#Lily van der Woodsen

[lightgaswaterelectricityrent]

your sweet potatoes are bland.

[femalescharacters]

KELLY RUTHERFORD as Lily van der Woodsen in GOSSIP GIRL (2007-2012) ✦ 1.12 "School Lies" dir. Tony Wharmby

[meiiflua]

welcome back queen Serena👑

~it's gossip girl season.♡

[bloody-cupcakes]

Yandere/dark! sugar mommy! Lily van der Woodsen x reader headcanons

Tw: yandere/dark content, gender neutral reader, sugar mommy! Lily, age gap relationship (the reader is notably younger than Lily is but still older than her kids), the reader is kind of like a surrogate parent for Serena and Eric/they see the reader as a parental figure, nothing explicitly smutty but there are obviously some suggestive areas given the subject matter

A/N: this is just a little idea I had that I wanted to write out hehe 🤭 I plan on making another set of headcanons that are more explicitly smutty later on

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The whole situation most likely only came about due to pure accident (maybe fate and a little bit of luck if you believed in those sort of things)

You were in a similar position to Dan in the sense that your family had some money, just not nearly enough for you to properly fit in with the Upper East Sider crowd

Lily met you when Serena befriended you at an event of some kind, excitedly dragging you over to meet her (something she probably only did due to the alcohol in her system)

She explained that you'd had a sibling that went to school with her, which led to you realizing you had more than just that in common, and that's how the two of you became friends

The moment she laid eyes on you, Lily was instantly hooked, unable to keep her mind from drifting to more scandalous and explicit thoughts

That night she couldn't sleep, thinking about what it would be like to have you in bed with her: kissing her skin, caressing her body, whispering sweet words... she was certain you'd be a gentle lover

Sure, you were her daughter's friend, which did make her feel a little bit guilty about being so obsessed with you, but that guilt was lessened by the fact that you were slightly older than Serena was

Besides, you were everything she looked for in a person: intelligent, charming, polite, and most importantly her kids liked you, something that never happened with the partners Lily chose

There was, however, the catch of you not technically being a part of the Upper East Side society, something that could easily be corrected with a simple proposition: you becoming her sugar baby

Was she nervous to ask you? Absolutely, but she did her best to remain calm and straight-faced, proposing it to you more as a business opportunity rather than a relationship

Of course you were a bit shocked when she came to you with the idea, but you'd be lying if you said you weren't intrigued by the offer

After all, Lily van der Woodsen was a very powerful and successful woman, not to mention incredibly attractive on top of it all

Despite that, you also got the sense that she was a bit lonely and needed some extra company, something you were more than happy to provide

The conditions of the arrangement were simple: she'd buy you whatever sort of things you wanted or needed in order to help you better fit in with the UES socialites, and in turn you'd escort her to events and give her companionship, among other things

Obviously you accepted her offer, which left her feeling a sense of triumphant satisfaction that she got you to agree so quickly and easily

Although she didn't want to, she very well could've resorted to blackmail in order to get you to do what she wanted, so the fact that she didn't have to made her feel relieved

It wasn't long after that she had you move in with her at the VDW mansion, needing to have you close to her at all times

You were given your own room to fill all of your stuff with, though it was made perfectly clear that she expected you to sleep in the bed with her, no exceptions

For the most part you're allowed to come and go from the house as you pleased, but Lily always likes to know where you're going and who you're hanging out with so she could keep tabs on you (sometimes you feel more like one of her kids than a partner because of this)

She always gets you dressed up in the nicest clothes available whenever you attend events together, making sure to keep her arm linked with yours or her hand on the small of your back or your waist the whole time so you won't feel the need to wander off

When it does happen that you get distracted at events and leave her side, she gets either Serena or Eric to keep track of you, which doesn't take a lot of convincing given that they both adore you

If anything, it almost seemed as though they preferred you more than they did their mother, constantly going to you instead of her whenever they're in trouble or if they need some advice

You're certainly able to understand their position a lot more easily than she could given how you're A) closer to them in age and B) not their actual parent

You're not above sticking your neck out for them if they happen to get into trouble, and often take their side in arguments they have with their mother

This understandably frustrates Lily whenever you do that, but you're always able to make it up to her in the end, which leads us to your end of the bargain when it comes to the whole sugar mommy/sugar baby situation

In all honesty, she wasn't entirely familiar with the concept of receiving pleasure from her partners as the ones in the past usually hadn't cared enough to put her needs above their own, Rufus being the only exception

But with you, it's so much different, because you actually care about her, and not just because she funds your lavish lifestyle

Almost every night you take the time to worship her, to tell her just how much you love her and appreciate her, and that just makes her fall more and more in love with you

Lily felt drawn to you from the first moment she saw you, but she realized one night as the two of you laid together in bed that she truly loved you like she had no other

You were hers now, and she was determined to never ever let you go

[nostalgicninjas]

[lovepinkqueens]

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[dair-to-believe]

Lily x Rufus / Dan x Blair Parallels - Part I

[andthatscanon]

later:

[barbietrice]

Serena van der Woodsen 🌟

[gostudyorillcomeforyou]

“She’s a Lily van der Woodsen girl”

She’s wise. She’s good looking. She’s expensive. She has standards.

She’s the woman that you hope to become when you’re older.

[ilovebrianquinnsm]

would any of yall be interested in a series with chuck bass? i’d probably write on AO3 but i would post links here! it would be a long slow burn but really interesting i promise!

[adropofgoldensun]

Gossip Girl | 1×10 Hi, Society When I was your age, I would’ve been lucky to find a guy like you. And I kind of did. But when it came down to it, I thought my mother knew who I was much better than I knew myself.

[neptun4ngel]

⋆˙⟡♡ the first episode of gossip girl premiered on this day 16 years ago ⋆˙⟡♡

[meiiflua]

"well, you can tell Jesus that the bitch is back."

[strideofpride]

Lily and Jenny. Jenny and Lily.

The good girls gone bad.

The transformers who’ve shaped and molded themselves into different people depending on who they felt they had to be.

From sweet young girls to the groupie & the rebel. To the billionaire’s wife & the queen bee.

The two girls who left the only home they had known as teenagers hoping for something new, something better. The two women who returned to the world that made them cold and cruel anyway.

The girls who were never allowed to deal with their trauma.

Giving up a child. A sexual assault at a party. All while still a child yourself.

Jenny tells Lily what happened. Once. She tells Lily it’s fine, she’s over it now, she wants the past to be the past.

Maybe Lily should’ve pressed more. But she doesn’t. Because she said those same words on that same couch only a year ago.

She wants to believe Jenny is fine now. She has to believe Jenny is fine now.

Because if Jenny isn’t fine now, what does that say about Lily?

[littletroubledoll]

rich nyc mom aesthetic