception area of the upmarket gym, waiting for Chelsea to finish her shift. He hadn't seen her since he'd dropped her and Presley back at their apartment on Sunday night. It was Wednesday now.

Connor hadn't been short of things to occupy his time in the intervening period. If you spend eighteen months sailing around the pacific then, when you come back, there are inevitably going to be things to catch up on. But he'd found himself struggling to make meaningful progress on anything.

On Monday he'd risen early, gone out for a run then sat at his desk and tried to make some sort of plan of action. After an hour, he'd got nowhere.

Before the divorce Connor had been good at stuff like this. He'd made a small fortune developing a hugely successful messaging app and then an even bigger one building a Crypto exchange. But, when Sophie divorced him, he'd taken his eye off the ball. Before he knew it, he'd been kicked off the board of the company he'd created and forced to relinquish his share in it, albeit for an eye watering amount of money.

Now, almost two years later, Connor found himself staring out over the San Francisco Bay from the luxury of his penthouse apartment. Cash rich, time rich, but with no idea what to do next.

Of course, it didn't help that he couldn't get Chelsea off his mind. Her petite figure and pert little gym-bunny body had captivated him. She had this slightly hippy naivety to her and the fact that she'd liked him even before she knew how wealthy he was had been a breath of fresh air.

Then there'd been the threesome in Pebble Beach that weekend with her best friend Presley. It had been natural, uncomplicated and fun. Of course, he'd had similar experiences with Sophie when he'd been married, but it was something he'd been expecting to give up after the divorce. After all, not that many people were into swinging, were they?

When the maid arrived to clean the apartment, Connor gave up on trying to come up with a plan and decided to walk from his apartment to the Apple store, to make good on a promise to replace Chelsea's old iPhone 5.

Once inside the store, Connor couldn't help himself however. In addition to the iPhone 15 ProMax he ended up buying Chelsea a Macbook Pro, an iPad Pro, an Apple Watch and some Air Pods. As he walked back to the apartment he hoped he hadn't gone over the top.

That evening Connor had phoned his parents. Apart from his lawyer and friend, Mike Frankle, they'd been the only people he'd kept in contact with while he'd been sailing. He promised to visit them soon in Philadelphia. It had been over eighteen months since he'd last seen them.

Afterwards, he thought about calling Sophie to tell her he was back, but decided against it. They'd parted amicably enough but he needed to move on. So he texted Chelsea instead, telling her how he was looking forward to seeing her on Wednesday. Five minutes later she texted him back saying she was looking forward to seeing him too and ending her text with a little heart emoji. Connor went to bed with an erection that night thinking about her.

***

Tuesday was pretty much a repeat of Monday. Up early, run, shower, dress, coffee, breakfast, sit in front of the lap-top, stare out of the window then give up. This time Connor opted to go for a drive. He hadn't driven a car in eighteen months and the brand new Ferrari SF90 Stradale in the basement was begging to be taken out. Three hours later, just short of Anchor Bay on Highway One he stopped to admire the view.

And then he couldn't help himself. Connor picked up the phone and called Sophie. She didn't answer but he left a short voicemail for her. Almost immediately, she called back.

"Hi. I didn't know it was you," Sophie began.

"New phone," Connor explained.

"Are you ok?" she asked.

"I'm fine. Just called to say I'm back on dry land."

"For good?"

"I think so. Got back last week."

"I'm glad. Where are you?"

"San Francisco."

"L.A.'s only a few hours away. I'm finishing up a miniseries for Netflix at the moment. Why don't we meet up for dinner this weekend?"

"I don't think that's a good idea," Connor replied. "We'd probably end up fucking."

"Would that be such a bad thing?" Sophie asked cheekily.

"Yes and no," Connor admitted. "Besides I've kind of met someone."

"Do I know her?"

"No. She works in a gym."

"Oh," Sophie sounded surprised. "I always saw you with some hotshot lawyer or techie nerdling."

Connor laughed. In truth he'd probably thought the same.

"And what about you and this Jack Daniels guy?"

"That's over."

"Oh right. Sorry."

"Don't be. Let's just say he was a mean drunk. Anyway, I'm having an affair with my co-star at the moment, Lance Penning. He's just using me to get noticed, but with a body like his I don't mind."

"You haven't changed," Connor laughed.

"I guess I haven't," Sophie replied, "and that's why I was no good for you, Connor. You know that, don't you?"

"It's taken me a while, but yes."

"I'd still like to see you though. Bring your new girlfriend along. We could make up a foursome."

Connor wasn't sure what Sophie meant by a foursome but didn't press her on it.

"I'll let you know," he replied. "Listen, I should be going. I've gone for a drive along the coast but I need to get back."

"Ok. It was nice talking to you, Connor. I'm serious about dinner this weekend, let me know."

***

On Wednesday, Connor gave up on planning and began calling old friends and colleagues. Most had taken his call, or called back fairly quickly and, by the end of the day, while he was no further forward with his life, he felt as if he had at least achieved something.

At about three he drove over to Chelsea's gym and waited in the reception area for her to finish her shift.

Chapter 2

Chelsea was excited about seeing Connor again, but nervous at the same time. They'd had a great weekend but she wondered if perhaps, after a few days contemplation, he was now regretting asking her to move in with him, even if it was only for a few days each week.

She walked into the gym's reception area carrying an oversized bag stuffed with clothes and other stay-over essentials. Chelsea prayed that Connor wasn't going to stand her up, or worse still, dump her in front of the girls at the Gym's reception.

As it turned out, she couldn't have been more wrong. Connor was waiting for her and gave her the biggest hug in front of everyone. The kind that left her in no doubt he hadn't lost interest.

"Hi," he told her afterwards. "Sorry about the public display of affection."

"Don't be," she said, kissing him full on the lips. "By tomorrow though, everyone at work is going to know about this. The girls on reception will make sure of that."

"Good," Connor replied then he admitted, "I guess I was a bit worried you might have changed your mind."

"I was too."

"Well I haven't," he said reassuringly.

"Me neither. Presley's away until Monday. So you've got me 'til then if that's ok?"

"That's great. I thought we could start with a bit of shopping, get you some stuff to make you feel more at home in the apartment. While you do that I need to buy a suit and a few more smart clothes. Then I thought we could grab a bite to eat somewhere."

"Sounds good," Chelsea replied enthusiastically.

As they left, Chelsea said goodbye to the girls on reception who smiled at her knowingly. Then she and Connor walked to the car park and got into his Range Rover. Once inside, the two of them kissed again but this time much more passionately.

Connor couldn't keep his hands off Chelsea and she wished she'd worn a dress or a short skirt for him. There was only so much fondling you could do in jeans. She thought about offering to suck him off, but the size of the Range Rover's centre console made it almost impossible. There was no rush Chelsea rationalised. There would be plenty of time for sex later. For now, she was just relieved to know that Connor still wanted her.

They drove the short distance to one of the high end department stores off Union Square and, once inside, Connor headed for the management suite. Chelsea waited for him as he spoke to someone about setting up an account and when he emerged he was accompanied by a smartly dressed young redheaded woman, not much older than Chelsea.

"Chelsea, this is Grace," Connor said by way of an introduction.

"I'll be your Personal Shopper, if that's ok?" Grace added.

"I thought Grace might be better at helping you choose stuff than me and I don't want to bore you while I try on suits," Connor explained.

"I've never had a Personal Shopper before," Chelsea offered.

"Don't worry. I'll take you through the process," Grace told her. "If you're ready, why don't we start by taking some measurements?"

"But I just need a few toiletries and things."

Grace looked at Connor, as if there had been some confusion.

"I thought you might want to keep some clothes in the apartment as well," Connor explained.

"Can I talk to you alone, Connor?" Chelsea asked, embarrassed.

"I'll give you a moment," Grace said politely.

"Connor, I can't afford to shop here," Chelsea explained after Grace had walked away.

"I'm sorry, I should have asked first. But I was afraid you'd turn me down," Connor admitted. "I set up an account for you. You can shop here whenever you want, and you don't have to worry about the tab."

"That's very generous, but you shouldn't have," Chelsea told him.

Connor thought for a moment.

"I don't want you to think I'm trying to buy your affection Chelsea, but..."

"And I don't want you to think I'm some sort of gold digger who's only in it for the money," Chelsea interrupted.

"Honestly, that's the last thing I think," Connor tried to reassure her. He stopped for a moment then continued. "But, I can't shop here if my girlfriend shops at Walmart. So, one of us is going to have to change. And I really don't want to buy my clothes at Walmart."

Connor's comment made Chelsea laugh.

"I like it when you call me your girlfriend," she giggled.

"Well get used to it," he replied giving her a kiss. "Besides, it's just some clothes and toiletries. Let me spoil you just a bit. Please?"

"Ok. I'll try to. Thank you."

"Grace, I think you can come back now," Connor said to the young woman apologetically.

"Let's get you measured," Grace told Chelsea reassuringly.

Grace led Chelsea into a fitting room while Connor went off in search of suits.

"So it's your first time with a personal shopper?" Grace asked as she found a tape measure.

"Yes," Chelsea responded. "Connor and I haven't been dating long and to be honest before I met him I was more of a Walmart girl."

"There's nothing wrong with that," Grace said, putting Chelsea at ease. "Now, if you're happy, it's best to take measurements in just your bra and briefs," Grace explained.

"Ah. Ok," Chelsea said and began to undress

"Your boyfriend must like you a lot though," Grace added as she waited.

"Why do you say that?"

"His instructions were that you're to have whatever you want, in any department, regardless of cost. And believe me, they sell some pretty expensive things here."

"I didn't know that," Chelsea said, concerned. "I don't want people thinking I'm a gold digger."

"Fuck what people think," Grace said with a forthrightness that made Chelsea giggle. "Haters gonna hate."

Chelsea stood in front of Grace in a pair of cotton bra and briefs that displayed the name Calvin Klein on them. They were fakes of course and not particularly good ones at that, but they suited Chelsea's slim figure. Grace moved behind Chelsea and began by measuring the circumference of her rib-cage.

"Oooh," Chelsea exclaimed as the cold tape made contact with her skin.

"Sorry. Is it cold?" Grace asked.

"A little. It's not too bad though."

Grace then placed the measuring tape around Chelsea's bust. It teased her nipples and Chelsea felt them involuntarily harden, something the cotton bra did little to disguise.

"He's quite cute your guy, isn't he," Grace added as she slipped the tape around Chelsea's waist. She rested a hand on Chelsea's hip and, at the same time, Chelsea felt Grace's warm breath on her neck.

"I think so," Chelsea said, slightly aroused at being almost naked in such close proximity to an attractive young woman.

"It's easy to see what he sees in you though," Grace told her as she moved the tape to down measure Chelsea's hips.

Grace took what Chelsea had assumed would be the final measurement then surprised her by saying, "Now if you just open your legs a touch, I'll measure your inseam."

Grace moved from behind Chelsea and knelt in front of her. She held one hand against the top of Chelsea's thigh and ran the tape along the inside of her leg. Chelsea couldn't be sure if it was deliberate or not but through her cotton panties she felt Grace brush her pussy lips with a hand. Chelsea felt a jolt of electricity pass through her at the touch and struggled not to let out a gasp.

It was over in a moment and soon Grace had moved on to noting Chelsea's height and shoe size, leaving Chelsea a bit bewildered by the whole experience.

"You can put your clothes back on now," Grace confirmed. "I have you at 5' 4", a very slender 32B-24-32 and a size five shoe. Does that sound about right?"

"I think so."

"Good. Now there's not going to be enough time to do everything today, but we can start with make-up and beauty and then next time you come in we can do the fun stuff like clothes and lingerie. I can go away and make some suggestions for things that might suit you if you want?"

"I'd like that," Chelsea giggled.

"Give me a couple of days," Grace added. "Now let's get you sorted for beauty products."

An hour and a half later, Chelsea was trying on make-up when Connor caught up with her. Grace and Chelsea were getting on like a house on fire and Grace had managed to overcome Chelsea's reticence for spending Connor's money, a fact borne out by the number of items Chelsea had committed to.

"How's it going?" he asked.

"Very well, I think," Grace responded, answering for Chelsea.

"Did you find any suits?" Chelsea asked Connor.

"Yep. They need some alterations but they'll be ready in a couple of days," Connor replied. "So, are you ready to eat? I think the store's shutting in ten minutes."

Chelsea looked at Grace for confirmation.

"We've made a good start," Grace confirmed. "I'll get these things sent over to your apartment this evening and I'll call you in a couple of days. This is my card in case you think of anything you particularly need."

"Thank you so much," Chelsea told Grace. "I've had a great time."

"Well I am here to help you spend money," Grace laughed.

The two girls hugged goodbye and Chelsea could have sworn she heard Grace let out a little sigh as they did. Grace then embraced Connor slightly more formally before leaving.

Chapter 3

Connor and Chelsea found a steak restaurant not far from Union Square. It wasn't very busy, but then it was only six thirty on a Wednesday evening. They both ordered the rib eye and Connor had a beer while Chelsea just ordered water. Being on her feet all day meant that Chelsea could eat what she wanted without fear of putting an ounce of weight on but she tried not to drink on weekdays. It would have been easy to make an exception for Connor but she tried to be good.

Chelsea was beginning to regret agreeing to go for food, though. She'd have preferred to have gone back to the apartment and had sex. The experience with Grace had left her horny as hell.

"How did it go with Grace?" Connor asked innocently, referring to the shopping. "Did you get everything you needed?"

"I did, thank you. It was just make-up and toiletries today but Grace took my measurements and she's going to suggest some outfits she thinks might suit me. So I'll have to go back another time and try some on. If that's ok with you?" Chelsea asked. "You will tell me if I'm taking liberties though, won't you?"

"I will, but you're not," Connor reassured her then asked, "So does 'outfits' include lingerie?"

"I guess it could do," Chelsea replied coyly. "Would you'd like it to?"

"Very much."

"Well, since you're paying, I'll make sure it does then," Chelsea giggled. "The whole measuring process was a bit intimate though."

"I guess they need a good baseline to work from."

"True, but you should have seen the way Grace touched me."

"Maybe she fancies you," Connor suggested conspiratorially. "I could see why she might."

"It did make me wonder."

"Well there's one way to find out."

"Are you serious?"

"Well you did say I was going to have to share you," Connor laughed. He wondered if he might have overstepped the mark though. "But I guess we should have a talk about what this relationship of ours is going to look like first."

Chelsea knew they needed to have a discussion but she wasn't quite sure how to respond. She liked Connor and she didn't want to scare him off. At the same time she knew that hiding her true self from him wasn't going to help either of them in the long run. She looked around the restaurant to see if they could be overheard.

"Ok," she said slightly nervously. "But you go first."

Connor pressed his fingers together as he thought about what he wanted to say.

"I don't have a problem sharing you. I'm not the jealous sort. However there is a 'BUT'," Connor emphasized.

"Which is?"

"I'm looking for a girlfriend, not a fuck-buddy. I don't want a relationship where we spend more time with other people than we do with each other."

"Is that why you split up with Sophie?" Chelsea asked

"I guess it was part of the reason."

"I'm not looking for a fuck-buddy either," Chelsea said reassuringly. "I want to be a proper girlfriend. But in return I expect full girlfriend status. I don't just want to be your little secret."

"Agreed. But that works both ways."

"Don't worry, you have official boyfriend status," Chelsea said reassuringly. "But you know I can't abandon Presley though."

"I don't expect you to."

"Presley told you I was bit of a hippy chick, didn't she?" Chelsea clarified.

"She did."

"She's right. I kind of believe in free love, if it feels right," Chelsea confirmed. "I thrive when I feel secure. But I've been relying on Presley a bit too much for that recently."

"I don't think she sees it as a burden but I'm hoping she might let me take some of the weight off her shoulders?"

"She can't wait to get rid of me... besides, I know she's already given you her blessing."

Chelsea looked down at her empty plate. She'd demolished the steak and could have easily taken on dessert, but she had other things on her mind.

"Connor, I don't think I can hold out much longer. Please can we go back and have sex now," Chelsea added, sounding slightly desperate.

Chapter 4

Chelsea's alarm went off five forty five. She knew she needed to get up immediately. If she didn't, she'd still have been in bed, snuggled up to Connor two hours later. She jumped out of bed and took a quick shower. Putting her gym gear on under some sweat pants and a top she emerged from the bathroom ready to hit the road.

Connor rubbed his eyes and looked at her from the bed.

"Do you have to go?" he asked.