Ben's Date with Katy

One week has passed since that fateful day I downloaded the app. Ben and I where sitting in my car driving to meet up with Katy.

“So let me get this convoluted insane mess straight one more time”, began Ben. “You arranged a date with Katy for me, while also telling her that I get my rocks off by getting humiliated. Which just for the record, is not the case.”

“Yep.”

“So in order to make this date and I quote “more stimulating” for the both of us, you told Katy you would arrange another bet with me that I and I quote again “would absolutely lose” The Punishment for losing that bet would be that I would have to do anything Katy commands on our date. And just as a little bonus, I would also be unable to lie to her.”

“Unless its to cover up for the app.”

“Oh yes, because Katy still has no idea that thing exists. So anyway, because I am “not yet ready to embrace my humiliation fetish” Katy is supposed to be completely ignorant about our whole bet. And any commands she would give me would be purely by accident.”

“You know stuff like “feed me” and “what underwear are you wearing today?” *giggle*. You do have to admit its really cute.”

“If be cute you mean utterly horrifying, then yes, yes it is. Anyway, I am not supposed to know that Katy knows. That way she can create many “accidents” to make sure I am “happy.””

“I think that about sums it up.”

“And of course you made sure to use the app on me again. So that I couldn't disobey here, even if I wanted to.”

“That was needed to keep the illusion alive. If you where to suddenly act less obedient, she would know something is up, right?”

Ben groaned again. Of course we had this exact discussion numerous times all throughout past week. At this stage, there really was no point in complaining anymore.

“Oh we are here”, I announced as Millers College came into view. “I will follow you like a ninja, so don't worry. If things really go out of hand I can always give you a command.”

“Please just do nothing.”

Ben got out of the car and started to wait for Katy to finish practice. Meanwhile I parked my car a bit farther away and traced my steps back. Of course I wouldn't be a third wheel on this date, but I still had to made sure everything went smoothly. For the record, Katy was aware of that as well.

It took a few more minutes for Katy to show up. She wore a rather nice blue sundress. Ben for that matter was dressed for the occasion as well. It also looks like Vanessa was accompanying her.

“Hey, Ben! Did you have to wait long?”

Ben shook his head. “Ah, no I just arrived here.”

“Well, well, well, if It isn't Spiderman trying to woe Catwoman! Do you know that i'm currently wearing pink panties?”

Katy started to blush right away. “Vanessa....please....”

“Are you...alright?”

“Of course I am spidey-boy! Time to leave you two lovebirds to your date. I'm going to masturbate now, tata!”

Vanessa left just like that. What a weird girl.

“It was a rough week”, stated Katy as if that would explain anything. “So...where do you wanna go?”

“oh..i am ok with wherever you want to go.”

Ben you poor, insipid fool. Don't you know how important it is to take the initiative?

“hmmm..” Katy pondered for a bit. “It's a bit early but I am quite hungry, wanna grab something to eat?”

Ben readily agreed and so the duo wanders off.

Their destination was the College cafeteria

The frigging College cafeteria

“I hope this place is fine”, started Ben somewhat flustered clearly embarrassed about his idiotic choice.

“Sure.” Katy giggled. “I quite often eat here after training with Vanessa. Its cheap and tasty.”

“Oh yeah, about Vanessa...is she alright?”

Katy frowned. “I hope so. I think the doctors called it a form of tourette-syndrom. It's of course very embarrassing for her...”

“Yeah, I can imagine.”

Ben shot me an evil glare. Ungrateful little shit.

“This sandwich is pretty great.”

“Mine is good too.”

“...”

“umm....so what do you do for fun?”

“Oh..you know...videogames and reading.”

Holy cow, this date sucks. I should have knew that Ben is going to screw up this amazing opportunity I provided him with. Well, not under my watch.

I whipped out my phone.

“Give her five compliments.”

“So..i really like your big blue eyes, and your smile, you are also very intelligent and kind and you smell great.” The moment Ben realized what he just said he started to blush. “I...i'm sorry, I didn't know what that was...”

Well, that last one was a bit creepy, but whatever. Katy seemed to like it and giggled. “You like my...smell? I have you know I did shower after practice.”

“Oh..of course..that's what I meant. Its a very fresh smell!” Ben hastily corrected and took a big bite from his sandwich.

“Hm..” Katy suddenly had a somewhat more mischievous smile on her face. “So...you like smells?”

“mppfff...Yes...i mean...” Ben said mouth full.

“You...aren't into these foot fetishes things tough right?”

“N-No of course not!”

“ok,ok....but I am awfully curious now.” She grinned. “You know about your preferences.”

This wasn't a question yet so Ben decided to take the initiative. “You know...normal stuff...what about you?”

“Also normal stuff.” Katy smiled and sipped at her drink. “But you did say you kinda liked what happened to you..you know...last saturday.”

That got another blush out of Ben. “That was just...ugh...it was a little exciting that was all.”

“Nothing wrong with that.” Katy leaned a bit forward. “To be fair I did enjoy it quite a bit too.”

Ben only laughed nervously at that.

“Hey, Ben...is it ok if I try something out?”

“Sure...?”

“Alright..i want you to open your pants zipper.”

“Wah..?” Ben looked confused but his hands where already darting under the table.

“Make sure its all the way down, ok? ….You done?”

“Y-Yes.” Ben nodded.

“Good.” Katy smiled. “Now, how do you feel?”

“Pretty embarrassed.”

Katy giggled. “I can imagine, your blushing.”

“Can I close it yet?”

Katy gave Ben a knowing grin. “hmm..i wonder...maybe I should tell you to keep it open for the rest of the date?”

“Please, don't do that.”

“But you would obey right?”

“Y-yes”, Ben admitted wincing.

“That is...” Katy blushed. “I really like that about you, Ben.”

“That I am obedient?”

“That's not quite it...its just...” Katy took a deep breath. “You excite me Ben. It's hard to put in words I always liked you, but knowing that you are like this...”

As expected Ben had no idea how to react to that. Seriously, what does that girl see in him?

“Ben...” Katy continued. “It's early I know..but I want to show you my room.”

“R-right now?”

“Yes”, Katy stood up. “I'm afraid I can't wait any longer, lets go.”

“Can I at least put my Zipper back up?”

On that Katy gave him an extremely radiant smile. “No”

Yeah, I did not expect this sort of a outcome, but roughly 30 minutes after the date started the two where already moving towards the campus dormitory.

Now, I know from my stay here that bringing boys into the girls dormitory was not allowed. I also know that nobody really cared to enforce that rule tough.

“So here we are”, said Katy blushing and a bit breathless. “I'm sharing a room with Vanessa, but she should be at the hospital until evening.”

“That is good to know”, replied Ben equally blushing.

“So...please come in.”

And just with that the two vanished inside Katy's room.

Well that was fun.

I briefly contemplated sneaking in trough the window, but that didn't seem very promising, given that Katy's room was on the third floor. Oh well, of course I will have Ben give me a very detailed record of what is happening in there, but for now I guess I call it quits.

Before leaving the grounds I turned back one last time and grinned.

“Good luck, little bro.”