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The Business Trip Date

"James invites his sister Chelsea out as a date on an important business meeting"

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Author's Notes

"Finally, my sequel to my original Chelsea/James story! I hope you enjoy! And of course, if you missed the first story, it should be listed in the series dropdown. I have some thoughts for more stories, but if anyone has good ideas of where to take this next, feel free to suggest in the comments!"

Chelsea stood in the kitchen of her and her brother James’ apartment chopping vegetables for dinner. Dinner would often be something they both worked on, unless one of them was making one of their specialties, but tonight James was late coming home, something that had recently been happening a bit more often.

Ever since their night a few months prior, things had seemed to be a bit - different - between the two. Not awkward or bad necessarily, just different. The siblings had always had a pretty good relationship with each other, but it had seemed to Chelsea that it had, perhaps, stepped up to the next level. They just seemed to spend more time together than even what was usual.

Maybe it was because they were both single and hadn’t found anyone new to date, so they didn’t have anything else better to do. But they still had other friends, and Chelsea found that they had seemingly started hanging out together with the other’s friends a bit more as well.

Chelsea didn’t mind hanging out with James and his friends, or having James hang out with her friends. Her friends had even joked with her that it was too bad James was her brother since she already had a place alone with a hot guy with money otherwise. Chelsea would try to just laugh off these jokes, of course not revealing that, while it was still unspoken even between Chelsea and James, there may be a bit more between the two than just being siblings.

She would occasionally find herself fingering herself while lying in bed, thinking about that night, and fantasizing about more. But of course, that wasn’t possible, she believed. At the bare minimum, what would their friends say if they found out, much less the rest of society? No, they had their night of passion, and while it was enjoyable, it wasn’t something they could indulge in further. Besides, the pair seemed to have found a new status quo that both were satisfied with.

Chelsea was just finishing with the dinner prep when James almost burst through the door, out of breath, which Chelsea immediately noticed. “Is something wrong?” she asked as she set down the kitchen tools she had been using to mix and divide the evening’s ingredients.

“Huh? Oh, no. Just…an interesting day at work is all,” James remarked, still catching his breath and pulling his tie loose as he started to walk back towards his room to change. James was a part of the sales team at some software company. Chelsea could never really get her head around exactly what the software did, but it was something that usually sold for a lot of money to various large businesses. The commissions on these sales were a big reason why the pair was doing well for themselves.

“Oh? Enough to make you rush home?” Chelsea asked with a little laugh as she started turning on the stove to actually cook dinner now that James has home.

“Just a bit excited and…” he took a pause to consider the word, “anxious?” He still didn’t seem sure if it was exactly the correct word but it seemed close enough from how he said it. “Basically, we have a big client up in Boston that is interested in buying, and it’s a big buy. Maybe the biggest one in years for the company. Big possible commission. Big businesses for the company if we get it. And they want me to go up to do a business dinner with the buyer this weekend.”

Chelsea felt a sense of pride in James at this opportunity, but also started to share a bit in the anxiety. This seemed like one of those deals where if it goes well, James could get cut a large check - maybe even get promoted - but if it fell through, he would probably be the fall guy for the company losing who knows how much money. She didn’t know the intricacies of his job, but she knew enough to know just how high-stakes this sounded.

“Boston huh? What kind of dinner?” she asked curiously.

“I looked the place up after I got off work. Basically a ‘if you have to ask, it’s too expensive’ type of place. Of course, the company will pay so I don’t have to worry about that. I’m gonna need to break out my good suit for this one. Boss also seemed to imply I might want to bring a date for this one. Client will probably be with his wife so for balance, you know…”  James trailed off, seemingly not really sure there was much to add.

“Oh, I see. Well, good luck!” Chelsea felt a pang when he mentioned a date. But she couldn’t ask him if it could be her. Would bringing your sister along even count as a date?

James then emerged from his bedroom, wearing a t-shirt and jeans, and walked back into the kitchen. “I was thinking. All the women I know at work already have boyfriends. I don’t know if any of your friends might be interested, or…” he gave a bit of a pause, “if you might be.”

Chelsea felt a bit of a rush run through her when he added the last part. “I mean, Janice is probably available…” she gave a slight pause. “As for me, do you really think that would work? I mean, be appropriate?”

James gave a slight shrug. “It’s just a dinner out. Just a little more formal than usual. I’m sure we’ll be talking business so you may be a bit bored. Maybe you can split off and talk with his wife while we do that, I dunno. I know you have that dress, so that would probably work.”

Ah yes, the black dress she had worn that night. She hadn’t worn it since - she had never had a reason to, but this was the closest either of them had come to actually verbally acknowledging what had happened since that night.

“Yeah, I guess that could work. I assume your company is going to pay for travel?” Her work on dinner had completely stopped at this point. She had a slight knot in her stomach and didn’t know why. It was just a business dinner, nothing more.

“Yeah, train up Saturday morning, dinner that evening, spend the night at the Omni Parker House, and then travel back by train Sunday. Uber to the hotel. Walk to the restaurant since it is only a couple blocks away.”

It seemed this was a very tightly planned trip. The company wasn’t leaving much up to chance, it seemed to Chelsea. “It doesn’t seem like there will be much time to do much else. But I guess it is a business trip.” She started slowly preparing dinner again.

James gave another slight shrug. “Maybe we could find something to do after dinner, although we might be ready to just collapse after that since that is where all the action is taking place. At least we’ll get to see a little bit of Boston, anyway.”

“Yeah…” Chelsea wasn’t sure why she felt a bit disappointed. This was a big opportunity for James, but she was hoping there might be more time to do something other than travel, meet, and then travel back. “Sure, why not I guess. It’s been a while since we’ve been on a trip. Even if this one is pretty short. At least we don’t have to pay for it.”

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The trip to Boston was pretty uneventful. The pair had only brought along a handful of carry-on items for the eight-hour train ride in business class, and then took an Uber to their hotel once they arrived. They didn’t have much time to waste as they only had a couple hours before their scheduled dinner.

Luckily for the pair, they had a reservation for a room with two double beds, and Chelsea went to work immediately getting ready once they checked in and got to their room. She had to shower and put makeup on, as well as put finishing touches on her hair within the next couple of hours since they still had to walk to the restaurant. It was supposed to be only a five-minute walk, but they still wanted to give themselves plenty of lead time, just in case.

“How do I look?” James asked, decked out in a business suit and tie, a few minutes before the intended time to leave.

“You look really sharp,” Chelsea responded with a smile as she was putting on a necklace and earrings, the final touches of her preparation.

“Well, you look beautiful as well, Chelsea,” James responded, causing her to blush slightly. “Well, I guess we should head out then.” The pair then made their way down to the street and towards the restaurant, which was the No.9 Park. They arrived nearly at the same time as the business associate and his wife.

“Mr. Jennings, I presume?” James greeted the associate, offering his hand to shake.

“Oh, it’s Cory, please. And you are James, I'm guessing?” the associate responded in greeting, shaking James’ hand.

“Ah, yes, that’s right. And this is my date for the evening, Chelsea,” James remarked, stepping aside and motioning towards Chelsea after shaking Cory’s hand. Chelsea stepped forward and offered her hand.

Ah, such a beautiful lady, and such a beautiful name to go along with it. Pleased to meet you, Chelsea. Cory then took her hand and raised it up and kissed it in greeting. “And this is my wife, Janice,” Cory added, stepping aside and introducing his wife, a woman in a dark red dress who was beautiful in her own right, probably in her late forties or early fifties.

“Madame,” James, responded, returning the courtesy and kissing her hand.

“Such a pleasure, James,” she responded with a smile. “Chelsea, a pleasure to meet you as well!” Janice then moved in and gave Chelsea a hug, which caught Chelsea a bit by surprise, but she quickly reciprocated.

“Anyway, let us get to our table,” Cory added once introductions were complete.

Chelsea felt that the restaurant was certainly…cozy. For some reason, she figured for a place that was high end there would be more room between tables, but this was also in historic downtown Boston, so she probably should have expected something a bit more cramped. All four members ended up just getting the chef’s tasting menu, which was a seven-course meal that Chelsea felt pretty sure she wasn’t going to finish, even if each individual course was small. She felt that the wine pairing that came with it was excellent, however, although she tried not to drink too much.

James and Cory mostly discussed what their respective businesses did, not getting into the real meat of the negotiations during dinner, while Chelsea and Janice largely listened, although occasionally they would talk about what they did as well. James and Chelsea neither mentioned that they were siblings or lived together, just that they were good friends - and also not really dating. Chelsea was just a convenient date that had graciously accepted the invitation.

Finally, the food portion of the dinner was complete, and Chelsea felt like she might burst. But it was also time for Cory and James to get down to real business.

“Chelsea, wish to join me at the bar?” Janice leaned over and asked in her ear.

“Oh, uh, yeah, sure…” Chelsea responded, caught a bit off guard.

“Excellent,” she replied before standing up. “Honey, I believe us ladies will take a sit at the bar while you two work things out,” she then remarked to her husband. Chelsea then followed Janice in the quite short walk over to the bar.

“I’ve been to enough of these that I know that I’m going to be bored to tears during their negotiations. I’m much more interested in learning more about you, Chelsea,” Janice remarked once they got situated. “Oh, and two l’azureens,” she added to the bartender.

“I’m not really sure what to say…” Chelsea sheepishly responded as the bartender whipped up and served two cocktails with an almost smokey color to them. “I’m just a girl trying to make her way through the world.”

“Hmm, and what about James? He seems like a nice man. Nice enough to ask you to come along. Nice enough for you to say yes?” Janice asked with a bit of a smirk on her face. "Nice enough that I can tell you keep giving him...those sort of looks?"

“He’s just a friend. Really.” Chelsea tried to brush the insinuation off.

“You know, I used to be young myself,” Janice said with a bit of a chuckle, “and I know that look when people make it. You two are crazy for each other. Maybe you should tell him that.”

Chelsea let out a sigh. “It’s not that easy. Things are…complicated.”

Janice took a sip of her cocktail, set it down, then put her hand on top of Chelsea’s. “It may not seem apparent now, but things used to be ‘complicated’ between Cory and I. I was the daughter of a wealthy family and he was the son of a handyman who just happened to work in a store I often frequented. If I’d listened to anyone who was interested enough to give their opinion, they would have said forget it. He’s below you. You’ll regret it. He’ll be too intimidated.”

She let out a slight sigh. “But you know what? I didn’t listen to any of them. I went in there one day as he was getting off his shift and dragged him to dinner right then and there. I was the best-dressed person in the dinky restaurant I had decided to take him too, because it wasn’t about impressing him. I took the opportunity that was given to me, because you never know when one will come again. And now look at us, happily married for almost thirty years. And never a regret. And while I would have loved him regardless, as you can see he’s made something of himself as well.”

Chelsea felt her stomach knot up. Was this really an opportunity? Her and James’ situation was certainly different than Cory and Janice’s, even if she faced disapproval for different reasons. But she had to admit that she and James were practically living as a de facto couple as it was, and were happy to do so. Neither seemed to have very much urgency when it came to moving out or finding someone to date. But there was still that awkwardness. Like they knew what they wanted to do but were holding themselves back from it because of what other people might think. But what about what they wanted? Wasn’t that important as well?

“Yeah, maybe. I’ll think about it I guess. It’s just…hard when you know the reaction might be negative. You ask if it’s worth it.” Chelsea mused, half to herself, before taking another sip of her cocktail.

“Dear, dear. True love is always worth it,” Janice responded before also taking another sip. Chelsea just slightly nodded and smiled.

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The pair chatted about life for another half hour, finishing their cocktails just before the two men stood up and shook hands, causing Chelsea to turn to look at them.

“I hope this is the start of a great partnership between our companies,” Cody remarked, appearing to conclude the negotiations.

“As do I,” James added, before ending the handshake, and slinking his way over to Chelsea.

The two men took their respective checks and paid, before stepping outside into the night. The group then started to exchange parting pleasantries.

“And Chelsea, remember what I said…” Janice appeared to conclude before the pair split away.

“I will,” she said with a slight smile, before leaning over and kissing James on the cheek, causing them both to blush.

“Good. Have an excellent night, you two,” she remarked before giving a wink and turning around to walk away with her husband.

“What was that about?” James asked as they started walking back to their hotel.

“What was what about?” Chelsea asked innocently.

“You know what,” James responded with a chuckle.

“Mmm, no, I really don’t,” Chelsea continued playing coy.

“Fine. I can’t wait to get this suit off. I feel like I’m about to die. Cory can press a hard bargain, but I believe what he hammed out will be acceptable to both of our companies.”

“I knew you could do it,” Chelsea happily responded, before giving him a slight hug.

The pair soon found themselves back in their hotel room. James quickly grabbed a change of clothes and slipped into the bathroom. It wasn’t long before Chelsea heard the shower turn on. “He must have really been sweaty if he’s taking another shower,” she thought to herself, as she slid her dress down to her waist.

She stood up and looked at the mirror, then turned sideways. Her nipples had been hard and erect since she had kissed James on the cheek. The idea of showing affection to him in front of someone else had excited her. She wondered if anyone had noticed. Probably not with her black dress and with it being dark out. But who knows, Janice was pretty observant.

She slipped her dress the rest of the way off, then tossed it over the back of a chair in the room, then slipped her panties off and tossed them on top of her dress. She turned back towards the mirror and bit her lip. She considered what Janice said and then decided.

She quietly slid into the bathroom, opening then closing the door quietly, a bit of steam spilling out into the main room in the process. She then tiptoed to the shower, and then quickly stepped in, causing James, whose back was facing her, to jump.

“Chelsea, what are you doing?” he asked, turning around, fumbling around with the loofah that he was holding.

However, before he could say anything else, she leaned into him and started kissing him. To her relief, he didn’t resist, and after a couple moments, he put his hands on her waist, and she put her arms around her back. She started kissing a bit more aggressively. Her breasts were pushing into his chest and she...

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