Cindy's Monday [CW: Anilingus]

Cindy gets dressed for the day like normal.

But today is no normal day.

She knows that this had to be done. Rationally, she knows that. But still, that doesn't make it any easier to actually walk out there, now that half the women in the academy have signed that ludicrous contract.

One burning question remains - how many of her peers are actually sadistic enough to make her...

Ugh. Even just thinking about it makes her grimace. She allows herself to make a disgusted face and sound. Because once she goes out there, she'll have to be using all her best acting skills, to convince her Sentinel... To convince the buttholes themselves... That she's having a great time.

Mustering up her courage, Cindy opens the door to her bedroom, and steps out onto the upper landing of her shared cottage.

Thank goodness I'm not one of the freshers living in the basic dormitory blocks. She thinks to herself as she descends the stairs. At least there's only three other women here with me, and out of the, only Samantha is weird enough to even consider showing me her ass, I think. Fingers crossed I'll be able to eat my breakfast in peace...

But then, suddenly, Samantha is exiting the bathroom in front of her, already fully dressed for her first day of class apparently, in a nice blue and white dress.

There's a small coat 'closet' next to Cindy, next to the front door, which is actually just an alcove with a curtain concealing the contents behind. Cindy quickly slips behind the curtain before Samantha notices her, and squats down to try and avoid making a visible silhouette against the curtain.

When Sam doesn't immediately say anything, Cindy breathes a silent sigh of relief.

That was too close.

But then... She hears a snicker.

"Well, I guess it's time for me to get my coat and head out!" Samantha declares out loud to nobody. And that doesn't even make sense - it's early September, in a part of the country that stays warm (or hot) all year round, and it's sunny outside. Nobody is wearing coats in this weather.

And then suddenly, Samantha has slipped behind the curtain, too. She feigns shock, but it's clear that she saw Cindy slip in here all along.

"Oh, Samantha! You're getting your coat too, are you?" Cindy asks playfully.

The alcove is small. With the items of clothing and shelving units, there's hardly enough space for both of them in there. And because Cindy is squatting, her head is at Samantha's crotch.

Cindy finds herself lost for words for a moment, and then eventually gets out a simple, quiet "Please, don't."

"You don't want to talk to me?" The woman she's been building a friendship with for the past week asks in a mock offended tone.

"I've..." I've had a bad day. Cindy was about to say, but she cuts herself off as Samantha turns her back on her, and lifts up her dress, exposing a saucy pink thong.

"Then maybe you'd prefer to talk to 'Little Miss Sammy'. What do you think?"

Samantha spreads her ass cheeks, which causes most of her asshole to be visible for the briefest of moments.

Clang! A gentle chime sounds from Cindy's bracelet.

"Cindy, you are enamoured." The posh British voice says calmly.

That's it. That's the signal. Now she has to do it. It's really happening for the first time. And to her housemate, no less, who is a lot more cruel and sadistic than she had realized.

"Sorry, but I just had to be the first. And I'm pretty sure this is going to me my only opportunity to take your ass kissing virginity, hahaha!" Samantha chuckles playfully, as if this isn't the most horrible thing she's ever done in her life.

Cindy knows what she has to do. To the best of her ability, she switches her rational brain off, to try and protect its sanity, and goes into actress mode.

"Oh Little Miss Sammy, did I see you there?" She coos. "It's just... Now that I've seen you... I can't stop thinking about kissing you. Would you do that for me, Little Miss Sammy? Grant me the honor of a kiss? I would be ever so grateful."

Samantha responds by pulling her pink thong to the side, and bending over a little bit more, so that her butthole... 'Little Miss Sammy'... Is fully exposed and accessible. Not that she had to give any further consent anyway, after singing that contract. But she clearly wants Cindy to know that she's fully invested in this interaction.

"Oh thank you so much, thank you thank you thank you!" Cindy coos, and moves her face in closer, puckering her lips.

Now that the moment is here, Cindy baulks. She knows she's not supposed to hesitate at all, but this is just insane! She's never put her mouth anywhere near anyone's butthole in her life, even her most treasured lovers... And also, she's not even into women! Everything about this is so ridiculous... How is she supposed to go through with it?

No, don't think, just do it! Cindy screams at herself, inside her own mind.

Her lips touch the butthole. She plants the kiss, and tries to make a 'mwah' sound. It's just as horrendous as she expected. And, she's not done yet. The contract was very specific about what things would cause offence if not done properly.

And so, Cindy's tongue flicks out and licks the wrinkles on Samantha's sphincter.

It's undeniably perfectly clean, and not even sweaty - Samantha must literally just have showered - but feeling those bumpy creases with her sensitive tongue is still the most unpleasant thing she's ever done with her mouth in her life. And no wonder - she literally just licked a butthole!

She's supposed to give the buttholes at least three licks, and so she gives it two more, quick and simple, but hopefully clearly distinct. One final quick peck with her lips, and then she quickly pulls away, her face contorted into disgust.

"Is that it?" Samantha asks disappointedly.

"Um, thank you for letting me kiss you." Cindy mutters dejectedly, but remembering that there's one last part of the ritual to fulfil, "It was great."

Her Sentinel speaks up almost immediately. "I'm so sorry Miss Cindy, but the combination of your hesitance, your foul facial expression, and the lacklustre compliment afterwards has left Samantha's anus offended. I'm going to have to ask you to complete the forgiveness ritual."

Color drains from Cindy's face. She had fucked up already! That wasn't enthusiastic enough?! She'd tried to do it properly, but it's difficult to hide how much you hate something! Fuck!

But what would be even worse than having to go through with the forgiveness ritual, is what happens if she fails to go through with it properly. She would become Samantha's oral **** for a whole 24 hours, **** to follow her around, lick her anus and genitals on command, and if Samantha wanted, do some even more niche and nasty things with her mouth too.

Fear of that eventuality drives her forward, and helps her throw hesitation to the wind.

"Oh Little Miss Sammy, I am so so so so so so so sorry for offending you! Please, accept my humblesed of apologies! How can I make this right? I'll do anything! Anything!"

She leaves a dramatic pause, before continuing.

"Of course! Of course! I'd love to! It would be my pleasure! Right away!" Cindy coos as earnestly as she can... And then without allowing her irrational brain to second guess this decision, she extends her tongue and pushes it as deep as it will go into Samantha's asshole.

"Oh fuck yes. This is more like it!" Samantha sighs with pleasure.

Cindy has memorized the contracts wording, and is now hyperfocused on fulfilling it. She knows that the next ten seconds needs to be noisy and shameless. She puts everything she has into it, making pornstar moans as she swirls, thrusts and digs her tongue around inside her new friend's backdoor.

"Oh my god, I can't believe you're actually having to do this, hahaha!" Samantha sounds gleeful. What a cruel bitch.

Cindy ignores her, and continues her aggressive shameless butt munching. She also tries her best to not think about the unmistakable bitter taste of ass that her tongue is getting saturated in.

$100 000. I've already won six figures. And I'll win more. This is worth it. She tells herself over and over, as her tongue swirls around this woman's backdoor, over and over.

Only once Cindy is absolutely positively sure there's no way that 10 seconds haven't passed, does she pull her tongue out of Samantha's brown star.

"Oh my god, you taste amazing!" Cindy croons in her most over-the-top enthusiastic voice. "Thank you so so so much for the honor! And I'm truly, truly sorry for offending such an upstanding member of the community such as yourself. Thank you for allowing me to make it right."

A polite ding from her Sentinel lets her know that she's done the job successfully. She sighs with relief.

"That was delightful." Samantha sighs pleasantly, without even looking at the ginger woman on her knees behind her. "I'm so glad I got to be your first. Same again tomorrow, yeah? Hahaha!"

"Fuck you." Cindy snarls back, but Samantha just chuckles. It must be diffiult to take someone seriously when they've just been tongue-blasting your butthole like that.

Samantha is already sliding her thong and dress back into place, and slipping back out from behind the curtain, into the rest of the house.

"Catch you later, ass-kisser!" Cindy hears Samantha call one last time, and then the front door opens and closes, leaving Cindy kneeling all alone in the coat closet, the taste of Samantha's ass still fresh on her tongue.