Demon Lord's Reincarnation

I could already imagine how the night was going but as everyone else was supportive of what Kaley was trying to do, they just let me walk over to the partially ajar door when Kaley and Ella had just walked in. And as I did, Kaley made me lock the door behind me from a glance but as I turned around to look at Ella, her breathing was already hurried and she couldn't even look at us in the eye.

"Ella…" Kaley leaned over slightly to meet her eyes, "Breathe…"

Ella nodded a few times, "A-Alright... Ha.. Haa… P-Pretty n-nervous Haha… Ha…"

I said gently as well, "Imagine I'm not here unless you want to. This is a free space, you can ask us about anything."

"T-Thank you…" Ella took another deep breath as she turned to Kaley, "S-So… D-Do I t-take off m-my clothes—"

Kaley shook her head with a smile, "No. At least not yet, breathe again."

"O-Okay… Okay… Ha… Ha… Haa… Huuu~"

"..."

"..."

At this point, what's more important was to make Ella take off some more of her nervousness. If this night goes as intended, it should at least be a little special for her so that she wouldn't be averse or scared to do it in the future with us or anyone else for that matter.

So yeah, we sat in silence for a little bit, glancing at each other while wearing faint smiles, but as soon as Ella could look each of us in the eye without looking away all red and bothered, Kaley proceeded to ask a few questions of her own:

"Ella?"

"Y-Yes?"

"Umm… I forgot to ask but… I know you're kinda into him but are you also into me? I mean, women in general?"

"Umm…"

"If you're not, it's totally okay—and I'll still answer some questions, but if you want to be alone with him, it's fine too and he could also answer your questions. I'm totally okay with that."

Ella shook her head, "I… I don't actually k-know but…"

"Hmm?"

"I-I do think you're really p-pretty…"

"Oh! Why, thank you! You look pretty as well— I heard you design clothes, would you care to make me one in the future? I'm looking for a sundress that's really comfy but shows a little skin but you're totally in charge of what it could look like—"

"R-Really?! You don't find my designs weird?"

Kaley chuckled as she pointed at me for a moment, "You see that guy? He'd be on the moon if he saw me in cosplay but on normal days, he'd just love it when I wear oversized shirts and thigh-high socks— no bra and just panties."

"Oh. Oh! N-Noted! B-But my designs, do you like them?"

"I do, really, I LOVE Ranch but have you made something like a strawberry shortcake?"

"OH! I would love to make you something like that! I-I already have an idea in mind! I… W-Wait!"

"Hmm?"

"A-Aren't we supposed to t-talk about—"

"Seckus?"

"You— D-Don't make fun of me, please! I'm already—"

Kaley gave her a nudge, "Oh, c'mon! That's adorable, besides, we're already doing part of it. You see, one of the most important parts of doing 'that' is to be really~ comfortable with your partner or partners first. Don't get me wrong, I would really love a new sundress but it took a lot of the nervousness off, right?"

"I-It did… I— B-But when can I ask—"

"You can ask one right now. You're comfortable now, right?"

Ella nodded a few times, "O-Okay… U-Umm… Would… W-Would it r-really hurt? I heard that if it's your f-first time, it really does, b-but some people said it d-didn't. And I… I-I did try p-putting a f-finger in o-one time a-and i-it pinched a bit so I s-stopped… It's just… I-I'm really afraid and i-is there a way so that i-it just n-not hurt?"

Kaley looked at her gently, "Ella…"

"I'm sorry—"

"What? Don't be sorry! Well~ About your question, here's the thing: it would really hurt but it depends on the person and their pain tolerance. However, the more you're aroused, the less it would—at least in my experience—but to be completely honest with you, it would pinch a bit more and even hurt a few more times when you do it again, realistically speaking."

"Really?"

"To be fair though, it's a mix? With feeling good and feeling that pinch but do know that if it gets too much or unbearable—if you decide to do it tonight—we'll completely stop and not pursue anything more."

"B-But h-how would he f-feel good?"

I cut in with a smile, "That's not how it works."

Kaley nodded, "That's true. You said it yourself, you tried to put it in when you were masturbating, right?"

"Y-Yes?"

"Then… You should've at least made yourself orgasm every once in a while and—"

"Huh? S-Shouldn't s-something be i-inside first—"

"Wait a second… Ella… Have you… Have you made yourself c-cum yet?"

"..."

"Oh no…" Kaley and I said at the same time.

"I-Is there something wrong with me?!"

Kaley waved her off, "N-No, no, no! You're perfect! It's just that… You went to school, right?"

"Yes? I majored in fashion design—"

"We do know that but there should be minor subjects and biology or even sex ed should be—"

I cut in, "Did you do it online?"

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"Huh?"

"I mean, your degree?"

"Y-Yes?"

"That's why…" Kaley and I said at the same time again.

"H-Hey! I-IT'S COMPLETELY LEGIT! IT'S A REAL SCHOOL!"

I waved her off, "I know, I know! It's not about that but it seemed like you have a lot to catch up on regarding that particular subject— And I'm gonna say it now: you don't have to put it in you to cum like I don't have to put it in you or Kaley's or anyone's to cum."

Ella was in complete disbelief, "No… No way— I thought—"

Kaley interjected, "Have you… Have you at least rubbed… played with your nipples or your clit— clitoris—"

"I-Isn't that bad? Aren't we supposed to not do that?"

Kaley and I never looked so confused as we asked at the same time, "And why do you think that?"

"It's… S-Sister Dorothy said that w-we shouldn't because you know… I-It's bad— A sin!"

"That's why…" Kaley and I said at the same time after figuring it out.

"S-She really did a-and— I-I do accidentally touch it a little more sometimes when I s-shower but when my b-body f-feels really weird I stop… That's why I know it's really bad because I'm really moody after but— Why are you two looking at me like that?!"