Pairing: Jess/OFCs, Jess/Sarah Blake, Jess/girl!Sam
Summary: Based on the prompt "photoshoot". Five times Jess has her picture taken.
Notes: Thanks so much to audaciously for the kick ass beta<3 feathertofly, I really hope you like this!
1. Age: 6
Jess starts first grade tomorrow and she’s so scared. She doesn’t know anyone here at all and her mom promised her she’d like her new school, but she doesn’t want to go tomorrow.
It’s not fair. She liked her old school and her old teacher and her old friends. Why did they have to move?
Dad’s got a new job or something, but it doesn’t mean they have to move all the way out to California. It’s too sunny and warm, and she doesn’t like it.
Her mom drops her off at school early. Jess plays with the edges of the straps on her backpack and watches as everyone else runs into the school. They all already have friends and stuff. It’s not fair.
Jess turns around.
A girl not much taller than her smiles shyly, her red hair in pig tails. It’s pretty cool.
“Hi.” Jess tugs on the straps on her bag.
“I’m Jackie. My mom said you’re new.”
Jess nods and looks down at the ground.
“Yeah, my dad has a new job.” Jess looks up at Jackie.
“You can sit with me.” Jackie bites her bottom lip.
Jackie moves away three years later, but Jess’s mom takes a picture of the two of them before she leaves, arms around each other’s necks and grinning widely. She sees Jackie her first year at Stanford, still the same shy redhead who recognizes Jess as soon as she steps into the classroom.
She’s not the same Jackie she remembers, because Jackie invites her to grab dinner and kisses her behind her dorm, nipping at Jess’s bottom lip.
Jess holds a disposable camera up, her hands buried in Jackie’s hair as they kiss and hits the button. The picture comes out skewed and off center, but she can see Jackie’s curls and her fingers, their mouths pressed together.
2. Age: 16
Allison is tiny. Jess is still growing, close to six feet tall, but Allison barely comes up to her shoulders. She’s thin and adorable, always smiling and she’s the first girl that Jess has let herself admit she likes. More than she should.
Allison giggles, burying her face in Jess’s shoulder. It may be California but it’s a small town, and this, two girls going to a dance together is still frowned upon. They’re both going solo anyway and Jess can barely breathe when she sees Allison jump out of Bobby’s jeep, her short black dress stopping high on her thighs, showing off her legs. Jess feels her mouth go dry when Allison walks up to her, blonde hair pulled up in a loose bun, stray strands brushing her face.
“Hey, baby.” Allison brushes her hand against Jess’s and walks backwards towards the auditorium.
Jess grins and follows, their heels clicking against the pavement and Bobby yelling at them to slow down. They hold down the fort at a table in the back, Bobby getting dragged out to dance by Cassie for every other song. Jess has a good time, despite the fact that she can’t go out and dance with her girlfriend. Allison lets her legs press against Jess’s, their feet tangled together under the table.
Cassie comes running by, her camera in hand and pushes her hands together.
“C’mon, I don’t have any pictures of you guys!”
Jess grins and leans close to Allison, her arm around Allison’s shoulder. Allison giggles and tilts her head towards Jess, her hand resting high on Jess’s thighs. The camera flashes and when Jess pulls away, Allison tugs on her hand and slides their fingers together.
Her roommate is kind of crazy but Jess loves her anyway. Any attraction she felt towards Becka melts away after their first week living together. Her bad habit of leaving half eaten bowls of cereal on her desk kills any desire Jess might have had towards her. It’s a good thing, because Becka’s her best friend and the only thing that gets her through the worst of their first semester at Stanford.
Jess glances over at Becka. It’s a rainy and cold Saturday afternoon and neither one of them felt like doing homework.
“Okay.” Becka changes the channel on the TV. “What did you wanna watch? ‘Cause there’s an O.C. marathon on...”
Jess rolls her eyes and snags the remote away from Becka. She giggles and pushes her feet against Jess’s legs. Jess moves away, scowling at Becka and changing the channel to some movie before tossing the remote out of Becka’s reach.
“Hey, Jess, seriously? It’s okay.”
Jess glances at Becka and smiles, before turning her attention back to the movie. Later, she gets up to get a couple of sodas out of the fridge while Becka runs to the bathroom. She spots a picture of the two of them in Zach’s room, giggling over something and Jess thumbs the bottom of the picture.
4. Age: 19
Jess can’t see anything.
Jess nods and takes a deep breath, clenches her fingers against the bed spread. She hears a soft laugh and it calms her nerves sufficiently. She feels fingers brush against her breasts, teasing her nipples before the hand presses down on her stomach. Jess lets out a giggle.
“Must not be doing something right if you’re laughin’ over there.”
“It tickles.” Jess swallows as the hand drags along her thighs, teasing up to where she’s hot and wet before resting on her knees.
Jess takes a deep breath when she feels pressure against her cunt, hard plastic teasing around her slit before pushing inside. She lifts her hips as it slides inside, filling her up. It’s not quite enough though, smaller than what she usually likes. She makes a noise in the back of her throat and stills when she hears the click of the camera.
This isn’t about sex. This is about Jess trusting Sarah enough to show herself off without fear that the pictures will end up where they’re not supposed to.
“So gorgeous.” Jess feels Sarah’s long hair brush against her skin, tease against her nipples before Sarah pulls away all together. She hears the camera clicking again and wants to pull her legs together, hide herself completely from the lens. Except she agreed to this ages ago, told Sarah she trusted her to do whatever she wanted.
Jess has no idea how she ended up here, blindfolded on her own bed, dildo between her legs and naked, Sarah taking pictures of her.
She feels hot and flushed, knows her skin is redder than normal. She doesn’t get embarrassed ever, not even when she shows up to class late or runs to pick up take out while covered in paint.
“C’mon, show me what’cha got.”
Jess takes a deep breath and widens her legs, lets Sarah pull the dildo out and press it back inside of her. It’s not enough pressure, not enough and Jess wants to bat Sarah’s hands away and go to town. She needs more.
“Just go with it, baby.”
Jess says fuck it, lets her left hand drag down her body and lifting her right leg, widening her legs as she grabs the dildo between her legs. She pulls it out slowly, teases herself for a few minutes. She fucks herself, lets the width of the dildo stretch her and it’s good, but it’s not what she wants. She pulls it out, drops it on the bedspread and runs her fingers along her clit. She teases her tits with her right hand, tugging at her nipples, a little rougher than Sarah would.
“Do it.” She hears Sarah taking more pictures and takes a deep breath as she slides a finger inside of her cunt.
She groans at the slickness of her pussy, how wet she’s getting just from what she’s doing, Sarah walking around the bed and taking pictures of her. She wonders what Sarah sees, if she’s just taking in shadows and the light from the bedside table, the sun going down outside their bedroom window. Sarah’s an artist first and this...thing they have going on is just another excuse for Sarah to explore that.
Right, that’s what she keeps telling herself.
She sighs and slides a second finger along the first, stretching herself more. Her fingers move easily inside of herself, stretching her wide. She’s hot and wet inside, her cunt tight even though she was fucking herself with the dildo. She takes a deep breath and slides a third finger inside. It’s too much, too tight and too much for her to handle. But she can hear Sarah breathing heavy and her camera is still clicking away.
Jess moves her hips, gives herself a better angle to fuck herself, her fingers rubbing inside of her. She wants to touch her clit, her fingers hitting the right spots and she’s so close.
“Finish yourself off.”
Jess slides her right hand down and rubs her clit, her fingers fucking in and out of her cunt as fast as her hand will move. She’s so close, moving her hips until she can slide a fourth finger inside of herself, so wide and tight and she’s coming, biting her bottom lip as she feels her pussy constrict around her fingers. When she pulls her fingers out, they’re soaked, her wetness dripping out of her cunt and onto the bedspread.
She feels the bed shift and can hear Sarah take a few more photos before the blindfold comes away from her face. She blinks as the room comes into focus, the light from the sunset breaking through the window. Sarah’s kneeling on the edge of the bed, panting as she leans down and kisses Jess, her tongue sliding into Jess’s mouth.
“You’re so gorgeous,” Sarah murmurs, wrapping her fingers in Jess’s hair.
Jess blushes, thinking of what she just did and wonders how the pictures came out.
5. Age: 21
Jess hates football games. But Becka says, “I’m sick of your fucking moping”, and drags her out.
Trust Becka to tell her how it is.
She dresses in Stanford colors like a good student but she can think of a million other places she’d rather be right now.
She’s drinking her soda and devising a plan to sneak out without Beck noticing when someone next to her says, “This isn’t really my idea of fun either.”
Jess jumps and almost drops her soda on the ground. She looks over and does a double take at the girl sitting next to her. Grinning wide with dimples out in full force, hair cut in a bob halfway up her face, there’s pinch in her gut that she hasn’t felt since Sarah left two months ago.
The girl waves her hand, cheeks pinkening a little bit. She’s tall and lanky, a few inches taller than Jess, which is saying something. She’s absolutely nothing like Sarah, except for her dark hair and the grin on her face. She’s skinnier, less curvy, and instead of looking like she’s undressing Jess with her eyes, this girl’s shyly checking her out.
“Football.” She shrugs and her hair blows in her face with a gust of wind. “It’s kinda boring.”
Jess laughs, throwing her head back. “Right? I only came along because Becka threatened to make me sit through another Sorority Life marathon.”
She shudders. “Oh no, that’s just wrong.”
“Yeah, no kidding.” Jess glances around. Becka’s too busy yelling at the field, Zach standing next to her, waving his hands and splashing beer everywhere. “You wanna get outta here?”
She widens her eyes and nods.
They sneak out behind the bleachers. Jess drags her off to a corner, partially hidden away.
“My name’s Jess.”
She squeaks when Jess leans up on her tiptoes and kisses her, but she gets with the program fast, sliding her arms around Jess’s waist and pulling her closer.
She pulls away, panting a little. “Samantha Winchester.”
Jess grins and pulls her head back down for another. They make out underneath the bleachers until she feels her cell buzzing against her thigh.
Later on, they stand close together while Becka takes a picture of the group, Sam’s hand resting low on her back. Jess looks up at Sam, grin on her face, feeling twelve years old all over again.
Becka slides a copy of the picture into Jess’s bag at lunch the next day. When Jess gets home, she sticks it on her fridge, over her shopping list.
It’s a good picture.