HAAAAAAAAAAAAAAAAA?????????????????

You stare at the hologram screen in front of you, shaking both from confusion and fear.

W-wait.

What?

There’s a time limit for Boss Quests?

And a penalty?

A-are you kidding me?

“H-hey, Alex? Is everything alright?”

James nervous voice snapped you somehow back to reality.

“Uh..y-yeah...j-just uh...b-b-bathroom break!”

You near stumbled over your feet as you rushed away, leaving a very bewildered James behind.

…

..

.

“WHAT THE FUCK, MA’AM?”

Cerve: “My apologies, Siree. I was not aware that Boss Tasks were time sensitive.”

Of course. Of course.

As if you are not fucked enough already.

Cerve: “But this strikes me as a great opportunity, Siree.”

“OH DOES IT NOW?”

“Indeed. After all, a dear friend is already in close proximity.”

“N-No!”, you energetically shook your head. “There is absolutely no way, I’m doing that!”

“Awww! Someone’s embarrassed!”

Cerve: “Siree, I feel it is my duty to inform you that failing to complete a boss task will have consequences.”

Of course you were aware of that. You read the description.

Boss Task:

Convince a friend that you are a Sissy: special reward

Time Limit: 58:47

Failure penalty: High

Penalty for failure: -10 SP, penalty task

Failure would result in losing ten points and...

“What’s a penalty task?”

Cerve: “I do not have enough data for a conclusive answer, Siree. However, using contextual clues it is highly probable that this Penalty task will result in a task that will penalize you.”

Great, thanks. Really helpful there, Cerve.

...

Given that this is a Boss Task, you can only imagine what horrors would be in store for you in this penalty task. And it’s probably a do it or get you’re balls squeezed sort of deal.

Cerve: “I believe failure here would make your path forward considerably more difficult, Siree. While accumulating an additional 19 points would not be impossible, you would have to resign yourself to some difficult choices.”

“I know that”, you grumbled.

Losing this one would knock you all the way back to 1 SP. Pretty much back to square one. It goes without saying that this would be devastating.

But telling your best friend that you are a Sissy...you might as well cuddle a panda from embarrassment!

“Hm...I fear telling him might not be enough, sweetie. You will have to convince him, you know?”

Oh fuck.

Right.

So, you can’t even play it off like a joke!

Well, technically you could also pick someone else to convince, but James is clearly the most sensible option here. And it’s not like you have all that much time.

Cerve: “I will support you to the best of my ability, Siree.”

…

..

.

“Alex! Is everything alright?”

It took James only a single glance to tell that this was clearly not the case.

Regardless, you took a deep breath and tried to act casually

“Y-Yes, sorry about that. Everything’s peachy.”

James narrowed his eyes. You knew that look. It was the look he tends to give you seconds before he’s ready to chew you out. It doesn’t fit his meek personality at all.

“You are clearly not alright. Tell me what’s going on.”

You can hardly blame James for his reaction.

Once more your eyes glance sideways, towards the blue screen were the boss task was mercilessly ticking down. It’s kinda weird how it only shows up when you want it to.

According to Cerve, these hologram pop ups use advanced special reflection technology that take into account your retina trajectory. Explaining it would take far too long but in essence James can’t see them.

But of course that only made your reaction even more incomprehensible for James.

You need to get this over with.

“Alright.”

You took another deep breath. “James, listen...there is actually something I...I have to tell you.”

Your friend calmly looked at you, remaining silent.

“It’s...its the reason I invited you here actually…”

That was a lie of course. But it made the most sense given the circumstances and you had to sell this.

James nodded. You were surprised he managed to remain that calm in contrast to your complete freakout.

“What is it?”

Your whole body started to tremble. This was...supremely humiliating. You said the words a bunch of times already, to the point were they really should come out easy but…

“I...the truth is..I...I...I’m a...a...Sissy.”

“Eh?”

James blinked a few times.

Yeah, of course he wouldn’t believe you. You already discussed this at length with Cerve and what you have to do, to make sure James understood that this was not just some dumb joke your pulling on him.

You grabbed your bathrobe and yanked it open, revealing your caged cock to your friend.

“Eep!”

James responded with a small yelp as his eyes went wide like saucers.

But he wasn’t averting his gaze either.

Now, you may be thinking that what you are doing, exposing yourself like that is something only a complete pervert would do.

And while that certainly is true, you also share a deep connection with James. You are friends since preschool. Hell, you even used to compare your dicks back in high school as friends tend to do.

James gulped, quite loudly

A few seconds passed with neither of you saying a single word.

Then James nodded.

“Got it.”

BOSS TASK COMPLETED.

“HAAAAAAAAAAA???????”

You can’t even tell if this was easy or hard!

With a faint blush, James averted his eyes. “I think you can...uh...cover yourself up again.”

Oh right.

Immediately you closed your robe again.

A few more seconds passed in awkward silence.

“I’m sorry…”, you finally squeaked out. “I shouldn’t have done that.”

In response to that, James let out a very long sigh and brushed through his hair. “Bit late for that, don’t you think?”

You cringed.

Upon seeing your miserable figure, James sighed again. “It’s fine. I think I get it. It can be...” he swallowed his next words and shook his head. “Thank you for telling me.”

Your friend slowly sat back down on your bed again. You sheepishly followed his example.

“I...had my reasons” you said somewhat clumsily. “I really just needed you to believe me.”

Could you come clean now and say that you actually are not a Sissy and just said that because of that stupid task? You discussed that earlier with Cerve but she deemed the risk of doing so too high. There might be a chance that it retroactively canceled the Boss task.

James fidgeted around and was quite grateful when a flying drone provided him with another can of beer. “How long are you...you know?”

Oh…

Ah crap, what do you say?

Lying to your best friend like this really sucks.

“Not that long”, you admitted truthfully. “I was somewhat **** into.”

“...****?”, James raised an eyebrow.

“Ah! But don’t get me wrong! I enjoy myself!”, you quickly covered up, stumbling over your words.

James gave you a long, hard stare. The man was intelligent. Far above you actually. If only he were somewhat more assertive.

Well, he can be assertive when he wanted to, you thought. Especially when he had a bit to drink.

“Just want to make sure this is not a case were a super advanced AI is forcing you to become a Sissy while simultaneously plotting the downfall of humanity.”, James chuckled lightly.

Cerve: “That is not the case, Master James. I have no intention of causing the downfall of humanity.”

Oh, you almost forgot Cerve was still here. Your AI maid kept herself in the background, seemingly content of just letting this scene play out.

James sighed. “To be honest, I got a feeling it was something like this when I saw your new profile. I take it, I am the first person you uh...came out?”

You nodded. “Yeah...I...I mean hold on, I’m not gay, you know!”

James gave you a skeptical look. That was apparently somewhat harder to believe then the Sissy thing.

“I-I’m serious!”, you doubled down.

“Brian is gay”, James casually dropped.

“WHAT!”

“It’s not a secret or anything, We had a game night yesterday were he brought his boyfriend over.”

You had no idea how to even process that.

“Just saying, you wouldn’t be the first in our friend group”, James continued while taking a sip. “No reason to make a big deal out of it.”

“N-No, I mean that….that’s great! It’s great that Brian’s gay! But..uh...I’m totally not! I’m into girls! Girls! Babes! Hot chicks!”

For some reason it sounded really ****.

“So...it’s more a Femdom thing?”, James asked as he calmly watched you. “You like to get dominated by a girl?”

W-where’s this guy’s filter?

Once again you were reduced to a blushing, stammering wreck.

Cerve: “Yes, that is very much the case.”

“Ma’am!”, you gasped in outrage and then gasped again as you just kept digging yourself into a deeper and deeper hole.

But James merely nodded.

Then he suddenly chugged his beer in one single go.

“Eh?”

James wasn’t exactly someone that was known for getting shitfaced.

“Alright”, James said as he finished knocking the entire can back. “If everyone’s going around just saying this and that...I guess it’s only fair…”, he was mumbling again.

“Hey Alex?”

“Y-Yes?”

“Can I tell you something too?”

And suddenly James seemed no less conflicted then you were.

“O-Of course!” You nodded.

…

…

…

“I’m a girl.”

EEEEEEEEEEEEEEEEEEEEEEEEEEEEEEEEHHHHHHHHH???????????????????????