Bill Hader Imagines

Truth Or Dare (Willy)*

Warning: Smut, Language

Y/N decided to stay after the pool closed to hang out with Willy. She had worked with him at the pool for almost two months, and she discovered that he was a lot of fun to hang out with, plus he was really cute.

She was sitting beside the pool, letting her feet sway in the water when Willy sat down beside her. He offered her a beer, and she gladly took it. They both dipped their beers and stared at the night sky. Willy turned towards Y/N and a small smile came to his lips.

"Hey Y/N. Truth or dare?"

Y/N turned towards him, and gave him a look.

"What are we twelve years old and in middle school?"
"Come on, Y/N. Just do it. Don't be a pussy. Truth or dare?"
"Fine, truth."
"You're no fun. Uh, are you a virgin?"
"No."

Y/N took a big drink of her beer after she answered Willy's question. She sat her beer down and looked at him.

"Truth or dare?"
"Truth."
"Do you really live here at the pool?"
"Yeah, I'm trying to prove that I can be independent. Truth or dare?"

Y/N took another drink before answering Willy. She looked at him, and a smile formed on her face.

"Dare."

Willy took a drink and tried to think of the perfect date for Y/N. A thought hit him, and sly smile came to his face.

"I dare you to skinny dip."
"What? Are you serious? Right now?"
"Yep."

Y/N huffed out a big sighed and downed the rest her drink. She stood up and took off her shirt. A surprised look came to Willy's face as he watched her. She took off her shorts and untied her bathing suit top, pulling it off. Willy shifted in an attempt to hide his growing erection.

Willy thought that Y/N was hot, and he couldn't deny it. He had been dying to ask her out, but he got super nervous every time he tried. He didn't think at she would actually do his dare, and he was shocked to see her actually doing it.

Y/N removed her bathing suit bottoms, and Willy watched her as she jumped into the pool. She resurfaced and swam over to the edge where Willy was sitting. She rested her arms on the edge and smiled at him.

"Truth or dare?"
"Dare."
"I dare you to join me."

Willy jumped to his feet and kicked off his sandals. He pulled off his cardigan and shirt. He paused, remembering something important.

"If I jump in, you'll have to help me because I can't swim good."
"Don't worry, I'll get you."

Willy tugged his shorts and boxers off, and Y/N's eyes widened at the size of Willy's dick. She shook her thoughts from her head as he eased himself to the edge. He carefully jumped into the water, and Y/N quickly swam over to him.

He resurfaced, and Y/N grabbed him and pulled him over to the edge. Willy gripped the edge with one as he used the other one to wipe the water off his face.

Willy smiled at her, and they laughed. He pulled Y/N closer to him, and he leaned into her, kissing her lips. Y/N wrapped her arms around him and deepened their kiss. Willy pulled away slightly and looked at her.

"Could we move to the shallow end before continuing?"

Y/N nodded at him, and they eased their way to the shallow end on the pool. Once Willy could touch the bottom on the pool, he pulled Y/N all the way into him and connected their lips again in a heated kiss.

She wrapped her arms around his neck as he moved to leave hot, wet kisses down her neck. He walked them into a corner of the pool and moved his hands to massage her breasts. Y/N moaned as Willy kissed down her chest and captured her right nipple in his mouth. He kept massaging her left breast as he worked on the right one with his mouth. He switched his mouth to her left breast, showing it the same amount of attention.

"Willy, kiss me please."

Willy released her breast and kissed her deeply. He slid his tongue across her bottom lip, and she opened her mouth wide enough for him to slip his tongue in.

He slid his hand down her body, and he ran his fingers through her folds. She moaned as he began circling her clit.

"Oh fuck, Willy. Oh my God."
"You're so hot, Y/N."

Willy removed his hand, and he began stroking himself. He lifted her leg around his waist and suddenly, realization hit Y/N.

"Willy, wait."
"Why, what's wrong? If you don't want to this then we don't have too."
"No, I want to do this. It's just that we don't have a condom."
"I have some hidden in the desk in there."

Willy let Y/N's leg down, and she hopped out of the pool, walking into the pool house. She shortly returned with the condom in her hand. She slid back into the pool, and she opened the package. Willy slightly lifted himself out of the water, and Y/N slid the condom onto him.

Willy lifted Y/N's legs around his waist, and he lined himself up with her entrance. He slid into her causing both of them to moan.

"Fuck, Willy. You're so big."
"You feel amazing, Y/N. Fuck."

Willy began moving, and Y/N's head fell back. Willy kissed her exposed neck as he kept pushing in and pulling out at a slow pace.

"Please, go faster. Please, Willy."
"Anything for you, baby."

Willy picked up his pace causing U/N to loudly moan. He silenced her by capturing her lips in a heated kiss. She moved her hands to his hair and gripped the long strands as he kept fucking her.

"I'm so close. I'm gonna cum."
"Me too. Do it. Cum for me, Y/N."

A whine came from Y/N's mouth as Willy quicken his pace some more. She felt warmth spread across her lower stomach, and she came with a loud moan that Willy attempted to silence. His hips jerked into as he came. He kiss her again then he laid his head on her should as he tried to catch his breath.

"Y/N, that was-"
"Amazing, I know."

He pulled out of her, and they exited the pool. They walked into the pool house, and Willy handed her a towel. They dried off and walked back out to the side of the pool, and they put their clothes back on. Willy laughed as a thought came to his head.

"I have to chemically treat the water now. Did you heard? Two horny people had sex in it."

Y/N playfully rolled her eyes at him as she laughed.

"You know, if you hurry, we can go back to my place."
"Really? This isn't some one night, one time type thing?"
"I don't want to to be. Do you?"
"No, I don't."

Y/N smiled at Willy as he walked into the pool's maintenance room. She cleaned up their mess of beer cans, and Willy snuck up behind her and wrapped his arms around her, frightening her. She turned in his arms, and he kiss her again.

Willy really liked kissing Y/N, and he wanted to do for the rest of his life.