My Kind Of Hell! (Male!Reader x Fem!Creepypasta)

Jill's Date

A/N: Hey guys! So now we come to this. The date with Jill. Will it go as well as Ann's date, or will it go horribly, horribly wrong? I guess we won't know just yet!

Yami: Would you actually make it go to shit?

A/N: Maybe I will. Who knows? Maybe you'll melt into a puddle during it! Who knows?

Yami: You do...

A/N: Ah... right... Enjoy!

Jill's POV

While I was waiting for Y/N so we could start the date, I went over to Benny in her room, trying to put my plan into action. I walked in and saw Benny look over, noticing me.

Benny: Oh, hey Jill. What's up?

Jill: I need your help.

Benny: Help? With what?

Jill: You're good at pranks, right?

Benny: Yeah? Why do you ask?

Jill: Could you by any chance help me out with my date with Y/N?

Benny seemed to freeze up for a moment before responding quickly after she got over her shock.

Benny: No! No way! Remember last time I pranked Y/N!?

Jill: Yeah, but that was different! This is just a date! It's nothing that'll hurt him! 

Benny: Nope! 

I pouted, trying to get her to help me get 'alone' with Y/N during the date, but she wouldn't give in. I was almost completely defeated before an idea popped into my head. I gave Benny a sly smirk before nudging her.

Jill: Y'know... I could get you and Y/N on a date soon if you help me.

Benny seemed to consider the idea for a moment.

Benny: How would you do that?

Jill: I can put in some really good words for you and set it all up after our date.

Benny: A-And this would get me a date with him?

Jil: No question. He'll do it. And maybe even do you too~

Benny blushed before agreeing to the idea. After going over the plan with her, I left the room in victory, leaving behind a flustered Benny. I went to the living room and sat down on the couch, waiting for Y/N.

Y/N's POV

After I got changed into some nicer clothes, I went to the living room, seeing Jill on the couch.

Y/N: Sorry for the wait.

Jill perked up and noticed me standing in the entryway of the room. She seemed to blush slightly while smirking.

Jill: Well don't you look handsome~

Y/N: You saying I don't always look handsome?

She giggled before walking up to me, swaying her hips as she moved. She got right next to me and wrapped her arms around mine, pushing her breasts into my side. I blushed a bit before I took her to the theater. For the first part of the date, I wanted to play a song for her. It was a nice one I learned for fun, and it wasn't crude or offensive. Just piano and nothing more.

After I finished the song, Jill clapped for me as I did an over exaggerated bow. Once we left the theater, we went to the pool. This is the place I most expected things to go south, given the obvious lack of clothing on both of us. But it went as well as it could've gone. We did a little diving competition, seeing who could do the fanciest trick. Jill won, but I decided to 'reward' her for her victory. I walked up to her at the edge of the pool, wrapping my arms around her waist.