Afterglow

(Many thanks to JadedBlade for proofreading this chapter)

Cerve: “Just like that, Siree. Please remain seated on the toilet and do not touch your cage under any circumstance.”

It turns out peeing like a Sissy was remarkably simple. All you had to do was sit down and let it go. The snug cage applied some gentle downward pressure, which meant there was no risk of any spillage as your urine flew through the small hole on the cage designed for clean waste expulsion.

According to Cerve, the material of your cage was liquid-repellent and would never rust or decay in any capacity for a period of at least 200 years. While changes in the make up of the users body might cause some friction related issues, in theory, this cage was designed with the intent to never need to be removed.

Once the deed was done, the toilets bidet sprung into action and cleaned your dick and cage of any residue. You wondered a bit why Cerve insisted she also spray your ass, but apparently that was part of your toilet routine from now on.

TASK COMPLETED: Sissy Etiquette I SP

12 Points.

The next tier was still a long ways off.

...

Well, so…anyways.

After...that just happened in the bedroom, you quickly excused yourself to your bathroom to get some much needed cleaning done. You took another(short) shower before realizing that you needed to pee.

But that was the extent to which you could stall.

“Uh...sorry for the wait…”

You return to the bedroom, wearing uhh...this.

The reason you were even able to wear this was because of the special reward you got for completing the boss task.

Special Reward: Wardrobe upgrade

Congratulations! You are now allowed to add shorts and shorts related items to your wardrobe without overheating your chastity cage!

According to Cerve, completing the boss task gave your chastity cage a substantial power boost that allowed it to withstand more heat inducing clothing. Completing further Boss Tasks may power up your cage even more, allowing for more manly clothes.

A small part of your brain felt like this didn’t quite add up.

But that part was drowned out by the sheer euphoria you felt about no longer having to wear skirts!

Now yes, these shorts had to be short. Very short in fact. Definitely way shorter than you’re comfortable.

Still, progress was progress.

So why are you wearing this...thing, instead of just regular short shorts and a shirt?

Well, you still had to keep your ruse up for Jamie that you are a Sissy. And wearing a pink pajama(with nightcap) set would definitely reinforce that belief.

The fact that you cringed hard enough that you could crawl into a hole and cuddle a panda was of no consequence.

Speaking of Jamie. Your friend had at least deigned to put her boxers back on and looked at you with eyes big as saucers.

“That’s some extremely cute pajamas, Alex!”

“Ehehehe…”

You grinned bashfully.

Holy fuck, was this embarrassing! Why didn’t you just show up naked!

Cerve: “Because that would be extremely uncouth in the presence of a guest, Siri.”

A guest who also is your best friend turned fuckbuddy.

That said, a part of you wondered.

seduce someone 4 SP

pretty self explanatory

Shouldn’t you have earned these four points as well?

“Yeah, right? Hey, Jamie! What’s the deal?”

DON’T TELL HER!

In response to Cerve’s irresponsible question, Jamie let out a giggle.

“Did you think you seduced me?”

Seeing your face crumble like that, Jamie cleared her throat. “S-sorry. It’s just…” she hesitated. “From my point of view, I was the one doing the seducing.”

...what?

No matter how you look at it, didn’t you basically rope Jamie into your games? You weren’t exactly proud of that fact, but even so…

You definitely were the one instigating!

“Look Alex”, Jamie sighed. “We are both getting something out of this, so it’s more akin to a mutual beneficial arrangement? I don’t mind pretending you seduced me, but that would spoil your game, no?”

Fuck.

As far as Jamie is concerned, this was just you living out some of your fetishes.

In her eyes, you are a femdom obsessed Sissy.

Cerve. “Well said, Lady Jamie. If my master truly wishes to seduce you, he will just have to try harder.”

Great. Many thanks for nothing, Cerve.

Jamie giggled. “I am looking forward to that.”

“Oh, and on that note, you still have one very important duty to fulfill.”

Jamie looked surprised at your maid. “I have?”

“Duh! You gotta rate the performance! How well did Master do? Did he live up to the hype? Does he get a five star review?"

WHAT!

That’s the first time you’ve heard about this!

Cerve: “Allow me to clarify. You may award Siree within a range of negative five to positive five points. You may also rule the task a failure, which would incur an additional penalty.”

Holy fuck…

“And I have free reign here?”, Jamie asked.

Cerve: “Absolutely.”

Jamie’s face slowly turned into a smirk. “Hmm...whatever shall I do?”

You cringed. She’s surely not going to fail you, right?

After a few more seconds of ****, Jamie giggled. “So, first off, I’m not going to fail you, as funny as that would be.”

You sighed in relief. “Can you just give my five p...bzzt!”

Cerve: “Do not attempt to badger your client.”

C-Client?

“As for the performance itself…”, Jamie seemed to take this really seriously. “It was cute and all but I was really hoping you would suck me off. Also, not swallowing was a bit of a let down.”

Once again you cringed. You really did not want your jerking off skills to get evaluated.

After a bit more contemplation, Jamie finally nodded. “I think one point sounds about right. You get one point.”

Worship your superior’s penis: 1 SP

Only a single point.

Cerve: “Very generous, Lady Jamie. I personally would have failed Siree outright, or at the very least deducted five points for that shabby performance.”

Jamie grinned. “Oh, I’m aware, but he did look pretty cute on his knees, so I wanted to cut him some slack.”

You blushed. Just like that Jamie seems to have taken full control of the situation.

Bzzt!

Eep!

Cerve: “What are you doing? On your knees and thank your Mistress for her generosity.”

You had no intention to test Cerve, so you quickly went down on all fours.

“T-thank you for your generosity, M-Mistress. I..am...uh...unworthy of such uh...generosity.”

You lowered your head so low that your night cap fell off.

“Geez, talk about lame groveling!”

“He does still have a lot to learn about proper etiquette.”

Jamie on the other hand merely smiled and petted your head. “It’s alright. I like that part about Lexi.”

You weren’t sure if you were allowed to raise your head again, let alone get up, and so you just remained a bit like that while Jaime kept petting you.

...

..

.

After that, it was definitely way too awkward to just go back to playing videogames. It was also starting to get rather late. That said, you wouldn’t mind spending a bit more time with your friend.

“Hey, Jamie, wanna spend the night here?”

Jamie smiled at you and shook her head. “Nah, I’m having work tomorrow. I should head home.”

A part of you disliked that for multiple reasons.

“Ma’am? Can you call an Uber to bring Jamie home safely?”

Cerve: “Certainly, Siree.”

Upon hearing that, Jamie guffawed. “What? Now that you know I’m a girl you think I can’t walk home alone?"

“W-well…it’s just…you had a lot drink and...”

Jamie grinned at you.

“Ey!”

Then she suddenly lunged forward, pushing you on your back.

“Eeep!”

Pinning you securely to the bed, Jamie gave you a mischievous smile.

“Say, who’s the girly little Sissy between the two of us, hm?”, she asked.

You tried to get up. James, or rather Jamie, never had a lot of muscle. The two of you were rather similar in that regard. So, why couldn’t you push her off?

Jamie clearly enjoyed her superiority as she stared down at you. You could also tell that she was still very intoxicated. This was nothing like her usual self.

But then again, you apparently only learned about her actual self a couple hours ago.

“I wanna hear it Sissy Boy, or else”, Jamie threatened.

After your little fun, Jamie did redress herself, but even through her jeans you could make out the now throbbing cock.

“O-or else what?”

“Or else…”, Jamie leaned closer. “I’m going to show you what I can really do with my cock.”

“F-Fine! I’m a Sissy!”

“Are you?”, she asked. “Are you my weak little girly Sissy with a tiny babydick?”

“Y-Yes…”

“Say it properly.”

“I-I’m...your weak little Sissy with a tiny babydick.”

Jamie suddenly moved her head forward and kissed you.

It was pretty intense, tongue and all.

You could do nothing but take it, completely at her mercy.

Finally, she separated her lips and stared down at you, still unwilling to let you go. “Good boy...maybe next time I come over you can suck me off properly. Would that work, Cerve?”

Your AI assistant, who watched that entire spectacle without as much as a frown bowed politely. “Yes, Siree can perform this task again to update his score. Of course, a worse score would also be possible.”

Jamie grinned upon hearing that. “You better train hard then.”

And then, just like that, she rolled away from you, leaving you utterly befuddled.

Cerve: “Your ride will arrive in five minutes, Lady Jamie:”

YOU STILL ORDERED ONE?

Jamie stood up again and stretched herself. “Hmm...thanks. This was very fun, Lexi. We’re definitely doing this again!”

COMPLETED TASKS:

Tutorial 1 SP

Secret Star 4 SP

plug your nose shut and jump on one leg 100 times 1 SP

pills(one per day until box is empty) 1/20 SP

update your social media accounts: 1 SP

meet with a friend 3 Sp

Boss Task I 0 SP

Sissy Etiquette I 1 SP

Worship your superior’s penis 1 SP

Accumulated SP: 13

Special Reward: Wardrobe upgrade

Next Tier Unlocked: 20 SP

Tier 1 Tasks

pills(one per day until box is empty) 1 SP per day

say I am a Sissy 10 times while doing a handstand 1 SP

Play Super Sissy 69 Stage 1 5 SP

drink a gallon of cum 1 SP

Tier 2 Tasks

going out in girls clothes 3 SP

seduce someone 4 SP

eat a delicious cum flavored Hamburger 2 SP

anal orgasm: get 1 SP

quit your job 1 SP (in person, while dressed as a Sissy +8 Bonus points)

Negative Tasks

Gym Bunny: -1 SP for each day missed