#there is not enough content about my king bill hader wtf

[patchouliauthor]

Why Not? | Bill Hader x F!Reader

Warnings: 18+ Minors DNI. Oral Sex (f. receiving) Switch!Bill if you squint, Unprotected P in V (wrap it up), professor!Bill, alcohol, mentions of daddy issues. Age gap but obvi still legal.

Word Count: 4270 something

A/N: this is the first one-shot I’ve posted and it’s because there is a LACK of Bill Hader smut and I’m here to solve that problem. Please send me more requests I love getting compliments and that’s what I am doing this for. There will be a part 2 and maybe even a part 3 to this idk.

Summary: You are a waitress and a college student. You meet the handsome Dr. Hader at your work and hit it off quickly. 

You had been working at this waitress gig for two years. It had grown into a second home for you while you were away at college. Serving plates of greasy food to quite an interesting crowd of people filled with interesting stories became commonplace to you, and it always kept you entertained. 

The summer was hot; this was the first time you spent summer in your college town as you were gearing up for your final semester. Finally graduating with a degree in Communication Studies, just 15 credits to go. Just had to get through the summer and then the five long months you had left. Did you know what you would do after college? Not yet, but you were surely going to figure it out. You always did.

You looked at the clock. Only an hour till you clocked out. Despite loving your job, you also loved going home and getting off of your aching feet. You were going to finish your last tasks for the night when your favorite host comes up to you. 

“I sat a guy in your section. He said it’s for two.” She said. She scurried along back to her station and you sighed. One more table won’t kill you, you suppose.

You looked over to the man and he had a bouquet of flowers. He looked rather nervous also, which confirmed your suspicions that this was a first date. He was quite handsome too, with dark hair and blue eyes. He was quite a bit older than you, you thought, maybe 45. A first date at 45? What an interesting fellow.

You walked to the table. “Hey there! Welcome in. What can I get for you?” 

He seemed startled. “Oh, I’ll just take a water with lemon for now.”

You smiled at him and went to get him his drink. You returned to the table with the glass and set it down. He doesn’t seem to notice as he is just looking out the window towards the parking lot.

“Can I get you anything else or would you like to wait for the rest of your party?” You asked quietly, trying not to startle him.

“I’ll wait. Thank you.” He said, smiling. He had a nice smile, and you really hoped he wasn’t going to get stood up. Then again, if he did, maybe you could offer this poor, handsome man some comfort.

“No problem. You’re my last table of the night so if you need anything just let me know.” You said. You smiled and walked away. 

An hour went by and no one joined the man at the table. You sat at the bar looking over at him. Your best friend Vic is the bartender, and the coolest person you know; they have dark green hair, both nostrils pierced, and patchwork sleeve tattoos featuring work from so many artists. Not to mention that they could read your mind.

“That guy’s been there forever. You should go see if he needs some company.” They said, smirking.

“Don’t tempt me. Why am I always attracted to older men?” You said back.

You turned to look at them and you both said at the same time. “Daddy issues.”

You both laughed and turned back to the man as he checked his watch and then looked at the door.

“Seriously, how long has it been since you were over there?” Vic asked.

“About 20 minutes. Should I go over again?”

“Only if you give him your number.” 

You rolled your eyes at them, but you did decide to go over again. He sighed and smiled at you as you walked up. 

“You want to order something? The kitchen is closing soon.” You said gently.

He sighed, his eyes sadder than his smile. “I’m alright. I’ll just take the check.”

You chuckled. “You just got a glass of water with lemon, I’m not going to charge you.”

“But I wasted so much of your time, I want to at least give you a tip.” He said.

You hold back the inappropriate joke threatening to spill out of your mouth. “How about I get you a real drink so your evening isn’t wasted.”

He looked at you and then down at the table before chuckling. “Hell, why not?”

You smiled. “How do you like your whiskey?”

“How do you know that I like whiskey?” he asked.

“If you don’t answer I’m getting it neat.”

He chuckles again. “I prefer neat.”

You smiled for what seemed like the 100th time at the man and went back to Vic to get his drink. They already had it poured and had a glass of your favorite cocktail right next to it. They pretended not to notice you approaching the bar. You rolled your eyes and smirked as you took both drinks. You and Vic had gotten quite used to the regulars here, and it wasn’t hard to guess the type of drink the man would want when he walked in. You considered yourselves pros at guessing, sometimes even making competitions out of it. As you headed back to the table you heard Vic whisper “Go get em tiger.”

You set the whiskey down in front of him and sat down across from him. He looked up with amused confusion.

“Sorry, I thought you could use the company.” You said, taking a long sip from your drink.

He smiled that gorgeous smile again. “You’d be right.”

“First date?” You asked, even though you knew the answer.

He looked down. “Yeah, the first in a really long time.”

“Oh?” You asked. You really hoped he wasn’t a widow or divorced, you’d hate to see those pretty blue eyes well up with tears, ever.

“Yeah, I…” He trailed off for a few seconds. “My last relationship didn’t end the best way.” 

You continued to look at him, waiting for him to finish that thought.

“I woke up one morning and she was gone.” He said, looking up at you, gauging your reaction.

“Oh. Were you married?” You asked.

“Oh no. We had a pretty long relationship but we never made that step.” He said quickly.

You were relieved despite yourself. You didn’t think you actually had a chance did you? Did you think that he would be interested in someone possibly 20 years younger than him? You shook that from your head and continued.

“So what do you do for a living?” You asked.

“Actually, I’m a college professor.” He said.

“Really? That’s impressive.”

“Not really. When you socialize with professors all day you realize they are just stuffy, but not much more special than other people.” He said.

“So do you have a PhD.?” You asked.

“I actually have two.” He said bashfully.

“Two? You are quite an interesting man.” You said, smiling over your drink.

He returned the grin while looking into your eyes.

You talked for a long time, nursing your drinks, until you saw Vic mopping the floor. He noticed at the same time.

“Let me pay for your drink.” He said

“Absolutely not.” You answered.

“Please? It’s the least I could do.” He said as he gave you slight puppy dog eyes.

You caved and went to get his check. As you input the information, you gave him your employee discount. You returned the check to the table. “I’ll take it whenever you’re ready.” 

He pulled out his card and handed it to you, and you took it to ring him up. You also decided to write your phone number on the check. What’s the harm? At least maybe you could make friends with someone who would be a great reference on job applications.

When you returned with the card and the check, you handed it to him. “You have a great night…” You trailed off as you realized you never asked his name.

“Bill. You have a great night too, Y/N.” He replied.

It took you a beat to remember your name tag, but when you did you smiled. You enjoyed hearing him say your name, and you hoped you’d get to hear it again. 

You headed to the back to clock out. You put your apron in your little cubby and went back out to grab his check to take it to the back. When you approached the table, you realized he left the bouquet he had brought. Daisies and baby’s breath. You picked up the bouquet and the check that he had left for you, and realized you weren’t the only one to leave a note.

“For you. Thanks for saving my evening.”

You were shocked, but flattered regardless. The floral aroma from the gorgeous arrangement warmed your heart and you took the check to Vic so they could put it in the banker’s box in the office. Vic smiled at the bouquet, but only wished you a goodnight and nothing else.

As you approached your car, you looked at your phone. You had a text from an unknown number.

“I had a great time. I hope I’m not being too forward, but I’d love to see you again.”

You smiled at your phone and then you got another text.

“Oh sorry, this is Bill by the way.”

~

A few days had passed and you were getting ready for your second “date” with Bill. Did you consider your last encounter a date? Maybe this one was your first real date. 

You were going to The Solstice, a place that Vic recommended. They told you it was super low-key, perfect for a little date with an older man.

You were lining your eyelids with dark brown eyeshadow to create a siren eye effect. You also picked out a perfect black dress that accentuated your curves and black platform Mary Janes. You hoped the outfit wasn’t too dark, but you looked too good in black to pass it up. It was almost time to leave so you called an Uber to take you from your loft apartment. 

You loved your place, it was like a sanctuary to you. Your grandma had signed the lease on it when you were a sophomore in high school and decided where you wanted to go to school. She surprised you with the keys when you graduated. It had just the right amount of space and you felt so grateful. You didn’t know it then, but your grandma had been saving up the money to buy you this since you were born. When you found out, you drove home immediately to thank her in person.

The car pulled up to your apartment complex and you triple checked the license plate before you got in. The ride was uneventful, and you kept looking at your messages, worried that he’d text and cancel. Those fears subsided when your car pulled up to the door and he was standing outside waiting. 

He was wearing a gray casual suit that fit him perfectly. He wore just a plain white t-shirt underneath the jacket and white vans. Such a simple look but so flattering. You tried not to drool as you opened the door and stepped out onto the sidewalk.

When he looked up at you, his eyes brightened and he smiled wide. He had a funny look in his eyes like he was trying not to look you up and down. You wished he would.

You smiled back at him and gave him a hug. It’s at this moment you two hear the music pumping loudly from inside The Solstice. Maybe this wouldn’t be as low-key as you had planned. But hey, at least your outfit will fit in.

As you walked into the venue, it looked like a run-of-the-mill bar. So you were confused why the lights were so dim and the music was so loud. It gave off more of a nightclub vibe, and you weren’t sure how he’d react to that. It was then you saw the sign. “SATURDAY- DJ MIKE.” Of course the one night you came here, the DJ with the loudest speakers ever had to have a set. How were you going to have a conversation with this shy academic?

You turn to talk to him but when you look to where he was, he was not there. You start to worry that the environment had already freaked him out and that he left without another word, when you turn and spot him at the bar. He turned back and looked at you and offered a happy smile. You were still so shocked at his confidence; where did this come from? The bartender slid him two glasses and he set some cash on the counter before he turned back to you and smiled.

“Here you go.” He said as he handed you your drink. It shocked you that he remembered your favorite drink from your last evening together. Maybe you need to evaluate the type of men you typically go out with.

You smiled and took a sip of the drink. You almost immediately felt the confidence seeping into you from the alcohol. He looked over to a corner and found an empty table, then he lightly placed his hand on your lower back and walked with you over to the table.

When you sat down you immediately started apologizing. “I’m sorry. I’ve never been here before so when I suggested it I didn’t know it would be so loud.”

He smiled and shrugged. “Don’t apologize, I don’t mind at all. As long as there is a place where we can hang out, I’m fine with whatever.”

You again bite back the inappropriate urge to tell him that you could hang back at your apartment and instead take another drink of the cocktail he got you.

You talk each others’ ears off for a while, every once in a while stopping so he could get more drinks. The confidence from the liquor was drawing you to the dance floor.

“Do you want to dance?” You asked.

He giggled. “What?”

“Do you want to go dance with me?” You asked again, unwavering.

He contemplated for a few seconds, looking you in the eyes as he pondered the idea. Maybe he’s never really done this before. You didn’t mind, you just really wanted to get on the floor.

“Why not?” He said. It seemed like that could become a theme in your dynamic. You keep pushing him out of his comfort zone, but you hoped you weren’t being too pushy.

You smiled and grabbed his hand and walked to the dance floor. The DJ didn’t play any songs that you particularly wanted to dance to at all for the whole night, but that was when he played the song. “Maneater” by Nelly Furtado. You heard the “take it back” and immediately started dancing. 

The lights were dim enough that you could barely see anyone else, but you still had a hold on Bill’s hand. You then felt his presence right behind you. Without thinking you immediately grinded back into him and you felt his breath hitch against your ear. He slowly placed his hands on your hips and began following your movements. He kept his head behind your left shoulder as you continued to move your hips in a tantalizing circular way. You may not be the best dancer, but the liquor in your system seemed to say otherwise.

He was pressed tightly to your back. You could feel his breath on your neck and it was starting to become a distraction. You felt needier and needier with every second his hands were on you. The liquor was seemingly adding to his confidence as well, and the grip he had on your hips loosened and he started exploring more of your body. 

The song continued, and you did too. It felt like he was touching every inch of you and it was never going to be enough. You could never be too close to him. You turned around and as you did you realized by the tightness in his gray pants that he was feeling the same way as you. His eyes were only half open and he looked slightly disheveled.

“Call an Uber.” You said.

He didn’t say anything but instead whipped out his phone, ordering an Uber to his place at lightning speed.

Three more songs played but you barely noticed. You kept your eyes either on him or on the ETA of the car coming to pick you up. When it said it was a minute out, he grabbed your hand and swiftly walked towards the door. The car pulled up and he opened the door for you after checking the license plate. You slid into the car and he followed quickly behind.

The car ride was excruciating. If there was any more privacy in the vehicle, you know you would have been all over him. It was clear the driver thought so too by the looks he gave you periodically through the rear-view mirror. Bill’s place was only five minutes away from The Solstice, but it felt like five hours. His finger drew circles on your exposed thigh, and you instantly knew you were going to have a great night.

When the car stopped at his condo, he jumped out faster than you have ever seen someone move. He had your door open before you could even process that the car had stopped, and he reached out his hand to help you out of the car. He offered a quick “Thank you” to the driver and hurriedly walked inside, tightly gripping your hand the whole way. His hands shook slightly as he placed his key in the lock and opened the door. 

You took a step in and tried to take a look around. In seconds, he had the door shut and had you pressed up against it. You looked into his beautiful blue eyes as they darkened.

“Tell me if you don’t want to do this. I’ll never forgive myself if I take advantage of you.” He said quietly, his lips just inches from yours.

“I want to do this.” You said. You had barely got the words out when his lips were on yours. Despite the intensity of the kiss, you could feel that you were both smiling. One of his hands that pinned you to the door by your hips slid up and held your face, while your hands found a home within his tousled brown hair. The kiss continued to grow more and more desperate and he pressed further into you, lifting your leg up to his waist. 

He moved his lips from your mouth and down to your neck while you gasped for air. He kissed and sucked on your neck and you instantly knew you’d have to explain yourself to Vic, who no doubt would tease you about this for months. 

You felt the hardness in his pants graze across your core and couldn’t help the breathy moan that escaped your mouth. At the sound, Bill again captured your lips with his. He dropped your leg and began to walk you back to his bedroom, his mouth never leaving yours. When you felt the bed hit the back of your legs, you decided to seize control. You flipped him around and shoved him back onto his bed. He looked up at you with his puppy dog eyes and red swollen lips. His hair was wild and his cheeks tinted pink. He looked so beautiful and you felt an incredibly animalistic urge within you. You turned and shut his door while he continued to look at you. He started to get up.

“Ah ah ah.” You said. You swore you heard him whimper as he laid back against the pillows. 

You kicked off your shoes and slowly started taking off your dress. Underneath, you wore your favorite matching red bra and panties. As good as you looked in black, you looked twice as good in red. As you watched him freely look at your body in amazement, you knew you made the right choice.

“You can touch me now.” You said, and he was up in a flash.

He walked over towards you and put his hands on your waist, but he didn’t kiss you. Instead he continued to trace every inch of you with his eyes, like he was committing you to memory. Like at any moment you’d disappear and he’d awaken from this dream.

“You’re so beautiful.” He said, barely above a whisper. 

He finally kissed you but this one was different. It was slow and full of passion. It slowly started building up, resuming the desperation from before. It was then you realized he was fully clothed and you grabbed his suit jacket and roughly pulled it off of him. Next, you tugged at the bottom of his shirt, and you both broke the kiss just long enough for you to quickly take it off of him.

You sat down on the bed and began to take off his belt when he pushed you so your back was on the bed. As you made eye contact with him he began slowly sliding your panties down your legs.

His eyes never left yours as he placed a kiss upon your naked core.

“Oh honey, you’re just soaked. Is this all for me?” He asked.

“All for you Bill.” You answered.

He began licking the sensitive bud and you threw your head back in pleasure. He started to pick up the pace, sucking harsher and harsher and lapping up all of your juices. You could tell he had done this before, and that he was a fucking god at it.

You could feel yourself starting to come undone when he pushed a long finger inside of you. You moaned loudly at the sensation and you felt him hum with satisfaction. He pumped in and out of you slowly, savoring the feeling of you wrapped around his finger, literally.

“Oh Bill. I’m gonna-” 

“Cum for me baby.” He interrupted you. You didn’t need to be told twice.

You released hard and fast all over his beautiful face. While you were coming down from your high, you saw him stand up, his face glistening with you all over him. You smiled and he smiled right back.

“Want to taste yourself honey?”

You thought you could come undone for a second time at his words alone. You nodded and he dipped down to kiss your lips.

You pull him into another heated kiss and you flip him over so his back on the mattress. You start working at his belt, trying desperately to pull his pants off of him. Once you got them off, you saw the wet spot on his gray boxers. The tent he was forming within them intimidated you slightly, but you were determined to make it work regardless.

You yanked his boxers down his legs and watched his member spring up and hit his stomach. Watching that happen could only be considered a religious experience. You grabbed his large cock and started pumping. His head flew back in pleasure.

You began to wrap your mouth around him when he yanked your head back up.

“No.” He slightly growled. “I need to be inside you. Now.”

He pulled you up so you were above him and he lined up with your entrance. You tried to sink down onto him but he held you up by the waist.

“You’re sure you want to do this?” He asked. Always the gentleman. Asking for consent was the bare minimum but with him it was also incredibly sexy. 

“I’ve never been more sure.” You said and pushed his hands off of your hips. You sank down onto him slowly, adjusting to his size. 

“Bill. You are so big.” You praised him.

He groaned loudly at the feeling of you around him. “You feel so good Y/N.”

After you fully took him in and the pain turned into pleasure, you started bouncing up and down. He helped you by placing his hands firmly on your waist. You bounced for a bit and then sat down on him harshly, rolling your hips in a circle. His eyes rolled back into his head.

You could feel your second climax coming soon and he noticed you start to falter, so he flipped you over so you are on your back and he’s on top. He started pounding into you like you’re the only thing holding him to earth. 

“Bill, you're going to make me cum.” You moaned into his ear and he moaned back at your words. You felt his hips start to stutter as well. 

“Cum with me. Please.” He begged and he reached down to your clit. He rubbed circles on your most sensitive area and that pushed you over the edge. Feeling your release, he pulled out just in time and sprayed his seed all over your stomach. As he finished, he laid his head down on your shoulder. You both were panting and covered in sweat.

After a few moments he got up and went to the bathroom. He grabbed a washcloth and soaked it in warm water before he returned and cleaned you up. Your eyelids felt so heavy with the weight of how intense the past moments were.

He climbed back into bed and wrapped his arms around you tightly, pulling you into him. After a few moments, when he thought you were asleep, he whispered a soft “Thank you” in your ear. You tried to hide the grin creeping up your face as you slowly drifted off to sleep in his warm embrace.

A/N: If you want to be added to my taglist please let me know! Hope you enjoy!