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.

Jill: Huh? Oh, getting excited are we~

I merely smirked in response.

Jill: Well, are you sure you want to do it here-

I then lifted her up, an evil smile on my face.

Jill: Uh... Y-Y/N?

I held my grin as I lifted her out of the water and brought her out into the middle of the pool.

Y/N: GERMAN SUPLEX!

I suplexed her into the water, both of us quickly coming up for air. Jill had a slightly mad look, but it was more pouty than angry. We both laughed it off before getting out of the pool and drying off. I was about to go get changed when Jill stopped me.

Y/N: What is it, Jill?

Jill: You know... you haven't been in the sauna yet~

Y/N: Ah, right... well, I guess I could go for a bit of relaxing. It's been a long time since I've been in a sauna anyways.

We both went into the change rooms, both of us coming back out in only our towels. I could tell Jill got a slightly smaller towel than she needed just for this, as her cleavage was plainly visible. It looked like the towel would actually rip if her bust was any bigger. How it was still wrapped around her, I have no idea. 

We went into the sauna, Jill sitting next to me as the room heated up. It wasn't on before we got in, so it needed a minute before it heated up fully. Once it was hot and steamy... the literal terms! Get your mind out of the gutter! Ah fuck, there goes the wall... Anyways, once the room was an actual sauna, Jill leaned on my shoulder, clearly aiming to give me a full view of her bust as it threatened to break from the small towel around her. I blushed a deep red, but it wasn't obvious since my face was slightly red from the heat already. I quickly tried to think of something to talk about.

Y/N: S-So, did you enjoy the date?

Jill: I did, you really know how to have a fun time~

Y/N: W-Well, I guess if it wasn't for you, we may never have done this.

Jill: Y'know, I think I've done things just right today.

Y/N: How so?

Jill: Well, we had a date where you played a song for me, had fun in the pool with a friendly competition... Now all that's really left is dinner before we've gone through every step... But I've been thinking...

She raised her hand to her towel, tugging at the edge of it slightly.

Jill: Maybe we skip dinner and go straight to the fun part~

My face was now completely red. No amount of heat could rival my face right now. I knew exactly what she was playing at and I was not only expecting this but ready for it too. However, the heat and steam from the sauna are making Jill appear more seductive, and thanks to how hot it was, I was slightly lightheaded. It didn't help that she was right either. At this point, things have gone great. The date so far has been perfect, and I had a very similar mindset to Ann's date at this same point.

Benny's POV

I was outside the sauna now, Jill and Y/N both inside. My role here was simple enough. Pull it off, and I would get a date with Y/N. It's simple as that. Right? I've been thinking about this for hours now. I'm scared of a repeat worse than last time, but I also want to get a date with Y/N... I thought about what Y/N would think before I remembered something.

After thinking about what he said to me after the knife incident, I realized that he was an understanding person. He would accept a request from me to go on a date for sure! He's too nice to decline. Hell, he might even ask me out instead. After considering my options, I nodded before going into the change rooms, coming back out in a towel only.

Benny: I've decided! I'll be with Y/N on my own terms!

I opened the door of the sauna, seeing Jill trying and partially succeeding to seduce a flustered Y/N. They noticed I opened the door as Y/N looked at me, his face got even redder before his entire head burst into flames and he passed out. Jill and I looked at Y/N and then to each other a few times.

Benny: What did you do to him?

A/N: Hey! Thanks for reading! If you thought that you'd be fucking Jill then you were wrong and you should feel ashamed! Even though I hinted that it might end in a lemon or lead into a lemon...

Yami: You still totally plan on getting Jill under the sheets don't you?

A/N: It's not like I didn't do a big cringey lemon with Ann. Every girl get's it, just not all at once!

Yami: I think I'll just prepare myself for it by reading Blake's books...

A/N: You have fun with that... And you dear reader! Have fun trying to guess when the lemon is coming! Signing off!

- Iain