#chessy the parent trap

[lot-of-nothing]

Can I Call You Rose? (Ch. 1?)

Chessy x Reader

As the new viticulturist (grape-growing expert) at Nick Parker's vineyard, you fall for a certain nanny. (Post-Parent Trap movie I think)

Warnings: SOFT SMUT (with a little plot and romance)

You wondered if your fingers were going to go numb, or perhaps your heart would just explode first?

You had finally worked up the courage to kiss the auburn-haired beauty mere hours ago and now Chessy’s lips were finally attached to her neck. You had met during your first week as Nick Parker’s head viticulturist. Her warmth was magnetic and you always tried to find reasons to tend to the grapes closest to the house in case you could start a conversation with the nanny. You spent many afternoons together, flirting while she brought you her homemade lemonade or while you walked her around the rows of vines handing her grapes to try. Chessy always seemed to wear a smile when you were near, filling you with butterflies in return. You had been dreaming of this moment since you first met the beautiful woman and now you were filled with pure unfiltered anxiety. 

Chessy’s open mouth kisses to your throat and collarbone were unlike anything you had ever experienced. Were you supposed to crave her as much as you did? There was a fire ignited in the pit of your stomach that hungered for something that felt so forbidden.

As nervous as you were, you wanted more. You needed more. You wanted to feel Chessy’s hands setting every inch of your skin aflame… but the thrum of energy winding through every cell in your being had you wondering if you would have a panic attack or pass out before that could happen. 

“Hon… Hon? Honey!” 

You must have spaced out entirely as Chessy’s voice drew you back to reality. Next thing you knew, Chessy’s hands were now cupping your face, staring intently into your eyes. 

“Hm?” You hummed, your eyes brimming with tears as you felt like you could finally breathe again. You felt incredibly embarrassed that you felt that you couldn’t handle the physical intimacy. It was hard when you were so in love with Chessy and lacked the experience you thought necessary to please her.

“Are you okay, sweetie?” Chessy’s voice was just above a whisper. She was terribly worried that she had pushed the bounds of your relationship too far too soon. Little did she know that it would be your own slip up that would be the culprit of a ‘too much too soon’ relationship. 

“I-I-I…” You quickly stopped herself short, not wanting to make yourself cry.

“It’s okay… Wanna finish our movie, honey?”

You shook your head furiously, determined to push yourself through the anxiety and nerves.

“Honey…” Chessy seemed skeptical, her hands squeezing your cheeks. The extra bit of care Chessy showed was all you needed to lose your head, tears pooling in your eyes and spilling onto your cheeks.

You stared into your hands, trying to explain to Chessy why you were struggling to get through your anxieties. “I just… don’t- I just don’t know how to pleasure a woman…” 

“Tell you what. Come’re…” Chessy cooed, drawing you in so you could sit between the auburn beauty’s legs. From there Chessy gently caressed your arms, speaking in a firm but gentle tone. “I am going to turn on a different show and you are gonna sit right here and enjoy it, okay?”

You sniffled and nodded, reclining back in Chessy’s arms as an attempt at relaxing. A few moments passed of Chessy tapping away on her phone. The audio sounded off before you even comprehended what was playing, “I hope you are nice and wet for me.”

You certainly weren't expecting Chessy to stream a guided masturbation from her phone onto the television. 

Your cheeks flushed a deep red, “Wha-?”

Chessy’s hands fell to your sweatpants, pulling out the band a couple of inches as she spoke, “I want you to just relax. Just do what she tells you to, okay?”

Your hand was shaking as you pushed it into your sweatpants, never having experienced anything like a guided masturbation before. While daunting, it was incredibly hot.

The audio rang over the tv speakers once more, causing butterflies to swirl in your stomach, “Now, why don’t you see how wet you are for me? Slip your fingers in your panties for me.”

As you slipped your fingers in your underwear, you let out a whimper at first contact with your cunt. What else would you be in for with this nanny? What other tricks were hidden up her sleeves to drive you wild? 

Even though all of your building anxiety, you had grown incredibly wet from Chessy’s touch. You rolled your head back onto Chessy’s shoulder, earning a kiss to your temple as you did. Chessy’s voice was gentle in your ear, “You are doing so well, honey.”

The video instructed you once more, telling you to focus on your clit. Considering the pacing of the video, Chessy must have found a video long enough to help you relax, but short enough that she could find more involvement in your pleasure sooner rather than later. 

Doing as you were told, you circled your clit and felt yourself melting back into the auburn beauty’s arms. What you couldn’t see was Chessy’s smile as she felt the tension in your body fade. Her hands wound up your front, working your t-shirt up your torso to access your breasts.

The audio emanated from the tv was filled with the performer's moans, but you were becoming enraptured by the soft, encouraging hums from the woman behind you. Chessy’s hands drifted up and down your stomach, stopping at your breasts to give a gentle squeeze before shifting back down once more. 

“Let me hear you, sweetie…”

You bit your bottom lip and turned your face into Chessy’s neck, unsure if you were ready to be heard. 

Without a response, Chessy hummed disapprovingly, her hand slipping its way into your sweatpants and then underwear in search of your wetness. At the feeling of her fingers mingling with yours in your cunt, you withdrew your hand and dropped it to your side to allow her to take over. You couldn’t keep yourself from softly sighing at the feeling of her gentle fingertips working against your clit. 

“God, you are so wet…” Chessy whined at the way your wetness coated her fingers. 

You bucked your hips up into her hand, desperately wishing for this sensation to last forever. With her arms around you, fingers dancing around your clit, and her hot breath against your neck, your head was spinning. You couldn’t help but moan before blurting your thoughts to Chessy, “You- you’re so beautiful…” 

“Mmm… thank you, honey.” Chessy cooed, her arm winding around your waist to cradle you close as her fingers continued working against you. Your entire being was set aflame by Chessy’s loving embrace and skilled fingers. 

Your breathing rate was growing faster and faster, the coil in your stomach tightening as you grew closer to your orgasm. 

Chessy’s teeth nipped at your earlobe, tenderly nibbling as she added extra pressure as she circled your clit. Her voice came as a soft whisper, forcing warmth to spread across your face. “I can feel you getting close. You are so beautiful when you fall apart like this for me.” 

“Fuck, I love you~” You exhaled, not registering your words while your hands clung to her forearm. 

Sadly, you were too lost in the throes of your eminent orgasm to notice her lack of a response. She only nuzzled you with her cheek and held you tight as your orgasm washed over you.

Your back arched and your hips thrashed, unable to contain yourself. Your eyes squeezed shut and you let out a lengthy moan, trying to enjoy every ounce of the orgasm Chessy guided you through. 

Chessy sighed with a soft smile and withdrew her hand from your pants. She was trying to ignore her own anxiety building from her lack of response to your omission of love. While she felt she loved you as well, it all felt like too much too soon. In years past, she had dove head first into relationships and had only been burned in return. She had no intention of ruining your relationship over the omission of her own feelings. 

“How do you feel?”

“Mmm… good.” With a deep breath, you roll over in her arms, pressing your cheek near the base of her sternum. You tucked your hands under her wide hips and enjoyed the feeling of your bodies pressed together. “How do you feel about me returning the favor?”

Chessy pushed her anxieties deep down, not wanting to ruin a perfect moment. She had been falling for you since you started at the Parker estate. “Maybe in the morning…”

“Are you sure? I would love to-”

There was that word again. It made Chessy’s stomach drop. 

“No. It’s really okay. We could just… finish our movie.”

She seemed curt in her reply. It lacked the typical warmth you always received from her. It made you terribly self conscious until her hands wandered to the skin of your back, drawing loopy circles with one hand while her other turned the tv back to your movie.

“Mmm… you better be careful or I’ll fall asleep.” You murmured, testing the waters of how likely it would be for you to spend the night with the nanny. 

“Whatever shall I do. I would hate for someone so cute to be in my bed when I woke up.” Chessy was being incredibly sarcastic, her hands continuing to scratch your back in lazy loops. 

You allowed your own hands to wander her hips and thighs as a different form of self-soothing. You obsessed over the soft dips of cellulite and the slopes created by the widening of her hips. Her baggy clothing hid the curves you wanted to memorize through all of your senses. 

Chessy’s eyes drifted shut as she pushed herself to enjoy your loving touch. It was hard for her to accept such unadulterated affection, but she desperately wanted to try. It felt so good for her to be wanted and desired, but the vulnerability required for a deep and meaningful relationship lurked in the back of her mind. 

[taylorkellyreporting]

she did this for the parent trap babies

[arcadiabay]

LISA ANN WALTER as CHESSY The Parent Trap (1998) dir. Nancy Meyers

[lawsbiana]

SHE IS THE MOTHER OF LESBIANS!!!!

I still remember her excitement when i gave her the shirt. She is such a sweetheart. Her heart is definitely made out of gold.

[notsosecretlyalesbian]

"At a time when my life felt scattered and incomplete, the fantasy world of The Parent Trap, and the warm and maternal presence of Chessy, provided me with a dream of gluing the pieces of it together. The film, though not explicitly queer, still provides a sort of utopia of queer acceptance, connection and love. [...] Some days I still think that maybe all I need is a hug from Lisa Ann Walter and I will be all right." - Michael Elias (x)

Lisa Ann Walter as Chessy in The Parent Trap (1998)

[scaredsofmyguitar]

@pscentral anniversary event: get to know the members

↳ Chessy in The Parent Trap (1998)

[morgana-larkin]

Masterlist

(Requests Open)

Melissa Schemmenti

Worth It - Part 1 Part 2 Part 3 Part 4 Part 5 Part 6 Part 7 Part 8

Don't Let Me Go

The 3 3 3 Method

Little Droplets of Relief

Her Poco Sole (little sunshine)

Let Me Help You

Caught On Camera

Overwhelmed

Grocery Store Rendezvous

Thank You for Letting Me Be Myself

Want You Back - Alternate Ending

Map Of Your Scars

Green Isn't Your Colour- Part 1 Part 2

Safe Word

The Game of Love

Mine - Part 1 Part 2 Part 3

Spring Is When Love Blooms

The Stolen Parking Spot

Blood As Green As Her Eyes - Part 1

Teaching You

It Starts With Zero

Fine Line

Make Up and Make Out

Chessy

Music Of Her Heart

Making You Hers

Spring Is When Love Blooms

Marilyn Thornhill

Coming Soon

Misty Quigley (Adult)

Coming Soon

Moiraine Sedai

Coming Soon

[schittspark]

comfort movies ► the parent trap (1998)

[janeyseymour]

if lisa ann walter thought she had a big lesbian following because of chessy, she’s in for it when she realizes that melissa schemmenti is also a gay icon

[livelovecaliforniadreams]

Abbott Elementary 2x4 | The Parent Trap 

[kinglet1963]

SHE'S REPOSTED IT TWICE NOW-

[knopeswifts]

THIS LOOK IS SO CHESSY CODED, THE COSTUME DEPARTMENT KNEW WHAT THEY WERE DOING.

[astrallina]

miss walter is really out to get them gays, specifically me

// the color and the dress looks so good on her 😩

[lawsbiana]

Lisa Ann Walter on After Midnight

——————————————————————————————-

babygirl looking so good 😮‍💨😮‍💨😮‍💨😮‍💨

[philocalistwrites]

spontaneously combusting (real)

[shslbunnylover]

★★★𝙃𝙚𝙧 𝙨𝙣𝙤𝙬 𝙖𝙣𝙜𝙚𝙡 (12 𝙙𝙖𝙮𝙨 𝙤𝙛 𝙁𝙡𝙪𝙛𝙛𝙢𝙖𝙨 𝘿𝙖𝙮 6: 𝙎𝙣𝙤𝙬𝙗𝙖𝙡𝙡 𝙛𝙞𝙜𝙝𝙩)★★★

Character: Chessy

Taglist: @inlovewithgreta @lilfartbox1 (Message me to be a part of the taglist until I get a page set up!!)

Trigger warnings (DL, DI): N/a

Genre: Fluff

A/n: Day 6! Can't believe we're half way done!

Word count: 1.5k

...

...

"Annie! Hallie!" Chessy exclaimed, tripping over her feet as the twins ran past her into the field of snow that covered the yard of the ranch, placing her hand over her heart.

"Sorry Chessy!" The twins exclaimed simultaneously, running throughout the snowfield, picking up clumps of the snowfall in their hands and throwing it in the air out of childlike joy.

"It's fine girls," The housekeeper rolled her eyes with a smile, placing a beanie on her auburn hair before following the girls outside.

You watched from the window, your eyes focusing only on the woman watching over the twins with a smile, pausing your movements that were focused on crochet blankets for the girls' Christmas presents.

Chessy somehow always seemed majestic and gorgeous in your eyes, and the way she stood out in the snowfall right at that moment just had you drawn to the housekeeper.

Looking at her closely, you took in her appearance. A thick pair of gray leggings, a puffy black coat, brown boots, and her matching beanie and scarf complementing her red hair and green-blue eyes.

"Y/n?" Elizabeth asked, walking up to you as she sat next to you. "Are you alright?"

"Oh, yes Elizabeth, I'm alright," You looked up at your boss, who slowly had become your friend since she hired you to be her driver.

"Which pretty site are you looking at?" The blonde smirked, gesturing to Chessy before she took a sip of her coffee, making sure not to spill any on her cardigan.

"The snow..." You blushed, looking down at your lap before beginning to crochet the blankets once again.

"Are you sure it's not anything else?" The older woman asked, looking at you with a slightly knowing gaze. "You know you can just go down there and play in the snow, she'll enjoy it,"

"I-I don't know," You sighed, placing your Crochet Needles on your lap aggressively, leaning your head back with a slight groan.

"Just do it, go out there and take a chance, you know Martin is eyeing her up," Elizabeth looked at you.

You remained silent, biting your lip slightly as you looked at the girls outside.

"Alright..." You muttered, dropping your stuff on the nearby table and grabbing your coat, wrapping it around your body before entering the cold outside to see the girls throwing snowballs at Chessy.

"Y/n! Come help us!" Annie exclaimed, grabbing a ball and throwing it straight at Chessy's face.

"Agh-!"

"Yeah come on Y/n!" Hallie exclaimed as she was busy rolling up the snow for Annie.

Chessy looked over at you in between her snow-covered eyelashes, and you noticed a slight rosy tint coming to her cheeks that you only assumed to be from the cold.

You stood there for a moment, biting your chapped lip as you looked at the girls and then at Chessy. You looked over at Hallie, and you took a step forward, leaving a trail of footprints behind you.

"I think a 3v1 isn't a fair game, is it girls?" You smirked, putting your hands on your hips as you ventured further into the snow.

"Well not really," Annie looked at Hallie.

You chuckled softly, walking over next to Chessy and brushing the snow off of her face.

"Thank you, Y/n," She smiled. "These little rascals have some pretty good aim,"

"Well..." You chuckled mischievously, grabbing a large chunk of snow and forming it into a ball. "Why not fight back?"

"Snowball fight!!!" Hallie exclaimed, hitting you straight in the shoulder with a small snowball, only to be met with a hit to the stomach with your snowball.

Chessy looked at you, surprised by your throwing skills.

"How'd you-"

"Don't question it," You brushed her off.

Chessy narrowed her eyes before squatting down to form the snowballs for you, as she knew you had a better aim than her.

"Bring it on kiddo!" You shouted, taking a ball from the older woman and tossing it at Annie, who was now participating in the fight.

Annie quickly ducked, throwing a snowball at Chessy, which the housekeeper dodged as well. You grabbed a pile of snow and threw it at Annie and Hallie, watching as it distracted them before you threw a ball straight at Hallie's face with a smirk.

"Dang it!" The older twin groaned, getting down on her knees to create a giant snowball, running it through the snow as the sphere expanded.

"You're going to get it now!" Annie yelled, falling into the snow to duck the incoming shot at her.

What you didn't see, however, was the wink that the twins shot each other.

"Hand me one Chess," You looked back at her, shooting her a wink as you grabbed the snowball, throwing it at Hallie.

"Annie, I need help! Distract them!" The older twin exclaimed, running with the snowball in her arms.

You looked over at Hallie, your eyes widening as the snow Annie threw covered your face and blinded you a little.

"Y/n!" Chessy yelled as the giant snowball Hallie had created hit the both of you, knocking you on top of each other.

You sputtered the snow out of your mouth, rubbing your gloved hand over your face, a blush scattering across your face once you made complete eye contact with the woman you were on top of.

"T-Time out!" You squeaked in embarrassment as Chessy sat up, leaving you sitting on her lap, too flustered to hear both girls running off to warm up inside (and spy on you two).

"You okay?" The housekeeper asked, holding your chin to check for any wounds.

"No, I'm fine- I fell on you, are you okay?" You shook the snow out of your hair.

"I'm alright, I had a comfy landing," Chessy chuckled, patting the thick and fluffy snow next to her.

"That's good," You smiled nervously, looking over at your hand that was overtop of hers, the pink on your cheeks increasing.

"Yeah..."

You both looked at each other with nervous expressions on your faces, thoughts running through your heads faster than the both of you could process.

"Chessy I need to tell you something, at least before I can't tell it to you anymore-" You blurted out, tightening your grip on her hand.

"What is it?" She asked, her gaze shifting to your intertwined hands.

"I'm...I'm in love with you..." Your voice trailed off.

"Oh-" Chessy paused, unable to say anything else due to shock.

"I'm sorry I'm gonna head inside," You muttered, standing up to leave before you felt a tight grip on your arm.

"No you're not," Chessy looked at you with determined and loving eyes, pulling you down onto her again before she pressed her lips against your own, generating a comforting warmth in contrast to the frigid weather outside.

Your breathing staggered as the older woman pulled a soft whimper from your lips, savoring the kiss as if you'd never get another one.

Once she pulled away, a silence encompassed the space around you, leaving the only sound nearby being the two of you gasping for air.

"Chess... I thought you liked that guy Marvin or whatever his name is..." You whispered, your lips trembling softly.

"Y/n, I love you too much to love him, I love you and only you," The aquamarine-eyed woman confessed, looking at you with a soft smile and adoring eyes as she pressed her palm against your left cheek.

"Really?"

"Yes, you're such an amazing person, I love you," She assured you, looking at your blushing cheeks.

"I-I love you too Chessy," You said with a grateful smile before you pulled her into a deep kiss, the snow around you falling gently on your bodies, the cold crystals no match for the warmth in your hearts.

...

If you enjoyed reading this, don't forget to like, reblog and comment! Thank you and you are loved <3

-Akira