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Encaptured

Summary:

Jason and Lily have been best friends for years. At the beginning of one long summer, he puts in action his plan to slowly condition her into a devoted, sex crazed girlfriend.

Notes:

Really sexually frustrated in quarantine so here's a long smutty fic to help us get through it. It's gonna follow Jason's meticulous conditioning of Lily through a mixture of manipulation, drugs and lies. Hope you enjoy it as much as I do, leave requests in comments.

Chapter Text

Jason is sitting at the top of the bleachers, watching her carefully. The crowd is a heavy, sweating mess of teenagers cheering on the football team, and everyone else’s eyes are on the players doing victory laps around the field, but Jason doesn’t give a shit about them. He’s here for Lily only. She’s at the front of the cheerleaders, dark hair shining in the sun, her brilliant blue eyes shining with glitter, full lips pulled into a smile. Those dimples are so fucking cute. She’s in a crop top and tiny flippy skirt, with long tanned legs stretching down to pristine white shoes. He wants her legs wrapped around him, glistening with sweat, the jumping muscles standing out under the rippling swathes of smooth skin. He can’t wait for when that becomes a reality.

He’s been best friends with Lily for years. She’s two years younger than him and they’re polar opposites in all their interests, opinions, and other friends, so really the only reason she’s still friends with him is because of their long history. But he moved an hour away to college last year and they’ve been spending a lot less time together. Jason is visiting after six months away, just before her high school breaks up for summer, and here she is looking completely different to last time he saw her—he could’ve sworn her tits have doubled in size, and the sight of her rounded butt when the skirt flips up is making him drool. The changes are perfect, because Jason’s carefully formulated plan is finally being put into place. No more watching her from a distance and lusting over her. This time she’s rightfully his, and she’ll stay that way forever.

The match is finished and everyone is spilling out onto the field. Roy and Michael—Jason’s college roommates, who have met Lily a few times so also came to see the match—get up with Jason and they all go down together to meet Lily at the corner of the field, as agreed. She hugs Jason as soon as she sees him. “Hey Jace! Did you like my routine?”

“You were great,” he assures, ruffling her hair. She bats him away but smiles, as usual grateful for the affirmation. Lily is insecure but beautiful, which is really a perfect combination. “We’re driving back to mine and we’ll have pizza and a movie night. I cleared it with your dad, he’ll come pick you up in the morning. Does that sound good?”

“Yes, perfect,” she grins. She waves goodbye to her friends and then Michael, who drove them, leads everyone back to his car. There are five seats in the car, but Michael’s guitar is taking up two of the back seats, so only three seats left for four people. Michael asks Lily apologetically to sit on Jason’s lap for the hour long journey back. Her and Jason have known each other a long time, so she hesitates only for a second before agreeing.

They start driving with Lily on Jason’s lap, his jeans and her thin cheerleader skirt the only thing between them. She leans back against him and he puts his arms around her bare waist, loving how her skin feels. His hand is lying casually on top of her thigh, and he wishes he could just slip a hand underneath the skirt. But no, not yet, not until the plan is underway. Roy, in the front seat next to Michael, passes back two beers. They play a drinking game to do with the colours of cars that pass by, but a game with rules that seem to mean Lily is always losing, so she goes through five beers while the others are still on their first.

They pull into the drive of their house. Jason’s father became a multimillionaire last year and Jason, as his only son, has seen a lot of benefits from this. Instead of a shitty student flat, he and his friends have been treated to a huge house that they don’t have to pay for, on top of the huge allowance Jason already gets. They get out of the car and Lily is stumbling and giggling, leaning on Jason’s arm for support. “Are you drunk off beer?” he teases, leading her up to the house.

“Never,” she asserts, grinning foolishly.

“If you say so,” Jason rolls his eyes.

The house is darkly lit. Lily kicks off her shoes in the hallway as the Jason lock the door and Roy and Michael disappear upstairs. “Jace, I love your house,” she says. “It’s a lot nicer than mine.”

“I know,” Jason laughs. The apartment that she and her dad live in is practically falling apart, and if the plumber does his job, should be flooded by tonight. “Shall we order some pizza?”

“Yes please!” she says cutely. They go up to Jason’s bedroom and she crawls onto his king bed as Jason picks up the phone to order pizza. He fetches a bottle of wine from his drawers and opens it, handing it to Lily. They put on a movie and pass the wine between them. Jason sips very occasionally, while Lily is taking larger and larger gulps, but she doesn’t seem to notice. The pizza comes and Lily nibbles at one slice before complaining that she’s sleepy and wants to go to bed.

“What about pyjamas?” Jason frowns.

“I forgot to bring any,” she says sheepishly.

“It’s okay, I bought you some,” he smiles. He shows her a little lace nightdress, slightly too small for her. “Is this okay? I had to guess the size.”

“It’s pretty, thank you!” she smiles. He turns away as she strips out of her cheerleader outfit and puts the nightdress on. As predicted, it’s too short, falling only a few inches down her thigh and tight across the chest. Lily doesn’t care and gets under the covers while Jason dims the lights. He changes into a pair of shorts and gets in next to her. He puts an arm around her and pulls Lily in close to him. She’s drunk enough not to complain. “I missed you, Lily,” he whispers in her ear.

“I missed you too,” she yawns. She’s half asleep now.

“Are you comfortable?” Jason asks, tightening his arms around her.

“Comfy,” she responds sleepily. He reaches down and pulls one of her legs up over his, so she is wrapped around him. The nightdress isn’t covering much anymore. He trails his hand down her waist and lightly squeezes her butt, pushing her into his crotch. She moans slightly, melting against him. He moves his hand in between her legs, touching her panties.

“Lily, why are you wet?” he asks.

She mumbles something back at him, completely out of it. Her eyes are shut and breathing is deep and regular. Jason moves her panties aside and strokes her gently, running his fingers up until he finds her clit, and then massaging it gently. She starts getting wetter, her breathing becoming slightly more ragged. He rocks against her, his hard dick grinding into her softness. It feels amazing. He’s planned for this so much, but having her actually in his arms feels unreal. He slips a finger inside her.

“Hey,” she murmurs. He stills. She shifts, rocking against him. He crooks his finger inside her and she melts further into him, her leg tightening around him. He starts pumping his finger slowly in and out, with Lily giving slight moans. Can he fuck her? God, he wants to fuck her. But there’s a plan. He needs to stick to the plan. He keeps stroking her, whispering in her ear and telling her what he’s going to do to her, and all the pleasure that she is in for.

---

Lily wakes up and at first doesn’t remember where she is. She’s lying in a luxurious bed with the warmth of someone on her back, and the light from the sunrise is coming in through the window. She sits up and looks around the huge room, lined with mirrors and doors leading to walk in wardrobes, and finally sees Jason lying down next to her. Oh, right. She’s wearing a nightdress that she doesn’t remember putting on, but has rolled up all the way to her waist. She blushes and hopes Jason didn’t notice, changing quickly into the skirt and jumper she bought to wear today.

Her dad is picking her up this morning but she never asked what time. She looks around for her phone but can’t find it anywhere, so even though Jason looks so peaceful lying in bed she shakes his shoulder to wake him up. “Morning, Lily,” he yawns, sitting up. “You’re up early.”

“Yeah, I can’t find my phone. Do you remember where I put it?”

“No,” he frowns. “Actually, I don’t remember you on it at all. Are you sure you bought it?”

“Of course,” Lily says, but then frowns. She brings her phone everywhere, but she can’t remember having it since before the cheerleading. She thought she put it in her bag and took it in the car with her, but surely she would have checked it in the car, and she can’t remember it going off at all. Her whole memory is quite blurry from yesterday—probably those beers. She always overestimates her alcohol tolerance. It is very plausible that she left her phone in the changing rooms before the match and forgot about it until now. Jason helps her check downstairs and the car, but it’s not there, so she resigns herself to look for it when she gets home.

Jason lets her borrow his phone to call her dad. She calls and he’s drunk, as normal. She sighs irritably. “Dad? Aren’t you coming to pick me up?”

“No, you can’t come home,” he slurs.

“What are you talking about?” she asks irritably.

“Flood… there was a flood. Bathroom leaked. Sewage everywhere. Landlord wants us out. I’m staying with Uncle Dean til we get a new place, so when you get a lift home come here.”

Lily feels her stomach drop. Uncle Dean is a creep who always corners her in empty rooms and tries feeling her up. She can’t stay with him, and it will take forever for her drunkard father to find a new place. The phone is on speaker and Jason is looking at her sympathetically.

“Do you want to stay with us?” he offers. “I wanted to see some more of you any way, and we have a spare room.”

She hesitates, as she doesn’t want to impose, but she really can’t stand Uncle Dean. “Maybe just a few days. Thank you,” she says gratefully. She turns back to the phone. “Dad, I’m gonna stay with Jason a while more. Is that okay?”

“Don’t give a fuck,” her dad tells her, and hangs up.

Jason looks at her sympathetically. “I’m sorry. He’s a dickhead.”

“Yeah, I’m used to it,” she shrugs, but her eyes are smarting when she walks into the kitchen. It’s extra humiliating to be treated like shit in front of Jason, who seems to have had everything handed to him his whole life.

She makes toast and butters it while Jason uses his expensive coffee machine to make cappuccinos for them. He makes fancy designs out of frothed milk on the top, a heart and a star, and she laughs delightedly. “You should be a barista!” she tells him.

“I probably am, in another life,” he tells her, going to fetch the jam. She stirs a spoonful of sugar into her cappuccino, breaking the points of her star.

“Hey, I don’t take sugar,” Jason frowns, snatching the sugar away from her.

“I know, I just put it in mine,” she explains, pushing the other cappuccino towards him.

“No, no, the one with a heart is yours,” he says, pushing it back to her. He takes her sugary cappuccino. “It’s fine, I’ll just have this.”

“You’re so strange,” she smiles at him, mildly confused, but not enough to push it. Although, it’s things like this which make all her friends think Jason is a creep.

Jason sits down opposite her on the kitchen counter and they chatter over breakfast. Lily’s coffee tastes way too bitter, which might just be her hangover, but Jason is insistent on her drinking it so she adds spoonfuls of sugar and makes herself finish it so she doesn’t hurt his feelings. They talk about what they’re going to do while she stays there. “We have to catch up on lots of TV shows. And we’ll go for walks around the countryside, it’s only a short while away and it’s beautiful here. And we’ll probably see Roy and Michael occasionally. You like them, right?”

“Yeah, they’re nice,” Lily nods. “Where are they now?”

“Probably asleep,” he laughs. “I imagine they’ll sleep a lot. But not us, we’re going to be very busy.”

“I’m excited,” she grins. “I haven’t spent time with you in ages.”

“I know, I missed you a lot.”

“I missed you too,” Lily says, with honesty. Jason might be a little strange but he’s been her best friend for years and he’s always been there for her, whenever her dad is shitty to her or when she needed help with school. They have to try a lot more at their friendship then other people because they don’t have much in common, but it’s worth the effort and Lily is a strong believer in loyalty.

She stands up to wash the dishes and her head starts spinning. She puts a hand against the counter and notices her skin feels like it’s tingling. “Are you okay?” Jason asks worriedly.

“I’m fine, just need to sit down for a second,” Lily says, her tongue feeling unwieldly in her mouth. She shakes her head to try and get rid of the spinning feeling but it doesn’t really work. She sits back down and lets Jason clean up for her. When he’s down, he takes her to the couch and they sit down next to each other, putting on a television series. “Let’s just take it easy today, you’re looking a bit sick,” Jason says, putting his hand against her forehead to test her temperature.

“Okay,” she agrees readily, feeling more light headed by the second. She slumps against Jason, who puts his arms round her and strokes her hair comfortingly, and watches the television, trying to focus. For some reason she keeps getting distracted. Jason smells amazing, like deep musk, and he’s deliciously warm. Her head is spinning. She can’t focus. She sinks into him. He feels amazing, too. She feels amazing. Her skin is tingling all over. “I’m really warm,” she complains, her voice sounding strange and far away.

“Why don’t you take your jumper off?” Jason asks. He sounds like he’s coming from underwater.

“Yes,” she agrees. Anything Jason suggests is probably right. She sits up and tugs off her jumper. She’s only wearing a bra underneath. The cool air hits her skin and makes her feel so much better. “Can I take my skirt off?” she asks Jason.

He nods at her and reaches round to help her unzip. He pulls it down and then she’s tipping back onto his lap on the couch. She wriggles around, lying with her head against his chest again. His hand is on her bare shoulder, lightly stroking her arm. The television is a pleasant blare in the background. Jason’s hand moves onto her back, trailing up and down it. Sparks of lightening are spilling out from his fingertips. Jason sits up and lifts her so she’s sitting up as well, next to him. She clambers onto his lap, knees either side of him, facing him with her arms around his neck. “Lily, are you okay?” he smiles at her. He looks so handsome. She can hear him more clearly now. She sinks down on top of him and nods, clutching around his neck. She’s desperate for something. She needs him. She starts grinding down on him, and god, it feels amazing. She’s moaning loudly, grinding on Jason frantically so the delicious sensations keep on coming. Her head sinks into his shoulder and she bites his neck. “Please,” she whimpers.

“Do you want me to touch you?” Jason asks.

“Yes please,” she says.

“Say, ‘please, master’.”

“Please, master,” she begs. He slides his hand from her waist to between her legs, pushing her panties aside to touch her. She’s dripping wet. The feel of his fingers touching her is amazing. She moans loudly and tries grinding against his hand. His other hand grips her by the neck and he tells her not to move, so she stays still. Then he starts rubbing her, slow at first, then faster and faster. His finger circles around her clit and suddenly dives down and enters her, pumping in and out of her. He adds another finger, stretching her open, still moving in and out. He has a light clench around her throat, so her head is tipped back, and she is moaning wantonly with waves of pleasure rolling up her. He slams his two fingers inside her and she orgasms loudly, clenching around his fingers. He withdraws his fingers and wipes them against the side of the couch. She slumps against his chest and falls into a pleasurable sleep.