Sir, Sir, Won't You Do This For Me?

"I need your help, and I need you to not judge me for it."

This doesn't even breach the top ten worst ways to begin a conversation you've ever encountered, but it's still a runner up. So you close your eyes, count up to three, and then force yourself to face whatever nonsense you have been blessed (derogatory) with today. "Alright. What is it?"

Artoria (Caster, she who chants, child of prophecy, your life, your fate, your core) stands in front of your door, suddenly looking terribly awkward. For a few seconds, she does nothing but stare at her shoes- which look great, by the way. She's wearing a three-pieces suit for some reason, in fact, and it looks unreasonably good on her, though now is clearly not the time to be horny.

Eventually though, Artoria reaches inside her pocket (which must be way deeper than it looks on the outside, because holy shit she just fit her entire forearm here) and hands something to you. "I... don't know how to put it on. Help me. Please."

You look down. Then back at Artoria's face. Then back at the strap-on in her hand. "... sure. That's in my wheelhouse."

You take the offending item, then get the girl to step in each "leg." Her movements are stiff. Her face is bright red. She is, quite obviously, mortified that she had to ask for your help. You're torn between teasing her or reassuring her.

Either way, you should probably say something. The silent is a bit anxiety-inducing, and, worse, it is boring. "So," you ask, kneeling by her right side to adjust the first half of the fastenings, "who'd you plan on using that on?"

"Ah? Uhm. No one, I guess." Her voice is high-pitched with embarassment. It's cute. "I just, uhm. Okay. You. You know that one time I had to crossdress for a singularity?"

"I do." Ah, right, that's where the suit is from! Initially, you were the one supposed to wear it. Sadly, while you don't care much for gender, you have your moments where you care strongly about whatever you're performing at the moment. Meaning: asking you to wear a suit on a day where you're feeling feminine makes you violently dysphoric, so you pawned the role on Artoria instead.

The girl brings her hands together, twiddling her thumbs nervously. "Well I realized that I, uhm. Looked good. In a suit."

"That you do." Uh-huh. So far you follow.

"No, I, meant," it sounds like she's talking through grit teeth, "I really liked it. I really, really liked it."

... OH.

You almost say congrats on your new fetish, but then you remember her request not to judge, so instead you say: "so the strap-on is? To complete the look?"

"...Basically." If she turns any redder, you'll have to call medical bay. It's adorable.

"You should have led with that." You say, circling her to start fastening her other hip. "I could have tried to get this under your pants. That way you'd be able to walk around with it, instead of being confined to my bedroom."

She doesn't reply, for some reason. "Though, maybe you'd need a different dildo?" You wonder out loud, focused on your work. "You probably need one that bends a bit if you want to have a bulge look. I'll ask around, I'm sure someone will have tips on that."

"... That is... appreciated."

Your work done, you come back in front of her, still kneeling. The whole thing should hold well enough to walk around, but you're not quite sure if it's fit perfectly. Since you are nothing if not a professional, you wrap your hand around her dildo and look up at her. "Fuck my hand."

She startles at your words, and you feel the silicone dick jump with her, which- hm. Anyways. "What?!"

"I asked you to fuck my hand. I need to know if the fastenings are tight enough. If they're too loose, your dick is gonna wobble around, and it won't feel at all like it's yours."

Your reasoning is sound, so even if it gets her sputtering and avoiding your gaze, Artoria complies. She thrusts her hips forward, sliding her cock between your fingers. 

You feel it, see it get closer to your face, see flex of her legs beneath her pants, see her hands hovering at her sides not knowing where to go, and- focus. Focus. Your bestie is in need of help, don't make it weird. You can tease, but you can't make it weird. "I... need to tighten the whole thing a bit. Give me a second."

You go around her again, working your fingers on her strap. It's important that she has as much control as possible over her dick, for... realism, and all. You try really, really hard to focus. The strap hugs her behind and emphasizes her ass, which, while objectively quite flat, is still Artoria's and therefore of interest to you. Focus, Fujimaru. Focus. At least for now.

"Try again?" You wrap your hands around her dick once more. This time, when she thrusts her hips, the dildo is held firmly in place by the harness. "Okay, that should be good now."

"Th-thanks. That was really helpful."

You do not remove your hand from the dildo. She does not move either.

"So," you lick your lips, "were you just planning on... hanging in my room with your dick out?"

"Yeah? I mean I can't really... do anything with it." She wrings her hands nervously. "Is it weird?"

"No, but I was going to suggest doing something a bit more fun with it."

She has to know what you mean. Fairy eyes, for one. Your complete lack of subtlety, for another. Still, she stares down at you, and asks: "... As in?"

Well. Now or never. If she rejects you, she rejects you, but fuck you are dying here. "I could suck your cock, Sir."

She takes a deep breath at the sir, clearly taken aback by the title. She opens her mouth. Closes it. Opens it again. "Do you propose to anyone who comes to you with their dick out?"

"No, only if I'm in the mood." Which, to be fair, is really easy to get you into, because gods you fucking love sucking dick. Top ten of your favorite activities of all times. You think that before the whole incineration of humanity thing (though you try not to think too hard about this period of your life, not that you remember much anyways) you were a lot more reserved regarding sex. What a mistake! If all parties consent and it feels good, why refuse it? Why deny yourself comfort and pleasure when you could all very well be separated tomorrow?

"So," you set one hand on top of Artoria's thigh, hooking a finger in her harness. The other hand gives the dildo a jerk. "What do you say, Sir?"

She hesitates only for a second. Then both her hands take a fistful of your hair. "I say open wide, puppy."

And oh, you do.

She can't feel it, of course- as far as you can tell, there is nothing magic in this silicone cock of hers. So you focus on giving her a show instead; you give her broad strokes with your tongue, keep eye contact as you kiss the side of her lenght. When, frustrated, she guides you back to her tip, you take a deep breath and swallow her whole in your throat, showing off your lack of gag reflex. Considering the look in her eyes as you nestle your nose against her pelvis, consider that a win.

Stubbornly, you stay here. It takes her a few seconds to understand that you don't intend to move. So she does instead; thrusts her hips, in shallow, timid strokes, as if testing the waters. You moan deeply, encouraging her to keep going; unboldened, she starts thrusting harder, deeper, until she's straight-up fucking your face.

Ah, fuck. You love this; you love how tightly she's holding on you, and her lenght dragging itself all the way across your tongue, and the building confidence in her eyes as she sees you submitting completely to her whim. The only thing that could make this better would be some thick, bitter come to swallow- but alas, that is not for today (something to convince Merlin of, perhaps?)

Eventually, she pulls you off her lenght. It's coated in saliva by now. Drool dribbles down your chin. You are uninterested in wiping it.

Artoria looks down at you, panting, faced flushed. "Hey, uh- do you- can I-"

"Fuck something more interesting than a face?" You grin up at her. "Would you be so kind as to get the lube in the bedside table, Sir? I will undress."

And undress you do. You don't know if she's watching, but just in case- you make a show of it, too. Take as much time as you need to uncover a hip, a thigh, an ankle, every patch of skin a treat that must be earned through patience. When finally, you fall on your bed, raising your knees to present your hole, she's holding the lube so tightly you fear she might break the bottle.

"Come here, Sir. Won't you prepare me?"

She drops on the bed, kneeling next to you. Her fingers are shaking as she pops open the bottle. "I, uhm, I've never..."

Ahh. Need a little prop of self confidence, doesn't she. You reach out and gently cup her face. "Easy, Sir. It's okay. I'll walk you through it."

You're the one to pour the lube on her hands, and the one to guide her between your thighs as well. "Look at how hard I am for you, Sir." You whisper in her ear. "Look at what you're doing to me." 

Her fingers are short, and thin- thinner than any of your owns, at least. Still, you squirm under her touch, hums praises and compliments as she explores your body, and when finally, three fingers deep, she brushes against your prostate, you're not faking in the slightest when you beg her to take you right here.

Artoria is small, but she's still a servant- and as such, has no trouble lifting your hips for easier access. She sinks inside of you, slowly, and you wish you wish she could feel your insides for herself, feel how warm and tight you are for her.

When she bottoms out, she looks down at you. "Are you... alright?"

You can't help it. You grab her by the tie and force her down, mashing your lips against hers. She startles at the sudden movement, so you lock your legs and arms around her to keep her close. You need her against you, inside you, you need her, you need her, gods, does this man not realize that she's driving you insane?

"Sir," you breathe out when the two of you finally part, (and oh, her lip is bleeding, it is so, so attractive,) "won't you do me a favor and mess me up?"

She nods, shakingly, and finally, finally she starts fucking you.

It's clumsy, of course- her aim is faulty, and her strenght erratic. When she hits a good spot, it's more often by accident than on purpose. You don't care. How can you? Her hands are spread on your hips, holding you tight. How can you? Her mouth is at your throat, nipping hickeys all around your neck. How can you? The sex may not be mind-blowing, but the contact, the intimacy- this is real, this is real, this is real.

You whisper in her ears. You're so good, Sir, you're so hard inside of me, right here Sir that's the spot, and you can feel her tense up whenever you hit a kink, redoubling her efforts to please you.

This doesn't last long, unfortunately. She's simply not used to being on this side of sex. She'll have to build her stamina over time. (With you, hopefully.)

"I, uh," she's huffing and puffing above you, "I'm sorry, I can't-"

"It's fine. I got it." You give her a tight hug, squeezing her against you. "I'm still hard. We can finish the traditional way, if you want."

She makes a non-commital noise. Doesn't seem overjoyed by the idea. Makes sense. Who wants to hear that they're bad at sex?

Hm. Okay. Let's try this.

Using your legs as leverage, you suddenly flip her over. She squeaks as she lands on her back. You climb on her and, swiftly, sit on her to guide her dick right back inside of you where it belongs.

"Or," you set your hands on her stomach, "I could ride you, if you'd like, Sir."

You grab one of her hand, then bring it to your own cock. Your precum smears over her palm.

"Although," you grin, "I might dirty that nice suit of yours. White streaks on black fabric. It'll be quite striking, don't you think?"

Ah, there, that look is back, awe and surprise and arousal.

"So, Sir," You jerk your hips once, fucking yourself on her, fucking your cock in her hand, "what will it be?"

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