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The First Date

"Chelsea's double date with her brother doesn't end as she expected"

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Author's Notes

"Re-published with a couple of typo fixes and a series tag since a sequel is in progress. Enjoy!"

The only good thing about the dinner so far, Chelsea thought, was the food. Her date was boring. Her brother’s girlfriend was rude. And while she had gotten plenty of compliments about her little black dress, it was starting to feel constraining and uncomfortable. However, the steak and asparagus - that was excellent - and as her date kept bragging about how much money he was saving his company by writing more efficient code and paying more attention to her brother’s date than herself, she was trying to savor the last bites of her meal for as long as possible.

This was the latest series of dud dates for Chelsea, a twenty-five-year-old woman, now a few years out of college working as a business analyst at a financial company. She had straight brown hair which extended halfway down her back and featured unusually blue eyes. She still appeared somewhat youthful for her age but was still old enough that she wasn’t really mistaken for a high school girl anymore. However, Chelsea was beginning to wonder how many more years she had left in her prime.

She wore a well-fitted black dress to dinner with a halter neckline and bare shoulders, but it showed no cleavage and helped disguise her 34C bust, with the dress cutting off just above the knees. Chelsea was glad she was very likely not required to have to run in this dress, as she wasn’t sure how well she’d even be able to.

Nick was her date and had been at the top of her prospect list, being the recommendation of a co-worker who had introduced Nick to her at a couple of company functions, apparently in an attempt to play matchmaker. Unfortunately, he appeared more concerned with how great he was at impressing his company’s CFO than he was by anything else, her included.

Chelsea almost mindlessly made comments as part of the conversation here and there, just to be polite and not seem completely out of it. But it was nothing of any real note or excitement, and Chelsea wanted nothing more than to get out of there as soon as possible.

No reason was greater for this than her brother’s girlfriend. This was the first time Chelsea had met Sandra since her brother had started dating her a couple of months prior. What he saw in her, she didn’t know, but Sandra made clear from the start of the night that she saw herself as her superior.

She not only bragged about her six-digit salary but made a point of rubbing in that she made so much more money than Chelsea did - which was true, but it wasn’t like she was exactly poor, either. She bragged about dating James vs. Chelsea being single, even though Chelsea had come to the dinner with a date. She even bragged how she thought her meal looked - and must obviously taste - so much better than Chelsea’s, but on this point, Chelsea knew from first-hand experience that this was probably wrong, at least in her own opinion. Her meal was delicious.

Then there was her brother, James. People would often vote that they’d mistake them for identical twins if they weren’t the opposite sex. He also had brown hair, in a mid-fade cut, and blazing blue eyes as well. He was two years her senior and well-built but not to any real extreme. He was mostly your average guy who kept good care of himself.

James and Chelsea shared an apartment in town, an arrangement that had initially meant to be temporary but because of the convenience ended up lasting for the past year and a half. They both tried to find jobs near their ailing mother and had both landed jobs in the same city within a couple of months of each other. Housing was tough to find, so they decided to just go in together until they could find more permanent places to stay. But the fact they were close to everything important already and the split rent just made where they already were more preferable to anywhere new they could individually move to. This was magnified by the fact that their mother died only a few months later, meaning they were now their only family left.

Finally, after another half hour, the dinner was mercifully over. Chelsea insisted on paying for her portion of the meal, despite her brother (but not her date) trying to pick it up for her. Once the group was heading out to their cars to leave, Nick suddenly got interested in her. More specifically, he was interested in taking her back to his place - an offer that Chelsea firmly denied. She wasn’t one for having sex on the first date anyway, and like hell she was going to reward that outing by giving him some action.

The four finally went their separate ways. Nick left disappointed that he apparently was not getting pussy that night, which became increasingly apparent to Chelsea was the only reason he agreed to the date in the first place. James drove Sandra back to her apartment, where Chelsea presumed he would probably stay the night as he often did, while Chelsea drove back to her and James’ apartment.

Chelsea wondered just how much longer it would be their shared apartment, however. While the arrangement had made sense until now, James and Sandra seemed to be getting serious. Chelsea figured it would only be a matter of time before James and Sandra wanted to get their own place. He seemed to spend a couple nights a week at her apartment already as it was.

She finally arrived home and threw her purse onto the kitchen island and let out an exhausted sigh. She unzipped her dress and let it fall off, exposing a pair of black panties and a black stick-on bra. She peeled the bra off and tossed it on the island as well, and picked up and folded her dress, setting it beside the bra.

She walked over to the couch and plopped down on it, grabbing the remote from the arm of the couch and turning the TV on. After a night wearing the dress and wanting to get away from dinner, letting her body feel the circulating air of the apartment was a relief. She wanted to feel as free right now as she felt constrained and stuffy at the dinner.

She started somewhat mindlessly flipping through channels to see if there was anything worth watching on. Baseball, reality shows, whatever the hell that show is. Never had “57 channels but nothing on” been more true. Finally, the TV landed on some hot-guy romance movie which was obviously not of the highest quality plot or production-wise, but that wasn’t really the point. It was trash TV for single women like herself, and she decided that is what she wanted to watch.

“Mmm…yeah,” Chelsea mindlessly remarked to herself as a nameless shirtless guy with well-defined abs was currently on screen. She could feel her nipples harden up, probably from the combination of being exposed to the open air and the muscly guy she was now admiring on the TV.

She soon found herself sliding down on the couch, and her hand reaching under her panties. She gave out a slight moan as she started to very lightly poke and rub her clit. She thought about getting up and turning off the lights in the apartment, but it seemed like too much of a bother at this point.

“Aw hell, why not…” she finally said out loud to herself, as she pulled her panties down her thighs far enough for her to be able to kick them off, having them land on the floor just in front of the TV. She licked her fingers and spread her legs and reached her right hand back down and started working on herself in earnest, rubbing her clit and occasionally moving down to her labia and back up. She then licked her left fingers as well and started to squeeze and run those fingers around her left nipple. She started to moan - first softly, then a bit louder. The walls in the apartment were pretty good, so she figured none of her neighbors would hear, but then again, at this point, she kind of didn’t care if they did.

She continued to work on herself, her moans increasing in volume and intensity. Her hands were trying to find all the good places. Her left hand worked both breasts and her right hand continued to rub, and even occasionally finger herself.

That’s when she heard it: the sound of the deadbolt on the front door unlocking.

“Shit!” she remarked out loud to herself in a panicked voice. There was no way she would be able to rush to her room before the door opened and not be noticed, so there was really only one other option: she grabbed a navy blue blank that was lying over the back of the couch and threw it over herself as quickly as she could just as James stepped through the door, closing and locking it behind him. Luckily, the way the couch was situated, he probably didn’t notice the frenzied attempts by Chelsea to cover herself from the neck down under the blanket and make it look like that's just how she was sitting there.

“I kinda figured I might find you there…” James remarked with a smile, also putting his keys and wallet on the kitchen island as well before he noticed the jumble that was her dress and bra there as well.

“Couldn’t wait to get out of the dress huh? I guess I don’t blame you.”

“Ah, yeah. Just couldn’t wait to get into something more comfortable…” Chelsea tried to sound as normal as possible, even though her heart was beating what felt like 200 times a minute. She heard moans from the TV show she was watching and quickly fumbled for the remote to mute the TV.

“I figured you would stay over at Sandra’s place tonight…” This was actually what she thought. She hadn’t even considered the possibility that James wouldn’t be staying over at Sandra’s apartment for the night, so now she was wondering what happened to change that.

James slipped off his shoes. “Yeah, about that. Look, I’m sorry about Sandra. I’m not sure what got into her tonight.”

"Oh, it’s okay…” Getting into what might be an extended conversation about what happened that night wasn’t exactly what Chelsea wanted to get into at the moment. For starters, she didn’t want to really think about the dinner again in the first place. But second, she was hoping James might go to his room to change out of his clothes. That would give her an opportunity to sprint to her own room in order to put something on. Unfortunately for her, he just undid the collar button on his shirt and started walking towards the couch.

“It’s really not okay…” James sat on the other end of the couch from her. “I told her that her behavior wasn’t appropriate on the way back to her place.”

“What did she say to that…” Chelsea didn’t really want to hear what excuses Sandra had come up with, but she was now curious to hear what her response was to James actually challenging her on it.

“Well…” James let out a sigh and leaned back into the couch. “She started yelling at me about how much worse I was treating her than you and what was I doing living with you anyway and I should dump you and move in with her.”

Chelsea let out a dark little chuckle. “She told you to dump me, huh?”

“Yeah, as if you were competition for her or something. Anyway, I told her that if she was going to keep insulting you like that then I might not move in with her. She then said if I couldn’t put her above you, then we were over. I tried to be reasonable with her the rest of the way to her place, but she apparently made up her mind. Once we were at her place, she didn’t even say goodbye after she got out of the car. Just slammed the car door and stormed off.

“Oh…I’m sorry. I didn’t mean to cause you any trouble…” Chelsea did feel a bit bad. She thought Sandra was rude, but she by no means wanted to cause James and her to break up over it.

“It’s okay, I suppose. I mean, don’t get me wrong, I’m kinda still shaken about it. I thought we had a good thing going. But maybe it’s a blessing that I found out that she was kind of crazy before we got too far along…”

“Yeah…” Chelsea really didn’t know what to say. She felt extremely awkward, for multiple reasons.

The pair of them just stared forward for a few moments, not really sure what to say, the muted TV movie still flashing on the screen. It was then that James had apparently noticed: the pair of black panties just sitting on the ground in front of the TV. It then perhaps registered in his brain, adding that together with what he had seen on the kitchen island.

“Say, Chelsea.”

“Yeah?”

“When you took your dress off, you didn’t happen to put anything else on did you?”

Chelsea’s gut dropped, and she could feel her face suddenly flush with embarrassment. She slid down the couch a bit further, pulling the blanket up so that it covered her mouth and nose. James then let out a laugh.

“I was wondering why you were covered up like someone in the Arctic when it isn’t even that cold in here. I’m sorry if I interrupted anything.”

“It’s okay.” She could still feel herself blushing, and her response all but acknowledged that he had, in fact, interrupted something. “I was…just enjoying being able to just lay out like that, you know.”

James let out a laugh. He started to say something, seemed to think better of it, then decided to go ahead anyway. “That made me think of that one time. You know...hot summer day, I think the AC was broken or something too.

Chelsea let out a little laugh, and finally lowered the blanket down to her neck again. “Oh yeah, I remember that. It was a really hot summer too. We didn’t care, we were so hot. We were resting the bowls on ourselves just to cool ourselves down, I remember.”

“And when we had to go out later, we got dressed and that was that. I’m not sure we even really talked about it after that. It was like a little secret that we never acknowledged but both kinda enjoyed.”

“It would have been more fun if it wasn’t so hot.” Chelsea let out a little laugh. She hadn’t thought about that day…maybe even since it happened. But she pretty vividly remembered it now. God it was hot. God was the ice cream good. She found that chilling with James naked at the time was surprisingly not all that strange, although they had never done it again after that. As James had said, it was one of those events where they had enjoyed the experience, but somehow knew it was something they shouldn’t or couldn’t do again.

“We do have some ice cream in the freezer…” James remarked with a slight laugh as he made a quick glance over to the freezer.

“What? You suggesting we just chill out naked again?” Chelsea laughed at the absurdity of it. When they had done it before, it was hot. They had an excuse. What reason did they have to do it now? Arguably, they were more innocent at the time too. Exposing your naked bodies perhaps wasn’t quite as shameful then, but even then they already knew it was something they shouldn’t do. But they were proper adults now. They had lives. They had responsibilities.

James put his hands up like the Neil Degrasse Tyson meme. “You’re the one who said it not me…” he said with a bigger laugh this time.

Chelsea lowered the blanket down so that it was now just above her breasts, baring her shoulders and all but confirming she wasn’t wearing anything underneath. She wasn’t sure why she decided to do that, although the fact that she was starting to get hot under the blanket was one reason.

“It is starting to get kinda hot and stuffy under here.”

“I mean, it’s up to you…” James remarked with a laugh.

“Okay, you get the ice cream then…” Chelsea’s heart rate, after calming down a bit just chatting, accelerated again. Was she really about to do this? She didn’t really mind, other than the nagging feeling in the back of her head of “what would other people say?” But what would they say? No one else was here. It was just her and James. And James didn’t seem bothered by the prospect. He all but suggested it!

“Alright then.” With that James stood up and walked over to the kitchen. Chelsea watched as he walked that way, and once he seemed to for sure be going over there, she slowly pulled the blanket up, uncovering her feet, then her legs. She then folded it, and set it on top of the middle cushion on the couch. She had some thoughts of pressing the abort button and running to her room while James had her back to her, but then again, she had kind of mentally committed herself to this. There was an air of childhood playfulness to the idea that she was intrigued by. She finally just sat back up on the couch, having slid so far that her butt was about to slide off of the cushion.

Her heart was still beating fast, and she could feel herself flushed all over, but she wasn’t really excited, just nervous, like what her brother thought of her naked body actually meant anything. She fumbled with the TV remote and tried to find something a bit more appropriate to watch on TV.

Unbeknownst to Chelsea, once James had dished up the ice cream - cookies and cream - he set the...

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Written by JourneyYoung
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