#jess x reader

A - aftercare:

although jess is a very 'don't care' kinda guy, he really goes the extra mile to make sure you're okay after sex. He'll walk you home, run you a shower and be on lookout to see if luke or Lorelei is coming

B - body part:

BIG butt guy. he's constantly squeezing your ass no matter what position you're in.

C - cum:

jess loves to cum in your mouth, most times he'll pull out and have you swallow his cum.

D - dirty secret:

although this isn't necessarily 'dirty', jess loves to rub your head and play with your hair. if you guys are watching a movie normally you'll lay on his lap and he will rub your head loving the silky feel of your hair

E - experience:

jess is very experienced but he makes sure that your up to pace with him, always making sure everything's okay. he's not one to judge if you're not.

F - favorite position:

jess is always torn on what position to have you in. on one hand he likes doggie style because he can squeeze your ass and be a little more rough with you, but on the other hand he also like missionary because he can watch your face as he sinks in and out of you.

G - goofy:

most of the time jess will just make sarcastic remarks while you guys are having sex

H - hair (on fem)

jess is definitely the type of guy to not care, I can see this conversation going down;

"we can't, I haven't shaved."

"so?" 🙇‍♀️

I - intimacy:

jess very secretly loves to be intimate. he claims that he just does all that stuff because you want him to but actually he loves making sure his girls taken care of.

skipping j

K - kinks:

where do I even begin, jess is a very kinky man. he loves fucking you in front of a mirror to have you watch what he does to you, he is always pinning you hands because he knows you like to touch him, and then right when you're on the edge he'll let go. he likes eye contact and when you close your eyes he'll give you a warning before pulling out

L - location:

anywhere. shower, library, car, apartment, bedroom, bathroom, floor, dresser. the only time he won't do anything is in public.

M - motivation:

jess is always motivated, but he likes to make sure you are to. and if you're not he doesn't mind it just takes him a second to turn that switch off

N - no's

literally any guy coming near you, he's also very bug on making you comfortable, if you guys are maybe doing something a little risky and he can tell that your to scared or uncomfortable then he'll stop

O - oral:

he will never admit it, just he loves going down on you, pulling his hair or watching you pull against the belt he uses to tie back your hands.

P - pace:

he loves rough quick aggressive sex, but, he can do that for hours

Q - quickies:

most of his quickies are just maybe getting his baby off, fingering her, maybe eating her out, but he also will do what he has to do. if he hasn't seen you in like a week and you don't have that much time, the back seat of his car is normally where you guys end up.

R - risk:

jess loves the risk because it mean he gets to fuck his babygirl, he doesn't care what the outcome is.

S - stamina:

ALL NIGHT LONG! he will go until you can't take it anymore, that's his deciding factor.

T - toys:

not a toy guy. he likes getting you off himself.

U - unfair:

public teasing. he likes to whisper dirty things in your ear and watch you squirm.

V - vocal:

you really have to work to get this guy to be vocal. he will not give easily.

W - wild card:

he loves to always be touching you, having his arm around you, playing with your hair, if you passing each other he'll lightly squeeze your arm

X - x-ray:

6.5 - 7 inches, enough to definitely do you justice but not so much that your like splitting in half.

Y - yearning:

ALWAYS. always thinking about you and thinking about sex with you.

Z - zzz:

whenever you guys manage to spend the night together its always you falling asleep first, but jess is soon after. jess likes to rub you head and he loves when you two are all tangled up together.

"I need to get some batteries, I'll be back," Jess said as he walked down the stairs. He noticed you were at the diner and stopped in his tracks. "Didn't know that you liked spending your afternoons with middle aged women." That comment made Carrie and the other women gasp. "The old ladies I wanted to knit with were busy, so I had to find company."

"Good book though," He said while you hummed in response. "Jess, Jess! Come over here and meet my oldest friends!" Liz said as she beckoned him over. Jess looked like he wanted to be anywhere but there. "Girls, this is Jess," Liz said proudly. A chorus of 'hellos' sounded. "Hello, handsome," Carrie said as she winked. You had to stifle a laugh for the sake of Jess. "He's going to walk me down the aisle! Is that cool or what?" Liz said to her group.

"It's no big deal," Jess said, trying to draw away attention from him. You found this funny. "It's a very big deal," you said with a dramatic look on your face. Jess gave an unimpressed look. At that time, a deliveryman walked through the door.

"Can I help you?" Luke asked with the confusion written across his face. "Got a package here." "From who? I'm not expecting anything?"

"It's a very important package," the deliveryman said with a serious look on his face. Luke stepped closer. "But there's no address on it?"

Jess smirked as he looked over to you. "I was going to go to the bookstore after getting batteries. Care to join?" he said, extending his hand to you. Looking for any way to escape this situation, you obliged. "Bye Luke, see you later."

"Have fun," Jess said with a laugh as you left the diner and heard a muffled "Have fun with what?!" as music started blaring from the inside.

-

"I was already having a bad day and then some guy had to spill his coffee all over my new blouse and my copy of crime and punishment," you lamented to Jess while you walked towards the bookstore which you frequented. "I didn't have enough money to get myself a new copy and a new blouse, so I decided to get the blouse because of my internship." Jess smiled at that. You were hardworking and diligent, while he was... less of that. You just got the coveted internship at one of the most competitive law firms in Connecticut, and you needed to make a good impression; a shiny copy of crime and punishment accompanied by a coffee stained lavender blouse wouldn't exactly do that.

The jingle of the door chime woke you from your thoughts about your precious copy of crime and punishment. Jess bent his head and didn't say anything to Kirk, the acting cashier, while you smiled and greeted him. You knew he wasn't one for politeness, so you tried to compensate.

"There's something I think you'll like." Jess meandered towards a shelf hidden at the back. You cluelessly trailed, wondering what book it could be. Knowing Jess, it could be a 2000 page book about a whale or a 20 page romance novel; the man read anything and everything with words on it. When he pulled a book off a shelf, your jaw dropped.

The blood-red lettering reading "crime and punishment" contrasted starkly to the obsidian binding that you ran your fingertips across.

"wow, this must cost a fortune, maybe i'll get it once my paycheck can get me more than one cup of instant ramen."

"let's go, i need to see what the guy at the diner did to luke,"

-

"does this dress look like too much?" you ask while twirling around in front of Lorelai. "no, this one is perfect. It makes you look like you'd be sitting in a tower waiting for your prince to save you from a dragon." You looked at her while she lounged on the couch in the house you had graciously invited yourself into. Well, she wasn't wrong. The dress was a light blue, silky fabric billowing around your ankles. The sleeves added to the whimsicalness of the dress. "only if the prince was Jesse Bradford,"

"you know what would make Prince Bradford fall in love with you even more? this flower crown," Lorelai said as she got up and pulled out a pretty-looking headband from a shelf. She put it on you and turned you towards a mirror.

"rory never let me dress her up like a princess; i should adopt you."

-

"hear ye, hear ye! announcing the arrival of her Royal Highness, the Princess, finally gracing us with her presence!"

"shut up, i was five minutes late; being a princess is hard work, you should know," you joked to Jess. You two met up near the gazebo, his reasoning being that he needed to make fun of you all dressed up as long as he could before he had to walk his mom down the aisle. "do you want to go get a seat? you're gonna be here for a long time. or maybe not, i've only been to three of my mom's weddings. "aren't you gonna sit down too?" you asked. "my mom wants me there to give her "emotional support" whatever that means," he joked as he led you to a seat next to lorelai and luke. Carrie from the diner yesterday was talking to them. lorelai looked concerned and luke just looked uncomfortable.

"hey, is everything alright?"

"no, there's gonna be a delay since liz ripped her dress and it's gonna take some time to fix it," carrie explained. "she told me to spread the message,"

"well, spread it car." luke got a suggestive look from carrie. "the message, the message." When carrie walked away, luke looked like he hadn't gotten oxygen in a good five minutes. "that woman makes me uncomfortable."

"poor liz, does she know how to fix something like that?" you asked jess and luke. "she was never one for household skills-" "i used to stitch up her renaissance fair costumes. trust me, she can't" jess interrupted luke. "i'll go see if she needs some help. where did you say she was?"

"she's at miss patty's,

-

You could hear Liz's laments from outside miss patty's. "my dress is ruined! how am i going to get married in a torn dress?" you pushed open the doors to Miss Patty's and gave Liz a concerned look. "I heard you needed some help? can i do anything for you Liz?" you asked, moving over to take a look at her dress. "I'm such a klutz, i tripped standing up and now its torn," she held up the side of her dress where there was an obvious tear. You grimaced and picked up the Doose's brand sewing kit from the table next to her, attempting to fix her dress.

"There you go! as good as new," you finished up the last stitch on her dress. "Oh, you're such a darling," Liz fixed up her hair. "you'd make a great daughter in law to a lucky lady someday. Could you tell jess to get ready for my grand entrance?"

The implied message didn't go past you. With cheeks redder than what your dollar store blush could get you, you thanked her and went down to the gazebo.

-

The ceremony passed by quickly, with you and Jess trying to think of sad and miserable things to make you stop laughing at the proceedings. "Oh man, i swear to you my wedding's gonna be better than whatever that was," you said, wiping the tears of laughter from your eyes as everyone went to the buffet line to get some food. "We'll see that," jess said as he inspected a turkey leg before putting it on his plate. You gave him an offended look. "Do you not think my wedding would be so much better than this 1500s medieval thing going on out here? I'd totally pick out a better theme," you said as you piled some mysterious looking food onto your plate. "I highly doubt that, and I hope you know that what you're putting on your plate is minced liver."

Your hand froze right right before you almost dumped another spoonful food onto your plate. You promptly pushed off the whole serving of minced liver back into the serving bowl. "That was so uncouth of you, private school girl. Did they not teach you manners at your finishing school?" You elbowed jess in the side as you chose a much more appetising looking burger prepared specially, from luke's. "one, i'm in college now; two let's sit down. I don't think they taught you table manners either city boy,"

-

After finishing up your dinner, you two decided to walk around to socialise. If socialise meant to make fun of every person in renaissance attire.

"the guy in the pantaloons probably thinks energy drinks count as water," jess pressed his lips to your ear, narrowly missing your cheek because of how much you were laughing. Everyone must have thought you two were drunk or high, from how hard you two were laughing. That was when you heard medieval sounding music playing where everyone had gathered.

"jess. you have to dance to this. i physically need to see it," you clung onto his arm, bringing him to the area near the gazebo, where Liz and TJ were dancing. They were doing some complicated looking dance straight out of the middle ages. "no way am i doing that. i'd rather slam my tongue in a car door." "please...?" "no." "...pretty please?" "fine, but you're coming out there with me." and before you could say no, he'd already dragged you to the dancefloor.

you'd be lying if you said you didn't have fun embarrassing yourselves. you'd only been dragged out of the dancefloor because TJ wanted to seranade Liz with a special dance just for her, and boy, were you glad you didn't have to see that.

-

Jess was walking you over to the gilmore house, where you'd been crashing with lorelai since your exams had been over. You, being a rich international student who's parents knew Richard and Emily Gilmore, had been asked to stay with them when you went to Chilton, and to Yale subsequently. Of course you could always tell them that your exams hadn't ended yet, and you were still staying at Yale, but where's the fun in that? You, lorelai, and rory, were planning on having a weekend of binging old movies and junking on the most unhealthy food you could find, so being a few days early wasn't a problem.

"after this is back to new york?" you asked him while approaching the door of lorelai's house. "maybe not, this time. might stay here for a bit; it's not that bad," he responded, leaning on the door. "any plans for summer?" you looked up at him. "you know, i've always wanted a summer romance. you know the type you read in the books, the notebook and stuff like that," you played with the straps of your purse. "maybe that'll be one of my plans," he said as he grabbed your waist and held you right up to him. "want it to be longer than just summer though." he pressed his lips to yours as he ran his fingers through your hair. you took a second to react, but you were kissing him back too. when you pulled apart for air, breathing heavy, you smiled.

"can't wait"

“how was work?” he asks, caressing your arms “the same, tiring. yours? how’s the book going?” “it’s going well, managed to get a few more chapters done.” “that’s nice.”

Jess simply hums, trying to get around the kitchen with you holding him, “you arrived home in a perfect timing.” “how’s that?” “just finished some hot chocolate for the both of us.” smiling up at him, you move to his front to finally plant a kiss on your boyfriends lips.

he reciprocates with more fervor, one of his hands moves from your arms to hold your face and yours slip under his sweater, causing Jess to push you away from him with a shriek and you to complain. “wtf?! your hands are fucking freezing!” you try to hold him back against you and insert your hands under his sweater, again, “𝑓𝑢𝑐𝑘, 𝑦𝑜𝑢 𝑎𝑟𝑒 𝑠𝑜 𝑤𝑎𝑟𝑚𝑚𝑚𝑚 ”, Jess who does little to move you, only stays tense due to the contrast of the temperature

“take them out” “no” “it’s like freaking north pole”, the only response Jess gets it’s you sliding your hands further up his back looking for more warmth while tightening the hug. “I hate you” you look up at him grinning and he smiles back at you “you loveee me” “you wish” “just hug me back you fucking idiot.”

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"Jess? Are you dressed?" You poked your head into the bathroom, finding Jess hunched over the sink.

His face was pale, and blood pooled in his fingertips as he clutched the edges of the sink.

Slowly, you walked over and put a hand on his back. "Hey, what's wrong?"

"Don't touch me," he slapped your hand away, glaring out of the corner of his eye.

"Jess…" Crossing your arms, you gave him a stern look. "Come on, what is it?"

"Nothing! Nothing!" He jerked to look at you, gritting his teeth. Pushing past you, he grabbed his bag, shoving a book inside. "Let's just get this over with."

"We don't have to—" the door slamming cut you off.

Sighing, you changed into your costume and followed him to the gazebo, sitting down in a foldable chair.

People walked past you, doing party prep. As time went on, it got more crowded, louder with last-minute additions.

You looked up from your book, finding Jess nowhere to be seen.

"Jess?" You called, searching the square before moving on to Miss Patty's "Hey, have you seen Jess?"

"He's not out there?" Liz looked up from her torn dress, frowning. Patty looked over from her rack of clothes. "I think I saw him by Luke's a few minutes ago."

"Thanks."

The lights were off inside the diner, your view obscured by the setting sun.

Against the glare, you could make out Jess's bag sitting on the counter. The bell rang as you pushed the door open. "Jess? Are you in here?"

A quiet squeak came from behind the counter. You looked over it to find Jess hiding with his knees pulled up to his chest.

Wide, watery eyes looked up at you, and he curled into himself. As you walked around it, the smell of ammonia hit you. "Oh, baby."

He flinched away from you, hiding his head in his knees. "Sorry"

"It's okay; you're not in trouble." Gently, you ran your fingers through his hair. "Let me go tell people we're gonna take off early, okay? I'll be back in a minute."

Sniffling, he nodded and watched you leave. Lorelai was helping Liz fix her dress when you walked back inside Miss Patty's. They looked over to you, Liz speaking up first. "Did you find him?"

"Find who?" Lorelai asked, going back to pinning the dress.

"Jess, I found Jess." You nodded, smiling apologetically. "We're gonna have to leave early, I think he got a stomach bug."

"Oh no," face falling, Liz shook her head. "I guess he really didn't want to walk me down the aisle."

Sighing, you shook your head and left, speed-walking back to Luke's. Jess was still hiding behind the counter, holding several wet paper towels.

You pulled the trashcan over, taking the paper towels and tossing them into it. "Ready to go?"

"What about—?"

"Don't worry about it." Cutting him off, you pulled him up and sprayed the floor with cleaner, tossing a rag down on top of it. "There."

Silently, Jess followed you back to your hotel room, clutching your hand.

The closet door creaked open, and you grabbed a pair of his pajamas. "You want a bath or a shower?"

"…" He just stared down at the floor, letting go of your hand.

"Bath it is." You pulled him into the bathroom, watching the tub fill. "Do you need help with your clothes?"

"No!" Avoiding your gaze, Jess pulled at his shirt, then at his pants when that didn't work. "…go away."

"Hey," with a slightly sterner tone, you padded over and unlaced the front of the shirt. "Lift up your arms."

Begrudgingly, he lifted his arms and let you pull the shirt over his head, setting it in the sink.

He leaned against you as you undid his belt, mumbling something apology-adjacent.

Giving him a soft smile, you stood up and kissed his cheek, tossing the rest of his clothes in the sink. "It's okay, ready to get in the tub?"

He nodded and sat down in the bath, pulling his knees up to his chest and staring into the water.

You kneeled down next to the tub, grabbing the body wash and a rag. "I'm not mad."

"I'm sorry." Fat tears rolled down his cheeks and dripped into the water. " 'm sorry."

"Shh, you don't need to be." Gently, you cupped his cheek and turned his head to kiss him. "No one's mad at you. You're not in trouble."

"Promise?"

"I promise," you nodded. "Do you want to tell me what happened?"

"Talking" Sniffling, he hid his face in your hand, pressing it against his face. "Too much talking…they hit me."

"Who hit you, darling?"

"Luke, and…the guy"

"The guy? You mean TJ?"

"Mhm."

"At the bachelor party?"

He nodded, going back to crying into your hand. Careful not to spook him, you set your hand on his back, ignoring the water wetting your wrist.

A soft sob broke the silence, and it was only a second before Jess's chest was heaving as he sobbed.

Briefly, you wondered how well he could breathe, pulling your hand away from his face. Your hand had wrinkled, and his face was red and puffy. 

"'M sorry" he managed to say between sobs and gasps.

Shaking your head, you leaned over and pulled him into a hug, ignoring your now wet clothes. "There's nothing to be sorry for. You got scared, that's all."

"Are you sure?"

"I'm sure" carefully, you helped him out of the tub and wrapped a towel around him.

He squirmed as you tried to dry him, complaining about being cold.

Once he was only damp, you helped him into his pajamas. "I'm going to change, alright?"

When you left the bathroom, Jess had curled up on the bed, arms around himself. You sat down next to him and pulled the blanket up. "Hey."

"Hey."

The faint sound of music came in through the window, making you turn on the TV. "You want to watch a movie?"

"Mmkay," he propped his head up on a pillow, shaking his head as you flipped through the channels.

Finally, you settled on an old Disney movie and lay down next to him.

He wrapped his arms around you, shutting his eyes and listening to the movie.

"Goodnight," you leaned down and kissed his forehead. "I love you."