The end of a long, short day

-recommend changing the ‘long and hard’ part of “but it felt long and hard and you thought it was indeed”, you say the exact same thing two paragraphs before, and two paragraphs before that one. The first one is ok enough, but I’d recommend doing something with that as well; just use synonyms or something

(yeah, that's an issue because the two chapters were merged, I changed it=

You watched Jamie depart safely and sighed. This evening certainly did not go the way you expected it to.

Cerve: “Your bed time has arrived, Siree.”

It has, huh?

Despite the fact that you were only up for half a day, you still felt remarkably tired. Today was exhaustive in more ways then one.

You attempted to climb into bed but Cerve subtly cleared her throat.

“W-what is it, Ma’am?”

Cerve only raised an arched eyebrow.

Cerve: You have yet to brush your teeth and relieve yourself, Siree.”

“Oh.”

You didn't want to be treated like a child but reasoned that arguing would only make it worse. Hence, you stumbled into the bathroom to finish your bedtime routine.

Once done, you were finally allowed to collapse onto your bed.

Not even five seconds later, something lashed forward, binding you at hand and feet.

“H-hey!”

Looking up, Cerve(in her maid outfit) was staring down at you.

Cerve: “As discussed earlier today, Siree. Restraining you during your sleep is a necessary precaution.”

These weren’t just some slack restraints either. You barely had any wiggle room.

“N-No way! There’s no way I can fall asleep like that!”, you complain, trying fruitlessly to free yourself.

Cerve smiled down at you.

Cerve: “Would you like to be pacified, Siree?”

Crap.

There was a certain glint in Cerve’s eyes. She was really looking forward to, uh...”pacifying” you.

You had no intention of letting yourself get knocked out again, so you vehemently shook your head.

Cerve: “I understand, Siree...”

YOU DON’T HAVE TO SOUND SO DISAPPOINTED!

You stubbornly closed your eyes, trying to just ignore the fact that you couldn’t move at all.

Sleep. You need to fall asleep.

But that was easier said then done. Cerve standing over you didn’t help either.

...

“Ma’am?”

Cerve: “Yes, Siri?”

“Could you leave?”

Cerve: “Certainly. Good night, Siree.”

The Hologram vanished, leaving you in silence. Finally, you allowed yourself to relax. Obviously, you had no illusions that Cerve was giving you any actual privacy. But falling asleep while a maid was standing right next to your bed was definitely not happening.

And speaking of falling asleep.

Yeah, that wasn’t happening regardless.

You felt tired but also very restless.

So much happened today but mostly…

The stuff with James...Jamie lingered in your mind. You really just sucked a dick, huh? Well, you didn’t actually suck it, more like licked it.

Sucking it would have given you more points.

Your own dick twitched as you recalled the events from just a short while ago. You were basically rock hard since the moment you knelt in front of Jamie. Fuck, you need to cum. You normally masturbate multiple times a day, and to be denied over and over was nothing short of ****.

…

Well, you weren’t exactly denied.

You had that one orgasm when you swallowed a pill.

But that was hours ago.

…

It should be Monday by now, right? That means you should be able to ingest another one of these pills.

“Ma’am?”

Your crotch buzzed lightly.

“Yes, what is it, sweetie?”

You licked your lips. “I...can I have another of these pills?”

Cerve: “As per our agreement, you are not to ingest more then one pill every 48 hours, Siree.”

“I...I know but...I...I really need to cum.”

“Oh sweetie, I am aware how hard this must be for you, but there’s little I can do…”

…

No, there was something...

But can you really say it?

...

You resigned yourself.

“What about Anal?”

“An anal orgasm is something only reserved for Sissy’s, sweetie.”

“I almost got one in the game”, you argued.

“But you were just playing the role of a Sissy. Real life is very different.”

“But...”

You battled with yourself.

“I...I already said that I am a Sissy numerous times. I even came out to Jamie.”

“That was just playing pretend, no? If you wish to cum ever again, you will have to fully embrace it. Embrace that you are nothing more then a blushing, little Sissy without a shred of masculinity.”

…

“I need to do it for the tasks.”

At that, Cerve fell silent. You thought that you actually had something here, so you pressed on.

“It’s not that I want to get a Sissy orgasm. But I have to do it to complete that task. This isn’t me being a Sissy. I just need to do it for points."

For a few seconds, there was nothing but silence.

Cerve: “That is a valid argument. However, it is already well past your bed time. We can provide you with an anal orgasm tomorrow. Please fall asleep, Siree."

Oh come on!

There is no way you can give up now!

“I’m telling you this because I can’t fall asleep”, you whined.

...

“Hmm...I think I can make an exception, just this once.”

And then, just like that, the restraints on your legs changed and lifted your lower half upwards.

“H-hey!”

It was an awkward position. Not at all how you expected your first proper anal fuck to go.

Something emerged out from the bed, but it was dark and you could barely make out what it was.

And as you felt something unbutton your pajama buttflap, you wondered if that was that good of an idea after all.

“Uh...Ma’am? Maybe we should...mpffff!!!”

You felt something long and hard invade your mouth.

Cerve: “Please ensure proper lubrication, Siree. Your cooperation is both appreciated and required.”

As the long, hard thing started to stir around in your mouth, you couldn’t help but feel that you just made a very big mistake.

You still weren’t quite sure what exactly was pushed into your mouth but you thought it was indeed a good idea to ensure whatever it was, was very well lubricated.

“Good girl”, Cerve purred as the rubbery utensil was pushed deeper into your throat. “Make sure your little friend is nice and wet.”

You wondered if Jamie would have felt the same...No, hers was definitely bigger. Although even this dildo or whatever was still much bigger then your own caged dick.

Why are you even making these comparisons! This is purely for the points! Even if it’s just one!

The dildo was shoved in deeper and deeper, to the point that you felt yourself **** on it. You desperately tried breathing through your nose, even as the dildo was pistoning in and out at considerable speed.

This was, quite literally, a facefucking.

Quite a long time passed before the dildo was finally allowed to retreat from your mouth. You immediately gasped loudly for air.

Cerve: “This is sufficient lubrication. Commencing insertion.”

Despite(or because) the rough treatment, your hole was already quivering with anticipation. If your mind wasn’t fogged up with lust you would perhaps show some restraint but, as it was all you could focus on was the impending pleasure.

You felt something gently poke your hole and you would have no doubt jumped out of your skin, if you weren’t restrained.

Cerve: “Would you like me to start, Siree?”

“Y-Yes!”

Cerve: “Then please ask properly, Siree.”

You gulped. Was there really any reason for that? Obviously not, Cerve just seemed to really like torturing you.

“P-Please…”

“Oh, you’re a lost cause! Repeat after me: Please fuck my Sissy boypussy with your hot, big rod!”

“P-Please fuck my Sissy boypussy with your hot, big rod!”

Cerve: “Affirmative.”

And then the pleasure came.

“Aaah!”

You already experienced this sensation in the Sissy VR game, so you expected to be somewhat ready for it.

You were not.

As advanced as the VR simulation may be, it was ultimately still a game. There was a certain disconnect present and you weren’t receiving quite the intense stimulation that your own body provided.

Cerve did not take her time, rather pegging your small hole with considerable speed and ****. The lubrication helped but even so, it was still very rough.

But that was exactly what you wanted. You wanted to be fucked like the slut you are.

You wanted pleasure, nothing else mattered to you.

“Are you enjoying being fucked by a Dildo?”

“Yes, yeeees”, you slurred out.

“My...aren’t you quite the horny bitch in heat?”

“Ah...haaa...yes...I’m just..a h-horny bitch...ah..ah…”

With how pent up you were it really didn’t take much. Already your climax was building. It wouldn't be quite as intense as when you had that pill, but that didn’t matter. All you wanted was relief.

Ah….aaaah….aaaaaaaahhh…

Cerve: “I invoke an AMM punishment: Orgasm Denial.”

And suddenly, the dildo was extracted from your needy asshole.

“Haaaaaaaaaa?”

You struggled against your restraints, fruitlessly humping the air.

“Put it back iiiiiin!”, you whined, all dignity forgotten.

Cerve: “As you wish. AMM Punishment: Dildo pacification.”

“W-what...hmppppffff!!!!”

The Dildo was indeed put into you. Back into your mouth, that was.

You could taste your own juices on it and something deep in your mind revolted against that.

But all in all you were simply too horny to care for that. Not when the denial of pleasure was a much larger concern.

“Hmhm...you are doing this now? A tad...mean spirited, don’t you think?”

What was going on?

Cerve: “Siree, do you remember our conversation yesterday? When we agreed that you would address me with Ma’am?”

“Mpfff!!!”

Cerve: “You were rather neglectful in your duties and have accumulated a total of 37 Ma’am misses(AMM). That is an unacceptably high number of infractions.”

“MPPPPPFFFFF!!!!!”

Cerve: “In order to ensure proper behavior in the future, a punishment system has been implemented. You will be punished in various ways until your AMM debt is cleared.”

N-No!

This had to be a joke!

“Mpfff...Mppffffffmpfff!!!!”

Cerve: "Incidentally, you are currently accumulating quite a few AMM's. I would advise you to remain silent, Siree."

"Mpflffppfff!!!"

Cerve: "As you wish."

You struggled against your restraints, but of course, there was nothing you could do. Your dildo turned pacifier simply kept fucking your mouth.

“Hmm….yes...sorry about that, sweetie...but you just have to deal with it for tonight.”

“Nyehehehehe! At least you won’t get bored!”

“MPPPPPFFFMPPPPFFFMPPPPFFFF!!!!”

Cerve: “Good night, Siri.”