Tumgik
#chessy
lawsbiana · 1 day
Text
Tumblr media Tumblr media
Lisa Ann Walter on After Midnight
——————————————————————————————-
babygirl looking so good 😮‍💨😮‍💨😮‍💨😮‍💨
56 notes · View notes
morgana-larkin · 6 hours
Note
HMM,,, if i dare request an either chessy or melissa fic.. with... like them having a breast/lactation kink and when doing the deed- like praising reader and making them suck her tits ETC do whatever u feel is necessary with this if u even want to write it.... :) /// also inexperienced reader and/ or mommy kink....
Dare accepted! I also did a little surprise and did both of them! I don’t see Chessy as having a mommy kink though so I didn’t do that for her. So it’s quite long since I wrote about both and tried to make it as cute as possible. So good luck! Not edited in the slightest and I hope you like it!
On another note: you might have noticed that I added 2 other characters to my masterlist, adult Misty from yellowjackets and Moiraine Sedai from wheel of time. Send prompts for any character on my masterlist! I do it all, angst (with reluctance), fluff, smut, age gap.
Her Good Girl
Warnings: ok there’s a small list. Breast kink, mommy kink, praise kink, so much fluff, semi public smut, smut
Words: 6.9k (I have no regrets)
Tumblr media
Melissa
“When are you gonna ask her out?” Barb says to Melissa one morning.
“Ask who out?” Melissa says, even though she knows exactly who Barb is talking about.
“She means y/n.” Janine pipes up and Melissa and Barb turn to the trio.
“Ya, I mean you guys are so flirty I’m surprised you aren’t already together.” Jacob says.
“It’s really obvious.” Gregory adds and Melissa turns back around and face Barb.
“What they said.” Barb says.
“I just, I’m not ready.” Melissa says. “Where is she anyway? She’s usually here by now.” Melissa adds as she sees the time.
20 minutes later they all get up to go greet their students and Melissa sees you’re still not here. They walk to their classrooms and then Melissa sees you coming in the front door in a hurry and your hair is wet.
“If you’re not gonna ask her out then at least put the heart eyes away.” Barb teases her as Melissa looks at you longingly and with soft eyes.
You end up catching up to them as you all make your way to your classrooms. “Hey you two.” You tell them.
“Hey hun.” Melissa says right away.
“Morning sweetheart.” Barb says after looking at Melissa with a smile and shake of her head.
“Running late this morning?” Melissa asks you.
“Ya, I forgot to set my alarm clock and woke up 40 minutes ago. Took the world’s fastest shower and didn’t have time to blow dry it.” You tell her. You then both say bye to Barb as you reach her class then you both continue on to yours.
“Well I think you still look good, wet hair or dry.” She tells you with a smile.
“Thanks.” You tell her. Unknown to you is where Melissa's mind is wandering right now seeing your hair wet. Things the two of you could do in the shower. Then Melissa takes a deep breath and tries to think of other things to calm herself as she feels herself getting wet between the legs and it’s not even 8am yet.
“Did you have a coffee?” She asks you and you shake your head.
“I’m gonna get a headache from the caffeine withdrawal until lunch.” You say with a pout.
“Well here, I still have half left. Take the rest of mine.” She tells you and hands you her mug.
“Oh no, that’s your coffee, you should have it. I’ll just power through until lunch.”
“Hun, I’m offering it to you. Just take it, I had enough for the morning.” She tells you.
“Are you sure?” You ask and she nods with a smile. “Alright, if you insist.” You say and you take her mug and take a sip. You hum at the taste of the caffeine and you smile.
“Do you want to go out with me?” She asks as you reach your classroom. You choke on the coffee and begin coughing. She pats and rubs your back until you stop.
“What?” You ask her, you didn’t know if you heard her right.
“Do you want to go on a date with me?” She repeats and you smile at her.
“Yes, I’d love to.” You tell her and she beams.
“How does this Saturday sound?” She asks you.
“Sounds perfect.” You tell her and kiss her cheek, she blushes and touches the spot where you kissed her cheek and smiles.
*7 weeks later*
It’s Saturday night and you’re both cuddling on her couch, finishing the movie. The credits roll and you reluctantly pull away from her and stretch and yawn.
“I should probably get going.” You say and stand up.
“Alright hun. Will I see you tomorrow?” She asks you and you nod. She gets off the couch and goes to where you’re gathering your things near the door. You stand back up and you look at her. You lean in and give her a quick peck, then you give another and another. Then you keep your lips on hers and end up making out with her. At some point you end up moaning and she pulls away. “As much as I would love to keep kissing you, your moaning is gonna make me want more.” She tells you.
You told her you were a virgin 3 weeks ago when she asked you if you wanted to have sex and she told you to let her know when you were ready. You felt so lucky to have her, she was so patient and understanding with you. You leaned in and kissed her again and she pulled back after 2 seconds before it could continue. “I’ll see you tomorrow hun.” She tells you. You were about to put your shoes on when you looked at her again, her smiling at you and you realised, you’re ready now.
“Actually, I think I’d like to stay.” You tell her and she quirks an eyebrow at you. “I’d like to stay and keep kissing you.” You tell her and walk towards her and put your hands on her stomach gently. She flinches and looks shocked and then you start moving them up, towards her chest. She stops your hands by grabbing your wrists and looks at you, still holding your wrists.
“Hun, what are you doing?” She asks you and you smile at her.
“I’m ready, and I want you right now.” You tell her and she still looks at you.
“Are you certain? Like 100% certain?” She tells you.
“Yes, I want you to be the one that takes my virginity Mel.” You tell her and she smiles.
“Then come to my bedroom.” She tells you and makes you go first. You walk upstairs and as soon as you make it to the top. She spins you around and kisses you, and then picks you up and places your legs around her waist. She carries you the rest of the way to her bedroom and she gently places you on the bed. She goes to close the door and then makes her way back to you.
You scoot up a little further on the bed and Melissa crawls on top of you and kisses your lips. She grabs the hem of your shirt and then pulls back to look at you and you nod. She takes your shirt off and she looks at you. “God you’re so beautiful.” She tells you and you bring her back to kissing you. She trails down to your neck and kisses your neck then begins sucking on it and you gasp and arch your back. Melissa sneaks her hand under you and unclips your bra. She takes it off with your help and she throws it somewhere on the ground. She switches to the other side of your neck and she cups both of your breasts in her hands and squeezes them. You moan at that and she smirks before trailing down again to your chest and places kisses all over your chest before placing her mouth around a nipple. You grab her hair when she places her mouth on a nipple as the feeling is heavenly.
“Omg Mel. That feels so good!” You tell her and she smirks, you don’t see it but you feel it. After a minute, she switches to the other nipple and you buck your hips. After another minute of her swirling her tongue around on your nipple and sucking it, she pulls away and moves down. She takes your pants off with little effort and she places her fingers on your underwear then looks at you for confirmation again. You nod your head and she slides your underwear off slowly, just enjoying seeing your whole body without anything on it, and she’s the only privileged one to ever see it, and that makes her happy. She rubs her hands up and down your legs and thighs, just feeling your entire body. She lies down to place her mouth on your clit when you speak up. “Wait.” You say and she stops immediately and looks at you. “I want to see you too. I’m completely bare here and you still have all your clothes on.” You tell her and she grins.
“I know, that’s how I like it. But don’t worry, you’ll see my body as well. After I pleasure you first.” She says with a wink and you blush. “Are you ready?” She asks you and you nod. She wastes no more time after that, she dives down to your clit and starts swirling her tongue on it and you moan out at the feeling and you grab her hair again. She then goes lower to your entrance and you gasp. “Oh Amore, you taste so good.” She tells you then sticks her tongue in your entrance and you gasp loudly. She takes her tongue out then immediately sticks it back in again and repeats for a couple minutes. She pulls back and you whine, “have you touched yourself before?” She asks you and you look at her.
“Only with a vibrator.” You tell her and her eyes shine at that.
“So you’ve never fingered yourself?” She asks and you shake your head. “Oh Amore, I feel so privileged.” She tells you and you blush. “I’m going to stick my finger in but if you want me to stop then let me know ok?” She asks and you nod. “It might hurt a bit at first but that’s because you’re not used to it.” She says and you nod again. She starts playing with your clit and you buck your hips and she lined her middle finger up with your entrance and she slowly inserts it. You gasp out when she’s entering and then when it’s in all the way, you moan. It does hurt a bit but she stays there until you nod at her to tell her the pain stopped. She slowly slides it back out then slides it right back in again and you begin to moan again.
“Can you go faster?” You tell her and she smiles and speeds up. You gasp and grab her hair. While she’s still fingering you, she leans down to you and kisses your lips. Her thumb goes to your clit and you gasp in her mouth and she slides her tongue in and you moan. She slows down and slides a second finger in and you arch your back and gasp in the kiss again. You feel you're close to coming and your legs start to shake and Melissa notices.
“Oh baby, are you close?” She asks you and you nod. “Do you want to cum for mommy?” She asks and you don’t even flinch at the nickname she gives herself, in fact it turns you on even more.
“Yes I want to cum for you mommy.” You say and she grins.
“Then cum for me baby.” She tells you and you come immediately. Melissa slows her fingers down and gently pulls them out. You take a minute to catch your breath and Melissa comes back in with a cloth. When did she leave? She gently wipes your centre then looks at you with a smile. “How was that?” She asks you.
“Fucking incredible!” You tell her and she beams. She comes up to you and cuddles you. After about 10 seconds you go and straddle her lap.
“Something you want Amore?” She tells you with a quirked eyebrow.
“I want you.” You tell her.
“You just had me.” She teases you.
“I want to see your body and touch it and make you feel good too.” You tell her.
“Are you sure? You don’t have to, the first time might be a bit overwhelming.” She tells you and strokes your cheek with the same hand she used to finger you. You grab her hand and stick the 2 fingers she used in your mouth and lick them. She looks at you with so much lust in that moment, you think she might fuck you again. You moan around her fingers and she rubs her legs together. You remove her fingers from your mouth and you reach for her shirt and she nods before you take it off. You look at her stomach and chest and you have to wipe some drool off that slipped out and she giggles. You reach in the back and unclip her bra and you practically ripped it off. Once it’s off, you freeze and stare at her breasts. They’re so big and so soft looking, they’re irresistible, they’re perfect. “Go on and touch them if you want. I like it when people touch them and suck on them. It’s a kink of mine.” She tells you and you immediately cup both of them and then attach your mouth around a nipple and she moans. “Yes baby, just like that.” She tells you and you begin sucking on it and she grabs your hair. “Yes that’s it, suck mommy’s tit.” She says and you moan which makes her buck her hips due to the vibration on her nipple.
She practically traps your head there since she’s holding your hair but you don’t care, you feel like you can spend all day just licking and sucking her nipples.
“Baby, can you be a good girl and suck mommy’s other tit?” She asks you and you immediately pull back and attach your mouth on the other one and start sucking. “Good girl.” She says and you moan. She sees that you like getting praised, she thinks you might have a praise kink. You take her pants and underwear off after you pull back and you look at her completely naked and you blush. “Does my baby like what she sees? Do you like mommy’s body?” She asks as she strokes your cheek.
“Yes mommy, I love your body.” You tell her and she smiles.
“How about you stick your cute little fingers in me and put that amazing mouth of yours back on my nipples? How does that sound?” She asks you.
“I like it.” You tell her and you go to stick your fingers in and realise you have no idea where to put them. Melissa notices this and she guides your fingers to her entrance and you stick a finger in and she moans.
“That’s it baby, put another one in, don’t be shy.” She tells you and you stick another one in and you start sliding in and out of her. You think that she feels amazing around your fingers and you don’t want to ever pull out. She then leans down so her boobs are in mouths reach and you wrap your mouth around a nipple and you start sucking. Melissa starts moaning like crazy and it turns you on and you rub your thighs together. Melissa notices the action and looks at you with a smirk. “Oh, does my baby like the noises that mommy makes for her?” She asks you and you nod. “If you like I can fuck you with a strap after.” She tells you and you nod.
You go and suck on the other nipple and Melissa continues moaning and she is now riding your fingers while you continue to slide in and out of her, matching her rhythm. She grabs your hair and she starts shaking and you look up at her face while still sucking on her nipple.
“That’s it baby, I’m so close, rub my clit.” She commands and you obey. You bring your other hand in between her legs and you find her clit and start rubbing it. Seconds after she comes with a high pitched gasp. She takes your fingers out of her and puts them in her mouth and licks them clean. She moans when she’s licking the taste of herself off your fingers while looking at you. She smirks then gets off the bed and heads to her closet.
“Wait! Where are you going?” You ask her and she turns around.
“Don’t worry, just to my closet. I made you a promise didn’t I?” She says and you look confused. Did she? You can’t remember. She then pulls out a strap and puts it on and that’s when you remember. She walks towards you with it on and you wonder how she can look breathtaking no matter what. She climbs on top of you and puts her hands all over your stomach and chest. “So beautiful, and all mine.” She says softly and you moan. “Do you like being mine baby?” She asks you and you’re back to only being able to nod as you can’t find your voice. She wants to get you more wet to not hurt you as you only ever had a finger in you before and that was 10 minutes ago. She grabbed her smallest dildo but she wants to be cautious. She then remembers that you might have a praise kink, so she experiments with that. “Well, you don’t have to worry baby, you are mine, you’re my good girl.” She tells you and you feel all the wetness from your mouth shoot to your core at her praises. She checks your entrance and sure enough, you’re wet enough now. She lines the strap up and looks at you. “This might hurt a bit baby, but if it hurts too much then tell me straight away ok?” She says and you nod.
She then starts to slide in the tip and you feel it start to fill you. She slides more in and you feel yourself stretch to accommodate it. It does start to hurt a bit but not to the point of being painful, especially if it’s also mixed with pleasure. She slides in fully and you gasp.
“You ok baby?” She asks you, voice full of concern. It takes you a few seconds but then you look at her and nod. “Do you still feel a bit of pain?” You nod at that and she stays still, she does move a bit but only to kiss you. You start to relax and then you notice the pain disappeared and only pleasure remains and you start to squirm. Melissa feels you squirm and looks at you. “Am I correct to assume you want me to start moving?” She says and you nod. She smiles at you then starts sliding in and out of you.
You start gasping and moaning as you feel it slide out then immediately fill you back up. You look at her and of course it’s a goddess that’s making you feel this and you pull her head down and kiss her. Melissa is taken by surprise by it but isn’t complaining, she likes that you get a sudden urges to kiss her, it makes her feel wanted. She smiles into the kiss while she’s sliding in and out of you, then moves a hand down to rub your clit. You gasp into the kiss at the intense pleasure you’re feeling. With her lips kissing yours, her boobs squashed on your body, her finger rubbing your clit and the dildo sliding in and out of you at a fast pace. All that together makes you come fast and strong.
She slides out of you and removes the strap. She goes to get a cloth and cleans you up. You yelp at first due to sensitivity but she makes sure to be as careful as possible and then cleans herself up. She lays down next to you and you immediately seek her body out for comfort and she doesn’t hesitate to hold her arms out and bring you close to her, with your head on her chest.
“Do you like that hon?” She asks you once your body has stopped shaking.
“Ya I did.” You tell her with a huge smile. “Did you?”
“Ya, I loved it.” She says and you yawn. “Get some sleep, I’ll be here when you wake up.” She tells you.
“You promise?” You ask her.
“I promise.” She says and you get more comfortable and immediately fall asleep, Melissa stroking your head and finally feeling like she’s where she’s meant to be. She falls asleep with a smile on her face.
Tumblr media
Chessy
You catch Chessy's attention the first time you came over to the house. You knock on the door and Nick runs over to answer it. When you enter with him, Chessy is walking over to go get Hallie and Annie for lunch.
“Hey Chessy, I want you to meet my sister y/n.” He tells her and she gives him a look. She knew he had a younger sister but didn’t know there was such an age gap. You look to be 15 years younger.
“Hi nice to finally meet you.” She says and you look over at Nick then stick your hand out to shake hands with her.
“Hi, nice to meet you too. Nick has talked about all of you and wanted to finally meet his household.” You say. “Nick, I didn’t know you talked about me, I’m honoured.” You tell him and he chuckles.
“Forgive me for asking, but it seems like there’s a noticeable age gap between you too.” Chessy says and you both look at her and smile.
“Ya, 16 years, but we love each other regardless.” Nick says and puts a hand around your shoulders and you giggle.
“Wow, quite a difference. Anyway, lunch is ready, and Nick mentioned you’d be coming over so there’s enough for you to have some as well.” She says and you smile at her.
“Thank you so much!” You tell her and she blushes. She then scurries away quickly to go get the twins. Nick looked at the interaction with interest. He knows that Chessy is interested in both genders and he knows that you’re interested in women, a bit older women too. You mentioned your type to him before and now that he thinks about it, Chessy fits it perfectly. He decides not to say anything as he’s finally getting to reconnect with you in person again after not having seen you for a few years.
A month goes by and since you recently moved to California to get to know Nick’s family more, you lived in an apartment building about half an hour drive away. You mentioned it to Nick when he says you could drop by more instead of a few times a month. You told him that it’s a lot of gas and you got an apartment to pay for and not a great paying job. He then offered to let you move into the house, rent free and after a little insisting and Chessy telling you that it’s a great idea, you accept.
A couple months go by and you and Chessy spend a lot of time together. The twins notice it and also notices the looks you give each other and of course one of them brings it up and embarrasses both of you.
“Are you guys dating?” Hallie asks you both and Chessy’s cheeks turn red and you choke on your juice as you were taking a sip and start coughing. Chessy immediately goes and gives you a few pats and rubs your back to help with the coughs.
“Hal, why would you think we’re dating?” She asks her and the twins look at each other.
“You mean you’re not?” Annie asks and you and Chessy both shake your heads.
“But you spend a lot of time together, you keep giving each other looks that our parents give each other and you’re constantly being touchy.” Hallie explains and you both look at the twins then you look at each other.
“Ok get out of here you trouble makers.” Chessy says and shoos them away. She then turns back to you when they leave. “Hey I’m sorry abo-hm.” she starts but is cut off by your lips on hers.
And that was the start of many kisses and a relationship.
3 months pass and it’s the summertime and Chessy planned a date with you after Nick gave her time off for it, not knowing you and Chessy are dating.
Chessy brings you horseback riding, you take one horse though and she brings you a good distance away from the house. It’s about a 15-20 minute ride. She then gets off and helps you get down and then ties the horse to a tree then sets up a blanket on the ground.
“Did you take me on a picnic date?” You ask her and wrap your arms around her waist and kiss her shoulder blade.
“Ya, is that ok?” She asks, concerned you might not like it.
“Yes, I love it.” You tell her and she turns around in your arms. You both are the same height so she easily kisses your lips and wraps her arms around your neck.
“You know what I love?” She tells you and you look at her curious, you haven’t said the L word yet, but you know you both love each other.
“What?” You ask.
“You” she says and you smile.
“Well I love you too.” You tell her and she smiles and kisses you again.
You both have a great picnic date as she made both your favourite finger foods and you dive into great conversation.
At one point you feed her a piece of fruit and the juice runs down to your arm a bit and she goes and licks it up right away. You let out a small moan and you jump at her and crash your lips together.
“Woah.” Chessy says and it takes her by surprise, so while she still is able to put her hands on your hips, she still falls back on her back, with you on top of her.
When you pull back, you both stare at each other and Chessy smiles up at you. “Hi beautiful.” She tells you and you blush.
“Hi, sorry about that.” You say at bit embarrassed.
“Hey, don’t be sorry. I liked the surprise.” She tells you and moves some of your hair behind you that’s blocking your face. You look at her and you see the care she has for you and it overwhelms you and warms your heart. You knew she cares about you and you always blushed when she did things for you as you weren’t used to it from a partner.
Chessy knew your past relationships weren’t the best and didn’t last long as you told her about them. When you told her then she wanted to show you how a partner should treat you, with respect and love. She let you set the pace as she doesn’t want to push or pressure you, you told her that you came close to having sex once with a partner but then backed out as it didn’t feel right.
You kiss her again and neither of you pull back. Chessy knows she should pull back now as she’s getting turned on with your body on her like this and you’re making out with her. She doesn’t pull back and accidentally lets a moan slip out and her cheeks go red as you pull back.
“Do you want to have sex?” You ask her confused and Chessy is wondering how you don’t know how you effect her.
“Yes, I have for about 2 months.” She tells you. “But I’m letting you decide when you’re ready and I don’t want to pressure you.” She tells you honestly and you look at her with such love.
You cup her cheek and she leans into your touch. “How did I get so lucky with you?” You say and she hums.
“I feel like I’m the lucky one.” She says. You suddenly look around and you see there’s no one around and then you take your dress off. Chessy looks at you and cheeks go red as a tomato. “What are you doing?” She asks and you smile. You know she won’t do anything unless you tell her you’re ready but you decide to tease her first.
“What you don’t like what you see?” You ask her and you drop your smile, to play the act.
“What? Of course I do, but hon, I don’t think you realise the effect you have on me.” She says and she accidentally moves her hips a bit and rubs her thighs together.
“Well what if I told you I want you to touch me?” You tell her with a lower voice and lean down and scoot down a little bit and push her shirt up enough to see skin. You then lean down more and trail kisses up her stomach.
“Hon, I-”
“I want you to touch me, all. over.” You punctuate at the end and you slide your hands under her shirt and they land on her bra before she grabs your wrists and pulls them out of her shirt. You could tell she’s almost at a breaking point and you push a little further. You lean down and suck on her neck and she gasps. She lets go of your wrists and pulls your head back.
“Hon, please I-” she then freezes when you unclip your bra and take it off.
“Do you wanna touch them?” You ask her and she lets out a whine. “Go on then, I want you Chessy.” And at that she snaps. She flips you both over so she’s on top and she dives right to a nipple and starts sucking. You gasp and moan as she puts that experienced mouth on you and finds out quickly what you like. You take the blue sweater off of her and Chessy takes her top off quickly. She then goes to your neck and leaves hickeys all over your neck and chest. “You know my brother will find out as soon as we get back home” you tell her and she smirks.
“He’ll be happy to know you’re being taken cared of.” She says and rubs her hands up your body, starting at your hips. You grab her head and pull her down to kiss you and you unclip her bra and throw it somewhere. You then undo the button on her pants and pull them down. They don’t go far as you both refuse to break the kiss and you move your legs to try and pull them down. It was rather unsuccessful but it did give her a great opportunity since her legs are now right in between yours. She breaks away from the kiss with a laugh at your attempt and kicks them off. “I know you teased me to see how far you could go before I break and believe me, you’ll pay for it next time, but for now, since this is your first time, I want you to enjoy this.” She tells you and in retrospect you probably should have listened but you couldn’t with her boobs right in your face.
You sit up and immediately put a nipple in your mouth while cupping it with your hand and your other hand around her waist to help keep yourself up. You hum as you suck on it and can’t believe how many times you imagined them and how they would feel and taste, and now you know.
“Do you like them honey? Do you like sucking on them?” She asks when she heard you hum. You nod as your mouth is occupied at the moment and she grabs your head. “Suck on them all you want, baby. Your mouth feels so good on them.” She says and when you give a rather hard suck on them, her mouth hangs open, lost in the pleasure. You spend a good few minutes just enjoying her breasts, licking and sucking on them and enjoying the noises she’s making.
While Chessy is used to her breasts getting attention, she’s not used to this much, and she’s loving it. The men she’s dated as only ever paid like 30 seconds on them and when right to her pussy, the women usually about a minute before right to her pussy. And while she knows you’re both soaking wet right now, she can’t help but feel how good it is to have this much attention on them, it’s a kink she never knew she had.
“Oh my good girl, you’re just in love with sucking on them aren’t you?” She says when you pull away.
“Yes, I just love how big they are. I feel like I can suck on the whole thing.” You tell her and she stops you before you do. She’ll let you next time but for now, she wants this to move along. If you’re anywhere she is right now then you’re soaking wet in between your legs.
“Woah there, baby. You can next time but right now, I’ve been wondering how you taste.” She says and you smile.
“Can I sit on your face?” You suddenly ask as she takes your underwear off.
“What?” She asks. Your question caught her off guard, she knows she’ll accept, she wants to taste you and doesn’t matter to her who’s on their back.
“I heard about face sitting and was curious and want to try it.” You ask and she smiles.
“Of course.” She says to you and you get up while she gets on her back. You go up to her face and you align your entrance with her mouth and then lower yourself on her. The first lick she does and you both moan. She thinks you taste amazing and you think it felt really good and you both want more.
She starts licking all over your entrance and eventually sticks her tongue in and starts sliding in and out of you. You gasp and fall forward but she catches you and keeps you up by holding your waist. You end up bucking your hips and grab and yank her hair by accident as the pleasure is just so good. You feel bad for pulling her hand but she just moans and you think that either she didn’t mind or she liked it. You try again and she moaned again and realised that she likes her hair being pulled. She lifts you up a bit to speak. “You can do whatever you want to me, baby.” She says and then brings you back down on her mouth. Only this time she goes to your clit and you really start bucking your hips. You think that grabbing her hair isn’t enough so you put your hands back and grab her nipples. You squeeze them and she moans which vibrates on your clit and you let out a hitch pitch gasp as it took you by surprise and it felt good. You keep squeezing them as her moaning brings you more pleasure and before you know it, you’re close.
“Oh Chessy, I’m so close.” And she gives you a thumbs up to tell you to let go and cum. You do immediately after and Chessy licks it all up. You then get off of her and collapse next to her.
“Did that take a lot of you, baby?” She asks when she sees you spread out like a starfish and breathing hard, and you just nod. She just scoots up next to you and puts a hand over your chest. You turn to face her and kiss her lips, moaning when you taste yourself on her and that gives you a wave of energy. You take her underwear off and then go back wrapped up in her arms. While Chessy thinks you took them off to be able to feel her body on yours to calm down, you actually took them off to finger her. You bring her leg and put it over yours, then you bring a hand down in between her legs and immediately slide a finger in her entrance. She immediately bucks her hips, gasps and brings a hand to your arm, and mouth wide open. She hasn’t had anything in her in a few years and it feels so good. You add another one and slide them in and out of her slowly at first. “Baby, can you go faster?” She begs and you smile.
“I thought you said I could do whatever I want to you?” You tell her and she whines. Fuck sakes, she did say that.
“Didn’t think you’d make me regret saying it.” She jokes with you between gasps. You take pity on her as she made you feel really good and you want to do that for her. You go much faster and she hangs her mouth open again and gasps like crazy. “Oh god, yes baby, that feels so good.” She says and you risk it and add a third finger in her and she falls back on her back, overcome with pleasure. You put your other hand on her clit and rub it while you lean down and suck her nipple. She ends up leaning on her forearms with her legs spread wide open for you and she starts shaking. “Oh god, oh god baby, I’m so fucking close.” She says and you go and suck her other nipple. She comes immediately as you start sucking. You pull out of her and put your fingers in your mouth and lick them. She looks at you as you do that and as soon as you moan at the taste of her, she pounces at you and you end up on your back and her on top.
She wastes no time in kissing you and immediately sticks two fingers in you and you moan into the kiss. She curls her fingers in you while fingering you and you see stars and have to shut your eyes. She puts her thumb on your clit and rubs in a circular motion and you do a huge gasp and start shaking.
“Let go baby, it’s ok, I’ve got you.” She tells you and you immediately come. She pulls out of you then licks her fingers. She didn’t bring any cloths so the blanket will have to do, and cleans you both up. She the lays down next to you to help you both calm down with skin to skin.
“Hmm, I really enjoyed that.” You tell her and she giggles.
“Well I’m glad. Cause I really enjoyed it too.” She tells you and you smile. You end up getting dressed, packing everything up and get back on the horse after about 20 minutes of cuddling and you head back.
On the way back you get in a little teasing mood and you slip your hand under her shirt to cup her boob and rub her clit through her pants and underwear.
“What are you doing, baby?” She says and makes no attempt to stop you even though she could.
“Teasing you.” You simply say.
“Baby, if you keep at it then I’ll stop this horse and take you against the nearest tree.” She tells you. And you pull away from her clit but you put both your hands on her boobs after unclipping her bra.
“I just love these.” You say and she hums and leans back a bit, leaning into your touch. You both make it back to the house, Chessy nearly took you against a tree twice, and you end up clipping her bra back on. She brings the horse to the stable, she gets off then she helps you off. Once you land on the ground though, you wrap a leg around her waist and kiss her. She picks you up and brings you up against the stable wall and continues kissing you.
“Oh my god! Not what a brother wants to see!” You hear and you both pull back and see Nick there covering his eyes with a hand. Chessy puts you down and goes to put the horse away properly and give him something to eat.
“Sorry Nick.” You tell him and then laugh.
“Ya, sorry boss.” Chessy says and walks up behind you, wraps her arms around your waist and places her head on your shoulder.
“I had a feeling you two were together but I did not want to find out that way.” He complains and you and Chessy giggle. “Are those hickeys on your necks?” He says then looks to the horse and the fact you were gone for 3 hours. “Oh my god, on second thought don’t tell me, I don’t want to know. But Chessy, she is my little sister, so if you hurt her then I will fire you.” He tells her and points a finger at her.
“Well I guess it’s good that I have no plans to hurt her.” She says and gives your shoulder a kiss.
“And y/n, even though you’re my sister, Chessy has been with us for many years, so hurt her and you’ll have to deal with me.” He tells you and you turn to Chessy.
“Well I guess I’m stuck with you then.” You tell her with a huge smile. She responds to that with a hard kiss to your cheek and tickles your stomach and you giggle. You break out of her embrace and run away from her tickles and she runs after you, both of you laughing. Nick watches you run both away and shakes his head with a smile. “Such dorks.” He says out loud.
Taglist: @esposadejoyhuerta
@imaginesmultifandoms
@idonothingalldays-blog
@sexysapphicshopowner
@dvrkhcld
@lilfartbox1
@ricejucie
Let me know if you want to be added!
41 notes · View notes
Text
Tumblr media Tumblr media
she did this for the parent trap babies
6K notes · View notes
arcadiabay · 9 months
Text
Tumblr media Tumblr media
LISA ANN WALTER as CHESSY The Parent Trap (1998) dir. Nancy Meyers
850 notes · View notes
Text
Tumblr media Tumblr media Tumblr media Tumblr media Tumblr media Tumblr media Tumblr media Tumblr media Tumblr media Tumblr media Tumblr media Tumblr media Tumblr media Tumblr media
"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)
2K notes · View notes
philocalistwrites · 8 months
Text
Tumblr media Tumblr media Tumblr media Tumblr media Tumblr media Tumblr media Tumblr media Tumblr media
the power of women
431 notes · View notes
scaredsofmyguitar · 1 year
Photo
Tumblr media Tumblr media Tumblr media Tumblr media Tumblr media
@pscentral anniversary event: get to know the members
↳ Chessy in The Parent Trap (1998)
1K notes · View notes
regalmilfs4me · 3 months
Text
Tumblr media Tumblr media Tumblr media
I’m on my knees Miss Walter🫠🔥
233 notes · View notes
schittspark · 9 months
Text
Tumblr media Tumblr media Tumblr media Tumblr media Tumblr media Tumblr media Tumblr media Tumblr media
comfort movies ► the parent trap (1998)
466 notes · View notes
janeyseymour · 5 months
Text
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
Tumblr media
233 notes · View notes
Photo
Tumblr media Tumblr media
Abbott Elementary 2x4 | The Parent Trap 
2K notes · View notes
lawsbiana · 16 hours
Text
Tumblr media Tumblr media
Lisa Ann Walter - 4/24/2024
THE COLOR GREEN WAS MADE FOR HER
31 notes · View notes
morgana-larkin · 3 days
Text
Masterlist
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
98 notes · View notes
kinglet1963 · 1 month
Text
SHE'S REPOSTED IT TWICE NOW-
Tumblr media Tumblr media
98 notes · View notes
knopeswifts · 2 years
Text
THIS LOOK IS SO CHESSY CODED, THE COSTUME DEPARTMENT KNEW WHAT THEY WERE DOING.
Tumblr media Tumblr media Tumblr media Tumblr media
1K notes · View notes
astrallina · 1 month
Text
miss walter is really out to get them gays, specifically me
// the color and the dress looks so good on her 😩
Tumblr media Tumblr media Tumblr media
80 notes · View notes