Work Text:
Jennifer Tallulah Humphrey was in her mid 20s and is married to mob boss/international drug dealer, Damien Dalgaard, the son of a Belgium Ambassador. It wasn't necessarily a bad marriage, Jenny just wanted to get out of a rough spot she was in and Damien happened to save her, while Damien just needed his father to get off his back about how he should get married. The whole thing was for both of their benefits, Damien wasn't a bad husband by any means but he was absent quite a lot.
The one thing he did ask for her is to stay loyal, mainly just to keep up appearances, and if she was gonna be having affairs, it had to be discreet. Far away. Fake names. All of that, that's all he asks. Because if news outlets or bloggers found out that Damien Dalgaard's wife was having an affair they'd start to question whether or not their marriage was as perfect as it seemed in the public eye. And if his father found out, it would be bad for business and for the both of them. Basically and overdramatically, it was a life of death situation, his father was fucking terrifying when Jenny met him and has not seen him in person since and it was for the best.
And well, Jenny had no means of cheating on him. She certainly wasn't the type and Damien, despite being kind of a sleaze, was weirdly kind to her. He did give her a home in the Upper East Side, she felt like she had owed him loyalty. That was until she met Agnes Andrews, this crazy model she had met in downtown Manhattan, the two instantly hit it off. Agnes brought this wild, chaotic energy that Jenny found sexy.
The two girls ended up having a fling for a few months, it was exhilarating. Jenny only had ever kissed girls when she was younger, and never went beyond that. So this whole thing with Agnes helped her explore her sexuality. She did still like men, of course, but women were a whole other level of something else. Or just women like Agnes that made Jenny’s heart race in excitement.
Thankfully, being married to Damien had its perks, which meant access to his credit card. So Jenny decided to fly her and Agnes across the world to pretty much anywhere they desired to do fuck all, and it was great. She had never felt more alive (especially with the amount of times she felt like she died and went to heaven with the amount of times Agnes went down on her).
Before, Jenny hadn't really been with a lot of people. She wasn't the type of girl in high school to be sleeping around (not that there was anything wrong with sleeping around, it's just not for Jenny), so she never really found out what she liked and didn't like at an early age. Though she stupidly got drunk and lost her virginity to probably the worst guy on the planet, she had to take 3+ showers the next day to rub the shame off of her but it never truly went away no matter how hard she tried.
After that, after high school, she wanted to reclaim something she lost in a way. To feel in control and find out what she likes and who she'd like to do it with. So before Agnes (and hell, before Damien too), she slept with a couple of dudes and Jenny wanted the chance to explore being with women as well. Agnes was probably the best choice she could've made, even if Agnes wasn't the most stable woman of choice, but it's not like Jenny was looking for a girlfriend or a healthy relationship when she was technically married to someone else (Agnes knew that from the jump, the girl just wanted to experience what it was like with a married woman).
Yet, all good things had come to an end. Especially since they worked together on building a brand with Jenny wanting to start her own fashion line that Damien would pretty much fund if she asked. Agnes was her partner who encouraged her to do the most insane things ever. But they got into disagreements over what they wanted and Agnes ended up burning Jenny's designs in front of her, breaking off their partnership and their relationship in the process.
Jenny asked Damien if she could get off the island for a while, and he was fine with that. He had to go back to Belgium for a few months because his father requested he'd come home. Which then led Jenny back to her childhood roots in Brooklyn.
Once graduating high school, she left New York for a long time, and Jenny didn't really contact her brother or father that often. All she knew was that her dad had married his old fling from 20+ years ago, Lily van der Woodsen and got married a year back (she was at the wedding, of course, just because she hadn't talked to him in a long time didn't mean she wouldn't show up on his big day despite a part of her hating him), Lily was nice she had a son around Jenny's age, Eric, and they became two peas in a pod, clicking almost instantly. Eric was probably the only real friend she ever had in a long time, and a friend is what she needed. After the wedding they kept in touch, and Eric was the only family member that attended her and Damien's wedding (the ceremony wasn't that big, they just eloped at city hall and called it a night, which they agreed on).
With Dan, her older brother who she loves so much but also kind of hates that she heard online that he's dating her former high school nemesis/bully/psychosexual crush (Jenny doesn't like to talk about that specific part, she repressed that deep to her inner core), Blair Waldorf. She hasn't really confronted Dan about it because, again, they haven't talked in years. Maybe Blair has grown from the high school bullshit and actually became a tolerable human instead of being the person that people loathed being around, but Jenny didn't have much of an interest at finding that out.
Where else can she stay? The answer was Vanessa Abrams, probably the only person from her past she actually still spoke to who never shamed or undermined her at all. And when she showed up on Vanessa's doorstep, the Abrams couldn't refuse the younger girl she saw as her little sister. Plus, Vanessa wasn't alone either, she is actually dating someone who had just moved in with her a couple months back.
Turns out to be Eric's older sister who is also Jenny's stepsister, Serena van der Woodsen. Honestly, Jenny was shocked for a multitude of reasons. The main one being that Vanessa is very known, and very vocal about her hatred of rich people, especially ones like Serena who got stuff handed to her without putting in any effort.
Not that Jenny hates Serena, Serena is actually very nice despite growing up in such a toxic environment that was the Upper East Side, she just didn't really see it coming.
Apparently since Dan used to date Serena before Rufus and Lily got married, he introduced her to Vanessa and they instantly clicked. Was it weird for Dan to find out that his ex/step sister and his best friend that he had a wishy washy romantic history with start dating? A bit, Jenny assumes, but he became supportive of it because he wants both girls to be happy.
And to welcome Jenny back home to Brooklyn, they decide to go to a nearby bar, only after both Vanessa and Serena beg Jenny to come.
“Please, Jenny, it'll be so fun!” Vanessa starts pleading.
“I don't wanna be seen as a third wheel.”
Serena jumps in to reassure her, “Of course not, you don't need to worry at all. We want you with us!” and Serena gives a sad, puppy dog eye look. Vanessa then points, “You can't say no to that face, trust me, I’ve tried so many times since we started dating, but I always end up caving.” and Vanessa had a point because Jenny ended up caving and they went to the bar.
The three girls actually had so much fun together for a couple hours. Only until Serena drank a little too much for her own good and Vanessa takes her home. Jenny says she'll catch up with them, she just wanted to finish up and have a moment to herself.
It only started getting weird when she left and this person in a hood started following her (it wasn't the first time she was followed and certainly not the last. Though she had pepper spray in her jacket just incase). She tries her best to maneuver out of the situation and ends up rushing into a diner, which thankfully had people in it. Not a lot because it was very late but enough for whoever was following Jenny to not try anything without someone calling the cops first.
The blonde took a seat at an empty booth, elbows on the table with her head in her hands, trying to steady her breathing.
She was then approached by a guy that wasn't that much older than her, “You okay?” she looked up at him and for a weird moment, she got lost in his eyes. Jenny snapped herself out of it, “Yeah, I'm fine. Can I just have some coffee, uh—” she looks at his name tag, “Nate?”
The guy gave her a nod, “Black coffee?”
“Yup.” she nods. The wait wasn't that long and he had returned, “So, what's a girl like you hanging around here?” the Humphrey looked down at herself and well, she certainly looked more like an Upper East Sider than as someone originally from Brooklyn. Jenny just answered, “Wanted to get away from everything. Life. Obligations. All of that.”
Nate let out a small chuckle, “Yeah, I know the feeling.” He then further explained, “Moved here with my friends a couple years back after cutting my family off. Most of my life, I was used to having everything handed to me, so the change was difficult but I'm still adjusting to having to work for it.”
“You're not from around here?”
“Lived in Manhattan my whole life.”
“Surprised we never found each other. Been living there the past few years.” Jenny smiled up at him, "I'm Jenny.” She lifts up her hand to shake his and Nate immediately accepts her handshake. Jenny then takes a drink of her coffee, looking up at the waiter providing for her, not leaving his spot right next to her table.
Nate then shifted the subject, “Hey, so, uh. My shift is ending in about ten minutes, would you like to take a walk with me or something?”
“With you?” She looked surprised at his kind offer, and she couldn't decline, “Yeah, sure, a walk sounds good.” Jenny finishes up her coffee as Nate prepares to clock out for the night. She's standing outside the diner with her coat wrapped around her as Nate comes out, “Ready to go?”
“Of course.” She loops her arm in with his as the two go for a walk together and start talking about their lives. Started with Jenny asking, "You said you cut your family off. Was wondering how you got up to that point?”
Nate just sighed, “I've been contemplating about it since I turned 18. My dad, he's in jail for fraud and embezzlement. My mom basically fell apart after that. My grandfather on my mom's side expected me to go through the family political machine and come out a clone. I saw what it did to my cousin, Tripp, who originally wanted to be an archeologist, and now he's Congressman.”
It took Jenny a moment to realize who he was referring to, “Wait, your cousin is Tripp van der Bilt?”
“Unfortunately.”
The blonde let out a chuckle, “Well, I always had this weird feeling about him. Maybe it's the way he smiles in the papers I read that bothers me. So creepy.”
“Hey—” Nate playfully threw up his hands, ”I would say the same thing. Plus about less than a year ago, I heard from his now ex wife that he's been having an affair. And honestly, the past few years of where he was heading in his life, I'm just honestly not surprised at this point that I just expected it or something like it to happen eventually.”
“Seems like you were really close.”
“We were. We always spent the summer together. Kind of looked up to him thinking he was the honest and the good one of the family. So imagine my disappointment when he became someone I couldn't recognize.” He paused for a moment before continuing, “When Tripp and I got into this massive blowout about who he's become, Grandfather stood with him and then I was the bad guy, because since Tripp is supposed to be the good and honest one, that made me the family disappoint and I just couldn't deal with it anymore. So I just cut them off, called my friend and asked to move in with him in Brooklyn and here I am.” Nate looked at Jenny and asked, “What's your story?”
Jenny just shrugged, “Well, my family is not as much of a mess as your family is. It just unknowingly and inevitably tore itself apart. Starting with my parents’ marriage collapsing. I took it pretty hard, and in high school, I turned all rebellious as a way to process it. I made some pretty stupid and awful mistakes, and it caused a tear in my relationship with my dad since my mom packed up and just left without a care in the world. He just looked at me and said that he doesn't see his daughter anymore. When it came to me and my brother, he was the good one, I suppose. Maybe not honest but he was a good person and knew how to hide his pain well. Way better than I.” The Humphrey let out a laugh to hide the pain that was boiling deep down inside her, “So after high school, I just kind of left and didn't really talk to my family since then. The only time I've seen them was when my dad remarried last year, nothing more.”
Nate didn't say anything, he did however put his arm around Jenny and pulled her closer to his side. She felt the sense of comfort, so by instinct, she set her head on his shoulders. It was the first time in a long time that someone, anyone had held her in any way and it felt nice. For someone to hold her and reassure her that everything was okay.
They showed up at Nate's apartment and Nate offered to let her come inside. Jenny froze for a moment, to process it. Nate was nice, sweet, and sexy as hell. He then said, “You don't have to if you don't want to.”
“It's fine, I'll come in.” and she follows him inside the apartment, “So, where's your roommates?”
“They're out of town for the weekend for a Seder.” Nate explains, “So I have the whole apartment to myself. Which means I don't have to hear them go at it for one night.” and both of them had laughed at that, “They've been dating for the past couple years. Despite being friends with both of them, I'm always the third wheel.”
“I know the feeling. My friend and my stepsister have been dating and I just recently moved in with them. So I guess we have something in common.” The two of them had exchanged laughs. Afterwards, Jenny looked around and saw a Wii Nintendo and her mouth went wide, “No way.” she walked towards it and grabbed a controller, “You have these?”
“Yeah.” Nate had nodded, “My roommates got it for me for Christmas last year. I'm assuming you're familiar?”
“Of course.” Jenny let out a playful scoff, “My brother and I had intense matches when it came to bowling. I always won them though, I was determined to win.” she felt a little proud of herself there. She remembered she beat Dan in one round and it was funny to see him lose it but he managed to calm down because at the end of the day, it was just a game. He was lucky he didn't cry, at least in front of Jenny, if he did, she probably would've known about it and held it over his head for a couple months at most.
Nate then offered, “You don't mind if I join you, right?” and Jenny shook her head before Nate went and fired it up.
They did bowling, tennis, baseball, any available game that was on the Wii, it was fun until both Jenny and Nate got a little too close for two people that just met earlier in the evening.
There was a brief moment where the two of them were way too close for two people that had just met less than an hour ago. And honestly? It really made Jenny think of the last time she had gotten laid, which was a few weeks ago before Agnes broke up with her, burned her stuff, blocked her number, and changed the locks to her apartment. Sure, it hadn't been that long but sometimes a girl has needs. And God forbid a woman is horny.
Jenny was about to kiss Nate til he looked down and saw her wedding ring and immediately pulled away, “Uh, you should go.”
“What?” she then looked down to see she still had her ring on and let out a heavy sigh, “Okay, look, this is not what you think.”
“I mean, it kind of shows for itself.” He waves his hand over to the wedding ring, “You're married.”
“Yes. I am. But it's not necessarily like we married for love. It was to benefit each other.” She tried to explain, “And you aren't exactly the first person I had an affair with. And I know that sounds bad, it really does, but Damien and I came to an agreement to do whatever the hell we wanted as long as we didn't get caught.”
“Oh, that makes it so much better.” and that response is so obviously full of sarcasm, it would be stupid to think otherwise.
“Just so you know, I'm nothing like your cousin. He married for love, til death do them part, right? I married so I could get what I wanted, which was not love, it was a fair agreement.” She stepped closer to Nate and gently grabbed his hands, “Look, I'm not some sleazy political figure breaking my vows. Or the ones who swear loyalty to their partners, promising to never hurt them but doing it anyway. I'm not a moral compass nor the greatest person ever, I've made mistakes, and I still do them because we're all human and we're bound to make mistakes. Have you not made some poor decision making in your life?”
Nate just sighed, “You have no idea.” He took a pause for a brief moment before continuing, “One of my friends who lives here with me, her and I actually used to date from basically kindergarten to the end of high school, and I wasn't the best boyfriend. I cheated on her with her best friend. Still as shocked she forgave me after that, but we inevitably broke up anyways because we were growing apart. And just a few years ago, I participated in someone else's affair and that didn't end well. I've done a lot of dumb things myself, I just want to be better than who I was, and stop making mistakes.”
Jenny placed a hand on his face, looking him in the eye, “You're gonna make mistakes in your life, Nate. No one is necessarily perfect. I mean, look at me, I'm a mess myself.”
“You may be a mess but a beautiful one.”
“Wow.” She let out an exasperated laugh, “That was cheezy. But actually kind of smooth.”
“Really?”
“Mhm.” She wrapped her arms around his neck, bringing him into a kiss and wow… He was a good kisser. It was different from Agnes, from Damien, from other people she's kissed, like there was a variety. With Damien, it was fun, but they don't necessarily kiss often, so she doesn't remember the details so she guessed it wasn't as memorable as she liked to imagine it. Kissing Agnes was more rough, some of those kisses ended up with a smidge of blood because Agnes bit Jenny's lip a little too hard, other kisses had hair pulling and Jenny was strangely into that. But with Nate, there was a softness with the passion and intimacy which was new territory for her. And the kind that she wants to explain even further.
Next thing she knew, she was pressed up against the wall as Nate had planted kisses along her jaw. A part of her felt like she could tell he knew what he was doing, and that was someone she needed. She gently grabbed onto his arms and gently pushed him to the couch on the other side of the room and straddled him before placing her lips against his again.
Her hands went down to his zipper as she unzipped him, “You don't mind if I?” Jenny looked up at Nate, asking if it's okay with what she's doing. He immediately nods and says nothing else.
Everything else after was a bit of a blur the moment she sank down on him, her hands clinging onto his shoulders as she felt a shudder down her spine. It had been a while since she had actually been with a man so it was weird at first but Nate made sure she was as comfortable as she wanted and was kind and caring and attentive to her needs. There was also just something about the look in his eyes with the comfort he had given that made Jenny feel something hadn't felt in like… Ever. She couldn't really recall a moment of having sex feeling this intimate.
Maybe it's guys like Nate who easily look at girls with adoration, especially if said girls were on his dick, they'll look at women like they hung the moon. Whether true or not, she liked the way he looked at her, and the way he made her feel like he knew what to do and it really showed when he carried her all around his apartment from the couch, the counter and wherever else until they reached his bedroom.
It felt like pure bliss that she couldn't even recall 100% of it other than pleasure. Jenny does recall wrapping her legs around Nate’s waist very tightly and gently biting his shoulder when she came.
And honestly? Wow. Nate really had put any other guy she had been with before to absolute shame, and no guy could ever compare. She instinctively wrapped her arms around him as she felt her eyes getting weary. And surprisingly, Nate didn't mind at all, in fact, he wrapped one arm around her waist pulling her closer to him.
She then easily fell asleep with her head on his chest and she felt at peace.
Temporarily, of course.
When she woke up, everything was fine, it seemed peaceful, quiet, pure bliss. Nate was still asleep so she moved up to his face and planted kisses til he woke up with a smile on his face, “Hi.”
“Hi.” Jenny gave him a soft yet quick kiss before sitting up, but Nate gently pulled her back down on top of him, “Nate, come on. I have to get going, my friends are gonna freak out when they realize I didn't come home last night.”
“Just five more minutes, and let me make you some breakfast. I am very good in the kitchen.” He chuckled.
Jenny playfully slapped his chest, “So I've heard.” She takes in a deep breath and relaxes for a moment in his arms while Nate planted a kiss on her forehead every now and then.
After, they get up and get dressed (Nate in just sweatpants and Jenny in one of his shirts) and go to the kitchen where Nate makes — well, tries to, he struggles at it, but Jenny appreciates the effort — some pancakes, some were a little burnt but we're still edible. Plus it was very cute to watch Nate try and flip pancakes without him flipping it off the pan. He just reminds her that he's a waiter, not really a cook unless it involves putting something in the microwave or oven for a certain amount of time, but he likes to at least try.
When he was done, he put the plate on pancakes in front of her while sitting down with his own plate. Jenny takes a bite and says, “Though nothing will ever beat my dad's waffles, even if I grew tired of them. This is very good and gives my dad some worthy competition.”
“Why thank you.” He takes a cute little bow that made Jenny giggle and she couldn't help but stare at him. Not just because he's attractive — though he very much is — there is just something about his smile, his demeanor that just brings such a bright and positive energy into her life that felt natural and not forced, and it was something she so desperately needed for the first time in a long time.
It didn't take Jenny long to finish and heads over to the kitchen sink to wash her plate. As she does that, she feels Nate's arms wrap around her as he planted soft kisses on her neck, “Are you always this needy after hookups, or am I that special?”
“A bit of both.” He mumbles against her neck, turning her around to bring her into a kiss, and Jenny would never get tired of kissing him. He carries her up to set her up on the counter. But just as things are starting to get heated, the front door opens and two people walk in that Jenny doesn't see yet because her back is facing towards the door, but she turns around hearing a gasp.
And she sees her brother, Dan and Blair Waldorf seeing her in action. And when Dan realizes the girl Nate is fooling around with in his kitchen is his sister, he doesn't necessarily take it well. At all. That he had to drag Nate to the other room and all Jenny and Blair can hear is muffled yelling, mainly from Dan.
Jenny sits in the living room with Blair, “Well this is just a coincidence that of course you'd live here. You always seem to haunt every aspect of my life.”
Blair let out a scoff, “Nate is in your life? Really? Oh, Little J, are you so naive to think that Nate would want something more?” and the brunette just let out a laugh, “He always does this, I'm afraid. Last serious relationship he was in was with Serena and that went up in flames, so now he only does occasional one night stands. If he made you think otherwise, you're delusional.”
“Whose to say I was looking for a serious relationship? Didn't Dan tell you I'm married?” Jenny wants to brush over that Blair calls her Little J ever since high school and it shows that it has not gone away. And she brushes over the fact that Serena was with Nate because it really makes this circle out of her, Nate, Dan, Blair, Serena, and Vanessa incestuous in the way she did not want to think about. Frankly, she wants to drill it out of her mind.
The Waldorf woman sighs, “Yes, unfortunately, he wouldn't shut up about how he and Rufus didn't get invited and you just eloped with your Belgium Beau. But I assume the marriage isn't perfect, or else you wouldn't be here with Nate's head between your thighs.”
“Nice chat as always, Blair.” Jenny responds sarcastically as she gets up from her seat and grabs her clothes that were left on the couch since last night and heads to the bathroom to change and immediately leaves so she doesn't have to face Dan's wrath because she can already hear the words already and the specific tone he's gonna be using it to do so.
She heads back home and as she does she finally puts two and two together — she couldn't believe it took her this long to do so — that the Nate she slept with was Nate Archibald, the golden boy of St. Judes, the school Dan went to. She never really met him but heard a lot about him. Besides, they also didn't travel in similar circles ‘cause back then, Jenny wasn't exactly the type of girl most guys would go for and she was fine with that. She made her social grave and had lied in it with zero problem, once realizing getting to the top to get girls like Blair to notice her worth was not worth the time.
When arriving home, thankfully, Serena and Vanessa are asleep and Jenny disappeared into her room she didn't have the chance to unpack yet. But she just fell flat on her bed and wanted to die after the events of this morning had taken place. And sadly, she didn't live far from Dan and Blair's place and Dan knew where she lived so she was waiting until he showed up.
And in the next few days, he did. The two siblings sat in the living room over tea as Dan tries to be calm and not yell, “Look, I know you're an adult. You're not 15 anymore. I just get this sudden urge to protect from any guy, including Nate, my best friend. Plus a little worse when said best friend has brought home random woman into your home to fuck every other night when he's sad and lonely. Blair suggested a threesome while drunk one night and as much as Nate wouldn't mind being with a guy such as myself, he does remind us that if you gonna have a threesome, the third person always has to be a stranger. If not, everything gets all weird and confusing.”
“Have you learnt that from experience?”
There was a moment of silence from Dan for a moment before he said in a quick manner, “Maybe. That's none of your business.”
Jenny just brushed it aside and said, “Dan. I love that you still care about me, even if we haven't talked in a few years, but like you said, I'm an adult. I can take care of myself. I'm not fragile, and Nate's not gonna break me.”
“Maybe not you, but certainly everything else around you.” Dan made a little comment, “‘Cause when he and Serena were dating, They broke his dresser. And I was the one who had to buy him a new one. Including a new bed frame. He's broken a lot of things, Jen, that Blair and I had to pay for. And that was before he got a job, thank god. But it's not always great to hear something break in the middle of the night along with all the other noises.” and Dan just kept on rambling and oversharing so much about it that it was slightly concerning. Not his rambling, she was used to it, but the topic he was rambling about. Like wow, Dan, why are you so invested in Nate’s sex life?
Jenny just continued with, “Are you worried that Nate will hurt me emotionally?”
He just shrugged, “I guess. I don't know. I've seen you heartbroken before, and Nate in this past year isn't one for commitment nowadays, and I know you're not looking for that because…” he waves his hand to her wedding ring, “But I know how easily you get attached. I remember Agnes. You guys were literally starting a fashion line together and then that went south.”
“Nate is nothing like Agnes.”
“I know that. More than you do, to be frank.” Dan sighs, “But Nate will hurt people he cares about unintentionally. He will say the cruelest things when he's hurt and won't even realize it til it's too late. He pushes people away because he's afraid of getting hurt, so he ends up hurting the other person before that even when he doesn't intend to. Trust me, I have witnessed Nate saying the most hurtful things to me when he's upset and I brushed it off. But you're not like me, so I think it's best if you don't get tied up with him like that again.”
After that, she didn't really interact with Nate for the following few weeks. Other than when she visits Dan as he tries to make her and Blair get along, it's usually when Nate ends up going out for the night.
With her and Blair, it really took baby steps and a lot of visits of a lot of arguing and Dan playing peacemaker for them to be at a somewhat decent place. At the very least, Jenny and Blair are not yelling at each other for once. It took longer for them to actually find solid ground and something they'd piggyback on to get along. When that day finally arrived, Dan felt at peace that his sister and his girlfriend weren't at odds anymore.
Not long after, it was Rufus and Lily’s one year marriage anniversary and they were throwing a party to celebrate by inviting all their closest friends and family.
It was thrown at the Palace, Blair's mom, Eleanor helped plan it because of course, it's what Waldorf's will do when it comes to planning extravagant events. Jenny was a big fan of Eleanor Waldorf and her brand, so that Jenny would be able to make it into the industry herself someday. Dan and Rufus always knew she was destined for great things outside of Brooklyn, hell, even outside of New York itself, fashion has always been her passion since she was a little girl and Eleanor had been her idol for years. Jenny volunteered to help Eleanor with the party which made it the perfect time to be able to interact with her. The Waldorf woman was a little standoffish at first, she liked Dan because he made her daughter happy but she didn't know Jenny well enough to make an effort to be friendly.
It took time throughout the day to do so, it was easy for Jenny to get along with a Waldorf when it comes to finding common ground to piggyback on, with that being fashion. Jenny even offered to show Eleanor some designs she's made that were inspired by her, and she said she'd think about it. It wasn't a yes. but it wasn't a no either, so that was something to look forward to.
The party itself turned out great. Jenny had dressed up nice, a black ball gown that showed a little too much cleavage but she was comfortable with her body and wasn't ashamed in any way at all. Besides, she liked feeling confident and sexy and not caring about what other people would think because she doesn't dress for them, she dresses for herself.
During the party, she was sitting down at the table she was assigned too along with Dan, Blair, Serena, Eric, and Vanessa. Serena was interacting with Lily, Dan was talking to Rufus along with Vanessa, Blair with Eleanor, which left her and Eric sitting together.
Jenny noticed Eric was in silence for most of this party other than a few hellos and greetings, “Are you okay?” She gently tapped his shoulder to get his attention. He snapped out of it to look at her, “Yeah, I'm fine.”
“You've barely talked all day.”
Eric shrugged, “Didn't think anyone would notice."
“Well, I did.” The blonde pointed out, “We're family, Eric, you can tell me what's going on.”
The young van der Woodsen just sighed, “This guy I've been seeing, I asked him to be my plus one for the party.” and he notices Jenny start to form a smile and about to say something positive but he stopped her from going further, “But uh, he thought we were moving too fast because I invited him to be my date to a family event. Then I just thought, ‘What if I did?’”
“It's his loss. And it's every other gay dudes’ gain. I do believe there is some cute guy you can flirt with around here.” Jenny tried cheering him up, and a small smile started to form on Eric's face, “There we go. And hey, maybe you're not ready to mingle or anything like that yet, but have no fear, I will be your wingwoman.”
Then Vanessa had walked over to the table to sit down, overhearing that last part, “Did I hear someone say wingwoman?” the Abrams took a seat next to Jenny’s left, looking curious.
“Jenny wants to set me up with a guy because the one I was seeing didn't want to show up tonight.”
Vanessa had let out a chuckle, “Well, one thing I know about Jenny is that, once her mind is on something, she will be fixated on it happening. So don't even think about trying to stop her.”
“I won't.”
Jenny looks over at Vanessa and asks, “How are you and Serena? I know I shouldn't ask since I live with you guys but… I was just wondering.” she placed her chin on her palm as she looked at Vanessa in curiosity. V had just sighed, “To be honest, things have been weird. Not entirely in a bad way, She's been acting weird recently and I was wondering what was happening and all that. And I did the stupidest thing ever.” She put her face in both of her hands, “I looked through her phone. And I know that sounds bad but, I was worried something was going on. But I couldn't find anything other than she's been texting Nate frequently. And there's nothing wrong with her talking with her ex who I also happened to date—” she paused when seeing Jenny's face, “It's a long story for another time. But anyway, it's just this bad feeling. And I feel horrible going through her phone. I was just scared.”
“V…”
“I know, I'm sorry.”
“It wasn't my phone, so you shouldn't be apologizing to me.” Jenny reminded her.
Then Blair sat down between Eric and Jenny on Jenny's right, “Well, my mother seems to be interested in seeing some of your designs, Jenny.” Jenny still feels slightly shocked every time Blair actually says her real name and not “Little J”, which Dan says that itself is a major show in real progress. The Waldorf continued, “Hopefully whatever you have stored looks decent enough to impress her. And you know my mother, she's hard to please.”
“You don't need to worry, Blair.” Jenny responds. There was a moment of brief silence that also took Jenny a moment to realize that Blair wasn't drinking any of her champagne, “Blair… You okay?”
Blair looked over at Jenny with a slight offended look, “Yes, of course. Why wouldn't I be okay?”
“‘Cause you haven't had a sip of your drink.” The Humphrey points out, literally pointing to the full glass. Blair just shrugged it off, “Thought I was in the mood for it, turns out I'm not.”
Vanessa then added, “Is that why you avoided the sushi bar?”
“No one was talking to you, Abrams.” Blair had snide, “So stay out of it.”
Jenny then came up to defend Vanessa, “Hey, no need to get hostile towards her, she was curious, as was I.”
The brunette had sighed and shockingly apologized, “I'm sorry. It's just been a difficult week, and I don't need you guys to make my life even more difficult. So can you stop asking me questions about why I'm not consuming XYZ, please and thank you?”
“Okay.” Jenny says, “I'm sorry for showing concern for you.”
Blair just sighed, “No worries. It's weirdly endearing you now show concern for me. You are weirdly full of surprises. Humphrey. Just like the time Dan said you had a crush on me in high school.” and that made Jenny spit out her drink almost instantly. Took her a brief moment to process it before speaking, “He said what?”
“No need to worry, I think it's cute. Besides, I'm Blair Waldorf, so I'm not surprised I happened to attract both genders. Specifically two Humphrey's.”
“I'm gonna kill Dan.” the blonde mumbled.
Blair then jokingly added, “He is quite the blabbermouth. And if you still have a thing for me, I wouldn't blame you. I wouldn't get over me either.”
“Very much am over you.” Jenny states, “I am allowed to grow out of schoolgirl crushes.” She then shifts the subject, “Can we talk about something else now?”
“Fine.” The Waldorf sighed sadly, then she tapped Jenny's shoulder, who looked at the pointed direction that showed Nate from the other side of the room, arguing with someone. Eric and Vanessa also look in that same direction as the former asks, “Why is Nate's mom here? Was she invited?”
“That's Nate's mom?” Jenny looked surprised.
Vanessa nodded, “Yeah. Met her once at a van der Bilt function when Nate and I were together. Fair warning, she sucks.”
“I can back you up on that one.” Blair agreed, “She was the one forcing marriage upon Nate back and high school. I was fine with it then because I was so in love with him, but looking back now that I'm not, it was not great.”
Eric takes a sip of his drink, “I try to steer clear of any van der Bilts at any Upper East Side function ever. I once was stuck in a conversation with Nate's grandfather, it was not the best time and I wish I could take those two hours back.” and then he takes a chug of his drink, trying to wash that memory down and bury it deep within.
Jenny then decided to get up and walk over there herself, Blair, Eric, and Vanessa try to stop her but to no avail. She approaches Nate and his mother and introduces herself, “Mrs. Archibald, Jenny Humphrey.” she raises her hand to shake hers, “Lily's stepdaughter. We haven't properly met.” Anne carefully shakes her hand before pulling it away, “So what's going on?”
“Nathaniel here should really stop with his pride and come home. This act of rebellion by living in Brooklyn is ridiculous.” and Jenny can sense the annoyed look on Nate's face but that did not stop his mother from continuing, “You are an adult and you're acting like a child. And this is not gonna get you anywhere in life.”
“I seem to be doing just fine on my own, being surrounded by people who actually care about me.”
“We do care about you.”
Nate just scoffed, “Yeah, but you and Grandfather would rather side with Tripp when he's in the wrong than ever side with me. So, no, I'm not coming home, because it hasn't felt like home to me in a long time.”
“Nathaniel—”
But Jenny was the one to cut her off, “Lady, he said back the hell off. If he doesn't wanna be a part of your family, stop trying to force it onto him.” and she immediately received a nasty look from Anne. The older woman had said, “This is frankly none of your business, Jennifer. And I'm tired of people like you filling my son's head up with things he does not want. Like that Vanessa girl.”
And oh, that really ticked Jenny off. She had heard Nate defend her, ”Mom, leave Jenny alone, she didn't do anything.”
“She's putting her nose where it doesn't belong.” Anne rebuttals, “You do not need that in your life.”
“Which is why you're not in mine.” Nate then walks away. Anne looks over at Jenny before walking away, purposely hitting her shoulder with hers without saying another word. Vanessa and Eric had approached her to check up on her, “Is everything alright?”
“Everything's fine.”
Rufus and Lily walk up to Jenny as the latter says, “I'm so sorry, Jenny. I didn't know that Anne would show up. To be honest, your father said it was best to not invite her and I should've listened. I just didn't think she would be causing trouble with Nathaniel while here.”
Rufus then consoles Lily, “Lil. you have nothing to be sorry for. Even though from what I heard from Nate, I don't like anyone with the last name van der Bilt, anyways.”
“Do any of us, really?” Eric comments.
Jenny goes off to find Nate, Eric texts her saying that he's in the Penthouse that Lily booked for all of them for the night. She gets on the elevator and heads up, she slowly walks in once the elevator dinged and she sees Nate sitting on the couch, drinking whiskey, “Hey.”
He immediately noticed her and sighed, “Hey.”
“Do you want some company?”
The Archibald just shrugged, “Sure, I guess. Do whatever you want.” and that gives her the invite to sit down next to him, “I haven't even seen my mom since I moved to Brooklyn. I cut all contact with her since and the one time I decide to show up to an Upper East Side event, she finds me and berates me.” and he downs the rest of his glass before pouring himself another one, “I never really felt like I belong anyway, but since moving to Brooklyn and starting from the ground up I felt at peace, like I finally found something that I want when for the longest time, I never knew what I did want.”
She just lets him talk, and doesn't say anything. Nate just rants on further, “Everyone in my family, my mom, my dad my Grandfather, setting me on a path they see as right. But I didn't wanna go to Dartmouth, or Yale, or whatever other college they wanted me to go to. I went to Columbia, and I graduated. And I now have a nice home, surrounded by people who do care about me and support me. And what happened tonight really just had my whole world come crashing down.”
Jenny sets a hand on his, intertwines their fingers together and Nate doesn't pull away, “I'm sorry you had to listen to me rant.”
“I don't mind. I kind of know the feeling, so I get where you're coming from.”
Nate sighs as he looks over at her, “You do look beautiful tonight.”
“Thank you.” She felt her cheeks flush up like she was 15 having a schoolgirl crush all over again. There was a moment of silence before Nate had pulled her into a kiss, pulling her onto his lap and gripping onto her hips tightly. Jenny pulls away slightly, “This isn't a good idea. You're upset, and I don't wanna take advantage of that.”
“You're not. I just wanna forget everything bad that happened tonight.” He gently placed a hand on her face before kissing her again. Then almost immediately she was pressed up against the nearest wall as Jenny feels Nate's lips going down from her jaw to her neck to her shoulder as he pulls off her jacket, the blonde girl just chuckles, “Have a thing for necks, huh?”
He didn't really say anything other than chuckling against her neck. Next thing she knows, he wrapped her legs around his waist as he carried her to his room and laid her flat on the bed. The sense of deja vu from weeks ago flooded back.
“Dan says it's a bad idea.” Jenny speaks up, “But also, I don't think he has the right to speak on who I'm with since he started dating you know who.”
“I think it's kind of a mood killer to talk about your brother right now.” He lets out a chuckle to lighten the mood, “But also, it's not like I was gonna listen to him anyway.” Nate placed a quick yet soft kiss on her lips before slowly moving a hand up her dress, “But you do want this, right?”
“Mhm.” Jenny nods with a small smile on her face. He kisses her again as he pushes her underwear to the side and two fingers slip in between her folds for a brief moment before pulling them out, making Jenny let out a small gasp before gently hitting his shoulder, “Nate Archibald, you are such a tease.”
He didn't say anything else other than helping her out of her clothes as well as his. And though this is the second time she's seen him shirtless, he still manages to surprise her. Jenny had parted her legs as her arms brought Nate down to where he's on top of her, “You don't need to worry about me, this isn't about me. You need a release and I'm just here to help. And I'm not fragile.”
“I know, but I wanna make sure you get what you want too.” Nate placed a soft kiss on the tip of her nose. He then rubs the tip of his dick against her slit before pushing in. The sensation made Jenny cling onto him, her fingers gently scratching his shoulder blades as he thrusts in and out of her.
This time around, she not only felt the pure bliss of the encounter but just remembered the small details that she couldn't before. The way Nate kept asking if it was okay to keep going, not in a fragile way, but in a considerate and consensual way to continue at a faster pace without making her uncomfortable, he just wanted to learn what she liked and didn't like. Then the way he cracks playful jokes just to see her smile. The way he was praising her for just looking beautiful, or how good she felt around him or telling her how good she was. Just all the little things she paid attention to made it really hard to not fall for him. Making her feel like the only girl that mattered to him.
“Nate, please.” She managed to breathe out. She could feel herself contract around him as she was getting closer and closer. Nate moved a hand down to rub his thumb against her clit, “Just let go, sweetheart, I'm right there with you.” and that was all that it took as she gently bit against his shoulder yet again as she fell apart underneath him and he was not that far behind her either.
Once getting to his own release, Nate didn't pull out immediately, he gently collapsed on Jenny while still inside her. And for Jenny? It's not like she minded. They both just needed a moment to compose themselves. But that didn't happen when not long after, they both passed out not long after, finding contempt in each other's arms.
And it felt peaceful.
Tomorrow, Jenny woke up feeling sore and Nate was still on top of her (and inside her). She gently pushed him off her, making him lay next to her, pulling out of her in the process. She grabs a robe that was in the bathroom attached to the room before heading out. And when she gets out, she sees Dan in the kitchen with Eric sitting at the counter watching and Blair, Serena and Vanessa sitting on the couch, and all five of them look at her with very different reactions. Dan's was the expected “I told you not to do it again” but he did not have the time to start an argument but his actions as he was cooking spoke for itself. Eric tried to hold back any smiles and wisecracks, he's always been supportive of Jenny no matter what or who she does. Blair just had an annoyed look. Serena had a confused look while Vanessa had one that showed she did not want a conversation to spark up because it was not her sex life.
Jenny sat down next to Eric who playfully elbowed her while Dan tried to avoid eye contact with her. She tried to ask a question but Eric already knew what she was gonna ask and answered anyway, “We heard the two of you the moment we walked out of the elevator last night. Dan immediately just went straight to bed with Blair following him. Serena grabbed the nearest alcohol and Vanessa put on headphones to tune it out, and so did I.”
“We didn't hear you come in.” Jenny whispered.
“Well, you were too preoccupied to notice.”
“Noted.”
Ten minutes later, Nate came out wearing a robe of his own and he got the same looks from everyone else as Jenny did and he feels like a complete idiot. Jenny stands up and walks over to him, “Morning sunshine.” and she couldn't hear Dan groan loudly behind her. And hear Blair let out a small gag from the living room as Serena tells her, “Blair, shut up, they're having a moment.” which thanks, Serena, Jenny mentally said to herself.
Jenny dragged Nate to the side and just got everything out in the open, no beating around the bush any further, "Last night whether it was a mistake or not, it's worth repeating many more times. And I know from Blair you haven't had a serious relationship since Serena, which I get. I'm not asking for commitment because I'm still technically married regardless if it was for anything other than love. But I know I want more than just sex, despite it being very good. If we have this affair until Damien’s dad dies so he and I don't need to be scared of him anymore, I can do that, only if you're willing too.”
“I'm all in.” He answers, straight up, no hesitation. And both of them heard claps from both Eric, Serena and Vanessa while Blair just playfully gags and Dan just sighs heavily, “Just please for the love of God, be careful. ‘Cause if I have to hear that Nate knocked up my little sister, I would have to kill him and Blair would help me bury the body.’
“That's true!” The Waldorf added in.
So, really. It wasn't the happy ending they expected, but it was close enough. Plus the excitement and sneaking around makes it all the more fun and interesting for them. And they can live with that.